- Enzyme-polysaccharide interaction and its influence on enzyme activity and stability
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An attempt was made to probe and elucidate the influence of three kinds of polysaccharides including the negatively charged sodium carboxymethyl cellulose (CMC), the uncharged methyl cellulose (MC) and the positively charged sodium carboxymethyl chitosan (CMCS), on the catalytic activity and stability of the model enzyme, β-d-glucuronidase (GUS). DSC analysis showed that the denaturing temperature of GUS was increased by 7 °C in the presence of CMC, but decreased in the presence of MC or CMCS by 5 and 3 °C, respectively. This variation was in good accordance with changes in the enzyme's catalytic activity. Circular dichroism was employed to characterize the conformational changes of GUS before and after the addition of the polysaccharide. It suggested that charged polysaccharides, CMC and CMCS, were favorable for improving the pH stability and the storage stability of GUS, whereas uncharged MC did not show such a stabilizing effect. At an elevated temperature up to 70 °C, GUS in CMC solution remained 78% activity and displayed the highest thermal stability among the three enzyme-polysaccharide pairs. The electrostatic interaction between enzyme and polysaccharides was closely relevant to the enzyme conformation, activity and stability.
- Li, Jian,Jiang, Zhongyi,Wu, Hong,Liang, Yanpeng,Zhang, Yufei,Liu, Jiaxian
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Read Online
- ADDITIONAL FLAVONOIDS FROM ELICITOR-TREATED CELL CULTURES OF CEPHALOCEREUS SENILIS
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Five major flavonoids induced by chitin in Cephalocereus senilis cell suspension cultures have been reported previously.We describe here five minor induced flavonoids including two new and three known ones.The two new compounds are (2S)-5,6,7-trihydroxyflavanone 7-glycoside and baicalein 7-(6''-malonylglucoside).
- Liu, Qin,Dixon, Richard A.,Mabry, Tom J.
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Read Online
- Investigation on the inclusion behaviour of baicalein with β-cyclodextrin and derivatives and their antioxidant ability study
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The formation of the complexes of baicalein (Ba) with β-cyclodextrin (β-CD) and β-CD derivatives (HP-β-CD and Me-β- CD) was studied by UV-vis absorption spectroscopy, fluorescence method, nuclear magnetic resonance spectroscopy and phase-solubility measurement. The solid-inclusion complexes of Ba with CDs were synthesised by the co-precipitation method. The characterisations of the solid-inclusion complexes have been proved by infrared spectra and differential scanning calorimetry. Experimental conditions including the concentration of various CDs and media acidity were investigated in detail. The results suggested that the inclusion ratio of HP-β-CD with Ba was the highest among the three kinds of CDs. The binding constants (Ks) of the inclusion complexes were determined by fluorescence method and phasesolubility measurement. Kinetic studies of DPPHz with Ba and CDs complexes were also done. The results indicated that the Ba/HP-β-CD complex was the most reactive form.
- Chao, Jianbin,Su, Jian,Li, Jinxia,Zhao, Wei,Huang, Shuping,Du, Rui
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Read Online
- Biotransformation of Chrysin to Baicalein: Selective C6-Hydroxylation of 5,7-Dihydroxyflavone Using Whole Yeast Cells Stably Expressing Human CYP1A1 Enzyme
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Naturally occurring polyphenolic compounds are of medicinal importance because of their unique antioxidant, anticancer, and chemopreventive properties. Baicalein, a naturally occurring polyhydroxy flavonoid possessing a diverse range of pharmacological activities, has been used in traditional medicines for treatment of various ailments. Apart from its isolation from natural sources, its synthesis has been reported via multistep chemical approaches. Here, we report a preparative-scale biotransformation, using whole yeast cells stably expressing human cytochrome P450 1A1 (CYP1A1) enzyme that allows regioselective C6-hydroxylation of 5,7-dihydroxyflavone (chrysin) to form 5,6,7-trihydroxyflavone (baicalein). Molecular modeling reveals why chrysin undergoes such specific hydroxylation mediated by CYP1A1. More than 92% reaction completion was obtained using a shake-flask based process that mimics fed-batch fermentation. Such highly efficient selective hydroxylation, using recombinant yeast cells, has not been reported earlier. Similar CYP-expressing yeast cell based systems are likely to have wider applications in the syntheses of medicinally important polyphenolic compounds.
