Diarylheptanoid-flavanone adducts from Alpinia officinarum and their neuroprotective activities

IF 2.5 3区医学 Q3 CHEMISTRY, MEDICINAL

Fitoterapia Pub Date : 2025-05-06 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

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Abstract

Guided by the characteristic highly π-conjugated system of HPLC-UV experiments, four pairs of enantiomeric diarylheptanoid-flavanone adducts, officinoids A–D (1–4), 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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厚朴中二芳基庚烷类黄酮加合物及其神经保护活性

在高效液相色谱-紫外光谱高π共轭体系的指导下，从药用植物Alpinia officinarum根茎中分离到四对对映体二芳基庚烷类黄酮加合物officinoid A-D（1-4）。通过广泛的光谱分析、单晶x射线衍射、密度泛函理论和量子化学计算，对其绝对构型结构进行了全面表征。这些分离的化合物代表了一类具有前所未有的C-11-C-8 ' （C-6 ‘）和C-9-O-C-7 ’连接模式的新型二芳基庚烷-黄酮加合物。值得注意的是，化合物3和4在二氢吡喃[2,3-f]或二氢吡喃[3,2-g]染色体骨架中含有一个不寻常的酮基序。在生物活性实验中，化合物2对SH-SY5Y细胞氧-葡萄糖剥夺和再氧合（OGD/R）诱导的神经元损伤具有显著的神经保护作用。

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来源期刊

Fitoterapia 医学-药学

CiteScore

5.80

自引率

2.90%

发文量

198

审稿时长

1.5 months

期刊介绍： Fitoterapia is a Journal dedicated to medicinal plants and to bioactive natural products of plant origin. It publishes original contributions in seven major areas: 1. Characterization of active ingredients of medicinal plants 2. Development of standardization method for bioactive plant extracts and natural products 3. Identification of bioactivity in plant extracts 4. Identification of targets and mechanism of activity of plant extracts 5. Production and genomic characterization of medicinal plants biomass 6. Chemistry and biochemistry of bioactive natural products of plant origin 7. Critical reviews of the historical, clinical and legal status of medicinal plants, and accounts on topical issues.