Polycyclic polyprenylated acylphloroglucinol derivatives from Hypericum scabrum. Issue 21 (1st November 2017)

• Record Type: Journal Article
• Authors: Hu, Jiawen; Gao, Wan; Xu, Fang; Wei, Canjing; Shi, Mengjiao; Sun, Hua; Zhen, Bo; Wang, Jiajia; Ji, Tengfei; Jiang, Jiandong
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 21(2017)
• Page Start: 4932
• Page End: 4936
• Publication Date: 2017-11-01
• Subjects: Hypericum -- PPAPs -- ECD -- Hepatoprotective; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.09.001
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Highlights: Three new and seven known PPAPs were obtained from Hypericum scabrum . The new structures were elucidated by NMR data and ECD calculations. The plausible biosynthetic pathway for compounds1 –3 is proposed. Compounds3, 4, 5, and10 showed obvious hepatoprotective activities. Abstract: Three new polycyclic polyprenylated acylphloroglucinol derivatives (PPAPs), hyperibrins E–G (1 –3 ), along with seven known compounds were identified from the air-dried aerial parts of Hypericum scabrum. Their structures were determined by NMR spectroscopic methods, both experimental and calculated electronic circular dichroism (ECD) spectra and comparison with known compounds. Compound1 was derived from an analogue of compound2 by cyclization, while a retro -Claisen reaction transformed another analogue of compound2 into compound3 . Compounds3, 4, 5, and10 showed obvious hepatoprotective activities against paracetamol-induced HepG2 cell damage.