- Biotransformation of chrysin and apigenin by Cunninghamella elegans
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Biotransformation of chrysin by Cunninghamella elegans NRRL 1392 produced apigenin, apigenin 7-sulfate, apigenin 7,4′-disulfate, and a new metabolite identified as chrysin 7-sulfate. On the other hand, fermentation of apigenin, using the same microorganism, yielded apigenin 7-sulfate and apigenin 7,4′-disulfate. The structures of the metabolites were established by spectral analysis, and acid and enzyme hydrolyses in addition to comparison with reference samples.
- Ibrahim, Abdel-Rahim Sayed
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- Regioselective ortho-Hydroxylations of Flavonoids by Yeast
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Natural flavonoids, such as naringenin, hesperetin, chrysin, apigenin, luteolin, quercetin, epicatechin, and biochanin A, were subjected to microbiological transformations by Rhodotorula glutinis. Yeast was able to regioselectively C-8 hydroxylate hesperetin, luteolin, and chrysin. Naringenin was transformed to 8- and 6-hydroxyderivatives. Quercetin, epicatechin, and biochanin A did not undergo biotransformation. A metabolic pathway for the degradation of chrysin has been elucidated. The metabolism of chrysin proceeds via an initial C-8 hydroxylation to norwogonin, followed by A-ring cleavage to 4-hydroxy-6-phenyl-2H-pyran-2-one.
- Sordon, Sandra,Madej, Anna,Pop?oński, Jaros?aw,Bartmańska, Agnieszka,Tronina, Tomasz,Brzezowska, Ewa,Juszczyk, Piotr,Huszcza, Ewa
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- New Flavonoid Glycoside from Thalictrum minus
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The new flavonoid diglycoside thamiflaside was isolated from the aerial part of Thalictrum minus. The chemical structure of this glycoside was determined as apigenin 7-O-α-L-2″′-methoxyrhamnopyranosyl-(1→6)-β-D-glucopyranoside based on PMR and 13/su
- Komilov,Agzamova,Isaev,Eshbakova
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- A new flavonoid glycoside from the leaf of Cephalotaxus koreana
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A new flavone glycoside, apigenin 5-O-α-l-rhamnopyranosyl-(1 → 3)-β-d-glucopyranoside (1), along with four known flavonol glycosides (2-5), were isolated from the leaf of Cephalotaxus koreana. The new glycoside 1 showed inhibitory activity in superoxide radical scavenging assay with IC50 value of 13.0 μM, while it showed weak activity in 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging assay. Compounds 2-5 exhibited antioxidant activity in scavenging DPPH and superoxide radicals with IC50 values ranging from 5.7 to 22.3 μM.
- Bae, KiHwan,Jin, WenYi,Thuong, Phuong Thien,Min, Byung Sun,Na, MinKyun,Lee, Young Mi,Kang, Sam Sik
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- Cloning of parsley flavone synthase I
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A cDNA encoding flavone synthase I was amplified by RT-PCR from leaflets of Petroselinum crispum cv. Italian Giant seedlings and functionally expressed in yeast cells. The identity of the recombinant, 2-oxoglutarate-dependent enzyme was verified in assays converting (2S)-naringenin to apigenin.
- Martens, Stefan,Forkmann, Gert,Matern, Ulrich,Lukacin, Richard
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- FLAVONOID GLYCOSIDES OF ARTEMISIA MONOSPERMA AND A. HERBA-ALBA
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Ten flavonoid glycosides were isolated and identified from Artemisia monosperma: vicenin-2, lucenin-2, acacetin 7-glucoside, acacetin 7-rutinoside, the 3-glucosides and 3-rutinosides of quercetin and patuletin, and the 5-glucosides of quercetin and isorhamnetin.From Artemisia herba-alba eight flavonoid glycosides were isolated and identified: isovitexin, vicenin-2, schaftoside, isoschaftoside and the 3-glucosides and 3-rutinosides of quercetin and patuletin.Key Word Index - Artemisia monosperma; A herba-alba; Compositae; flavone and flavonol glycosides.
- Saleh, Nabiel A. M.,El-Negoumy, Sabry I.,Abd-Alla, Mohamed F.,Abou-Zaid, Mamdouh M.,Dellamonica, G.,Chopin, J.
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- A NEW GLYCOSYLATED FLAVONOID, 7-O-α-L-RHAMNOPYRANOSYL-4'-O-RUTINOSYLAPIGENIN, IN THE EXUDATE FROM GERMINATING SEEDS OF Sesbania rostrata
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The title apigenin triglycoside was isolated (4 mg/6000 seeds) by reversephase column chromatography as the major u.v.-absorbing compound in the exudate of germinating seeds of Sesbania rostrata.The structure was assigned on the basis of u.v. spectra, f.a.b.-mass-spectral and 2D-n.m.r. data.The triglycoside was released continuously from the germinating seeds, but at a decreasing rate during the first two weeks.
- Messems, Eric,Montagu, Marc Van,Bruyn, Andre De,Jans, Arnold W. H.
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- COSMETIC COMPOSITION FOR SKIN IMPROVEMENT COMPRISING GREEN BARLEY EXTRACT
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Provided is a cosmetic composition for skin improvement including a green barley extract.
