Figure 1
Structures of cyclo-(L-Leu- L-Pro) (1), cyclo-(L-Phe-trans-4-OH-L-Pro) (2), cyclo-(L-Phe- L-Pro) (3) cyclo-(L-Trp- L-Pro) (4), prodigiosin (5), deoxycholic acid (6), cholic acid (7) and of giovaninones A-D (8-11).
Figure 2
Structures of verongidoic acid (12), 11-hydroxyaerothionin (13) and fistularin-3 (14).
Figure 3
Structures of [β-Me-Pro] destruxin E chlrohydrin (15), destruxin E chlorohydrin (16), pseudodestruxin C (17), [Phe3, N-Me-Val5] destruxin B (18), roseotoxin B (19), roseocardin (20), isariin (21) and isariin B (22).
Figure 4
Structures of (E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec-8-ene-1,3-dione (23), 1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecene-1,3-dione (24), citrinalin A (25), B (26), citrinin (27), citrinalin C (28), meleagrine (29), oxaline (30), roquefortine L (31) and roquefortine C (32).
Scheme 1
Biosynthesis of citrinalins.3939 Mercado-Marin, E. V.; Garcia-Reynaga, P.; Romminger, S.; Pimenta, E. F.; Romney, D. K.; Lodewyk, M. W.; Williams, D. E.; Andersen, R. J.; Miller, S. J.; Tantillo, D. J.; Berlinck, R. G. S.; Sarpong, R.; Nature
2014, 509, 318.
Scheme 2
Biosynthesis of maleagrin (29) and oxaline (30) via roquefortine L (31).4040 Newmister, S. A.; Gober, C. M.; Romminger, S.; Yu, F.; Tripathi, A.; Parra, L. L. L.; Williams, R. M.; Berlinck, R. G. S.; Joullié, M. M.; Sherman, D. H.; J. Am. Chem. Soc.
2016, 138, 11176.
Figure 5
Structures of 13-desoxy-phomenome (33), norliquexanthone (34), (S)-8-methoxy-3,5-dimethylisochroman-6-ol (35), roridin A (36), pyrenocines A (37), B (38) and J (39).
Figure 6
Structures of 18-deoxycytochalasin H (40), mycophenolic acid (41) and dicerandrol C (42).
Figure 7
Structures of (R)-mellein (43), penicillic acid (44), cis-4-hydroxymellein (45), trans-4-hydroxymellein (46), (Z)-2-ethylhex-2-enedioic acid (47) and (E)-4-oxo-2-propylideneoct-7-enoic acid (48).
Figure 8
Structures of pseurotins A (49), B (50), FD-838 (51), fumitremorgin C (52), 12,13-dihydroxy-fumitremorgin C (53), methylsulochrin (54), bis(dethio)bis(methylthio)gliotoxin (55), cytochalasin D (56), 5-methylmellein (58) and 5,7-dichloro-3-methyl-6-methoxy-8-hydroxy-3,4-dihydroisocoumarin (59).
Scheme 3
Biosynthesis of roussoellatide (57).4949 Ferreira, E. L. F.; Williams, D. E.; Ióca, L. P.; Morais-Urano, R. P.; Santos, M. F. C.; Patrick, B. O.; Elias, L. M.; Lira, S. P.; Ferreira, A. G.; Passarini, M. R. Z.; Sette, L. D.; Andersen, R. J.; Berlinck, R. G. S.; Org. Lett. 2015, 17, 5152.
Figure 9
Structures of 15(S)-10,11-dehydrocurvularin (60), 15(S)-12-keto-10,11-dehydrocurvularin (61), 15(S)-cis-10,11-epoxycurvularin (62), 10(R),11(R),15(S),18(S)-cyclothiocuvularin A (63), 10(S),11(S),15(S),18(R)-cyclothiocuvularin B (64), the methyl esther (65), 15(S),18(S)-cyclosulfoxicurvularin (66) and its methyl esther (67).
Figure 10
Structures of sydowic acid (68), (-)-naphthoquinoneimine (69) along with seven known compounds, aurosperone A (70), aurosperone C (71), pyranonigrins B (72), C (73), pyrophen (74), leucomelone (75) and atromentin (76).
Figure 11
Structures of penicitrinone A (77), pinselin (78), emodin (79), quinolactacin B (80) and C (81), penicillenol A1 (82), citreorosein (83), (+)-abscisic acid (84), 4-hydroxy-3-(3-methylbut-2-enyl)benzoic acid (85), anofinic acid (86), new 2,3-dihydro-6,7-dihydroxy-2,2-dimethylchromen-4-one (87) and harzianopyridone (88).
Figure 12
Structures of ingenamine G (89), cyclostellettamines A-I, K and L (90-100), mandangamine F (101), haliclonacyclamine (102), arenosclerins D (103) and E (104).
Figure 13
Structures of 4-methylaaptamine (105), halisphingosine A (106), halisphingosine B (107), haliotoxin (108) and amphitoxin (109).
