Lipoxygenase Inhibition by Anadanthoflavone, a New Flavonoid from the Aerial Parts of Anadenanthera colubrina

Maria-Teresa Gutierrez-Lugo; Joshua D. Deschamps; Theodore R. Holman; Enrique Suarez; Barbara N. Timmermann

doi:10.1055/s-2004-818920

Planta Medica, Inhaltsverzeichnis

Planta Med 2004; 70(3): 263-265
DOI: 10.1055/s-2004-818920

Letter

Lipoxygenase Inhibition by Anadanthoflavone, a New Flavonoid from the Aerial Parts of Anadenanthera colubrina

Maria-Teresa Gutierrez-Lugo¹ , Joshua D. Deschamps² , Theodore R. Holman² , Enrique Suarez³ , Barbara N. Timmermann¹

¹Department of Pharmacology and Toxicology, Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Arizona, Tucson, Arizona, U.S.A.
²Department of Chemistry and Biochemistry, University of California, Santa Cruz, California, U.S.A.
³INTA, Instituto Nacional de Recursos Biológicos, Castellar, Buenos Aires, Argentina

This study was supported by the ICBG ”Bioactive Agents from Dryland Biodiversity of Latin America” grant 5 UO1 TW 00316-10 from the National Institutes of Health (NIH), The National Science Foundation (NSF) and the US Department of Agriculture (USDA) to B.N.T., NIH-GM56062-06 (T.R.H.), ACS-RPG-00-219-01-CDD (T.R.H.). The contents are solely the responsibilities of the authors and do not necessarily represent the official views of the NIH, NSF or USDA

Abstract

Chemical investigation of the aerial parts of Anadenanthera colubrina led to the isolation of a new flavonoid named anadanthoflavone (1), along with 11 known compounds: alnusenol, lupenone, lupeol, betulinic acid, α-amyrin, β-amyrin, β-sitosterol, stigmasterol, apigenin, 4-hydroxybenzoic acid and cinnamic acid. The isolated compounds were evaluated for their inhibitory activity on human platelet 12-lipoxygenase (12-hLO), human reticulocyte 15-lipoxygenase (15-hLO) and soybean lipoxygenase-1 (15-sLO). Compound 1 was found to be active against 12-hLO and 15-hLO with IC₅₀ values of 13 ± 3 μM and 17 ± 3 μM, respectively. Apigenin selectively inhibited the activity of 15-hLO (IC₅₀ : 4.0 ± 1 μM), while lupenone, lupeol and α-amyrin were found active against 15-sLO (IC₅₀ : 22 ± 3 μM, 35 ± 9 μM and 15 ± 3 μM, respectively).

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References

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Barbara N. Timmermann, Ph. D.

Department of Pharmacology and Toxicology

Division of Medicinal and Natural Products Chemistry

College of Pharmacy

University of Arizona

1703 E. Mabel Street

Tucson

Arizona 85721-0207

U.S.A.

Telefon: +1-520-626-2481

Fax: +1-520-626-2515

eMail: btimmer@pharmacy.arizona.edu