Eupatolide |
1H-NMR (CDCl3, 500 MHz) δ: 1.55 (3H, br s, H-15a), 1.57 (3H, br s, H-4), 2.07 (1H, m, H-2b), 2.05 (1H, m, H-3a), 2.18 (1H, br d, 12.6, H-8b), 2.25 (1H, m, H-3b), 2.27 (1H, m, H-2a), 2.48 (1H, dd, 12.5, 4.0, H-9a), 2.85 (1H, dd, 7.8, 4.0, H-7), 4.47 (1H, m, H-8), 4.74 (1H, dd, 11.0, 1.7, H-1a), 4.76 (1H, d, 9.5, H-5a), 5.11 (1H, dd, 7.8, 4.0, H-6), 6.13 (1H, d, 3.0, H-13a), 5.62 (H, d, 3.0, H-13b). 13C-NMR (CDCl3, 125 MHz) δ: 136.0 (C-1), 25.6 (C-2), 38.7 (C-3), 140.4 (C-4), 128.0 (C-5), 74.8 (C-6), 52.7 (C-7), 70.3 (C-8), 47.1 (C-9), 127.7 (C-10), 138.8 (C-11), 169.9 (C-12), 120.1 (C-13), 16.8 (C-14), 19.5 (C-15) |
1.0 VIP Value < 1.5 |
S7 (10.576) |
Lee et al. (1972)Lee, K.-H., Furukawa, H., Huang, H.-C., & Huang, E.-S. (1972). Antitumor agents II: eupatolide, a new cytotoxic principle from Eupatorium formosanum HAY. Journal of Pharmaceutical Sciences, 61(4), 629-631. http://dx.doi.org/10.1002/jps.2600610432. PMid:4335375. http://dx.doi.org/10.1002/jps.2600610432...
, Zhou et al. (1994)Zhou, B.-N., Bai, N.-S., Lin, L.-Z., & Cordell, G. A. (1994). Sesquiterpene lactones from Inula salsoloides. Phytochemistry, 36(3), 721-724. http://dx.doi.org/10.1016/S0031-9422(00)89804-0. http://dx.doi.org/10.1016/S0031-9422(00)...
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Isoschaftoside |
1H-NMR (DMSO-d6, 500 MHz) δ: 6.69 (1H, br s, H-3), 6.72 (2H, d, J=8.7 Hz, H-3’, 5’), 7.99 (2H, d, J=8.4 Hz, H-2’, 6’), 13.67 (1H, br s, OH-5); 6-C-α-Ara: 3.44 (1H, m, H-3”), 3.78 (1H, m, H-4”), 3.81, 3.59 (2H, m, 5”-CH2), 4.04 (1H, br m, H-2”), 4.64 (1H, d, J=9.4 Hz, H-1”); 8-C-β-Glc: 3.28 (1H, m, H-5”’), 3.32 (1H, m, H-3”’), 3.37 (1H, m, H-4”’), 3.75, 3.56 (2H, m, 6”’-CH2), 3.92 (1H, m, H-2”’), 4.83 (1H, d, J=9.9 Hz, H-1”’). 13C-NMR (DMSO-d6, 125 MHz) δ: 128.8 (C-2’, 6’), 115.9 (C-3’, 5’), 102.2 (C-3); 6-C-α-Ara: 74.1 (C-1”), 69.2 (C-2”), 74.1 (C-3”), 68.6 (C-4”), 69.9 (C-5”); 8-C-β-Glc: 73.9 (C-1”’), 71.2 (C-2”’), 78.9 (C-3”’), 70.5 (C-4”’), 81.7 (C-5”’), 61.2 (C-6”’) |
1.0 VIP Value < 1.5 |
S8 (11.350) |
Fernando et al. (2019)Fernando, W. I. T., Attanayake, A. M. K. C., Perera, H. K. I., Sivakanesan, R., Jayasinghe, L., Araya, H., & Fujimoto, Y. (2019). Isolation, identification and characterization of pancreatic lipase inhibitors from Trigonella foenum-graecum seeds. South African Journal of Botany, 121, 418-421. http://dx.doi.org/10.1016/j.sajb.2018.10.023. http://dx.doi.org/10.1016/j.sajb.2018.10...
