NMR spectral analysis of flavonoids from Chrysanthemum coronarium

Abstract

analyses. 1-and 2-dimensional NMR spectroscopy of the rare naringenin 5-O-glucoside have been recorded and assigned for the first time. The flavonoid glucosides from Chrysanthemum coronarium showed week activity against Poliovirus I and Adenovirus type 7.Chrysanthemum coronarium L. (Compositae) is regarded in East Asia as a healthy vegetable because the edible portion contains abundant nutrients [1] as well as a fresh flavor [2]. This species is occasionally used as folk medicine [3] and has been found to have biologically active substances [4][5][6][7]. The elucidation of the bioactive substances from this plant is of a great importance to increase its vegetable value. It is used in Egyptian traditional medicine [8]. It was reported that the plant contained terpenes [4], sterols, polyacetylenes [6], anthraquinones [9], and flavonoids [9,10]. In the course of our continuous studies on this plant, naringenin 5-O-glucoside (1) [11, 12] as a rare flavanone glucoside was isolated with two flavone glucosides, apigenin 7-O-β-glucoside (2) and luteolin 7-O-β-glucoside (3); two aglycones, apigenin (4) and luteolin (5); two flavonol glucosides, kaempferol 3-O-β-glucoside (6) and quercetin 3-O-β-glucoside (isoquercitrin) (7) [11,13]; and two aglycones, kaempferol (8) and quercetin (9). 2: R = R 2 = H, R 1 = Glc; 3: R = OH, R 1 = Glc, R 2 = H 4: R = R 1 = R 2 = H; 5: R = OH, R 1 = R 2 = H 6: R = R 1 = H, R 2 = OGlc; 7: R 1 = H, R = OH, R 2 = OGlc 8: R = R 1 = H, R 2 = OH; 9: R = OH, R 1 = H, R 2 = OH Ground dry shrublets of C. coronarium were exhaustively extracted with 70% ethanol/water, and the extract was concentrated under reduced pressure. The aqueous residue was extracted with solvents of increasing polarity. The fractions were subjected to repeated column chromatography to yield nine compounds.

Phytochemical studies on the Australian native plant speciesAcacia pycnanthaandJacaranda mimosifoliaD.Don

“…The water-acetonitrile mixture containing compounds 1 (Velozo et al 1999) and 2 (Ibrahim et al 2007;Shimoda et al 2010), was subjected to slow evaporation at room temperature, and afforded 1 as long white-needle crystals, with 2 isolated from the filtrate after solvent evaporation. Analysis of the LRESMS spectra of 1 indicated peaks at m/z 457 and 433, assigned to [M+Na] + and [M-H]respectively.…”

A new lanostane-type triterpene and sesquiterpene lactones fromVernonia leopoldiiand theirin vitrocytotoxicity

“…and 5 were identified as apigenin-7-O-glucoside and luteolin-7-O-glucoside by comparing their physical and spectroscopic data (see Supplementary material) with those reported byErsoz et al (2002);Chiruvella et al (2007);Ibrahim et al (2007) and Kuruuzum-Uz et al…”

Caffeoylquinic Acids from the Aerial Parts of Chrysanthemum coronarium L.

“…Many previous studies have reported the isolation, identification, and the biological activities of the plant. The results have shown that flavonoids [2], phenolic acids [3], sesquiterpene lactone [4], monoterpene [5], diterpene [6], glycosyldiglycerides [7], alkaloid [8], phytosterol [9], heterocyclic compounds [8], polyacetylenes [9], and essential oils [10,11] were the major chemical constituents present in the plant. Ch.…”

“…coronarium L., which are also the main bioactive constituents of the Compositae family [2,3]. Caffeoylquinic acids (CQAs) are cinnamate conjugates, which are biosynthesized through the phenylpropanoid pathway.…”