Anti-inflammatory and Neurotrophic 2H-1-Benzopyran Derivatives of Chaenomeles sinensis

Two 2H-1-benzopyran derivatives, methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-5-carboxylate (1) and methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxylate (2), including a new compound (1) were isolated from the twigs of Chaenomeles sinensis. Their chemical structures were characterized based...

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Bibliographic Details
Published inNatural product sciences Vol. 28; no. 1; pp. 1 - 5
Main Authors Ha, Young Jun, Lee, Tae Hyun, Subedi, Lalita, Kim, Hye Ryeong, Moon, Gyuri, Kim, Sun Yeou, Kim, Chung Sub
Format Journal Article
LanguageKorean
Published 2022
Subjects
Chaenomeles sinensis
neurotrophic activity
2H-1-benzopyran derivatives
anti-neuroinflammation
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Summary:Two 2H-1-benzopyran derivatives, methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-5-carboxylate (1) and methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxylate (2), including a new compound (1) were isolated from the twigs of Chaenomeles sinensis. Their chemical structures were characterized based on analysis of NMR data including 1H and 13C, COSY, HSQC, and HMBC and HRMS data. The isolated compounds (1 and 2) were assessed for their anti-neuroinflammatory activity by measuring inhibition levels of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells and for their neurotrophic activity by the secretion of nerve growth factor (NGF) in C6 cells. Compounds 1 and 2 exhibited powerful anti-neuroinflammatory effects with IC50 values of 17.14 and 19.30 μM, respectively, without cell toxicity, and also showed moderate effects on the stimulation of NGF secretion levels with 113.15 ± 3.54 and 130.20 ± 8.03%, respectively. The biosynthetic pathway of 1 and 2 was proposed that they would be derived from a protocatechuic acid and an isoprenyl unit.
Bibliography:KISTI1.1003/JNL.JAKO202211162317407
ISSN:1226-3907