- 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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- Synthesis of 5-Hydroxy-3′,4′,7-trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2-Mediated Anticancer Drug Resistance
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3′,4′,7-Trimethoxyflavone (TMF) has been reported to show a potent reversal effect on drug resistance mediated by breast cancer resistance protein (BCRP)/ATP-binding cassette subfamily G member 2 (ABCG2). In this study, we designed and synthesized five derivatives with either a hydroxy group or a fluorine atom at C-5 and several kinds of capping moiety at the C-7 hydroxy group, on the same 3′,4′-dimethoxy-substituted flavone skeleton. We subsequently evaluated the efficacies of these compounds against BCRP-expressing human leukaemia K562/BCRP cells. Reversal of drug resistance was expressed as the concentration of compound causing a twofold reduction in drug sensitivity (RI50). Of the synthesized compounds, the reversal effect of 5-hydroxy-3′,4′,7-trimethoxyflavone (HTMF, RI50 7.2 nm) towards 7-ethyl-10-hydroxycamptothecin (SN-38) was stronger than that of TMF (RI50 18 nm). Fluoro-substituted 5-fluoro-3′,4′,7-trimethoxyflavone (FTMF, RI50 25 nm) and monoglycosylated 7-(β-glucosyloxy)-5-hydroxy-3′,4′-dimethoxyflavone (GOHDMF, 91 nm) also exhibited reversal effects, whereas the di- and triglycoside derivatives did not. TMF, HTMF and FTMF at 0.01–10 μm upregulated the K562/BCRP cellular accumulation of Hoechst 33342 nuclear staining dye. In addition, western blotting revealed that treatment of K562/BCRP cells with 0.1 μm TMF, HTMF or FTMT suppressed the expression of BCRP. HTMF showed the strongest inhibition of BCRP-mediated efflux and suppression of BCRP expression of the three effective synthesized flavones.
- Tsunekawa, Ryuji,Katayama, Kazuhiro,Hanaya, Kengo,Higashibayashi, Shuhei,Sugimoto, Yoshikazu,Sugai, Takeshi
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p. 210 - 220
(2018/10/15)
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- Semi-synthesis method of diosmetin
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The invention provides a semi-synthesis method of diosmetin. A purpose of the present invention is to solve the problems of high production cost and low synthesis efficiency of the existing synthesismethod. According to the present invention, neohesperidin, pyridine and iodine are heated and react to prepare neodiosmin, and the neodiosmin is hydrolyzed with a sodium hydroxide solution to preparediosmetin; and the semi-synthesis method has characteristics of short process time, simple post-treatment, low production cost, high product purity and high yield, and is suitable for the industrial production of diosmetin.
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Paragraph 0027-0030; 0035-0038; 0043-0046; 0051-0054
(2019/01/23)
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- PROCESS FOR THE PREPARATION OF DIOSMIN
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The present invention relates to a process for the preparation of diosmin from hesperidin. The process involves the oxidation of acylated hesperidin with iodine or bromine in a C2-C4 carboxylic acid medium and subsequent treatment with an inorganic base to partially neutralize the acidic media. The process allows obtaining diosmin with low iodine or bromine content, avoiding the use of organic solvents.
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- Method for preparing green and economic diosmin
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The invention discloses a method for preparing green and economic diosmin. The method comprises three main steps of preparation, recycling and refining. Compared with a conventional method, the method thoroughly avoids use of pyridine and inorganic base, the production environment is greatly improved, the aftertreatment is simple, iodine and solvents can be recycled, the reaction conditions are gentle, the production cost is low, and meanwhile in the method, a crude product is not refined in a classic alkali solution acidification mode instead of a mode that diosmin is separated out, then the purity of a finished product can be up to 99%, the product quality can be improved, and moreover the method is simple and convenient to operate and applicable to industrial production.
