Norlanostane triterpenoidal saponins from the marine sponge melophlussarassinorum.
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.
Dai
Hao-Fu
HF
Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität, Universitätsstrasse 1, Geb. 26.23, 40225 Düsseldorf, Germany.
Edrada
Ru Angelie
RA
Ebel
Rainer
R
Nimtz
Manfred
M
Wray
Victor
V
Proksch
Peter
P
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D002849:Chromatography, Gas; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007810:Lanosterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D006027:Glycosides; D014315:Triterpenes; C056083:sarasinoside A1; D007810:Lanosterol