, Xie et al. (2003)Xie, C., Veitch, N. C., Houghton, P. J., & Simmonds, M. S. J. (2003). Flavone C-glycosides from Viola yedoensis MAKINO. Chemical & Pharmaceutical Bulletin, 51(10), 1204-1207. http://dx.doi.org/10.1248/cpb.51.1204. PMid:14519932. http://dx.doi.org/10.1248/cpb.51.1204...
|
(+)-Syringaresinol |
1H-NMR (CDCl3, 500 MHz) δ: 3.05 (2H, br s, H-8, 8'), 3.87 (2H, m, H-9, 9'), 3.88 (12H, s, OMe), 4.27 (2H, m, H-9, 9”), 4.70 (2H, s, H-7, 7'), 5.49 (2H, s, OH), 6.55 (4H, s, H-2, 6, 2', 6'). 13C-NMR (CDCl3, 125 MHz) δ: 147.6 (C-3, 5, 3', 5'), 134.6 (C-4, 4'), 132.6 (C-1, 1'), 103.2 (C-2, 6, 2', 6'), 86.7 (C-7, 7'), 72.3 (C-9, 9'), 56.8 (OMe), 54.8 (C-8, 8') |
0.5 < VIP Value < 1.0 |
S11 (14.233) |
Park et al. (2003)Park, J. A., Kim, H. J., Jin, C., Lee, K.-T., & Lee, Y. S. (2003). A new pterocarpan,(-)-maackiain sulfate, from the roots of Sophora subprostrata'. Archives of Pharmacal Research, 26(12), 1009-1013. http://dx.doi.org/10.1007/BF02994750. PMid:14723332. http://dx.doi.org/10.1007/BF02994750...
, El-Hassan et al. (2003)El-Hassan, A., El-Sayed, M., Hamed, A. I., Rhee, I. K., Ahmed, A. A., Zeller, K. P., & Verpoorte, R. (2003). Bioactive constituents of Leptadenia arborea. Fitoterapia, 74(1-2), 184-187. http://dx.doi.org/10.1016/S0367-326X(02)00314-3. PMid:12628421. http://dx.doi.org/10.1016/S0367-326X(02)...
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Rutin |
1H-NMR (MeOH-d4, 500 MHz) δ: 1.15 (3H, d, J = 6.1 Hz, rha-H-6), 4.54 (1H, d, J = 1.5 Hz, rha-H-1), 5.13 (1H, d, J = 7.7 Hz, glc-H-1), 6.22 (1H, d, J = 2.2 Hz, H-6), 6.43 (1H, d, J = 2.2 Hz, H-8), 6.88 (H, d, J = 8.3 Hz, H- 5’), 7.64 (1H, dd, J = 8.6, 2.2 Hz, H-6’), 7.68 (1H, d, J = 2.5 Hz, H-2’). 13C-NMR (MeOH-d4, 125 MHz) δ: 159.6 (C-2), 135.7 (s, C-3), 179.6 (s, C-4), 163.2 (s, C-5), 100.1 (d, C-6), 166.3 (s, C-7), 95.1 (d, C-8), 158.7 (s, C-9), 105.9 (s, C-10), 123.4 (s, C-1’), 116.3 (d, C-2’), 146.1 (s, C-3’), 150.2 (s, C-4’), 117.8 (d, C-5’), 123.8 (d, C-6’), 104.9 (d, glc-C-1), 76.0 (d, glc-C-2), 78.3 (d, glc-C-3), 71.6 (d, glc-C-4), 77.5 (d, glc-C-5), 68.9 (t, glc-C-6), 102.5 (d, rha-C-1), 72.4 (d, rha-C-2), 72.2 (d, rha-C-3), 74.2 (d, rha-C-4), 69.9 (d, rha-C-5), 18.1 (q, rha-C-6). |
0.5 < VIP Value < 1.0 |
S9 (11.955) |
Li et al. (2008)Li, Y.-L., Li, J., Wang, N.-L., & Yao, X.-S. (2008). Flavonoids and a new polyacetylene from Bidens parviflora Willd. Molecules, 13(8), 1931-1941. http://dx.doi.org/10.3390/molecules13081931. PMid:18794794. http://dx.doi.org/10.3390/molecules13081...
