1447-88-7Relevant articles and documents
FLAVONOIDS OF Digitalis ciliata
Gvazava, L. N.,Alaniya, M. D.,Kemertelidze, E. P.
, p. 373 (1987)
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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.
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.