2,4,6-Trihydroxy propiophenone-4-O-3’-3’dimethylallyl ether (1)
C14H18O4
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Leontonyx squarrosus
South Africa4141 Bohlmann, F.; Suwita, A.; Phytochemistry 1978, 17, 1929. [Crossref] Crossref...
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1H NMR (270 MHz, CDCl3)
THB core: δ 5.93 (H-3 and H-5)
prenyl group: δ 4.50 (H-1), 5.45 (H-2), 1.74 (H-4), and 1.81 (H-5)
acyl group: δ 3.10 (H-1), and 1.18 (H-2)4141 Bohlmann, F.; Suwita, A.; Phytochemistry 1978, 17, 1929. [Crossref] Crossref...
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2,4,6-Trihydroxy isobutyrophenone-4-O-3’,3’-dimethylallyl ether (2)
C15H20O4
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Leontonyx squarrosus
South Africa4141 Bohlmann, F.; Suwita, A.; Phytochemistry 1978, 17, 1929. [Crossref] Crossref...
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1H NMR (270 MHz, CDCl3)
THB core: δ 10.25 (OH-2 and OH-6), and 5.95 (H-3 and H-5)
prenyl group: δ 4.49 (H-1), 5.44 (H-2), 1.72 (H-4), and 1.79 (H-5)
acyl group: δ 3.90 (H-1) and 1.19 (H-2 and H-3)4141 Bohlmann, F.; Suwita, A.; Phytochemistry 1978, 17, 1929. [Crossref] Crossref...
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2,4,6-Trihydroxy-2-methylbutyrophenone-4-O-3’,3’-dimethylallyl ether (3)
C16H22O4
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Leontonyx squarrosus
South Africa4141 Bohlmann, F.; Suwita, A.; Phytochemistry 1978, 17, 1929. [Crossref] Crossref...
Hypericum empetrifolium
Greece33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
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1H NMR (600 MHz, CDCl3)
THB core: δ 9.72 (OH-2 and OH-6) and 5.92 (H-3 and H-5)
prenyl group: δ 4.49 (H-1), 5.44 (H-2), 1.79 (H-4), and 1.73 (H-5)
acyl group: δ 3.70 (H-1), 1.40 (H-2), 1.84 (H-2), 0.91 (H-3), and 1.16 (H-4)
13C NMR (150 MHz, CDCl3)
THB core: δ 104.4 (C-1), 164.5 (C-2), 95.1 (C-3), 164.5 (C-4), 95.1 (C-5), and 163.1 (C-6)
prenyl group: δ 65.0 (C-1), 118.6 (C-2), 139.1 (C-3), 25.8 (C-4), and 18.2 (C-5)
acyl group: δ 209.9 (C-1’), 45.9 (C-1), 26.8 (C-2), 11.9 (C-3), and 16.5 (C-4)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
1H NMR (400 MHz, CDCl3)
THB core: δ 5.91 (H-3 and H-5)
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1-(2-Methylbutanone)-4-O-prenyl-phloroglucinol (4)
C16H22O4
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Helichrysum niveum
South Africa4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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prenyl group: δ 4.47 (H-1), 5.42 (H-2), 1.77 (H-4), and 1.71 (H-5)
acyl group: δ 3.70 (H-1), 1.38 (H-2), 0.89 (H-3), and 1.14 (H-4)
13C NMR (100 MHz, CDCl3)
THB core: δ 104.5 (C-1), 164.6 (C-2, C-4, and C-6), and 95.1 (C-3 and C-5)
prenyl group: δ 65.1 (C-1), 118.7 (C-2), 139.2 (C-3), 18.2 (C-4), and 25.8 (C-5)
acyl group: δ 210.1 (C-1’), 45.9 (C-1), 26.9 (C-2), 16.6 (C-3), and 11.9 (C-4)4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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1-(2-Methylpropanone)-4-O-prennyl-phloroglucinol (5)
C15H20O4
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Helichrysum niveum
South Africa4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 5.91 (H-3 and H-5) and 9.92 (OH-2 and OH-6)
prenyl group: δ 4.47 (H-1), 5.42 (H-2), 1.77 (H-4), and 1.71 (H-5)
acyl group: δ 3.83 (H-1) and 1.59 (H-2 and H-3)
13C NMR (100 MHz, CDCl3)
THB core: δ 104.0 (C-1), 164.7 (C-2, C-4, and C-6), and 95.1 (C-3 and C-5)
prenyl group: δ 65.1 (C-1), 118.7 (C-2), 139.2 (C-3), 18.2 (C-4), and 25.8 (C-5)
acyl group: δ 210.2 (C-1’), 39.3 (C-1), and 19.2 (C-2 and C-3)4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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4-Geranyloxy-1-(2-methylpropanoyl)-phloroglucinol (6)
C20H28O4
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Helichrysum gymnoconum
South Africa4343 Bohlmann, F.; Mahanta, P. K; Phytochemistry 1979, 18, 348. [Crossref] Crossref...
Hypericum densiflorum
United States4444 Henry, G E.; Campbell, M. S.; Zelinsky, A. A.; Liu, Y; Bowen-Forbes, C. S.; Li, L.; Nair, M. G.; Rowley, D. C; Seeram, N. P.; Phytother. Res. 2009, 23, 1759. [Crossref] Crossref...
Hypericum jovis
Greece4545 Athanasas, K; Magiatis, P.; Fokialakis, N.; Skaltsounis, A. L.; Pratsinis, H.; Kletsas, D.; J. Nat. Prod. 2004, 67, 973. [Crossref] Crossref...
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1H NMR (270 MHz, CDCl3)
THB core: δ 5.96 (H-3 and H-5) and 9.2 (OH-2 and OH-6)
geranyl group:a δ 4.51 (H-1), 5.43 (H-2), 2.09 (H-4 and H-5), 5.08 (H-6), 1.60 (H-8), 1.71 (H-9), and 1.67 (H-9)4343 Bohlmann, F.; Mahanta, P. K; Phytochemistry 1979, 18, 348. [Crossref] Crossref...
13C NMR (50 MHz, CDCl3)
THB core: δ 104.0 (C-1), 164.7 (C-2), 94.5 (C-3 and C-5), 163.3 (C-4), and 164.7 (C-6)
geranyl group:a δ 65.1 (C-1), 118.4 (C-2), 142.1 (C-3), 39.5 (C-4), 26.2 (C-5), 123.6 (C-6), 131.9 (C-7), 25.7 (C-8), 16.7 (C-9), and 17.7 (C-10)
acyl group: δ 210.2 (C-1’), 39.2 (C-1), and 19.2 (C-2 and C-3)4545 Athanasas, K; Magiatis, P.; Fokialakis, N.; Skaltsounis, A. L.; Pratsinis, H.; Kletsas, D.; J. Nat. Prod. 2004, 67, 973. [Crossref] Crossref...
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2,6-Dihydroxy-4-geranyloxyacetophenone (7)
C18H24O4
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Evodia merrillii
Taiwan4646 Chou, C. J.; Lin, L C; Chen, K. T.; Chen, C. F; J. Nat. Prod. 1992, 55, 795. [Crossref] Crossref...
Melicope obscura
Reunion Island4747 Adsersen, A.; Smitt, U. W; Simonsen, H. T.; Christensen, S. B.; Jaroszewski, J. W.; Biochem. Syst. Ecol. 2007, 35, 447. [Crossref] Crossref...
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1H NMRb (300 MHz)
THB core: δ 5.95 (H-3 and H-5)
geranyl group:a δ 4.47 (H-1), 5.39 (H-2), 2.06 (H-4 and H-5), 5.04 (H-6), 1.56 (H-8), 1.67 (H-9), and 1.64 (H-10)
acyl group: δ 2.68 (CH3)
13C NMRb (75 MHz)
THB core: 105.2 (C-1), 163.8 (C-2), 94.7 (C-3), 165.5 (C-4), 94.7 (C-5), and 163.8 (C-6),
geranyl group:a δ 65.1 (C-1), 118.3 (C-2), 142.2 (C-3), 39.4 (C-4), 26.2 (C-5), 123.6 (C-6), 131.8 (C-7), 17.6 (C-8), 16.5 (C-9), and 25.5 (C-10)
acyl group: δ 204.1 (C-1’) and 32.4 (CH3)4646 Chou, C. J.; Lin, L C; Chen, K. T.; Chen, C. F; J. Nat. Prod. 1992, 55, 795. [Crossref] Crossref...
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4-Geranyloxy-1-(2-methylbutanoyl)-phloroglucinol (8)
C21H30O4
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Helichrysum gymnoconum
South Africa4343 Bohlmann, F.; Mahanta, P. K; Phytochemistry 1979, 18, 348. [Crossref] Crossref...
Hypericum densiflorum
United States4444 Henry, G E.; Campbell, M. S.; Zelinsky, A. A.; Liu, Y; Bowen-Forbes, C. S.; Li, L.; Nair, M. G.; Rowley, D. C; Seeram, N. P.; Phytother. Res. 2009, 23, 1759. [Crossref] Crossref...
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1H NMR (270 MHz, CDCl3)
THB core: δ 5.96 (H-3 and H-5) and 9.2 (OH-2 and OH-6)
geranyl group:a δ 4.51 (H-1), 5.43 (H-2), 2.09 (H-4 and H-5), 5.08 (H-6), 1.60 (H-8), 1.71 (H-9), and 1.67 (H-9)4343 Bohlmann, F.; Mahanta, P. K; Phytochemistry 1979, 18, 348. [Crossref] Crossref...
13C NMR (100 MHz, CDCl3)
THB core: δ 106.0 (C-1), 167.6 (C-2), 91.6 (C-3), 162.1 (C-4), 96.5 (C-5), and 162.6 (C-6)
geranyl group:a δ 65.7 (C-1), 118.2 (C-2), 142.5 (C-3), 39.6 (C-4), 25.8 (C-5), 123.7 (C-6), 132.1 (C-7), 26.4 (C-8), 16.6 (C-9), and 17.8 (C-10)
acyl group: δ 210.5 (C-1’), 46.2 (C-1), 26.9 (C-2), 12.0 (C-3), and 16.7 (C-4)4444 Henry, G E.; Campbell, M. S.; Zelinsky, A. A.; Liu, Y; Bowen-Forbes, C. S.; Li, L.; Nair, M. G.; Rowley, D. C; Seeram, N. P.; Phytother. Res. 2009, 23, 1759. [Crossref] Crossref...
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4-Geranyloxy-2,6,β-trihydroxyacetophenone (9)
C18H24O5
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Evodia merrillii
Taiwan4646 Chou, C. J.; Lin, L C; Chen, K. T.; Chen, C. F; J. Nat. Prod. 1992, 55, 795. [Crossref] Crossref...
Melicope obscura
Reunion Island4747 Adsersen, A.; Smitt, U. W; Simonsen, H. T.; Christensen, S. B.; Jaroszewski, J. W.; Biochem. Syst. Ecol. 2007, 35, 447. [Crossref] Crossref...
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1H NMRb (300 MHz) 4.33 (OH), and 10.45 (OH)
THB core: δ 5.95 (H-3 and H-5)
geranyl group:a δ 4.51 (H-1), 5.40 (H-2), 2.07 (H-4 and H-5), 5.06 (H-6), 1.58 (H-8), 1.70 (H-9), and 1.65 (H-10)
acyl group: δ 4.81 (CH2)
13C NMRb (75 MHz)
THB core: δ 102.5 (C-1), 163.7 (C-2), 94.8 (C-3), 166.5 (C-4), 94.8 (C-5), and 163.7 (C-6)
geranyl group:a δ 65.3 (C-1), 118.3 (C-2), 142.4 (C-3), 39.3 (C-4), 26.2 (C-5), 123.6 (C-6), 131.9 (C-7), 17.7 (C-8), 16.7 (C-9), and 25.6 (C-10)
acyl group: δ 200.7 (C-1’) and 68.0 (CH2)4646 Chou, C. J.; Lin, L C; Chen, K. T.; Chen, C. F; J. Nat. Prod. 1992, 55, 795. [Crossref] Crossref...
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4-Farnesyloxy-2,6-dihydroxyacetophenone (10)
C23H32O4
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Boronza ramose
Australia4848 Ahsan, M.; Gray, A. I..; Waterman; P. G; Armstrong, J. A.; J. Nat. Prod. 1994, 57, 673. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 5.95 (H-3 and H-5)
R4 group: δ 4.52 (H-1), 5.44 (H-2), 1.94-2.16 (H-4, H-5, H-8, and H-9), 5.09 (H-6), 5.09 (H-10), 1.68 (H-12), 1.73 (H-13), 1.60 (H-14), and 1.60 (H-15)
acyl group: δ 2.69 (CH3)
13C NMR (100 MHz, CDCl3)
THB core: δ 105.3 (C-1), 163.6 (C-2 and C-6), 95.0 (C-3 and C-5), and 165.4 (C-4)
R4 group: δ 65.4 (C-1), 118.6 (C-2), 142.5 (C-3), 39.7 (C-4), 26.3 (C-5), 123.7 (C-6), 135.8 (C-7), 39.9 (C-8), 26.9 (C-9), 124.5 (C-10), 131.6 (C-11), 25.9 (C-12), 16.9 (C-13), 16.2 (C-14), and 17.9 (C-15)
acyl group: δ 203.7 (C-1’) and 32.9 (CH3)4848 Ahsan, M.; Gray, A. I..; Waterman; P. G; Armstrong, J. A.; J. Nat. Prod. 1994, 57, 673. [Crossref] Crossref...
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Acronylin (11)
C14H18O4
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Remirea maritima
c
4949 Allan, R. D.; Wells, R. J.; Macleod, J. K; Tetrahedron Lett. 1970, 11, 3945. [Crossref] Crossref...
Acronychia pedunculata
Sri Lanka5050 Kumar, V.; Karunaratne, V.; Sanath, M. R.; Meegalle, K; Phytochemistry 1989, 28, 1278. [Crossref] Crossref...
Taiwan5151 Ito, C; Hosono, M.; Tokuda, H; Wu, T. S.; Itoigawa, M.; Nat. Prod. Commun. 2016, 11, 1299. [Crossref] Crossref...
Melicope stipitata
Australia5252 Parsons, I. C; Gray, A. I.; Hartley, T. G; Waterman, P. G.; Phytochemistry 1994, 37, 565. [Crossref] Crossref...
Acronychia trifoliolata
Indonesia5353 Miyake, K; Suzuki, A.; Morita, C; Goto, M.; Newman, D. J.; O'Keefe, B. R.; Morris-Natschke, S. L.; Lee, K H.; Goto, K. N.; J. Nat. Prod. 2016, 79, 2883. [Crossref] Crossref...
Acronychia pubescens
Australia5454 Robertson, L. P.; Lucantoni, L.; Duffy, S.; Avery, V. M.; Carroll, A. R.; J. Nat. Prod. 2019, 82, 1019. [Crossref] Crossref...
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NMR data not found |
1-(2-Methylbutanone)-3-prenylphloroglucinol (12)
C16H22O4
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Helichrysum gymnoconum
South Africa4343 Bohlmann, F.; Mahanta, P. K; Phytochemistry 1979, 18, 348. [Crossref] Crossref...