Figure 14
Structures of serotonin (110), geodiamolides A (111), B (112), H (113) and I (114).
Figure 15
Structures of isoptilocaulin (115), mirabilin B (116), 8β-hydroxyptilocaulin (117), ptilocaulin (118), of the 8β and 8α-epimers mixture of 8-hydroxymirabilin (119-120), monalidine A (121) and arbusculidine A (122).
Figure 16
Structures of batzellamide A (123), hemibatzelladine J (124), Δ1919 Sacristán-Soriano, O.; Banaigs, B.; Casamayor, E. O.; Becerro, M. A.; Appl. Environ. Microbiol.
2011, 77, 862.-hemibatzelladine J (125), Δ2020 Shieh, W. Y.; Lin, Y. T.; Jean, W. D.; Int. J. Syst. Evol. Microbiol.
2004, 54, 2307.-hemibatzelladine J (126), batzelladines D (127), F (128), L (129) and nor-L (130).
Figure 17.
Structures of 2-(3,5-dibromo-4-methoxyphenyl)-N,N,N-dimethylethanammonium (131), 2,6-dibromo-4-(2-(trimethylammonium)ethyl)phenol (132), agelocaissarines A1 (133), A2 (134), B1 (135), B2 (136), caissarine C (137), 11-deoxyfistularin-3 (138), 2-(3-amino-2,4-dibromo-6-hydroxyphenyl)acetic acid (139), 3-(3,5-dibromo-4-methoxyphenyl-2-methoxy-N-methylpropan-1-ammonium (140), (3',5'-dibromo-4'-ethoxy-1'-hydroxy-4'-methoxycycloexa-2',5'-dienyle)acetamide (141), aeroplysinin-2 (142), ethyl of 2,4-dibromo-1-hydroxy-3-methoxy-6-oxa-3-azaspiro[4.5]dec-2,4,8-trieno-8-carboxylate (143) and (R*,S*)-[3,5-dibromo-4-(2-oxo-5-oxazolidinyl)methoxyphenyl]-2-oxazolidinone (144).
Figure 18
Structures of cavernicolins-1 (145) and -2 (146), aplysinafulvin (147), along with the dimethylketal 148, 11-oxoaerothionin (149), 11-oxo-12-hydroxyaerothionin (150), aerothionin (151), the phenol 152, the mixed ketal 153, subereatensin (154), homoaerothionin (155), aerophobin-1 (156) aerophobin-2 (157), aplysinamisin-1 (158), aeroplysinin-1 (159), 2-(3,5-dibromo-1-hydroxy-4-oxocyclohexa-2,5-dienyl)acetamide (160), the methyl esther of verongidoic acid (161), 11-ketofistularin-3 (162), 11,12-hydroxiaerothionin (163) and aplysfistularine (164).
Figure 19
Structures of aplysterol (165), 24,28-didehydroaplysterol (166), halistanol (167), halistanol sulfate C (168), pyrodysinoic acid (169), isopyrodysinoic acid (170), 13-hydroxyisopyrodysinoic acid (171) and pyrodisinoic acid B (172).
Figure 20
Structures of ilhabelanol (173), ilhabrene (174), isoakaterpin (175), halistanol sulfate A (176), furodysinin (177), 9α,11α-epoxicholest-7-en-3β,5α,6α,10-tetrol-6-acetate (178) and of 4H-pyran-2-ol-acetate (179).
Figure 21
Structures of plakortenone (180), plakortin (181), plakortide P (182), (2Z,6R,8R,9E)-methyl 3,6-epoxy-4,6,8-triethyl-2,4,9-dodecatrienoate (183), spongosoritin (184) and (2E,6R,8S)-methyl 3,6-epoxy-4,6,8-triethyldodeca-2,4-dienoate (185).
Figure 22
Structures of 7,8-dihydroplakortide E (186), a diastereoisomer of plakortide H (187), polyketide 188, 6-desmethyl-6-ethyl-spongosoritin A (189), 6-desmethyl-6-ethyl-9,10-dihydrospongosoritin A (190), spongosoritin A (191), 9,10-dihydrospongosoritin A (192), and of polyketides 193 and 194.
Figure 23
Structures of oxeatine (195) and oxeatamides H-J (196-198), oxeatamide A (199), the methyl ester of oxeatamide A (200), and membranolide (201).
Figure 24
Structures of 18-acetoxypregna-1,4,20-trien-3-one (202), 23-keto-cladiellin A (203), punicinols A (204), B (205), C (206), D (207) and E (208).
Figure 25
Structures of perezone (209), triacetyl perezone (210) of the epimeric mixture of 2-((2R)-5-hydroxy-6-methylhept-6-en-2-yl)-5-methylbenzenene-1,4-diol (211 and 212), amphidinolide P (213) and its 3-O-methyl derivative (214).
