Regioselective acylation of 3-O-angeloylingenol by Candida antarctica Lipase B

• Published in: Fitoterapia
• Main Authors: R.W. Teng, D. McManus, J. Aylward, S. Ogbourne, J. Johns, P. Parsons, A. Bacic
• Other Authors: G Appendino
• Format: Article in Journal/Newspaper
• Language: English
• Published: Elsevier BV 2009
• Subjects: Candida antarctica Lipase B; 3-O-angeloylingenol; Acylation; C1; 970106 Expanding Knowledge in the Biological Sciences; 0601 Biochemistry and Cell Biology; Antarc*; Antarctica
• Online Access: https://espace.library.uq.edu.au/view/UQ:201189

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.