Regioselective acylation of 3-O-angeloylingenol by Candida antarctica Lipase B |
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Authors: | RW Teng D McManus J Aylward S Ogbourne J Johns P Parsons A Bacic |
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Institution: | 1. CRC for Bioproducts, School of Botany, The University of Melbourne, Victoria 3010, Australia;2. CRC for Bioproducts, Tridan-Albright Ltd. and Wilson (Aust) Ltd. Partnership, Victoria 3013, Australia;3. Peplin Ltd., 1 Breakfast Creek Rd, Newstead, Queensland 4006, Australia;4. Queensland Institute of Medical Research, Herston, Queensland 4006, Australia |
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Abstract: | Acylation of 3-O-angeloylingenol (1) with vinyl acetate, vinyl decanoate and vinyl cinnamate, catalyzed by Candida antarctica Lipase B, was investigated. In each case, compound 1 was quantitatively and regioselectively acylated to afford a single product, 3-O-angeloyl-20-O-acetylingenol (1a), 3-O-angeloyl-20-O-decanoylingenol (1b) and 3-O-angeloyl-20-O-cinnamoylingenol (1c), respectively. The structures of the novel compounds 1b–1c were determined by MS and NMR, and product 1a by comparison of RP-HPLC and TLC with a standard. Compounds 1b–1c induced a bipolar morphology of MM96L melanoma cells at a similar concentration as compound 1, as well as having activity in inhibiting the growth of MM96L melanoma cells. |
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Keywords: | Candida antarctica Lipase B Acylation 3-O-angeloylingenol |
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