Glycosylation of capsaicinoids with Panax ginseng stimulated by salicylic acid.
The efficient production of β-glycosides of capsaicin and 8-nordihydrocapsaicin by cultured cells of Panax ginseng is reported. Capsaicin 4-O-(6-O-β-D-xylopyranosyl)-β-D-glucopyranoside (β-primeveroside, 12%) together with capsaicin 4-O-β-D-glucoside (6%) was isolated from the cell suspension of P. ginseng after one week of incubation with capsaicin. On the other hand, 8-nordihydrocapsaicin was glycosylated to 8-nordihydrocapsaicin 4-O-β-D-glucoside (5%) and 8-nordihydrocapsaicin 4-O-β-primeveroside (9%) by P. ginseng. Pretreatment of the cultured cells with salicylic acid greatly enhanced the glucosylation activity toward capsaicinoids. When 500 μM of salicylic acid was added to the cultures prior to the addition of substrate, capsaicin was converted into capsaicin 4-O-β-D-glucoside (17%) and capsaicin β-primeveroside (21%) and 8-nordihydrocapsaicin was glycosylated to 8-nordihydrocapsaicin 4-O-β-D-glucoside (16%) and 8-nordihydrocapsaicin β-primeveroside (15%).
Sunny Health Co. Ltd., Chuo-ku, Tokyo, Japan.
H
H
Katsuragi
Kei
K
Shimoda
Azusa
A
Ohiro
Hiroki
H
Hamada
D000840:Anisoles / Q000737:chemistry; D001711:Biotransformation; D002211:Capsaicin / Q000031:analogs & derivatives / Q000737:chemistry*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D004187:Disaccharides / Q000737:chemistry; D015195:Drug Design; D004353:Drug Evaluation, Preclinical / Q000379:methods; D006031:Glycosylation; D008956:Models, Chemical; D005894:Panax / Q000737:chemistry*; D010944:Plants / Q000187:drug effects / Q000378:metabolism; D020156:Salicylic Acid / Q000737:chemistry*; D013997:Time Factors
D000840:Anisoles; D004187:Disaccharides; C096643:methylursubin; D020156:Salicylic Acid; C517386:nordihydrocapsaicin; D002211:Capsaicin