Polyphenolic constituents of cynomorium songaricum Rupr. and antibacterial effect of polymeric proanthocyanidin on methicillin-resistant staphylococcus aureus

Shangwu Jin, Eerdunbayaer, Airi Doi, Teruo Kuroda, Guixia Zhang, Tsutomu Hatano, Guilin Chen

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Oligomeric and polymeric flavan-3-ols were obtained by chromatographic fractionation of extracts from Cynomorium songaricum Rupr. The structure of the polymeric constituent, cynomoriitannin, was characterized using spectral and chemical data. Results from acid-catalyzed degradation indicated that cynomoriitannin is a polymeric proanthocyanidin predominantly composed of epicatechin, together with low proportions of epicatechin-3-O-gallate and catechin as extension units. The terminal unit was chiefly composed of catechin, with an admixture of epicatechin. Size exclusion chromatographic analysis demonstrated a mean polymerization degree of 14. Two new phloroglucinol adducts (cynomoriitannin-phloroglucinol adducts A and B) obtained by acid-catalyzed degradation of cynomoriitannin in the presence of phloroglucinol were characterized using spectral analyses. Six oligomeric flavan-3-ols were also identified as follows: procyanidin B3, catechin-(6'-8)-catechin, catechin-(6′-6)-catechin, epicatechin-(4β-8)- epicatechin-(4β-8) -catechin, epicatechin-(4β-6)-epicatechin-(4β-8)-catechin, and arecatannin A1, respectively. These flavan-3-ols were isolated from C. songaricum. This is the first time that this procedure has been described. The antibacterial activity of the fractions and constituents was tested against methicillin-resistant Staphylococcus aureus (MRSA). The crude acetone-water (7:3) extract had moderate activity against MRSA. Cynomoriitannin was the most effective of the plant constituents against MRSA.

Original languageEnglish
Pages (from-to)7297-7305
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume60
Issue number29
DOIs
Publication statusPublished - Jul 25 2012

Fingerprint

Cynomorium
Methicillin
Catechin
Methicillin-Resistant Staphylococcus aureus
catechin
proanthocyanidins
epicatechin
polyphenols
flavanols
Phloroglucinol
degradation
methicillin-resistant Staphylococcus aureus
proanthocyanidin
acids
extracts
polymerization
acetone
Degradation
fractionation
Acids

Keywords

  • antibacterial effect
  • Cynomorium songaricum Rupr.
  • methicillin-resistant Staphylococcus aureus, phloroglucinol adducts
  • Proanthocyanidin

ASJC Scopus subject areas

  • Agricultural and Biological Sciences(all)
  • Chemistry(all)

Cite this

Polyphenolic constituents of cynomorium songaricum Rupr. and antibacterial effect of polymeric proanthocyanidin on methicillin-resistant staphylococcus aureus. / Jin, Shangwu; Eerdunbayaer; Doi, Airi; Kuroda, Teruo; Zhang, Guixia; Hatano, Tsutomu; Chen, Guilin.

In: Journal of Agricultural and Food Chemistry, Vol. 60, No. 29, 25.07.2012, p. 7297-7305.

Research output: Contribution to journalArticle

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abstract = "Oligomeric and polymeric flavan-3-ols were obtained by chromatographic fractionation of extracts from Cynomorium songaricum Rupr. The structure of the polymeric constituent, cynomoriitannin, was characterized using spectral and chemical data. Results from acid-catalyzed degradation indicated that cynomoriitannin is a polymeric proanthocyanidin predominantly composed of epicatechin, together with low proportions of epicatechin-3-O-gallate and catechin as extension units. The terminal unit was chiefly composed of catechin, with an admixture of epicatechin. Size exclusion chromatographic analysis demonstrated a mean polymerization degree of 14. Two new phloroglucinol adducts (cynomoriitannin-phloroglucinol adducts A and B) obtained by acid-catalyzed degradation of cynomoriitannin in the presence of phloroglucinol were characterized using spectral analyses. Six oligomeric flavan-3-ols were also identified as follows: procyanidin B3, catechin-(6'-8)-catechin, catechin-(6′-6)-catechin, epicatechin-(4β-8)- epicatechin-(4β-8) -catechin, epicatechin-(4β-6)-epicatechin-(4β-8)-catechin, and arecatannin A1, respectively. These flavan-3-ols were isolated from C. songaricum. This is the first time that this procedure has been described. The antibacterial activity of the fractions and constituents was tested against methicillin-resistant Staphylococcus aureus (MRSA). The crude acetone-water (7:3) extract had moderate activity against MRSA. Cynomoriitannin was the most effective of the plant constituents against MRSA.",
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AU - Kuroda, Teruo

AU - Zhang, Guixia

AU - Hatano, Tsutomu

AU - Chen, Guilin

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AB - Oligomeric and polymeric flavan-3-ols were obtained by chromatographic fractionation of extracts from Cynomorium songaricum Rupr. The structure of the polymeric constituent, cynomoriitannin, was characterized using spectral and chemical data. Results from acid-catalyzed degradation indicated that cynomoriitannin is a polymeric proanthocyanidin predominantly composed of epicatechin, together with low proportions of epicatechin-3-O-gallate and catechin as extension units. The terminal unit was chiefly composed of catechin, with an admixture of epicatechin. Size exclusion chromatographic analysis demonstrated a mean polymerization degree of 14. Two new phloroglucinol adducts (cynomoriitannin-phloroglucinol adducts A and B) obtained by acid-catalyzed degradation of cynomoriitannin in the presence of phloroglucinol were characterized using spectral analyses. Six oligomeric flavan-3-ols were also identified as follows: procyanidin B3, catechin-(6'-8)-catechin, catechin-(6′-6)-catechin, epicatechin-(4β-8)- epicatechin-(4β-8) -catechin, epicatechin-(4β-6)-epicatechin-(4β-8)-catechin, and arecatannin A1, respectively. These flavan-3-ols were isolated from C. songaricum. This is the first time that this procedure has been described. The antibacterial activity of the fractions and constituents was tested against methicillin-resistant Staphylococcus aureus (MRSA). The crude acetone-water (7:3) extract had moderate activity against MRSA. Cynomoriitannin was the most effective of the plant constituents against MRSA.

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