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A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline

✍ Scribed by Stadler, Richard ;Zenk, Meinhart H.

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
830 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The label from (S)‐[1‐^13^C]norcoclaurine and (S)‐[1‐^13^C]co‐claurine was highly and nonrandomly incorporated into (S)‐reticuline in benzyltetrahydroisoquinoline‐producing plant cell cultures of Berberis stolonifera, Eschscholtzia californica and Peumus boldus. From the intermediates observed in vivo we conclude that (S)‐norcoclaurine is stereoselectively metabolized to (S)‐reticuline via (S)‐coclaurine, (S)‐N‐methylcoclaurine and (S)‐3′‐hydroxy‐N‐methylcoclaurine. These results confirm a revised pathway to the benzylisoquinoline alkaloids.

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