New isoflavone glycosides from Iris spuria L. (Calizona) cultivated in Egypt

Salwa F. Farag, Yuka Kimura, Hideyuki Ito, Junko Takayasu, Harukuni Tokuda, Tsutomu Hatano

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Two new isoflavone glycosides, tectorigenin 7-O-β-d-glucopyranoside- 4′-O-[β-d-glucopyranosyl-(1‴′ → 6‴)-β-d-glucopyranoside] (1) and iristectorigenin B 4′-O-[β-d-glucopyranosyl-(1‴ → 6″)-β-d- glucopyranoside] (2), together with 11 known compounds, including six isoflavones, tectorigenin 7-O-β-d-glucopyranoside-4′-O-β-d- glucopyranoside (3), tectorigenin 4′-O-[β-d-glucopyranosyl-(1‴ → 6″)-β-d-glucopyranoside] (4), tectorigenin 7-O-β-d-glucopyranoside (5), genistein 7-O-β-d-glucopyranoside (6), tectorigenin 4′-O-β-d-glucopyranoside (7), and tectorigenin (8); two phenolic acid glycosides, vanillic acid 4-O-β-d-glucopyranoside (9) and glucosyringic acid (10); a phenylpropanoid glycoside, E-coniferin (11); an auronol derivative, maesopsin 6-O-β-d-glucopyranoside (12); and a pyrrole derivative, 4-(2-formyl-5-hydroxymethylpyrrol-1-yl) butyric acid (13), were isolated from fresh Iris spuria (Calizona) rhizomes. The structures of these compounds were established on the basis of spectroscopic and chemical evidence. Inhibitory effects on the activation of Epstein-Barr virus early antigen were examined for compounds 1-8 and 12.

Original languageEnglish
Pages (from-to)91-95
Number of pages5
JournalJournal of Natural Medicines
Volume63
Issue number1
DOIs
Publication statusPublished - Jan 2009

Fingerprint

Isoflavones
Egypt
Iris
Glycosides
Vanillic Acid
Derivatives
Rhizome
Pyrroles
Butyric Acid
Genistein
tectorigenin
Chemical activation

Keywords

  • Auronol
  • Iridaceae
  • Iris spuria
  • Isoflavone glycosides
  • Phenolic acid glycosides
  • Phenylpropanoid glycoside

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Complementary and alternative medicine

Cite this

New isoflavone glycosides from Iris spuria L. (Calizona) cultivated in Egypt. / Farag, Salwa F.; Kimura, Yuka; Ito, Hideyuki; Takayasu, Junko; Tokuda, Harukuni; Hatano, Tsutomu.

In: Journal of Natural Medicines, Vol. 63, No. 1, 01.2009, p. 91-95.

Research output: Contribution to journalArticle

Farag, Salwa F. ; Kimura, Yuka ; Ito, Hideyuki ; Takayasu, Junko ; Tokuda, Harukuni ; Hatano, Tsutomu. / New isoflavone glycosides from Iris spuria L. (Calizona) cultivated in Egypt. In: Journal of Natural Medicines. 2009 ; Vol. 63, No. 1. pp. 91-95.
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AB - Two new isoflavone glycosides, tectorigenin 7-O-β-d-glucopyranoside- 4′-O-[β-d-glucopyranosyl-(1‴′ → 6‴)-β-d-glucopyranoside] (1) and iristectorigenin B 4′-O-[β-d-glucopyranosyl-(1‴ → 6″)-β-d- glucopyranoside] (2), together with 11 known compounds, including six isoflavones, tectorigenin 7-O-β-d-glucopyranoside-4′-O-β-d- glucopyranoside (3), tectorigenin 4′-O-[β-d-glucopyranosyl-(1‴ → 6″)-β-d-glucopyranoside] (4), tectorigenin 7-O-β-d-glucopyranoside (5), genistein 7-O-β-d-glucopyranoside (6), tectorigenin 4′-O-β-d-glucopyranoside (7), and tectorigenin (8); two phenolic acid glycosides, vanillic acid 4-O-β-d-glucopyranoside (9) and glucosyringic acid (10); a phenylpropanoid glycoside, E-coniferin (11); an auronol derivative, maesopsin 6-O-β-d-glucopyranoside (12); and a pyrrole derivative, 4-(2-formyl-5-hydroxymethylpyrrol-1-yl) butyric acid (13), were isolated from fresh Iris spuria (Calizona) rhizomes. The structures of these compounds were established on the basis of spectroscopic and chemical evidence. Inhibitory effects on the activation of Epstein-Barr virus early antigen were examined for compounds 1-8 and 12.

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