Ren Teng, Miao Qiuping, Pan Yan, Zhang Shiqing, Shi Lei, Wang Ying, Ye Wen-Cai, Wu Zhen-Long, Huang Xiao-Jun, Song Jian-Guo
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; Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research, Guangdong-Hong Kong-Macau Joint Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, People's Republic of China; Center for Bioactive Natural Molecules and Innovative Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, People's Republic of China.
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; Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM & New Drugs Research, Guangdong-Hong Kong-Macau Joint Laboratory for Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, People's Republic of China; Center for Bioactive Natural Molecules and Innovative Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, People's Republic of China.
Fitoterapia. 2025 Jul;184:106594. doi: 10.1016/j.fitote.2025.106594. Epub 2025 May 12.
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.
在高效液相色谱 - 紫外实验特有的高度π共轭体系的指导下，从药用植物高良姜的根茎中分离出四对对映体二芳基庚烷类 - 黄酮加合物，即高良姜素A - D（1 - 4）。通过广泛的光谱分析、单晶X射线衍射和密度泛函理论量子化学计算相结合的方法，对它们的结构及其绝对构型进行了全面表征。这些分离得到的化合物代表了一类新型的二芳基庚烷类 - 黄酮加合物，具有前所未有的C - 11 - C - 8'（C - 6'）和C - 9 - O - C - 7'连接模式。值得注意的是，化合物3和4在二氢吡喃并[2,3 - f]色酮或二氢吡喃并[3,2 - g]色酮骨架中含有不寻常的缩酮基序。在生物活性测定中，化合物2对SH - SY5Y细胞中氧糖剥夺和复氧（OGD/R）诱导的神经元损伤表现出显著的神经保护作用。
