Regioselective acylation of 3-O-angeloylingenol by Candida antarctica Lipase B.
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.
Teng
R W
RW
CRC for Bioproducts, School of Botany, The University of Melbourne, Victoria 3010, Australia. tengrongwei@hotmail.com
McManus
D
D
Aylward
J
J
Ogbourne
S
S
Johns
J
J
Parsons
P
P
Bacic
A
A
D000215:Acylation; D000972:Antineoplastic Agents, Phytogenic / Q000378:metabolism* / Q000494:pharmacology / Q000627:therapeutic use; D045744:Cell Line, Tumor; D004224:Diterpenes / Q000378:metabolism* / Q000494:pharmacology / Q000627:therapeutic use; D028481:Euphorbia / Q000737:chemistry*; D005656:Fungal Proteins; D006801:Humans; D008049:Lipase / Q000378:metabolism*; D008545:Melanoma / Q000188:drug therapy*; D010936:Plant Extracts / Q000378:metabolism* / Q000494:pharmacology / Q000627:therapeutic use; D014753:Vinyl Compounds / Q000378:metabolism
C553853:3-O-angeloylingenol; D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D005656:Fungal Proteins; D010936:Plant Extracts; D014753:Vinyl Compounds; D008049:Lipase; C431349:lipase B, Candida antarctica