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- Extraction, Isolation and Characterization of Valuable Worked on Acacia Tortilis
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Acacia tortilis is one of the important species of genus Acacia belonging to family Leguminaceae. Though there is no more study performed on this plant but it plays important role in the countries where it found. These countries include North Africa, Arabian Peninsula and Asian countries. The various part of Acacia tortilis plant say leaves, pods, gum exudates and bark were used as antidiabetic, antidiarrhoeal, antiasthmatic and also had several other medicinal benefits. The present discussion deals with the isolation and characterization of the following compounds from the leaves of Acacia tortilis. Lupan-3-ol, 12,20-diene, Lupan-12, 20-dien 3-one, Friedelin, ?-amyrin, ?- sitosterol, Apigenin, Luteolin, Quercetin, 5,7-dihydroxy-4-p-methyl benzylisoflavone, Vitexin, 2',6'-dihydroxy chalcone-4'-O-glucoside.
- Muhaisen, Hasan M. H.
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p. 6731 - 6747
(2021/11/01)
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- 8-azacyclo-substituted chromone derivative as well as preparation method and pharmaceutical application thereof
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The invention discloses an 8-azacyclo-substituted chromone derivative as well as a preparation method and pharmaceutical application thereof, and belongs to the field of medicinal chemistry. The invention provides the 8-azacyclo-substituted chromone compound with selective PARP1/2 inhibitory activity, and the 8-azacyclo-substituted chromone compound can be used for preparing medicines for preventing or treating PARP1/2 defective tumors and has wide market application and development prospects.
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Paragraph 0131-0133
(2021/10/27)
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- Studies on Bignoniaceae: Newbouldiosides D-F, Minor Phenylethanoid Glycosides from Newbouldia laevis, and New Flavonoids from Markhamia zanzibarica and Spathodea campanulata
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Continued examination of the stem bark of Newbouldia laevis afforded three minor phenylethanoid glycosides, designated as newbouldiosides D-F. Their structures were elucidated by spectroscopic methods as β-(3,4-dihydroxyphenyl)ethyl 5-O-syringoyl-β-D-apiofuranosyloxy-(1 → 2)-O-[ α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-[ α-L-rhamnopyranosyl-(1 → 3)]-6-O-E-sinapoyl-β-D-glucopyranoside, and β-(3,4-dihydroxyphenyl)ethyl β-D-apiofuranosyloxy-(1 → 2)-O-α-L-rhamnopyranosyl-(1 → 2)-6-O-E-sinapoyl-β-D-glucopyranoside, respectively. These metabolites are the first members possessing a sinapoyl structural element. In addition, the series of naturally occurring flavonoids is extended by the identification of 3′,4′,5,7-tetrahydroxy-5′-methoxyflavanone and apigenin-5-O-α-L-rhamnopyranosyl-7-O-β-D-glucopyranoside obtained from leaf extracts of Markhamia zanzibarica and aromadendrin-7-O-(2″-O-formyl)-β-D-glucopyranoside isolated from Spathodea campanulata. The latter compound is the first example of a flavonoid possessing a formylated glucosyl moiety.
- Kolodziej, Herbert
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p. 989 - 997
(2020/11/18)
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- Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer
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Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.
- Long, Huan,Hu, Xiaolong,Wang, Baolin,Wang, Quan,Wang, Rong,Liu, Shumeng,Xiong, Fei,Jiang, Zhenzhou,Zhang, Xiao-Qi,Ye, Wen-Cai,Wang, Hao
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p. 12089 - 12108
(2021/09/06)
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- Continuous flow microchannel synthesis process of flavonoid compounds
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The invention provides a continuous flow microchannel synthesis process of flavonoid compounds. According to the process, hesperidin and iodine elementary substance are used as raw materials and react in a continuous flow microchannel reactor in the presence of a reaction solvent to synthesize the flavonoid compound as shown in a formula A. Compared with a traditional kettle-type preparation process, the process disclosed by the invention has the advantages that the preparation time is obviously shortened, and the conversion rate of raw materials and the yield of products are obviously improved; and especially, when the diosmin is prepared under optimal process conditions of continuous flow microchannel synthesis, the conversion rate of the raw material hesperidin is as high as 96.48%, and the yield of the product diosmin is as high as 81.96%. The continuous flow micro-channel synthesis process provided by the invention is beneficial to realizing safe, efficient and rapid industrial production of flavonoid compounds, and has a wide application prospect.
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Paragraph 0050-0060
(2021/06/22)
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- Preparation method of apigenin
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The invention provides a preparation method of apigenin. The preparation method comprises: adding naringenin into dimethylformamide, carrying out stirring dissolving, adding potassium iodide, heating,adding a mixed solution of an acidic compound and dimethyl sulfoxide, reacting, and standing to room temperature after the reaction is completed; adding an alkaline solution, carrying out a reaction,filtering after the reaction is completed, recovering the solvent from the filtrate under reduced pressure to obtain a black oily substance, adding a hydrochloric acid solution, performing a reflux reaction, and filtering to obtain a crude apigenin product; and adding dimethyl formamide, carrying out dissolving clarifying, filtering, recovering the solvent, adding ethanol, cooling, filtering, anddrying to obtain apigenin. According to the invention, the method is simple in process, rich in raw material supply, low in cost, high in product purity, qualified in product quality and suitable forlarge-scale industrial production; and trace potassium iodide is used as a catalyst, and acidic dimethyl sulfoxide is used as an oxidizing agent, so that the cost is low, the requirement of large-scale production is met, and the method is odorless, environment-friendly and pollution-free.
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Paragraph 0036; 0038-0057
(2020/04/22)
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- Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature
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Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.
