Quassinoids from Quassia amara

Barbetti P, Grandolini G, Fardella G, Chiappini I (1993) Quassinoids from Quassia amara. Phytochemistry 32 1007-1013... 

Cachet N, Hoakwie F, Houel E, Deharo D, Bourdy G, Jullian V (2012) Picrasin K, a new quassinoid from Quassia amara L. (Simaroubaceae). Phytochem Lett 5 162-164... 

Robins RJ, Rhodes MIC (1984) High-performance liquid chromatographic methods for the analysis and purification of quassinoids from Quassia amara. J Chromatogr A 283 436-440... 

Kupchan SM, Streelman DR (1976) Quassimarin, a new antileukemic quassinoid from Quassia amara. J Org Chem 41 3481... 

Six new quassinoids were isolated from Quassia amara Wood, dihydronomeoquassin (191) [79], 1 l-a-<9-(P-D-glycopyranosyl)-16-a-O-methylneoquassin (192), 1-a-O-methylquassin (193), 12-a-hydroxy-13,18-dehydroparain (194), and 16-a-O-methylneoquassin (195), and 11-acetylparain (196) [78],... 

Several quassinoids are known to have antileukemic activity (Blasko and Cordell, 1988 Cordell, 1978 Polonsky, 1983). Only compounds with a C20 skeleton have antileukemic activity. Quassimarin (51) from Quassia amara and bruceoside A (52) from Brucea javanica and a series of other quassinoids from Brucea antidysenterica (all Simarou-baceae) (Fig. 25.12) are active in this regard. Bruceantin (53) has a high degree of antitumor activity in P-388, LE, LL and B16 tissue culture systems (Cordell, 1978). Six quassinoids from Simaba multiflora and Soulamea soulameoides were shown to be active against several mmor systems (Klocke et al., 1985). 

Quassinoids —The antileukaemic activity of some quassinoids has revived interest in this group. Three new biologically active compounds have been isolated. Quassimarin (118) occurs in Quassia amara with the inactive simalikalactone D (129) 86 Bruceoside A, from Brucea javanica, is the glucoside (120). The third... 

T riterp. azadirachtin-like tetranortritero. azadirachtin (neem teee,Azadirachta indicaA. Juss., Meliaceae, Ang. MI) Quassinoids (biosynthetically related to triterp.) including seco- and further degraded forms Quassia amara L., Sapindales, Ang. from Jamaica quassin DSII, and other metabolites Connolly 1997). 

Figure 5 Biological activities associated with quassinoids, from Simaroubaceae species, may not be linked to a common mechanism of action/ Different testing procedures have indicated insecticidal activity for quassin, anticancer activity for quassimarin (also present in Quassia amara) and antimalarial activity for simalikalactone-D/...

Quassia amara Wood is still widely used in traditional medicine and some quassinoids and quassinoid glycosides isolated from Quassia have received renewed attention due to their biological activity as potential antitumor agents [78]. 

Reverse-phase (RP)-HPLC is probably the best system for purifying triterpenoids, principally when mixtures of isomers are present [35]. Gunther and Wagner in 1996 [36] carried out the separation and quantification of active triterpenes from Centella asiatica employing an RP system with acetonitrile-water as mobile phase. Recently, Gaspar et al. [37] described the complete separation of a mixture of triterpenoid isomers from the fruit of Arbutus unedo by HPLC coupled to a mass spectrophotometer by means of a particle beam interface (HPLC-PBMS). The separation of different quassinoids from crude bark of Quassia amara was developed by Vitanyi et al. [38] using a reverse-phase HPLC-MS... 

Other constituents include two additional quassinoids, quassimarin and simalikalactone D, isolated from Q. amara, P-sitosterol and P-sitostenone 1.8% thiamine (inP. excelsa)-, and alkaloids of the P-carboline type including canthin-6-one, 5-methoxycanthin-6-one, 4-methoxy-5-hydroxycanthin-6-one, and A-methyl-1-vinyl-P-carboline (list and horhammer willaman and Schubert). Jamaican quassia is reported to contain no tannin (martestdale). 

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