title: Unusual immuno-modulatory triterpene-caffeates in the skins of russeted varieties of apples and pears.
abstract: Three triterpene-caffeates have been isolated from skins of a russeted apple cultivar "Merton Russet" and identified by LC-MS and NMR as betulinic acid-3-cis-caffeate, betulinic acid-3-trans-caffeate, and oleanolic acid-3-trans-caffeate. Betulinic acid-3-trans-caffeate and oleanolic acid-3-trans-caffeate were also found in russeted pear skins. These compounds have not been previously reported in apples or pears, or in any other foods. Their presence was related to suberized tissue as they were only found in russet portions of the partially russeted apple cultivar "Cox's Orange Pippin" and were not detected in the waxy apple cultivar "Royal Gala". High concentrations of betulinic acid-3-trans-caffeate were found in the bark of both "Merton Russet" and "Royal Gala" trees. The three triterpene-caffeates showed anti-inflammatory activity in vitro, inhibiting NF-κB activation with IC50's of 6-9 μM. Betulinic acid-3-trans-caffeate, the predominant compound in the apples, was immuno-modulatory at around 10 μM in the in vitro and ex vivo bioassays, boosting production of the pro-inflammatory cytokine TNFα in cells stimulated with bacterial lipopolysaccharides.
authors: The New Zealand Institute for Plant & Food Research Limited, Mt Albert Research Centre , Private Bag 92 169, Auckland 1142, New Zealand.
authors: Christelle M
authors: CM
authors: Andre
authors: Lesley
authors: L
authors: Larsen
authors: Elaine J
authors: EJ
authors: Burgess
authors: Dwayne J
authors: DJ
authors: Jensen
authors: Janine M
authors: JM
authors: Cooney
authors: Danièle
authors: D
authors: Evers
authors: Jingli
authors: J
authors: Zhang
authors: Nigel B
authors: NB
authors: Perry
authors: William A
authors: WA
authors: Laing
mesh_terms: D000328:Adult; D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D002109:Caffeic Acids / Q000494:pharmacology*; D002460:Cell Line; D005638:Fruit / Q000737:chemistry*; D006801:Humans; D008264:Macrophages / Q000187:drug effects / Q000276:immunology; D027845:Malus / Q000737:chemistry*; D008875:Middle Aged; D016328:NF-kappa B / Q000276:immunology; D010936:Plant Extracts / Q000494:pharmacology*; D031989:Pyrus / Q000737:chemistry*; D014315:Triterpenes / Q000494:pharmacology*
chemical_list: D000893:Anti-Inflammatory Agents; D002109:Caffeic Acids; D016328:NF-kappa B; D010936:Plant Extracts; D014315:Triterpenes; C040048:caffeic acid