Hepatoprotective Tetrahydrobenzocyclooctabenzofuranone Lignans from Kadsura longipedunculata

J Nat Prod. 2019 Oct 25;82(10):2842-2851. doi: 10.1021/acs.jnatprod.9b00576. Epub 2019 Sep 26.

Abstract

Three new tetrahydrobenzocyclooctabenzofuranone lignan glucosides, longipedunculatins A-C (1-3), a new dibenzocyclooctadiene lignan glucoside, longipedunculatin D (4), a new dibenzocyclooctadiene lignan (5), five new tetrahydrobenzocyclooctabenzofuranone lignans (6-10), and two new simple lignans (11, 12) were isolated from the roots of Kadsura longipedunculata. Their structures and absolute configurations were established using a combination of MS, NMR, and experimental and calculated electronic circular dichroism data. Compound 7 showed moderate hepatoprotective activity against N-acetyl-p-aminophenol-induced toxicity in HepG2 cells with a cell survival rate at 10 μM of 50.8%. Compounds 2, 7, and 12 showed significant in vitro inhibitory effects with an inhibition rate of 55.1%, 74.9%, and 89.8% on nitric oxide production assays at 10 μM.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Circular Dichroism
  • Cyclooctanes / chemistry
  • Cyclooctanes / isolation & purification
  • Cyclooctanes / pharmacology
  • Hep G2 Cells
  • Humans
  • Kadsura / chemistry*
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Liver / drug effects*
  • Magnetic Resonance Spectroscopy
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Plant Roots / chemistry
  • Protective Agents / chemistry
  • Protective Agents / isolation & purification
  • Protective Agents / pharmacology

Substances

  • Cyclooctanes
  • Lignans
  • Protective Agents
  • dibenzocyclooctadiene lignan
  • Nitric Oxide