期刊
TETRAHEDRON LETTERS
卷 58, 期 48, 页码 4568-4571出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.10.051
关键词
Naphthoquinone derivative; Rubiaquinones A-C; Stereochemical assignment; Composite ECD spectrum; Rubia yunnanensis
资金
- JSPS KAKENHI [JP18406028, JP17K08337]
- Grants-in-Aid for Scientific Research [17K10028, 17K08337, 15K19181] Funding Source: KAKEN
Three new naphthoquinone derivatives, rubiaquinones A-C (1-3), were isolated from the roots of Rubia yunnanensis. Rubiaquinone A (1) was a racemic naphthoquinone dimer consisting of a 1,4-dihydroxy-naphthalene and a 4-hydroxy-1,2-naphthoquinone moieties with a 2-oxo-propyl group. Rubiaquinones B (2) and C (3) were structurally unique trimeric naphthoquinones with a racemic nature possessing one chiral axis and one chiral carbon in common. The planar structures of 1-3 were assigned by detailed spectroscopic analyses, and enantiomers of 1-3 were obtained by optical resolutions. The absolute configurations of (+)-1 and (-)-1 were elucidated by interpretation of the ECD spectra with the aid of TDDFT ECD calculation, while those of enantiomers obtained from 2 and 3 were assigned by analyses of the composite ECD spectra generated by summing appropriate ECD spectra of enantiomers. Rubiaquinone A (1) exhibited antimicrobial activity against Bacillus subtilis. (C) 2017 Elsevier Ltd. All rights reserved.
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