Helichrysum niveum
South Africa4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 5.83 (H-3), 8.81(OH-4), and 11.76 (OH-6)
prenyl group: δ 3.32 (H-1), 5.21 (H-2), 1.73 (H-4), and 1.78 (H-5)
acyl group: δ 3.74 (H-1), 1.37 (H-2), 0.88 (H-3), and 1.13 (H-4)
13C NMR (100 MHz, CDCl3)
THB core: δ 105.7 (C-1), 160.7 (C-2), 95.4 (C-3), 159.9 (C-4), 104.7 (C-5), and 162.6 (C-6)
prenyl group: δ 21.6 (C-1), 121.6 (C-2), 135.9 (C-3), 25.8 (C-4), and 17.9 (C-5)
acyl group: δ 210.8 (C-1’), 45.9 (C-1), 26.9 (C-2), 11.9 (C-3), and 16.9 (C-4)4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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1-(2-Methylpropanone)-3-prenylphloroglucinol (13)
C15H20O4
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Helichrysum gymnoconum
South Africa1010 Drewes, S. E.; Sandy, F. V.; Phytochemistry 2008, 69, 1745. [Crossref] Crossref...
,4343 Bohlmann, F.; Mahanta, P. K; Phytochemistry 1979, 18, 348. [Crossref] Crossref...
Helichrysum kraussii
South Africa5555 Bremner, P. D.; Meyer, J. J. M.; S. Afr. J. Bot. 2000, 66, 115. [Crossref] Crossref...
Helichrysum niveum
South Africa4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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1H NMR (400 MHz, CD3COCD3)
THB core: δ 6.06 (H-3), 9.33 (OH-4), and 14.09 (OH-6)
prenyl group: δ 3.23 (H-1), 5.21 (H-2), 1.73 (H-4), and 1.62 (H-5)
acyl group: δ 3.98 (H-1) and 1.12 (H-2 and H-3)
13C NMR (100 MHz, CD3COCD3)
THB core: δ 104.3 (C-1), 160.1 (C-2), 95.1 (C-3), 162.5 (C-4), 108.0 (C-5), and 165.2 (C-6)
prenyl group: δ 22.1 (C-1), 124.2 (C-2), 130.8 (C-3), 17.9 (C-4), and 25.9 (C-5)
acyl group: δ 210.9 (C-1’), 39.7 (C-1), and 19.8 (C-2 and C-3)4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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1-(Butanone)-3-prenyl-phloroglucinol (14)
C15H20O4
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Helichrysum niveum
South Africa4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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1H NMR (400 MHz, CD3COCD3)
THB core: δ 6.05 (H-3), 9.31 (OH-4), and 14.1 (OH-6)
prenyl group: δ 3.22 (H-1), 5.20 (H-2), 1.61 (H-4), and 1.72 (H-5)
acyl group: δ 3.04 (H-1), 1.67 (H-2), and 0.94 (H-3)
13C NMR (100 MHz, CD3COCD3)
THB core: δ 105.1 (C-1), 162.6 (C-2), 95.0 (C-3), 160.5 (C-4), 107.9 (C-5), and 165.2 (C-6)
prenyl group: δ 22.0 (C-1), 124.3 (C-2), 130.8 (C-3), 26.0 (C-4), and 17.9 (C-5)
acyl group: δ 206.5 (C-1’), 46.5 (C-1), 19.0 (C-2), and 14.4 (C-3)4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
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2-(1’-Geranyloxy)-4,6-dihydroxyacetophenone (15)
C18H24O4
|
Evodia merrillii
Taiwan4646 Chou, C. J.; Lin, L C; Chen, K. T.; Chen, C. F; J. Nat. Prod. 1992, 55, 795. [Crossref] Crossref...
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1H NMRb (300 MHz)
THB core: δ 5.96 (H-3), 5.90 (H-5), 6.17 (OH-2 or OH-4), and 13.96 (OH-2 or OH-4)
geranyl group:a δ 4.54 (H-1), 5.48 (H-2), 2.09 (H-4 and H-5), 5.06 (H-6), 1.59 (H-8), 1.72 (H-9), and 1.66 (H-10)
acyl group: δ 2.60 (CH3)
13C NMRb (75 MHz)
THB core: δ 106.4 (C-1), 167.2 (C-2), 96.3 (C-3), 163.1 (C-4), 91.6 (C-5), and 162.7 (C-6)
geranyl group:a δ 65.7 (C-1), 118.4 (C-2), 142.2 (C-3), 39.4 (C-4), 26.2 (C-5), 123.6 (C-6), 132.0 (C-7), 17.7 (C-8), 16.6 (C-9), and 25.6 (C-10)
acyl group: δ 203.5 (C-1’) and 33.0 (CH3)4646 Chou, C. J.; Lin, L C; Chen, K. T.; Chen, C. F; J. Nat. Prod. 1992, 55, 795. [Crossref] Crossref...
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2-(1’-Geranyloxy)-4,6,β-trihydroxyacetophenone (16) C18H24O5
|
Evodia merrillii
Taiwan5656 Lin, L.-C; Chou, C.-J.; Chen, K. T.; Chen, C.-F; J. Nat. Prod. 1993, 56, 926. [Crossref] Crossref...
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1H NMRd (CDCl3) δ 3.89 (OH), 6.27 (OH), and 13.09 (OH)
THB core: δ 5.90 (H-3) and 6.00 (H-5)
geranyl group:a δ 4.56 (H-1), 5.48 (H-2), 2.10 (H-4 and H-5), 5.07 (H-6), 1.59 (H-8), 1.72 (H-9), and 1.67 (H-10)
acyl group: δ 4.71 (CH2)
13C NMRd (CDCl3)
THB core: δ 103.7 (C-1), 166.9 (C-2), 96.5 (C-3), 163.9 (C-4), 91.8 (C-5), and 163.4 (C-6)
geranyl group:a δ 65.9 (C-1), 117.8 (C-2), 143.0 (C-3), 39.5 (C-4), 26.3 (C-5), 123.5 (C-6), 132.1 (C-7), 17.7 (C-8), 16.6 (C-9), and 25.6 (C-10)
acyl group: δ 201.7 (C-1’) and 68.6 (CH2)5656 Lin, L.-C; Chou, C.-J.; Chen, K. T.; Chen, C.-F; J. Nat. Prod. 1993, 56, 926. [Crossref] Crossref...
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2,4,6-Trihydroxy-3-geranyl-acetophenone (17)
C18H24O4
|
Melicope ptelefolia
Malaysia5757 Shaari, K; Safri, S.; Abas, F; Lajis, N. H.; Israf, A. D.; Nat. Prod. Res. 2006, 20, 415. [Crossref] Crossref...
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1H NMR (500 MHz, CD3OD)
THB core: δ 5.92 (H-3)
geranyl group:a δ 3.21 (H-1), 5.20 (H-2), 1.96 (H-4), 2.06 (H-5), 5.08 (H-6), 1.63 (H-8), 1.76 (H-9), and 1.58 (H-10)
acyl group: δ 2.64 (CH3)
13C NMR (125 MHz, CD3OD)
THB core: δ 104.3 (C-1), 160.7 (C-2), 93.6 (C-3), 162.8 (C-4), 106.8 (C-5), and 163.7 (C-6)
geranyl group:a δ 20.9 (C-1), 123.5 (C-2), 133.5 (C-3), 39.8 (C-4), 26.6 (C-5), 124.4 (C-6), 130.8 (C-7), 24.7 (C-8), 15.0 (C-9), and 16.6 (C-10)
acyl group: δ 203.4 (C-1’) and 31.7 (CH3)5757 Shaari, K; Safri, S.; Abas, F; Lajis, N. H.; Israf, A. D.; Nat. Prod. Res. 2006, 20, 415. [Crossref] Crossref...
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3-Geranyl-1-(2’-methylpropanoyl) phloroglucinol (18)
C20H28O4
|
Hypericum natalitium
South Africa5858 Bohlmann, F.; Zdero, C; Phytochemistry 1979, 18, 641. [Crossref] Crossref...
Achyrocline alata
Brazil5959 Bohlmann, F.; Abraham, W. R.; Robinson, H; King, R. M.; Phytochemistry 1980, 19, 2475. [Crossref] Crossref...
Esenbeckia nesiotica
Mexico6060 Rios, M. Y; Delgado, G.; Phytochemistry 1992, 31, 3491. [Crossref] Crossref...
Hypericum styphelioides
Cuba6161 Gamiotea-Turro, D.; Cuesta-Rubio, O.; Prieto-González, S.; de Simone, F; Passi, S.; Rastrelli, L.; J. Nat. Prod. 2004, 67, 869. [Crossref] Crossref...
Hypericum jovis
Greece4545 Athanasas, K; Magiatis, P.; Fokialakis, N.; Skaltsounis, A. L.; Pratsinis, H.; Kletsas, D.; J. Nat. Prod. 2004, 67, 973. [Crossref] Crossref...
,6262 Grafakou, M. E.; Barda, C; Pintać, D.; Lesjak, M.; Heilmann, J.; Skaltsa, H; Planta Med. 2021, 87, 1184. [Crossref] Crossref...
Hypericum empetrifolium
Austria6363 Crockett, S. L.; Wenzig, E. M.; Kunert, O.; Bauer, R.; Phytochem. Lett. 2008, 1, 37. [Crossref] Crossref...
Greece3
Hypericum spp.
United States6464 Sarkisian, S. A.; Janssen, M. J.; Matta, H.; Henry, G. E.; LaPlante, K. L.; Rowley, D. C; Phytother. Res. 2011, 26, 1012. [Crossref] Crossref...
Hypericum roeperianum
Cameroon6565 Fobofou, S. A. T.; Franke, K; Sanna, G.; Porzel, A.; BuUita, E.; Colla, P.; Wessjohann, L. A.; Bioorg. Med. Chem. 2015, 23, 6327. [Crossref] Crossref...
Garcinia dauphinensis
Madagascar6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
Hypericum annulatum
Rhodopi Mountain3535 Nedialkov, P. T.; Ilieva, Y.; Momekov, G.; Kokanova-Nedialkova, Z.; Fitoterapia 2018, 127, 375. [Crossref] Crossref...
Hypericum faberi
China6767 Zhang, X. W; Fan, S. Q.; Xia, F; Ye, Y. S.; Yang, X. W;Yang, X. W; Xu, G.; J. Nat. Prod. 2019, 82, 1367. [Crossref] Crossref...
Hypericum japonicum
China6868 Peng, X.; Tan, Q.; Zhou, H.; Xu, J.; Gu, Q.; Fitoterapia 2021, 153, 104984. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 8.31 (OH-2), 5.97 (OH-4), 11.60 (OH-6), and 5.83 (H-3)
geranyl group:a δ 3.38 (H-1), 5.26 (H-2), 2.09 (H-4), 2.11 (H-5), 5.05 (H-6), 1.67 (H-8), 1.81 (H-9), and 1.59 (H-10)
acyl group: δ 3.87 (H-1) and 1.17 (H-2 and H-3)
13C NMR (150 MHz, CDCl3)
THB core: δ 104.1 (C-1), 159.9 (C-2), 95.4 (C-3), 160.6 (C-4), 105.6 (C-5), and 162.6 (C-6)
geranyl group:a δ 21.6 (C-1), 121.4 (C-2), 140.1 (C-3), 39.6 (C-4), 26.2 (C-5), 123.5 (C-6), 132.1 (C-7), 25.6 (C-8), 16.2 (C-9), and 17.6 (C-10)
acyl group: δ 210.5 (C-1’), 39.2 (C-1), and 19.2 (C-2 and C-3)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
|
2-Geranyloxy-1-(2-methylpropanoyl) phloroglucinol (19)
C20H28O4
|
Hypericum spp.
United States6464 Sarkisian, S. A.; Janssen, M. J.; Matta, H.; Henry, G. E.; LaPlante, K. L.; Rowley, D. C; Phytother. Res. 2011, 26, 1012. [Crossref] Crossref...
|
NMR data not found |
3-Geranyl-1-(2’-methylbutanoyl) phloroglucinol (20)
C21H30O4
|
Hypericum natalitium
South Africa5858 Bohlmann, F.; Zdero, C; Phytochemistry 1979, 18, 641. [Crossref] Crossref...
Achyrocline alata
Brazil5959 Bohlmann, F.; Abraham, W. R.; Robinson, H; King, R. M.; Phytochemistry 1980, 19, 2475. [Crossref] Crossref...
Esenbeckia nesiotica
Mexico6060 Rios, M. Y; Delgado, G.; Phytochemistry 1992, 31, 3491. [Crossref] Crossref...
Hypericum empetrifolium
Austria6363 Crockett, S. L.; Wenzig, E. M.; Kunert, O.; Bauer, R.; Phytochem. Lett. 2008, 1, 37. [Crossref] Crossref...
Greece33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
Hypericum spp.
United States6464 Sarkisian, S. A.; Janssen, M. J.; Matta, H.; Henry, G. E.; LaPlante, K. L.; Rowley, D. C; Phytother. Res. 2011, 26, 1012. [Crossref] Crossref...
Hypericum roeperianum
Cameroon6565 Fobofou, S. A. T.; Franke, K; Sanna, G.; Porzel, A.; BuUita, E.; Colla, P.; Wessjohann, L. A.; Bioorg. Med. Chem. 2015, 23, 6327. [Crossref] Crossref...
Garcinia dauphinensis
Madagascar6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
Hypericum faberi
China6767 Zhang, X. W; Fan, S. Q.; Xia, F; Ye, Y. S.; Yang, X. W;Yang, X. W; Xu, G.; J. Nat. Prod. 2019, 82, 1367. [Crossref] Crossref...
Hypericum jovis
Greece6262 Grafakou, M. E.; Barda, C; Pintać, D.; Lesjak, M.; Heilmann, J.; Skaltsa, H; Planta Med. 2021, 87, 1184. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 8.20 (OH-2), 5.96 (OH-4), 11.75 (OH-6), and 5.82 (H-3)
geranyl group:a δ 3.38 (H-1), 5.26 (H-2), 2.09 (H-4), 2.11 (H-5), 5.05 (H-6), 1.68 (H-8), 1.82 (H-9), and 1.60 (H-10)
acyl group: δ 3.74 (H-1), 1.40 (H-2), 1.83 (H-2), 0.90 (H-3), and 1.16 (H-4)
13C NMR (150 MHz, CDCl3)
THB core: δ 104.8 (C-1), 159.9 (C-2), 95.4 (C-3), 160.7 (C-4), 105.6 (C-5), and 162.6 (C-6)
geranyl group:a δ 21.6 (C-1), 121.4 (C-2), 140.1 (C-3), 39.6 (C-4), 26.2 (C-5), 123.5 (C-6), 132.1 (C-7), 25.6 (C-8), 16.2 (C-9), and 17.7 (C-10)
acyl group: δ 210.3 (C-1’), 45.9 (C-1), 26.9 (C-2), 11.9 (C-3), and 16.6 (C-4)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
|
3-Geranyl-1-(2’-methylpropanoyl) phloroglucinol (21)
C20H28O4
|
Hypericum natalitium
South Africa5858 Bohlmann, F.; Zdero, C; Phytochemistry 1979, 18, 641. [Crossref] Crossref...
|
1H NMR (270 MHz, CDCl3)
THB core: δ 5.88 (H-5)
geranyl group:e δ 3.37 (H-1), 5.18 (H-2), 2.26 (H-4), 2.16 (H-5), 5.24 (H-6), 1.63 (H-8), 1.81 (H-9), and 1.70 (H-10)5858 Bohlmann, F.; Zdero, C; Phytochemistry 1979, 18, 641. [Crossref] Crossref...
|
2-Geranyloxy-1-(2-methylbutanoyl) phloroglucinol (22)
C21H30O4
|
Hypericum spp.
