C14-polyacetylenol glycosides from the roots of Codonopsis pilosula
2015
Jiang, Yue-Ping | Liu, Yufeng | Guo, Qing-Lan | Shi, Jian-Gong
Eight new C ₁₄-polyacetylenol glycosides, containing ene-diyne and ene-yn-ene chromophores named codonopilodiynosides H-M (1 – 6) and codonopiloenynenosides A and B (7 and 8), respectively, together with three known analogs lobetyolinin, pratialin B, and lobetyolin (9 – 11), were isolated from an aqueous extract of the roots of Codonopsis pilosula . Their structures were determined by spectroscopic and chemical methods including 2D NMR data analysis and enzymatic hydrolysis. The absolute configurations of aglycones in 1 – 10 were assigned by application of the methoxyphenylacetic acid (MPA) determination rule of Δ δ ᴿS values and/or the empirical rule of Mo ₂(OAc) ₄-induced circular dichroism for the vicinal diols, or by comparison of specific rotation values with those of reported compounds. Compounds 4 – 6 are the first polyacetylenol glycosides possessing a cis -ene-diyne chromophore from the genus Codonopsis , while 8 has a rear trans -ene-yn- cis -ene chromophore and a (6 S ,7 S)-6,7-diol unit against a (6 R ,7 R)-6,7-diol unit in the others. The absolute configurations of lobetyolinin (9) and pratialin B (10) were determined for the first time.
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