(±)-Hyperpyran A: Terpenoid-based bicyclic dihydropyran enantiomers with hypoglycemic activity from Hypericum perforatum (St. John's wort)

Authors：Zhao, Xuebing; Guo, Yi; Xu, Qianqian; Shi, Zhengyi; Xiang, Ming; Li, Hua; Wang, Yanyan^*; Qi, Changxing^*; Zhang, Yonghui^*

Source：FITOTERAPIA, 2022, 161: 105221.

DOI：10.1016/j.fitote.2022.105221

• Hypericum perforatum L.
• St. John's wort
• Bicyclic dihydropyran
• Enantiomers
• Hypoglycemic activity

(+/-) Hyperpyran A (1a/1b), a pair of new terpenoid-based bicyclic dihydmpyran enantiomers, were isolated from the aerial parts of Hypericum perforatum (St. John's wort). Their structures and absolute configurations were elucidated by NMR spectroscopic analyses, ECD comparison, and X-ray crystal diffraction. Compounds 1a/1b possess hexahydrocyclopenta [c] pyran ring system and a plausible biosynthetic pathway was also proposed. In addition, compound la exhibited a moderate promotion of glucose uptake activity in hepatocytes.

• Institution
  Huazhong University of Science and Technology; 1