Quassinoid shinjulactone

Likewise, quassinoid shinjulactone A (232) had a good EC50 value of ca. 5 pM but was cytotoxic at this concentration. Shinjulactone B (19) and ailantinol A (43) showed no cytotoxicity and were marginally active with EC50 values of 28 and 30 pM, respectively. 

Examination of the bitter principles of Simaroubaceous plants, in particular Ailanthus altissima Swingle led to the discovery in 1983 of an intriguing quassinoid, Shinjulactone C (341), possessing a modified picrasane skeleton [139]. 

The total synthesis of the quassinoid shinjulactone C (341) is detailed above, which proceeds via pentacyclic lactone [140] and... 

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],... 

The eight new quassinoids C19 type shinjulactone B (19) with a presence of a l,2-seco-l-nor-(5->10)-a >eo-picrasan-2,5-olide skeleton have been isolated from Simaroubaceae species. 

Eighteen quassinoid glycosides and nine known quassinoids were tested for inhibitoiy activity against HIV replication in H9 lymphocytic cells, as shown in Table 14. Of the compoimds tested, shinjulactone-C (123) demonstrated the highest anti-HIV activity (EC5o=10.6 p,M) in the absence of cytotoxicity with a therapeutic index of >25 [37]. 

In vitro evaluation of anti-tuberculosis activity was conducted for fifty-six quassinoids isolated in our laboratory from the Simaroubaceous plants A. altissima (10 compounds), B. antidysenterica (16 compounds), P. ailanthoides (14 compounds), and B.javanica (16 compounds), as shown in Table 15. Of the compounds tested, shinjulactone-K (119)... 

Dihydroailanthone (26) has been found as a minor quassinoid in the bark of Ailanthus glandulosa (=A. altissima) (8). The same structure was assigned to shinjulactone A isolated from the Japanese A, altissima (65). 

IsHiBASHi, M., T. Murae, H. Hirota, T. Tsuyuki, T. Takahashi, A. Itai, and Y. Iitaka Shinjulactone C, a New Quassinoid with a la,12a 5a,13a-Dicyclo-9p /f-Picrasane Skeleton from Ailanthus Altissima Swingle. Tetrahedron Lett. 1205 (1982). 

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