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

R W Teng; D McManus; J Aylward; Steven Ogbourne; J Johns; P G Parsons; A Bacic

doi:10.1016/j.fitote.2009.02.001

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

Journal article

Peer reviewed

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

R W Teng, D McManus, J Aylward, Steven Ogbourne, J Johns, P G Parsons and A Bacic

Fitoterapia, Vol.80(4), pp.233-236

2009

DOI: https://doi.org/10.1016/j.fitote.2009.02.001

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Abstract

Candida antarctica Lipase B

Acylation

3-O-angeloylingenol

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.

Details

Title: Regioselective acylation of 3-O-angeloylingenol by Candida antarctica Lipase B
Authors: R W Teng (Author) - University of Melbourne
D McManus (Author) - Tridan-Albright Ltd. and Wilson (Aust) Ltd. Partnership
J Aylward (Author) - Peplin Ltd.
Steven Ogbourne (Author) - Peplin Ltd.
J Johns (Author) - Queensland Institute of Medical Research
P G Parsons (Author) - Queensland Institute of Medical Research
A Bacic (Author) - University of Melbourne
Publication details: Fitoterapia, Vol.80(4), pp.233-236
Publisher: Elsevier BV
Date published: 2009
DOI: 10.1016/j.fitote.2009.02.001
ISSN: 1971-551X; 1971-551X
Organisation Unit: School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering; Centre for Bioinnovation
Language: English
Record Identifier: 99449881602621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Medicinal; Integrative & Complementary Medicine; Pharmacology & Pharmacy