Isolation and absolute configuration of new bioactive marine steroids from Euryspongia n. sp.
The apolar fraction of the crude alcoholic extract of the sponge Euryspongia n. sp. was shown to display anti-inflammatory activity. Bioassay guided chromatographic purification led to the isolation of a known compound petrosterol (1) of 3beta-hydroxy-24-norchol-5-en-23-oic acid (2), which has never yet been found as a natural substance, and of a new steroid, 3beta-hydroxy-26-norcampest-5-en-25-oic acid (3). The absolute configurations of 2 and 3 were deduced from comparative 1H NMR data of the (S)- and (R)-phenylglycine methyl ester derivatives. These compounds were evaluated for their anti-inflammatory activity against 6-keto-prostaglandinF1alpha release in a human keratinocyte cell line HaCaT.
Mandeau
Anne
A
UMS CNRS-Pierre Fabre 2597, Institut de Recherche Pierre Fabre, 3 rue Ariane, 31527 Ramonville, France.
Debitus
Cecile
C
Ariès
Marie-Françoise
MF
David
Bruno
B
D015121:6-Ketoprostaglandin F1 alpha / Q000378:metabolism; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002460:Cell Line; D006801:Humans; D015603:Keratinocytes / Q000166:cytology; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013261:Sterols / Q000302:isolation & purification
D000893:Anti-Inflammatory Agents; D013256:Steroids; D013261:Sterols; D015121:6-Ketoprostaglandin F1 alpha; C026361:petrosterol