- Williams, Ibidapo S.,Chib, Shifali,Nuthakki, Vijay K.,Gatchie, Linda,Joshi, Prashant,Narkhede, Niteen A.,Vishwakarma, Ram A.,Bharate, Sandip B.,Saran, Saurabh,Chaudhuri, Bhabatosh
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Read Online
- 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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- Flavonoid derivative as well as preparation method and identification method thereof
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The invention discloses a flavonoid derivative, which has structure formulas shown as a general formula (I) and a general formula (II) as in the description, wherein R1 is alkyl or cyclo alkane; R2 isalkyl or cyclo alkane; R1, R2 and nitrogen atoms form cycloaliphatic ring or heterocycle; R3 is alkyl or aryl or aralkyl; the value of n is 1 to 10. The invention also discloses a preparation methodand an identification method of the flavonoid derivative.
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Paragraph 0078; 0079; 0080; 0088; 0100; 0110; 0120; 0129
(2019/02/17)
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- Anti-angiogenic and anticancer effects of baicalein derivatives based on transgenic zebrafish model
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Angiogenesis leads to tumor neovascularization by promoting tumor growth and metastatic spread, therefore, angiogenesis is considered as an attractive target for potential small molecule anticancer drug discovery. Herein, we report the structural modification and biological evaluation of baicalein derivatives, among which compound 42 had potent in vivo anti-angiogenic activity and wide security treatment window in transgenic zebrafish model. Further, 42 exhibited the most potent inhibitory activity on HUVEC proliferation, migration and tube formation in vitro. Moreover, 42 significantly inhibited growth of human lung cancer A549 cells and weak influence on human normal fibroblast L929 cells. The present research demonstrated that the significant anti-angiogenic and anticancer effects, which provided the supportive evidence for 42 could be used as a potential compound of cancer therapy.
- Jiang, Xueyang,Zhou, Junting,Lin, Qinghua,Gong, Guiyi,Sun, Haopeng,Liu, Wenyuan,Guo, Qinglong,Feng, Feng,Qu, Wei
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supporting information
p. 4481 - 4492
(2018/08/11)
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- Synthesis of oroxylin A starting from naturally abundant baicalin
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– A new approach to oroxylin A, a monomethylated trihydroxyflavone, is described. The starting material was baicalin, a representative naturally abundant flavonoid glucuronide. First, conditions for the cleavage of the glycosidic bond were established, using a mixture of water and conc. sulfuric acid (5:2) at 121 °C for 40 min. The hydrolysis was performed in a high-pressure steam sterilizer so that the temperature and reaction time were precisely controlled. Subsequent acetylation of the crude material furnished baicalein 6,7-diacetate on a preparative scale and in a reproducible manner. Next, the C-7 position was protected site-selectively with a methoxymethyl (MOM) group, taking advantage of an unexpected sequential migration of the two acetyl groups among the C-5, C-6, and C-7 positions under basic conditions. The removal of the two remaining acetyl groups followed by site-selective methylation of the C-6 position furnished 5-hydroxy-6-methoxy-7-methoxymethoxyflavone (oroxylin A C-7 MOM ether). Finally, by the deprotection of the MOM ether, oroxylin A was obtained in 6 total steps and 62% overall yield from baicalin.