United States6464 Sarkisian, S. A.; Janssen, M. J.; Matta, H.; Henry, G. E.; LaPlante, K. L.; Rowley, D. C; Phytother. Res. 2011, 26, 1012. [Crossref] Crossref...
|
NMR data not found |
3-Geranyl-1-(3-methylbutanoyl)-phloroglucinol (23)
C21H30O4
|
Esenbeckia nesiotica
Mexico6060 Rios, M. Y; Delgado, G.; Phytochemistry 1992, 31, 3491. [Crossref] Crossref...
|
1H NMR (300 MHz, CDCl3)
THB core: δ 5.82 (H-3), 8.50 (OH-2), 6.08 (OH-4), and 11.62 (C-6)
geranyl group:a δ 3.39 (H-1), 5.24 (H-2), 2.10 (H-4 and H-5), 5.06 (H-6), 1.68 (H-8), 1.59 (H-9), and 1.81 (H-10)
acyl group: δ 2.94 (H-1), 2.26 (H-2), and 0.97 (H-3 and H-4)6060 Rios, M. Y; Delgado, G.; Phytochemistry 1992, 31, 3491. [Crossref] Crossref...
|
3-Geranyl-1-(2’-methylbutanoyl) phloroglucinol (24)
C21H30O4
|
Hypericum natalitium
South Africa5858 Bohlmann, F.; Zdero, C; Phytochemistry 1979, 18, 641. [Crossref] Crossref...
|
1H NMR (270 MHz, CDCl3)
THB core: δ 5.88 (H-5)
geranyl group:e δ 3.37 (H-1), 5.18 (H-2), 2.26 (H-4), 2.16 (H-5), 5.24 (H-6), 1.63 (H-8), 1.81 (H-9), and 1.70 (H-10)5858 Bohlmann, F.; Zdero, C; Phytochemistry 1979, 18, 641. [Crossref] Crossref...
|
Olympicin C (25)
C21H30O5
|
Hypericum olympicum
England6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
1H NMR (500 MHz, CDCl3)
THB core: δ 5.92 (H-3), 5.98 (H-5), and 13.99 (OH-6)
R2 group: δ 4.57 (H-1), 5.53 (H-2), 2.15 (H-4), 1.75 (H-5), 4.08 (H-6), 4.95 (H-8), 4.87 (H-8), 1.74 (H-9), and 1.76 (H-10)
acyl group: δ 3.64 (H-1), 1.37 (H-2), 1.80 (H-2), 0.88 (H-3), and 1.12 (H-4)
13C NMR (125 MHz, CDCl3)
THB core: δ 105.9 (C-1), 162.4 (C-2), 91.6 (C-3), 161.9 (C-4), 96.6 (C-5), and 167.6 (C-6)
R2 group: δ 65.6 (C-1), 118.7 (C-2), 141.9 (C-3), 35.5 (C-4), 26.8 (C-5), 75.5 (C-6), 147.2 (C-7), 111.4 (C-8), 17.6 (C-9), and 16.7 (C-10)
acyl group: δ 210.3 (C-1’), 46.1 (C-1), 26.8 (C-2), 11.9 (C-3), and 16.7 (C-4)6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
Olympicin D (26)
C21H30O6
|
Hypericum olympicum
England6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
1H NMR (500 MHz, CDCl3)
THB core: δ 5.91 (H-3), 5.98 (H-5), 5.32 (OH-4), and 13.99 (OH-6)
R2 group: δ 4.58 (H-1), 5.52 (H-2), 2.21 (H-4), 1.75 (H-5), 4.32 (H-6), 5.02 (H-8), 5.05 (H-8), and 1.75 (H-9 and H-10)
acyl group: δ 3.63 (H-1), 1.35 (H-2), 1.80 (H-2), 0.88 (H-3), and 1.11 (H-4)
13C NMR (125 MHz, CDCl3)
THB core: δ 105.9 (C-1), 162.4 (C-2), 91.7 (C-3), 162.0 (C-4), 96.6 (C-5), and 167.5 (C-6)
R2 group: δ 65.6 (C-1), 119.2 (C-2), 141.2 (C-3), 35.2 (C-4), 26.8 (C-5), 89.0 (C-6), 143.3 (C-7), 114.6 (C-8), 16.6 (C-9), and 17.2 (C-10)
acyl group: δ 210.3 (C-1’), 46.1 (C-1), 26.8 (C-2), 11.9 (C-3), and 16.6 (C-4)6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
Olympicin E (27)
C21H30O5
|
Hypericum olympicum
England6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
1H NMR (500 MHz, CDCl3)
THB core: δ 6.02 (H-3), 5.98 (H-5), 6.90 (OH-4), and 13.95 (OH-6)
R2 group: δ 4.67 (H-1), 5.50 (H-2), 2.30 (H-4), 1.65 (H-5), 1.90 (H-5), 2.77 (H-6), 1.31 (H-8), 1.76 (H-9), and 1.34 (H-10)
acyl group: δ 3.63 (H-1), 1.38 (H-2), 1.81 (H-2), 0.90 (H-3), and 1.10 (H-4)
13C NMR (125 MHz, CDCl3)
THB core: δ 105.5 (C-1), 162.3 (C-2), 92.7 (C-3), 162.8 (C-4), 96.8 (C-5), and 167.6 (C-6)
R2 group: δ 66.4 (C-1), 121.9 (C-2), 138.5 (C-3), 37.0 (C-4), 26.5 (C-5), 65.1 (C-6), 59.1 (C-7), 18.9 (C-8), 16.0 (C-9), and 24.6 (C-10)
acyl group: δ 210.0 (C-1’), 46.1 (C-1), 26.5 (C-2), 12.0 (C-3), and 16.6 (C-4)6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
Hyperjovinol A (28)
C20H30O5
|
Hypericum jovis
Greece4545 Athanasas, K; Magiatis, P.; Fokialakis, N.; Skaltsounis, A. L.; Pratsinis, H.; Kletsas, D.; J. Nat. Prod. 2004, 67, 973. [Crossref] Crossref...
,6262 Grafakou, M. E.; Barda, C; Pintać, D.; Lesjak, M.; Heilmann, J.; Skaltsa, H; Planta Med. 2021, 87, 1184. [Crossref] Crossref...
Garcinia dauphinensis
Madagascar6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
|
1H NMR (400 MHz, CDCl3)
THB core: δ 5.85 (H-3)
R5 group: δ 2.60 (H-1), 2.65 (H-1), 1.73 (H-2), 1.55 (H-4), 2.03 (H-5), 5.08 (H-6), 1.65 (H-8), 1.22 (H-9), and 1.58 (H-10)
acyl group: δ 3.90 (H-2) and 1.14 (H-3 and H-4)
13C NMR (50 MHz, CDCl3)
THB core: δ 104.1 (C-1), 159.6 (C-2), 95.4 (C-3), 160.6 (C-4), 108.7 (C-5), and 162.8 (C-6)
R5 group: δ 15.9 (C-1), 39.7 (C-2), 74.8 (C-3), 41.9 (C-4), 22.9 (C-5), 123.9 (C-6), 132.5 (C-7), 25.7 (C-8), 26.6 (C-9), and 17.6 (C-10)
acyl group: δ 210.9 (C-1’), 39.1 (C-1), and 19.3 (C-2 and C-3)4545 Athanasas, K; Magiatis, P.; Fokialakis, N.; Skaltsounis, A. L.; Pratsinis, H.; Kletsas, D.; J. Nat. Prod. 2004, 67, 973. [Crossref] Crossref...
|
Empetrikathiforin (29)
C21H30O5
|
Hypericum empetrifolium
Greece33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 5.86 (H-3), 7.73 (OH-2), 7.73 (OH-4), and 12.55 (OH-6)
R5 group: δ 2.69 (H-1), 3.11 (H-1), 4.35 (H-2), 2.45 (OH-2), 2.13 (H-4), 2.21 (H-4), 2.18 (H-5), 5.14 (H-6), 1.69 (H-8), 4.91 (H-9), 5.06 (H-9), and 1.62 (H-10)
acyl group: δ 3.77 (H-1), 1.40 (H-2), 1.83 (H-2), 0.91 (H-3), and 1.16 (H-4)
13C NMR (150 MHz, CDCl3)
THB core: δ 104.8 (C-1), 160.3 (C-2), 95.5 (C-3), 161.7 (C-4), 105.5 (C-5), and 163.5 (C-6)
R5 group: δ 29.1 (C-1), 77.3 (C-2), 151.0 (C-3), 32.1 (C-4), 26.4 (C-5), 123.7 (C-6), 132.2 (C-7), 25.6 (C-8), 109.2 (C-9), and 17.7 (C-10)
acyl group: δ 210.4 (C-1’), 45.9 (C-1), 26.9 (C-2), 11.9 (C-3), and 16.6 (C-4)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
|
1-Butanone-3-(3-methylbut-2-enylacetate)-phloroglucinol (30)
C17H22O6
|
Helichrysum niveum
South Africa4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
|
1H NMR (400 MHz, CD3COCD3)
THB core: δ 9.25 (OH-2), 9.66 (OH-4), and 14.0 (OH-6)
R5 group: δ 3.45 (H-1), 5.51 (H-2), 4.82 (H-4), 2.07 (H-6), and 1.71 (H-7)
acyl group: δ 3.08 (H-1), 1.71 (H-2), and 0.99 (H-3)
13C NMR (100 MHz, CD3COCD3)
THB core: δ 105.4 (C-1), 161.1 (C-2), 95.3 (C-3), 162.8 (C-4), 107.0 (C-5), and 165.4 (C-6)
R5 group: δ 22.1 (C-1), 129.6 (C-2), 130.4 (C-3), 64.0 (C-4), 171.5 (C-5), 21.1 (C-6), and 21.8 (C-7)
acyl group: δ 206.9 (C-1’), 46.8 (C-1), 19.2 (C-2), and 14.6 (C-3)4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
|
Dauphinol F (31)
C21H32O5
|
Garcinia dauphinensis
Madagascar6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
Hypericum jovis
Greece6262 Grafakou, M. E.; Barda, C; Pintać, D.; Lesjak, M.; Heilmann, J.; Skaltsa, H; Planta Med. 2021, 87, 1184. [Crossref] Crossref...
|
1H NMRd (CDCl3)
THB core: δ 5.84 (H-3), 7.54 (OH), and 12.46 (OH)
R5 group: δ 2.67 (H-1), 1.75 (H-2), 1.57 (H-4), 2.06 (H-5), 5.12 (H-6), 1.69 (H-8), 1.62 (H-9), and 1.24 (H-10)
acyl group: δ 3.77 (H-1), 1.83 (H-2), 1.39 (H-2), 0.91 (H-3), and 1.16 (H-4)
13C NMRd (CDCl3)
THB core: δ 95.8 (C-3)
R5 group: δ 15.9 (C-1), 39.9 (C-2), 74.9 (C-3), 42.1 (C-4), 23.1 (C-5), 124.0 (C-6), 132.9 (C-7), 17.9 (C-8), 26.9 (C-9), and 25.9 (C-10)
acyl group: δ 46.0 (C-1), 27.1 (C-2), 12.1 (C-3), and 16.9 (C-4)6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
|
Dauphinol E (32)
C26H40O5
|
Garcinia dauphinensis
Madagascar6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
|
1H NMRd (CDCl3)
THB core: δ 5.80 (H-3) and 1.64 (OH)
R5 group: δ 2.66 (H-1), 2.57 (H-1), 2.86 (H-2), 5.16 (H-4), 2.56 (H-5), 2.38 (H-5), 4.80 (H-6), 1.52 (H-8), 1.69 (H-9), 1.61 (H-10), 1.52 (H-1’), 1.35 (H-2’), 1.22 (H-4’), and 1.23 (H-5’)
acyl group: δ 3.72 (H-1), 1.82 (H-2), 1.39 (H-2), 0.90 (H-3), and 1.15 (H-4)
13C NMRd (CDCl3)
THB core: δ 106.7 (C-1), 160.0 (C-2), 95.4 (C-3), 160.0 (C-4), and 104.0 (C-5)
R5 group: δ 26.7 (C-1), 39.4 (C-2), 136.0 (C-3), 127.6 (C-4), 26.7 (C-5), 123.7 (C-6), 131.2 (C-7), 18.0 (C-8), 18.8 (C-9), 26.1 (C-10), 29.4 (C-1’), 40.8 (C-2’), 71.5 (C-3’), and 29.7 (C-4’ and C-5’)
acyl group: δ 210.3 (C-1’), 46.4 (C-1), 27.4 (C-2), 12.4 (C-3), and 16.9 (C-4)6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
|
Dauphinol C (33)
C26H38O4
|
Garcinia dauphinensis
Madagascar6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
|
1H NMRd (CDCl3)
THB core: δ 5.79 (H-3) and 5.33 (OH)
R5 group: δ 2.65 (H-1), 2.53 (H-1), 2.82 (H-2), 5.18 (H-4), 2.55 (H-5), 2.39 (H-5), 4.81 (H-6), 1.52 (H-8), 1.70 (H-9), 1.62 (H-10), 1.59 (H-1’), 1.92 (H-2’), 4.67 (H-4’), and 1.70 (H-5’)
acyl group: δ 3.71 (H-1), 1.82 (H-2), 1.38 (H-2), 0.91 (H-3), and 1.16 (H-4)
13C NMRd (CDCl3)
THB core: δ 104.7 (C-1), 159.3 (C-2), 95.2 (C-3), 160.2 (C-4), 106.9 (C-5), and 163.4 (C-6)
R5 group: δ 27.0 (C-1), 39.0 (C-2), 136.6 (C-3), 127.4 (C-4), 26.5 (C-5), 123.5 (C-6), 131.5 (C-7), 17.7 (C-8), 18.6 (C-9), 25.8 (C-10), 30.6 (C-1’), 35.9 (C-2’), 146.4 (C-3’), 109.8 (C-4’), and 22.6 (C-5’)
acyl group: δ 210.4 (C-1’), 46.2 (C-1), 27.1 (C-2), 12.1 (C-3), and 16.7 (C-4)6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
|
Dauphinol D (hyperannulatin B) (34)
C26H38O4
|
Garcinia dauphinensis
Madagascar6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
Hypericum annulatum
Rhodopi Mountain3535 Nedialkov, P. T.; Ilieva, Y.; Momekov, G.; Kokanova-Nedialkova, Z.; Fitoterapia 2018, 127, 375. [Crossref] Crossref...
|
1H NMRd (CDCl3)
THB core: δ 5.81 (H-3) and 5.28 (OH)
R5 group: δ 2.62 (H-1), 2.55 (H-1), 2.83 (H-2), 4.81 (H-4), 2.55 (H-5), 2.36 (H-5), 5.18 (H-6), 1.71 (H-8), 1.51 (H-9), 1.62 (H-10), 2.08 (H-1’), 2.17 (H-1’), 5.10 (H-2’), 1.63 (H-4’), and 1.71 (H-5’)
acyl group: δ 3.71 (H-1), 1.82 (H-2), 1.38 (H-2), 0.90 (H-3), and 1.15 (H-4)
13C NMRd (CDCl3)
THB core: δ 106.9 (C-1), 159.7 (C-2), 95.4 (C-3), 160.1 (C-4), 104.8 (C-5), and 162.8 (C-6)
R5 group: δ 26.3 (C-1), 40.2 (C-2), 137.0 (C-3), 127.0 (C-4), 26.5 (C-5), 123.4 (C-6), 131.5 (C-7), 17.7 (C-8), 18.7 (C-9), 25.8 (C-10), 31.3 (C-1’), 123.2 (C-2’), 133.1 (C-3’), 18.1 (C-4’), and 25.9 (C-5’)
acyl group: δ 210.4 (C-1’), 46.2 (C-1), 27.1 (C-2), 12.1 (C-3), and 16.7 (C-4)6666 Fuentes, R. G.; Pearce, K. C; Du, Y; Rakotondrafara, A.; Valenciano, A. L.; Cassera, M. B.; Rasamison, V. E.; Crawford, T. D.; Kingston, D. G. L; J. Nat. Prod. 2019, 82, 431. [Crossref] Crossref...
|
Caespitate (35)
C17H22O6
|
Helichrysum caespititium
South Africa99 Mathekga, A. D. M.; Meyer, J. J. M.; Horn, M. M.; Drewes, S. E.; Phytochemistry 2000, 53, 93. [Crossref] Crossref...
