Alkaloids berberine

Tetrahydroproto-berberine alkaloids Corydalis tashira SiOj CHCI3 + EtOH B + MeOH CHCI3 + AcOEt UV 254 nm Identification 18... 

Indenobenzazepines have been used as key intermediates for synthesis of rhoeadine, protopine, phthalideisoquinoline, and spirobenzylisoquinoline alkaloids. Several new alkaloids possessing an indenobenzazepine skeleton have been isolated, and they are presumably biosynthesized from proto-berberine alkaloids. 

Die Konfiguration des natiirlichen (+)-Laudanosins, sowie verwandter Tetrahy-dro-isochinolin-, Aporphin- und Tetrahydro-berberin-alkaloide, by H. Corrodi and E. Hardegger, Helv. Chim. Acta, 39 (1956) 889-897. 

Futhermore, the photocyclization of the donor-acceptor pair thioether-imide has already been applied to the synthesis of the berberine alkaloid chilinene as an a-key step [252]. 

Acylation of the keto acid (637) leads to the isobenzopyrylium salt (638) (77CHE1183). However, the isobenzopyrylium salt (639), a potential intermediate for the synthesis of analogues of berberine alkaloids, results from the formylation of the substituted ketone or the isochromanone (640) using dichloromethyl butyl ether (Scheme 251) (81CHE221). A second product, the 5-oxoniachrysene (641), is formed and this compound may also be obtained by reaction of the isobenzopyrylium salt with phosphorus pentachloride and then with triethylamine. The intermediacy of a cyclic vinyl ether is proposed. 

Certain berberine alkaloids can also be directly prepared from the appropriately substituted protopine alkaloid by photolysis in ethanol.387 Berberine itself (359) is obtained in this way from a-allocryptopine (360), and similar preparations of epiberberine and coptisine have been recorded. 

This reaction has been used to synthesize the precursors of berberine alkaloids [benzo(c)phenanthridine alkaloids]331. Thus, the photostimulated reaction of oiodoben-... 

The chemistry of berberine has been reviewed.69 Several papers on the pharmacological and biochemical action of derivatives of berberine alkaloids have appeared, including studies of the adrenergic neurone-blocking action of dehydrocorydaline,70 71 the intercalation of coralyne with DNA as a possible mechanism... 

Aporphine and Berberine Alkaloids.—The aporphine alkaloid magnoflorine (42) has been shown to be formed specifically from reticuline (33) in Aquilegia species40... 

Berberine alkaloid Quantum chemical study of dilferent forms by the DFT and MP2 methods ... 

Several new aporphine and berberine alkaloids which were uncovered in the period of the last ten years or so are from plants of the Anixmaceae such as the 7-hydroxyaporphine, dasymachaline (9) from Desmosdasymachatus [27], the dioxoaporphine, l,2,3-trimethoxy-4,5-dioxo-6a,7-dehydroaporphine (10) from Pseuduvaria macrophylla [28], the tetrasubstituted... 

The methyl ester of corydalic acid (413) can be isolated from Covydalis incisa when the plant is in the vegetative stage and can be classed as a secobenzophenanthridine alkaloid (G. Nonaka, T. Kodera and I. Nishioka, Chem.Pharm.Bull., 1973, 21, 1020). It has been synthesised by the condensation of the acid anhydride (410) with the imine (411) to give an acid that is decarboxylated to a mixture of geometrical isomers, of which (412) is hydrolysed, esterified and reduced to ( )-meth-y1 corydalate (413) (Cushman and W.C. Wong, J.org.Chem., 1984, 49, 1278). It has also been prepared by the reduction, oxidation and esterification of the olefin (414), prepared from the berberine alkaloid corysamine (Hanaoka, S. Yoshida and C. Mukai, Chem.Comm., 1984, 1703). 

Various Reactions in the Side-Chains of Thiophens. - The preparation of various iV-substituted thieno[3,2-/]morphans from 2,5-dimethylthieno[3,2-/Jmorphan has been described. Several thiophen isosteres of proto-berberine alkaloids have been prepared, starting from amides between 3-thienylacetic acid and substituted )3-phenylethylamine or 3-(3-thienyl)ethyl-amine, followed by classical cyclization to dihydroisoquinolines, reduction to the tetrahydro system, and Mannich-type reaction with formaldehyde. 

Tour main groups can be identified I) upper clade alkaloids which affect only neuroreceptors (especially inAChR and nACIiR), 2) upper part of clade 2 between inonocrotaline and colchicine alkaloids which bind to adrenergic and serotonin receptors, 3) lower part of clade 2 between ergoinetrine and berberine alkaloids which affect concomitantly neuroreceptors and DNA and correlated targets and 4) alkaloids which do not affect any of the targets tested (i.e. caffeine and tropine). 

Berberine alkaloids synthesis steps, 295-297 Betaines in Wittig olefinations, 29-30 Bicyclic compounds. See Oligocyclic compounds Bicyclic hydrocarbon derivs. pr., 192 Bicyclo[4.1.0]hepta-2,4-dienes rearr., 334 Bicyclo[2.2.1]heptane derivs. pr., 192... 

Recent chemical progress concerning berberine alkaloids (biosynthesis, bioformation with mammalian tissues, syntheses, reactions including... 

In recent years, attention has been paid to the physicochemical properties of the tetrahydroberberine and berberine alkaloids. Three papers have appeared on mass spectrometry of those alkaloids (655-657) and their N-methohalides 658). The mass spectra of 9-methoxytetrahydroproto-berberines show an intense peak which arises by cleavage of the methoxyl... 

The biosynthesis of the spirobenzyltetrahydroisoquinoline alkaloids can proceed from dehydrophthalideisoquinoline alkaloids (161) via the aldehyde 195 (Scheme 65). The latter may, however, also arise by the Hantsch tautometry from berberine alkaloids. By that mechanism a group of Canadian authors succeeded in preparing the analogs corydaine and sibiri-cine (798, 799). 

Theoretical methods have also been used for the study of the UV spectrum of quinolizinium ion and its benzo derivatives <59JCS3654,69G1078,71TCA216>, and also of berberine alkaloids <82CJC970>. 

Photochemical transformations of partially saturated quinolizinium systems have received much attention, particularly in the field of berberine alkaloids. 

A new tetrahydroprotoberbine alkaloid is tetrahydrothalifendine (132), found in Thalictrum fendleri Engelm. ex Gray (Ranunculaceae). The first known dimeric proto berberine alkaloid is bisjatrorrhizine (133), obtained from the root of Jatrorrhiza palmata (Lam.) Miers (Menispermaceae) and synthesized by oxidative dimerization of jatrorrhizine. ... 

Sumitomo Chemical. KK J57144-992. 03-03-8l-JP-030992 (07-09-82). Berberine alkaloid production by culturing calluses from Tinospora (Menispermaceae), separating alkaloid(s), mainly palmatine and/or jatrorrhizine. 

Imaseki, I., Y. Kitabatake, and T. Taguchi. 1961. Studies on the effect of berberine alkaloids on intestine and uterus in mice. Yakugaku Zasshi 81 1281-1284. 

Orfila, L., M. Rodriguez, T. Coknan, et al. 2000. Structural modification of berberine alkaloids in relation to cytotoxic activity in vitro. /. Ethnopharmacol. 71(3) 449-456. 

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