Affiliation:
1. Department of Biomedical Chemistry, Faculty of Medicine, Oita University, Oita, Japan
2. Department of Life Science, Faculty of Science, Okayama University of Science, Kita-ku, Okayama, Japan
Abstract
Abstract
The biotransformations of capsaicin and dihydrocapsaicin were investigated using cultured plant cells of Phytolacca americana as biocatalysts. Four products, ie 15-hydroxycapsaicin, dihydrocapsaicin, 15-hydroxydihydrocapsaicin, and capsaicin 4-β-glucoside, were isolated from the suspension cultures of P. americana treated with capsaicin for 3 days, showing that capsaicin was regioselectively hydroxylated, reduced, and glucosylated by cultured P. americana cells. On the other hand, dihydrocapsaicin was regioselectively dehydrogenated, hydroxylated, reduced, and glucosylated to give four products, ie capsaicin, 15-hydroxycapsaicin, 15-hydroxydihydrocapsaicin, and capsaicin 4-β-glucoside, by cultured P. americana cells. In this paper, it is reported, for the first time, that dihydrocapsaicin is converted into 15-hydroxydihydrocapsaicin by plant cultured cells.
Funder
Tojuro Iijima Foundation for Food Science and Technology
Publisher
Oxford University Press (OUP)
Subject
Organic Chemistry,Molecular Biology,Applied Microbiology and Biotechnology,General Medicine,Biochemistry,Analytical Chemistry,Biotechnology
Reference42 articles.
1. Intra-cellular distributions of enzymes and intermediates involved in biosynthesis of capsaicin and its analogs in Capsicum-annuum-var-annuum cultivar;Fujiwake;Agric Biol Chem,1982
2. Capsaicinoid formation in the protoplast from the placenta of Capsicum-annuum-var-annuum cultivar Karayatsubusa fruits;Fujiwake;Agric Biol Chem,1982
3. Biotransformation of digitoxigenin by cell suspension cultures of Strophanthus gratus;Furuya;Phytochemistry,1988
4. Glycosylation of 2-phenylpropionic acid and its ethyl ester in suspension cultures of Nicotiana tabacum, Dioscoreophyllum cumminsii and Aconitum japonicum;Furuya;Phytochemistry,1987
5. Biotransformation of phenylacetic acid and 2-phenyl-propionic acid in suspension culture of Coffea arabica;Furuya;Phytochemistry,1988