Methoxyflavone Inhibitors of Cytochrome P450

Abstract  Cytochrome P450 enzymes are a superfamily of enzymes involved in the metabolism of endogenous compounds as well as xenobiotics. Due to the large number of reactions catalyzed by these enzymes and their importance in drug metabolism and carcinogenesis, they have been the focus of many studies over the years. Based on the knowledge that flavones are natural substrates of certain P450 enzymes (such as P450 1A2) involved in carcinogenesis, we have synthesized and studied a number of flavonoids as potential inhibitors of these enzymes. These compounds are structurally very similar to the natural flavone substrates of these enzymes but have methoxy substituents at various positions. Here we are reporting the synthesis, structural analysis, X-ray crystal structures, and preliminary inhibition studies of four methoxyflavones from this series. Crystallographic data: 2′-methoxyflavone, P-1, a = 7.2994(8) ?, b = 8.3322(7) ?, c = 10.8240(10) ?, α = 97.905(8)°, β = 92.779(10)°, γ = 111.105(8)°, V = 604.9(1) ?³; 3′-methoxyflavone, P2₁/n, a = 15.1313(16) ?, b = 3.9699(4) ?, c = 19.9454(16) ?, β = 91.673(8)°, V = 1197.6(2) ?³; 4′-methoxyflavone, P2₁/n, a = 16.451(12) ?, b = 3.881(1) ?, c = 19.529(16) ?, β = 106.65(1)°, V = 1195.1(4) ?³; 3′,4′-dimethoxyflavone, C2/c, a = 30.819(5) ?, b = 4.0857(7) ?, c = 26.100(3) ?, β = 124.21(1)°, V = 2717.6(7) ?³. Index Abstract  Methoxyflavone Inhibitors of Cytochrome P450 Michael McKendall, Tasha Smith, Kien Anh, Jamie Ellis, Terri McGee, Maryam Foroozesh, Naijue Zhu and Cheryl L. Klein Stevens* This paper is a report of the synthesis, structural analysis, X-ray crystal structures, and preliminary inhibition studies of 2′-methoxyflavone, 3′-methoxyflavone, 4′-methoxyflavone, and 3′,4′-dimethoxyflavone.

Isolation and structure determination of a new flavone glycoside from seed residues of seabuckthorn (Hippophae rhamnoides L.)

In this study, a valid method was established for the isolation and purification of flavone glycosides from Hippophae rhamnoides L. seed residues using high-speed counter-current chromatography in one step, with a solvent system of ethyl acetate-methanol-n-butyl alcohol-water (9:1:0.5:9, v/v/v/v). A total of 28.8 mg compound I and 57.3 mg compound II were obtained from 200 mg of flavone H-glycosides rich extract, with purities of 98.3 and 96.4%, respectively. The structures of two compounds were identified by MS and NMR. 3-O-β-D-Sophorosylkaempferol-7-O-{3-O-[2(E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoyl]}-α-L-rhamnoside is compound I and compound II named hippophanone is a new compound were identified by MS and NMR. The method was efficient and convenient, which could be used for the preparative separation of flavone glycosides from H. rhamnoides L. seed residues.     

Energetics of flavone and flavanone

In this work, we have determined the experimental standard (p° = 0.1 MPa) molar enthalpies of formation, in gas phase, of flavone and flavanone.These results were obtained by combining the standard molar enthalpies of formation in the condensed phase with the standard molar enthalpies of sublimation. The former values were derived from combustion experiments in oxygen, at T = 298.15 K, in a static bomb calorimeter. The values of the standard molar enthalpies of sublimation were obtained by Calvet microcalorimetry and corrected to T = 298.15 K.High-level density functional theory calculations using the B3LYP hybrid exchange–correlation energy functional with extended basis sets and more accurate correlated computational techniques of the MCCM/3 suite have been performed for the compounds.The obtained results, experimental and computational, for flavone and flavanone were compared with those obtained for chromone and chromanone, respectively.     

