Enzymatic preparation of 20(S, R)-protopanaxadiol by transformation of 20(S, R)-Rg3 from black ginseng.
20(S)-protopanaxadiol (PPD(S)) and 20(R)-protopanaxadiol (PPD(R)), the main metabolites of ginsenosides Rg3(S) and Rg3(R) in black ginseng, are potential candidates for anti-cancer therapy due to their pharmacological activities such as anti-tumor properties. In the present study, we report the preparation of PPD(S, R) by a combination of steaming and biotransformation treatments from ginseng. Aspergillus niger was isolated from soil and showed a strong ability to transform Rg3(S, R) into PPD(S, R) with 100% conversion. Furthermore, the enzymatic reactions were analyzed by reversed-phase HPLC, showing the biotransformation pathways: Rg3(S)-->Rh2(S)-->PPD(S) and Rg3(R)-->Rh2(R)-->PPD(R), respectively. In addition, 12 ginsenosides including 3 pairs of epimers, namely Rg3(S), Rg3(R), Rh2(S), Rh2(R), PPD(S) and PPD(R), were simultaneously determined by reversed-phase HPLC. Our study may be highly applicable for the preparation of PPD(S) and PPD(R) for medicinal purposes and also for commercial use.
Liu
Lei
L
Department of Food Science and Technology, College of Agriculture and Biotechnology, Chungnam National University, Daejon 305-764, Republic of Korea.
Zhu
Xue-Mei
XM
Wang
Qi-Jun
QJ
Zhang
Dong-Liang
DL
Fang
Zhe-Ming
ZM
Wang
Chun-Yan
CY
Wang
Zhen
Z
Sun
Bai-Sheng
BS
Wu
Hui
H
Sung
Chang-Keun
CK
D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism; D001234:Aspergillus niger / Q000201:enzymology*; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D056148:Chromatography, Reverse-Phase; D036145:Ginsenosides / Q000737:chemistry* / Q000378:metabolism*; D005894:Panax / Q000378:metabolism*; D012502:Sapogenins / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D036145:Ginsenosides; D012502:Sapogenins; C097367:ginsenoside Rg3; C062916:protopanaxadiol