Cytotoxic cardenolides and antibacterial terpenoids from Crossopetalum gaumeri.
From the methanol extract of the roots of (Crossopetalum gaumeri, four new highly cytotoxic cardenolides, securigenin-3beta-O-beta-6-deoxyguloside (2), 19-hydroxy-sarmentogenin-3beta-O-beta-6-deoxyguloside (4), sarmentogenin-3beta-O-[alpha-allosyl-(1-->4)-beta-6-deoxy alloside] (5), and securigenin-3beta-O-[alpha-allosyl-(1-->4)-beta-6-deoxyal loside] (6) were isolated. The dichloromethane extract afforded the new diterpene 3,15-dihydroxy-18-norabieta-3,8,11,13-tetraene (7) as well as the new triterpene 2,3,7-trihydroxy-6-oxo-1,3,5(10),7-tetraene-24-nor-friedelane-29-o ic acid methylester (11). The new terpenoids lack cytotoxicity and the antibacterial activity is moderate to low.
Department of Applied Bioscience, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zurich, Zürich.
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A
Ankli
J
J
Heilmann
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M
Heinrich
O
O
Sticher
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001409:Bacillus cereus / Q000187:drug effects; D002298:Cardenolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity; D004926:Escherichia coli / Q000187:drug effects; D006801:Humans; D007624:KB Cells; D000432:Methanol; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal; D013212:Staphylococcus epidermidis / Q000187:drug effects; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity
D000900:Anti-Bacterial Agents; D002298:Cardenolides; D003603:Cytotoxins; D010936:Plant Extracts; D013729:Terpenes; D000432:Methanol