Helichrysum niveum
South Africa4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
|
1H NMR (400 MHz, CDCl3)
THB core: δ 5.88 (H-3), 8.23 (OH-4), and 12.88 (OH-6)
R5 group: δ 3.42 (H-1), 5.38 (H-2), 4.73 (H-4), 2.05 (H-6), and 1.70 (H-7)
acyl group: δ 3.89 (H-1), and 1.43 (H-2 and H-3)
13C NMR (100 MHz, CDCl3)
THB core: δ 104.0 (C-1), 159.4 (C-2), 95.3 (C-3), 160.7 (C-4), 105.8 (C-5), and 163.5 (C-6)
R5 group: δ 21.0 (C-1), 128.9 (C-2), 129.9 (C-3), 64.1 (C-4), 172.6 (C-5), 21.2 (C-6), and 21.1 (C-7)
acyl group: δ 210.8 (C-1’), 39.2 (C-1), and 19.3 (C-2 and C-3)4242 Popoola, O. K; Marnewick, J. L.; Rautenbach, F.; Iwuoha, E. I.; Hussein, A. A.; Molecules 2015, 20, 17309. [Crossref] Crossref...
|
6-Demethylacronylin (36)
C13H16O4
|
Acronychia laurifolia
c
7070 Banerji, J.; Rej, R. N.; Chatterjee, A.; Chem. Informationsdienst 1973, 4, 693. [Crossref] Crossref...
|
NMR data not found |
Caespitin (37)
C17H24O4
|
Helichrysum caespititium
South Africa7171 Dekker, T. G.; Fourie, T. G; Snyckers, F. O.; Schyf, V. D.; S. Afr. J. Chem. 1983, 36, 114. [Crossref] Crossref...
|
1H NMR (80 MHz, CDCl3/CD3OD) δ 13.33, 5.90, 5.25, 3.22, 3.02, 2.65-2.03, 1.73, 1.65, 1.58, and 0.88
13C NMRd (DMSO-d6) δ 163.4, 162.1, 159.8, 105.9, 103.6, 41.1, 33.7, 25.4, 22.3, 20.9, and 17.6
THB core: δ 103.6 (C-1 or C-3), 105.9 (C-1 or C-3), and 94.2 (C-5)
prenyl group: δ 123.5 (C-2) and 129.3 (C-3)
acyl group: δ 205.6 (C-1’) and 27.5 (C-3)7171 Dekker, T. G.; Fourie, T. G; Snyckers, F. O.; Schyf, V. D.; S. Afr. J. Chem. 1983, 36, 114. [Crossref] Crossref...
|
(2,4,6-Trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-onef (38)
C20H20O4
|
Helichrysum argyrolepis
South Africa7272 Bohlmann, F.; Misra, L. N.; Jakupovic, J.; Planta Med. 1984, 50, 174. [Crossref] Crossref...
|
NMR data not found
|
3’-(3,3-Dimethylallyl)-2’,4’,6’-trihydroxy-7,8-dihydrochalkon (39)
C20H22O4
|
Helichrysum argyrolepis
South Africa7272 Bohlmann, F.; Misra, L. N.; Jakupovic, J.; Planta Med. 1984, 50, 174. [Crossref] Crossref...
|
1H NMR (400 MHz, CDCl3)
THB core: δ 5.84 (H-5)
prenyl group: δ 3.35 (H-1), 5.23 (H-2), 1.82 (H-4), and 1.77 (H-5)
acyl group: δ 3.39 (H-1), 3.01 (H-2), and 7.25 (H-4 and H-8)7272 Bohlmann, F.; Misra, L. N.; Jakupovic, J.; Planta Med. 1984, 50, 174. [Crossref] Crossref...
|
1-(2’,4’-Dihydroxy-6’-(3”-methyl-2”-butenyloxy)-5’-(3”-methyl-2”-butenyl)) phenylethanone (40)
C18H24O4
|
Euodia lunu-ankenda
Sri Lanka7373 Kumar, V.; Karunaratne, V.; Sanath, M. R.; Meegalle, K; Macleod, J. K; Phytochemistry 1990, 29, 243. [Crossref] Crossref...
|
NMR data not found
|
Olympicin A (41)
C21H30O4
|
Hypericum olympicum
England6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
1H NMR (500 MHz, CDCl3)
THB core: δ 5.92 (H-3), 5.98 (H-5), 5.32 (OH-4), and 14.02 (OH-6)
geranyl group:a δ 4.57 (H-1), 5.51 (H-2), 2.13 (H-4), 2.10 (H-5), 5.10 (H-6), 1.62 (H-8), 1.74 (s, H-9), and 1.69 (H-10)
acyl group: δ 3.66 (H-1), 1.37 (H-2), 1.80 (H-2), 0.89 (H-3), and 1.12 (H-4)
13C NMR (125 MHz, CDCl3)
THB core: δ 105.0 (C-1), 162.6 (C-2), 91.5 (C-3), 161.9 (C-4), 96.5 (C-5), and 167.5 (C-6)
geranyl group:a δ 65.7 (C-1), 118.2 (C-2), 142.3 (C-3), 39.5 (C-4), 26.3 (C-5), 123.6 (C-6), 132.0 (C-7), 17.7 (C-8), 16.7 (C-9), and 25.7 (C-10)
acyl group: δ 210.4 (C-1’), 46.1 (C-1), 26.8 (C-2), 11.8 (C-3), and 16.6 (C-4)6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
Melicopol (42)
C19H26O6
|
Melicope broadbentiana
Australia3333 Ritchie, E.; Taylor, W. C.; Vautin, T. K.; Aust. J. Chem. 1965, 18, 2021. [Crossref] Crossref...
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1H NMR (D2O)
THB core: δ 4.71 (H-3), 3.90 (OH-3), 6.01 (H-5), 7.15 (OH), and 13.25 (OH)
geranyl group:a δ 4.53 (H-1), 5.50 (H-2 or H-6), 5.10 (H-2 or H-6), 2.12 (H-4 and H-5), 1.77 (H-8 and H-10), 1.67 (H-8 or H-10), and 1.62 (H-8 or H-10)
acyl group: δ 3.90 (CH3)33
|
1-[2’,4’-Dihydroxy-6’-(3”,7”-dimethylocta-2”,6”-dienyloxy)-5’-(3”-methyl-2”-butenyl)]phenylethanone (43)
C23H32O4
|
Euodia lunu-ankenda
Sri Lanka7373 Kumar, V.; Karunaratne, V.; Sanath, M. R.; Meegalle, K; Macleod, J. K; Phytochemistry 1990, 29, 243. [Crossref] Crossref...
|
NMR data not found
|
3-Farnesyl-2,4,6-trihydroxyacetophenone (44)
C23H32O4
|
Boronza ramose
Australia4848 Ahsan, M.; Gray, A. I..; Waterman; P. G; Armstrong, J. A.; J. Nat. Prod. 1994, 57, 673. [Crossref] Crossref...
|
1H NMR (400 MHz, CDCl3)
THB core: δ 5.88 (H-5)
R3 group: δ 3.37 (H-1), 5.26 (H-2), 1.94-2.16 (H-4, H-5, H-8, and H-9), 5.08 (H-6), 5.08 (H-10), 1.68 (H-12), 1.78 (H-13), 1.60 (H-14), and 1.60 (H-15)
acyl group: δ 2.68 (CH3)
13C NMR (100 MHz, CDCl3)
THB core: δ 105.4 (C-1), 160.7 (C-2), 105.7 (C-3), 161.6 (C-4), 95.5 (C-5), and 162.6 (C-6)
R3 group: δ 21.7 (C-1), 121.6 (C-2), 140.2 (C-3), 39.9 (C-4 and C-8), 26.5 (C-5), 123.7 (C-6), 135.9 (C-7), 26.9 (C-9), 124.5 (C-10), 131.5 (C-11), 25.9 (C-12), 16.5 (C-13), 16.3 (C-14), and 17.9 (C-15)
acyl group: δ 204.1 (C-1’) and 33.0 (CH3)4848 Ahsan, M.; Gray, A. I..; Waterman; P. G; Armstrong, J. A.; J. Nat. Prod. 1994, 57, 673. [Crossref] Crossref...
|
Olympicin B (45)
C21H30O5
|
Hypericum olympicum
England6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
1H NMR (500 MHz, CDCl3)
THB core: δ 5.90 (H-3), 5.99 (H-5), and 14.00 (OH-6)
R2 group: δ 4.58 (H-1), 5.30 (H-2), 2.81 (H-4), 5.68 (H-5), 5.66 (H-6), 1.35 (H-8 and H-10), and 1.74 (H-9)
acyl group: δ 3.63 (H-1), 1.37 (H-2), 1.80 (H-2), 0.88 (H-3), and 1.12 (H-4)
13C NMR (125 MHz, CDCl3)
THB core: δ 105.9 (C-1), 162.4 (C-2), 91.7 (C-3), 162.1 (C-4), 96.6 (C-5), and 167.5 (C-6)
R2 group: δ 65.6 (C-1), 119.6 (C-2), 140.5 (C-3), 42.2 (C-4), 128.4 (C-5), 135.9 (C-6), 82.2 (C-7), 24.3 (C-8 and C-10), and 16.8 (C-9)
acyl group: δ 210.3 (C-1’), 46.1 (C-1), 26.9 (C-2), 11.9 (C-3), and 16.7 (C-4)6969 Shiu, W. K. P.; Rahman, M. M.; Curry, J.; Stapleton, P.; Zloh, M.; Malkinson, J. P.; Gibbons, S.; J. Nat. Prod 2012, 75, 336. [Crossref] Crossref...
|
Hyperfaberol E (46)
C20H28O5
|
Hypericum faberi
China7474 Zhang, X. W.; Ye, Y. S.; Xia, F.; Yang, X W; Xu, G; Nat. Prod. Bioprospect. 2019, 9, 215. [Crossref] Crossref...
|
1H NMR (600 MHz, DMSO)
THB core: δ 5.90 (H-5), 13.90 (OH-2), 10.26 (OH-4), and 10.78 (OH-6)
R3 group: δ 2.66 (H-1), 2.53 (H-1), 4.14 (H-2), 2.03 (H-4), 2.02 (H-5), 5.06 (H-6), 1.59 (H-8), 4.61 (H-9), 4.78 (H-9), and 1.52 (H-10)
acyl group: δ 3.86 (H-1) and 1.02 (H-2 and H-3)
13C NMR (150 MHz, DMSO)
THB core: δ 102.8 (C-1), 164.1 (C-2), 104.2 (C-3), 163.0 (C-4), 94.5 (C-5), and 160.1 (C-6)
R3 group: δ 29.3 (C-1), 73.5 (C-2), 152.1 (C-3), 26.0 (C-4), 31.0 (C-5), 124.5 (C-6), 130.6 (C-7), 25.5 (C-8), 108.1 (C-9), and 17.5 (C-10)
acyl group: δ 209.5 (C-1’), 38.1 (C-1), and 19.3 (C-2 and C-3)7474 Zhang, X. W.; Ye, Y. S.; Xia, F.; Yang, X W; Xu, G; Nat. Prod. Bioprospect. 2019, 9, 215. [Crossref] Crossref...
|
Hyperfaberol C (47)
C21H32O6
|
Hypericum faberi
China7474 Zhang, X. W.; Ye, Y. S.; Xia, F.; Yang, X W; Xu, G; Nat. Prod. Bioprospect. 2019, 9, 215. [Crossref] Crossref...
|
1H NMR (600 MHz, DMSO)
THB core: δ 5.97 (H-5), 14.14 (OH-2), 10.26 (OH-4), and 10.51 (OH-6)
R3 group: δ 3.06 (H-1), 5.11 (H-2), 1.82 (H-4), 2.10 (H-4), 1.12 (H-5), 1.52 (H-5), 3.14 (H-6), 1.01 (H-8), 1.66 (H-9), 0.94 (H-10), and 3.03 (H-11)
acyl group: δ 3.89 (H-1) and 1.05 (H-2 and H-3)
13C NMR (150 MHz, DMSO)
THB core: δ 102.7 (C-1), 163.8 (C-2), 106.0 (C-3), 162.2 (C-4), 94.2 (C-5), and 159.6 (C-6)
R3 group: δ 20.9 (C-1), 122.7 (C-2), 133.8 (C-3), 36.4 (C-4), 29.2 (C-5), 74.4 (C-6), 76.8 (C-7), 21.6 (C-8), 16.1 (C-9), 19.6 (C-10), and 48.6 (C-11)
acyl group: δ 209.5 (C-1’), 38.0 (C-1), and 19.3 (C-2 and C-3)7474 Zhang, X. W.; Ye, Y. S.; Xia, F.; Yang, X W; Xu, G; Nat. Prod. Bioprospect. 2019, 9, 215. [Crossref] Crossref...
|
Iso-hyperjovinol-A (48)
C20H30O5
|
Hypericum jovis
Greece6262 Grafakou, M. E.; Barda, C; Pintać, D.; Lesjak, M.; Heilmann, J.; Skaltsa, H; Planta Med. 2021, 87, 1184. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 5.85 (H-5)
R3 group: δ 3.35 (H-1), 5.24 (H-2), 2.05 (H-4), 1.49 (H-5), 1.43 (H-6), 1.20 (H-8 and H-10), and 1.80 (H-9)
acyl group: δ 3.88 (H-1) and 1.16 (H-2 and H-3)
13C NMR (150 MHz, CDCl3)
THB core: δ 104.0 (C-1), 162.8 (C-2), 105.8 (C-3), 160.9 (C-4 and C-6), and 95.2 (C -5)
R3 group: δ 21.4 (C-1), 122.1 (C-2), 138.8 (C-3), 39.2 (C-4), 22.3 (C-5), 43.1 (C-6), 71.6 (C-7), 29.1 (C-8 and C-10), and 16.1 (C-9)
acyl group: δ 210.8 (C-1’), 39.8 (C-1), and 19.2 (C-2 and C-3)6262 Grafakou, M. E.; Barda, C; Pintać, D.; Lesjak, M.; Heilmann, J.; Skaltsa, H; Planta Med. 2021, 87, 1184. [Crossref] Crossref...
