Three New Polyyne (=Polyacetylene) Glucosides from the Edible Roots of Codonopsis cordifolioidea

Abstract

Three new linear C 14 polyyne (¼ polyacetylene) glucosides, cordifolioidynes A -C (1 -3), together with two known polyynes, lobetyol (4) and lobetyolin (5), and five known phenylpropanoids, i.e., sinapinaldehyde (6), coniferaldehyde (7), coniferoside (8), sachaliside (9), and isoconiferin (10), were isolated from the roots of Codonopsis cordifolioidea. The structures of 1 -3 were established from spectral evidences and by characterization of their hydrolysis products. Acid hydrolysis of 1 afforded the aglycone 1a, while hydrolysis of 2 and 3 gave the cyclization products 2a and 3a, respectively. Compounds 4 -10 were isolated from this plant for the first time. The antibacterial activity of compounds 1 -5 were assessed against eight microbial strains by the agar dilution method, none of them exhibited antibacterial effects at concentrations up to 100 mg/ml.

C14-Polyacetylene glucosides fromCodonopsis pilosula

“…Besides resonances corresponding to proton-bearing carbons of the above units, the 13 C NMR and DEPT spectra of 1 showed four quaternary carbon resonances assignable to two triple bonds (d C 80.8, 80.2, 74.2, and 73.4). These spectral data were consistent with those of cordifolioidyne B, which was isolated from C. cordifolioidea [15]. 2D NMR data analysis confirmed that 1 possessed a planar structure identical to that of cordifolioidyne B.…”

“…10,MeOH)]. In addition, the absolute configuration at C-5 in cordifolioidyne B was not determined in the previous report, and acid hydrolysis of cordifolioidyne B did not generate a genuine aglycone instead of a dehydrated cyclization product of the aglycone [15]. To determine the absolute configuration of 1, enzymatic hydrolysis and modified Mosher's method based on the MPA determination rule of Dd RS values [16] were applied.…”

Constituents of the flowers of Platycodon grandiflorum with inhibitory activity on advanced glycation end products and rat lens aldose reductase in vitro

“…Fifteen compounds (1-15) were isolated from an EtOAc-soluble fraction of the flowers of P. grandiflorum, and were identified as apigenin (1) (Lee et al, 1988), apigenin-7-O-β-D-glucopyranoside (2) (Lee et al, 1988), apigenin-7-O-(6''-O-acetyl)-β-D-glucopyranoside (3) (Švehlíková et al, 2004), luteolin (4) (Lee et al, 1988;Han et al, 2007), luteolin-7-O-β-D-glucopyranoside (5) (Lee et al, 1988;Han et al, 2007), luteolin-7-O-(6''-O-acetyl)-β-D-glucopyranoside (6) , isorhamnetin-3-O-neohesperidoside (7) (Chaurasia and Wichtl, 1987), 4-O-caffeoylquinic acid (8) (Tatefugi et al, 1996), chlorogenic acid methyl ester (9) (Jung et al, 1999), 4-O-β-D-glucopyranosylcaffeic acid (10) (Cui et al, 1990), lobetyolin (11) (Ishimaru et al, 1991), cordifolioidyne C (12) (Mei et al, 2008), isomultiflorenyl acetate (13) (Faure and Gaydou, 1991), β-sitosterol glucoside (14) , and α-spinosterol (15) (Choi et al, 2003), by spectroscopic methods as well as by comparison of their data with literature values (Fig. 1).…”

HPLC/UV Analysis of Polyacetylenes, Phenylpropanoid and Pyrrolidine Alkaloids in Medicinally UsedCodonopsisSpecies

“…To exclude TFA from the compounds obtained, codonopyrrolidium B (1) and codonopyrrolidium A (2) were each dissolved in 0.5% hydrochloric acid and then subjected to an ODS-A column (1.5 cm × 20 cm). C NMR spectra are shown as online Supporting information) with data reported in the literature (Mizutani et al, 1988;Ishimaru et al, 1991Ishimaru et al, , 1992 Mei et al, 2008;Tsai and Lin, 2008). The purity of each compound was confirmed by HPLC/DAD to be higher than 97% at six wavelengths (205, 215, 230, 254, 267 and 284 nm).…”

“…Fraction E‐6‐5 was subjected to a Sephadex LH‐20 column (2.5 cm × 70 cm) and eluted with H 2 O/MeOH (1:1, v/v; 4.0 L) to obtain lobetyolinin ( 5 ) (7.0 mg). All of the isolated compounds were identified by comparison of their spectral data (MS, 1 H NMR and 13 C NMR spectra are shown as online Supporting information) with data reported in the literature (Mizutani et al ., ; Ishimaru et al ., , ; Cuendet et al ., ; Mei et al ., ; Tsai and Lin, ). The purity of each compound was confirmed by HPLC/DAD to be higher than 97% at six wavelengths (205, 215, 230, 254, 267 and 284 nm).…”