Berberine from Coptis japonica

Figure 2.6 Biosynthesis of berberine from (5)-reticuline in Berberis species and Coptis japonica. BBE, berberine bridge enzyme SCMT, (5)-scoulerine-9-0-methyltransferase CAS, (5)-canadine synthase STOX, tetrahydroberberine oxidase COX, enzyme found in Coptis japonica.

S)-canadine can act as a substrate for the tetrahydroberberine oxidase (STOX) enzyme isolated from Berberis and may be converted by this enzyme to berberine (Zenk, 1995) however, the oxidase found in Coptis japonica (COX)... 

Occurrence. Worenine Avas isolated from Coptis japonica (164). The base was separated from coptisine by virtue of the greater solubility of its nitrate or sulfate in alcohol or hot water. Worenine, mixed with berberine, Avas thus separated from coptisine, and reduction of this mixture afforded a separable mixture of tetrahydroberberine and tetrahydroworenine, the latter, C20H19NO4, melting at 212-213°. 

Nevertheless in 1985 an oxidase was reported from crude extracts of Coptis japonica cell cultures with different properties as compared to the enzyme from Berberis. This led to a systematic comparison of the two cell cultures concerning the last steps of the berberine biosynthesis. The purified oxidase from... 

Berberine is also obtained from Hydrastis canadensis (Berberidaceae), Coptis japonica (Ranunculaceae), and several other species [1]. Its chemical structure was clarified at the beginning of the twentieth century [2], and the alkaloid was synthesized by several routes [3]. Regarding the many biological activities of berberine, other than antimicrobial activity against Staphyb-coccus aureus, dysentery bacillus, cholera vibrio, and gonococcus organisms, hypertensive, sedative, anti-inflammatory [4], and cytotoxic [5,6] activities are reported. 

S. cerevisiae/6-OMT, coclaurine-NMT, and 3 -hydroxy-N-methylcoclaurine-4 -OMT from CopUs japonica (hydroxylation, cyclization by berberine bridge enzyme from Papaver somnifemm) E. coli or S. cerevisiae/(>-OMT, coclaurine-NMT, and 3 -hydroxy-N-methylcoclaurine-4 -OMT from Coptis japonica (condensation, hydroxylation, cyclization by berberine bridge enzyme from Coptis japonica)... 

Fig. 5 The two step accumulation of berberine from the xylem soap into the vacuole of rhizome cells of Coptis japonica. (Taken with permission from Shitan and Yazaki, 2007...

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