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

44 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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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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

SN - 0163-3864

VL - 68

SP - 1231

EP - 1237

JO - Journal of Natural Products

JF - Journal of Natural Products

IS - 8

ER -

Norlanostane triterpenoidal saponins from the marine sponge melophlussarassinorum

Abstract

Keywords

UN SDGs

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