|
Hyperfaberol D (49)
C20H28O5
|
Hypericum faberi
China7474 Zhang, X. W.; Ye, Y. S.; Xia, F.; Yang, X W; Xu, G; Nat. Prod. Bioprospect. 2019, 9, 215. [Crossref] Crossref...
|
1H NMR (600 MHz, DMSO)
THB core: δ 5.98 (H-5), 14.13 (OH-2), 10.26 (OH-4), and 10.52 (OH-6)
R3 group: δ 3.07 (H-1), 5.09 (H-2), 1.82 (H-4), 1.89 (H-4), 1.42 (H-5), 3.78 (H-6), 1.59 (H-8), 1.66 (H-9), 4.67 (H-10), and 4.79 (H-11)
acyl group: δ 3.89 (H-1) and 1.05 (H-2 and H-3)
13C NMR (150 MHz, DMSO)
THB core: δ 102.6 (C-1), 163.8 (C-2), 105.9 (C-3), 162.2 (C-4), 94.2 (C-5), and 159.6 (C-6)
R3 group: δ 20.9 (C-1), 122.8 (C-2), 133.3 (C-3), 35.2 (C-4), 33.4 (C-5), 73.5 (C-6), 148.2 (C-7), 17.6 (C-8), 16.1 (C-9), and 109.8 (C-10)
acyl group: δ 209.5 (C-1’), 38.0 (C-1), and 19.3 (C-2 and C-3)7474 Zhang, X. W.; Ye, Y. S.; Xia, F.; Yang, X W; Xu, G; Nat. Prod. Bioprospect. 2019, 9, 215. [Crossref] Crossref...
|
3’-Methyl-isohyperjovinol A (50)
C21H32O5
|
Hypericum jovis
Greece6262 Grafakou, M. E.; Barda, C; Pintać, D.; Lesjak, M.; Heilmann, J.; Skaltsa, H; Planta Med. 2021, 87, 1184. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 5.84 (H-5)
R3 group: δ 3.37 (H-1), 5.26 (H-2), 2.05 (H-4), 1.49 (H-5), 1.43 (H-6), 1.20 (H-8 and H-10), and 1.81 (H-9)
acyl group: δ 3.73 (H-1), 1.84 (H-2), 1.40 (H-2), 0.91 (H-3), and 1.15 (H-4)
13C NMR (150 MHz, CDCl3)
THB core: δ 104.6 (C-1), 162.8 (C-2), 105.8 (C-3), 160.7 (C-4 and C-6), and 95.3 (C -5)
R3 group: δ 21.5 (C-1), 121.7 (C-2), 139.4 (C-3), 39.9 (C-4), 22.3 (C-5), 43.2 (C-6), 71.1 (C-7), 29.2 (C-8 and C-10), and 16.2 (C-9)
acyl group: δ 210.3 (C-1’), 45.9 (C-1), 26.9 (C-2), 11.9 (C-3), and 16.7 (C-4)6262 Grafakou, M. E.; Barda, C; Pintać, D.; Lesjak, M.; Heilmann, J.; Skaltsa, H; Planta Med. 2021, 87, 1184. [Crossref] Crossref...
|
Crassipetalonol A (51)
C18H24O5
|
Acronychia crassipetala
Australia7575 Tran, T. D.; Olsson, M. A.; McMillan, D. J.; Cullen, J. K; Parsons, P. G; Reddell, P. W; Ogbourne, S. M.; Antibiotics 2020, 9, 487. [Crossref] Crossref...
|
1H NMR (400 MHz, DMSO)
THB core: δ 6.06 (H-5), 13.45 (OH-2), and 10.97 (OH-6)
prenyl R3 group: δ 3.11 (H-1), 5.07 (H-2), 1.59 (H-4), and 1.67 (H-5)
prenyl R4 group: δ 4.52 (H-1), 5.40 (H-2), 1.70 (H-4), and 1.75 (H-5)
acyl group: δ 4.63 (CH2)
13C NMR (100 MHz, DMSO)
THB core: δ 102.4 (C-1), 161.5 (C-2), 107.0 (C-3), 162.5 (C-4), 91.3 (C-5), and 160.7 (C-6)
prenyl R3 group: δ 20.9 (C-1), 122.9 (C-2), 129.9 (C-3), 25.4 (C-4), and 17.5 (C-5)
prenyl R4 group: δ 64.6 (C-1), 119.2 (C-2), 137.8 (C-3), 18.0 (C-4), and 25.5 (C-5)
acyl group: δ 204.4 (C-1’) and 68.2 (CH2)7575 Tran, T. D.; Olsson, M. A.; McMillan, D. J.; Cullen, J. K; Parsons, P. G; Reddell, P. W; Ogbourne, S. M.; Antibiotics 2020, 9, 487. [Crossref] Crossref...
|
Crassipetalone A (52)
C18H24O4
|
Acronychia crassipetala
Australia7575 Tran, T. D.; Olsson, M. A.; McMillan, D. J.; Cullen, J. K; Parsons, P. G; Reddell, P. W; Ogbourne, S. M.; Antibiotics 2020, 9, 487. [Crossref] Crossref...
|
NMR data not found
|
Acronyculatin S (53)
C14H18O4
|
Mallotus oppositifolius
Cameroon7676 Tchangoue, Y. A. N.; Tchamgoue, J.; Lungae, P. K; Knepper, J.; Paltinean, R.; Ibrom, K; Crişan, G; Kouam, S. F; Ali, M. S.; Schulz, S.; Fitoterapia 2020, 42, 104527. [Crossref] Crossref...
|
1H NMR (600 MHz, DMSO)
THB core: δ 6.01 (H-5), 3.82 (OCH3-4), and 13.93 (OH-6)
prenyl group: δ 3.33 (H-1), 5.18 (H-2), 1.77 (H-4), and 1.83 (H-5)
acyl group: δ 2.66 (CH3)
13C NMR (150 MHz, DMSO)
THB core: δ 105.1 (C-1), 159.1 (C-2), 105.8 (C-3), 162.7 (C-4), 91.5 (C-5), and 165.6 (C-6)
prenyl group: δ 21.2 (C-1), 121.3 (C-2), 135.5 (C-3), 25.6 (C-4), and 17.7 (C-5)
acyl group: δ 203.3 (C-1’) and 32.7 (CH3)7676 Tchangoue, Y. A. N.; Tchamgoue, J.; Lungae, P. K; Knepper, J.; Paltinean, R.; Ibrom, K; Crişan, G; Kouam, S. F; Ali, M. S.; Schulz, S.; Fitoterapia 2020, 42, 104527. [Crossref] Crossref...
|
2,6-Dihydroxy-4-geranyloxy-3-prenylacetophenone (54)
C23H32O4
|
Evodia merrillii
Taiwan4646 Chou, C. J.; Lin, L C; Chen, K. T.; Chen, C. F; J. Nat. Prod. 1992, 55, 795. [Crossref] Crossref...
Melicope obtusifolia
Reunion Island4747 Adsersen, A.; Smitt, U. W; Simonsen, H. T.; Christensen, S. B.; Jaroszewski, J. W.; Biochem. Syst. Ecol. 2007, 35, 447. [Crossref] Crossref...
|
1H NMRb (300 MHz)
THB core: δ 5.98 (H-5), 8.41 (OH-2 or OH-6), and 11.64 (OH-2 or OH-6)
prenyl group: δ 3.31 (H-1), 5.17 (H-2), 1.79 (H-4), and 1.73 (H-5)
geranyl group:a δ 4.51 (H-1), 5.42 (H-2), 2.09 (H-4 and H-5), 5.07 (H-6), 1.58 (H-8), 1.69 (H-9), and 1.66 (H-10)
acyl group: δ 2.64 (CH3)
13C NMRb (75 MHz)
THB core: δ 105.3 (C-1), 159.7 (C-2), 106.5 (C-3), 163.0 (C-4), 92.8 (C-5), and 162.5 (C-6)
prenyl group: δ 21.6 (C-1), 121.9 (C-2), 134.9 (C-3), 25.8 (C-4), and 17.8 (C-5)
geranyl group:a: δ 65.4 (C-1), 118.9 (C-2), 141.5 (C-3), 39.5 (C-4), 26.3 (C-5), 123.7 (C-6), 131.9 (C-7), 17.7 (C-8), 16.7 (C-9), and 25.6 (C-10)
acyl group: δ 203.5 (C-1’) and 32.8 (CH3)4646 Chou, C. J.; Lin, L C; Chen, K. T.; Chen, C. F; J. Nat. Prod. 1992, 55, 795. [Crossref] Crossref...
|
Otogirin (55)
C21H30O4
|
Hypericum erectum
South Korea7777 Moon, H. L; Phytother. Res. 2010, 24, 941. [Crossref] Crossref...
Japan7878 Tada, M.; Chiba, K; Yamada, H.; Maruyama, H.; Phytochemistry 1991, 30, 2559. [Crossref] Crossref...
,7979 Lu, S.; Tanaka, N.; Tatano, Y.; Kashiwada, Y.; Fitoterapia 2016, 114, 188. [Crossref] Crossref...
Hypericum faberi
China7474 Zhang, X. W.; Ye, Y. S.; Xia, F.; Yang, X W; Xu, G; Nat. Prod. Bioprospect. 2019, 9, 215. [Crossref] Crossref...
|
1H NMR (270 MHz, CDCl3)
THB core: δ 9.80 (OH-2), 5.96 (H-5), 9.60 (OH-6), and 2.03 (CH3)
geranyl group:a δ 4.55 (H-1), 5.46 (H-2), 2.10 (H-4 and H-5), 5.09 (H-6), 1.68 (H-8), and 1.72 (H-9 and H-10)
acyl group: δ 3.90 (H-1) and 1.17 (H-2 and H-3)
13C NMR (67.89 MHz, CDCl3)
THB core: δ 104.4 (C-1), 160.9 (C-2), 103.8 (C-3), 162.5 (C-4), 92.6 (C-5), 159.9 (C-6), and 7.3 (CH3)
geranyl group:a δ 65.4 (C-1), 119.0 (C-2), 141.4 (C-3), 39.5 (C-4), 26.3 (C-5), 123.7 (C-6), 131.9 (C-7), 25.6 (C-8), 16.7 (C-9), and 17.6 (C-10)
acyl group: δ 210.5 (C-1’), 39.3 (C-1) and 19.3 (C-2 and C-3)7878 Tada, M.; Chiba, K; Yamada, H.; Maruyama, H.; Phytochemistry 1991, 30, 2559. [Crossref] Crossref...
|
4-Geranyloxy-3-prenyl-2,6,β-trihydroxyacetophenone (56)
C23H32O5
|
Evodia merrillii
Taiwan5656 Lin, L.-C; Chou, C.-J.; Chen, K. T.; Chen, C.-F; J. Nat. Prod. 1993, 56, 926. [Crossref] Crossref...
Melicope obtusifolia
Reunion Island4747 Adsersen, A.; Smitt, U. W; Simonsen, H. T.; Christensen, S. B.; Jaroszewski, J. W.; Biochem. Syst. Ecol. 2007, 35, 447. [Crossref] Crossref...
|
1H NMRd (CDCl3) δ 3.99 (OH), 8.80 (OH), and 11.03 (OH)
THB core: δ 6.01 (H-5)
prenyl group: δ 3.30 (H-1), 5.15 (H-2), 1.79 (H-4), and 1.73 (H-5)
geranyl group:a δ 4.53 (H-1), 5.42 (H-2), 2.08 (H-4 and H-5), 5.07 (H-6), 1.59 (H-8), 1.70 (H-9), and 1.66 (H-10)
acyl group: δ 4.78 (CH2)
13C NMRd (CDCl3)
THB core: δ 102.7 (C-1), 159.9 (C-2), 107.1 (C-3), 163.7 (C-4), 92.8 (C-5), and 162.8 (C-6)
prenyl group: δ 21.5 (C-1), 121.7 (C-2), 135.0 (C-3), 17.8 (C-4), and 25.8 (C-5)
geranyl group:a δ 65.6 (C-1), 118.7 (C-2), 141.8 (C-3), 39.4 (C-4), 26.3 (C-5), 123.7 (C-6), 131.9 (C-7), 17.7 (C-8), 16.7 (C-9), and 25.6 (C-10)
acyl group: δ 201.8 (C-1’) and 68.5 (CH2)5656 Lin, L.-C; Chou, C.-J.; Chen, K. T.; Chen, C.-F; J. Nat. Prod. 1993, 56, 926. [Crossref] Crossref...
|
Hyperannulatin A (57)
C25H36O4
|
Hypericum annulatum
Rhodopi Mountain3535 Nedialkov, P. T.; Ilieva, Y.; Momekov, G.; Kokanova-Nedialkova, Z.; Fitoterapia 2018, 127, 375. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 5.85 (H-5)
R3 group: δ 2.64 (H-1), 2.50 (H-1), 2.21 (H-2), 5.16 (H-4), 2.65 (H-5), 5.01 (H-6), 1.67 (H-8), 1.60 (H-9), 1.59 (H-10), 2.17 (H-1’), 2.11 (H-1’), 5.10 (H-2’), 1.69 (H-4’), and 1.60 (H-5’)
acyl group: δ 3.87 (H-1) and 1.17 (H-2 and H-3)
13C NMR (150 MHz, CDCl3)
THB core: δ 104.2 (C-1), 162.4 (C-2), 106.9 (C-3), 160.5 (C-4), and 95.4 (C-5)
R3 group: δ 27.7 (C-1), 48.5 (C-2), 139.0 (C-3), 124.9 (C-4), 27.0 (C-5), 122.9 (C-6), 131.8 (C-7), 25.8 (C-8), 14.6 (C-9), 17.8 (C-10), 32.2 (C-1’), 123.2 (C-2’), 133.2 (C-3’), 25.9 (C-4’), and 18.2 (C-5’)
acyl group: δ 210.8 (C-1’), 39.3 (C-1), and 19.5 (C-2 and C-3)3535 Nedialkov, P. T.; Ilieva, Y.; Momekov, G.; Kokanova-Nedialkova, Z.; Fitoterapia 2018, 127, 375. [Crossref] Crossref...
