New compounds from an extract of Vernonia colorata leaves with anti-inflammatory activity.
Bioassay-directed fractionation of an anti-inflammatory CHCl(3)-MeOH (9:1) extract of leaves of Vernonia colorata, using a carrageenan-induced rat paw model, led to the isolation of six new compounds (1-6). These were assigned as two new androst-8-en glycosides, 3-O-[beta-d-galactopyranosyl-(1-2)-[beta-d-glucopyranosyl-(1-->6)]-beta-d-glucopyranoside]-5alpha,14alpha-androst-8-ene (1) and 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside]-5alpha,14alpha-androst-8-ene (2), two new stigmastane-type glycosides, 3beta,21,24-trihydroxy-21,23;22,28;26,28-triepoxy-5alpha-stigmasta-8(9),14(15)-dien-3-O-beta-d-galactopyranosyl-(1-->2)-beta-d-glucopyranoside (3) and 3beta,21,24-trihydroxy-21,23;22,28;26,28-triepoxy-5alpha-stigmasta-8(9),14(15)-dien-3-O-beta-d-galactopyranosyl-(1-->2)-beta-d-(6-acetyl)glucopyranoside (4), and two new stigmastane-type steroids, 3beta,25,29-trihydroxy-5alpha-stigmasta-8(9),14(15),24Z(28)-triene (5) and 3beta,23,25-trihydroxy-24,28-epoxy-5alpha-stigmasta-8(9),14(15)-diene (6). The structures of 1-6 were elucidated by spectral and chemical studies. Compounds 1-6 were tested for the anti-inflammatory activity, but all were inactive or weakly inactive as anti-inflammatory agents.
Cioffi
Giuseppina
G
Dipartimento di Scienze Farmaceutiche, Università di Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy.
Sanogo
Rokia
R
Diallo
Drissa
D
Romussi
Giovanni
G
De Tommasi
Nunziatina
N
D000736:Androstenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008302:Mali; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D013265:Stigmasterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D035741:Vernonia / Q000737:chemistry*
D000736:Androstenes; D000893:Anti-Inflammatory Agents; D006027:Glycosides; D013265:Stigmasterol