title: Isolation and absolute configuration of new bioactive marine steroids from Euryspongia n. sp.
abstract: 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.
authors.affiliation: UMS CNRS-Pierre Fabre 2597, Institut de Recherche Pierre Fabre, 3 rue Ariane, 31527 Ramonville, France.
authors.forename: Anne
authors.initials: A
authors.lastname: Mandeau
authors.forename: Cecile
authors.initials: C
authors.lastname: Debitus
authors.forename: Marie-Françoise
authors.initials: MF
authors.lastname: Ariès
authors.forename: Bruno
authors.initials: B
authors.lastname: David
mesh_terms: 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
chemical_list: D000893:Anti-Inflammatory Agents; D013256:Steroids; D013261:Sterols; D015121:6-Ketoprostaglandin F1 alpha; C026361:petrosterol