| Absolute Configuration and Conformational Analysis of Brevipolides, Bioactive 5,6-Dihydro-α-pyrones from Hyptis brevipes. | |
| | |
MedLine Citation:
|
PMID: 23282042 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
|
The (6'S)-configuration of brevipolides A-J (1-10), isolated from Hyptis brevipes, was established by X-ray diffraction analysis of 9 in conjunction with Mosher's ester analysis of the tetrahydro derivative 11 obtained from both geometric isomers 8 and 9 as well as by chemical correlations. The structure of the new brevipolide J (10) was characterized through NMR and MS data as having the same 6-heptyl-5,6-dihydro-2H-pyran-2-one framework possessing the cyclopropane moiety of all brevipolides but substituted by an isoferuloyl group instead of the p-methoxycinnamoyl moiety found in 8 and 9. Conformational analysis of these cytotoxic 6-heptyl-5,6-dihydro-α-pyrones was carried out on compound 9 by application of a protocol based on comparison between experimental and DFT-calculated vicinal (1)H-(1)H NMR coupling constants. Molecular modeling was used to correlate minimum energy conformers and observed electronic circular dichroism transitions for the isomeric series of brevipolides. Compounds 7-10 exhibited moderate activity (ED(50) 0.3-8.0 μg/mL) against a variety of tumor cell lines. |
| | |
Authors:
|
G Alejandra Suárez-Ortiz; Carlos M Cerda-García-Rojas; Adriana Hernández-Rojas; Rogelio Pereda-Miranda |
Publication Detail:
|
Type: JOURNAL ARTICLE Date: 2013-1-2 |
Journal Detail:
|
Title: Journal of natural products Volume: - ISSN: 1520-6025 ISO Abbreviation: J. Nat. Prod. Publication Date: 2013 Jan |
Date Detail:
|
Created Date: 2013-1-3 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 7906882 Medline TA: J Nat Prod Country: - |
Other Details:
|
Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
|
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México , Circuito Exterior Ciudad Universitaria, México City, D. F. 04510 México. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Distinct neuroendocrine mechanisms control neural activity underlying sex differences in sexual moti...
Next Document: The shaping and integration of a trauma therapist.