, Meng et al. (2009)Meng, L., Liu, R., Sun, A., Wu, S., & Liu, N. (2009). Separation and purification of rutin and acaciin from the Chinese medicinal herb Herba cirsii by combination of macroporous absorption resin and high-speed counter-current chromatography. Journal of Chromatographic Science, 47(5), 329-332. http://dx.doi.org/10.1093/chromsci/47.5.329. PMid:19476696. http://dx.doi.org/10.1093/chromsci/47.5....
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Naringenin |
1H-NMR (DMSO-d6, 500 MHz) δ: 2.71 (1H, dd, J=2.5, 16.0 Hz, H-3a), 3.15 (1H, dd, J=13.3, 16.0 Hz, H-3b), 5.43 (1H, dd, J=2.5, 13.3 Hz, H-2), 5.98 (2H, s, H-6, 8), 6.88 (2H, d, J=8.0 Hz, H-3’, 5’), 7.37 (2H, d, J=8.0 Hz, H-2’, 6’), 12.18 (1H, s, OH-5). 13C-NMR (DMSO-d6, 125 MHz) δ: 41.84 (C-3), 78.35 (C-2), 94.30 (C-8), 95.25 (C-6), 101.64 (C-10), 114.65 (C-3’, C-5’), 127.50 (C-2’, C-6’), 129.24 (C-1’), 157.18 (C-4’), 162.90 (C-9), 163.82 (C-5), 165.83 (C-7), 195.82 (C-4) |
0.5 < VIP Value < 1.0 |
S13 (10.400) |
Jeon et al. (2008)Jeon, S. H., Chun, W., Choi, Y. J., & Kwon, Y. S. (2008). Cytotoxic constituents from the bark of Salix hulteni. Archives of Pharmacal Research, 31(8), 978-982. http://dx.doi.org/10.1007/s12272-001-1255-9. PMid:18787784. http://dx.doi.org/10.1007/s12272-001-125...
, Singh et al. (2018)Singh, A. K., Raj, V., Keshari, A. K., Rai, A., Kumar, P., Rawat, A., Maity, B., Kumar, D., Prakash, A., De, A., Samanta, A., Bhattacharya, B., & Saha, S. (2018). Isolated mangiferin and naringenin exert antidiabetic effect via PPARγ/GLUT4 dual agonistic action with strong metabolic regulation. Chemico-Biological Interactions, 280, 33-44. http://dx.doi.org/10.1016/j.cbi.2017.12.007. PMid:29223569. http://dx.doi.org/10.1016/j.cbi.2017.12....
