Glycosylation of capsaicin and 8-nordihydrocapsaicin by cultured cells of Catharanthus roseus

In addition to glucosides 3 and 6, four disaccharides 4, 5, 7, and 8 were isolated from the cell suspension of Catharanthus roseus after incubation with capsaicin ( 1) and 8-nordihydrocapsaicin ( 2). The glycosylation of capsaicin and 8-nordihydrocapsaicin was investigated using cultured cells of Ca...

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Bibliographic Details
Published in:	Phytochemistry (Oxford) Vol. 68; no. 10; pp. 1391 - 1396
Main Authors:	Shimoda, Kei, Kwon, Soonil, Utsuki, Akiko, Ohiwa, Shingo, Katsuragi, Hisashi, Yonemoto, Naoko, Hamada, Hatsuyuki, Hamada, Hiroki
Format:	Journal Article
Language:	English
Published:	Amsterdam Elsevier Ltd 01-05-2007 Elsevier
Subjects:	8-Nordihydrocapsaicin Apocynaceae Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Biotransformation Capsaicin Capsaicin - analogs & derivatives Capsaicin - chemistry Capsaicin - metabolism Catharanthus - metabolism Catharanthus roseus Cells, Cultured cultured cells Cultured plant cells Fundamental and applied biological sciences. Psychology Glycosylation Methods. Procedures. Technologies plant biochemistry Plant physiology and development secondary metabolites Tissue cultures, protoplasts β-Glucoside β-Primeveroside β-Vicianoside Apocynaceae β-Glucoside β-Primeveroside β-Vicianoside Capsaicin 8-Nordihydrocapsaicin Cultured plant cells Catharanthus roseus Glycosylation Cell culture Glucoside Dicotyledones Biotransformation Angiospermae Spermatophyta
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Summary:	In addition to glucosides 3 and 6, four disaccharides 4, 5, 7, and 8 were isolated from the cell suspension of Catharanthus roseus after incubation with capsaicin ( 1) and 8-nordihydrocapsaicin ( 2). The glycosylation of capsaicin and 8-nordihydrocapsaicin was investigated using cultured cells of Catharanthus roseus. In addition to capsaicin 4- O-β- d-glucopyranoside (170 μg/g fr. wt of cells), the biotransformation products, capsaicin 4- O-(6- O-β- d-xylopyranosyl)-β- d-glucopyranoside (116 μg/g fr. wt of cells) and capsaicin 4- O-(6- O-α- l-arabinopyranosyl)-β- d-glucopyranoside (83 μg/g fr. wt of cells), were isolated from the cell suspension after three days of incubation with capsaicin. Two other compounds, 8-nordihydrocapsaicin 4- O-(6- O-β- d-xylopyranosyl)-β- d-glucopyranoside (171 μg/g fr. wt of cells) and 8-nordihydrocapsaicin 4- O-(6- O-α- l-arabinopyranosyl)-β- d-glucopyranoside (122 μg/g fr. wt of cells), together with the known 8-nordihydrocapsaicin 4- O-β- d-glucopyranoside (204 μg/g fr. wt of cells) were also isolated from the cell suspension after incubation with 8-nordihydrocapsaicin.
Bibliography:	http://dx.doi.org/10.1016/j.phytochem.2007.03.005 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0031-9422 1873-3700
DOI:	10.1016/j.phytochem.2007.03.005