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Fitoterapia

Fitoterapia

IF: 2.5
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Diarylheptanoid-flavanone adducts from Alpinia officinarum and their neuroprotective activities

Published:6 May 2025 DOI: 10.1016/j.fitote.2025.106594
Teng Ren , Qiuping Miao , Yan Pan , Shiqing Zhang , Lei Shi , Ying Wang , Wen-Cai Ye , Zhen-Long Wu , Xiao-Jun Huang , Jian-Guo Song

Abstract

Guided by the characteristic highly π-conjugated system of HPLC-UV experiments, four pairs of enantiomeric diarylheptanoid-flavanone adducts, officinoids A–D (14), were isolated from the rhizomes of medicinal plant Alpinia officinarum. Their structures with absolute configurations were fully characterized through a combination of extensive spectroscopic analysis, single-crystal X-ray diffraction, and density functional theory quantum chemical calculation. These isolated compounds represent a new class of diarylheptanoid-flavanone adducts with an unprecedented C-11–C-8′(C-6′) and C-9–O–C-7′ connection mode. Notably, compounds 3 and 4 contain an unusual ketal motif in the dihydropyrano[2,3-f]chromone or dihydropyrano[3,2-g]chromone skeleton. In the bioactivity assays, compound 2 exhibited significant neuroprotective effects against neuronal injury induced by oxygen-glucose deprivation and re?oxygenation (OGD/R) in SH-SY5Y cells.

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