- Tamuli, Kashyap J.,Sahoo, Ranjan K.,Bordoloi, Manobjyoti
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supporting information
p. 20956 - 20965
(2020/12/31)
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- New C,O-Glycosylflavones from the Genus Silene
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Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s
- Olennikov,Kashchenko
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p. 1026 - 1034
(2020/11/05)
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- Hepatoprotective, cytotoxic, antimicrobial and antioxidant activities of Dioon spinulosum leaves Dyer Ex Eichler and its isolated secondary metabolites
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Given the lack of adequate research on Dioon spinulosum (D. spinulosum) Dyer Ex Eichler, this study was conducted focusing on different biological activities and phytochemical investigation of D. spinulosum for the first time. D. spinulosum showed strong
- Abo El-Seoud, Kamilia A.,El-Aasr, Mona,Kabbash, Amal,Kassab, Amira A.,Negm, Walaa A.
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supporting information
p. 1 - 11
(2020/07/16)
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- Novel chromenone derivatives having substituted biphenyl group and a pharmaceutical composition for prevention or treatment of allergic diseases compring the same
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The present invention relates to: a novel chromenone derivative compound capable of effectively suppressing an allergic immune response by inhibiting signal transduction mediated by thymic stromal lymphopoietin (TSLP); and a pharmaceutical composition capable of fundamentally preventing or treating various allergic diseases by using the same.COPYRIGHT KIPO 2021
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Paragraph 0130-0137; 0139-0143
(2020/11/26)
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- Scope and Mechanism of the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with α,β-Unsaturated Carbonyl Compounds: Expedient Synthesis of Chromene and Benzoxacyclic Derivatives
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Chromene and benzoxacyclic derivatives were efficiently synthesized from the ruthenium-catalyzed dehydrative C-H coupling reaction of phenols with α,β-unsaturated carbonyl compounds. The cationic ruthenium-hydride complex was found to be an effective catalyst for the coupling and annulation of phenols with enals to form chromene products. The coupling of phenols with linear enones afforded 2,4-disubstituted chromene derivatives, whereas the analogous coupling with cyclic enones yielded 9-hydroxybenzoxazole products. The reaction of 3,5-dimethoxyphenol with PhCH=CHCDO resulted in the chromene product with a significant H/D exchange to both benzylic and vinyl positions. The most significant carbon isotope effect from the coupling of 3,5-dimethoxyphenol with 4-methoxycinnamaldehyde was observed on the α-olefinic carbon of the chromene product (C(2) = 1.067). A Hammett plot from the coupling of 3,5-dimethoxyphenol with para-substituted p-X-C6H4CH=CHCHO displayed a linear correlation, with a strong promotional effect by an electron-withdrawing group (ρ = +1.5; X = OCH3, CH3, H, F, Cl). Several biologically active chromenone derivatives were synthesized by using the catalytic coupling method. The catalytic method provides an expedient synthetic protocol for the coupling of phenols with α,β-unsaturated carbonyl compounds without employing reactive reagents or forming any wasteful byproducts.
- Mokar, Bhanudas Dattatray,Yi, Chae S.
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supporting information
p. 4625 - 4632
(2019/12/24)
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- Site-selective synthesis of acacetin and genkwanin through lipase-catalyzed deacetylation of apigenin 5,7-diacetate and subsequent methylation
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Candida antarctica lipase B-catalyzed deacetylation proceeded with high site-selectivity on the C-4′ acetyl group in apigenin triacetate to give apigenin 5,7-diacetate. Methylation of the liberated hydroxy group with the combination of trimethyloxonium tetrafluoroborate (Meerwein reagent) and 1,8-bis(dimethylamino)naphthalene (proton sponge) in CH2Cl2 proceeded in a quantitative manner to give the product methylated at the C-4′ hydroxy group (acacetin 5,7-diacetate). Even with the same precursor, a different methylation product at the C-7 hydroxy group (genkwanin 4′,5-diacetate) was obtained in 86% yield by applying iodomethane and Cs2CO3 in dimethyl sulfoxide (DMSO). The methylated products were deprotected to form acacetin and genkwanin. We inferred that the latter unexpected methylation was ascribable to the intermolecular migration of an acetyl group from C-7 to C-4′. DFT calculations indicated that the C-7 phenoxide ion was 12.6 kJ/mol more stable than the initially formed C-4′ phenoxide ion.
- Fujita, Rie,Hanaya, Kengo,Higashibayashi, Shuhei,Mandal, Susanta,Shoji, Mitsuru,Sugai, Takeshi
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p. 638 - 648
(2019/07/31)
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- Bioactivity-Guided Isolation and Identification of Antiadipogenic Compounds in Shiya Tea (Leaves of Adinandra nitida)
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Obesity is a worldwide epidemic contributing to a higher risk of developing maladies such as type 2 diabetes, heart disease, and cancer. Shiya tea (leaves of Adinandra nitida), a traditional Chinese tea, is widely consumed due to its palatable flavor and various curative effects, such as reducing blood pressure and blood lipids, as well as anti-inflammation, etc. However, no relevant research on the antiobesity effects of Shiya tea has been reported. In particular, no health-benefiting compounds, other than flavonoids, in Shiya tea have been reported. Thus, 3T3-L1 preadipocytes have been used as a bioactivity-guided identification model to verify the inhibitory effects of Shiya tea on adipogenesis, as well as to identify antiadipogenic compounds. Four triterpenoid saponins (1-4), including one new compound (2α,3α-dihydroxyursolic acid 28-O-β-d-glucopyranosyl ester, compound 1), and a flavonoid (5) have been identified using NMR (1D and 2D NMR) and liquid chromatography (LC)-MS techniques. Compound 1, the major antiadipogenic constituent with an IC50 value of 27.6 μg/mL, has been identified for the first time in Shiya tea. To understand the structure-activity relationship, three hydrolytic compounds (1s, 2s, and 5s) were obtained to provide an inhibitory effect on lipid accumulation during 3T3-L1 adipocyte differentiation. The inhibitory effect of the triterpenoid (1s) possessing no sugar group decreased significantly, while the flavonoid (5s) also without a sugar group showed increased activity. In addition, the hydroxyl group position may also play a role in inhibitory efficacy.
