Studies on the chemical constituents of the South China Sea sponge Phacellia fusca

Zeng, Lang; Fu, X.; Su, Jingyu; Guzman, F.; Schmitz, John F.; Hossain, M. B.; Helm, D. van der

doi:10.1002/cjoc.19910090207

Cited by 6 publications

(2 citation statements)

References 8 publications

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“…It is widely distributed in Andaman Sea Coral Coast, Indian Ocean, and South China Sea. A number of constituents such as cycloheptapeptides, 10) bromopyrrole alkaloids, 11) and amphilectane diterpenes 12) have been discovered from S. massa and they were reported as antiproliferative, proteinkinase USP7, and nitric oxide (NO) inhibitors. [10][11][12] Herein, the isolation, structural elucidation, and the anti-Vpr activities of the active EtOAc extract and isolated chemical constituents are described.…”

Section: Introductionmentioning

confidence: 99%

Pyrrolactams from Marine Sponge Stylissa massa Collected from Myanmar and Their Anti-Vpr Activities

Win

Kodama

Aye

et al. 2021

CHEMICAL & PHARMACEUTICAL BULLETIN

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A new brominated pyrrolactam stylissaol A (1) together with four known analogues, 2-bromoaldisine, aldisine, spongiacidin D, and Z-hymenialdisine, were isolated from the EtOAc extract of marine sponge Stylissa massa collected in Myanmar. The absolute configuration at C-10 of 1 was determined as R by the electronic circular dichroism (ECD) data. Among the isolated compounds, 2-bromoaldisine showed anti-Viral Protein R (Vpr) activity against TREx-HeLa-Vpr cells with an effective dose of 10 µM and its potency was comparable to that of positive control damnacanthal.

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Section: Introductionmentioning

confidence: 99%

Pyrrolactams from Marine Sponge Stylissa massa Collected from Myanmar and Their Anti-Vpr Activities

Win

Kodama

Aye

et al. 2021

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…1 The same sponge yielded three pyrrololactam alkaloids: saldisin, 2-bromoaldisin and debromohymenialdisin. 2 Recently, furan analogues isolated from marine organisms have shown anticancer, [3][4][5] antibacterial, 6 anticoagulant, 7 antifungal, 8 antimalarial, 9 antiplatelet, 10 antituberculosis and antiviral activities 11 . Aldisin-based derivatives can be easily synthesised.…”

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confidence: 99%

The First Total Synthesis of Fuscain

Liang

Liao

Wang

et al. 2012

Journal of Chemical Research

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The first total synthesis of the furanolactam fuscain is reported. The key step in the synthesis was the formation of seven-membered lactam by acylation of a furan ring using the mild Lewis acid CuSO 4 ·5H 2 O.Keyword: fuscain, furanolactam, total synthesis, seven-membered ring, mild Lewis acid Fuscain, a new furanolactam which was originally isolated from the sponge Phacellis fusca collected in South China Sea, showed a moderate cytotoxicity toward P388 and L1210 cell lines. 1 The same sponge yielded three pyrrololactam alkaloids: saldisin, 2-bromoaldisin and debromohymenialdisin. 2 Recently, furan analogues isolated from marine organisms have shown anticancer, 3-5 antibacterial, 6 anticoagulant, 7 antifungal, 8 antimalarial, 9 antiplatelet, 10 antituberculosis and antiviral activities 11 . Aldisin-based derivatives can be easily synthesised. 12 However, it is still a challenge to synthesise fuscain. Hence the biological effects of fuscain and its derivatives on cell cycle progression and antitumour activities have rarely been reported.The synthetic route to fuscain is shown in Scheme 1. The key step is an intramolecular Friedel-Crafts cyclisation to form the seven-membered ring. Various Lewis acids (polyphosphoric acid, POCl 3 , polyphosphoric acid-acetic acid, POCl 3 -P 2 O 5 , TFA or MSA) have been reported for Friedel-Crafts cyclisation. 13,14 . Initially, we selected PPA and P 2 O 5 as catalysts but no product was obtained. Because of the structural difference between Alidisin and fuscain, the aromaticity of furan ring is less than a pyrrole ring, and a furan ring usually polymerised under acidic conditions, we selected a relatively mild Lewis acid CuSO 4 ·5H 2 O to complete the intramolecular cyclisation to form fuscain.Starting from commercially available furoic acid which gave the furan-2-carbonyl chloride, the synthesis was relatively easy following the literature. 15-17 Furan-2-carbonyl chloride condensed with the ethyl ester of β-alanine to provide the corresponding amides. This was followed by hydrolysis of the ester to give the acid. Intramolecular cyclisation gave the desired compound. * Correspondent.

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Monopyrrolic Natural Compounds Including Tetramic Acid Derivatives

Gossauer

2003

Progress in the Chemistry of Organic Natural Products

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Studies on the chemical constituents of the South China Sea sponge Phacellia fusca

Cited by 6 publications

References 8 publications

Pyrrolactams from Marine Sponge <i>Stylissa massa</i> Collected from Myanmar and Their Anti-Vpr Activities

Pyrrolactams from Marine Sponge <i>Stylissa massa</i> Collected from Myanmar and Their Anti-Vpr Activities

The First Total Synthesis of Fuscain

Monopyrrolic Natural Compounds Including Tetramic Acid Derivatives

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