|
Vicenin II |
1H-NMR (DMSO-d6, 500 MHz) δ: 6.43 (1H, s, H-3), 6.86 (2H, d, J=8.8 Hz, H-3’, 5’), 7.92 (2H, d, J=8.8 Hz, H-2’, 6’), 13.69 (1H, s, OH-5); 6-C-β-Glc: 3.17 (1H, m, H-5”), 3.22 (2H, m, H-3”, 4”), 3.64, 3.49 (2H, m, 6”-CH2), 4.07 (1H, m, H-2”), 4.63 (1H, d, J=9.8 Hz, H-1”); 8-C-β-Glc: 3.29 (1H, m, H-3”’), 3.34 (1H, m, H-4”’), 3.26 (1H, m, H-5”’), 3.74, 3.53 (2H, m, 6”’-CH2), 3.86 (1H, m, H-2”’), 4.83 (1H, d, J=9.8 Hz, H-1”’). 13C-NMR (DMSO-d6, 125 MHz) δ: 127.8 (C-2’, 6’), 115.3 (C-3’, 5’), 101.0 (C-3); 6-C-β-Glc: 74.2 (C-1”), 70.6 (C-2”), 78.6 (C-3”’), 70.3 (C-4”’), 80.4 (C-5”), 60.9 (C-6”); 8-C-β-Glc: 74.3 (C-1”’), 71.6 (C-2”’), 78.9 (C-3”’), 70.6 (C-4”’), 81.2 (C-5”’), 61.2 (C-6”’) |
0.5 < VIP Value < 1.0 |
S2 (9.100) |
Xie et al. (2003)Xie, C., Veitch, N. C., Houghton, P. J., & Simmonds, M. S. J. (2003). Flavone C-glycosides from Viola yedoensis MAKINO. Chemical & Pharmaceutical Bulletin, 51(10), 1204-1207. http://dx.doi.org/10.1248/cpb.51.1204. PMid:14519932. http://dx.doi.org/10.1248/cpb.51.1204...
, Siciliano et al. (2004)Siciliano, T., Tommasi, N., Morelli, I., & Braca, A. (2004). Study of flavonoids of Sechium edule (Jacq) Swartz (Cucurbitaceae) different edible organs by liquid chromatography photodiode array mass spectrometry. Journal of Agricultural and Food Chemistry, 52(21), 6510-6515. http://dx.doi.org/10.1021/jf040214q. PMid:15479015. http://dx.doi.org/10.1021/jf040214q...
|
Dendrophenol |
1H-NMR (CDCl3, 500 MHz) δ: 2.73 (2H, m, H-7’), 2.77 (2H, m, H-7), 3.69 (3H, s, 3′-OCH3), 3.77 (3H, s, 5-OCH3), 6.18 (1H, t, J=2.2 Hz, H-4), 6.20 (1H, t, J=2.0 Hz, H-2), 6.22 (1H, t, J=1.6 Hz, H-6), 6.59 (1H, dd, J=8.0, 1.9 Hz, H-6’), 6.65 (1H, d, J=1.9 Hz, H-2’), 6.68 d (1H, d, J=8.0 Hz, H-5’). 13C-NMR (CDCl3, 125 MHz) δ: 38.5 (C-7′), 121.9 (C-6′), 116.0 (C-5′), 145.6 (C-4′), 56.3 (3′-OCH3), 148.7 (C-3′), 113.4 (C-2′), 134.8 (C-1′), 39.6 (C-7), 106.7 (C-6), 55.6 (5-OCH3), 162.2 (C-5), 99.9 (C-4), 159.4 (C-3), 109.2 (C-2), 145.6 (C-1) |
VIP Value < 0.5 |
S26 (32.766) |
Leong et al. (1997)Leong, Y.-W., Kang, C.-C., Harrison, L. J., & Powell, A. D. (1997). Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid bulbophyllum vaginatum. Phytochemistry, 44(1), 157-165. http://dx.doi.org/10.1016/S0031-9422(96)00387-1. http://dx.doi.org/10.1016/S0031-9422(96)...
, Shimizu et al. (1988)Shimizu, M., Shogawa, H., Hayashi, T., Arisawa, M., Suzuki, S., Yoshizaki, M., Morita, N., Ferro, E., Basualdo, I., & Berganza, L. H. (1988). Anti-inflammatory constituents of topically applied crude drugs. III. Constituents and anti-inflammatory effect of Paraguayan crude drug “Tamandá cuná”(Catasetum barbatum LINDLE). Chemical & Pharmaceutical Bulletin, 36(11), 4447-4452. http://dx.doi.org/10.1248/cpb.36.4447. PMid:3246013. http://dx.doi.org/10.1248/cpb.36.4447...
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