- Fujita, Rie,Hanaya, Kengo,Higashibayashi, Shuhei,Sugai, Takeshi
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p. 1165 - 1174
(2019/07/31)
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- An efficient, scalable approach to hydrolyze flavonoid glucuronides via activation of glycoside bond
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Hydrolyzing flavonoid glucuronides into corresponding aglycones posed some significant challenges. To improve acid-catalyzed hydrolysis process of flavonoid glucuronide, structures of glucuronide, hydrolysis parameters and post-processing were optimized. The optimized condition was performed by hydrolysis flavonoid glycoside methyl ester in a mixed solvent consisting of 2?mol/L H2SO4/EtOH/H2O (1/8/1, v/v/v) at 95?°C for 7?h and resulted in up to 90% aglycone yields, minimal byproduct formations and milder hydrolysis conditions. Furthermore, the optimized method avoids tedious purification steps and is easily conducted on a relatively large-scale using economical and commercially available reagents.
- Jiang, Xue-Yang,Li, Xin-Chen,Liu, Wen-Yuan,Xu, Yun-Hui,Feng, Feng,Qu, Wei
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p. 1895 - 1903
(2017/03/11)
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- The invention relates to a raw material for preparing the glucuronic acid the glucoside is corresponding aglycone (by machine translation)
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The invention discloses a glucuronic acid the glucoside is raw material for preparing the corresponding aglycone method, comprises the following steps: (1), synthesis of methyl chlorine sulfurous acid; (2), glucuronic acid methyl ester glucoside synthesis; (3), the inorganic acid is added in the ethanol, into inorganic acid ethanol solution, and then the inorganic acid ethanol solution is added to step (2) is made in the product of the glucuronic acid methyl ester glucoside, acid hydrolysis; (4), after the reaction, the reaction is cooled down to the room temperature after the, in the reaction liquid is poured into the water, standing precipitate, precipitation after complete filtering, the resulting solid for recrystallization dilute alcohol, obtaining the corresponding aglycone pure product. The method of the invention essentially solves the problem of the glucuronic acid the glucoside is difficult hydrolysis, the process is simple, short reaction time, does not need to use a large amount of organic solvent, after treatment is simple, the resulting aglycone yield is as high as 90%, purity as high as 99%, low cost, can be used for large-scale industrial production. (by machine translation)
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Paragraph 0039; 0040; 0044; 0045; 0049; 0050; 0051-0053
(2017/09/23)
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- Macroporous resin auxiliary various glycoside hydrolysis to prepare their aglycon, secondary glucoside method
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Various glycoside compounds and particularly glycoside compounds which are unstable, easy to oxidize and difficult to dissolve in water and an organic solvent are hydrolyzed under the actions of adsorption, dispersion, curing and settlement of macroporous adsorption resin to generate aglycone or a mixture of the aglycone and secondary glucoside, and the macroporous adsorption resin is secondarily eluted or primarily eluted by using an organic solvent to obtain aglycone, secondary glucoside and a mixture of the aglycone and the secondary glucoside. The invention provides a universal method for preparing the aglycone and the secondary glucoside by using the various glycoside compounds, the method is simple in operation, almost integrated in hydrolysis and separation, high in product purity, good in product yield, free of expensive reagent, capable of realizing repeated utilization of hydrolysate and the macroporous adsorption resin, environment-friendly, easy for realizing industrial production and low in cost and has great advantages as comparison with an enzyme hydrolysis method, a fermentation method and the like. By taking the hydrolysis of the total saponin of panax ginseng as an example, through the hydrolysis of acetic acid and other acids, more prosapogenins Rh2 of panax ginseng and protopanaxadiol aglycones are obtained, but a C17 side chain cyclization product is not obvious.
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Paragraph 0044; 0045
(2017/08/23)
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- Method for preparing baicalein
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The invention discloses a method for preparing baicalein. According to the method, 2,6-dimethoxy-p-benzoquinone used as an initial raw material is subjected to reduction, Friedel-Crafts acetylation, claisen condensation, dehydrogenation oxidation cyclization and demethylation five reactions to obtain baicalein with high yield. The method uses low-price and easily-available initial raw material, reagent and the like, has few synthesizing steps, is easy and convenient to operate and easy for production control, has high product yield and high purity, and is suitable for large-scale preparation and production application of baicalein.
