Unusual Immuno-Modulatory Triterpene-Caffeates in the Skins of Russeted Varieties of Apples and Pears

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• 作者：Christelle M. Andre ; Lesley Larsen ; Elaine J. Burgess ; Dwayne J. Jensen ; Janine M. Cooney ; Dani猫le Evers ; Jingli Zhang ; Nigel B. Perry ; William A. Laing
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2013
• 出版时间：March 20, 2013
• 年：2013
• 卷：61
• 期：11
• 页码：2773-2779
• 全文大小：321K
• 年卷期：v.61,no.11(March 20, 2013)
• ISSN：1520-5118

文摘

Three triterpene-caffeates have been isolated from skins of a russeted apple cultivar 鈥淢erton Russet鈥?and identified by LC鈥揗S 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 鈥淐ox鈥檚 Orange Pippin鈥?and were not detected in the waxy apple cultivar 鈥淩oyal Gala鈥? High concentrations of betulinic acid-3-trans-caffeate were found in the bark of both 鈥淢erton Russet鈥?and 鈥淩oyal Gala鈥?trees. The three triterpene-caffeates showed anti-inflammatory activity in vitro, inhibiting NF-魏B activation with IC₅₀鈥檚 of 6鈥? 渭M. Betulinic acid-3-trans-caffeate, the predominant compound in the apples, was immuno-modulatory at around 10 渭M in the in vitro and ex vivo bioassays, boosting production of the pro-inflammatory cytokine TNF伪 in cells stimulated with bacterial lipopolysaccharides.

Keywords:

apple; pear; russet; triterpene; betulinic acid; betulinic acid-3-O-caffeate; inflammation; NF-魏B; TNF伪