Stereochemical assignments of rubiaquinones A-C, naphthoquinone derivatives from &ITRubia yunnanensis&IT
Suyama, Yoshihiro1; Higashino, Yusuke1; Tanaka, Naonobu1; Tatano, Yutaka1; Yagi, Hideki1; Kawazoe, Kazuyoshi1; Murakami, Kotaro1; Li, Shun-Lin1; Sun, Han-Dong1; Kashiwada, Yoshiki1
AbstractThree 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.
KeywordNaphthoquinone Derivative Rubiaquinones A-c Stereochemical Assignment Composite Ecd Spectrum Rubia Yunnanensis
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Affiliation1.[Suyama, Yoshihiro
2.Higashino, Yusuke
3.Tanaka, Naonobu
4.Kashiwada, Yoshiki] Tokushima Univ, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
5.[Tanaka, Naonobu] Tokushima Univ, Grad Sch Biosci & Bioind, Tokushima 7708513, Japan
6.[Tatano, Yutaka
7.Yagi, Hideki] Int Univ Hlth & Welf, Fac Pharmaceut Sci, Ohtawara 3248501, Japan
8.[Kawazoe, Kazuyoshi] Showa Univ, Sch Pharm, Shinagawa 1428555, Japan
9.[Murakami, Kotaro] Sojo Univ, Fac Pharmaceut Sci, Kumamoto 8620082, Japan
10.[Li, Shun-Lin
11.Sun, Han-Dong] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Chi, Kunming 650201, Yunnan, Peoples R China
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Suyama, Yoshihiro,Higashino, Yusuke,Tanaka, Naonobu,et al. Stereochemical assignments of rubiaquinones A-C, naphthoquinone derivatives from &ITRubia yunnanensis&IT[J]. TETRAHEDRON LETTERS,2017,58(48):4568-4571.
APA Suyama, Yoshihiro.,Higashino, Yusuke.,Tanaka, Naonobu.,Tatano, Yutaka.,Yagi, Hideki.,...&Kashiwada, Yoshiki.(2017).Stereochemical assignments of rubiaquinones A-C, naphthoquinone derivatives from &ITRubia yunnanensis&IT.TETRAHEDRON LETTERS,58(48),4568-4571.
MLA Suyama, Yoshihiro,et al."Stereochemical assignments of rubiaquinones A-C, naphthoquinone derivatives from &ITRubia yunnanensis&IT".TETRAHEDRON LETTERS 58.48(2017):4568-4571.
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