- Yuan, Chunmao,Huang, Linhua,Suh, Joon Hyuk,Wang, Yu
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- Oxidation of Flavone, 5-Hydroxyflavone, and 5,7-Dihydroxyflavone to Mono-, Di-, and Tri-Hydroxyflavones by Human Cytochrome P450 Enzymes
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Biologically active plant flavonoids, including 5,7-dihydroxyflavone (57diOHF, chrysin), 4′,5,7-trihydroxyflavone (4′57triOHF, apigenin), and 5,6,7-trihydroxyflavone (567triOHF, baicalein), have important pharmacological and toxicological significance, e.g., antiallergic, anti-inflammatory, antioxidative, antimicrobial, and antitumorgenic properties. In order to better understand the metabolism of these flavonoids in humans, we examined the oxidation of flavone, 5-hydroxyflavone (5OHF), and 57diOHF to various products by human cytochrome P450 (P450 or CYP) and liver microsomal enzymes. Individual human P450s and liver microsomes oxidized flavone to 6-hydroxyflavone, small amounts of 5OHF, and 11 other monohydroxylated products at different rates and also produced several dihydroxylated products (including 57diOHF and 7,8-dihydroxyflavone) from flavone. We also found that 5OHF was oxidized by several P450 enzymes and human liver microsomes to 57diOHF and further to 567triOHF, but the turnover rates in these reactions were low. Interestingly, both CYP1B1.1 and 1B1.3 converted 57diOHF to 567triOHF at turnover rates (on the basis of P450 contents) of >3.0 min-1, and CYP1A1 and 1A2 produced 567triOHF at rates of 0.51 and 0.72 min-1, respectively. CYP2A13 and 2A6 catalyzed the oxidation of 57diOHF to 4′57triOHF at rates of 0.7 and 0.1 min-1, respectively. Our present results show that different P450s have individual roles in oxidizing these phytochemical flavonoids and that these reactions may cause changes in their biological and toxicological properties in mammals.
- Nagayoshi, Haruna,Murayama, Norie,Kakimoto, Kensaku,Tsujino, Masaki,Takenaka, Shigeo,Katahira, Jun,Lim, Young-Ran,Kim, Donghak,Yamazaki, Hiroshi,Komori, Masayuki,Guengerich, F. Peter,Shimada, Tsutomu
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p. 1268 - 1280
(2019/05/07)
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- Identification of metabolites of liquiritin in rats by UHPLC-Q-TOF-MS/MS: Metabolic profiling and pathway comparison: In vitro and in vivo
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Liquiritin (LQ), the main bioactive constituent of licorice, is a common flavoring and sweetening agent in food products and has a wide range of pharmacological properties, including antidepressant-like, neuroprotective, anti-cancer and anti-inflammatory properties. This study investigated the metabolic pathways of LQ in vitro (rat liver microsomes) and in vivo (rat model) using ultra high-performance liquid chromatography coupled with hybrid triple quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF-MS/MS). Moreover, supplementary tools such as key product ions (KPIs) were employed to search for and identify compounds. As a result, 56 in vivo metabolites and 15 in vitro metabolites were structurally characterized. Oxidation, reduction, hydrolysis, methylation, acetylation, and sulfate and glucuronide conjugation were determined to be the major metabolic pathways of LQ, and there were differences in LQ metabolism in vitro and in vivo. In addition, the in vitro and in vivo metabolic pathways were compared in this study.
- Zhang, Xia,Liang, Caijuan,Yin, Jintuo,Sun, Yupeng,Zhang, Lantong
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p. 11813 - 11827
(2018/04/05)
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- Discovery of potent and selective acetylcholinesterase (AChE) inhibitors: acacetin 7-O-methyl ether Mannich base derivatives synthesised from easy access natural product naringin
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Naringin, as a component universal existing in the peel of some fruits or medicinal plants, was usually selected as?the material to synthesise bioactive derivates since it was easy to gain with low cost. In present investigation, eight new acacetin-7-O-methyl ether Mannich base derivatives (1–8) were synthesised from naringin. The bioactivity evaluation revealed that most of them exhibited moderate or potent acetylcholinesterase (AChE) inhibitory activity. Among them, compound 7 (IC50 for AChE?=?0.82?±?0.08?μmol?L?1, IC50 for BuChE?=?46.30?±?3.26?μmol?L?1) showed a potent activity and high selectivity compared with the positive control Rivastigmine (IC50 for AChE?=?10.54?±?0.86?μmol?L?1, IC50 for BuChE?=?0.26?±?0.08?μmol?L?1). The kinetic study suggested that compound 7 bind to AChE with mix-type inhibitory profile. Molecular docking study revealed that compound 7 could combine both catalytic active site (CAS) and peripheral active site (PAS) of AChE with four points (Trp84, Trp279, Tyr70 and Phe330), while it could bind with BuChE via only His 20.
