Hydrastis canadensis L.

Norlaudanosoline [166) R = H] has for a long time been regarded, in schematic terms, as the biogenetic precursor of the isoquinoline alkaloids, and since it is now known158 that noradrenaline [(167) R = OH] is incorporated into berberastine (168) in Hydrastis canadensis L., presumably via 4-hydroxynorlaudanosoline [(166) R = OH], it is possible159 that a series of alkaloids exists based on 166 (R = OH) as parent. It is significant in this context that the alkaloids imenine... 

This alkaloid has been isolated recently in very small yield from the much investigated plant, Hydrastis canadensis L. (57). Analysis of the iodide indicated the molecular formula C20H18O5N I . It contains two methoxyls and a methylenedioxy group, one hydroxyl function, and is optically active ([a]D+107°). The UV-spectrum of berberastine is typical of a protoberberine alkaloid and its near relationship to berberine was suggested from its IR-spectrum which, apart from the presence of hydroxyl absorption, closely resembled that of berberine iodide. 

Spenser and co-workers 123) have investigated the biosynthesis of berberine and related alkaloids elaborated by Hydrastis canadensis L. In separate feeding experiments, D-glucose-i C (uniformly labeled), DL-phenylalanine-2-i4C, DL-tyrosine-2-i4C DL-tyrosine-S-i C, and 3,4-dihydroxy-2-phenylethylamine-l-i4C (dopamine) were administered to the growing plants. Of the compounds tested tyrosine was the most efficient precursor of the major alkaloids, berberine and hydrastine, and dopamine was almost as good. Glucose was a much less efficient precursor, and the incorporation of phenylalanine into these alkaloids was almost negligible. 

Biosynthesis of hydrastine was followed by administering labeled dopamine 28-30), tyrosine 29-31), phenylalanine 29, 31) and methionine 32) to Hydrastis canadensis L. Two moles of tyrosine 30) but only 1 mole of dopamine were utilized 30). The lactone carbonyl group, the methylenedioxy group, and the N-methyl as well as the 0-methyl groups are derived from labeled formate and methionine 32). 

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). 

Flydrastis rhizoma Golden seal root Hydrastis canadensis L. Ranunculaceae MD... 

Hydrastis. Golden seal orange root yellow root yellow puccoon Indian turmeric. Dried rhizome and roots of Hydrastis canadensis L, Ranunculaceae, contg not less than 2.5% ether-soluble alkaloids. Habit North America. ConstiL 2-4% hydrastine, 2-3% berberine canadine, volatile oil, resin. 

Mecontn. 6,7-Dlmethoxy-1 (3H)-isobenzofuranone 6,7-dimethaxyphihalide opianyl meconinic acid lactone. C1 H10O, mol wt 194.18. C 61.85%, H 5.19%, O 32.96%. Isolated from opium by Dublanc in 1832. Occurs also in the root of Hydrastis canadensis L., Ranunculaceae Freund,... 

Hydrastine, which occurs along with berberine and canadine in Hydrastis canadensis L. (golden-seal), is closely related to the minor opium alkaloit narcotine. At one time, it found hmited use as a bitter stomachic, and was employed in catarrhal conditions because of a rather obscure action on mucous membranes. It exerts a stimulant action on the uterus and has been advocated for the management of postpartum hemorrhage. It has been dropped, however, from the United States Pharmaco-... 

Snow, Joanne Marie. "Hydrastis canadensis L. (Ranunculaceae)." Protocol Journal of Botanical Medicine, vol. 2, no. 2, 1997. Lists multiple abstracts of clinical trials and laboratory studies mostly on berberine. 

Hydrastine, C21H21O6N, is conveniently separated from the mother liquors of plant extracts from which the associated berberine has first been removed as sulfate. It was first encountered in Hydrastis canadensis L. 

Hydrastis canadensis L. Goldenseal Rhizome, roots Gastrointestinal diso-ders, respiratory infections Hydrastine, berberine, canadine... 

Inbaraj, J.J. et ah. Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Paknatine, hydrastine, canadine, and hydrastinine, Chem. Res. Toxicol., 19, 739, 2006. 

Tice, R. 1997. Goldenseal (Hydrastis canadensis L.) and two of its constituent alkaloids berberine and hydrastine review of toxicological literature. Research Triangle Park, NC Integrated Laboratory Systems. 

Berberine (2) is a quaternary ammonium salt from the protoberberine class. It is found in several occidental and oriental medicinal plants, including Hydrastis canadensis L. (Ranunculaceae) and Coptis chinensis Branch var. chinensis (Ranunculaceae), also known as Goldenseal and Huanglian, respectively [34],... 

Inbaraj JJ, Kukielczak BM, Bilski P, He YY, Sik RH, Chignell CF (2(X)1) Photochemistry and photocytotoxicity of alkaloids from Goldenseal Hydrastis canadensis L.) 1. Berberine. Chem Res Toxicol 19 739-744... 

Reticuline is a precursor of sinomenine, via sinocutine, in Sino-menium acutum (115). It is also a precursor of berberine (LXI) in Hydrastis canadensis L. and of protopine (LXII) in Dicentra spectabilis (L.) Lem. (116). In the case of the former base the i T-methyl group of reticuline is used to form the berberine carbon (carbon atom 8) of the tetracyclic alkaloid and with the latter base it is found as the same carbon atom in the heterocyclic ring of protopine. By feeding multiple-labeled (+ )-reticuline, as indicated in LXIII, to Chelidonium majus L., it was shown that it is a precursor of chelidonine (LXIV), (— )-stylopine (LXV), and protopine (LXII), and that the labeled atoms are found in the places expected from current biogenetic theories (117). 

Fed to Hydrastis canadensis L. both bases were incorporated into berberine, an indication that they can be methylated to reticuline and that two routes are possible from laudanosoline to reticuline. 

On the other hand, evidence was accumulating showing that the two aromatic units derived from tyrosine were not identical in the step of condensation leading to the benzylisoquinoline structure. This had already been pointed out by Rapoport et al. (223) in a study on the distribution of the radioactivity in the morphine isolated from P. somni-ferum grown in an atmosphere of labeled carbon dioxide. Similar conclusions were reached in an investigation of the biogenesis of hydrastine in Hydrastis canadensis L. fed with labeled tyrosine, where the ratio of the radioactivity of the two carbon atoms representative of the original tyrosine molecules indicated unequal incorporation (224). 

Compositionally 5,6-dihydro-9,10-dimethoxybenzo[g]-l,3-benzodioxolo[5,6-a]quinolizinium, an alkaloid which can be isolated from many plants notably various members of the Berberidaceae (for example, Berberis vulgaris L. and Hydrastis canadensis L.) and consequently a major component of dyes and lake pigments formed from these extracts Merck Index, 1996). Use of dye extracts derived from the so-called Amur cork tree , Phellodendron amurense Rupr. (Rutaceae), which also contains high levels of berberine, have been noted by several authors (see Phellodendron). 

Abdel-Haq, H., Cometa, M.F., Palmery, M. et al. (2000) Relaxant effects of Hydrastis canadensis L. and its major alkaloids on guinea pig isolated trachea. Pharmacol. Toxicol, 87, 218-222. 

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