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Isolation, X-ray crystal structure and theoretical calculations of the new compound 8-Eepicordatin and identification of others terpenes and steroids from the bark and leaves of Croton palanostigma Klotzsch

DOI: 10.1590/S0103-50532010000400021

Keywords: croton palanostigma klotzsch, terpenes, steroids, nmr dft calculations, x-ray crystallography.

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Abstract:

phytochemical studies of the bark and leaves of croton palanostigma klotzsch (euphorbiaceae) led to the isolation of a new clerodane diterpene, 8-epicordatin (2), in addition to 12-oxohardwickiic acid methyl ester (3), aparisthman, cordatin (1), ent-trachyloban-18-oic acid, ent-13-epimanoyl oxide, ent-3-oxo-13-epimanoyl oxide, ent-3β-hydroxy-13-epimanoyl oxide, sitosterol, stigmasterol, stigmastan-3-one, 6β-hydroxystigmast-4-en-3-one, 6β-hydroxystigmasta-4,22-dien-3-one, stigmast-4-en-3-one, stigmasta-4,22-dien-3-one, 3-o-acetylaleuritolic acid, 11α-hydroxyurs-12-en-3-one, α-amyrenone, 24-methylenecycloartenone and lupenone. these compounds were isolated using typical phytochemical procedures and the structures were deduced from spectroscopic studies, including 2d nmr experiments. in addition, the crystalline structure of 8-epicordatin (2) was determined by x-ray diffraction. nmr theoretical calculations at the b3pw91/dgdzvp level were used to confirm the assignment of the chemical shifts of the h-7α and h-7β hydrogens of 8-epicordatin.

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