Novel nitric oxide and superoxide generation inhibitors, persenone A and B, from avocado fruit

Oe Kyung Kim, Akira Murakami, Yoshimasa Nakamura, Naohito Takeda, Hideo Yoshizumi, Hajime Ohigashi

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

One known, (2R)-(12Z,15Z)-2-hydroxy-4-oxoheneicosa-12,15-dien-1-yl acetate (1), and two novel compounds, persenone A (2) and B (3), have been isolated from avocado fruit (Persea americana P. Mill), as inhibitors of superoxide (O2-) and nitric oxide (NO) generation in cell culture systems. They showed marked inhibitory activities toward NO generation induced by lipopolysaccharide in combination with interferon-γ in mouse macrophage RAW 264.7 cells. Their inhibitory potencies of NO generation (1, IC50 = 3.6; 2, IC50 = 1.2; and 3, IC50 = 3.5 μM) were comparable to or higher than that of a natural NO generation inhibitor, docosahexaenoic acid (DHA; IC50 = 4.3 μM). Furthermore, compounds 1-3 and DHA markedly suppressed tumor promoter 12-O-tetradecanoylphorbol-13-acetate-induced O2--generation in differentiated human promyelocytic HL-60 cells (1, IC50 = 33.7; 2, IC50 = 1.4; 3, IC50 = 1.8; and DHA, IC50 = 10.3 μM). It is notable that they were found to be suppressors of both NO- and O2--generating biochemical pathways but not to be radical scavengers. The results indicate that these compounds are unique antioxidants, preferentially suppressing radical generation, and thus may be promising as effective chemopreventive agent candidates in inflammation-associated carcinogenesis.

Original languageEnglish
Pages (from-to)1557-1563
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume48
Issue number5
DOIs
Publication statusPublished - May 2000
Externally publishedYes

Fingerprint

Persea
avocados
Fruits
Superoxides
superoxide anion
Inhibitory Concentration 50
nitric oxide
inhibitory concentration 50
Fruit
Nitric Oxide
fruits
Acetates
Docosahexaenoic Acids
Macrophages
Cell culture
Carcinogens
Interferons
acetates
Lipopolysaccharides
Persea americana

Keywords

  • Avocado
  • Cancer chemoprevention
  • HL-60 cells
  • Nitric oxide
  • RAW 264.7 cells
  • Superoxide

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

Cite this

Novel nitric oxide and superoxide generation inhibitors, persenone A and B, from avocado fruit. / Kim, Oe Kyung; Murakami, Akira; Nakamura, Yoshimasa; Takeda, Naohito; Yoshizumi, Hideo; Ohigashi, Hajime.

In: Journal of Agricultural and Food Chemistry, Vol. 48, No. 5, 05.2000, p. 1557-1563.

Research output: Contribution to journalArticle

Kim, Oe Kyung ; Murakami, Akira ; Nakamura, Yoshimasa ; Takeda, Naohito ; Yoshizumi, Hideo ; Ohigashi, Hajime. / Novel nitric oxide and superoxide generation inhibitors, persenone A and B, from avocado fruit. In: Journal of Agricultural and Food Chemistry. 2000 ; Vol. 48, No. 5. pp. 1557-1563.
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