A novel terpenoid indole alkaloid derived from catharanthine via biotransformation by suspension-cultured cells of Catharanthus roseus.
OBJECTIVE
Although catharanthine (1) is well known as a biosynthetic precursor of the anticancer alkaloid, vinblastine, its alternative metabolic pathways are unclear.


RESULTS
Biotransformation of 1 by suspension-cultured cells of Catharanthus roseus gave a new oxidative-cleavage product (2). The structure of 2 was determined as 3-hydroxy-4-imino-catharanthine by spectroscopic methods. Maximum conversion (9.75 %) of 2 was observed after 120 h adding 6 mg of 1/100 ml to 12-day-old suspension-cultured cells of C. roseus. Furthermore, qRT-PCR experiment was performed to reveal the effect of 1 on the expression of the genes in the biosynthetic pathway of TIA 1 up-regulated the transcript level of D4H whilst down-regulating the transcript levels of G10H, LAMT, GES, and IRS.


CONCLUSIONS
A new metabolite of catharanthine, 3-hydroxy-4-imino-catharanthine, is reported.
Biotechnological Institute of Chinese Materia Medica, College of Pharmacy, Jinan University, Guangzhou, 510632, China.
Shuijie
S
He
Department of Natural Products Chemistry, College of Pharmacy, Jinan University, Guangzhou, 510632, China.
Jianhua
J
Zhu
Department of Natural Products Chemistry, College of Pharmacy, Jinan University, Guangzhou, 510632, China. tzjc@jnu.edu.cn.
Jiachen
J
Zi
Biotechnological Institute of Chinese Materia Medica, College of Pharmacy, Jinan University, Guangzhou, 510632, China.
Pengfei
P
Zhou
Biotechnological Institute of Chinese Materia Medica, College of Pharmacy, Jinan University, Guangzhou, 510632, China.
Jincai
J
Liang
Biotechnological Institute of Chinese Materia Medica, College of Pharmacy, Jinan University, Guangzhou, 510632, China. tyrm@jnu.edu.cn.|Department of Natural Products Chemistry, College of Pharmacy, Jinan University, Guangzhou, 510632, China. tyrm@jnu.edu.cn.
Rongmin
R
Yu
D053898:Biosynthetic Pathways / Q000235:genetics; D001711:Biotransformation; D030008:Catharanthus / Q000254:growth & development / Q000378:metabolism*; D002478:Cells, Cultured; D020869:Gene Expression Profiling; D008958:Models, Molecular; D015394:Molecular Structure; D060888:Real-Time Polymerase Chain Reaction; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry / Q000378:metabolism*; D013057:Spectrum Analysis; D014748:Vinca Alkaloids / Q000378:metabolism*
D046948:Secologanin Tryptamine Alkaloids; D014748:Vinca Alkaloids; C017836:catharanthine
3-Hydroxy-4-imino- catharanthine; Biotransformation; Catharanthine; Catharanthus roseus; Suspension-cultured cells; qRT-PCR