Synthesis and Anti-HIV Activity of Lupane and Olean-18-ene Derivatives. Absolute Configuration of 19,20-Epoxylupanes by VCD

Fátima Gutiérrez-Nicolás†‡, Bárbara Gordillo-Román§, Juan C. Oberti†, Ana Estévez-Braun*†‡, Ángel G. Ravelo*†‡, and Pedro Joseph-Nathan§
† Instituto Universitario de Bio-Orgánica “Antonio González”, Departamento de Química Orgánica, Universidad de La Laguna, La Laguna 38206 Tenerife, Spain
‡ Instituto Canario de Investigación del Cáncer (ICIC), Canary Islands, Spain
§ Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D. F., 07000 México
Facultad de Ciencias Químicas, Universidad de Córdoba and IMBIV (UNC−CONICET), Avenida Haya de la Torre y M. Allende, Ciudad Universitaria, Córdoba, Argentina
J. Nat. Prod., Article ASAP
DOI: 10.1021/np200910u
Publication Date (Web): March 30, 2012

Lupane triterpenoids 2 and 512 and oleanene derivatives 13 and 14 were prepared from lupeol (1), betulin (3), and germanicol (4). They were tested for anti-HIV activity, and some structure–activity relationships were outlined. The 20-(S) absolute configuration of epoxylupenone (8) was assessed by comparison of the observed and DFT-calculated vibrational circular dichroism spectra. The CompareVOA algorithm was employed to support the C-20 configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures.

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