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[PMID]: | 27726359 |
[Au] Autor: | Pardo-Novoa JC; Arreaga-González HM; Gómez-Hurtado MA; Rodríguez-García G; Cerda-García-Rojas CM; Joseph-Nathan P; Del Río RE |
[Ad] Endereço: | Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Ciudad Universitaria , Morelia, Michoacán 58030, Mexico. |
[Ti] Título: | Absolute Configuration of Menthene Derivatives by Vibrational Circular Dichroism. |
[So] Source: | J Nat Prod;79(10):2570-2579, 2016 Oct 28. | [Is] ISSN: | 1520-6025 |
[Cp] País de publicação: | United States |
[La] Idioma: | eng |
[Ab] Resumo: | The aerial parts of Ageratina glabrata afforded (-)-(3S,4R,5R,6S)-3,5,6-trihydroxy-1-menthene 3-O-ß-d-glucopyranoside (1) and (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 3-O-ß-d-glucopyranoside (3). Acid hydrolysis of 1 yielded (+)-(1R,4S,5R,6R)-1,5,6-trihydroxy-2-menthene (5) and (+)-(1S,4S,5R,6R)-1,5,6-trihydroxy-2-menthene (6), while hydrolysis of 3 yielded (+)-(3S,4S,6R)-3,6-dihydroxy-1-menthene (10), (+)-(1R,4S,6R)-1,6-dihydroxy-2-menthene (11), and (+)-(1S,4S,6R)-1,6-dihydroxy-2-menthene (12). The structures of the new compounds 1, 2, 5-9, and 11 were defined by 1D and 2D NMR experiments, while the absolute configurations of the series of compounds were determined by comparison of the experimental vibrational circular dichroism (VCD) spectra of the 1,6-acetonide 5-acetate derived from 6 and of the 1,6-acetonide derived from 12 with their DFT-calculated spectra. In addition, Flack and Hooft X-ray parameters of 10 permitted the same conclusion. The results further led to the absolute configuration reassignment of 10 isolated from Brickellia rosmarinifolia, Mikania saltensis, Ligularia muliensis, L. sagitta, and Lindera strychnifolia, as well as of 11 from Cacalia tangutica, as ent-11. |
[Mh] Termos MeSH primário: |
Ageratina/química Dicroísmo Circular/métodos Terpenos/química
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[Mh] Termos MeSH secundário: |
Asteraceae México Estrutura Molecular Ressonância Magnética Nuclear Biomolecular Estereoisomerismo
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[Pt] Tipo de publicação: | JOURNAL ARTICLE |
[Nm] Nome de substância:
| 0 (Terpenes); 11028-39-0 (1-menthene) |
[Em] Mês de entrada: | 1706 |
[Cu] Atualização por classe: | 170616 |
[Lr] Data última revisão:
| 170616 |
[Sb] Subgrupo de revista: | IM |
[Da] Data de entrada para processamento: | 161012 |
[St] Status: | MEDLINE |
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