Samaderine from Samadera indica

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 three quassinoids with Cis skeleton had been isolated from Simaroubaceae species, Samaderine A (5) isolated from Samadera indica [7], and laurycolactone A (6) and B (7) isolated from Eurycoma longifolia Jack [8],... 

Wani MC, Taylor HL, Wall ME, McPhail AT, Qnan KD (1977) Plant antitumour agents isolation and structure of samaderine A (X-ray analysis) and a new antileukaemic quassinoid samadeiine E from Samadera indica. J Chem Soc Chem Commun 9 295... 

Samaderine A (1) isolated from Samadera indica 111), laurycolactone A (2) and B (3) isolated from the Vietnamese Simaroubaceae Eurycoma longifolia Jack 67) are the only three Cig-quassinoids so far known. The structures of (1) and (2) were established by X-ray analysis and that of (3) by spectral evidence. 

Wani, M. C., H. L. Taylor, M. E. Wall, A. T. McPhail, and K. D. Onan Plant Antitumour Agents Isolation and Structure of Samaderine A (X-Ray Analysis) and a New Antileukaemic Quassinoid Samaderine E from Samadera indica. J. C. S. Chem. Comm. 295 (1977). 

Samaderin B, (17 ,2A,5R,5a7 ,7a3, 113, lla3, llhR,14.5 )T,7,7tf,ll,ll ,117-hexahydro-l,ll-dihydroxy-8,lltf,14-tri-methyl-277-5tf,2,5-(methanoxymetheno)naphth[l,2-<7]oxepine-4,6,10(577)-trione, and samaderin C, (lR,2S,5R,5aR, 7aS, KXS, 113, 11 3, 1 HR, 14S)-7,7a, 10, ll,ll ,117-hexahydro-l, 10,11 -trihydroxy-8, ll ,14-trimethyl-277-5 , 2,5-(metha-noxymetheno)naphth[l,2- oxepine-4,6(177,577)-dione, were isolated from the seed kernels of Samadera indica and exhibit antifeedant activity against Spodoptera litura third-instar larvae <2003AXC416>. 

Only nine quassinoids possessing the C19 basic skeleton were isolated until 1985 samaderins B (11), C (12), D (13), an 3,4-dihydrosamaderin B (14) from the stem and leaves of Samadera indica, cedronin (15) and cedronolin (16) isolated from the fruits of Simaba cedron, eurycomalactone (17) and 5,6-dehydroeurycomalactone (18) from Eurycoma longifolia Jack, and shinjulactone B (19) isolated from Ailanthus altissima Swingle [1],... 

Four quassinoids, indaquassin C (197), samaderins C (12), B (11) and A (5), isolated from the seeds and bark of Samadera indica [113], were tested for insect antifeedant against the tobaco cutworm, Spodoptera litura. Indaquassin C (197) was the most effective antifeedant. 

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