17306-46-6Relevant articles and documents
Discovery of potent and selective acetylcholinesterase (AChE) inhibitors: acacetin 7-O-methyl ether Mannich base derivatives synthesised from easy access natural product naringin
Liu, Hao-ran,Men, Xue,Gao, Xiao-hui,Liu, Lin-bo,Fan, Hao-qun,Xia, Xin-hua,Wang, Qiu-an
, p. 743 - 747 (2018)
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.
Continuous flow microchannel synthesis process of flavonoid compounds
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Paragraph 0050-0060, (2021/06/22)
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.
The invention relates to a raw material to synthesize the tin setose thistle glucoside naringin method (by machine translation)
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Paragraph 0017; 0020; 0021, (2018/11/22)
The invention discloses a to naringin as raw material synthetic tin setose thistle glucoside method, comprises the following steps: S1, synthesis of wild lacquer tree glucoside; S2, compound 5, 7 - dihydroxy - 2 - (4 - methoxyphenyl) - 4 H - chromen - 4 - one synthesis; acetoxy methyl) - 6 - ((5 - hydroxy - 2 - (4 - methoxyphenyl) - 4 - oxo - 4 H - chromen - 7 - yl) oxy) tetrahydro - 2 H - pyran - 3, 4, 5 - [...] acetate synthesis; S4, compound 5 - hydroxy - 2 - (4 - methoxyphenyl) - 7 - (( (2 S, 3 R, 4 S, 5 S, 6 R) - 3, 4, 5 - trihydroxy - 6 - (hydroxymethyl) tetrahydro - 2 H - pyran - 2 - Kiki) oxy) - 4 H - benzopyran - 4 - one synthesis. The invention to naringin as raw materials, by oxidation, methylation, hydrolysis reaction to synthesize tian jigan. (by machine translation)
Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step
Hanamura, Shun,Hanaya, Kengo,Shoji, Mitsuru,Sugai, Takeshi
, p. 19 - 26 (2016/03/30)
Acacetin and resveratrol 3,5-di-O-β-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules.
STRUCTURAL ASPECTS OF ANTHOCYANIN-FLAVONOID COMPLEX FORMATION AND ITS ROLE IN PLANT COLOR
Chen, Lao-Jer,Hrazdina, Geza
, p. 297 - 304 (2007/10/02)
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.