- Liu, Hao-ran,Men, Xue,Gao, Xiao-hui,Liu, Lin-bo,Fan, Hao-qun,Xia, Xin-hua,Wang, Qiu-an
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p. 743 - 747
(2017/10/06)
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- A kind of coumarin substituted flavone derivatives and its preparation method and application (by machine translation)
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The invention relates to a flavonoid derivatives of coumarin substituted preparation and its use in medicine for diabetes, the application for the first time to synthesize the coumarin substituted flavonoid compounds, and for the first time on the α - glucosidase inhibitory activity evaluation, the results showed that the coumarin substituted flavonoid compound IC50 30 μm, are better than the acarbose inhibiting activity, found coumarin substituted flavone derivatives can very good inhibition α - glucosidase, at the same time the derivative synthesis, purification method which is simple, in medicine for treating diabetes in the development and application of and has broad prospects. (by machine translation)
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- An improved synthesis of apigenin and luteolin
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Apigenin and luteolin are the antioxidant flavonoids found in foods such as parsley, artichoke, basil and celery. Both of these compounds have shown the ability to protect cells against cancer and also to inhibit DNA oxidative damage. These flavonoids are part of many nutraceutical formulations available in the market. There is a need for the development of cost effective methodologies to produce them in large quantities. The synthetic process developed for both these compounds is general and can be applied for other flavonoids also. An industrially applicable high pure product, cost effective synthesis and general synthetic method has been developed and presented.
- Rambabu,Kumari,Baby Ramana,Ramani,Subbaraju,Hari Babu
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p. 1139 - 1143
(2016/03/01)
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- Preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis
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Disclosed is a preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis. The problems that flavonoid glycosides neither dissolve in water nor are hard to dissolve in a common organic alcohol solution, and flavone aglycone prepared from hydrolysis has slow hydrolysis speed, needs a large amount of an organic solvent, and cannot be totally hydrolyzed are solved. A complex product from complexation of aluminum salt and flavonoid glycosides is easy to dissolve in alcohol, hydrogen chloride generated by the complex product is utilized with addition of hydrochloric acid or sulfuric acid, and hydrolysis is carried out at a certain temperature to prepare aglycone or a mixture of aglycone and monoglycoside. After the reaction is over, phosphoric acid or phosphate is added to break complexation of aluminum ions and flavone to obtain flavone aglycone, or the mixture of flavone aglycone and flavone monoglycoside, or a mixture of flavone aglycone, flavone monoglycoside, and flavonoid glycoside. The method is simple and easy to operate, relatively high in yield and purity, and extremely low in cost, and is suitable for massive industrial production of flavone aglycone or the mixture of flavone aglycone and flavone monoglycoside.
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Paragraph 0018
(2016/10/31)
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- Antioxidant and myocardial preservation activities of natural phytochemicals from mung bean (Vigna radiata L.) seeds
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Mung bean (Vigna radiata L.) seeds (MBS) contain abundant nutrients with biological activities. This study was aimed to isolate key bioactive components from MBS with antioxidant and myocardial preservation activities. A new flavonoid C-glycoside, isovitexin-6″-O-α-l-glucoside, and 14 known compounds were obtained. Their structures were identified by extensive 1D and 2D NMR and FT-ICR-MS spectroscopic analyses. The antioxidant activities of these compounds were evaluated. Compounds 1-5 and 7-10 displayed 2,2′-azinobis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS?+) scavenging activity, but only 5 and 7 exhibited 2,2-diphenyl-1-picrylhydrazyl (DPPH?) scavenging activity. The myocardial preservation effect of 2, 3, and MBS were investigated by measuring the serum levels of LDH, CK, and AST as well as the tissue level of MDA and SOD. The results demonstrated that 2, 3, and MBS had a significant protective effect against ISO-induced myocardial ischemia. MBS can be regarded as a potential new source of antioxidants and myocardial preservation agents.
- Bai, Yan,Chang, Jiawei,Xu, Yan,Cheng, Dan,Liu, Hongxin,Zhao, Yunli,Yu, Zhiguo
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p. 4648 - 4655
(2016/07/06)
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- An improved synthesis of apigenin
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Two routes for the synthesis of the flavone apigenin are described. In the first, taxicatigenin was converted to 2-hydroxy-4,6- dimethoxyacetophenone and then by condensation with anisaldehyde to 2′-hydroxy-4,4′,6′-trimethoxychalcone. The latter was cyclised with iodine and demethylated with pyridine hydrochloride to form apigenin in 53% overall yield. In the second route, a single step for the preparation of the chalcone was used in which 1,3,5-trimethoxybenzene was acylated with p-methoxycinnamic acid. Although the synthesis of apigenin was achieved in a lower overall yield of 34%, the process was simpler.
- Wang, Qian,Cui, Wei,Liu, Man,Zhang, Ji,Liao, Rong-Qiang,Liao, Xia-Li,Yang, Jian
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- Total synthesis of (±)-Anastatins A and B
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Abstract Two novel flavones (±)-Anastatins A and B, each containing a benzofuran moiety, were synthesized for the first time by using bromination, Suzuki coupling reaction, and an oxidation/Oxa-Michael reaction cascade as the key steps. The syntheses of (±)-Anastatins A and B were achieved in eight steps from the commercially available phloroglucinol with 9% and 10% overall yield, respectively.
