- Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo
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Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)-1 and (S)-1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC-ECD coupling. (R)-1 and (S)-1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)-enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short- and long-term memory at low dosages.
- Hofmann, Julian,Fayez, Shaimaa,Scheiner, Matthias,Hoffmann, Matthias,Oerter, Sabrina,Appelt-Menzel, Antje,Maher, Pamela,Maurice, Tangui,Bringmann, Gerhard,Decker, Michael
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p. 7299 - 7308
(2020/05/18)
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- TECHNICAL PROCESS FOR ISOLATING FLAVANONES
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The invention relates to the extraction of technical quantities of pure and natural homoeriodictyols (3`-methoxy-4`,5,7-trihydroxyflavanone) in the form of homoeriodictyol sodium salt and of sterubin (7-methoxy-3`,4`,5-trihydroxyflavanone) from plants of the genus Eriodictyon. To this end, the plant material is extracted using a non-water miscible extractant, the extract is dewaxed, is optionally prepurified using activated carbon, is treated with a sodium ion-containing, basic, aqueous solution, and the precipitated homoeriodictyol sodium salt is purified by reprecipitation or crystallization.
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Page/Page column 11
(2008/06/13)
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- Synthesis of hydroxyflavanones from substituted acetophenones and benzaldehydes in the presence of silica gel, boric acid and piperidine
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Direct synthesis of hydroxyflavanones from appropriately substituted acetophenones and benzaldehydes was achieved in the presence of boric acid, silica gel and piperidine. The formation of flavanones presumably involved the reaction between the acetopheno
- Zhang, Wei Han,Chan, Wing Lai,Lin, Yuan Hua,Szeto, Yau Shan,Lin, Yong Cheng,Yeung, Chi Hung
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- One step synthesis of polyhydroxyflavan ones from hydroxyacetophenones and hydroxybenzaldehydes
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Polyhydroxyflavanones were synthesized in a one-step process by reacting the appropriate hydroxyacetophenones and hydroxybenzaldehydes in the presence of boric acid, in a mixed solvent system.
- Chan, Wing Lai,Lin, Yong Cheng,Zhang, Wei Han,Tang, Pak Lai,Szeto, Yau Shan
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p. 551 - 554
(2007/10/03)
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- Synthesis of a Typical Chalkone and a Flavanone of Wyethia glabra
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The constitution of a new chalkone as 2',4',6'-trihydroxy-4-methoxychalkone (1), isolated from Wyethia glabra has now been confirmed by its synthesis using 2'-hydroxy-4',6'-dibenzoyloxy-4-methoxychalkone (1a) as an essential intermediate.The structure of another compound as 5,3',4'-trihydroxy-7-methoxyflavanone (2) (eriodictyol-7-methyl ether) isolated from the same source, has also been confirmed by its synthesis using vanillin as the starting material.
- Babber, Sunanda,Chandra, S.,Aggarwal, Anil K.
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p. 797 - 798
(2007/10/02)
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- Structural Confirmation of Eriodictyol 7-Methyl Ether, a New Flavone Occurring in Wyethia glabra Nutt
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5,3',4'-Trihydroxy-7-methoxyflavanone (III), isolated from Wyethia glabra Nutt. , designated as eriodictyol 7-methyl ether, has been synthesised by the cyclization of 3,4-dibenzyloxy-2'-hydroxy-4',6'-dimethoxychylkone (I), followed by concerted debenzylation and partial demethylation of the resulting flavanone using anhydrous AlCl3 in acetonitrile.
- Rani, Indu
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