21beta-Hydroxy-oleanane-type triterpenes from Hippocratea excelsa |
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Authors: | Cáceres-Castillo David Mena-Rejón Gonzalo J Cedillo-Rivera Roberto Quijano Leovigildo |
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Affiliation: | Laboratorio de Química Orgánica de Investigación, Facultad de Química, Universidad Autónoma de Yucatán, Calle 41 No. 421, Col. Industrial, C.P. 97150 Mérida, Yucatán, México. |
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Abstract: | Stem bark of Hippocratea excelsa afforded six pentacyclic triterpenes, five oleanane and one ursane types. They were identified as 11beta,21beta-dihydroxy-olean-12-ene-3-one (2), 3alpha,11alpha,21beta-trihydroxy-olean-12-ene (3), 3alpha,21beta-dihydroxy-11alpha-methoxy-olean-12-ene (4), 3alpha,21beta-dihydroxy-olean-9(11),12-diene (5), 3alpha,21beta-dihydroxy-olean-12-ene (6) and 3alpha,21beta-dihydroxy-11alpha-methoxy-urs-12-ene, isolated as its diacetate derivative (7), as well as 3alpha,21beta-dihydroxy-olean-12-ene (1) previously isolated from the root bark. The known alpha- and beta-amyrin, oleanoic and ursolic acids, trans-polyisoprene, and the ubiquitous beta-sitosterol were also isolated. Structures were elucidated on the basis of spectroscopic analyses, including homo- and heteronuclear correlation NMR experiments (COSY, ROESY, HSQC and HMBC) and comparison with literature data. The antigiardial activity of compounds 2-5 was not significant. |
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Keywords: | Hippocratea excelsa Celastraceae Oleanane triterpenes Giardia intestinalis |
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