Simaba multiflora

Simaroubaceae 15 a. Brucea javanica (57-59) 15b. Castela texana 60) 15c. Hannoa klaineana 61) 15d. Simaba multiflora 56, 62) 15e. Soulamea soulameoides (56)... 

Arisawa M, Handa SS, McPherson DD, Lankin DC, Cordell GA, Fong HHS, Farnsworth NR (1984) Plant Anticancer Agents. XXIX. Cleomiscosin A from Simaba multiflora, Soulamea soulameoides and Matayba arborescens. J Nat Prod 47 300... 

Arisawa M, Kinghom AD, Cordell GA, Farnsworth NR (1983) Plant Anticancer Agents. XXIV. Alkaloid Constituents of Simaba multiflora. J Nat Prod 46 222... 

Quassinoids.—The structure of soulameolide (108), a new C25 quassinoid from Soulamea tomentosa, has been established by X-ray analysis.The search for biologically active compounds continues. Undulatone (109) from Hannoa undulata, 6a-tigloyloxychapparinone (110) from Ailanthus integrifoliaj and 6a-senecioylchapparinone (111) from Simaba multiflora have antileukaemic... 

Hydroxycanthin-6-one (18) has been isolated from the root bark of Ailanthus excelsa (25), the trunk (37) and stem bark (38) of Odyendea gabonensis, the stem bark of Pierreodendron kerstingii (39), and the wood of Simaba multiflora (40). The bathochromic shift caused by alkali addition shown in the UV spectrum together with MS data suggested that... 

Methoxycanthin-6-one (19) has been isolated from the bark of Simaba cuspidata (2) and the stem bark of Simaba multiflora (41). From IR, UV, high-resolution MS (M at mlz 250.0735), and H-NMR (8 3.99, 3H, s), it was supported that 19 was a methoxycanthin-6-one. From the fact that there are two isolated pairs of vicinal protons (H-1 and H-2 H-4 and H-5) in the H-NMR spectrum, it is obvious that the methoxyl group does not exist in ring C or D. In addition, the lower field proton H-8 (8 8.13, H, d, J = 2 Hz) in ring A does not show ortho coupling. These findings led to determination of structure 19. 

Two new quassinoids, 13,18-dehydro-6a-senecioy1oxychaparrin (200) and 12-dehydro-6a-senecioyloxychaparrin (201), have been isolated from the fruits of Simaba multiflora [81],... 

A series of six quassinoids isolated from Simaba multiflora and Soulamea soulameoides were shown to be active as growth inhibitors and as antifeedants against Heliothis virescens (cotton budworm) and Spodoptera frugiperda (fall armyworm) (Klocke et al., 1985). 

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). 

Arisawa M, Handa S S, McPherson D D, Lankin D C, Cordell G A, Fong H H S, Farnsworth N R 1984 Cleosmine A from Simaba multiflora, Soulamea soulameoides, and Matayba arbores-cens. J Nat Prod 47 300-307... 

Arisawa M, Fujita A, Morita N, Kinghorn AD et al. 1985 Plant anticancer agents XXXV. Further constituents of Simaba multiflora (Simaroubaceae). Planta Med 49 348-349... 

Arisawa, M., a. D. Kinghorn, G. A. Cordell, and N. R. Farnsworth Plant Anticancer Agents. XXIIL 6a-Senecioyloxy Chaparrin, a New Antileukemic Quassinoid from Simaba multiflora. J. Nat. Prod. 46, 218 (1983). 

Polonsky, J., J. Gallas, J. Varenne, T. Prange, C. Pascard, H. Jacquemin, and C. Moretti Isolation and Structure (X-Ray Analysis) of Karinolide, A New Quassinoid from Simaba multiflora. Tetrahedron Lett. 869 (1982). 

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