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- Method for preparing baicalein
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The invention relates to a method for preparing anti-virus and anti-bacterial inflammatory medicine baicalein. According to the method, phenol serves as a starting material, and a key chalcone intermediate is prepared through bromination, methoxy substitution, Friedel-crafts acylation and aldol condensation; the key intermediate is subjected to oxidative cyclisation and methyl removal reaction, and high-purity baicalein can be prepared. According to the new method, adopted raw reagents are cheap and easy to obtain, the number of synthesis steps is small, reaction operation is easy and convenient, production control is easy, the product yield is high, purity is good, and the method is suitable for production and application of baicalein.
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Paragraph 007; 008; 0035
(2016/10/09)
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- Pharmacophore and docking-based hierarchical virtual screening for the designing of aldose reductase inhibitors: Synthesis and biological evaluation
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A set of 54 studied flavonoid inhibitors of aldose reductase (ALR2) enzyme has been utilized for pharmacophore modeling and 3D-QSAR analysis using "PHASE" program of Schr?dinger software. The generated pharmacophore model (AADRR.1109) was challenged to screen "PHASE" database to identify new ALR2 inhibitors. The retrieved hits were employed for docking analysis and pharmacokinetic parameter calculation to obtain orally active molecules. To predict the activity of final retrieved hits, 3D-QSAR model was developed, and the best model was selected on the basis of various statistical parameters (Rtrain 2 0.719; Q test 2 0.647 and SD 0.663). Totally five screened molecules which showed better enhanced predicted activity were synthesized and evaluated for in vitro ALR2 inhibitory activity. All tested molecules showed ALR2 inhibitory activity (IC50) below 40 μM. Additionally, the free radical scavenging potential of synthesized molecules was also determined which played a useful role to control the progression of diabetic complications. All molecules showed good antioxidant potential, thus the designed molecules, in future, could be explored to ameliorate the development of diabetic complications.
- Vyas, Bhawna,Singh, Manjinder,Kaur, Maninder,Silakari, Om,Bahia, Malkeet Singh,Singh, Baldev
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p. 609 - 626
(2016/03/08)
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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 0015
(2016/10/31)
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- A method for preparation of baicalin scutelloside (by machine translation)
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The present invention provides a method for preparation of baicalin scutelloside, melt solvent with low total is the hydrolysis medium, enzymatic hydrolysis new method for preparation of baicalin scutelloside. The advantage of this invention lies in the volatility is low, safe and non-toxic green solvent--low altogether melt solvent as the aqueous hydrolysis medium, to overcome the problem of the prior art the destruction of the role scutelloside large, low conversion rate, serious pollution, disadvantages such as being complicated to separate the purification process. The preparation method is simple and easy to operate, safe environmental protection, using the content of baicalin is 80% grain preparation of raw material, scutelloside conversion rate can be up to 90% or more, of baicalin purity can be up to 75% or more. (by machine translation)
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Paragraph 0040
(2016/12/12)
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- COMPOSITION AND METHOD FOR TREATING OR PREVENTING INFLUENZA VIRUS INFECTION
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The present invention provides a pharmaceutical composition and method for treating or preventing influenza virus infection in a subject comprising administering the subject with a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of compounds provided in this invention. In addition, the prevent invention provides new compounds for treating or preventing influenza virus infection.
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Paragraph 0055
(2015/12/23)
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- Synthesis and anti-influenza activities of novel baicalein analogs
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A series of novel flavones derivatives were synthesized based on modification of the active ingredients of a traditional Chinese medicine Scutellaria baicalensis GEORGI and screened for anti-influenza activity. The synthetic baicalein (flavone) analogs, especially with the B-rings substituted with bromine atoms, were much more potent than oseltamivir or ribavirin against H1N1 Tamiflu-resistant (H1N1 TR) virus and usually with more favorable selectivity. The most promising were 5b, 5c, 6b and 6c, all displaying an 50% effective concentration (EC50) at around 4.0-4.5 μM, and a selective index (SI=50% cytotoxic concentration (CC50)/EC 50)>70. For seasonal H3N2-infected influenza virus, both 5a and 5b with SI >17.3 indicated superior to ribavirin. The flavonoids having both not-naturally-occurring bromo-substituted B-rings and appropriate hydroxyls positioning on the A-rings might be critical in determining the activity and selectivity against H1N1-Tamiflu-resistant infected influenza viruses.
