Adina cordifolia

By comparison, a series of mostly monoacylated flavonols is known to date and recent reports increased the number slightly. Four new products came from Pseudognaphalium robustum and Tanacetum microphyllum (both Asteraceae), and from Adina cordifolia (Rubia-ceae). A diacetylated compound (3,5-diacetyltambulin) was recently isolated from the bark of Zanthoxylum integrifoliolum (Rutaceae). Since most of the flavonols are monoacylated, the accumulation of quercetin tetraacetate in Adina cordifolia is a remarkable result. Altogether, the newly reported compounds occur scattered in the plant kingdom their occurrence is so far of little chemosystematic value. Aerial parts of Tanacetum microphyllum (Asteraceae) yielded a derivative, which is structurally not an ester. It is, indeed, a carbo-methoxy derivative of 6-hydroxyluteolin-4 -methyl ether (compound 34 in Table 12.5). No other flavonoid of this type is known so far. 

OH (Quercetin) 3,5,7,4 -tetra- Adina cordifolia Naucleac. Heartwood 110... 

Rao, M.S., Duddeck, H., and Dembinski, R., Isolation and structural elucidation of 3,4, 5, 7-tetraacetyl quercetin from Adina cordifolia (Karam ki Gaach), Fitoterapia, 13, 353, 2002. 

As far as biosynthesis is concerned, it is clear that lyaloside (23) and pauridianthoside (26) readily derive from strictosidine (17). These three molecules display identical stereochemistry at the three chiral centers, namely, a,a,(3 for the hydrogen atoms at the 15, 20, 21 positions, respectively. They are closely related to a number of glucoalkaloids identified in Pertusadina euryncha (= Adina rubescens), e.g., rubenine (31) and desoxycordifoline (34, R = H) (49), and in Adina cordifolia, e.g., cordifoline (34, R = OH) (50). Palinine (35),... 

Adina cordifolia Hook. f. (valid name Rubiaceae Cadambine (94)... 

Glycosidic indole alkaloids have also been isolated cadambine from the bark of Adina cordifolia Hook. f. (94) and 3a-dihydrocadambine from leaves of Anthocephalus chinensis (Lamk.) A. Rich ex Walp. (95). The /3-carboline alkaloid harman is found in the leaves of both Mitragyna hirsuta (64) and Uncaria canescens Korth. (96). 

The heartwood of the southeast Asiatic tree, Adina cordifolia, contains, in addition to umbelliferone and -sitosterol, a highly oxygenated, bright yellow alkaloid, adifoline, C22H20N2O8, which gives intensely green fluorescent solutions in ethanol (37). This base appears to be identical with adinin, the yellow constituent of the same species, which was isolated earlier, and reputed to have the molecular formula C16H14O7 (38). 

Adina cordifolia has yielded a pair of jS-carboline acids, cordifoline" " (43) and adifoline (44), which are closely related to the vincosides in structural type. In both compounds the carboxy-group of precursor tryptophan is retained very few monoterpene indole alkaloids have been obtained which do still retain this feature, though of course, classical methods of alkaloid isolation would automatically lose such compounds in discarded acidic fractions. 

The full paper on the base XXXVII from Dracontomelum mangiferum has appeared (75). From Adina cordifolia the interesting alkaloid cordifoline (CXXIX, Ca9H3oN20i2) has been isolated (76). 

Rewarding sources of monoterpene alkaloid glycosides have been the Asiatic tree Adina rubescens Hemsl. and related Rubiaceous plants A. cordifolia (Roxb.) Hook. f. ex Brandis (1, 2), Nauclea latifolia Sm. (3), N. diderrichii Merrill (4), and Anthocephalus cadamba Miq. (5). The heart-wood and bark of the first has yielded so far no less than nine glycoalkaloids... 

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