Bisbenzylisoquinoline Alkaloids--A Review

Abstract

4legre, RS, Brasil .$BSTR.xT.-The review presents a glossary of the bisbenzylisoquinoline a k aloids. The following information is tahulated: structural formulas of all the bisbenzj-lisoquinoline alkaloids (BBI) with their molecular formulas: molecular n-eights: mp and : a ]~ values: uv, ord, nnir, mass data: degradation methods applied to determine their striictures: and sourres. -i list of the plants n-ith the particular part studied and the BBI alkaloidis) isolated from each source is furnished. In addition, this article summarizes the distribution of different t>-pes of BBI alkaloids in differenf genera, methods of isolation, and degradative techniques applied for structure elucidation.Since the days of the earliest commercial drug preparations, viz., R a d i i pareira bratae, Bebeeriiim pirrum and Curare (the arron-poison of South A%merican Indians), natural products chemists and pharmacognosists have been interested in the bisbenzylisoquinoline (BBI) alkaloid-because of their diverse formulations and varied pharniacological effects. Several reviews on the BBIs are already available (1-Sa). The article by Shamma ( 7 ) covers different chenlical aspects of thi. field and has intensified the long-felt need for a glossary of these alkaloids containing all information nece.sarj-for a natural product chemist searching for nen-BBI alkaloid-.BBI alkaloids are built up of tn-o benzylisoquinoline (BI) units linked by ether bridges. In addition to this ether linkage. methr lenosy bridging or direct carbon carbon bonding is also found between the two BI units. A variety of structural patterns arise in the BBI molecules due to differences in (1.) the number of aromatic oxygen subqtituent-present ; (2.) the number of ether linkage>; (3.) the nature of ether bridges, viz., diphen! 1 ether or benzylphenyl ether: and (4.) the sites on the tn-o BI unit-at n hich the ether or the carbon carbon bond originates. Based on these differences. the BBI alkaloids are claqsified into the groups and subgroups as shon n in table 1.Individual members in each group differ simplJ-in (1.) the nature of the osygenated substituents (OH, OMe, OCH,O) : (2.) the nature of substitution of the t n o nitrogen atonis ISH. S l l e , S -l I e r 3 S O ) ; (3.) the degree of unsaturation of the hetero ring.: and (4.) the stereochemistrj-of the tu-o asymmetric centers. BOTAA ICAL bocmE.-DiW-ibution of the different groups of BBI alkaloids in different genera and the botanical sources of these alkaloids are depicted in tables 2 and 3 respectively. Ecological factors affect the nature and amount of BBI alkaloids in plants. Cissampelos pareira Linn. from Kashmir yielded h a p t i n e (So. 1 3 i ,table 4) and hayatinine (So. 138. table 4) (both S S I type); xhereas a plant from Pilibhit yielded hayatine and curine ( S o . 133, table 4) (=.anie type), but no hayatinine (10); the plants from lladra. and Madagascar contained, in addition to hayatine and curine, isocliondodendrine ( S o . 122. table 4) (S type), which was not found in the extracts from Pilibh...

Warifteine and methylwarifteine: 1H and 13C assignments by two‐dimensional NMR spectroscopy

“…Besides the molecular ion at m/z 592 and the base peak at m/z 488, formed by the expulsion of C 8 H 8 , the p-xylyl moiety, ring C (M C ž 104), characteristic for this class of alkaloids, 6 the spectrum was identical with that of warifteine. 1 A primary goal of this study was to determine the location of the phenolic and methoxyl substituents of alkaloid 1, so that its complete structure would finally be known.…”

“…Since the relative positions of the OH and OMe groups on each aromatic ring of the two isoquinoline moieties were never defined, the structure of the most abundant alkaloid of C. ovalifolia, warifteine, remained unsettled even though the x-ray crystal structures of both dimethylwarifteine 4 and methylwarifteine 5 were determined. We remained interested in elucidating the complete structures of warifteine and methylwarifteine since publishing a review on bisbenzylisoquinoline alkaloids, 6 where warifteine and cissampareine were placed in a special section with one diphenyl ether and one benzyl phenyl ether linkage. In an extension of our work on the application of high-field NMR spectroscopy to solving structural problems in natural products chemistry, 7 we undertook the complete 1 H and 13 C assignments of warifteine and methylwarifteine by two-dimensional NMR spectroscopy as described here.…”

Characterization of 10 species ofMahonia by capillary electrophoresis

“…The dried stems of Mahonia bealei and Mahonia fortuner are commonly used against fever, swelling, inflammation, janundice, dysentery and constipation in Chinese traditional medicine [2]. The pharmaceutically relevant compounds in Mahonia are alkaloids, including berberine, berbamine, isotetrandine, oxyacanthine, palmatine, jatrorrhizhine magnoflorine and columbamine [3][4][5]. Methods such as TLC and HPLC have been used for the analysis and detection of alkoids in Mahonia [6,7].…”

Pulmonary Toxicity and Metabolic Activation of Dauricine in CD-1 Mice

“…The majority of naturally occurring BBIQ alkaloids are mainly identified from families Menispermaceae, Ranunculaceae, Annonnaceae, and Moniaceae (Guha et al, 1979;Schiff, 1983Schiff, , 1987Schiff, , 1991. Bisbenzylisoquinoline alkaloids have been reported to show a variety of pharmacological activities (Schiff, 1991).…”