Journal
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH
Volume 17, Issue 6, Pages 601-614Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10286020.2015.1041932
Keywords
Campanulaceae; Codonopsis pilosula; codonopilodiynosides A-G; C-14-polyacetylene glucosides; absolute configuration
Funding
- National Natural Sciences Foundation of China [30825044, 21132009]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT1007]
- National Science and Technology Project of China [2012ZX09301002-002, 2011ZX0 9307-002-01]
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Seven new C-14-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-beta-D-glucopyranoside (1), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5,14-triol 5-O-beta-D-glucopyranosyl-(1 ''-> 2')-beta-D-glucopyranoside (2), (-)-(5S,6E,12E)-tetradeca-6,12-dien- 8,10-diyn-1,5,14-triol 5,14-di-O-beta-D-glucopyranoside (3), (-)-(5S,6E)-tetradeca-6-en-8,10-diyn-1,5,14-triol 5-O-beta-D- glucopyranoside (4), (-)-(5S,6E,12E)-tetradeca-6,12-dien-8,10-diyn-1,5-14-triol 5-O-beta-D-glucopyranosyl-(1 ''-> 2')-beta-D-glucopyranoside (5), (-)-(6S,4E,12E)-tetradeca-6,12-dien-8,10-diyn-1,6-diol 6-O-beta-D-glucopyranosyl-(1 ''-> 2')-beta-D-glucopyranoside (6), and (-)-(5S,6E)-tetradeca-6-en-1,5-epoxy-8,10-diyn-14-ol 14-O-beta-D-glucopyranosyl-(1 ''-> 2')-beta-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 H-1 NMR data of the glucose with an authentic sugar sample and application of modified Mosher's method based on the MPA determination rule of Delta delta(RS) values for 1a and 4a, and (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.
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