- Chung, Shu-Ting,Chien, Pei-Yu,Huang, Wen-Hsin,Yao, Chen-Wen,Lee, An-Rong
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p. 415 - 421
(2014/05/20)
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- Hydrolysis of scutellarin and related glycosides to scutellarein and the corresponding aglycones
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Scutellarein has been prepared by the hydrolysis of scutellarin with sulfuric acid to provide this biologically important rare flavone in up to > 90% yield and on the 5 g scale in minutes. This protocol has been applied to five other flavonoid glycosides (rutin, hesperidin, naringin, baicalin and diosmin) which are readily hydrolysed to their corresponding aglycones.
- Zhang, Wei,Yi, Dong,Gao, Kai,Liu, Manshuo,Yang, Jian,Liao, Xiali,Yang, Bo
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p. 396 - 398
(2014/08/05)
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- Efficient method for demethylation of aryl methyl ether using aliquat-336
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A rapid method for selective cleavage of aryl methylethers can be achieved in the presence of a protic acid and a catalytic amount of phase-transfer catalyst (Aliquat-336). Aliquat-336 accelerates the rate of reaction and affords the corresponding phenols in excellent to good yields on a wide variety of substrates. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
- Waghmode, Suresh B.,Mahale, Ganesh,Patil, Viraj P.,Renalson, Kartik,Singh, Dharmendra
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supporting information
p. 3272 - 3280
(2013/10/01)
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- 4′-Bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages
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The regulations of the NO and PGE2 productions are research topics of interest in the field of anti-inflammatory drug development. In the present study, 5,6,7-trimethoxy- and 5,6,7-trihydroxyflavones 3a-3g were synthesized from cinnamic acid derivatives. In particular, 4′-bromo-5,6,7- trimethoxyflavone (3b) most potently inhibited the productions of NO and PGE2 in LPS-treated RAW 264.7 cells (IC50 = 14.22 ± 1.25 and 10.98 ± 6.25 μM, respectively), and these inhibitory effects were more potent than those of oroxylin A or baicalein. Consistent with these findings, 3b concentration-dependently reduced the LPS-induced expressions of iNOS and COX-2 at the protein and mRNA levels. In addition, the release of TNF-α, IL-6, and IL-1β and the mRNA expressions of these cytokines were reduced by 3b in a concentration-dependent manner. Furthermore, 3b attenuated the LPS-induced transcriptional activities of NF-κB and this was accompanied by parallel reductions in the degradation and phosphorylation of IκB-α, and consequently by a decrease in the nuclear translocation of the p65 subunit of NF-κB. Taken together, these results suggest that suppressions of the expressions of iNOS, COX-2, TNF-α, IL-6, and IL-1β via NF-κB inactivation are responsible for the anti-inflammatory effects of 3b.
