Showing papers on "Flavanone published in 1981"
TL;DR: The mutagenicities of 61 flavonoids and those of 11 compounds structurally related to flavonoid compounds were tested with Salmonella typhimurium strains TA100 and TA98 and it was found that quercetin was the strongest mutagen.
Abstract: The mutagenicities of 61 flavonoids (naturally occurring flavonoid aglycones and flavonal glycosides and synthetic flavonoids) and those of 11 compounds structurally related to flavonoids were tested with Salmonella typhimurium strains TA100 and TA98. Among the 22 flavone derivatives tested, only wogonin was strongly mutagenic, while five derivatives, apigenin triacetate, acacetin, chrysoeriol, pedalitin, and pedalitin tetraacetate, were only weakly mutagenic. Two bisflavonyl derivatives, neither of which has a 3-hydroxyl group, were not mutagenic. Of the 16 flavonol derivatives tested, all except 3-hydroxyflavone and the tetra- and penta-methyl ethers of quercetin were mutagenic. Of the five flavanone derivatives tested, only 7,4-dihydroxyflavanone was mutagenic, showing weak activity. Of the four flavanonol derivatives tested, hydrorobinetin and taxifolin were weakly mutagenic. Of the six isoflavone derivatives tested, tectorigenin was weakly mutagenic. Of the 11 compounds in the miscellaneous group structurally related to flavonoids, only iso-liquiritigenin was mutagenic, showing weak activity. For the emergence of strong mutagenicity, the double bond between positions 2 and 3 and the hydroxyl group at position 3 are required, except in wogonin, which does not have a hydroxyl group at position 3 but is strongly mutagenic to TA100. The 3-O-acetyl ester of flavonol, quercetin, was mutagenic with S9 mix, but 3-O-methyl ethers were not. Six flavonol glycosides, three quercetin glycosides and three kaempferol glycosides were mutagenic after preincubation with “hesperidinase,” a crude extract of Aspergillus niger. Of 66 flavonoid agylcones and compounds structurally related to flavonoids, quercetin was the strongest mutagen. The carcinogenicity of this compound should be clarified because it is ubiquitously found in vegetables.
177 citations
TL;DR: It is postulate that synthesis of flavone and flavonol from flavanone proceeds via 2-hydroxy- and 2,3-dihydroxyflavanone, respectively, with subsequent dehydration, and in vitro biosynthesis of radioactive flavone, dihydroflavonol and flav onol from [2-14C]malonyl-CoA and 4-coumaroyl- CoA in good yield and with high specific activity is possible.
Abstract: Abstract Soluble enzyme preparations from irradiated cell suspension cultures of parsley (Petroselinum hortense Hoffm.) catalyse the conversion of flavanone to flavone, dihydroflavonol and flavonol. These reactions require 2-oxoglutarate, Fe2+ and ascorbate as cofactors. In the presence of these cofactors conversion of dihydroflavonol to flavonol was also observed. With this system in vitro biosynthesis of radioactive flavone, dihydroflavonol and flavonol from [2-14C]malonyl-CoA and 4-coumaroyl-CoA in good yield and with high specific activity is possible. We postulate that synthesis of flavone and flavonol from flavanone proceeds via 2-hydroxy-and 2,3-dihydroxyflavanone, respectively, with subsequent dehydration. The microsomal fraction of the parsley cells contains an NADPH-dependent flavanone 3'-hydroxylase.
127 citations
TL;DR: 3-Methylene-2-phenylflavanone was synthesized and shown to be equal to hexachlorophene in tests against representative Gram-positive microorganisms.
Abstract: The antimicrobial activity previously attributed to flavanone Mannich bases was found to be due to their breakdown products, 3-methyleneflavanones. Among the latter compounds, highest potency was observed when the flavanone phenyl ring contained bromine or chlorine substituents. 3-Methylene-2-phenylflavanone (8) was synthesized and shown to be equal to hexachlorophene in tests against representative Gram-positive microorganisms.
51 citations
TL;DR: A new flavanone, named euchrestalfavanone A (I), mp 145-147°C, C25H28O5, was isolated from the root of Euchresta japonica HOOK as mentioned in this paper.
Abstract: A new flavanone, named euchrestalfavanone A (I), mp 145-147°C, C25H28O5, was isolated from the root of Euchresta japonica HOOK. f. ex REGEL (Leguminosae) together with l-maackiain, medicagol and trifolirhizin. The structure of I was established to be 6, 3'-di-γ, γ-dimethylallyl-5, 7, 4'-trihydroxyflavanone on the basis of chemical and spectral evidence.
31 citations
TL;DR: In this paper, a dihydrochalcone, a flavone, four 3-methylflavonols, one flavanone, and a 3 methylflavanonol were isolated from the roots of Derris araripensis.
28 citations
TL;DR: In this paper, four flavonoids in the seeds of Tephrosia bracteolata were identified as the flavanone obovatin methyl ether and the flavones isopongaflavone, trans-tephrostachin and trans-anhydrrhythmic phyllostachin.
25 citations
TL;DR: A new flavanone glucoside, plantagoside (1) was isolated from the seeds of Plantago major var. japonica NAKAI (Plantaginaceae) together with aucubin, geniposidic acid, acteoside and syringin this paper.
Abstract: A new flavanone glucoside, plantagoside (1) was isolated from the seeds of Plantago major var. japonica NAKAI (Plantaginaceae) together with aucubin, geniposidic acid, acteoside and syringin. The structure of plantagoside was elucidated to be 1 on the basis of chemical and spectral evidence.
