Isolation and Identification of Acetylenic Spiroketal Enol Ethers from Artemisia lactiflora as Inhibitors of Superoxide Generation induced by a Tumor Promoter in Differentiated HL-60 Cells

Yoshimasa Nakamura, Yoshimi Ohto, Akira Murakami, Suratwadee Jiwajinda, Hajime Ohigashi

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Six acetylenic compounds were isolated from the leaves of Artemisia lactiflora (Compositae), an edible plant of Thailand. Four of them were identified as the stereoisomers of 3,4-epoxy-2-(2,4-hexadiynylidene)-l,6-dioxaspiro[4.5]decane and its derivatives, whose planar structures have already been reported. The other two were identified as novel chlorohydrin derivatives of the corresponding diacetylene spiroketal enol ethers. The inhibitory effects of the polyacetylenes isolated in the present study together with genistein on TPA-induced O2- generation were examined. It was revealed that an acyloxyl group at the C-2 position enhanced the inhibitory effect, while the absolute configurations at C-5, -6, and -7 were not important. While polyacetylenes are known to possess several biological roles in various ecosystems, we first found inhibitory effects of the diacetylenes on TPA-induced O2- generation in differentiated HL-60 cells.

Original languageEnglish
Pages (from-to)5031-5036
Number of pages6
JournalJournal of agricultural and food chemistry
Volume46
Issue number12
Publication statusPublished - Dec 1 1998
Externally publishedYes

Keywords

  • Artemisia lactiflora
  • Cancer chemoprevention
  • Diacetylene spiroketal enol ether
  • HL-60
  • Superoxide
  • Tumor promoter

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

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