- Kim, Dong Han,Yun, Chang Hyeon,Kim, Min Hwan,Naveen Kumar, Ch.,Yun, Bo Hee,Shin, Ji-Sun,An, Hyo Jin,Lee, Young Hun,Yun, Yong Don,Rim, Hong-Kun,Yoo, Min-Sang,Lee, Kyung-Tae,Lee, Yong Sup
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scheme or table
p. 700 - 705
(2012/03/26)
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- Synthesis and biological evaluation of 8-substituted and deglucuronidated scutellarin and baicalin analogues as antioxidant responsive element activators
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Flavonoids are important bioactive dietary compounds, which are proved to be antioxidant responsive element (ARE) activators to defend against electrophilic toxicants and oxidative stress. The activators induce ARE gene transcription through Nrf2 factor, a major transcriptional stimulator of cytoprotective genes, relieved from a Keap1 complex. In this report, based on the structures of two flavonoids, scutellarin and baicalin, which are extracted from two common Chinese plants Dengzhanhua (Erigeron breviscapus (vant) Hand-Mazz) and Huangqin (Scutellaria baicalensis Georigi), respectively, we synthesized several 8-substituted and deglucuronidated analogues and identified the ARE activation effects of these flavonoids. We found that the Baicalin, deglucurnonidated Baicalin and diaza cyclopenta derivative were more active. Their dose-dependent upregulation activities of ARE and NQO1 and induction effects of Nrf2 were testified. The results presented that these three analogues had good upregulation effects on ARE, and they could be potentially utilized in relieving oxidative stress, upon further neuroprotective tests.
- Yang, Ping,Kong, XiangZhen,Cheng, ChangMei,Li, ChangYan,Yang, XiaoMing,Zhao, Xing'E
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experimental part
p. 1565 - 1575
(2012/04/05)
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- Total synthesis of baicalein
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In this paper, a simple and novel synthesis of baicalein is described. This transformation features the novel synthesis of helilandin B and a different way to demethylate. The overall yield of 59% is acceptable.
- Chen, Duo-Zhi,Yang, Jian,Yang, Bo,Wu, Yuan-Shuang,Wu, Ting
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experimental part
p. 124 - 128
(2010/08/05)
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- Convergent synthesis of mosloflavone, negletein and baicalein from crysin
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An expeditious synthesis of three polyoxygenated flavones: mosloflavone, negletein and baicalein, starting from crysin, an easily available flavone, by a bromination/methoxylation procedure is reported. The convergent synthesis exploits a base induced Wesley-Moser type rearrangement.
- Righi, Giuliana,Antonioletti, Roberto,Silvestri, Ilaria Proietti,D'Antona, Nicola,Lambusta, Daniela,Bovicelli, Paolo
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experimental part
p. 1294 - 1298
(2010/04/02)
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- Nitrogen-containing flavonoid analogues as CDK1/cyclin B inhibitors: Synthesis, SAR analysis, and biological activity
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A series of nitrogen-containing flavonoid analogues were designed and synthesized by Mannich reaction, and screened for the inhibitory activities of cyclin-dependent kinases using a FRET-based biochemical assay method. The results showed that C-8 nitrogen-containing baicalein analogues 3a-3f exhibited potent CDK1/Cyclin B inhibitory activities. 5,6,7-Trihydroxy-8-(dimethylaminomethyl)-2-phenyl-4H-chromen-4-one 3a, 5,6,7-trihydroxy-8-(pyrrolid inylmethyl)-2-phenyl-4H-chromen-4-one 3b, and 5,6,7-trihydroxy-8-(piperidinylmethyl)-2-phenyl-4H-chromen-4-one 3c (IC50 1.05-1.28 μM) were about sixfold more potent than baicalein 2 (IC50 6.53 μM). 5,6,7-Trihydroxy-8-(morpholinomethyl)-2-phenyl-4H-chromen-4-one 3d, 5,6,7-trihydroxy-8-(thiomorpholinomethy)-2-phenyl-4H-chrom en-4-one 3e, and 5,6,7-trihydroxy-8-(4-methylpiperazinylmethyl)-2-phenyl-4H-chromen-4-one 3f (IC50 0.27-0.38 μM) were about 20-fold more potent than baicalein, and were at the same level as flavopiridol (IC50 0.33 μM).
