Norlanostane triterpenoidal saponins from the marine sponge melophlussarassinorum

Hao-Fu Dai; Ru Angelie Edrada; Rainer Ebel; Manfred Nimtz; Victor Wray; Peter Proksch; Ruangelie Edrada-Ebel

doi:10.1021/np050152d

Norlanostane triterpenoidal saponins from the marine sponge melophlussarassinorum

Hao-Fu Dai, Ru Angelie Edrada, Rainer Ebel, Manfred Nimtz, Victor Wray, Peter Proksch, Ruangelie Edrada-Ebel

Strathclyde Institute Of Pharmacy And Biomedical Sciences

Research output: Contribution to journal › Article

37 Citations (Scopus)

Abstract

Along with five known 30-norlanostane-type saponins, sarasinosides A(1) (5A), A3 (6A), I1 (7), I2 (8), and H2 (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 A1 and H2, respectively. The carbon skeleton of sarasinoside M (4) possesses a rearranged 8alpha,9alpha-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.

Original language	English
Pages (from-to)	1231-1237
Number of pages	7
Journal	Journal of Natural Products
Volume	68
Issue number	8
DOIs	https://doi.org/10.1021/np050152d
Publication status	Published - Aug 2005

Keywords

anti-bacterial agents
antifungal agents
bacillus subtilis
chromatography
glycosides
lanosterol
microbial sensitivity tests
molecular structure
nuclear magnetic resonance
porifera
saccharomyces cerevisiae
stereoisomerism
triterpenes

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10.1021/np050152d

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@article{3ee9d38536064377b586c6feff58eb38,

title = "Norlanostane triterpenoidal saponins from the marine sponge melophlussarassinorum",

abstract = "Along with five known 30-norlanostane-type saponins, sarasinosides A(1) (5A), A3 (6A), I1 (7), I2 (8), and H2 (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 A1 and H2, respectively. The carbon skeleton of sarasinoside M (4) possesses a rearranged 8alpha,9alpha-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.",

keywords = "anti-bacterial agents, antifungal agents, bacillus subtilis, chromatography, glycosides, lanosterol, microbial sensitivity tests, molecular structure, nuclear magnetic resonance, porifera, saccharomyces cerevisiae, stereoisomerism, triterpenes",

author = "Hao-Fu Dai and Edrada, {Ru Angelie} and Rainer Ebel and Manfred Nimtz and Victor Wray and Peter Proksch and Ruangelie Edrada-Ebel",

year = "2005",

month = aug,

doi = "10.1021/np050152d",

language = "English",

volume = "68",

pages = "1231--1237",

journal = "Journal of Natural Products",

issn = "0163-3864",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Norlanostane triterpenoidal saponins from the marine sponge melophlussarassinorum

AU - Dai, Hao-Fu

AU - Edrada, Ru Angelie

AU - Ebel, Rainer

AU - Nimtz, Manfred

AU - Wray, Victor

AU - Proksch, Peter

AU - Edrada-Ebel, Ruangelie

PY - 2005/8

Y1 - 2005/8

N2 - Along with five known 30-norlanostane-type saponins, sarasinosides A(1) (5A), A3 (6A), I1 (7), I2 (8), and H2 (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 A1 and H2, respectively. The carbon skeleton of sarasinoside M (4) possesses a rearranged 8alpha,9alpha-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.

AB - Along with five known 30-norlanostane-type saponins, sarasinosides A(1) (5A), A3 (6A), I1 (7), I2 (8), and H2 (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 A1 and H2, respectively. The carbon skeleton of sarasinoside M (4) possesses a rearranged 8alpha,9alpha-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.

KW - anti-bacterial agents

KW - antifungal agents

KW - bacillus subtilis

KW - chromatography

KW - glycosides

KW - lanosterol

KW - microbial sensitivity tests

KW - molecular structure

KW - nuclear magnetic resonance

KW - porifera

KW - saccharomyces cerevisiae

KW - stereoisomerism

KW - triterpenes

U2 - 10.1021/np050152d

DO - 10.1021/np050152d

M3 - Article

C2 - 16124767

VL - 68

SP - 1231

EP - 1237

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 8

ER -