Berberis species

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

In addition to its obvious routine importance, UV spectrophotometry has been used as an assay method the berbamine content of crude ethanolic extracts of 22 Berberis species was determined, with standard deviation 3.83%, by measuring the absorption at 282 nm (171). Thalicarpine was similarly assayed at 280 nm and also by TLC densitometry and titrimetry or potentiometry (308). Tetrandrine was determined in drug preparations by UV spectrophotometry of a dilute HC1 solution at 280 nm (standard deviation 0.40%) (309). 

Several bisbenzylisoquinolines that are found in Berberis species of northern Pakistan can be derived, formally at least, from the naturally occurring spiro-dienone alkaloid pakistanamine (54).48 It is notable that the relative abundance of alkaloids derived by formal dienone-phenol rearrangement in (54) by mechanism (a) is greater than that of more hindered alkaloids formed by mechanism (b). 

A study of three Berberis species, namely B. orthobotrys, B. calliobotrys, and B. zabeliana, has yielded four new aporphine dimers, i.e. chitraline (56), 1-O-methylpakistanine (57),67,68 kalashine (58),68,69 and khyberine (59).70 Kalashine and khyberine are the first aporphine-benzylisoquinoline dimers incorporating a diaryl ether terminal at C-ll of the aporphine moiety. 

Stermitz FR, Matsuda JT, Lorenz P, Mueller P, Zenewicz L, Lewis K (2000) 5 -Methox-yhydnocarpin-D and Pheophorbide A Berberis Species Components that Potentiate Berber-ine Growth Inhibition of Resistant Staphylococcus aureus. J Nat Prod 63 1146... 

Figure 2.6 Biosynthesis of berberine from (5)-reticuline in Berberis species and Coptis japonica. BBE, berberine bridge enzyme SCMT, (5)-scoulerine-9-0-methyltransferase CAS, (5)-canadine synthase STOX, tetrahydroberberine oxidase COX, enzyme found in Coptis japonica.

Barberry is a vernacular name for members of the Berberis species, such as Berberis vulgaris (European barberry), but is also used to refer to members of the Mahonia species, such as Mahonia aquifolium and Mahonia nervosa. In the USA only the latter species have had official status as a source of barberry, but Berberis vulgaris is said to serve similar medicinal purposes and to contain similar principles. Its root bark yields the quaternary isoquinoline alkaloid berberine and several other tertiary and quaternary alkaloids. It has been used to treat a variety of skin conditions (8,9). The literature sometimes cautions that barberry alkaloids can cause arterial hypotension. 

Rhizome and roots Berberis species of Western North the Sect. America... 

The presence of oxyberberine has since been noted to occur in other Berberis species (see Table I), whereas dihydroberberine is so far unique to B. lambertii. 

Recently, it has been demonstrated that medicinal plants contain MDR pump inhibitors that actually enhance the activity of their own natural antimicrobial compounds. Plant amphipathic cations, such as berberine, have been shown to be good MDR substrates. Recent research has shown that in addition to berberine, Berberis species produce 5 -methoxyhydnocarpin-D, Fig. 10, an MDR inhibitor that enhances the action of this compound. In addition, isoflavones isolated Ifom Lupinus argenteus were found to enhance the antibacterial activity of a-linolenic acid, also found in the same plant [99]. 

Figure 10. The structure of 5 -methoxyhydnocarpin-D, an MDR inhibitor isolated from Berberis species that enhances the antibacterial activity of berberine.

A new method of bioactivity-directed fractionation, based on multidrug resistant pump (MDR) inhibition in Staphylococcus aureus, was reported for medicinal plants. This work resulted in the isolation, from berberine-containing Berberis species, two compounds that are themselves devoid of antibacterial activity, but that form potent synergistic couples with a sub-inhibitory concentration of berberine. The bacterial MDR pump inhibitors were identified as the flavonolignan 2 and the porphyrin 3 [98]. The isoflavones not only enhanced the antibacterial activity of the natural product, berberine. Fig. 4, but also the activity of synthetic... 

A review of the genus Berberis lists the alkaloids obtained and includes discussion of the chemistry of some recently isolated alkaloids and the pharmacology of berbamine and the crude extracts of Berberis species.The chemistry, biochemistry, and pharmacology of curare have also been reviewed. Other alkaloids whose pharmacology has been discussed are AN -dimethylberbamine and related alkaloids,trilobine and isotrilobine, and isotetrandrine and tetrandrine. The conformation and reactivity of the last alkaloid has been discussed in the light of an X-ray study. A method for quantitative extraction of tubocurarine from biological materials has been described. ... 

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). 

Calafatine (190), the parent alkaloid of this small subgroup, has only been isolated from two Berberis species, B. buxifolia and fi. horrida (Berberidaceae). The two N-oxides of calafatine, 2 a (226) and 2 P (227), have only been isolated from Berberis buxifolia (Berberidaceae). 

Umbellatine is included here because of its occurrence in Berberis species, but a correct structural formula cannot yet be written for it. 

Isotetrandrine C3 B42N205 622.76 182-183 +150.7 Berberis species, Cyclea barbala, Mahonia species, Stephania species 477-57-6... 

Oxyacanthine U37H4oN20 608.73 212-214 +285.6 Berberis species, Mahonia species, Thalictrum lucidum 548-40-3... 

Columbamine C20H20NO 338.38 Jateorhiza palmata, Berberis species 3621-36-1... 

H. Hinz and M.H. Zenk, Production of protoberberine alkaloids by cell suspension cultures of Berberis species, Nat.Wiss. 67 (1981), 620. 

Berberine (71) is produced by several plant cell cultures (Ellis, 1988). Suspension cultures of Coptis japonica produce large quantities (8% by dry weight) of berberine. Some cultures excrete berberine directly into the culture medium whereupon it crystallizes (Ellis, 1988). Cell cultures of some Berberis species synthesize jatrorrhizine (69) and colum-bamine (70) as the principal alkaloids, especially during the exponential growth phase and stationary phase (Verpoorte et al., 1991). Many of these same cultures produce berberine as the major alkaloid during lag-phase growth. 

Source Berberis vulgaris L., Mahonia aquifolium Nutt. (syn. B. aquifolium Pursh), or other Berberis species (Family Berberidaceae). 

Gurova TF, Popov YG, Fadeeva II, Shain SS, Tokachev O (1980) Callus formation and accumulation of alkaloids in the tissue culture of Stephania glabra. Rastit Resur 16 412-425 Hinz H, Zenk MH (1981) Production of protoberberine alkaloids by cell suspension cultures of Berberis species. Naturwissenschaften 67 620... 

Another notable example of the production of alkaloids in a cell-suspension culture was with Berberis species ( Berberis stolonifera) where the yield of berberine alkaloids (eg. jatrorrhizine (62) ) was as high as 10% of the dry weight of the cells °. Cell cultures of Peganum harmaZa produce harman alkaloids in minute amounts. ... 

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