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

Yun Seo Kil, Jiyoung Park, Ah Reum Han, Hyun Ae Woo, Eun Kyoung Seo

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

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.

Original languageEnglish
Pages (from-to)5965-5974
Number of pages10
JournalMolecules
Volume20
Issue number4
DOIs
StatePublished - 1 Apr 2015

Keywords

  • 3,4-δ-dehydrotocopherol
  • 9,10-Dihydrophenanthrene
  • Cell proliferation
  • Chiral separation
  • Stemona tuberosa
  • Stemonaceae

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