Kobata Kenji, Kawaguchi Manami, Watanabe Tatsuo
School of Food and Nutritional Sciences, University of Shizuoka, Japan.
Biosci Biotechnol Biochem. 2002 Feb;66(2):319-27. doi: 10.1271/bbb.66.319.
Capsinoids are a novel group of compounds produced by the Capsicum plant. We synthesized a capsinoid by the lipase-catalyzed esterification of vanillyl alcohol with fatty acid derivatives in an organic solvent. The use of seven out of 17 commercially available lipases, especially Novozym 435, was applicable to the synthesis of vanillyl nonanoate, a model compound of capsinoids. The yield of vanillyl nonanoate under the optimum conditions of 50 mM vanillyl alcohol and 50 mM methyl nonanoate in 500 microl of dioxane, using 20 mg of Novozym 435 and 50 mg of 4 A molecular sieves at 25 degrees C, was 86% in 20 h. Several capsinoid homologues having various acyl chain lengths (C6-C18) were synthesized at 64-86% yields from the corresponding fatty acid methyl ester. The natural capsinoids, capsiate and dihydrocapsiate, were obtained by a 400-fold-scale reaction at these optimum conditions in 60% and 59% isolated yields, respectively.
辣椒素类物质是辣椒属植物产生的一类新型化合物。我们通过脂肪酶催化香草醇与脂肪酸衍生物在有机溶剂中进行酯化反应合成了一种辣椒素类物质。17种市售脂肪酶中有7种，特别是诺维信435，可用于合成辣椒素类物质的模型化合物壬酸香草酯。在500微升二氧六环中，使用20毫克诺维信435和50毫克4A分子筛，在25℃下，50毫摩尔香草醇和50毫摩尔壬酸甲酯的最佳条件下，壬酸香草酯的产率在20小时内为86%。从相应的脂肪酸甲酯以64 - 86%的产率合成了几种具有不同酰基链长度（C6 - C18）的辣椒素类同系物。在这些最佳条件下，通过400倍规模的反应分别以60%和59%的分离产率获得了天然辣椒素类物质辣椒素和二氢辣椒素。
