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Showing papers on "Flavanone published in 1979"


Journal ArticleDOI
TL;DR: The results for both enzymes were in agreement with experimental data, indicating that the light-induced changes in enzyme activity can be explained by changes in the respective mRNA activity.

133 citations


Journal ArticleDOI
TL;DR: The results support the idea that the enzyme is composed of two subunits which are probably identical, and the possible similarity in mechanism between flavanone synthase and 3-oxoacyl-(acyl carrier protein) synthase is discussed.
Abstract: Flavanone synthase from irradiated cell suspension cultures of parsley was purified to apparent homogeneity. Molecular weights of about 77000 for the enzyme and about 42000 for the subunits were determined respectively by sedimentation-equilibrium measurements and disc-gel electrophoresis in the presence of dodecyl sulfate. A specific antiserum was prepared for the enzyme and was used in an assay for flavanone synthase mRNA activity in partially purified RNA preparations. The apparent molecular size of flavanone synthase mRNA was estimated by sucrose gradient centrifugation and gel electrophoresis under partially denaturing conditions. Values of about 17 S and Mr= 0.62 × 106 were obtained. The fractionation patterns suggested that flavanone synthase mRNA was homogeneous in size. All together, the results support the idea that the enzyme is composed of two subunits which are probably identical. Amino acid analysis and a microbial assay were carried out to test the possible occurrence of cysteamine, β-alanine, and pantothenate in the enzyme. The results were negative, indicating the absence of pantetheine or a similar residue. The possible similarity in mechanism between flavanone synthase and 3-oxoacyl-(acyl carrier protein) synthase is discussed.

88 citations


Journal ArticleDOI
TL;DR: Results obtained with cell suspension cultures of parsley indicate that the activity of flavanone synthase is regulated differently from theActivity of phenylalanine ammonia-lyase, an enzyme frequently referred to as a key enzyme of flavonoid biosynthesis.

63 citations


Journal ArticleDOI
01 Jan 1979-Planta
TL;DR: The results allow the conclusion that chalcone is the first product of the flavanone synthase reaction in anthers of Petunia hybrida and that chAlcone isomerase is essential for the formation of flavonols and anthocyanins.
Abstract: The gene Po in pollen of Petunia hybrida Vilm. controls a discrete step in flavonoid biosynthesis. In recessive genotypes, naringenin-chalcone (4, 2′,4′,6′-tetrahydroxychalcone) is accumulated, whereas, under the influence of the wild-type allele flavonols and anthocyanins are formed. Enzymic investigations on anthers of four genetically defined lines with different pollen colouration revealed a clear correlation between accumulation of naringenin-chalcone and deficiency of chalcone isomerase (EC 5.5.1.6). The results allow the conclusion that chalcone is the first product of the flavanone synthase reaction in anthers of Petunia hybrida and that chalcone isomerase is essential for the formation of flavonols and anthocyanins. These results were similar to those previously obtained with Callistephus chinensis (L.) Nees.

42 citations


Journal ArticleDOI
TL;DR: Evidence is presented that flavanones and flavanone glycosides, following oral or parenteral administration, undergo glucuronylation and are selectively excreted via the bile.
Abstract: 1. The major biliary metabolites of flavanones in the rat have been identified by chromatographic and spectral methods.2. Evidence is presented that flavanones and flavanone glycosides, following oral or parenteral administration, undergo glucuronylation and are selectively excreted via the bile.3. Flavanone glycosides but not unconjugated aglycones may be excreted to a significant extent in bile.4. The percentage of parenterally administered flavanones excreted in bile varies inversely with the amount administered.

37 citations


Journal ArticleDOI
TL;DR: A new biflavanone has been isolated from the stem bark of Garcinia mannii (Guttiferae) and identified as I-3-II-3,3′-I-4′-II,4′ -I-5-2-5,I-7,II-7-nonahydroxy-I -3 -II-8-biflavalone.

32 citations


01 Jan 1979
TL;DR: This result supports the conclusions drawn from previous data that the two groups are regulated differentially and that the enzymes within each group are regulated in a coordinated manner.
Abstract: Several enzymes of phenylpropanoid metabolism showed large changes in their inducibility by light during the growth cycle of cell suspension cultures from parsley (Petroselinum hortense Hoffm.). Two of the three enzymes of general phenylpropanoid metabolism (group I) and six of the approximately 13 enzymes of the flavone and flavonol glycoside pathways (group II) were investigated. Both enzymes of group I (phenylalanine ammonia-lyase and 4-coumarate:coenzyme A ligase) were most effi'ciently induced at two different stages: first, soon after starting a new culture, and second, near the beginning of the stationary phase. In contrast, the enzymes of group II (acetyl-coenzyme A carboxylase, flavanone synthase, chalcone isomerase, UDP-apiose synthase, and at least one of two malonyltransferases) were maximally induced during exponential growth of the culture. This result supports the conclusions drawn from previous data that the two groups are regulated differentially and that the enzymes within each group are regulated in a coordinated manner.

