Diarylheptanoid-flavanone adducts from Alpinia officinarum and their neuroprotective activities.

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 char...

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Publicado en:Fitoterapia Vol. 184
Autores principales: Ren, Teng, Miao, Qiuping, Pan, Yan, Zhang, Shiqing, Shi, Lei, Wang, Ying, Ye, Wen-Cai, Wu, Zhen-Long, Huang, Xiao-Jun, Song, Jian-Guo
Formato: research Journal Article
Publicado: Elsevier B.V. Jul2025
Acceso en línea:Ver este registro en EBSCOhost
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      dt: Jul2025
      vid: 184
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      pub: Elsevier B.V.
      place: New York, New York
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        186132751
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        10.1016/j.fitote.2025.106594
        186132751
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        atl: Diarylheptanoid-flavanone adducts from Alpinia officinarum and their neuroprotective activities.
      aug:
        au:
          Ren, Teng
          Miao, Qiuping
          Pan, Yan
          Zhang, Shiqing
          Shi, Lei
          Wang, Ying
          Ye, Wen-Cai
          Wu, Zhen-Long
          Huang, Xiao-Jun
          Song, Jian-Guo
        affil: State Key Laboratory of Bioactive Molecules and Druggability Assessment, Guangdong Basic Research Center of Excellence for Natural Bioactive Molecules and Discovery of Innovative Drugs, Jinan University, Guangzhou 510632, People's Republic of China
      sug:
        subj:
          Hydrocarbons, Aromatic Analysis
          Flavanones Analysis
          Plants, Medicinal Analysis
          Neuroprotective Agents Analysis
          Spectrum Analysis
          X-Rays Methods
          Chromones
          Neurons Injuries
          Oxygenation
          Glucose
          Molecular Structure
      ab: 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. [Display omitted]
      pubtype: Academic Journal
      doctype:
        research
        Journal Article
      ougenre: Article
    language: English
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