Toddalia aculeata

In 1839, after isolation from Ch. majus, chelerythrine (2) was described by Probst as an alkaloid yielding red salts (from Greek erythros, red) [24,24]. In fact, it was a mixture with sanguinarine [26]. The pure alkaloid was isolated by Konig, who left it the original name, chelerythrine, in spite of the bright yellow colour of its salts [26], The alkaloid toddaline, isolated from Toddalia aculeata Pers. [27], was later proved to be identical with chelerythrine [28,29]. 

Recently, 6-hydroxydihydrosanguinarine (34) has been reported as a new alkaloid isolated from Dactylicapnos torulosa Hook f et Thoms. [125,126]. The compound is described as an amorphous solid of yellow colour, however, the substance e diibits major discrepancies in ipectral data with the structure given [127]. 6-Hydroxydihydrochelerythrine has allegedly been isolated from Toddalia aculeata Pers. in the form of its acetic acid ester [128], However, its H NMR data are not in agreement with those previously published for this compound [129]. Universally, 6-hydroxydihydroderivatrves (pseudobases) are unstable semiaminoacetals with basic character which cannot occur in acidic plant tissues at all and could not be isolated as natural products especially after 5% HCl has been used in the isolation procedure cf. 125,128]. 

Nitidine and garonine are known as potential anti-tumour, antileukemic, and antiviral agents [9,52,98]. Some synthetic 12-alkoxyderivatives of 2,3,8,9-tetramethoxy QBA are potent in vitro inhibitors of the growth of P388 cells [144]. Nitidine, isolated firom Kenyan Toddalia aculeata Pers. (synonym T. asiatica (L.) Lamk.) has shown antimalarial activity [145]. Nitidine and fagaronine have been foimd to inhibit HTV reverse transcriptase [146]. 

Unfortunately, many natural coumarins have been assigned trivial names, mostly botanically derived. Although these can facilitate discussion, to a considerable extent they serve to confuse, especially since many of the endings (e,g, -ol, -one) are not at all consistent with structure. Thus umbelliferone (2) is a phenol while osthol (143) is the methyl ether of osthenol (142). Structurally closely related coumarins can have markedly different names aculeatin (249) is the epoxide of toddaculin (248), both of which occur in Toddalia aculeata, while conversely almost identical trivial names can be given to structurally quite dissimilar coumarins, e. g. ferudenol (339) and ferulenol (481). Not infrequently, the same coumarin isolated by different workers from different plant sources is given two or even three trivial names and even enantiomers are known with distinct trivial names, e.g. marmesin (103) and nodakenetin (104). 

Combes, G., R. Pernet, and R. Pierre Sur I isolement, la structure et les proprietes d une nouvelle coumarine extraite de Toddalia aculeata Pers. Bull. Soc. chim. France 1961, 1609. 

Dutta P 1942 Constituents of natural coumarins of Toddalia aculeata. J Indian Chem Soc 19 425-428... 

Toddalia aculeata (Toddalia asiatica) is a trae gi owing wild in the Nilgiri mountains, and is also found in the Philippine Islands. It is known as the wild orange tree. The leaves yield 0 08 per cent, of essential oil, which, according to Brooks, has an odour of camphor and lemon-grass. Its characters are as follows —... 

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