28 citations



Journal ArticleDOI
TL;DR: The South American Chrysothamnus species afforded in addition to known compounds six new labdanetype acids, a bisabolene and a germacrene derivative as well as a new flavanone.

24 citations


Journal ArticleDOI
TL;DR: In this paper, two further Chromolaena species were investigated and two new cadinene derivatives and a related structure with a degraded Cadinene skeleton were elucidated by spectroscopic methods.

24 citations


Journal ArticleDOI
TL;DR: Seedlings of red cabbage germinated in the dark, rapidly produced anthocyanins upon illumination, and the activity of flavanone synthase, the first enzyme responsible for the establishment of C 15 flavonoid skeleton, paralleled that of the Anthocyanin concentration.

Journal ArticleDOI
TL;DR: In this paper, the occurrence and distribution of flavanone glycosides in the leaves and fruits of many kinds of artificial citrus hybrid plants were investigated by polyamide thin-layer chromatography.
Abstract: The occurrence and distribution of flavanone glycosides in the leaves and fruits of many kinds of artificial citrus hybrid plants were investigated by polyamide thin-layer chromatography. The citrus hybrids can be divided into two broad categories, a) those containing rutinosyl glycosides, b) those containing neohesperidosyl glycosides in accordance with the case of natural citrus species. The fiavonoid patterns of rutinosyl glycosides are classified into the following groups, a) hesperidin, b) narirutin, c) hesperidin and narirutin, d) didymin and narirutin, e) hesperidin, narirutin and eriocitrin and f) hesperidin and eriocitrin, while the pattern of neohesperidosyl glycosides fall into six groups, a) naringin, b) neohesperidin and naringin, c) neohesperidin, naringin and neoeriocitrin, d) neohesperidin and neoeriocitrin, e) naringin and neoeriocitrin, and f) poncirin, neohesperidin, naringin and neoeriocitrin. It is worthy of note that a hybrid (accession number 1088) between C. unshiu and C. hassaku c...



Journal ArticleDOI
TL;DR: The urinary metabolites of flavanone in the rate were investigated using a gas chromatographic mass spectrometric method employing an OV-1 capillary column and the most prominent of these were identified were flavan-4 alpha-ol and 6-hydroxyflavan-4 beta-ol.
Abstract: The urinary metabolites of flavanone in the rate were investigated using a gas chromatographic mass spectrometric method employing an OV-1 capillary column. Forty-three metabolites were detected and the most prominent of these were identified. The most common metabolic reactions were reduction of the keto group and hydroxylation at the 3- or 6-positions. Little hydroxylation occurred in ring B. The major metabolites were flavan-4 alpha-ol, trans-3-hydroxyflavan-4 beta-ol, 6-hydroxyflavanone and 6-hydroxyflavan-4 beta-ol. Gas chromatography analysis of underivatized flavanone metabolites, especially with stainless steel columns, results in the formation of dehydrated products including flavone, flav-3-ene and flavanone itself.

Journal ArticleDOI
TL;DR: In this paper, a flavanone glycoside isolated from Nicrembergia hippomania was characterized by spectroscopic methods as pinocembrin 7-neohesperidoside.

Journal ArticleDOI
TL;DR: In the presence of sodium sulphite in MeOH-H2O gave the flavanone dimers (2) and (3) in this article, respectively, in the case of MeOH and H2O.
Abstract: Irradiation of the flavones (1a) and (1b) in the presence of sodium sulphite in MeOH–H2O gave the flavanone dimers (2) and (3).



Journal ArticleDOI
TL;DR: Bromination of flavanone, 6-methylflavanone and 6-methyl-4-methoxyflavanone with pyridinium tribromide in glacial acetic acid gives the corresponding 3-bromoflavanones, which when refluxed with thiourea in ethanol undergo reduction to flavanones as mentioned in this paper.
Abstract: Bromination of flavanone, 6-methylflavanone, 6-methyl-4′-methoxyflavanone, and 6-methyl-3′,4′-dimethoxyflavanone with pyridinium tribromide in glacial acetic acid gives the corresponding 3-bromoflavanones, which when refluxed with thiourea in ethanol undergo reduction to flavanones.

Journal ArticleDOI
TL;DR: In this paper, a new method for synthesizing 3-Aminoflavenones was proposed, based on nucleophilic substitution in 3-Alkyl and 3-(Arylsulfonyloxy)-favanones.

Journal ArticleDOI
TL;DR: Eriodictyol-7-glucoside, a flavanone glycoside, was isolated as cream-white needles from the deep-blue fruit skins of Lasianthus japonica.
Abstract: Eriodictyol-7-glucoside, a flavanone glycoside, was isolated as cream-white needles from the deep-blue fruit skins of Lasianthus japonica, and in the same tissue eriodictyol and scopoletin were also found to occur in a small amount by means of paper chromatography.