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1-(3,5-Dihydroxy-1-((3-methylbut-2-enyl) oxy)phenyl)-2-methyl-1-methylbutan-1-one (58)
C17H24O4
|
Hypericum calycinum
Switzerland4040 Decosterd, L. A.; Hoffmann, E.; Kyburz, R.; Bray, D.; Hostettmann, K; Planta Med. 1991, 57, 548. [Crossref] Crossref...
|
1H NMR (200 MHz, CDCl3)
THB core: δ 5.96 (H-3), 2.01 (H-5), 10.30, and 9.82
prenyl group: δ 4.5 (H-1), 5.44 (H-2), 1.79 (H-4 or H-5), and 1.71 (H-4 or H-5); acyl group: δ 2.97 (H-1), 2.26 (H-2), and 0.97 (H-3 and H-4)
13C NMR (50 MHz, CDCl3)
THB core: δ 103.8 (C-1), 160.2 (C-2), 92.3 (C-3), 162.7 (C-4), 104.7 (C-5), 160.9 (C-6), and 7.2 (CH3-5)
prenyl group: δ 65.3 (C-1), 119.1 (C-2), 138.3 (C-3), 25.7 (C-4), and 18.2 (C-5); acyl group: δ 206.2 (C-1’), 52.9 (C-1), 25.4 (C-2), and 22.8 (C-3 and C-4)4040 Decosterd, L. A.; Hoffmann, E.; Kyburz, R.; Bray, D.; Hostettmann, K; Planta Med. 1991, 57, 548. [Crossref] Crossref...
|
Adotogirin (59)
C22H32O4
|
Hypericum erectum
Japan7979 Lu, S.; Tanaka, N.; Tatano, Y.; Kashiwada, Y.; Fitoterapia 2016, 114, 188. [Crossref] Crossref...
|
1H NMR (500 MHz, CDCl3)
THB core: δ 5.96 (H-3) and 2.02 (CH3-5)
geranyl group:a δ 4.52 (H-1), 5.44 (H-2), 2.08 (H-4), 2.12 (H-5), 5.08 (H-6), 1.60 (H-8), 1.71 (H-9), and 1.67 (H-10)
acyl group: δ 3.77 (H-1), 1.84 (H-2), 1.41 (H-2), 0.91 (H-3), and 1.16 (H-4)
13C NMR (125 MHz, CDCl3)
THB core: δ 104.3 (C-1), 160.8 (C-2), 92.5 (C-3), 162.5 (C-4), 103.9 (C-5), 160.2 (C-6), and 7.2 (CH3-5)
geranyl group:a δ 65.3 (C-1), 118.9 (C-2), 141.4 (C-3), 39.4 (C-4), 26.2 (C-5), 123.6 (C-6), 131.9 (C-7), 17.7 (C-8), 16.7 (C-9), and 25.6 (C-10)
acyl group: δ 210.4 (C-1’), 45.9 (C-1), 27.0 (C-2), 11.9 (C-3), and 16.7 (C-4)7979 Lu, S.; Tanaka, N.; Tatano, Y.; Kashiwada, Y.; Fitoterapia 2016, 114, 188. [Crossref] Crossref...
|
Empetrifelixin D (60)
C31H46O4
|
Hypericum empetrifolium
Greece33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 6.20 (H-3), 12.12 (OH-2), and 7.61 (OH-6)
geranyl group:a δ 3.34 (H-1), 5.16 (H-2), 2.08 (H-4), 2.11 (H-5), 5.06 (H-6), 1.67 (H-8), 1.81 (H-9), and 1.60 (H-10)
R4 group: δ 2.04 (H-2), 1.38 (H-3), 1.89 (H-3), 2.01 (H-4), 5.38 (H-6), 1.91 (H-7), 2.07 (H-7), 1.42 (H-8), 1.39 (H-9), and 1.65 (H-10)
acyl group: δ 3.74 (H-1), 1.40 (H-2), 1.82 (H-2), 0.90 (H-3), and 1.14 (H-4)
13C NMR (150 MHz, CDCl3)
THB core: δ 109.8 (C-1), 162.5 (C-2), 99.5 (C-3), 160.1 (C-4), 105.3 (C-5), and 159.1 (C-6)
geranyl group:a δ 22.4 (C-1), 121.9 (C-2), 139.2 (C-3), 39.6 (C-4), 26.3 (C-5), 123.6 (C-6), 131.9 (C-7), 25.6 (C-8), 16.2 (C-9), and 17.6 (C-10)
R4 group: δ 84.8 (C-1), 44.1 (C-2), 24.2 (C-3), 30.9 (C-4), 134.0 (C-5), 120.4 (C-6), 26.6 (C-7), 24.1 (C-8), 24.2 (C-9), and 23.3 (C-10)
acyl group: δ 210.4 (C-1’), 45.9 (C-1), 26.8 (C-2), 11.9 (C-3), and 16.7 (C-4)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
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Empetrifelixin C (61)
C30H44O4
|
Hypericum empetrifolium
Greece33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 6.21 (H-3), 12.14 (OH-2), and 7.57 (OH-6)
geranyl group:a δ 3.34 (H-1), 5.16 (H-2), 2.07 (H-4), 2.11 (H-5), 5.05 (H-6), 1.67 (H-8), 1.81 (H-9), and 1.59 (H-10)
R4 group: δ 2.04 (H-2), 1.37 (H-3), 1.88 (H-3), 2.00 (H-4), 5.38 (H-6), 1.91 (H-7), 2.07 (H-7), 1.42 (H-8), 1.39 (H-9), and 1.65 (H-10)
acyl group: δ 3.88 (H-1) and 1.16 (H-2 and H-3)
13C NMR (150 MHz, CDCl3)
THB core: δ 109.8 (C-1), 162.6 (C-2), 99.5 (C-3), 160.1 (C-4), 104.8 (C-5), and 159.0 (C-6)
geranyl group:a δ 22.4 (C-1), 121.9 (C-2), 139.3 (C-3), 39.6 (C-4), 26.3 (C-5), 123.6 (C-6), 131.9 (C-7), 25.6 (C-8), 16.2 (C-9), and 17.6 (C-10)
R4 group: δ 84.8 (C-1), 44.1 (C-2), 24.2 (C-3), 30.9 (C-4), 134.0 (C-5), 120.4 (C-6), 26.6 (C-7), 24.1 (C-8), 24.3 (C-9), and 23.3 (C-10)
acyl group: δ 210.6 (C-1’), 39.2 (C-1), and 19.2 (C-3 and C-4)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
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Prereminol (62)
C14H18O4
|
Remirea maritima
c
4949 Allan, R. D.; Wells, R. J.; Macleod, J. K; Tetrahedron Lett. 1970, 11, 3945. [Crossref] Crossref...
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1H NMR (100 MHz, C5D5N): δ 8.30, 8.10, 7.43, 6.40, 6.33, 4.35, 3.85, 0.2, and -4.74949 Allan, R. D.; Wells, R. J.; Macleod, J. K; Tetrahedron Lett. 1970, 11, 3945. [Crossref] Crossref...
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Empetrifelixin A (63)
C30H44O4
|
Hypericum empetrifolium
Greece33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 6.06 (H-3), 6.04 (OH-4), and 13.91 (OH-6)
geranyl group:a δ 3.38 (H-1), 5.28 (H-2), 2.07 (H-4), 2.10 (H-5), 5.05 (H-6), 1.67 (H-8), 1.80 (H-9), and 1.59 (H-10)
R2 group: δ 2.25 (H-2), 1.35 (H-3), 1.86 (H-3), 1.99 (H-4), 5.37 (H-6), 1.89 (H-7), 2.01 (H-7), 1.45 (H-8), 1.38 (H-9), and 1.65 (H-10)
acyl group: δ 3.95 (H-1) and 1.17 (H-2 and H-3)
13C NMR (150 MHz, CDCl3)
THB core: δ 107.7 (C-1), 157.6 (C-2), 98.0 (C-3), 160.6 (C-4), 106.3 (C-5), and 163.9 (C-6)
geranyl group:a δ 21.6 (C-1), 121.7 (C-2), 139.5 (C-3), 39.6 (C-4), 26.3 (C-5), 123.6 (C-6), 132.0 (C-7), 25.6 (C-8), 16.2 (C-9), and 17.7 (C-10)
R2 group: δ 86.1 (C-1), 42.6 (C-2), 24.5 (C-3), 30.9 (C-4), 134.1 (C-5), 120.2 (C-6), 26.8 (C-7), 23.9 (C-8), 24.3 (C-9), and 23.3 (C-10)
acyl group: δ 211.4 (C-1’), 38.8 (C-1), 19.5 (C-2), and 19.6 (C-3)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
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Empetrifelixin B (64)
C31H46O4
|
Hypericum empetrifolium
Greece33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
|
1H NMR (600 MHz, CDCl3)
THB core: δ 6.06 (H-3 and OH-4), and 13.92 (OH-6)
geranyl group:a δ 3.38 (H-1), 5.29 (H-2), 2.07 (H-4), 2.10 (H-5), 5.05 (H-6), 1.67 (H-8), 1.82 (H-9), and 1.59 (H-10)
R2 group: δ 2.25 (H-2), 1.35 (H-3), 1.86 (H-3), 1.98 (H-4), 5.37 (H-6), 1.88 (H-7), 2.01 (H-7), 1.44 (H-8), 1.38 (H-9), and 1.65 (H-10)
acyl group: δ 3.87 (H-1), 1.42 (H-2), 1.75 (H-2), 0.85 (H-3), and 1.12 (H-4)
13C NMR (150 MHz, CDCl3)
THB core: δ 108.4 (C-1), 157.6 (C-2), 98.1 (C-3), 160.5 (C-4), 106.3 (C-5), and 163.7 (C-6)
geranyl group:a δ 21.6 (C-1), 121.7 (C-2), 139.5 (C-3), 39.6 (C-4), 26.3 (C-5), 123.6 (C-6), 132.0 (C-7), 25.6 (C-8), 16.1 (C-9), and 17.7 (C-10)
R2 group: δ 86.1 (C-1), 42.5 (C-2), 24.4 (C-3), 30.8 (C-4), 134.0 (C-5), 120.2 (C-6), 26.8 (C-7), 24.0 (C-8), 24.4 (C-9), and 23.3 (C-10)
acyl group: δ 211.3 (C-1’), 45.3 (C-1), 26.9 (C-2), 11.7 (C-3), and 17.0 (C-4)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
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Prenylacronylin (65)
C19H26O4
|
Acronychia pedunculata
Sri Lanka5050 Kumar, V.; Karunaratne, V.; Sanath, M. R.; Meegalle, K; Phytochemistry 1989, 28, 1278. [Crossref] Crossref...
,8080 Han, X.; Pathmasiri, W.; Bohlin, L.; Janson, J. C.; J. Chromatogr. A 2004, 1022, 213. [Crossref] Crossref...
,8181 Pathmasiri, W.; El-Seedi, H. R.; Han, X.; Janson, J. C; Huss, U.; Bohlin, L.; Chem. Biodiversity 2005, 2, 463. [Crossref] Crossref...
China8282 Sy, L. K.; Brown, G. D.; Phytochemistry 1999, 52, 681. [Crossref] Crossref...
Thailand8383 Kozaki, S.; Takenaka, Y.; Mizushina,Y;Yamaura, T.; Tanahashi, T.; J. Nat. Med. 2014, 68, 421. [Crossref] Crossref...
Taiwan5151 Ito, C; Hosono, M.; Tokuda, H; Wu, T. S.; Itoigawa, M.; Nat. Prod. Commun. 2016, 11, 1299. [Crossref] Crossref...
Indonesia8484 Tanjung, M.; Nurmalasari, L; Wilujeng, A. K.; Saputri, R. D.; Rachmadiarti, F.; Tjahjandarie, T. S.; Nat. Prod. Sci. 2018, 24, 284. [Crossref] Crossref...
Euodia lunu-ankenda
Sri Lanka7373 Kumar, V.; Karunaratne, V.; Sanath, M. R.; Meegalle, K; Macleod, J. K; Phytochemistry 1990, 29, 243. [Crossref] Crossref...
Acronychia trifoliolata
Indonesia5353 Miyake, K; Suzuki, A.; Morita, C; Goto, M.; Newman, D. J.; O'Keefe, B. R.; Morris-Natschke, S. L.; Lee, K H.; Goto, K. N.; J. Nat. Prod. 2016, 79, 2883. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 3.70 (H-2), 6.26 (OH-4), and 13.58 (OH-6)
prenyl R3 group: δ 3.37 (H-1), 5.21 (H-2), 1.75 (H-4), and 1.81 (H-5)
prenyl R5 group: δ 3.34 (H-1), 5.21 (H-2), 1.74 (H-4), and 1.81 (H-5)
acyl group: δ 2.68 (CH3)
13C NMR (100 MHz, CDCl3)
THB core: δ 108.98 (C-1), 159.16 (C-2), 112.65 (C-3), 160.67 (C-4), 110.98 (C-5), 161.61 (C-6), and 62.81 (OCH3)
prenyl R3 group: δ 21.82 (C-1), 122.26 (C-2), 134.66 (C-3), 25.81 (C-4), and 17.90 (C-5)
prenyl R5 group: δ 22.77 (C-1), 121.67 (C-2), 134.51 (C-3), 25.85 (C-4), and 17.98 (C-5)
acyl group: δ 203.60 (C-1’) and 31.1 (CH3)8080 Han, X.; Pathmasiri, W.; Bohlin, L.; Janson, J. C.; J. Chromatogr. A 2004, 1022, 213. [Crossref] Crossref...
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Laricifolin B (66)
C21H30O4
|
Hypericum laricifolium
Peru8585 Ccana-Ccapatinta, G. V.; Poser, G. L.; Phytochem. Lett. 2015, 12, 63. [Crossref] Crossref...
|
1H NMR (400 MHz, CDCl3)
THB core: δ 5.90 (H-3), 6.15 (OH-4), and 14.40 (OH-6)
prenyl R2 group: δ 4.51 (H-1), 5.48 (H-2), 1.76 (H-4), and 1.86 (H-5)
prenyl R5 group: δ 3.37 (H-1), 5.27 (H-2), 1.73 (H-4), and 1.80 (H-5)
acyl group: δ 3.66 (H-1), 1.35 (H-2), 0.88 (H-3), and 1.11 (H-4)
13C NMR (100 MHz, CDCl3)
THB core: δ 105.5 (C-1), 160.4 (C-2), 91.5 (C-3), 161.3 (C-4), 106.0 (C-5), and 164.7 (C-6)
prenyl R2 group: δ 65.3 (C-1), 118.6 (C-2), 138.5 (C-3), 18.1 (C-4), and 25.7 (C-5)
prenyl R5 group: δ 21.6 (C-1), 121.9 (C-2), 135.6 (C-3), 17.9 (C-4), and 25.8 (C-5)
acyl group: δ 210.5 (C-1’), 46.1 (C-1), 26.9 (C-2), 11.8 (C-3), and 16.5 (C-4)8585 Ccana-Ccapatinta, G. V.; Poser, G. L.; Phytochem. Lett. 2015, 12, 63. [Crossref] Crossref...
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Laricifolin A (67)
C20H28O4
|
Hypericum laricifolium
Peru8585 Ccana-Ccapatinta, G. V.; Poser, G. L.; Phytochem. Lett. 2015, 12, 63. [Crossref] Crossref...
|
1H NMR (400 MHz, CDCl3)
THB core: δ 5.90 (H-3), 6.15 (OH-4), and 14.45 (OH-6)
prenyl R2 group: δ 4.51 (H-1), 5.48 (H-2), 1.76 (H-4), and 1.86 (H-5)
prenyl R5 group: δ 3.37 (H-1), 5.27 (H-2), 1.73 (H-4), and 1.80 (H-5)
acyl group: δ 3.80 (H-1) and 1.14 (H-2 and H-3)
13C NMR (100 MHz, CDCl3)
THB core: δ 105.5 (C-1), 160.5 (C-2), 91.5 (C-3), 161.3 (C-4), 106.0 (C-5), and 164.7 (C-6)
prenyl R2 group: δ 65.4 (C-1), 118.7 (C-2), 138.7 (C-3), 18.2 (C-4), and 25.7 (C-5)
prenyl R5 group: δ 21.6 (C-1), 121.9 (C-2), 135.6 (C-3), 17.9 (C-4), and 25.8 (C-5)
acyl group: δ 210.6 (C-1’), 39.4 (C-1), and 19.4 (C-2 and C-3)8585 Ccana-Ccapatinta, G. V.; Poser, G. L.; Phytochem. Lett. 2015, 12, 63. [Crossref] Crossref...
