Steroids with anti-inflammatory activity from Vernonia nigritiana Oliv. & Hiern.
The leaves of Vernonia nigritiana Oliv. & Hiern. (Asteraceae) were investigated for their in vivo topical anti-inflammatory properties, following a bioassay-oriented fractionation approach. Petroleum ether, chloroform and chloroform-methanol extracts inhibited the Croton oil-induced ear dermatitis in mice. The chloroform extract was only about half as active as the non steroidal anti-inflammatory drug indomethacin (ID50=237 and 93 μg/cm(2), respectively). Phytochemical investigation of this extract led to the isolation of nine polyhydroxylated stigmasterol glycosides and six polyhydroxylated stigmasterols. Their structures were elucidated by NMR, MS and chemical methods. Each compound exerted a significant anti-oedema activity, the most active being 1 (3β-O-β-D-glucopyranosyloxy-5α-stigmasta-7,9(11),24(28)Z-triene-6β,16β,26,29-tetrol) and 3 (3β-O-β-D-glucopyranosyloxy-5α-stigmasta-7,9(11),24(28)Z-triene-6β,16β,29-triol), only two and five fold less potent than the steroidal drug hydrocortisone (ID50=0.10, 0.21 and 0.04 μmol/cm(2), respectively). Compound 1 (50 μM) also completely inhibited the transcription factor NF-κB in vitro.
Department of Science, University of Basilicata, 85100 Potenza, Italy.
Antonio
A
Vassallo
Nunziatina
N
De Tommasi
Irmgard
I
Merfort
Rokia
R
Sanogo
Lorella
L
Severino
Marco
M
Pelin
Roberto
R
Della Loggia
Aurelia
A
Tubaro
Silvio
S
Sosa
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000494:pharmacology; D003436:Croton Oil / Q000494:pharmacology; D003872:Dermatitis / Q000188:drug therapy; D004423:Ear / Q000473:pathology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006854:Hydrocortisone / Q000494:pharmacology; D007213:Indomethacin / Q000494:pharmacology; D008302:Mali; D051379:Mice; D015394:Molecular Structure; D016328:NF-kappa B / Q000032:analysis; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D013265:Stigmasterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D035741:Vernonia / Q000737:chemistry*
D000893:Anti-Inflammatory Agents; D006027:Glycosides; D016328:NF-kappa B; D003436:Croton Oil; D013265:Stigmasterol; D006854:Hydrocortisone; D007213:Indomethacin
Anti-inflammatory activity; Asteraceae; Croton oil ear test; NF-κB; Steroids; Vernonia nigritiana