Biotransformation of ingenol-3-angelate in four plant cell suspension cultures

R W Teng; D McManus; J Aylward; Steven Ogbourne; D Armstrong; S L Mau; J Johns; A Bacic

doi:10.1080/10242420902811105

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Biotransformation of ingenol-3-angelate in four plant cell suspension cultures

Journal article

Peer reviewed

Biotransformation of ingenol-3-angelate in four plant cell suspension cultures

R W Teng, D McManus, J Aylward, Steven Ogbourne, D Armstrong, S L Mau, J Johns and A Bacic

Biocatalysis and Biotransformation, Vol.27(3), pp.186-194

2009

DOI: https://doi.org/10.1080/10242420902811105

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Abstract

Ingenol-3-angelate

Hordeum vulgare

Oryza sativa

Panax quinquefolium

Nicotiana tabacum

plant cell suspension cultures

Four plant species, Hordeum vulgare, Oryza sativa, Panax quinquefolium and Nicotiana tabacum, grown as cell suspension cultures, were used for the biotransformation of an anticancer compound, ingenol-3-angelate (1). Three compounds (1a-1c) were detected predominantly in the cultured medium and their structures were determined as 16-hydroxy-ingenol-3-angelate (1a), ingenol (1b) and ingenol-5-angelate (1c), based on MS and NMR spectroscopic evidence. 16-Hydroxy-ingenol-3-angelate (1a) was the only compound produced by H. vulgare cell cultures except that, at high substrate concentration (266 mg L-1), 1c was produced with a low yield both in the medium and within cells. In contrast, compounds 1a and 1b were produced in different yields and proportions in the other three cell cultures. The effect of substrate concentration, addition and incubation time on the production of 1a by H. vulgare cell cultures was investigated, and compounds 1a and 1b were assayed to be active in inhibiting the growth and inducing a bipolar morphology of MM96L melanoma cells.

Details

Title: Biotransformation of ingenol-3-angelate in four plant cell suspension cultures
Authors: R W Teng (Author) - University of Melbourne
D McManus (Author) - CRC for Bioproducts
J Aylward (Author) - Peplin Ltd.
Steven Ogbourne (Author) - Peplin Ltd.
D Armstrong (Author) - CRC for Bioproducts
S L Mau (Author) - University of Melbourne
J Johns (Author) - Queensland Institute of Medical Research
A Bacic (Author) - University of Melbourne
Publication details: Biocatalysis and Biotransformation, Vol.27(3), pp.186-194
Publisher: Informa Healthcare
Date published: 2009
DOI: 10.1080/10242420902811105
ISSN: 1024-2422
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: 99450214802621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Biochemistry & Molecular Biology; Biotechnology & Applied Microbiology

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