title: C₁₄-polyacetylene glucosides from Codonopsis pilosula.
abstract: Seven new C14-polyacetylene glucosides codonopilodiynosides A-G (1-7) were isolated from an aqueous extract of the Codonopsis pilosula roots. Their structures were determined by spectroscopic and chemical methods as (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranoside (1), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (2), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5,14-di-O-β-D-glucopyranoside (3), (-)-(5S,6E)-tetradeca-6-en-8,10-diyn-1,5,14-triol 5-O-β-D-glucopyranoside (4), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5-diol 5-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (5), (-)-(6S,4E,12E)-tetradeca-4,12-dien-8,10-diyn-1,6-diol 6-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (6), and (-)-(5S,6E)-tetradeca-6-en-1,5-epoxy-8,10-diyn-14-ol 14-O-β-D-glucopyranosyl-(1″ → 2')-β-D-glucopyranoside (7), respectively. The absolute configurations of 1-7 were assigned by enzymatic hydrolysis followed by isolation of glucose and aglycones (1a and 4a-7a), and subsequent comparison of specific rotation, TLC, and (1)H NMR data of the glucose with an authentic sugar sample and application of modified Mosher's method based on the MPA determination rule of Δδ(RS) values for 1a and 4a, and Δδ(S) values for 6a. The configuration of 7 was assigned by electronic circular dichroism calculations based on the quantum-mechanical time-dependent density functional theory.
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: Yue-Ping
authors.initials: YP
authors.lastname: Jiang
authors.forename: Yu-Feng
authors.initials: YF
authors.lastname: Liu
authors.forename: Qing-Lan
authors.initials: QL
authors.lastname: Guo
authors.forename: Zhi-Bo
authors.initials: ZB
authors.lastname: Jiang
authors.forename: Cheng-Bo
authors.initials: CB
authors.lastname: Xu
authors.forename: Cheng-Gen
authors.initials: CG
authors.lastname: Zhu
authors.forename: Yong-Chun
authors.initials: YC
authors.lastname: Yang
authors.forename: Sheng
authors.initials: S
authors.lastname: Lin
authors.forename: Jian-Gong
authors.initials: JG
authors.lastname: Shi
mesh_terms: D029745:Codonopsis / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D053279:Polyynes / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
chemical_list: D005960:Glucosides; D053279:Polyynes
keywords: C14-polyacetylene glucosides; Campanulaceae; Codonopsis pilosula; absolute configuration; codonopilodiynosides A–G