Hydrastis canadensis, alkaloids

Mahady GB, Pendland SL, Stoia A, Chadwick LR. (2003) In vitro susceptibility of Helicobacter pylori to isoquinoline alkaloids from Sanguinaria canadensis and Hydrastis canadensis. Phytother Res 17 217-221. 

The incorporation of dopa (60) has been further studied by examining its utilization in the formation of berberine (66) and hydrastine (67) in Hydrastis canadensis, corydaline (68) and protopine (70) in Corydalis solida, and ochotensimine (71) and protopine (70) in C. ochotensis.20 [2-14C]Dopa [as (60)] was again found to label only the isoquinoline moiety of these alkaloids (label is shown by ). 

Even given that the formation of (-) reticuline cannot be blocked, there may be opportunities to block the biochemical sequences leading to thebaine, or even to splice in mechanisms leading to nonaddictive alkaloids produced from (-) reticuline by other plants—for example, berberine ex Hydrastis canadensis or protopine ex Fumaria officinalis. 

Schieffer, G. and Kohn, M. 2002. HPLC assay of Echinacea purpurealGolAtustal (Hydrastis canadensis) combination formulations for the phenolic acids, alkylamides, alkaloids. J. Liq. 

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... 

An alkaloid obtained from hydrastis, the dried rhizome and roots of golden seal, Hydrastis canadensis (Ranunculaceae). Crystals. M.p. 132°. 

The root of Hydrastis canadensis (golden seal) contains isoquinoline alkaloids, including the quaternary base berberine and the tertiary base hydrastine. As the latter can stimulate uterine contractions, it is prudent to avoid golden seal root during pregnancy, even though the actual risk of premature labor still has to be verified. 

Chadwick, L.R. Wu, C.D. Kinghom, A.D. Isolation of alkaloids from goldenseal Hydrastis canadensis rhizomes) using pH-zone-refming countercurrent chromatography. J. Liq. Chromatogr. Relat. Technol. 2001, 24 (16), 2445-2453. 

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. 

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). 

Two indigenous American plants, Sanguinaria canadensis and Hydrastis canadensis, used traditionally by the Native American Indians for the treatment of gastrointestinal ailments, are also active against HP [86]. Methanol extracts of the rhizome or suspension cell cultures of S. canadensis had an MIC range of 12.5-50.0 Ilg/ml. Three isoquinoline alkaloids were identified in the active fraction. Sanguinarine and chelerythrine, Fig. 7, two benzophenanthridine alkaloids. 

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. 

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. 

Alkaloid from Hydrastis canadensis, Berberis vulgaris and other plants. Yellow needles. M.p. 146 .. Cryst. from H.O with 6HjO, from CHCL with 1 CHCI3. Sol. 22 parts HoO at 20 . Sol. Eton. Spar. sol. CHCli, C Hg. Prac.. insoK EtjO. Optically inactive. Zn 4-HgSOg —> tetrahydroberberine. 

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. 

The active principle of goldenseal Hydrastis canadensis, Ranunculaceae) is ( — )-3-hydrastine (88), a phthalideisoquinoline alkaloid. Hydrastis has long been used as a medicinal plant and is used to tteat inflammation of the mucous membranes (Tyler et al., 1981). 

Berberine is a protoberberine alkaloid whose salts form yellow crystals. It is found along with related alkaloids in Hydrastis canadensis, goldenseal, (family Ranunculaceae) Berberis spp. (family... 

Combination of DESI MS with TLC separation was proposed for the first time by Van Berkel et al. [1]. In their study, apart from showing the possibility of such connection, the authors demonstrated practical application of this method during analyses of the FD C dyes (food dyes) and a mixture of aspirin, acetaminophen, and caffeine from a tablet of Extra Strength Excedrin. In the following year, this systan was further upgraded and improved by automating the process of analysis [2]. It was then used to separate the Goldenseal (Hydrastis canadensis) and related alkaloids from... 

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