Isocassiaoccidentalin B,A New C‐Glycosyl Flavone Containing a 3‐Keto Sugar,and Other Constituents from Cassia nomame

A new C‐glycosyl flavone containing a 3‐keto sugar, isocassiaoccidentalin B ( 1 ), was isolated from whole Cassia nomame (Sieber ) Honda plants, along with eleven known compounds, including two flavonoids ( 2 and 3 ), five flavonoid glycosides ( 4  –  8 ), two chalcones ( 9 and 10 ), and two phenylpropanoids ( 11 and 12 ). The chemical structures of all compounds were determined via 1D‐ and 2D‐NMR, and ESI‐MS. Among these, compounds 2 , 3 , 7 , and 8 were found to be the most potent in inhibiting nitric oxide release. Compounds 1 , 2 , 4 , 8 , 9 , and 10 showed significant free‐radical scavenging activity.     

Two New Flavone Glucosides from Serratula strangulata

Genus Serratula（Compositae）consists of about 70 species distributed throughout theworld[1]．Serratula species have been used as folk medicine to treat chickenpox,toxicosis,high cholesterol in China[2]. The phytochemical study of plant S．strangulata has not beenreported so far．In the course of our searching for biologically active substances from thisplant,two new flavone glucosides（1,2）were isolated．The present paper covers the isolationand structural elucidation of the two new compounds．     

Crystal and molecular structure of 7-hydroxyflavone monohydrate, C14H10O3·H2O

The X-ray crystal structure of 7-hydroxyflavone monohydrate, C₁₄H₁₀O₃ · H₂O, is determined. The compound crystallizes in the monoclinic space group, P2₁/n with a = 3.801(3), b = 19.665(4), c = 16. 039(6), = 93.69(3)°, and = 0.68 mm^–1 for Z = 4. The phenyl ring of the flavone moiety is rotated 18.6(1)° out of the penzopyran plane, which is a typical value for flavones. In the crystal lattice, there are wide channels which are lined mainly by C–H groups. The water molecules enclosed in these channels are severely disordered.     

增强UV-B辐射、NaCl胁迫及其复合处理对小麦幼苗光合作用及黄酮代谢的影响

依据增强UV-B辐射、NaCl胁迫及其复合处理不同天数，分别测定各处理小麦幼苗第一片真叶的净光合速率、气孔导度、叶肉细胞间隙二氧化碳浓度、叶绿素含量、黄酮含量和苯丙氨酸裂解酶活性.发现NaCl胁迫和增强UV-B辐射均明显降低小麦幼苗的净光合速率、气孔导度和叶肉细胞间隙CO2浓度;和NaCl胁迫相较， NaCl+UV-B辐射对小麦幼苗上述指标无进一步降低效应.增强UV-B辐射、NaCl胁迫及其复合处理均促进苯丙氨酸裂解酶活性和黄酮含量提高.说明了增强UV-B辐射降低小麦幼苗净光合速率的主要原因是气孔限制，而NaCl胁迫减轻了增强UV-B辐射对小麦幼苗光合作用的降低效应.     

O-Heterocycles by the cyclization of side-chain bromomethoxylated 2′-acetoxychalcones

Summary The title chalcone derivatives react with aqueous sodium hydroxide of various concentrations to form aurones as the major product, together with small amounts of flavones. However, the introduction of 4-nitro or 4-chloro substituents resulted in the formation of flavones as the major product.

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O-Heterocyclen mittels Cyclisierung von an der Seitenkette brommethoxylierten 2-Acetoxychalconen

Zusammenfassung Die im Titel genannten Chalconderivate reagieren mit Natronlauge in verschiedenen Konzentrationen, wobei Aurone zusammen mit geringen Mengen an Flavonen entstehen. Die Einführung von 4-Nitro- oder 4-Chlor-Substituenten führte jedoch zur bevorzugten Bildung von Flavonen.

     

石香薷中两个新黄酮甙的研究

石香薷中两个新黄酮甙的研究郑尚珍，孙丽萍，沈序维王毅（西北师范大学化学系，兰州，７３００７０）（中国科学院兰州化学物理研究所）关键词石香薷，唇形科，黄酮甙唇形科植物石香薷（ＭＯｓｌａｃｈｉｎｅｎｓｉｓＭａｘｉｍ）作为中药，用来治疗暑湿感冒、头痛、腹痛...     

南雄银杏叶中银杏黄酮含量的H PLC测定

用高效液相色谱法测定在广东省南雄市不同采摘时间、不同树龄的银杏叶中总黄酮含量;采用Kromasil C18柱,流动相为V（甲醇）：V（4g/L磷酸水溶液）=55:45体系,检测波长254nm,外标法定量;结果表明南雄银杏叶中总黄酮平均含量为0.55%(w,干叶计）,每年6月为最佳摘叶时间。