- Pan, Guojun,Ma, Yantao,Yang, Ke,Zhao, Xia,Yang, Hui,Yao, Qingwei,Lu, Kui,Zhu, Tao,Yu, Peng
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p. 4472 - 4475
(2015/06/30)
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- Semisynthesis of polymethoxyflavonoids from naringin and hesperidin
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Polymethoxyflavonoids (PMFs) possess important biological activities, notably as anticancer agents. Semisynthesis of a series of PMFs were performed by glycoside hydrolysis, dehydrogenation, bromination, aromatic nucleophilic substitution, O-methylation, dimethyldioxirane oxidation and regioselective demethylation, starting from abundant and inexpensive natural sources naringin and hesperidin. A new synthetic method for selective methylation using CuBr catalysed and microwave-assisted reaction was developed, and the dimethyl dioxirane oxidation of flavones to flavonols was much improved. The new semisynthetic route has the advantages of easy availability of starting materials, simple operation and good yields.
- Li, Yue,Cai, Shuanglian,He, Kailin,Wang, Qiuan
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p. 287 - 290
(2014/06/09)
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- The fungal leaf endophyte Paraconiothyrium variabile specifically metabolizes the host-plant metabolome for its own benefit
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Fungal endophytes live inside plant tissues and some have been found to provide benefits to their host. Nevertheless, their ecological impact is not adequately understood. Considering the fact that endophytes are continuously interacting with their hosts, it is conceivable that both partners have substantial influence on each other's metabolic processes. In this context, we have investigated the action of the endophytic fungus Paraconiothyrium variabile, isolated from the leaves of Cephalotaxus harringtonia, on the secondary metabolome of the host-plant. The alteration of the leaf compounds by the fungus was monitored through metabolomic approaches followed by structural characterization of the altered products. Out of more than a thousand molecules present in the crude extract of the plant leaf, we have observed a specific biotransformation of glycosylated flavonoids by the endophyte. In all cases it led to the production of the corresponding aglycone via deglycosylation. The deglycosylated flavonoids turned out to display significant beneficial effects on the hyphal growth of germinated spores. Our finding, along with the known allelopathic role of flavonoids, illustrates the chemical cooperation underlying the mutualistic relationship between the plant and the endophyte.
- Tian, Yuan,Amand, Séverine,Buisson, Didier,Kunz, Caroline,Hachette, Fran?ois,Dupont, Jo?lle,Nay, Bastien,Prado, Soizic
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- Antioxidant flavone glycosides and other constituents from Premna latifolia leaves
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A new flavone glycoside, apigenin 7-O-β-D-apiofuranosyl (1→2)-α-L-rhamnopyranoside 1 along with known compounds, apigenin 7-O-β-D-glucopyranoside-4'-acetate 2 and β-sitosterol-3-O-β-D- glucoside 3 have been isolated from the MeOH extract of the leaves of the medicinal plant, Premna latifolia Roxb (Verbenaceae). The structure of the new compound 1 has been elucidated on the basis of detailed spectral (including 2D-NMR) and chemical (including transformations into hexa and hepta acetates) studies. The notations of sugars in 1 have been assigned on GC analysis of their TMS derivatives. The isolation of compound 2 is being reported for the first time from a higher plant. Both flavones 1 and 2 exhibit significant DPPH radical scavenging activity with IC50 value of 16.0 and 22.5 μg/mL, respectively, which is comparable to that of standard antioxidant, BHT (IC 50 of 17.5 ug/mL). Hence, the MeOH extract of the leaves of this plant may be useful as a potential source of natural antioxidant.
- Ghosh, Partha Sarathi,Das, Niranjan,Dinda, Biswanath
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p. 746 - 749
(2014/07/07)
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- A new synthesis for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones by modified Baker-Venkataraman transformation
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Baker-Venkataraman (BV) rearrangement is the method of choice for the synthesis of flavones. The major limitation of BV is that it requires extensive protections and deprotections of hydroxyl groups which make the process lengthy and cumbersome. In the present study, a three step efficient method has been developed using simple protecting groups and easily available starting materials. New syntheses for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones are described.
- Pandurangan
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p. 225 - 229
(2014/05/20)
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- Production of hydroxlated flavonoids with cytochrome P450 BM3 variant F87V and their antioxidative activities
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A variant of P450 BM3 with an F87V substitution [P450 BM3 (F87V)] is a substrate-promiscuous cytochrome P450 monooxygenase. We investigated the bioconversion of various flavonoids (favanones, chalcone, and isoflavone) by using recombinant Escherichia coli cells, which expressed the gene coding for P450 BM3 (F87V), to give their corresponding hydroxylated products. Potent antioxidative activities were observed in some of the products.
- Kitamura, Emi,Otomatsu, Toshihiko,Maeda, Chiemi,Aoki, Yoko,Ota, Chihiro,Misawa, Norihiko,Shindo, Kazutoshi
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p. 1340 - 1343
(2013/07/26)
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- Total synthesis of apigenin
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An efficient method for the synthesis of apigenin (4',5,7- trihydroxyflavone, a traditional medicine) from phloroglucinol and anisaldehyde has been developed. This transformation features a green method for hydroxyl protection as methyl ethers and a different way for cyclisation using iodine in DMSO. The overall yield of 40% is satisfactory.