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Paragraph 0040; 0041
(2016/10/17)
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- Method for semi-synthesizing 3-deoxyanthocyanidin from 5-OH-7-O-substituted flavanone
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The invention relates to a method for semi-synthesizing 5-OH-7-O-substituted-3-deoxyanthocyanidin from 5-OH-7-O-substituted flavanone, and relates to the fields of chemistry and pharmacy, food and cosmetics. According to the invention, 5-OH-7-O-substituted flavanone is reduced into 5-OH-7-O-substituted flavan-4-ol with reducing agents such as potassium borohydride; direct acid dehydration is carried out, such that a 5-OH-7-O-substituted flavan-4-carbonium ionic compound is produced; water is removed, and iodine-pyridine solvent dehydrogenation is carried out, such that 5-OH-7-O-substituted-3-deoxyanthocyanidin is produced. The 5-OH-7-O-substituted-3-deoxyanthocyanidin is subjected to macroporous absorption resin enrichment, and harmful impurities such as pyridine are removed; and ethanol elution and reduced-pressure recovery are carried out, such that the final product is obtained. According to the invention, multiple reaction steps are integrated into a one-step reaction; operation is simple; and yield is relatively high. The method is suitable for industrial productions. With the method, flavanone glycosides such as hesperidin and naringin can be prepared into 3-deoxyanthocyanidin with good water solubility and oxidation resistance.
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Paragraph 0025
(2016/11/28)
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- A new technology for producing crane wooden glucoside
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The invention discloses a novel production technology of diosmin, which comprises the following steps that a dehydrogenation reaction is performed; a crude diosmin product is prepared, dried, and subjected to iodine residual removal; a solvent residual of diosmin is removed; a fine diosmin product is dried, and subjected to a diosmin micronization technology; and micronized diosmin meeting a requirement of EP8.0 (European Pharmacopoeia 8.0) is obtained. The novel production technology has the characteristic of sociometric sustainable development; no harmful effect is exerted on an environment in a production process; more importantly, the consumption of a dehydrogenation agent is reduced to be 2-5% of that of hesperidin in the production process, so that a raw material resource is used fully to the greatest extent; the solvent and iodine residuals are removed effectively; and development requirements of a resource-saving and environment-friendly society are met.
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Paragraph 0016
(2017/01/26)
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- PROCESS FOR THE PREPARATION OF DIOSMIN
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The process of preparation of pure diosmin that is independent of hesperidine used for conversion is described. Process is effective in controlling the impurity by crystallization. The cost effective and ecofriendly process enables recovery and recycling of the reagents involved in the manufacturing process.
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Page/Page column 9; 10
(2010/09/03)
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- Mild alkaline hydrolysis of some 7-O-flavone glycosides. Application to a novel access to rutinose heptaacetate
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Alkaline hydrolysis of some 7-O-flavone glycosides was performed through the 6,8-dibromo derivative. When the sugar linked to the aglycon has a 2-hydroxy group trans to the sugar-aglycon bond as in β-D-glucosides or rutinosides, hydrolysis occurred at room temperature under very mild conditions. Application to a novel preparation of rutinose heptaacetate by hydrolysis of a diosmin derivative is described.
- Quintin, Jér?me,Lewin, Guy
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p. 4341 - 4343
(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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- STRUCTURAL ASPECTS OF ANTHOCYANIN-FLAVONOID COMPLEX FORMATION AND ITS ROLE IN PLANT COLOR
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Key Word Index - Anthocyanin; flavonoid glycosides; synthesis; complex formation; plant color; spectral properties. The complex formation of flavonoids with anthocyanins, resulting in increase in both absorbance and in a bathochromic shift of the visible absorption maximum of the latter, is based mainly on hydrogen bond formation between the carbonyl group of the anthocyanin anhydrobase and aromatic hydroxyl groups of the complex-forming flavonoids.The larger the number of hydroxyl groups in the flavonoid molecule, the strongr the complex formation.The presence of a 3-hydroxyl group in the flavonoid molecule has little effect on the complex-forming ability.The nature of the sugar substituent of the complex-forming flavonoid compound has no influence on the reaction.The 5-hydroxyl group of flavonoids is strongly bound by intramolecular hydrogen bond to the 4-carbonyl and does not participate in the complex formation.The most important hydroxyl group in the flavonoid molecule is one in the 7-position.Unsaturation at C2-C3 in the heterocyclic ring is an important factor for complex formation.Aromatic hydroxyl groups in the flavonoid system alone cannot account for all the complex-forming ability, suggesting additional involvment by electrostatic forces and configurational or steric effects.
- Chen, Lao-Jer,Hrazdina, Geza
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p. 297 - 304
(2007/10/02)
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