A novel naphthoquinone glycoside from Rubia peregrina L.

ÖZGEN U., KAZAZ C., SEÇEN H., ÇALIŞ İ., Coskun M., Houghton P. J.

TURKISH JOURNAL OF CHEMISTRY, vol.33, no.4, pp.561-568, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 4
  • Publication Date: 2009
  • Doi Number: 10.3906/kim-0806-28
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.561-568
  • Keywords: Rubia peregrina, Rubiaceae, anthraquinones, iridoid glycosides, naphthoquinone glycoside, NATURALLY OCCURRING QUINONES, IRIDOID GLUCOSIDES, ANTHRAQUINONES, CORDIFOLIA, NAPHTHOHYDROQUINONES, GALIUM
  • Karadeniz Technical University Affiliated: No


A phytochemical study was performed on the subterranean parts (roots and rhizomes) of Rubia peregrina. The substances were isolated from chloroform, ethyl acetate, and water soluble parts of the methanolic extract using several chromatographic techniques. 1-Hydroxy-2-methyl-9,10-anthraquinone (1), 1,3-dihydroxy-2-methyl-9,10-anthraquinone (2), and 1,3-dihydroxy-2-methoxymethyl-9,10-anthraquinone (3) were isolated from the chloroform phase; and asperuloside (4), asperulosidic acid (5), rubiadin 3-O-beta-primeveroside (6), lucidin 3-O-beta-primeveroside (7), deacetylasperulosidic acid (8), liriodendrin (9), and a new naphthoquinone glycoside, 2-hydroxy-3-O-beta-primeveroside naphthalene-1,4-dione (inkumoside, 10), from the aqueous phase. The structures of the compounds were elucidated by means of spectral analysis ((1)H-NMR, (13)C-NMR, (2)D-NMR-COSY, HMBC, HMQC-, EI-MS and ESI-MS).