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2,4,6-Trihydroxy-1-(2’-methyl-butanoyl)-3-(2’’,3’’-epoxy-3’’-methyl-butyl)-5-(3’”-methyl-2’”-butenyl)-benzene (68)
C21H30O5
|
Hypericum foliosum
England8686 Gibbons, S.; Moser, E.; Hausmann, S.; Stavri, M.; Smith, E.; Clennett, C; Phytochem. 2005, 66, 1472. [Crossref] Crossref...
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1H NMR (500 MHz, CDCl3)
THB core: δ 14.25 (H-2 or H-6) and 14.26 (H-2 or H-6)
prenyl group: δ 3.40 (H-1), 5.28 (H-2), 1.79 (H-4), and 1.84 (H-5)
R3 group: δ 2.61 (H-1), 2.86 (H-1), 3.81 (H-2), 1.39 (H-4), and 1.42 (H-5)
acyl group: δ 3.74 (H-1), 1.43 (H-2), 1.85 (H-2), 0.91 (H-3), and 1.17 (H-4)
13C NMR (125 MHz, CDCl3)
THB core: δ 105.6 (C-1), 153.9 (C-2 or C-6), 163.0 (C-2 or C-6), 160.0 (C-4), 105.7 (C-3 or C-5), and 97.8 (C-3 or C-5)
prenyl group: δ 21.9 (C-1), 122.1 (C-2), 136.5 (C-3), 26.1 (C-4), and 18.1 (C-5)
R3 group: δ 26.2 (C-1), 68.9 (C-2), 78.3 (C-3), 24.9 (C-4), and 22.1 (C-5)
acyl group: δ 210.7 (C-1’), 46.4 (C-1), 27.1 (C-2), 12.1 (C-3), and 17.0 (C-4)8686 Gibbons, S.; Moser, E.; Hausmann, S.; Stavri, M.; Smith, E.; Clennett, C; Phytochem. 2005, 66, 1472. [Crossref] Crossref...
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4,6-Dihydroxy-1-ethanoyl-2-methoxy-3-(3”-methyl-but-2”-enyl)-5-(3’’’-methyl-2’’’-butanoyl)-benzene (69)
C19H26O5
|
Acronychia oligophlebia
China8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 3.73 (OCH3-2), 8.64 (OH-4), and 13.74 (OH-6)
prenyl group: δ 3.34 (H-1), 5.22 (H-2), 1.79 (H-4), and 1.72 (H-5)
R5 group: δ 3.82 (H-1), 2.84 (H-3), and 1.17 (H-4 and H-5)
acyl group: δ 2.68 (CH3)
13C NMR (100 MHz, CDCl3)
THB core: δ 109.2 (C-1), 160.6 (C-2), 114.8 (C-3), 162.4 (C-4), 105.5 (C-5), 161.5 (C-6), and 62.9 (OCH3)
prenyl group: δ 23.1 (C-1), 122.8 (C-2), 133.4 (C-3), 18.1 (C-4), and 25.9 (C-5)
R5 group: δ 34.7 (C-1), 217.8 (C-2), 41.7 (C-3), and 17.9 (C-4 and C-5)
acyl group: δ 203.8 (C-1’) and 31.1 (CH3)8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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Acronyculatin R (70)
C19H26O5
|
Acronychia oligophlebia
China8888 Niu, Q.-W.; Chen, N.-H; Wu, Z.-N.; Luo, D.; Li, Y-Y; Zhang, Y.-B.; Li, Q.-G.; Li, Y-L; Wang, G.-C; Nat. Prod. Res. 2018, 33, 2230. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 3.72 (OCH3-2), 13.69 (OH-6), and 8.91 (OH-4)
R5 group: δ 2.75 (H-1), 3.15 (H-1), 4.33 (H-2), 5.01 (H-4), 4.87 (H-4), and 1.85 (H-5)
prenyl group: δ 3.33 (H-1), 5.21 (H-2), 1.70 (H-4), and 1.78 (H-5)
acyl group: δ 2.69 (CH3)
13C NMR (100 MHz, CDCl3)
THB core: δ 108.9 (C-1), 160.1 (C-2), 115.0 (C-3), 162.4 (C-4), 109.5 (C-5), 162.1 (C-6), and 62.8 (OCH3-2)
R5 group: δ 29.0 (C-1), 77.8 (C-2), 147.2 (C-3), 110.5 (C-4), and 18.6 (C-5)
prenyl group: δ 23.1 (C-1), 123.3 (C-2), 132.2 (C-3), 25.9 (C-4), and 18.1 (C-5)
acyl group: δ 203.7 (C-1’) and 31.2 (CH3)8888 Niu, Q.-W.; Chen, N.-H; Wu, Z.-N.; Luo, D.; Li, Y-Y; Zhang, Y.-B.; Li, Q.-G.; Li, Y-L; Wang, G.-C; Nat. Prod. Res. 2018, 33, 2230. [Crossref] Crossref...
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4,6-Dihydroxy-1-ethanoyl-2-methoxy-3-(3”-methyl-but-2”-enyl)-5-(3’’-methyl-but-1”-enyl)-benzene (71)
C19H26O4
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Acronychia oligophlebia
China8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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1H NMR (300 MHz, CD3OD)
THB core: δ 3.73 (OCH3-2)
prenyl group: δ 3.34 (H-1), 5.21 (H-2), 1.80 (H-4), and 1.71 (H-5)
R3 group: δ 6.36 (H-1), 6.35 (H-2), 2.47 (H-3), and 1.12 (H-4 and H-5)
acyl group: δ 2.69 (CH3)
13C NMR (75 MHz, CD3OD)
THB core: δ 109.6 (C-1), 161.1 (C-2), 111.1 (C-3), 162.8 (C-4), 115.7 (C-5), 161.3 (C-6), and 63.4 (OCH3-2)
prenyl group: δ 23.6 (C-1), 124.4 (C-2), 132.5 (C-3), 18.0 (C-4), and 25.9 (C-5)
R3 group: δ 117.8 (C-1), 143.8 (C-2), 33.9 (C-3), and 23.0 (C-4 and C-5)
acyl group: δ 205.7 (C-1’) and 31.3 (CH3)8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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Acronyculatin F (72)
C19H28O4
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Acronychia pedunculata
Thailand8383 Kozaki, S.; Takenaka, Y.; Mizushina,Y;Yamaura, T.; Tanahashi, T.; J. Nat. Med. 2014, 68, 421. [Crossref] Crossref...
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1H NMR (500 MHz, CDCl3)
THB core: δ 3.70 (OCH3-2), 5.95 (OH-4), and 13.47 (OH-6)
prenyl group: δ 3.38 (H-1), 5.22 (H-2), 1.79 (H-4), and 1.85 (H-5)
R5 group: δ 2.57 (H-1), 2.60 (H-1), 1.37 (H-2), 1.38 (H-2), 1.61 (H-3), and 0.95 (H-4 and H-5)
acyl group: δ 2.68 (CH3)
13C NMR (125 MHz, CDCl3)
THB core: δ 109.0 (C-1), 158.7 (C-2), 111.5 (C-3), 160.1 (C-4), 113.6 (C-5), and 162.1 (C-6)
prenyl group: δ 22.9 (C-1), 121.8 (C-2), 136.3 (C-3), 25.9 (C-4), and 18.0 (C-5)
R5 group: δ 20.7 (C-1), 37.9 (C-2), 28.4 (C-3), and 22.6 (C-4 and C-5)
acyl group: δ 203.6 (C-1’) and 31.2 (CH3)8383 Kozaki, S.; Takenaka, Y.; Mizushina,Y;Yamaura, T.; Tanahashi, T.; J. Nat. Med. 2014, 68, 421. [Crossref] Crossref...
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1-(4,6-Dihydroxy-1-ethanoyl-2-methoxy-3-(3’’-hydroxy-3’’-methyl-but-1”-enoyl)-5-(3”- methyl-but-2”-enyl))benzene (73)
C19H26O5
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Acronychia oligophlebia
China8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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1H NMR (300 MHz, CDCl3)
THB core: δ 3.76 (OCH3-2) and 13.74 (OH-6)
prenyl group: δ 3.28 (H-1), 5.22 (H-2), 1.79 (H-4), and 1.67 (H-5)
R3 group: δ 5.60 (H-1), 6.50 (H-2), and 1.44 (H-4 and H-5)
acyl group: δ 2.68 (CH3)
13C NMR (75 MHz, CDCl3)
THB core: δ 108.8 (C-1), 157.0 (C-2), 107.0 (C-3), 163.6 (C-4), 113.3 (C-5), 158.1 (C-6), and 63.2 (OCH3-2)
prenyl group: δ 21.6 (C-1), 122.3 (C-2), 131.5 (C-3), 18.0 (C-4), and 26.0 (C-5)
R3 group: δ 128.1 (C-1), 116.9 (C-2), 77.4 (C-3), and 28.3 (C-4 and C-5)
acyl group: δ 203.3 (C-1’) and 31.4 (CH3)8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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Empetrikajaforin (74)
C31H46O4
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Hypericum empetrifolium
Greece33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
1H NMR (600 MHz, CDCl3)
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THB core: δ 5.75 (H-3), 6.11 (OH-4), and 14.57 (OH-6)
geranyl group:a δ 3.38 (H-1), 5.28 (H-2), 2.08 (H-4), 2.10 (H-5), 5.05 (H-6), 1.67 (H-8), 1.81 (H-9), and 1.59 (H-10)
R2 group: δ 4.38 (H-1), 1.12 (H-2), 2.45 (H-2), 1.77 (H-3), 1.25 (H-4), 1.80 (H-4), 1.42 (H-5) 2.10 (H-5), 0.96 (H-8 and H-10), and 0.92 (H-9)
acyl group: δ 3.96 (H-1), 1.46 (H-2), 1.80 (H-2), 0.87 (H-3), and 1.17 (H-4)
13C NMR (150 MHz, CDCl3)
THB core: δ 105.5 (C-1), 160.7 (C-2), 92.9 (C-3), 161.5 (C-4), 105.7 (C-5), and 164.9 (C-6)
geranyl group:a δ 21.5 (C-1), 121.7 (C-2), 139.6 (C-3), 39.7 (C-4), 26.3 (C-5), 123.6 (C-6), 132.0 (C-7), 25.6 (C-8), 16.2 (C-9), and 17.7 (C-10) R2 group: δ 85.5 (C-1), 37.3 (C-2), 44.7 (C-3), 27.9 (C-4), 27.3 (C-5), 49.5 (C-6), 47.7 (C-7), 19.0 (C-8), 19.7 (C-9), and 14.0 (C-10)
acyl group: δ 210.6 (C-1’), 45.5 (C-1), 26.4 (C-2), 11.7 (C-3), and 17.8 (C-4)33 Schmidt, S.; Jürgenliemk, G.; Skaltsa, H.; Heilmann, J.; Phytochemistry 2012, 77, 218. [Crossref] Crossref...
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Acronyculatin Q (75)
C20H30O5
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Acronychia oligophlebia
China8888 Niu, Q.-W.; Chen, N.-H; Wu, Z.-N.; Luo, D.; Li, Y-Y; Zhang, Y.-B.; Li, Q.-G.; Li, Y-L; Wang, G.-C; Nat. Prod. Res. 2018, 33, 2230. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 3.73 (OCH3-2), 13.59 (OH-6), and 9.54 (OH-4)
R5 group: δ 4.92 (H-1), 1.81 (H-2), 1.43 (H-2), 1.83 (H-3), 0.95 (H-4), 0.96 (H-5), and 3.39 (H-6)
prenyl group: δ 3.28 (H-1), 5.21 (H-2), 1.70 (H-4), and 1.77 (H-5)
acyl group: δ 2.68 (CH3). 13C NMR (100 MHz, CDCl3)
THB core: δ 108.5 (C-1), 160.8 (C-2), 108.9 (C-3), 162.2 (C-4), 114.9 (C-5), 161.3 (C-6), and 62.8 (OCH3-2)
R5 group: δ 78.2 (C-1), 44.3 (C-2), 24.9 (C-3), 21.9 (C-4), 23.5 (C-5), and 57.8 (C-6)
prenyl group: δ 22.5 (C-1), 123.4 (C-2), 131.6 (C-3), 25.8 (C-4), and 18.0 (C-5)
acyl group: δ 203.7 (C-1’) and 31.1 (CH3)8888 Niu, Q.-W.; Chen, N.-H; Wu, Z.-N.; Luo, D.; Li, Y-Y; Zhang, Y.-B.; Li, Q.-G.; Li, Y-L; Wang, G.-C; Nat. Prod. Res. 2018, 33, 2230. [Crossref] Crossref...
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4,6-Dihydroxy-1-ethanoyl-2-methoxy-3-(3”-methyl-but-2”-enyl)-5-(3’”-hydroxy-3’’’-methyl-but-1”’-enyl)-benzene (76)
C19H26O5
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Acronychia oligophlebia
China8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 3.72 (OCH3-2) and 13.51 (OH-6)
prenyl group: δ 3.24 (H-1), 5.15 (H-2), 1.78 (H-4), and 1.69 (H-5)
R5 group: δ 5.50 (H-1), 6.67 (H-2), and 1.43 (H-4 and H-5)
acyl group: δ 2.67 (CH3)
13C NMR (100 MHz, CDCl3)
THB core: δ 109.1 (C-1), 161.1 (C-2), 115.0 (C-3), 158.7 (C-4), 106.1 (C-5), 159.1 (C-6), and 62.9 (OCH3)
prenyl group: δ 22.5 (C-1), 123.3 (C-2), 131.3 (C-3), 18.1 (C-4), and 25.9 (C-5)
R5 group: δ 126.8 (C-1), 116.3 (C-2), 78.0 (C-3), and 28.5 (C-4 and C-5)
acyl group: δ 203.6 (C-1’) and 31.1 (CH3)8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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4,6-Dihydroxy-1-ethanoyl-2-methoxy-3-(3”-methyl-but-2”-enyl)-5-(3’’’-methyl-but-1”’-enyl)-benzene (77)
C19H26O4
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Acronychia oligophlebia
China8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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1H NMR (300 MHz, CD3OD)
THB core: δ 3.72 (OCH3-2)
prenyl group: δ 3.30 (H-1), 5.19 (H-2), 1.76 (H-4), and 1.66 (H-5)
R5 group: δ 5.87 (H-1), 5.69 (H-2), 2.21 (H-3), and 0.92 (H-4 and H-5)
acyl group: δ 2.66 (CH3)
13C NMR (75 MHz, CD3OD)
THB core: δ 109.3 (C-1), 161.7 (C-2), 115.5 (C-3), 161.3 (C-4), 109.9 (C-5), 162.1 (C-6), and 63.4 (OCH3-2)
prenyl group: δ 23.7 (C-1), 124.6 (C-2), 132.0 (C-3), 18.0 (C-4), and 25.9 (C-5)
R5 group: δ 117.1 (C-1), 146.2 (C-2), 30.0 (C-3), and 22.7 (C-4 and C-5)
acyl group: δ 204.9 (C-1’) and 31.2 (CH3)8787 Yang, X.; Zhang, Y. B.; Wu, Z. N.; Zhang, X. Q.; Jiang, J. W.; Li, Y. L.; Wang, G. C; Fitoterapia 2015, 105, 156. [Crossref] Crossref...
