Bioactive Limonoid Constituents of Munronia henryi

J Nat Prod. 2015 Apr 24;78(4):811-21. doi: 10.1021/np501057f. Epub 2015 Mar 23.

Abstract

Fourteen new limonoids, munronins A-N (1-14), and eight known limonoids (15-22) were isolated from the whole plants of Munronia henryi. The structures of the new compounds were elucidated by 2D NMR spectroscopy and mass spectrometry, and the structure of 8 was confirmed by single-crystal X-ray diffraction analysis. Compound 1 represents the first limonoid found with a novel 7-oxabicyclo[2.2.1]heptane moiety produced by incorporating C-11 and C-14 via an oxygen atom. All compounds were evaluated for their anti-tobacco mosaic virus (TMV) activity and in vitro cytotoxicity against the human cancer HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines. Among them, compounds 2, 8, 9, 10, 11, 12, 18, and 20 showed significant anti-TMV activity, with IC50 values in the range 19.6-44.4 μg/mL. Compounds 1 and 18 exhibited cytotoxic effects for all five cancer cell lines, with IC50 values between 0.4 and 4.8 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*
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification*
  • Antiviral Agents / pharmacology*
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology*
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • Limonins / chemistry
  • Limonins / isolation & purification*
  • Limonins / pharmacology*
  • Meliaceae / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Tobacco Mosaic Virus / drug effects*

Substances

  • Antineoplastic Agents, Phytogenic
  • Antiviral Agents
  • Drugs, Chinese Herbal
  • Limonins
  • munronin A