- Wang, Jin,Zhou, Rong-Guang,Wu, Ting,Yang, Tao,Qin, Qi-Xue,Li, Li,Yang, Bo,Yang, Jian
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p. 121 - 122
(2012/09/21)
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- Hydrolysis of flavonoid glycosides by propolis β-glycosidase
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Flavonoids generally occur as O-glycosides with sugars bound in nature, while aglycones and their derivatives are the main flavonoids in propolis. The objective of this work was to study the propolis β-glycosidase activities toward flavonoid β-glycosides and their conjugated forms. β-Glycosidase was extracted from propolis, incubated with avonoid glycosides, and analysed for aglycone formation by HPLC. The results demonstrated that glucose conjugates were rapidly hydrolysed, but not conjugates with other sugars, i.e. rutin and naringin. The rate and extent of deglycosylation depends on the structure of the avonoid and the position of the sugar substituitions. Quercetin 3-O-glucoside had the highest percent of hydrolysis, while quercetin 7-O-glucoside was the least hydrolysed. The Km values for hydrolysis of apigenin 7-glucoside and luteolin-7-O-glucoside were 13M and 20M, respectively.
- Zhang, Cui-Ping,Liu, Gang,Hu, Fu-Liang
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scheme or table
p. 270 - 273
(2012/03/27)
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- Polar constituents of Ligustrum vulgare L. and their effect on lipoxygenase activity
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The present work summarizes results of isolation and identification of polar constituents of the methanolic extract of Ligustrum vulgare L. leaves and of the evaluation of inhibiting activity of selected isolates on rat lung cytosol fraction lipoxygenase. Six different compounds were isolated from the ethylacetate and butanol portions of the methanolic extract (hydroxytyrosol and its glucoside, ligustroflavon, oleuropein, acteoside, echinacoside). The inhibitory activity of oleuropein, echinacoside and the water infusion of Ligustrum vulgare leaves tested on LOX was expressed as IC50. Kinetic parameters (K M, V max) and type of inhibition were determined. As the most effective in competitive inhibition of LOX, oleuropein was proved.
- Mucaji, Pavel,Nagy, Milan,Zahradnikova, Anna,Holkova, Ivana,Bezakova, Lydia,Svajdlenka, Emil,Liptaj, Tibor,Pronayova, Nadezda
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experimental part
p. 367 - 372
(2012/03/08)
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- THERAPEUTIC COMPOUNDS FOR BLOCKING DNA SYNTHESIS OF POX VIRUSES
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This invention provides methods of inhibiting replication of a poxvirus by contacting a poxvirus with a compound having formula I, formula XXI, formula XXXII, or formula XLI which in turn reduce, inhibit, or abrogate poxvirus DNA polymerase activity and/or its interaction with its processivity factor. Formula I, formula XXI, formula XXXII, or formula XLI can be utilized to treat humans and animals suffering from a poxvirus infection. Pharmaceutical compositions for treating poxvirus infected subjects are also provided.
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- Composition for Topical Use
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The use, as a dermatological or cosmetic medicament, of compounds capable of transiently interacting with the AhR receptor (aryl hydrocarbon receptor) as agents for modulating skin functions such as sebaceous function, skin healing, skin atrophy termed “dermatoporosis”, estrogen deprivation and defense against infection, without inducing other toxic effects of the TCDD type. The compounds that interact with the AhR receptor are chosen in that they have a metabolism favorable to the dissociation of these effects, in particular by virtue of in situ production from a precursor and/or metabolization modulated in situ.
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- Flavone synthase II (CYP93B16) from soybean (Glycine max L.)
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Flavonoids are a very diverse group of plant secondary metabolites with a wide array of activities in plants, as well as in nutrition and health. All flavonoids are derived from a limited number of flavanone intermediates, which serve as substrates for a variety of enzyme activities, enabling the generation of diversity in flavonoid structures. Flavonoids can be characteristic metabolites, like isoflavonoids for legumes. Others, like flavones, occur in nearly all plants. Interestingly, there exist two fundamentally different enzymatic systems able to directly generate flavones from flavanones, flavone synthase (FNS) I and II. We describe an inducible flavone synthase activity from soybean (Glycine max) cell cultures, generating 7,4′-dihydroxyflavone (DHF), which we classified as FNS II. The corresponding full-length cDNA (CYP93B16) was isolated using known FNS II sequences from other plants. Functional expression in yeast allowed the detailed biochemical characterization of the catalytic activity of FNS II. A direct conversion of flavanones such as liquiritigenin, naringenin, and eriodictyol into the corresponding flavones DHF, apigenin and luteolin, respectively, was demonstrated. The enzymatic reaction of FNS II was stereoselective, favouring the (S)- over the (R)-enantiomer. Phylogenetic analyses of the subfamily of plant CYP93B enzymes indicate the evolution of a gene encoding a flavone synthase which originally catalyzed the direct conversion of flavanones into flavones, via early gene duplication into a less efficient enzyme with an altered catalytic mechanism. Ultimately, this allowed the evolution of the legume-specific isoflavonoid synthase activity.
