Norlanostane triterpenoidal saponins from the marine sponge Melophlus sarassinorum

Along with five known 30-norlanostane-type saponins, sarasinosides A sub(1) (5A), A sub(3) (6A), I sub(1) (7), I sub(2) (8), and H sub(2) (9), four new triterpenoidal saponin congeners, sarasinosides J (1), K (2), L (3), and M (4), were isolated from the Indonesian sponge Melophlus sarassinorum. Sar...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2005-08, Vol.68 (8), p.1231-1237
Main Authors: Dai, H.F, Edrada, R.A, Ebel, R, Nimtz, M, Wray, V, Proksch, P
Format: Article
Language:English
Subjects:
animal products
antibacterial properties
antifungal properties
Bacillus subtilis
Biological and medical sciences
chemical structure
General pharmacology
Marine
Medical sciences
Melophlus
Melophlus sarassinorum
norlanostane
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Porifera
Saccharomyces cerevisiae
sarasinosides
spectral analysis
stereochemistry
triterpenoid saponins
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Summary:Along with five known 30-norlanostane-type saponins, sarasinosides A sub(1) (5A), A sub(3) (6A), I sub(1) (7), I sub(2) (8), and H sub(2) (9), four new triterpenoidal saponin congeners, sarasinosides J (1), K (2), L (3), and M (4), were isolated from the Indonesian sponge Melophlus sarassinorum. Sarasinosides J (1) and K (2) are the 24,25-hydrogenated congeners of the previously described sarasinosides A sub(1) and H sub(2), respectively. The carbon skeleton of sarasinoside M (4) possesses a rearranged 8 alpha 9, alpha -epoxy-8,9-seconorlanosta-8(14),9(11),24-triene system, which is novel and unprecedented in nature. The structures of the new compounds were confirmed by spectral analyses, chemical derivatization, and GC analyses. Compounds 1 and 5A exhibited antimicrobial activity toward Bacillus subtilis and Saccharomyces cerevisiae.
ISSN:0163-3864
1520-6025
DOI:10.1021/np050152d