Simarouba amara

Hydroxycanthin-6-one (16) has been isolated from the root bark of Simarouba amara (34) and from cell cultures of A. altissima 12,15). Since its UV spectrum was similar to that of 5-methoxycanthin-6-one (25), Lassak et al. (34) assumed it to be 4- or 5-hydroxycanthin-6-one. The prominent peak at M -56 (mlz 180, M -2CO) in the mass spectrum supported structure 16 having an OH adjacent to the carbonyl group. The final confirmation of structure 16 was made through direct comparison of methylated 16 with authentic 7. 

Quassinoids.—2 -AcetylgIaucarubine (98) and a new antineoplastic quassinoid, 13,18-dehydroglaucarubinone (99), have been isolated from Simarouba amara. The related 13,18-dehydroglaucarubol-15-isovalerate (100) has been reported from Ailanthus excelsa. The details of the crystal structural analyses of samaderin 7A (101), from Samadera indica, and 6-hydroxypicrasin B (102), from Soulamea species, have appeared. 

Until 1985, only six quassinoids possessing the C25 basic skeleton were known simarolide (209) from the bark of Simarouba amara, picrasin A (210) isolated from Picrasma quassioides, soulameolide (211) from Soulamea tomentosa, simarinolide (212) and guanepolide (213) from the root bark of the Simaba cf. orinocencis, and deacetylsimarolide (214) isolated from the fruits of Simaba moretii [1]. 

This compound is still in use. Traditional uses of other plant products led to the identification of other compounds with activity against Entamoeba in the 1940s and 1950s, including the steroidal alkaloid conessine from Holarrhena sp. (Apocyanaceae), glaucarubin from Simarouba amara (Simaroubaceae), and henna from Lawsonia alba (Lythraceae) [163]. 

Under the name of quassia or quassia wood Quassiae lignum), two indiscriminate species were then sold in Europe Quassia amara (mainly root, wood and stems) and Picrasma excelsa (Sw.) Planch, (formerly Picraena excelsa (Sw.) Lindley) or Jamaican quassia (trunk wood) [17,18, 20]. Quassia wood was initially used as an antiseptic, for meat preservation and as antipyretic. But because of its bitter principles its main recommendation was as a digestive and tonic [17, 21]. Q. amara was rapidly registered in various European pharmacopoeias, alone or with other Simaroubaceae species with the same reputation, such as Picrasma excelsa or Simarouba amara Aubl. [22-25]. The reputation of quassia wood then spread to the United States, where the medicinal use of cups mostly made of Q. amara wood became popular [26]. Meanwhile, a few Simaroubaceae were registered in North American official pharmaceutical documents, such as the King s American Dispensatory [27] or the United States Dispensatory [28]. 

Moreover, some species have been introduced, naturalized, cultivated, and marketed outside their original distribution area with respect to their therapeutic value. This is the case for Simarouba amara, introduced in India Ailanthus altissima, introduced as an ornamental and medicinal plant in North America, then in Europe Brucea javanica, now cultivated in Africa and Quassia amara, a few specimens of which were introduced in Africa and India. In their country of... 

Ailanthus altissima, Brucea antidysenterica, Picrasma excelsa. Quassia africana. Quassia undulata, Simaba cedron, and Simarouba amara are also used as anthelmintics. 

Lastly, three Simaroubaceae species are described as antivenom Brucea antidysenterica. Quassia amara, and Simaba cedron, with a veiy strong convergence of use for the cotyledons of Simaba cedron seeds in South America). Brucea antidysenterica, Brucea javanica, Eurycoma longifolia. Quassia undulata, and Picrasma javanica are known as antidotes to food poisoning or other types poisoning. Central nervous system troubles, such as dementia, nervousness, and epilepsy, and alcohol addiction are treated with preparations of Ailanthus altissima. Quassia undulata, Simarouba amara, or Picrasma excelsa. 

O Neill MJ, Bray DH, Boardman P, Wright CW, Phillipson JD, Warhurst DC, Gupta MP, Correya M, Solis C (1988) Plants as sources of antimalarial drugs. Part 6. Activities of Simarouba amara fruits. J Ethnopharmacol 22 183... 

Ailanthus altissima is a tall deciduous tree of Chinese origin. A study of the wood extractives has revealed the presence of three alkaloids canthin-6-one, can-thin-6-one-3-oxide, and l-methoxycanthin-6-one (118). Another member of the same family, Simarouba amara, contains 5-hydroxycanthine-6-one (93). The root bark of Ailanthus excelsa contains four canthine derivatives canthin-6-one, 1 -methoxycanthin-6-one, 5-methoxycanthin-6-one, and 8-hydroxanthin-6-one (27). 

Lassak E V, Polonsky J, Jacquemin 1977 5-Hydroxycanthin-6-one from Simarouba amara. Phytochemistry 16 1126-1127... 

Gris (58). 13,18-Dehydroglaucarubinone (36b) was found in Simarouba amara (91) and in Ailanthus altissima (36), 13,18-dehydroailanthinone (37b) in Pierrodendron kerstingii (46) and 13,18-dehydroexcelsin (38) was found in Ailanthus excelsa (40) and in A.malabarica (39). Only those quassinoids which possess an a, 3-unsaturated ketol group in ring A display significant antineoplastic activity in the NIH murine lymphocytic leukemia P 388 (PS) system. 

Acetoxyglaucarubine (32b) Excelsin (33) C27H38O11 C25H36O9 538 480 Simarouba amara Ailanthus excelsa Odyendyea gabonensis 246° + 29.5° (91, 112) (40, 112)... 

Polonsky, J., Z. Varon, H. Jacquemin, and G. R. Pettit The Isolation and Structure of 13,18-Dehydroglaucarubinone, a new antineoplastic quassinoid from Simarouba amara. Experientia 34, 1122 (1978). 

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