New Stilbenoids from Peanut (Arachis hypogaea) Seeds Challenged by an Aspergillus caelatus Strain

Соболев, В. С.; Neff, Scott A.; Gloer, James B.

doi:10.1021/jf802891v

Cited by 66 publications

(120 citation statements)

References 28 publications

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“…The flow rate was 8.0 mL/min. 17 Chiricanine A, 6, was prepared as described 17 ( Figure 1). O-Methyl sterigmatocystin was purchased from Cayman Chemical (Ann Arbor, MI), and a certified solution of combined aflatoxins B 1 , 7; B 2 , 8; G 1 , 9; and G 2 , 10, was purchased from Supelco (Bellefonte, PA).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Suppression of Aflatoxin Production in Aspergillus Species by Selected Peanut (Arachis hypogaea) Stilbenoids

Соболев

Arias

Goodman

et al. 2017

J. Agric. Food Chem.

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Aspergillus flavus is a soil fungus that commonly invades peanut seeds and often produces carcinogenic aflatoxins. Under favorable conditions, the fungus-challenged peanut plant produces and accumulates resveratrol and its prenylated derivatives in response to such an invasion. These prenylated stilbenoids are considered peanut antifungal phytoalexins. However, the mechanism of peanut−fungus interaction has not been sufficiently studied. We used pure peanut stilbenoids arachidin-1, arachidin-3, and chiricanine A to study their effects on the viability of and metabolite production by several important toxigenic Aspergillus species. Significant reduction or virtually complete suppression of aflatoxin production was revealed in feeding experiments in A. flavus, Aspergillus parasiticus, and Aspergillus nomius. Changes in morphology, spore germination, and growth rate were observed in A. flavus exposed to the selected peanut stilbenoids. Elucidation of the mechanism of aflatoxin suppression by peanut stilbenoids could provide strategies for preventing plant invasion by the fungi that produce aflatoxins.

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Section: ■ Materials and Methodsmentioning

confidence: 99%

Suppression of Aflatoxin Production in Aspergillus Species by Selected Peanut (Arachis hypogaea) Stilbenoids

Соболев

Arias

Goodman

et al. 2017

J. Agric. Food Chem.

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“…A natural defense of peanut seeds is the production of phytoalexins, which varies in the diversity of compounds produced and their relative quantities depending on the maturity of the seeds and environmental conditions [58][59][60][61] , and it is particularly higher in embryos compared to cotyledons 62 . Embryos also have significantly higher concentrations of nucleic acids, both DNA and RNA than the cotyledons (Arias R.S., unpublished).…”

Section: Discussionmentioning

confidence: 99%

RNAi-mediated Control of Aflatoxins in Peanut: Method to Analyze Mycotoxin Production and Transgene Expression in the Peanut/<em>Aspergillus</em> Pathosystem

Arias

Dang

Соболев

2015

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Citation: Arias, R.S., Dang, P.M., Sobolev, V.S. RNAi-mediated Control of Aflatoxins in Peanut: Method to Analyze Mycotoxin Production and Transgene Expression in the Peanut/Aspergillus Pathosystem. J. Vis. Exp. (106), e53398, doi:10.3791/53398 (2015). AbstractThe Food and Agriculture Organization of the United Nations estimates that 25% of the food crops in the world are contaminated with aflatoxins. That represents 100 million tons of food being destroyed or diverted to non-human consumption each year. Aflatoxins are powerful carcinogens normally accumulated by the fungi Aspergillus flavus and A. parasiticus in cereals, nuts, root crops and other agricultural products. Silencing of five aflatoxin-synthesis genes by RNA interference (RNAi) in peanut plants was used to control aflatoxin accumulation following inoculation with A. flavus. Previously, no method existed to analyze the effectiveness of RNAi in individual peanut transgenic events, as these usually produce few seeds, and traditional methods of large field experiments under aflatoxin-conducive conditions were not an option. In the field, the probability of finding naturally contaminated seeds is often 1/100 to 1/1,000. In addition, aflatoxin contamination is not uniformly distributed. Our method uses few seeds per transgenic event, with small pieces processed for real-time PCR (RT-PCR) or small RNA sequencing, and for analysis of aflatoxin accumulation by ultra-performance liquid chromatography (UPLC). RNAi-expressing peanut lines 288-72 and 288-74, showed up to 100% reduction (p≤0.01) in aflatoxin B 1 and B 2 compared to the control that accumulated up to 14,000 ng . This protocol describes the application of RNAi-mediated control of aflatoxins in transgenic peanut seeds and methods for its evaluation. We believe that its application in breeding of peanut and other crops will bring rapid advancement in this important area of science, medicine and human nutrition, and will significantly contribute to the international effort to control aflatoxins, and potentially other mycotoxins in major food crops.

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“…Interestingly, oxyresveratrol and prenylated oxyresveratrol reported in the bark of Artocarpus dadah (Su et al, 2002) along with pinosylvin isolated from pine (Pinus spp.) hardwood have not been identified in any peanut tissue, while the prenylated product of pinosylvin, chiricanine A, that was first described in the roots of Lonchocarpus chiricanus (Ioset et al, 2001), has been described in peanut seeds after infection with the fungus A. flavus (Sobolev et al, 2009).…”

Section: Substrate Specificity Of Resveratrol Prenyltransferasementioning

confidence: 99%

A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

et al. 2016

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Prenylated stilbenoids synthesized in some legumes exhibit plant pathogen defense properties and pharmacological activities with potential benefits to human health. Despite their importance, the biosynthetic pathways of these compounds remain to be elucidated. Peanut (Arachis hypogaea) hairy root cultures produce a diverse array of prenylated stilbenoids upon treatment with elicitors. Using metabolic inhibitors of the plastidic and cytosolic isoprenoid biosynthetic pathways, we demonstrated that the prenyl moiety on the prenylated stilbenoids derives from a plastidic pathway. We further characterized, to our knowledge for the first time, a membrane-bound stilbenoid-specific prenyltransferase activity from the microsomal fraction of peanut hairy roots. This microsomal fraction-derived resveratrol 4-dimethylallyl transferase utilizes 3,3-dimethylallyl pyrophosphate as a prenyl donor and prenylates resveratrol to form arachidin-2. It also prenylates pinosylvin to chiricanine A and piceatannol to arachidin-5, a prenylated stilbenoid identified, to our knowledge, for the first time in this study. This prenyltransferase exhibits strict substrate specificity for stilbenoids and does not prenylate flavanone, flavone, or isoflavone backbones, even though it shares several common features with flavonoid-specific prenyltransferases.

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New Stilbenoids from Peanut (Arachis hypogaea) Seeds Challenged by an Aspergillus caelatus Strain

Cited by 66 publications

References 28 publications

Suppression of Aflatoxin Production in Aspergillus Species by Selected Peanut (Arachis hypogaea) Stilbenoids

Suppression of Aflatoxin Production in Aspergillus Species by Selected Peanut (Arachis hypogaea) Stilbenoids

RNAi-mediated Control of Aflatoxins in Peanut: Method to Analyze Mycotoxin Production and Transgene Expression in the Peanut/<em>Aspergillus</em> Pathosystem

A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

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