Inhibition of lipoxygenase and prostaglandin endoperoxide synthase by anacardic acids

Richard Grazzini, David Hesk, Ellen Heininger, George Hildenbrandt, C. Channa Reddy, Diana Lynn Cox-foster, June Medford, Richard Craig, Ralph O. Mumma

Research output: Contribution to journalArticle

71 Citations (Scopus)

Abstract

C22:1 ω5-anacardic acid was found to be a good inhibitor of both potato lipoxygenase and ovine prostaglandin endoperoxide synthase with approximate IC50's of 6 and 27 μM, respectively. Very similar inhibition was seen with the crude exudate, rich in ω5-anacardic acids, from glandular trichomes of an arthropod-resistant strain of geranium, Pelargonium xhortorum. The saturated anacardic acid (C22:0 sat), abundant in the trichome exudate of susceptible strains, was nearly as inhibitory toward both prostaglandin endoperoxide synthase and lipoxygenase as the ω5-unsaturated compound. However, the dimethyl derivative of C22:1 ω5-anacardic acid was a poor inhibitor of prostaglandin endoperoxide synthase and caused only moderate (32%) inhibition of lipoxygenase even at 135 μM. The possible role of prostaglandin endoperoxide synthase and lipoxygenase inhibition in the enhanced pest resistance of geraniums which produce the ω5-AnAs is discussed.

Original languageEnglish (US)
Pages (from-to)775-780
Number of pages6
JournalBiochemical and Biophysical Research Communications
Volume176
Issue number2
DOIs
StatePublished - Apr 30 1991

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Anacardic Acids
Lipoxygenase
Prostaglandin-Endoperoxide Synthases
Trichomes
Exudates and Transudates
Pelargonium
Geranium
Arachidonate 5-Lipoxygenase
Cyclooxygenase Inhibitors
Arthropods
Unsaturated compounds
Solanum tuberosum
Inhibitory Concentration 50
Sheep
Derivatives
anacardic acid

All Science Journal Classification (ASJC) codes

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

Cite this

Grazzini, R., Hesk, D., Heininger, E., Hildenbrandt, G., Reddy, C. C., Cox-foster, D. L., ... Mumma, R. O. (1991). Inhibition of lipoxygenase and prostaglandin endoperoxide synthase by anacardic acids. Biochemical and Biophysical Research Communications, 176(2), 775-780. https://doi.org/10.1016/S0006-291X(05)80252-9
Grazzini, Richard ; Hesk, David ; Heininger, Ellen ; Hildenbrandt, George ; Reddy, C. Channa ; Cox-foster, Diana Lynn ; Medford, June ; Craig, Richard ; Mumma, Ralph O. / Inhibition of lipoxygenase and prostaglandin endoperoxide synthase by anacardic acids. In: Biochemical and Biophysical Research Communications. 1991 ; Vol. 176, No. 2. pp. 775-780.
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abstract = "C22:1 ω5-anacardic acid was found to be a good inhibitor of both potato lipoxygenase and ovine prostaglandin endoperoxide synthase with approximate IC50's of 6 and 27 μM, respectively. Very similar inhibition was seen with the crude exudate, rich in ω5-anacardic acids, from glandular trichomes of an arthropod-resistant strain of geranium, Pelargonium xhortorum. The saturated anacardic acid (C22:0 sat), abundant in the trichome exudate of susceptible strains, was nearly as inhibitory toward both prostaglandin endoperoxide synthase and lipoxygenase as the ω5-unsaturated compound. However, the dimethyl derivative of C22:1 ω5-anacardic acid was a poor inhibitor of prostaglandin endoperoxide synthase and caused only moderate (32{\%}) inhibition of lipoxygenase even at 135 μM. The possible role of prostaglandin endoperoxide synthase and lipoxygenase inhibition in the enhanced pest resistance of geraniums which produce the ω5-AnAs is discussed.",
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Grazzini, R, Hesk, D, Heininger, E, Hildenbrandt, G, Reddy, CC, Cox-foster, DL, Medford, J, Craig, R & Mumma, RO 1991, 'Inhibition of lipoxygenase and prostaglandin endoperoxide synthase by anacardic acids', Biochemical and Biophysical Research Communications, vol. 176, no. 2, pp. 775-780. https://doi.org/10.1016/S0006-291X(05)80252-9

Inhibition of lipoxygenase and prostaglandin endoperoxide synthase by anacardic acids. / Grazzini, Richard; Hesk, David; Heininger, Ellen; Hildenbrandt, George; Reddy, C. Channa; Cox-foster, Diana Lynn; Medford, June; Craig, Richard; Mumma, Ralph O.

In: Biochemical and Biophysical Research Communications, Vol. 176, No. 2, 30.04.1991, p. 775-780.

Research output: Contribution to journalArticle

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AU - Grazzini, Richard

AU - Hesk, David

AU - Heininger, Ellen

AU - Hildenbrandt, George

AU - Reddy, C. Channa

AU - Cox-foster, Diana Lynn

AU - Medford, June

AU - Craig, Richard

AU - Mumma, Ralph O.

PY - 1991/4/30

Y1 - 1991/4/30

N2 - C22:1 ω5-anacardic acid was found to be a good inhibitor of both potato lipoxygenase and ovine prostaglandin endoperoxide synthase with approximate IC50's of 6 and 27 μM, respectively. Very similar inhibition was seen with the crude exudate, rich in ω5-anacardic acids, from glandular trichomes of an arthropod-resistant strain of geranium, Pelargonium xhortorum. The saturated anacardic acid (C22:0 sat), abundant in the trichome exudate of susceptible strains, was nearly as inhibitory toward both prostaglandin endoperoxide synthase and lipoxygenase as the ω5-unsaturated compound. However, the dimethyl derivative of C22:1 ω5-anacardic acid was a poor inhibitor of prostaglandin endoperoxide synthase and caused only moderate (32%) inhibition of lipoxygenase even at 135 μM. The possible role of prostaglandin endoperoxide synthase and lipoxygenase inhibition in the enhanced pest resistance of geraniums which produce the ω5-AnAs is discussed.

AB - C22:1 ω5-anacardic acid was found to be a good inhibitor of both potato lipoxygenase and ovine prostaglandin endoperoxide synthase with approximate IC50's of 6 and 27 μM, respectively. Very similar inhibition was seen with the crude exudate, rich in ω5-anacardic acids, from glandular trichomes of an arthropod-resistant strain of geranium, Pelargonium xhortorum. The saturated anacardic acid (C22:0 sat), abundant in the trichome exudate of susceptible strains, was nearly as inhibitory toward both prostaglandin endoperoxide synthase and lipoxygenase as the ω5-unsaturated compound. However, the dimethyl derivative of C22:1 ω5-anacardic acid was a poor inhibitor of prostaglandin endoperoxide synthase and caused only moderate (32%) inhibition of lipoxygenase even at 135 μM. The possible role of prostaglandin endoperoxide synthase and lipoxygenase inhibition in the enhanced pest resistance of geraniums which produce the ω5-AnAs is discussed.

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