1447-88-7Relevant academic research and scientific papers
An improved synthesis of 6-o-methyl-scutellarein through selective benzylation
Zhang, Wei,Dong, Ze-Xi,Gu, Ting,Li, Nian-Guang,Wu, Wen-Yu,Zhang, Peng-Xuan,Tang, Yu-Ping,Yang, Jian-Ping,Xue, Xin,Fang, Fang,Li, He-Min,Cheng, Hai-Bo,Duan, Jin-Ao,Shi, Zhi-Hao
, p. 674 - 676 (2015)
An improved synthesis of 6-O-methyl-scutellarein is described. Benzyl bromide was selected to protect both the hydroxyl groups at C-4'and C-7 in scutellarein. The product was then methylated and deprotected to produce the target compound in high yield in four steps.
Enzymatic production of oroxylin A and hispidulin using a liverwort flavone 6-O-methyltransferase
Zhang, Yu-Ying,Xu, Rui-Xue,Gao, Shuai,Cheng, Ai-Xia
, p. 2619 - 2628 (2016)
Oroxylin A and hispidulin, compounds which are abundant in both Scutellaria and liverwort species, are important lead compounds for the treatment of ischemic cerebrovascular disease. Their enzymatic synthesis requires an O-methyltransferase able to interact with the related flavonoid's 6-OH group, but such an enzyme has yet to be identified in plants. Here, the gene encoding an O-methyltransferase (designated PaF6OMT) was isolated from the liverwort species Plagiochasma?appendiculatum. A test of alternative substrates revealed that its strongest preferences were baicalein and scutellarein, which were converted into, respectively, oroxylin A and hispidulin. Allowed a sufficient reaction time, the conversion rate of these two substrates was, respectively, 90% and 100%. PaF6OMT offers an enzymatic route to the synthesis of oroxylin A and hispidulin.
Preparation method of hispidulin
-
Paragraph 0042-0047, (2020/08/18)
The invention relates to the field of chemical synthesis, and relates to a novel preparation method of hispidulin, in particular to a method for preparing and synthesizing hispidulin by using scutellarin as a raw material. According to the method disclosed by the invention, scutellarin is used as a raw material, and the hispidulin can be efficiently semi-synthesized through three steps of reactions of carboxyl esterification, selective methylation and glycosyl hydrolysis. The method has the advantages of few reaction steps (only three steps), high reaction yield, cheap and easily available reaction reagents and low production cost. Moreover, the method is mild in reaction conditions, free of harsh reaction conditions, easy to operate and suitable for industrial production.
Semi-synthesis of a series natural flavonoids and flavonoid glycosides from scutellarin
Ding, Ning,Li, Yingxia,Wang, Yujie,Xiao, Qiang,Xie, Mingxian,Yan, Shiqiang
, (2020/01/22)
Natural flavonoids and flavonoid glycosides exist in many plants and have been demonstrated to possess various clinically relevant properties, isolating large amounts of these compounds that have striking structural similarity from plant sources needs tedious isolation techniques. These processes limited their availability in structural diversity for structure?activity relationship (SAR) studies, and restrict large quantities for, as an example, their mechanistic evaluation of the in vivo activities. In this work, we developed a semi-synthetic strategy from scutellarin for the synthesis of a series of natural flavonoids and flavonoid glycosides. By taking this strategy, eight bioactive flavonoids with striking structural similarities were synthesized efficiently and practically. The sufficient amounts obtained products will greatly facilitate the SAR studies and mechanistic evaluation of the in vivo activities.
Synthesis and biological evaluation of scutellarein alkyl derivatives as preventing neurodegenerative agents with improved lipid soluble properties
Li, He-Min,Gu, Ting,Wu, Wen-Yu,Yu, Shao-Peng,Fan, Tian-Yuan,Zhong, Yue,Li, Nian-Guang
, p. 771 - 780 (2019/11/02)
Background: Exogenous antioxidants are considered as a promising therapeutic approach to treat neurodegenerative diseases since they could prevent and/or minimize the neuronal damage by oxidation. Objective: Three series of lipophilic compounds structurally based on scutellarein (2), which is one metabolite of scutellarin (1) in vivo, have been designed and synthesized. Methods: Their antioxidant activity was evaluated by detecting the 2-thiobarbituric acid reactive substance (TBARS) produced in the ferrous salt/ascorbate-induced autoxidation of lipids, which were present in microsomal membranes of rat hepatocytes. The lipophilicity of these compounds indicated as partition coefficient between n-octanol and buffer was investigated by ultraviolet (UV) spectrophotometer. Results: This study indicated that compound 5e which had a benzyl group substituted at the C4'-OH position showed a potent antioxidant activity and good lipophilicity. Conclusion: 5e could be an effective candidate for preventing or reducing the oxidative status associated with the neurodegenerative processes.
