β-Phenylethylamines and the isoquinoline alkaloids

Abstract

Berberis bo (23) 'viana' aromoline, berbamine, berbamunine, homoaromoline, isotetrandrine, obaberine, obamegine, oxyacanthine, patagonine, and thalrugosine aromoline, berbamine, isotetrandrine, and oxyacanthine aromoline, belarine, berbilaurine* ( 16), homoaromoline, lauberine, 7-O-demethyli~othalicberine~ and thalrugosine Berberis paucidentata" berbamine, isotetrandrine, obaberine, and oxyacanthine Berberis p01ymorpha~~ thalrugosine Cyclea r a ~e r n o s a ~~ cycleaneonine* (1 7 ) Guatteria guianensi~~~. 55 apateline, 1,2-dehydroapateline, aromoline, coclobine, daphnandrine, daphnoline, guattamine* (1 8), guattaminone* (19), 2'-norfuniferine* (20; R = Me), 2'-norguattaguianine (21 ; R = Me), 2,2'-bisnorguattaguianine (21 ; R = H), 12-O-dernethylcoclobine* (22), telobine, 1,2-dehydrotelobine, tiliageine, and 2'-nortiliageine* (20; R = H) auroamine* (23; R = Me), and marournine* (23; R = H) berbamine and isotetrandrine phaeanthine 2'-a-N-oxide* (24), and pycnanthine* (25) Berberis bumeliaefolia" Berberis laurina" Gyrocarpus arneri~anus~~ Isopyrum thalictroidesg Pycnarrhena manillensis5' 8 Azaberberines Cyclization of the dihydroisoquinolinium salt (60; R' = Me, R2 = Bz) has yielded the enamine (61), reduction of which furnished ( +_ )-alamaridine (62) and its epimer.13' This synthesis is identical with one previously r e ~0 r t e d . l ~~ Repetition of these reactions starting with (60; R' = Bz, R2 = Me) afforded an isomer of a1arna~idine.l~~ 9 Secoberberines Procumbine has been isolated from Hypecoum Ieptocarpum and from Hypecoum procumbens.

Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

“…Secoberberines such as 5 ′ and 7 are structurally unique and are currently commercially inaccessible. Thus, few studies have been conducted on secoberberine-based drug development 39 40 41 42 43 44 45 46 . In addition, the structure of 7 synthesized by CYP82X1 has not been confirmed due to the lack of authentic standards and limited quantity of the compound achieved in the in vitro investigations 47 .…”

“…Noscapine is a phthalideisoquinoline alkaloid synthesized from L -tyrosine through scoulerine 36 , and the biosynthesis scheme involves multiple types of alkaloids, including 1-benzylisoquinoline, protoberberine and secoberberine alkaloids 37 38 . Among them, secoberberine alkaloids exhibit a unique structural scaffold, but their pharmacological activities are less investigated than alkaloids such as 1-benzylisoquinoline, protoberberine or phthalideisoquinoline alkaloids 39 40 41 42 43 44 45 46 , which may be due to limited access to these molecules.…”