24 citations
TL;DR: Onitinoside and onysilin were identified by spectral and chemical methods as 4-O-glucosyl-6-(2′-hydroxyethyl)-2,2,5,7-tetramethylindan-1-one and 5-hydrox-6, 7-dimethoxyflavanone, respectively as discussed by the authors.
21 citations
TL;DR: In this article, a new 8-aryl-flavanone has been isolated and shown to be (2,4-dihydroxy-6-methoxy) tolyl-3-(5,7-dimethyl 6-methyl) flavanonyl-8-phenylmethane.
20 citations
TL;DR: A chemical investigation of Didymocarpus pedicellata has resulted in the isolation of 8-hydroxy-5, 6, 7-trimethoxy-flavanone, 2'-Hydroxy-4', 5', 6'-trIMethoxychalcone, pediceLLin, methyl pedicin and beta-sitosterol.
Abstract: A chemical investigation of Didymocarpus pedicellata has resulted in the isolation of 8-hydroxy-5, 6, 7-trimethoxy-flavanone, 2'-hydroxy-4', 5', 6'-trimethoxychalcone, 5, 6, 7, 8-tetramethoxy flavanone, pedicellin, methyl pedicin and beta-sitosterol. 8-Hydroxy-5, 6, 7-trimethoxy flavanone and 2'-hydroxy-4', 5', 6'-trimethoxy chalcone are hitherto new natural products while 5, 6, 7, 8-tetramethoxy flavanone has been isolated from D. pedicellata for the first time.
12 citations
TL;DR: The chemical evidence supports the view that the Coriaria family is an isolated one with no close relatives, and a tentative but distant relationship with the group Anacardiaceae-Rutaceae-Meliaceae might be suggested.
Abstract: Twelve species of Coriaria, the sole genus of Coriariaceae, were ex- amined for flavonoid constituents. The major compounds identified were 3-0-mono- glycosides of quercetin and kaempferol comprising glucosides, galactosides, arabin- osides, xylosides, and rhamnosides. Diglycosides isolated were the 3-0-rutinosides of both flavonols plus small amounts of the 3-O-xylosylglucosides (or 3-O-glucosylxy- losides). Naringenin-7-O-,8-D-glucopyranoside was observed as a major constituent of most taxa. The distribution of these compounds was very homogeneous among the species tested, giving no support to Good's three "groups." A comparison of flavonoid data obtained in this study with published information concerning those families with which Coriariaceae has been allied showed no close relationships. On the basis of flavanone distribution a tentative but distant relationship with the group Anacardiaceae-Rutaceae-Meliaceae might be suggested. The chemical evidence, however, supports the view that the family is an isolated one with no close relatives.
TL;DR: The isolation and identification of a new glycoside, f-riodietyol 5-O - methyl ether 7- O -β- D -xylosyigalactoside from whole plant of the fern Diplazium esculentum is reported.
TL;DR: The trunk wood of Qualea labouriauana contains (2 R )-5,7,4′-trihydroxy-3′-methoxy-6,8-dimethylflavanone, ( 2 R ) -5, 7, 4′ -trihydrox-8-methylflanone, the biosynthetically interesting 2,2′-dihydroxy-4,6, 4.6′,6′-tetramethoxy -3, 3′-dimethylbenzophenone.
TL;DR: Two new flavonoid glycosides, naringenin 7-galactosyl(1 → 4)glucoside and dihydroquercetin 5- galactoside, have been characterized from stem tissue of Dillenia pentagyna.
TL;DR: A new flavanone glycoside was isolated from the aerial parts of Nierembergia hippomanica and identified as the 4‴-acetate of pinocembrin 7-neohesperidoside.
TL;DR: In this paper, the isolation and identification of a new glycoside, eriodictyol 5-O -methyl ether 7- O -β-D -xylopyranosyl-β- D -arabinopyranoide, from seeds of Sapium sebiferum is reported.
Journal Article•
TL;DR: In this paper, six flavanones have been isolated for the first time from Siberian tansy, and two of them have proved to be new compounds, one of which is a new compound.
Abstract: Six flavanones have been isolated for the first time from Siberian tansy, and two of them have proved to be new compounds.
TL;DR: In this paper, methoxy-chalcone and flavanone derivatives were obtained by the methylation of the hydrolysis products of safflomin-A (1), a yellow component of the flowers of Safflower (Carthamus tinctorius L.).
Abstract: New methoxy-chalcone and flavanone derivatives were obtained by the methylation of the hydrolysis products of safflomin-A (1), a yellow component of the flowers of Safflower (Carthamus tinctorius L.). The formation of these derivatives significantly contributes to the elucidation of the structure of 1, proposed by us.
TL;DR: In this article, the relative contribution and π,π* character in the lowest triplet states were discussed in terms of relative contribution of parent and substituted flavanones and 4-chromanone in 2-propanol.
Abstract: Parent and substituted flavanones undergo photochemical opening of the pyrone ring to give corresponding 2′-hydroxychalcones in benzene, pyridine, acetonitrile etc., the yields varying from 0 to 70% with substituents. The reaction is depressed by the addition of 1,3-pentadiene, nitrosobenzene, or acrylonitrile. On the other hand, flavanone and 4-chromanone undergo photoreduction in 2-propanol to give reductive coupling products and solvent adducts as isomeric mixtures. 7,8-Benzoflavanone does not undergo photoreduction in 2-propanol but the ring opening reaction instead. Mechanisms have been discussed in terms of the relative contribution and π,π* character in the lowest triplet states.