METHOD FOR PREPARING HISPIDULIN AND ITS DERIVATIVES
-
, (2019/11/05)
Provided is a method for preparing hispidulin or a derivative thereof. The method includes selective protection of trihydroxybenzaldehyde, followed by regioselective iodination, selective protection, Stille coupling, Baeyer-Villiger oxidation and basic hydrolysis to obtain a protected intermediate compound. Then, alkylation, Claisen-Schmidt condensation, cyclization and deprotection of the protected intermediate compound are performed to obtain hispidulin or the derivative thereof. The present disclosure provides an efficient method for total synthesis of hispidulin or the derivative thereof with concise reaction steps and high yield.
Total synthesis and metabolic stability of hispidulin and its d-labelled derivative
Chen, Liang-Chieh,Hsu, Kai-Cheng,Chiou, Lih-Chu,Tseng, Hui-Ju,Huang, Wei-Jan
, (2017/11/20)
Hispidulin is a naturally occurring flavone known to have various Central nervous system (CNS) activities. Proposed synthetic approaches to synthesizing hispidulin have proven unsatisfactory due to their low feasibility and poor overall yields. To solve these problems, this study developed a novel scheme for synthesizing hispidulin, which had an improved overall yield as well as more concise reaction steps compared to previous methods reported. Additionally, using the same synthetic strategy, d-labelled hispidulin was synthesized to investigate its metabolic stability against human liver microsome. This work may produce new chemical entities for enriching the library of hispidulin-derived compounds.
A 6-methyl Scutellarin arctigenin method for the preparation of (by machine translation)
-
Paragraph 0045; 0046, (2017/04/06)
The invention relates to the field of chemical synthesis, in particular to Chinese traditional medicine molecule Scutellarin active metabolite of preparation, the ponicidin breviscapine under the action of the strong acid hydrolysis glucuro molecules are the 4 [...], 5, 6, 7? Four hydroxy flavone, the 4 [...], 5, 6, 7? Four hydroxy flavone with bromo the presence of the acid-binding agent, generating 5,6? Dihydroxybenzonic? 4 the [...], 7? B benzyloxy flavone, then in alkaline conditions with iodomethane reaction generating 5? Hydroxy? 6? Methoxy? 4 the [...], 7? B benzyloxy flavone, the final 5? Hydroxy? 6? Methoxy? 4 the [...], 7? B benzyloxy-flavone in palladium carbon catalytic hydrogenation by debenzylation in the presence of 6? Methyl Scutellarin aglycon. The step of this invention is simple, is easy to be purified, mild condition, low cost, overall reaction yield is greater than 70%, the synthetic product has high purity, greater than 99.0%, suitable for technical production. (by machine translation)
A new and efficient synthesis of 6-O-methylscutellarein, the major metabolite of the natural medicine scutellarin
Zhang, Wei,Dong, Ze-Xi,Gu, Ting,Li, Nian-Guang,Zhang, Peng-Xuan,Wu, Wen-Yu,Yu, Shao-Peng,Tang, Yu-Ping,Yang, Jian-Ping,Shi, Zhi-Hao
, p. 10184 - 10191 (2015/08/06)
In this paper, a new and efficient synthesis of 6-O-methylscutellarein (3), the major metabolite of the natural medicine scutellarin, is reported. Two hydroxyl groups at C-4′ and C-7 in 2 were selectively protected by chloromethyl methyl ether after the reaction conditions were optimized, then 6-O-methyl-scutellarein (3) was produced in high yield after methylation of the hydroxyl group at C-6 and subsequent deprotection of the two methyl ether groups.
Total Synthesis of Hispidulin and the Structural Basis for Its Inhibition of Proto-oncogene Kinase Pim-1
Chao, Shi-Wei,Su, Ming-Yuan,Chiou, Lih-Chu,Chen, Liang-Chieh,Chang, Chung-I,Huang, Wei-Jan
, p. 1969 - 1976 (2015/09/08)
(Figure Presented). A new method is applied to synthesize hispidulin, a natural flavone with a broad spectrum of biological activities. Hispidulin exhibits inhibitory activity against the oncogenic protein kinase Pim-1. Crystallographic analysis of Pim-1 bound to hispidulin reveals a binding mode distinct from that of quercetin, suggesting that the binding potency of flavonoids is determined by their hydrogen-bonding interactions with the hinge region of the kinase. Overall, this work may facilitate construction of a library of hispidulin-derived compounds for investigating the structure-activity relationship of flavone-based Pim-1 inhibitors.
