Rearranged 6/6/5/6-Fused Triterpenoid Acids from the Stems of Kadsura coccinea

J Nat Prod. 2016 Oct 28;79(10):2590-2598. doi: 10.1021/acs.jnatprod.6b00508. Epub 2016 Oct 5.

Abstract

Fourteen new rearranged 6/6/5/6-fused triterpenoid acids, namely, kadcoccine acids A-N (1-14), were isolated from an EtOAc-soluble extract of the stems of Kadsura coccinea. Their structures were characterized mainly by analyzing 1D and 2D NMR and HRESIMS data and were shown to feature a rare 14(13→12)-abeo-lanostane skeleton. Compounds 7 and 8 represented the first examples of a 5-substituted 2(5H)-furanone motif on the C-17 side chain of this skeleton. The absolute configurations of C-23 for compounds 1, 7, and 8 were determined by comparison of their experimental electronic circular dichroism spectra. All the isolates were screened for their in vitro cytotoxicity against six human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW-480, and HeLa), and compounds 2 and 8 exhibited weak inhibitory effects with IC50 values ranging from 3.11 to 7.77 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry*
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Female
  • HL-60 Cells
  • HeLa Cells
  • Humans
  • Kadsura / chemistry*
  • Lanosterol / chemistry
  • MCF-7 Cells
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Stems / chemistry*
  • Structure-Activity Relationship
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Triterpenes
  • Lanosterol