Anti-Inflammatory, Antioxidant, and Anti-Nonalcoholic Steatohepatitis Acylphloroglucinol Meroterpenoids from Hypericum bellum Flowers

J Agric Food Chem. 2021 Jan 20;69(2):646-654. doi: 10.1021/acs.jafc.0c05417. Epub 2021 Jan 11.

Abstract

In this work, 26 methylated acylphloroglucinol meroterpenoids with diverse skeletons, including 18 new ones (bellumones A-R, 1-18), were identified from the flowers of Hypericum bellum. Their structures including absolute configurations were elucidated by detailed spectroscopic data, calculated electronic circular dichroism (ECD), and X-ray diffraction (XRD). Through methylation at C-5, prenylation with different chain lengths of the acylphloroglucinol-derived core, along with different types of secondary cyclization, type A bicyclic polyprenylated acylphloroglucinols (BPAPs) (1-5 and 19-24) and dearomatized isoprenylated acylphloroglucinols (DIAPs) (6-18 and 25-26) were obtained. The significant results of anti-inflammatory, antioxidant, and anti-nonalcoholic steatohepatitis (anti-NASH) activities suggest its usefulness in daily health care.

Keywords: Hypericum bellum; acylphloroglucinol meroterpenoids; anti-NASH activity; anti-inflammatory activity; antioxidant activity.

MeSH terms

  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Antioxidants / chemistry*
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology
  • Flowers / chemistry
  • Humans
  • Hypericum / chemistry*
  • Molecular Structure
  • Non-alcoholic Fatty Liver Disease / drug therapy
  • Phloroglucinol / chemistry*
  • Phloroglucinol / isolation & purification
  • Phloroglucinol / pharmacology
  • Terpenes / chemistry
  • Terpenes / isolation & purification
  • Terpenes / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Antioxidants
  • Terpenes
  • Phloroglucinol