Berberis alkaloids

Khamidov, I. L, Aripova, S. F. and Karimov, A. K. 2003. Berberis Alkaloids. XLI. Alkaloids from leaves of cultivated Berberis oblonga. Chemistry of Natural Compounds, 39(4) 407. 

K. Drost, M. Szaufer, and Z. Kowalewski, Herba Pol. 20, 301 (1974) Biol. Abstr. 61, 39416. [A review (in Polish) of occurrence of several Berberis alkaloids, containing references to 1972.]... 

Karimov A, AbduUaev ND, Telezhenetskaya MV, Lutfullin K, Yunusov SYu (1976) Oblongjne - a new quaternary alkaloid from Berberis oWonga. Chem Nat Compd 12(1) 111-112 Karimov A, Telezhenetskaya MV, Lutfullin KL, Yunusov SYu (1977) Berberis alkaloids. The new alkaloid oblongamine. Chem Nat Compd 13(l) 68-70... 

Khamidov II, Tashkhodzhaev B, Aripova SF, Telezhenetskaya MV, Karimov AK (1996) Berberis alkaloids. XXXVII. Investigation of the alkaloids of B. oblongata and B. integerrirm. Crystal structure of 8-trichloromethyldihydroberberine. Chem Nat Compd 32(6) 876-879... 

Palmatine, 5,6-dihydro-2,3,9,10-tetramethoxydibenzo[a.g]quino-lizinium, a basic dyestuff, is, along with tetrahydropahnatine, the most widely distributed Berberis alkaloid. It is extracted from the rootbark of Berberis vulgaris L. and Phellodendron amurense Rupr. (Schweppe, 992 Merck Index, 1996)... 

Berberine and other Berberis alkaloids were reported to be toxic to seedlings of dog rose and horse chestnut, causing atrophy. ... 

The following Berberis spp. contain mixtures of alkaloids — B. heteropoda Schrenk. Berberine, palmatine, jatrorrhizine, columbamine, berbamine and oxyacanthine. ... 

Mahonia aquifolium Nutt. Berberis aquifolium Pursh.) Berberine, berbamine, oxyacanthine, a phenolic base, m.p. 190-3°, and undetermined alkaloids. 

The two following alkaloids of unknown constitution have been recorded for Berberis and Mahonia species —... 

The authors suggest that altitudinal variation in phytochemical constituents remains unknown. That this is factually incorrect is revealed by the well-known work on the effect of elevation on cyanogenic glycosides, as shown in the case of the clovers above, as well as in the case of alkaloid variation in Berberis just described. 

Chandra, P. and Purohit, A. N. 1980. Berberine contents and alkaloid profile of Berberis species from different altitudes. Biochem. Syst. Ecol. 8 379-380. 

The reaction of oxyberberine (58) and berberine (15) with dichlorocarbene has been previously reviewed (11). An interesting product was the keto lactam 189, which was obtained from 58 via the adduct 188 (Scheme 34) (105). This product was later isolated from Berberis darwinii and named magallanesine (106) however, this alkaloid has since been shown to be an artifact (107). 

The following secodimeric alkaloids have been isolated from natural sources (+)-hernandaline (197), from Hernandia ovigera L. (158), (—)-natalinine (198) (759), and (+)-coyhaiquine (199) (160), the two latter from Berberis empetrifolia Lam. with the yields 0.00005 and 0.00008%, respectively. Appropriate aporphine-benzylisoquinoline or proaporphine-benzylisoqui-noline dimers are probably precursors of these seco alkaloids, although... 

Secoquettamine (234) and dihydrosecoquettamine (235) together with their probable biogenetic precursor quettamine (236) form a small group of alkaloids. They were isolated by Shamma et at. (179) from Berberis baluchista-nica in yields of 0.00036,0.00017, and 0.0012%, respectively. These alkaloids incorporate either a benzofuran or a dihydrobenzofuran ring within the molecular framework, and the seco ones possess the /V,W-dimethylaminoethyl substituent. The structures of these bases were determined on the grounds of spectral data as well as by total synthesis. There is one chiral center at C in dihydrosecoquettamine (235) however, the base was isolated in the form of a racemic mixture (179). 

Bisbenzylisoquinoline alkaloids are dimeric benzyltetrahydroisoquinoline alkaloids that are known for their pharmacological activities. A well-described example is the muscle relaxant (+)-tubocurarine, which in crude form serves as an arrow poison for South American Indian tribes. In the biosynthesis of this broad class of dimeric alkaloids, it has been postulated that the mechanism of phenol coupling proceeds by generation of phenolate radicals followed by radical pairing to form either an inter- or intramolecular C - O or C - C bond. Enzyme studies on the formation of bisbenzylisoquinoline alkaloids indicated that a cytochrome P-450-dependent oxidase catalyzes C - O bound formation in the biosynthesis of berbamunine in Berberis cell suspension culture.15 This enzyme, berbamunine synthase (CYP80A1), is one of the few cytochromes P-450 that can be purified to... 

N.A. Berberis aquifolium L. Berberine, protoberberine alkaloids, oxyberberine, magnoflorine, columb amine.1 °°.273 -274 For eczema, gall bladder disorder, chronic hepatitis B, gastritis, diarrhea, antipsoriasis. 

These species were also alkaloid-positive Berberis incertus, Epi-medium violaceum, Podophyllum peltatum (3/3). 

The basic fraction of Berberis baluchistanica Ahrendt yielded (+)-bal-uchistine (79), C36H38N206, mp 222-224°C (MeOH), [a]g> +333° (c = 0.075, MeOH). The UV spectrum, max 283 nm (EtOH), showed a shift to 290 nm, typical of a phenolic alkaloid, on addition of base. Reaction of 79 with di-... 

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