The title compound, a natural b,d-seco-limonoid, C(27)H(34)O(8)·H(2)O, and known as Swietenolide monohydrate, has been isolated from S. macrophylla King. In the molecular structure, the four fused six-membered rings adopt twist-boat (ring A), approximate chair (ring B), envelope (ring C) and half-chair (ring D) conformations. The attached furan ring is essentially planar. O-H⋯O hydrogen bonds a...

Phytochemical analysis of A. balsamea oleoresin led to the isolation of three new 3,4-seco-lanostane triterpenoids 1-3, one new cycloartane triterpenoid 4 along with fourteen known terpenoids. Structure determinations were based on extensive 1D/2D NMR, IR and MS spectroscopic analyses, and comparison with literature data. The isolated compounds were evaluated in vitro for their cytotoxicity aga...

A new and efficient strategy is described for carrying out the enantiospecific synthesis of monocarbocyclic terpenoids from (-)-sclareol (1). The key steps are the Grob scission of l l p toluenesulphonyloxydriman-7ct-ol (2) to give the tobacco seco-sesquiterpene 3 and the Baeyer-Villiger oxidation of 4-[(1'S, 2'S)-2'-formyl-2',6',6'-trimethylcyclohexyl]-2-butanone (4), derived from 3. The first...

Gardenia plants have long been used as traditional medicines in various countries including Thailand. In this study, two new 3,4-seco-cycloartane triterpenes, sootependial (1) and sootepenoic acid (2), were isolated from bud exudate of G. sootepensis, together with five known compounds. Their structures were elucidated on the basis of spectroscopic data. Sootependial (1) showed potent cytotoxic...

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Alejandro Ayala, Gabriella Piccinelli, Angel Sánchez and Maria Elena Tejeda-Yeomans Instituto de Ciencias Nucleares, Universidad Nacional Autónoma de México, Apartado Postal 70-543, México Distrito Federal 04510, Mexico. Centro Tecnológico, FES Aragón, Universidad Nacional Autónoma de México, Avenida Rancho Seco S/N, Bosques de Aragón, Nezahualcóyotl, Estado de México 57130, Mexico. Instituto d...

In efforts directed toward the synthesis of seco-prezizaane sesquiterpenoids, a stereoselective annulation reaction has been developed between 4-hydroxy-1,6-enynes and TMS-alkynes that delivers cross-conjugated triene-containing hydroindanes. Contrary to previous reports, enyne substrates bearing two propargylic ethers enable the presumed organometallic intermediate to be trapped by double elim...

In this study, a computerized method for detection of pulmonary embolism in spiral CT angiography was developed. The method is based on segmentation of pulmonary vessels to limit the search space for thrombi. Several three-dimensional image features such as local contrast, seco nd derivatives, and distance to the vessel wall were employed for detection of thrombi and for elimination of false po...

Anaerobic incubation of phorbol (1) from Croton tiglium with human intestinal bacteria afforded five metabolites: isophorbol (2), deoxyphorbol (3), 4beta,9alpha,20-trihydroxy-13,15-seco-1,6,15-tigliatriene-3,13-dione (4), 4beta,9alpha,20-trihydroxy-15,16,17-trinor-1,6-tigliadiene-3,13-dione (5) and 4beta,9a,20-trihydroxy-14(13-->12)-abeo-12alphaH-1,6-tigliadiene-3,13-dione (6). All these metabo...

The phytochemical investigation of a methanolic leaf extract of Aglaia rubiginosa furnished 15 isoprenoid constituents, eight of which represented new natural entities. Two androstane derivatives (1 and 2), previously synthesized, and also obtained by microbiological transformations; an extraordinary 17-octanor-cycloartane-ring-A-seco acid (3); four cycloartane-type triterpenes (4-7); and three...