A modified high-performance liquid chromatographic (HPLC) method for determination of trans-resveratrol (resveratrol) in peanuts and peanut products has been developed. Resveratrol was extracted with acetonitrile-water (90/10, v/v) by blending with diatomaceous earth at high speed followed by purification of an aliquot of the extract on a minicolumn packed with Al(2)O(3)-ODS (C(18)) mixture. The column was eluted with acetonitrile-water (90/10, v/v), eluate was evaporated under nitrogen, and residue was dissolved in HPLC mobile phase. Resveratrol in an aliquot of purified extract was quantitated by HPLC on silica gel with n-hexane-2-propanol-water-acetonitrile-acetic acid (1050/270/17/5/1, v/v) as a mobile phase. The recovery of resveratrol added to diatomaceous earth at 0.05 microg/g was 98.95 +/- 17.79%; the recovery of the standard added to fresh peanuts (with 0.070 microg/g natural level of resveratrol) at 0.50, 5.00, and 10.00 microg/g was 117.23 +/- 8.87, 100.10 +/- 2.49, and 100.45 +/- 1.51%, respectively. The quantitation limit of resveratrol in fresh peanuts was about 0. 01 microg/g. Roasted peanuts had the lowest content of resveratrol of 0.055 +/- 0.023 microg/g (n = 21), while in peanut butter its concentration was significantly higher, 0.324 +/- 0.129 microg/g (n = 46), and boiled peanuts had the highest level of 5.138 +/- 2.849 microg/g (n = 12). Resveratrol content in commercial peanut products was similar to the resveratrol content of the raw peanut fractions routinely used for making them.

Four new stilbene derivatives, termed arahypins, have been isolated from peanut seeds challenged by an Aspergillus caelatus strain, along with two known stilbenoids that have not been previously reported in peanuts. The structures of these new putative phytoalexins were determined by analysis of NMR, MS, and UV data. Together with other known peanut stilbenoids that were also produced in the challenged seeds, these new compounds may play a defensive role against invasive fungi.

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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A new pigmented, optically active, low molecular weight metabolite has been isolated from peanut (Arachis hypogaea) kernels challenged by four species of Aspergillus. The structure of the new compound, termed SB-1, was elucidated by analysis of 1H NMR, 13C NMR, and mass spectrometric data. The SB-1 molecule bears prenylated benzenoid and but-2-enolide moieties and represents an unusual class of compounds. The closest known analogue to SB-1 was isolated from heartwood of Pericopsis elata. Both A. hypogaea and P. elata belong to the family Leguminosae. The new metabolite was accumulated in different peanut genotypes challenged by five Aspergillus species and may be an important representative of a new class of peanut phytoalexins. SB-1 production often exceeds production of major known stilbenes.

A liquid chromatographic (LC) method for determination of stilbene phytoalexins (SPs) in peanuts has been developed. SPs were extracted with acetonitrile–water (90 + 10, v/v) by high-speed blending. An aliquot of extract was applied to a minicolumn packed with AI2O3–ODS (C18) mixture and eluted with acetonitrile-water (90 + 10, v/v). Eluate was evaporated under nitrogen, and residue was dissolved in LC mobile phase. SPs in an aliquot of purified extract were quantitated by normal-phase partition LC on silica gel with n-heptane–2-propanol–water–acetonitrile–acetic acid (1050 + 270 + 17 + 5 + 1, v/v) as mobile phase. Recoveries of SPs [frans-4-(3-methyl-but-1-enyl)-3,5,4′-trihy-droxystilbene (trans-arachidin-3; t-Ar-3), trans-3-isopentadienyl-4,3′,5′-trihydroxystilbene (t-IPD), and trans-3,5,4′-trihydroxystilbene (trans-resveratrol; t-Res)] from peanuts spiked at 300 ppb were 96.05 ± 2.8%. Limits of quantitation for t-Ar-3 and t-IPD were about 100 ppb. t-Ar-3, t-IPD, and t-Res were found in all parts of the peanut plant as major SPs produced in response to fungal invasion.

Aspergillus flavus is the major producer of carcinogenic aflatoxins worldwide in crops. Populations of A. flavus are characterized by high genetic variation and the source of this variation is likely sexual reproduction. The fungus is heterothallic and laboratory crosses produce ascospore-bearing ascocarps embedded within sclerotia. However, the capacity for sexual reproduction in sclerotia naturally formed in crops has not been examined. Corn was grown for 3 years under different levels of drought stress at Shellman, GA, and sclerotia were recovered from 146 ears (0.6% of ears). Sclerotia of A. flavus L strain were dominant in 2010 and 2011 and sclerotia of A. flavus S strain were dominant in 2012. The incidence of S strain sclerotia in corn ears increased with decreasing water availability. Ascocarps were not detected in sclerotia at harvest but incubation of sclerotia on the surface of nonsterile soil in the laboratory resulted in the formation of viable ascospores in A. flavus L and S strains and in homothallic A. alliaceus. Ascospores were produced by section Flavi species in 6.1% of the 6,022 sclerotia (18 of 84 ears) in 2010, 0.1% of the 2,846 sclerotia (3 of 36 ears) in 2011, and 0.5% of the 3,106 sclerotia (5 of 26 ears) in 2012. For sexual reproduction to occur under field conditions, sclerotia may require an additional incubation period on soil following dispersal at crop harvest.