Figure 26
Structures of tambjamines A (215), B (216), C (217), D (218), K (219), 5'-bromo-4-methoxy-2,2'-pyrrol-5-carboxyaldehyde (220), tambjamine J1 (221), 2,5,6-tribromo-N-methylgramine (222) and of 2,6-dibromo-N-methylgramine (223).
Figure 27
Structures of rodriguesines A (224) and B (225), rodriguesic acid (226), its hydroxamate (227), and of the corresponding methyl esters 228 and 229.
Figure 28
Structures of (2S,3R)-2-aminododecan-3-ol (230), 3Z,6Z,9Z-dodecatrien-1-ol (231), asterubin (232), N,N-dimethyl-O-methylethanolamine (233), and of rodriguesines N-acetyl derivatives 234 and 235.
Figure 29
Structures of 2-hydroxy-7-oxostaurosporine (236), 3-hydroxy-7-oxostaurosporine (247) and of staurosporine (238).
Scheme 4
Total synthesis of pentabromopseudilin (139).101101 Schwalm, C. S.; Castro, I. B. D.; Ferrari, J.; Oliveira, F. L.; Aparicio, R.; Correia, C. R. D.; Tetrahedron Lett. 2012, 53, 1660.
Scheme 5
Total synthesis of enhygrolide A (244).102102 Felder, S.; Kehraus, S.; Neu, E.; Bierbaum, G.; Schäberle, T. F.; König, G. M.; ChemBioChem
2013, 14, 1363.
Scheme 6
Total synthesis of coibacin A [(5S, 16R, 18R)-251].104104 Carneiro, V. M. T.; Avila, C. M.; Balunas, M. J.; Gerwick, W. H.; Pilli, R. A.; J. Org. Chem. 2014, 79, 630.
Scheme 7
Total synthesis of lyngbyabellin M (271).106106 Pirovani, R. V.; Brito, G. A.; Barcelos, R. C.; Pilli, R. A.; Mar. Drugs
2015, 13, 3309.
Scheme 8
Syntheses of 3-bromoverongiaquinol (290) and 5-monobromocavernicolin (291).109109 Godoy, L. A. F.; Pilli, R. A.; Quim. Nova
2010, 33, 2042.
Scheme 9
Synthesis of (+)-trans-trikentrin A (296).111111 Tébéka, I. R. M.; Longato, G. B.; Craveiro, M. V.; Carvalho, J. E.; Ruiz, A. L. T. G.; Silva Jr., L. F.; Chem.-Eur. J. 2012, 18, 16890.
Scheme 10
Total synthesis of monalidine (121).7171 Santos, M. F. C.; Harper, P. M.; Williams, D. E.; Mesquita, J. T.; Pinto, E. G.; Costa-Silva, T. A.; Hajdu, E.; Ferreira, A. G.; Santos, R. A.; Murphy, P. J.; Andersen, R. J.; Tempone, A. G.; Berlinck, R. G. S.; J. Nat. Prod.
2015, 78, 1101.
Scheme 11
Total synthesis of synthesis of metachromin A (309).113113 Almeida, W. P.; Correia, C. R. D.; Tetrahedron Lett. 1994, 35, 1367; Almeida, W. P.; Correia, C. R. D.; J. Braz. Chem. Soc. 1999, 10, 401.
Scheme 12
Total synthesis of esculetin-4-carboxylic acid ethyl ester (322).114114 Lira, S. P.; Seleghim, M. H. R.; Williams, D. E.; Marion, F.; Hamill, P.; Jean, F.; Andersen, R. J.; Hajdu, E.; Berlinck, R. G. S.; J. Braz. Chem. Soc. 2007, 18, 440.
Scheme 13
Total synthesis of callystatin A (327).116116 Dias, L. C.; Meira, P. R. R.; J. Org. Chem. 2005, 70, 4762.
Scheme 14
Total synthesis of racemic pathylactone A (352).118118 Coelho, F.; Diaz, G.; Tetrahedron
2002, 58, 1647.
Scheme 15
Total synthesis of racemic spisulosine (364).119119 Amarante, G. W.; Cavallaro, M.; Coelho, F.; Tetrahedron Lett. 2010, 51, 2597.
Scheme 16
Total synthesis of polycitrin A (369).121121 Burtoloso, A. C. B.; Garcia, A. L. L.; Miranda, K. C.; Correia, C. R. D.; Synlett
2006, 3145.
Scheme 17
Total synthesis of synthesis of rubrolide B (377).124124 Karak, M.; Acosta, J. A. M.; Barbosa, L. C. A.; Boukouvalas, J.; Eur. J. Org. Chem. 2016, 3780.
Figure 30
Articles on marine natural products published by Brazilian researchers as corresponding authors between January 2004 and August 2017.
Figure 31
Number of marine natural products per biological group isolated by Brazilian researchers as corresponding authors.
Figure 32
Biogenetic origin of marine natural products isolated by Brazilian researchers as corresponding authors.