3-Hydroxy-7-phenyl-4E, 6E-heptadienoic Acid from an Ascidian Didemnum granulatum

Isaacs, S.; Kashman, Yoel; Benayahu, Yehuda

doi:10.1021/np50107a014

Cited by 8 publications

(5 citation statements)

References 2 publications

(3 reference statements)

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“…Some sponge, tunicate, and marine fungal metabolites have, however, clearly demonstrated the potential of marine natural products in this area. 1 Tunicates of the genus Didemnum have yielded a variety of secondary metabolites including peptides, [2][3][4] unusual nine-membered ring lactones, 5 β-carboline, 6,7 and indolederived alkaloids, 8 lamellarines, 9 didemnenones, 10 enterocin derivatives, 11 pyrroloacridine alkaloids such as plakinidine D, 12 small iodated aromatic compounds, 12,13 and long chain amino alcohols 14 and acids, 15 many of which are halogenated. Several of these compounds were found to have interesting biological activities, e.g., mollamide, 4 cyclodidemnoamide, 2 the didemnenones, 10 and plakinidine D 12 are all cytotoxic against various cancer cell lines, while enterocin 11 and the didemnenones 10 are antimicrobial.…”

Section: Introductionmentioning

confidence: 99%

Lepadins D−F: Antiplasmodial and Antitrypanosomal Decahydroquinoline Derivatives from the Tropical Marine Tunicate Didemnum sp.

et al. 2002

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From a new tunicate species, belonging to the genus Didemnum, three alkaloids possessing an unusual and extremely rare decahydroquinoline skeleton and showing significant and selective antiplasmodial and antitrypanosomal activity were obtained as follows: (2R*,3S*,4aR*,5R*,8aS*)-decahydro-3-hydroxy-5-(5'-hydroxyoctyl)-2-methylquinoline (lepadin D,1), its quaternary nitrogen derivative (2), (2R*,2"E,3S*,4aR*,5R*,8aS*)-decahydro-3-hydroxy-5-(5'-hydroxyoctyl)-2-methyl-3-quinolinyl ester 2"-octenoic acid (lepadin E, 3), and (2S*,2"E,3S*,4aR*,5R*,8aS*)-decahydro-3-hydroxy-5-(5'-hydroxyoctyl)-2-methyl-3-quinolinyl ester 2"-octenoic acid (lepadin F, 4). These isolates may well serve as lead structures for the development of new antimalarial drugs.

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Section: Introductionmentioning

confidence: 99%

Lepadins D−F: Antiplasmodial and Antitrypanosomal Decahydroquinoline Derivatives from the Tropical Marine Tunicate Didemnum sp.

et al. 2002

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“…The tubercidin analogs 5 -deoxy-3-iodotubercidin (50), 5 -deoxy-3-bromotubercidin (51), and 5 -deoxytubercidin (52) ( Figure 9) were isolated through chemical investigation of D. voeltzkowi [29]. Furthermore, hydroxy phenyldienoic acid (53) (Figure 9) was identified from the ethanolic extract of D. granulatum [30]. Asterubin (54) and N,N-dimethyl-O-methylethanolamine (55) ( Figure 9) were isolated from D. ligulum [31].…”

Section: Secondary Metabolites With No Currently Reported Bioactivitymentioning

confidence: 99%

Secondary Metabolites of the Genus Didemnum: A Comprehensive Review of Chemical Diversity and Pharmacological Properties

et al. 2020

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Tunicates (ascidians) are common marine invertebrates that are an exceptionally important source of natural products with biomedical and pharmaceutical applications, including compounds that are used clinically in cancers. Among tunicates, the genus Didemnum is important because it includes the most species, and it belongs to the most speciose family (Didemnidae). The genus Didemnum includes the species D. molle, D. chartaceum, D. albopunctatum, and D. obscurum, as well as others, which are well known for their chemically diverse secondary metabolites. To date, investigators have reported secondary metabolites, usually including bioactivity data, for at least 69 members of the genus Didemnum, leading to isolation of 212 compounds. Many of these compounds exhibit valuable biological activities in assays targeting cancers, bacteria, fungi, viruses, protozoans, and the central nervous system. This review highlights compounds isolated from genus Didemnum through December 2019. Chemical diversity, pharmacological activities, geographical locations, and applied chemical methods are described.

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“…102 A hydroxy phenyl heptadienoic acid, 3-hydroxy-7-phenyl-4E,6E-heptadienoic acid (302), had been obtained from the ascidian Didemnum granulatum collected from the Gulf of Eilat in the Red Sea. 103 In 1994, 3,5,8-trihydroxy-4-quinolone (303) was obtained from the Red Sea sponge Verongia sp.…”

Section: Other Metabolitesmentioning

confidence: 99%

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2017

IJPSR

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3-Hydroxy-7-phenyl-4E, 6E-heptadienoic Acid from an Ascidian Didemnum granulatum

Abstract: A new hydroxy phenylheptadienoic acid [1] has been isolated from the ascidian Didemnum granulatum collected from the Gulf of Eilat in the Red Sea.

Cited by 8 publications

References 2 publications

Lepadins D−F: Antiplasmodial and Antitrypanosomal Decahydroquinoline Derivatives from the Tropical Marine Tunicate Didemnum sp.

Lepadins D−F: Antiplasmodial and Antitrypanosomal Decahydroquinoline Derivatives from the Tropical Marine Tunicate Didemnum sp.

Secondary Metabolites of the Genus Didemnum: A Comprehensive Review of Chemical Diversity and Pharmacological Properties

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