A new 9,10-dihydrophenanthrene and cell proliferative 3,4-δ-dehydrotocopherols from Stemona tuberosa

Molecules. 2015 Apr 3;20(4):5965-74. doi: 10.3390/molecules20045965.

Abstract

A new compound, 9,10-dihydro-5-methoxy-8-methyl-2,7-phenanthrenediol (1), was isolated from the roots of Stemona tuberosa Lour. (Stemonaceae) together with two new optically active compounds, (2S,4'R,8'R)-3,4-δ-dehydrotocopherol (2) and (2R,4'R,8'R)-3,4-δ-dehydrotocopherol (3). The structures of compounds 1-3 were determined on the basis of spectroscopic data analysis. Compounds 2 and 3 were each purified from a stereoisomeric mixture of 2 and 3 by preparative HPLC using a chiral column for the first time. The absolute configurations at C-2 of 2 and 3 were determined by Circular Dichroism (CD) experiments. As a part of the research to find natural wound healing agents, all isolates and the mixture of 2 and 3 were evaluated for their cell proliferative effects using a mouse fibroblast NIH3T3 and a HeLa human cervical cancer cell line. As a result, 1, 2, 3, or the mixture of 2 and 3 showed 41.6%, 78.4%, 118.6%, 38.2% increases of cell proliferation in the mouse fibroblast NIH3T3 respectively, compared to 28.4% increase of δ-tocopherol. Moreover, none of them induced cancer cell proliferation. Therefore, 3,4-δ-dehydrotocopherols, especially pure isomers 2 and 3 can be suggested as potential wound healing agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Proliferation / drug effects
  • HeLa Cells
  • Humans
  • Mice
  • Molecular Structure
  • NIH 3T3 Cells
  • Phenanthrenes / chemistry*
  • Phenanthrenes / isolation & purification
  • Phenanthrenes / pharmacology*
  • Plant Roots / chemistry
  • Stemonaceae / chemistry*
  • Tocopherols / chemistry*
  • Tocopherols / isolation & purification
  • Tocopherols / pharmacology*

Substances

  • Phenanthrenes
  • Tocopherols