Merosesquiterpenes from Two Sponges of the Genus Dysidea

Abstract

The chemical study of two sponges of the genus Dysidea collected in the Gulf of California has led to the isolation of the new merosesquiterpenes 20-O-acetyl-21-hydroxy-ent-isozonarol (2), 20-O-acetylneoavarol (3), ent-yahazunol (4), and dysienone (5), together with the known compounds 1 and 6-9. The structures of the new metabolites have been established by spectroscopic techniques. The absolute configuration of compounds 5 and 6 has been investigated by application of a procedure developed by Riguera et al. Compounds 2 and 5 showed cytotoxic activity against three human tumor cell lines.

Two novel alkaloids from the South China Sea marine sponge Dysidea sp.

“…Many of them have significant bioactivities, such as antibacterial, 9,[13][14][15] anti-inflammatory 16 and cytotoxic. 17,18 In our study of the bioactive compounds from marine sponges, two new (1, 2) and two known (3,4) alkaloids were isolated from the marine sponge Dysidea sp. The structures of two new metabolites were elucidated by interpretation of spectroscopic data.…”

Antibacterial Meroterpenoids from the South China Sea Sponge <i>Dysidea</i> sp.

“…3) These compounds have attracted much interest due to their structural diversity and varied biological activities, including anti-human immunodeficiency virus (HIV), 4) antibacterial, 5) antifungal, 6) antioxidative, 7) antitumor, 8) anti-inflammatory, 9) inhibition against protein tyrosine kinase (PTK) and protein tyrosine phosphatase 1B (PTP1B), 10,11) and activation of hypoxia-inducible factor-1 (HIF-1) activities. 12) During our search for bioactive metabolites from tropical sponges, we encountered a purple-colored encrusting Dysidea sp.…”

Drimane-Related Merosesquiterpenoids, a Promising Library of Metabolites for Drug Development

“…Based on the cyclization between sesquiterpenoid and 3,5-dimethylorsellinic acid (DMOA) units, as well as the rearrangement of DMOA, the type of tetraketide-MSRDs can be further classified into five subgroups (SG I-V), namely citreohybridones , terretonins (148)(149)(150)(151)(152)(153)(154)(155)(156), andibenins (157)(158)(159)(160)(161)(162)(163), autins , and others (194)(195)(196)(197)(198)(199). Isotope labeling experiments revealed that they were all formed through the alkylation of DMOA by FPP as a key step [87][88][89][90][91][92][93][94][95][96][97][98][99][100][101][102].…”

“…15) refers to those in which the sesquiterpenoid and DMOA moieties are linked by only one C-C bond. Tropolactones A-D (196)(197)(198)(199) were isolated from the broth extract of a marine-derived fungus of Aspergillus genus. Novofumigatonin (195) was isolated from Aspergillus novofumigatus [143].…”

“…They were all isolated from marine sources except for compounds 297 and 321 obtained from microbes. Beyond that, the biosynthesis of antipodal MSRDs by different organisms is of considerable interest, such as 274/275 and 272/276 [193,[196][197][198]. Later, its structure was revised from 283a to 283b [202].…”