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. 2011 Mar 9;59(5):1673-82.
doi: 10.1021/jf104742n. Epub 2011 Feb 11.

Biological activity of peanut (Arachis hypogaea) phytoalexins and selected natural and synthetic Stilbenoids

Victor S Sobolev  1 , Shabana I Khan, Nurhayat Tabanca, David E Wedge, Susan P Manly, Stephen J Cutler, Monique R Coy, James J Becnel, Scott A Neff, James B Gloer
Affiliations

Biological activity of peanut (Arachis hypogaea) phytoalexins and selected natural and synthetic Stilbenoids

Victor S Sobolev et al. J Agric Food Chem. .

Abstract

The peanut plant (Arachis hypogaea L.), when infected by a microbial pathogen, is capable of producing stilbene-derived compounds that are considered antifungal phytoalexins. In addition, the potential health benefits of other stilbenoids from peanuts, including resveratrol and pterostilbene, have been acknowledged by several investigators. Despite considerable progress in peanut research, relatively little is known about the biological activity of the stilbenoid phytoalexins. This study investigated the activities of some of these compounds in a broad spectrum of biological assays. Since peanut stilbenoids appear to play roles in plant defense mechanisms, they were evaluated for their effects on economically important plant pathogenic fungi of the genera Colletotrichum, Botrytis, Fusarium, and Phomopsis. We further investigated these peanut phytoalexins, together with some related natural and synthetic stilbenoids (a total of 24 compounds) in a panel of bioassays to determine their anti-inflammatory, cytotoxic, and antioxidant activities in mammalian cells. Several of these compounds were also evaluated as mammalian opioid receptor competitive antagonists. Assays for adult mosquito and larvae toxicity were also performed. The results of these studies reveal that peanut stilbenoids, as well as related natural and synthetic stilbene derivatives, display a diverse range of biological activities.

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Figures

Figure 1
Figure 1
Structures of tested compounds. *Peanut phytoalexins. **Other natural plant stilbenoids. O-Glc refers to a glucosyl moiety.
Figure 1
Figure 1
Structures of tested compounds. *Peanut phytoalexins. **Other natural plant stilbenoids. O-Glc refers to a glucosyl moiety.
Figure 2
Figure 2
Antifungal properties of peanut phytoalexinsagainst Phomopsis viticola (A) and P. obscurans (B and C). Antifungal properties of tested natural and synthetic stilbenoidsagainst Phomopsis viticola (D), P. obscurans (E), and Botrytis cinerea (F and G).
Figure 3
Figure 3
Affinity of compounds tested to opioid receptors. Compounds 3 and 20 were not tested in this assay due to their insufficient quantity.
Figure 4
Figure 4
Toxicity of compounds tested to mosquito larvae; panel D represents toxicity data for positive and negative standards. UT means Untreated; DMSO means dimethyl sulfoxide. Compound 20 was not tested in this assay due to its insufficient quantity.
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