- Zhang, Shixuan,Ma, Jigang,Bao, Yongming,Yang, Puwen,Zou, Liang,Li, Kangjian,Sun, Xiaodan
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p. 7128 - 7133
(2008/12/22)
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- Compositions of flavonoids and flavonoid-containing extracts and the treatment of diseases
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In this invention, we describe a group of flavonoids and flavonoid-containing extracts that have pharmaceutical properties which are useful in the medicinal therapy of fibrotic diseases for the treatment or reparation and prevention of fibrotic lesional tissues. Representative flavonoids and flavonoid-containing extracts have the active compositions of the below formula. Those compositions can be extracted and purified from the botanicals, including Scutellaria baicalensis Georgi, Scutellaria scordifolia Fisch,Oroxylum indicum(L.) Vent, Plantago major L. The compositions of the invention are novel as an anti-fibrotic drugs, as agents for treating fibrosis.
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Page/Page column 25
(2008/06/13)
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- Preparation having antioxidant properties
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The invention relates to a preparation having antioxidant properties, comprising at least one compound of the formula I where R1 to R10 may be identical or different and are selected from H, OR11, straight-chain or branched C1- to C20-alkyl groups, straight-chain or branched C3- to C20-alkenyl groups, straight-chain or branched C1- to C20-hydroxyalkyl groups, where the hydroxyl group may be bonded to a primary or secondary carbon atom of the chain and furthermore the alkyl chain may also be interrupted by oxygen, and/or C3- to C10-cycloalkyl groups and/or C3- to C12-cycloalkenyl groups, where the rings may each also be bridged by —(CH2)n— groups, where n=1 to 3, where all OR11 are, independently of one another, OH, C1- to C20-alkoxy groups, C3- to C20-alkenyloxy groups, straight-chain or branched C1- to C20-hydroxyalkoxy groups and/or C3- to C10-cycloalkoxy groups and/or C3- to C12-cycloalkenyloxy groups, where the rings may each also be bridged by —(CH2)n— groups, where n=1 to 3, and/or mono- and/or oligoglycosyl radicals, with the proviso that at least 3 radicals from R1 to R7 are OH and that at least 2 pairs of adjacent —OH groups are present in the molecule, or R2, R5 and R6 are OH and the radicals R1, R3, R4 and R7-10 are H.
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- Methods of synthesizing flavonoids and chalcones
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Simple and efficient total syntheses of flavonoids including baicalein, oroxylin A and wogonin are described herein. Simultaneous syntheses of oroxylin A and wogonin are also described.
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- Novel synthesis of flavonoids of Scutellaria baicalensis Georgi.
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A concise and efficient total synthesis of the flavonoids baicalein, oroxylin A and wogonin was described. Intramolecular oxidative cyclization followed by demethylation of chalcone 1, readily prepared from trimethoxyphenol, afforded, depending upon the controlled conditions, baicalein or oroxylin A in excellent yields. Demethylation of 1 yielded 3, which, by oxidation with I(2)/dimethyl sulfoxide (DMSO), was readily converted to oroxylin A and wogonin after column chromatography.
- Huang, Wen-Hsin,Chien, Pei-Yu,Yang, Ching-Huey,Lee, An-Rong
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p. 339 - 340
(2007/10/03)
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- Novel use of flavones
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A pharmaceutical composition for inhibiting COX-2 biosynthesis comprising a therapeutically effective amount of the compound of formula I and a pharmaceutrically acceptable carrier. wherein R1 and R4 represent either Hydrogen or together a bond R5, R6, R7, R8 represent independently of each other Hydrogen, Hydroxy or Methoxy; in addition R7 represents a sugar substituent like glucoside, rutinosid, manno gluco pyransyl, aprosylglucoside R2 and R3 represent Hydrogen, Hydroxy, Methoxy or wherein R2′, R3′, R4′, R5′ and R6′ are independently or each other Hydrogen, Hydroxy or Methoxy with the proviso, that R2 or R3 is represented by the optionally substituted Phenylring.
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- Liposomes containing scutellaria extracts
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A composition having anti-inflammatory, anti-allergic or anti-aging activity comprising hydrated lipidic lamellar phases or liposomes containing an extract of Scutellaria and a method for treating inflammation, allergies or aging by topical administration of the composition.
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