title: Irbic acid, a dicaffeoylquinic acid derivative from Centella asiatica cell cultures.
abstract: 3,5-O-dicaffeoyl-4-O-malonilquinic acid (1) (irbic acid) has been isolated for the first time from cell cultures of Centella asiatica and till now it has never been reported to be present in the intact plant. Evidence of its structure was obtained by spectroscopic analyses (MS/NMR). Besides 1, cell cultures produce also the known 3,5-O-dicaffeoylquinic acid, chlorogenic acid, and the triferulic acid 2 (4-O-8'/4'-O-8″-didehydrotriferulic acid). Biological activities were evaluated for compound 1, which showed to have a strong radical scavenging capacity, together with a high inhibitory activity on collagenase. This suggests a possible utilization of this substance as a topical agent to reduce the skin ageing process.
authors.affiliation: Università di Bologna, Dipartimento di Biologia Evoluzionistica Sperimentale, Bologna, Italy.
authors.forename: Fabiana
authors.initials: F
authors.lastname: Antognoni
authors.forename: Nicoletta Crespi
authors.initials: NC
authors.lastname: Perellino
authors.forename: Sergio
authors.initials: S
authors.lastname: Crippa
authors.forename: Roberto
authors.initials: R
authors.lastname: Dal Toso
authors.forename: Bruno
authors.initials: B
authors.lastname: Danieli
authors.forename: Anacleto
authors.initials: A
authors.lastname: Minghetti
authors.forename: Ferruccio
authors.initials: F
authors.lastname: Poli
authors.forename: Giovanna
authors.initials: G
authors.lastname: Pressi
mesh_terms: D018929:Cell Culture Techniques; D028041:Centella / Q000737:chemistry*; D017364:Collagenases / Q000187:drug effects* / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: C570368:3,5-O-dicaffeoyl-4-O-malonilquinic acid; D004791:Enzyme Inhibitors; D016166:Free Radical Scavengers; D010936:Plant Extracts; D011801:Quinic Acid; D017364:Collagenases