Berberis laurina

The isolation of hydrastine from Hydrastis canadensis L. and its separation from other alkaloids were reexamined (229-232). Following several communications concerning the isolation of hydrastine from Berberis laurina Thunb. (233-235) it appears that this alkaloid is, after all, not present (236, 237). Hydrastine picrate has been described (238) and the degradation of its V-oxide has been studied (22). 

Berberis laurina (Thunb.) Bilibg. (Berb daceae)[ 18)... 

Berberis laurina (Thunb.) Bilibg. (Berb daceae)[337] Berberis paucidentata Rusby. (Berberidaceae) 18] Berberis pseudambalaia (Berberidaceae)[230]... 

There are five alkaloids that arc characterized by having 8,S stereochemistry. Three of the bases are diphenolic and two are triphenolic, with each of the bases being bis N-methyl derivatives. Four of the five alkaloids ate phenolic at C(7), while three of the bases arc phenolic at either C(I2) and/or C(7 ). Only two of the alkaloids ate phenolic at C(6 ), and none of the compounds are phenolic at C(6). Berbamunine (1) has been isolated from thirty-one different Berberis species (Berberidaceae), but only one Pseudoxandra species (P. sclerocarpa) (Annonaceae), and one Stephania species (S. p/emi)(Menispennaceae). Espinidine (8) and espinine (9) have been isolated from Berberis laurina, while the latter alkaloid is also a constituent of B. chilensis. Temuconine (251) is a metabolite of only Berberis valdiviana, while thaligrisine (252) has only been found in Pseudoxandra sclerocarpa (Annonaceae) and Thalicirum minus L. var. microphyllum (Ranunculaceae). 

The four alkaloids of this subgroup differ only in their substitution at C(7) and C(12). There are no nor-alkaloids in the series. The fully methoxylated alkaloid of the subgroup is O-methylisothalicberine (94), a compound that has only been isolated from two species of the genus Berberis (B. chilensis and B. laurina) (Berberidaceae). Monophenolic relatives of this alkaloid are belarine (93)[C(7) phenol] and isothalicberine [C(12) phenol], the former of which has only been isolated from Berberis laurina (Berberidaceae) while the latter has only been found as a metabolite of B. chilensis. Finally, the bisphenolic (C(7) and C(12)] alkaloid 7-0-demethylisothalicberine (195) has been found in Berberis chilensis and B. laurina. 

The fully methoxylated parent alkaloid of this subgroup is lauberine (106), which is a metabolite of Berberis laurina (Berberidaceae). Berbilaurine (275X6-demethyllauberine) has also only been found in Berberis laurina, but 12-0-desmethyllauberine (294) has only been isolated from Berberis chilensis. It appears that the alkaloids of this small stereochemical subgroup are restricted in distribution to the genus Berberis (Berberidaceae). 

New alkaloids reported in the period under review include thalsimidine, which is 5-0-desmethylthalsimine, from Thalictrum simplex, espinine (45 R = H) and espinidine (45 R = Me), from Berberis laurina penduline, which is an optical isomer of pycnamine, from Cocculus pendulus," coclobine (46), from Cocculus trilobus, and the mixed benzylisoquinoline-aporphine base... 

P-Hydrastine ((-)-Hydrastine) (/-Hydrastine) 118-08-1 Berberis laurina. B. vulgaris Cotydalis stricta Fumaria bastardii, F. indica, F. parviflora, F. vaillantii Hydrastis canadensis [179, 208, 221, 231- 235]... 

A useful method for labelling the site of the diphenyl ether linkage has been developed in connection with the structural elucidation of the new bisbenzyliso-quinoline ( —)-belarine (40), isolated from the bark of Berberis laurina Billb. (Berberidaceae) the sodium cleavage is carried out in An alternative... 

More recently it has been found in Berberis laurina Billb. (164, 165, 166), in which it may occur to the extent of 1.4%. In H. canadensis the content varies from about 1.5 to 3.9% (167, 168). It is chiefly present in the rhizomes, with less amounts in the leaves and rootlets (169, 170), and only traces in the unripe seeds (169). 

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