- Fliegmann, Judith,Furtw?ngler, Katarina,Malterer, Georg,Cantarello, Corrado,Schüler, G?de,Ebel, Jürgen,Mith?fer, Axel
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experimental part
p. 508 - 514
(2010/06/17)
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- C-Glucosylflavonoid biosynthesis from 2-hydroxynaringenin by Desmodium uncinatum (Jacq.) (Fabaceae)
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[2′,3′,5′,6′-2H4]-2-Hydroxynaringenin is synthesised and incubated with commercially available UDP-glucose and the crude protein extract from Desmoduim uncinatum leaves. The organic extract produces isotopically labelled [2′,3′,5′,6′-2H4]-vitexin and [2′,3′,5′,6′-2H4]-isovitexin. Repeating the experiment with denatured protein or replacing the 2-hydroxynaringenin with [2′,3′,5′,6′-2H4]-apigenin or [2′,3′,5′,6′-2H4]-naringenin results in no observable incorporation. 2-Hydroxynaringenin is therefore the substrate for C-glucosylflavonoid biosynthesis in D. uncinatum.
- Hamilton, Mary L.,Caulfield, John C.,Pickett, John A.,Hooper, Antony M.
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scheme or table
p. 5656 - 5659
(2011/02/24)
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- Urease inhibitiory flavone glucosides from Marrubium anisodon
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Compounds 1-3, new flavonoid glucosides have been isolated from the ethyl acetate soluble fractions of Marrubium anisodon, along with apigenin 4′-0-β-D-glucopyranoside 4, kaempferol 3-0-β-D-glucopyranoside 5 and β-sitosterol 3-0-β-D-glucopyranoside 6, respectively. Their structures were assigned from 1H- and 13C-NMR spectra, DEPT and by COSY, HMQC, NOESY and HMBC experiments. Compounds 1-5 showed significant inhibitory activity against the enzyme urease.
- Hussain,Perveen,Malik,Afza,Iqbal,Tareen
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experimental part
p. 1329 - 1335
(2010/08/05)
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- New flavonoid glycosides from Elsholtzia rugulosa Hemsl.
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Elsholtzia rugulosa Hemsl. is known in China as a local herbal tea, medicinal herb and honey plant. Chemical examination of E. rugulosa led to the isolation of two new flavonoid glycosides, apigenin 4'-O-α-D- glucopyranoside (1) and 5,7,3',4'-tetrahydroxy
- She, Gaimei,Guo, Zhiqin,Lv, Haining,She, Dongmei
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experimental part
p. 4190 - 4196
(2009/12/26)
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- Microbial metabolism part 9.1 Structure and antioxidant significance of the metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones
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5,7-Dihydroxyflavone (chrysin) (1) when fermented with fungal cultures, Aspergillus alliaceous (ATCC 10060), Beauveria bassiana (ATCC 13144) and Absidia glauco (ATCC 22752) gave mainly 4′-hydroxychrysin (4), chrysin 7-O-β-D-4-O-methylglucopyranoside (5) and chrysin 7-sulfate (6), respectively. Mucore ramannianus (ATCC 9628), however, transformed chrysin into six metabolites: 4′-hydroxy-3′-methoxychrysin (chrysoeriol) (7), 4′-hydroxychrysin (apigenin) (4) 3′,4′-dihydroxychrysin (luteolin) (8), 3′-methoxychrysin 4′-O-α-D-6- deoxyallopyranoside (9), chrysin 4′-O-α-D-6-deoxyallopyranoside (10), and luteolin 3′-sulfate (11). Cultures of A. alliaceous (ATCC 10060) and B. bassiana (ATCC 13144) metabolized 5-hydroxyflavone (2) into 5,4′-dihydroxyflavone (12) and 4′-hydroxyflavone 5-O-β-D-4-O-methylglucopyranoside (13), respectively. 6-Hydroxyflavone (3) was transformed into 6-hydroxyflavanone (14), flavone 3-O-β-D-4-O- methylglucopyranoside (15) and (±)-flavanone 6-O-β-D-4-O- methylglucopyranoside (16) by cultures of Beauveria bassiana (ATCC 13144). The structures of the metabolic products were elucidated by means of spectroscopic data. The significance of the metabolites as antioxidants in relation to their structure is briefly discussed.
- Herath, Wimal,Mikell, Julie Rakel,Hale, Amber Lynn,Ferreira, Daneel,Khan, Ikhlas Ahmad
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experimental part
p. 418 - 422
(2009/04/11)
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- Reactions of carbanions with 1,3-benzodioxin-4-ones: Facile routes to flavones, aurones, and acyl phloroglucinols
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Two 1,3-benzodioxin-4-ones react with enolates, acetylides and aryllithium reagents to afford adducts that were converted into flavones, aurones, and an acyl phloroglucinol. Georg Thieme Verlag Stuttgart.
- Kraus, George A.,Wie, Jingqiang,Thite, Aniket
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experimental part
p. 2427 - 2431
(2009/04/06)
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- Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones
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Flavonoids are constituents of the human diet (they are present in many beverages and food), and in organisms they are responsible for several biological functions, including that of antioxidant. Because of the increasing interest in these molecules, methods for their synthesis and structural modification are of great importance; studies on the biological activities of many of these compounds are insufficient because of their scarcity and/or high cost. We have developed an expeditious synthesis of polyoxygenated flavones, starting from available and inexpensive flavanones, using a bromination- methoxylation procedure. A series of flavonoids that are not otherwise accessible can be prepared using this method. As an example, 3′-demethoxysudachitin, a limited flavone possessing antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori and acting as a 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenger, was prepared in fairly satisfactory yield.
- Bovicelli, Paolo,D'Angelo, Vittoria,Collalto, Daniela,Verzina, Antonio,D'Antona, Nicola,Lambusta, Daniela
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p. 1697 - 1701
(2008/03/11)
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