Polyoxygenated Xanthones from Centaurium erythraea Roots

Tetraoxygenated naturally occurring xanthones

“…In a review of Hypericum genus, Kitanov and Blinova (1987) listed only ®ve simple tetraoxygenated xanthones; two years later, in a review of xanthones from 1-Hydroxy-2,3,7-trimethoxyxanthone (4) F. caroliniensis [313] Halenia elliptica [38,87] Veratrilla baillonii [348] 1-Hydroxy-3,4,5-trimethoxyxanthone (5) Frasera albicaulis [314] 1-Hydroxy-3,4,7-trimethoxyxanthone (6) Frasera albicaulis [314] F. albomarginata [90] 1-Hydroxy-3,5,6-trimethoxyxanthone (7) Canscora decussata [108] Centaurium erythraea [190] Hoppea dichotoma [110] (Haploxanthone) Calophyllum apetalum [165] Calophyllum bracteatum [312] C. inophyllum [171] C. tomentosum [28] C. trapezifolium [128] Centaurium linarifolium [114] Kayea stylosa [131] Monnina obtusifolia [283] Pentadesma butyracea [81] Tovomita pyrifolium [245] 1,3,5-Trihydroxy-6-methoxyxanthone (68)…”

Monohydroxy- and 2,5-Dihydroxy Terephthalic Acids, Two Unusual Phenolics Isolated from Centaurium erythraea and Identified in Other Gentianaceae Members

“…In compound 1, the 1,2,4-trisubstituted aromatic ring was deduced from the 'H-nmr spectrum (DMSO-</6) exhibiting three protons at 7.86 (d, 7 = 7.6 Hz, H-6), 7.41 (dd,7 = 7.6, 1.6 Hz, H-5), and 7.39 (d, 7= 1.6 Hz, H-3). The low-field region of the [2], Salicylic Acid {5}, 2,3-Dihydroxybenzoic Acid [6], and 2,5-Dihydroxybenzoic Acid [7] (50 MHz; DM §0-<4; ppm/TMS). effect of the involved substituent.…”

“…Centaurium erythraea Rafn. (Gentianaceae) has been the subject of previous phytochemical analysis identifying terpenoids (iridoids and secoiridoids) (1,2), polyphenols as flavonols (3) and their />-coumaroyl-di-and and tri-Oglycosides (4), xanthones characterized by a high oxygenation level (5,6), and, finally, phenolic acids belonging to the benzoic, cinnamic, and phenylacetic groups (4,7). We report here the findings of an examination of a sample of aerial parts from which the terephthalic acids 1 and 2 were isolated; these compounds have been also identified in the MeOH extract of the roots of this species and in other gentianaceous plants.…”

Acute and sub-chronic toxicity of a lyophilised aqueous extract of Centaurium erythraea in rodents

“…The toxicity and lethality of the CE-extract may be due to any one or more of the phytochemicals present in the crude aqueous extract, some of which have been isolated and identified (Van Der Sluis and Labadie, 1981;Takagi et al, 1982;Kaouadji et al, 1986;Hatjimanoli et al, 1988). The flavonoids, which are abundant in the aqueous extract of Centaurium erythraea have not been reported to be toxic (Duke, 2000).…”

“…Centaurium erythraea has been the subject of several phytochemical investigations, which have resulted in the isolation and identification of a variety of compounds, including, centauroside, centapicrin, flavonoids, gentiopicrin, gentiopicroside, isocoumarin, phenolic acids, swertiamarin, triterpenes, wertiamarine, and xanthones (Van Der Sluis and Labadie, 1981;Takagi et al, 1982;Kaouadji et al, 1986;Hatjimanoli et al, 1988;Schimmer and Mauthner, 1994;Jovanović et al, 2009;Valentão et al, 2000;Valentão et al, 2002;Kumarasamy et al, 2003a;Valentão et al, 2003a;Van Wyk and Wink, 2004;Schimmer and Mauthner, 1996;Bellakhdar, 2006). In addition, several steroids (␤-sitosterol, stigmasterol, campesterol, brassicasterol and ␦ 7 -stigmasterol), and essential amino acids (alanine, leucine, phenylalanine and tryptophan) have also been identified in centaury (Aquino et al, 1985).…”