Purification and identification of flavanone glycosides in the peel of the sweet orange.
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Bioactivity directed fractionation of the acetone extract of Teloxys graveolens (Willd.) Weber (Chenopodiaceae), using the brine shrimp lethality test, led to the isolation of 5,7-dihydroxyflavanone (pinocembrine) (LC50 = 4.25 micrograms/ml) as the only active compound. Pinocembrine also exhibited fasciolicide, ovicide and larvicide activities on newly excysted Fasciola hepatica, on infective eggs of Ascaridi galli and on stage three larvae of Stomoxys calcitrans, respectively.
The HPLC enantiomeric separation of naringenin, eriodictyol, hesperetin and pinocembrin was accomplished in the normal-phase mode using two polysaccharide-derived chiral stationary phases (Chiralcel OD-H and Chiralpak AS-H) and various n-hexane/alcohol mobile phases. The 3',4' substituents pattern affect the enantioselectivity of these phases. Single enantiomers of naringenin were isolated by semipreparative HPLC and their CD spectra were measured and related to the absolute configuration by the exciton-coupling method. Online coupling HPLC/spectropolarimeter afforded the CD sign of the eluted peaks at a single wavelength, and the complete CD spectra of the eluted enantiomers were obtained by trapping them in the spectropolarimeter cell through a switching valve.
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Citrus flavonoids have been investigated for their biological activity, with both anti-inflammatory and -carcinogenic effects being reported. However, little information is known on the bioavailability of these compounds in vivo. The objectives of this study were to determine the tissue distribution of naringenin after gastric gavage of [3H]-naringenin to rats. Unlabelled naringenin was also used to quantify the levels of naringenin and its major metabolites in tissues and eliminated in the urine and faeces. Significant radioactivity was detected in the plasma as well as all tissues examined 2h post-gavage. After 18h, higher levels of radioactivity were retained in plasma and tissues (55% of the administered radioactivity). Investigation of the nature of metabolites, using unlabelled naringenin, revealed that the glucuronides were the major components in plasma, tissues and urine, in addition to the colonic metabolite 3-(4-hydroxyphenyl) propionic acid, detected in the urine. The aglycone was the form extensively retained in tissues after 18h post-gavage. Total identified metabolites detected after 18h in most tissues were only 1-5% of the levels detected after 2h. However, the brain, lungs and heart retained 27, 20 and 11%, respectively, relative to the total metabolites detected at 2h. While radioactive detection suggests increased levels of breakdown products of naringenin after 18 h versus 2 h, the products identified using unlabelled naringenin are not consistent with this, suggesting that a predominant proportion of the naringenin breakdown products at 18 h are retained as smaller decomposition molecules which cannot yet be identified.
A new gamma-lactone derivative named davallialactone (4) and the 7-O-beta-D-glucuronide of (+/-)-eriodictyol (5a) have been isolated from Davallia mariessi Moore along with caffeic acid (1), 4-beta-D-glucopyranosylcaffeic acid (2) and 4-O-beta-D-glucopyranosyl-p-coumaric acid (3). The structures of the new compounds were determined by chemical and spectroscopic methods including two-dimensional nuclear magnetic resonance (2D NMR) techniques, especially 1H-detected heteronuclear multiple-bond multiple-quantum coherence and long-range C-H J-resolved 2D NMR techniques.
A series of novel flavonoids comprising structural elements present in the antineoplastic agents podophyllotoxin and etoposide was synthesized. These oxygen-containing analogues of antiproliferative quinolones moderate cytotoxicity towards L1210 and HT-29 cell lines.
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AIM: To study the chemical constituents of Dryopteris sublaeta Ching et Hsu. METHODS: Fresh plant of Dryopteris sublaeta Ching et Hsu was extracted twice with boiling water, the extract was concentrated to small volume under reduced pressure at 50 degrees C. The concentrated material was partitioned with ether, ethyl acetate, and n-butanol. The fraction of ether extract was chromatographed over silica gel column. The compounds were identified on the basis of their physiochemical and spectral data. RESULTS: Four compounds were obtained and identified as 2 (S)-5, 7, 3'-trihydroxy-6, 8-dimethyl-5'-methoxyflavanone (1), matteucinol (2), desmethoxymatteucinol (3) and 5, 7, 2'-trihydroxy-6, 8-dimethylflavanone (4). CONCLUSION: Compound 1 is a new one, the others were isolated from Dryopteris for the first time.
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