title: C14-polyacetylenol glycosides from the roots of Codonopsis pilosula.
abstract: Eight new C14-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 Δδ(RS) values and/or the empirical rule of Mo2(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 (6S,7S)-6,7-diol unit against a (6R,7R)-6,7-diol unit in the others. The absolute configurations of lobetyolinin (9) and pratialin B (10) were determined for the first time.
authors.affiliation: a State Key Laboratory of Bioactive Substance and Function of Natural Medicines , Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , China.|b Department of Pharmacy , Xiangya Hospital, Central South University , Changsha 410008 , China.
authors.forename: Yue-Ping
authors.initials: YP
authors.lastname: Jiang
authors.affiliation: a State Key Laboratory of Bioactive Substance and Function of Natural Medicines , Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , China.
authors.forename: Yu-Feng
authors.initials: YF
authors.lastname: Liu
authors.affiliation: a State Key Laboratory of Bioactive Substance and Function of Natural Medicines , Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , China.
authors.forename: Qing-Lan
authors.initials: QL
authors.lastname: Guo
authors.affiliation: a State Key Laboratory of Bioactive Substance and Function of Natural Medicines , Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , China.
authors.forename: Jian-Gong
authors.initials: JG
authors.lastname: Shi
mesh_terms: D029745:Codonopsis / Q000737:chemistry*; D005233:Fatty Alcohols / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D053279:Polyynes / Q000737:chemistry; D014312:Trisaccharides / Q000737:chemistry
chemical_list: D005233:Fatty Alcohols; D006027:Glycosides; D014312:Trisaccharides; C521561:lobetyolin; C472949:pratialin B; D053279:Polyynes
keywords: C14-polyacetylenol glycosides; Campanulaceae; Codonopsis pilosula; codonopilodiynosides H-M; codonopiloenynenosides A and B