A novel naphthoquinone glycoside from Rubia peregrina L.

Authors

UFUK ÖZGEN
CAVİT KAZAZ
HASAN SEÇEN
İHSAN ÇALIŞ
MAKSUT COŞKUN
PETER J. HOUGHTON

DOI

10.3906/kim-0806-28

Abstract

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 (^1H-NMR, ^{13}C-NMR, 2D-NMR--COSY, HMBC, HMQC-, EI-MS and ESI-MS).

Keywords

Rubia peregrina, Rubiaceae, anthraquinones, iridoid glycosides, naphthoquinone glycoside.

First Page

561

Last Page

568

Recommended Citation

ÖZGEN, UFUK; KAZAZ, CAVİT; SEÇEN, HASAN; ÇALIŞ, İHSAN; COŞKUN, MAKSUT; and HOUGHTON, PETER J. (2009) "A novel naphthoquinone glycoside from Rubia peregrina L.," Turkish Journal of Chemistry: Vol. 33: No. 4, Article 13. https://doi.org/10.3906/kim-0806-28
Available at: https://journals.tubitak.gov.tr/chem/vol33/iss4/13