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Hyperjaponol J (78)
C23H34O4
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Hypericum japonicum
China6868 Peng, X.; Tan, Q.; Zhou, H.; Xu, J.; Gu, Q.; Fitoterapia 2021, 153, 104984. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 2.13 (CH3-3 and CH3-5)
geranyl group:a δ 4.32 (H-1), 5.56 (H-2), 2.09 (H-4), 2.11 (H-5), 5.11 (H-6), 1.69 (H-8 and H-9), and 1.61 (H-10)
acyl group: δ 3.79 (H-1), 1.41 (H-2), 1.84 (H-2), 0.92 (H-3), and 1.17 (H-4)
13C NMR (100 MHz, CDCl3)
THB core: δ 107.0 (C-1), 158.2 (C-2 and C-6), 109.1 (C-3 and C-5), 161.7 (C-4), and 8.8 (CH3-3 and CH3-5)
geranyl group:a δ 70.0 (C-1), 119.6 (C-2), 141.9 (C-3), 39.8 (C-4), 26.5 (C-5), 123.9 (C-6), 132.0 (C-7), 25.8 (C-8), 16.6 (C-9), and 17.8 (C-10)
acyl group: δ 211.5 (C-1’), 46.5 (C-1), 27.1 (C-2), 12.1 (C-3), and 16.8 (C-4)6868 Peng, X.; Tan, Q.; Zhou, H.; Xu, J.; Gu, Q.; Fitoterapia 2021, 153, 104984. [Crossref] Crossref...
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Hyperjaponol K (79)
C22H32O4
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Hypericum japonicum
China6868 Peng, X.; Tan, Q.; Zhou, H.; Xu, J.; Gu, Q.; Fitoterapia 2021, 153, 104984. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 2.13 (CH3-3 and CH3-5)
geranyl group:a δ 4.32 (H-1), 5.55 (H-2), 2.09 (H-4), 2.11 (H-5), 5.10 (H-6), 1.69 (H-8 and H-9), and 1.61 (H-10)
acyl group: δ 3.94 (H-1) and 1.19 (H-2 and H-3)
13C NMR (100 MHz, CDCl3)
THB core: δ 106.5 (C-1), 158.2 (C-2 and C-6), 109.1 (C-3 and C-5), 161.8 (C-4), and 8.8 (CH3-3 and CH3-5)
geranyl group:a δ 70.0 (C-1), 119.6 (C-2), 142.0 (C-3), 39.8 (C-4), 26.5 (C-5), 123.9 (C-6), 132.0 (C-7), 25.8 (C-8), 16.6 (C-9), and 17.8 (C-10)
acyl group: δ 211.7 (C-1’), 39.8 (C-1), and 19.4 (C-2 and C-3)6868 Peng, X.; Tan, Q.; Zhou, H.; Xu, J.; Gu, Q.; Fitoterapia 2021, 153, 104984. [Crossref] Crossref...
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2-Acetyl-3,5-dihydroxy-1-geranoxy-6-methyl-4-(2-methyl)-butyryl-benzene (80)
C24H34O5
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Hypericum japonicum
China8989 Hu, L. H.; Khoo, C. W; Vittal, J. J.; Sim, K. Y; Phytochemistry 2000, 53, 705. [Crossref] Crossref...
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1H NMR (300 MHz, CDCl3)
THB core: δ 2.12 (H-5) and 9.45 (OH-2 and OH-4)
geranyl group:a δ 4.32 (H-1), 5.55 (H-2), 2.10 (H-4), 2.12 (H-5), 5.10 (H-6), 1.68 (H-8), 1.68 (H-9), and 1.61 (H-10)
acyl R1 group: δ 2.16 (CH3)
acyl R3 group: δ 3.78 (H-2), 1.85 (H-3), 1.41 (H-3), 0.91 (H-4), and 1.18 (H-5)
13C NMR (75 MHz, CDCl3)
THB core: δ 106.8 (C-1), 157.9 (C-2), 108.8 (C-3), 157.9 (C-4), 108.8 (C-5), and 61.5 (C-6)
geranyl group:a δ 69.7 (C-1), 119.4 (C-2), 141.6 (C-3), 39.5 (C-4), 26.2 (C-5), 123.7 (C-6), 131.8 (C-7), 25.6 (C-8), 16.4 (C-9), and 17.6 (C-10)
acyl R1 group: δ 205.6 (C-1’) and 30.8 (CH3)
acyl R3 group: δ 211.2 (C-1), 46.3 (C-2), 26.8 (C-3), 11.9 (C-4), and 16.6 (C-5)8989 Hu, L. H.; Khoo, C. W; Vittal, J. J.; Sim, K. Y; Phytochemistry 2000, 53, 705. [Crossref] Crossref...
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Acronyculatin A (81)
C15H18O5
|
Acronychia pedunculata
Taiwan9090 Su, C.-R.; Kuo, P-C; Wang, M.-L.; Liou, M. J.; Damu, A. G.; Wu, T. S.; J. Nat. Prod. 2003, 66, 990. [Crossref] Crossref...
Acronychia pubescens
Australia5454 Robertson, L. P.; Lucantoni, L.; Duffy, S.; Avery, V. M.; Carroll, A. R.; J. Nat. Prod. 2019, 82, 1019. [Crossref] Crossref...
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1H NMR (300 MHz, CDCl3)
THB core: δ 14.63 (OH-2), 3.86 (H-6), and 13.13 (OH-4)
prenyl group: δ 3.27 (H-1), 5.17 (H-2), 1.77 (H-4), and 1.70 (H-5)
acyl R1 group: δ 2.68 (CH3)
acyl R3 group: δ 10.30 (COH)
13C NMR (75 MHz, CDCl3)
THB core: δ 106.9 (C-1), 168.8 (C-2), 107.1 (C-3), 168.9 (C-4), 114.9 (C-5), 168.5 (C-6), and 62.7 (OCH3)
prenyl group: δ 21.9 (C-1), 121.8 (C-2), 132.6 (C-3), 25.7 (C-4), and 17.9 (C-5)
acyl R1 group: δ 213.1 (C-1’) and 31.0 (CH3)
acyl R3 group: δ 193.4 (COH)9090 Su, C.-R.; Kuo, P-C; Wang, M.-L.; Liou, M. J.; Damu, A. G.; Wu, T. S.; J. Nat. Prod. 2003, 66, 990. [Crossref] Crossref...
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1-Acetyl-4-isopentenyl-6-methylphloroglucinol (82)
C14H18O4
|
Leucanthemopsis pulverulenta
Spain9191 Pascual, J. T.; Valle, M. A. M.; Gonzalez, M. S.; Bellido, I. S.; Phytochemistry 1982, 21, 791. [Crossref] Crossref...
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1H NMR (60 MHz, CDCl3)
THB core: δ 5.82 (H-3), 5.68 (H-5), 13.75 (OH-6), and 3.75 (OCH3)
prenyl group: δ 4.40 (H-1), 5.34 (H-2), 1.72 (H-4), and 1.78 (H-5)
acyl group: δ 2.48 (CH3)9191 Pascual, J. T.; Valle, M. A. M.; Gonzalez, M. S.; Bellido, I. S.; Phytochemistry 1982, 21, 791. [Crossref] Crossref...
1-Acetyl-3-hydroxy-2,6-dimethyl-4-isopentenylphloroglucinol (83)
C15H20O4
Leucanthemopsis pulverulenta
Spain9191 Pascual, J. T.; Valle, M. A. M.; Gonzalez, M. S.; Bellido, I. S.; Phytochemistry 1982, 21, 791. [Crossref] Crossref...
1H NMR (60 MHz, CDCl3)
THB core: δ 6.06 (H-3), 3.69 (OCH3), 3.90 (OCH3), and 7.95 (OH-5)
prenyl group: δ 4.45 (H-1), 5.35 (H-2), and 1.73 (H-4 and H-5)
acyl group: δ 2.57 (CH3)9191 Pascual, J. T.; Valle, M. A. M.; Gonzalez, M. S.; Bellido, I. S.; Phytochemistry 1982, 21, 791. [Crossref] Crossref...
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Melibarbinon B (84)
C15H20O4
|
Melicope barbigera
United States9292 Le, K.-T.; Bandolik, J. J.; Kassack, M. U.; Wood, K. R.; Paetzold, C; Appelhans, M. S.; Passreiter, C. M.; Molecules 2021, 26, 688. [Crossref] Crossref...
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1H NMR (600 MHz, DMSO)
THB core: δ 6.21 (H-5), 13.98 (OH-2), 3.87 (OCH3-4), and 3.92 (OCH3-6)
prenyl group: δ 2.62 (H-1), 2.71 (H-1), 4.14 (H-2), 4.51 (H-4), 4.54 (H-4), and 1.69 (H-5)
acyl group: δ 2.56 (CH3)
13C NMR (150 MHz, DMSO)
THB core: δ 105.0 (C-1), 163.1 (C-2), 106.0 (C-3), 164.1 (C-4), 87.1 (C-5), and 161.8 (C-6)
prenyl group: δ 28.6 (C-1), 73.5 (C-2), 148.1 (C-3), 109.7 (C-4), and 16.9 (C-5)
acyl group: δ 203.0 (C-1’) and 32.9 (CH3)9292 Le, K.-T.; Bandolik, J. J.; Kassack, M. U.; Wood, K. R.; Paetzold, C; Appelhans, M. S.; Passreiter, C. M.; Molecules 2021, 26, 688. [Crossref] Crossref...
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2,4-Dihydroxy-3,6-dimethoxy-5-(3’,3’-dimethylallyl)-butyrophenone (85)
C17H24O4
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Leontonyx spathulatus
South Africa4141 Bohlmann, F.; Suwita, A.; Phytochemistry 1978, 17, 1929. [Crossref] Crossref...
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1H NMR (270 MHz, CDCl3)
THB core: δ 12.83 (OH-2 and OH-4), 3.89 (H-3 or H-6), and 3.90 (H-3 or H-6)
prenyl group: δ 3.30 (H-1), 5.20 (H-2), 1.67 (H-4), and 1.73 (H-5)
acyl group: δ 3.05 (H-1), 1.50 (H-2), and 0.98 (H-3)4141 Bohlmann, F.; Suwita, A.; Phytochemistry 1978, 17, 1929. [Crossref] Crossref...
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Acronyculatin P (86)
C20H28O4
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Acronychia pedunculata
Indonesia8484 Tanjung, M.; Nurmalasari, L; Wilujeng, A. K.; Saputri, R. D.; Rachmadiarti, F.; Tjahjandarie, T. S.; Nat. Prod. Sci. 2018, 24, 284. [Crossref] Crossref...
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1H NMR (400 MHz, CDCl3)
THB core: δ 13.43 (OH-6) and 3.71 (OCH3-2 and OCH3-4)
R5 group: δ 6.40 (H-1), 6.55 (H-2), 2.48 (H-3), and 1.10 (H-4 and H-5)
prenyl group: δ 3.29 (H-1), 5.16 (H-2), 1.78 (H-4), and 1.69 (H-5)
acyl group: δ 2.71 (CH3)
13C NMR (100 MHz, CDCl3)
THB core: δ 111.9 (C-1), 159.6 (C-2), 120.4 (C-3), 163.5 (C-4), 116.4 (C-5), 161.5 (C-6), 60.4 (OCH3-4), and 63.0 (OCH3-2)
R5 group: δ 116.7 (C-1), 143.1 (C-2), 32.9 (C-3), and 22.6 (C-4 and C-5)
prenyl group: δ 23.2 (C-1), 123.8 (C-2), 131.6 (C-3), 17.9 (C-4), and 25.8 (C-5)
acyl group: δ 204.7 (C-1’) and 31.4 (CH3)8484 Tanjung, M.; Nurmalasari, L; Wilujeng, A. K.; Saputri, R. D.; Rachmadiarti, F.; Tjahjandarie, T. S.; Nat. Prod. Sci. 2018, 24, 284. [Crossref] Crossref...
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1’-(2,4-Dihydroxy-3-(3”-methylbut-2”-enyl)-5-(1’’’-ethoxy-3’’’-methylbutyl)-6’-methoxy)-phenylethanone (87)
C21H32O5
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Acronychia pedunculata
China8282 Sy, L. K.; Brown, G. D.; Phytochemistry 1999, 52, 681. [Crossref] Crossref...
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1H NMR (500 MHz, CDCl3)
THB core: δ 13.60 (OH-2 or OH-4), 9.84 (OH-2 or OH-4), and 3.72 (H-6)
prenyl group: δ 3.27 (H-1), 5.20 (H-2), 1.70 (H-4), and 1.77 (H-5)
R5 group: δ 5.00 (H-1), 3.52 (H-2), 3.61 (H-2), 1.23 (H-3), 1.40 (H-4), 1.80 (H-4), 1.84 (H-5), 0.95 (H-6), and 0.96 (H-7)
acyl group: δ 2.67 (CH3)
13C NMR (125 MHz, CDCl3)
THB core: δ 108.2 (C-1), 160.9 (C-2), 114.7 (C-3), 162.3 (C-4), 109.4 (C-5), and 160.5 (C-6)
prenyl group: δ 22.4 (C-1), 123.2 (C-2), 131.5 (C-3), 25.7 (C-4), and 17.9 (C-5)
R5 group: δ 75.7 (C-1), 65.7 (C-2), 15.1 (C-3), 44.1 (C-4), 24.7 (C-5), 23.4 (C-6), and 21.7 (C-7)
acyl group: δ 203.5 (C-1’) and 31.0 (CH3)8282 Sy, L. K.; Brown, G. D.; Phytochemistry 1999, 52, 681. [Crossref] Crossref...
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Acronyculatin C (88)
C19H26O5
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Acronychia pedunculata
Taiwan9090 Su, C.-R.; Kuo, P-C; Wang, M.-L.; Liou, M. J.; Damu, A. G.; Wu, T. S.; J. Nat. Prod. 2003, 66, 990. [Crossref] Crossref...
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1H NMR (300 MHz, CDCl3)
THB core: δ 15.56 (OH-2), 3.77 (H-6), and 15.12 (OH-4)
prenyl group: δ 3.28 (H-1), 5.18 (H-2), 1.77 (H-4), and 1.69 (H-5)
acyl R1 group: δ 2.69 (CH3)
acyl R3 group: δ 3.03 (H-2), 2.27 (H-3), 0.98 (H-4), and 0.97 (H-5)
13C NMR (75 MHz, CDCl3)
THB core: δ 107.3 (C-1), 174.1 (C-2), 107.4 (C-3), 171.0 (C-4), 115.3 (C-5), 168.6 (C-6), and 62.6 (OCH3)
prenyl group: δ 22.3 (C-1), 122.3 (C-2), 132.2 (C-3), 25.7 (C-4), and 17.9 (C-5)
acyl R1 group: δ 203.8 (C-1’) and 31.0 (CH3)
acyl R3 group: δ 207.0 (C-1), 53.3 (C-2), 24.9 (C-3), and 22.8 (C-4 and C-5)9090 Su, C.-R.; Kuo, P-C; Wang, M.-L.; Liou, M. J.; Damu, A. G.; Wu, T. S.; J. Nat. Prod. 2003, 66, 990. [Crossref] Crossref...
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