Maysin, a Flavone Glycoside from Corn Silks with Antibiotic Activity Toward Corn Earworm13

Waiss, Anthony C.; Chan, Bock G.; Elliger, Carl A.; Wiseman, B. R.; McMillian, W. W.; Widstrom, N. W.; Zubér, M. S.; Keaster, Armon J.

doi:10.1093/jee/72.2.256

Cited by 157 publications

(96 citation statements)

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“…However, P1-rr a1 pericarps are brown (Meyers, 1927) and accumulate significant levels of C-glycosyl flavones (Styles and Ceska, 1989), suggesting the potential of this organ to form flavones. By contrast, P1-rr silks accumulate large quantities of C-glycosyl flavones (Waiss et al, 1979;Wiseman et al, 1993;Byrne et al, 1996a;McMullen et al, 2001), with little or no accumulation of apigenin or luteolin. We identified here a maize enzyme capable of converting naringenin or eriodictyol into the corresponding 2-hydroxyflavanones (Figure 4), which are then expected to serve as substrates for C-glycosylation, followed by dehydration and formation of the corresponding C-glycosyl flavones (Figure 1).…”

Section: P1 Controlled Genes Fill a Key Step In The Biosynthesis Of Imentioning

confidence: 99%

A Genome-Wide Regulatory Framework Identifies Maize Pericarp Color1 Controlled Genes

Morohashi¹,

et al. 2012

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Pericarp Color1 (P1) encodes an R2R3-MYB transcription factor responsible for the accumulation of insecticidal flavones in maize (Zea mays) silks and red phlobaphene pigments in pericarps and other floral tissues, which makes P1 an important visual marker. Using genome-wide expression analyses (RNA sequencing) in pericarps and silks of plants with contrasting P1 alleles combined with chromatin immunoprecipitation coupled with high-throughput sequencing, we show here that the regulatory functions of P1 are much broader than the activation of genes corresponding to enzymes in a branch of flavonoid biosynthesis. P1 modulates the expression of several thousand genes, and ;1500 of them were identified as putative direct targets of P1. Among them, we identified F2H1, corresponding to a P450 enzyme that converts naringenin into 2-hydroxynaringenin, a key branch point in the P1-controlled pathway and the first step in the formation of insecticidal C-glycosyl flavones. Unexpectedly, the binding of P1 to gene regulatory regions can result in both gene activation and repression. Our results indicate that P1 is the major regulator for a set of genes involved in flavonoid biosynthesis and a minor modulator of the expression of a much larger gene set that includes genes involved in primary metabolism and production of other specialized compounds.

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Section: P1 Controlled Genes Fill a Key Step In The Biosynthesis Of Imentioning

confidence: 99%

A Genome-Wide Regulatory Framework Identifies Maize Pericarp Color1 Controlled Genes

Morohashi¹,

et al. 2012

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“…Chief among them is damage by the lepidopteran maize earworm (CEW, Helicoverpa zea Boddie), responsible for significant grain losses in the US. CEW destruction starts when the newly hatched larvae start feeding on silks, the elongated stigmas on the female flower, until they reach the ear and continue to feed on kernels (Waiss et al, 1979). Antibiosis to CEW is primarily provided by maysin [299-Oa-rhamnosyl-6-C-(6-deoxy-xylo-hexos-4-ulosyl)luteolin] (Waiss et al, 1979), a C-glycosyl flavone with strong feeding deterrent effects, first characterized from the Mexican maize landrace Zapalote Chico (Elliger, 1980;Wiseman et al, 1992;Snook, 1998a, 1998b).…”

Section: Introductionmentioning

confidence: 99%

Identification and Characterization of Maize salmon silks Genes Involved in Insecticidal Maysin Biosynthesis

et al. 2016

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The century-old maize (Zea mays) salmon silks mutation has been linked to the absence of maysin. Maysin is a C-glycosyl flavone that, when present in silks, confers natural resistance to the maize earworm (Helicoverpa zea), which is one of the most damaging pests of maize in America. Previous genetic analyses predicted Pericarp Color1 (P1; R2R3-MYB transcription factor) to be epistatic to the sm mutation. Subsequent studies identified two loci as being capable of conferring salmon silks phenotypes, salmon silks1 (sm1) and sm2. Benefitting from available sm1 and sm2 mapping information and from knowledge of the genes regulated by P1, we describe here the molecular identification of the Sm1 and Sm2 gene products. Sm2 encodes a rhamnosyl transferase (UGT91L1) that uses isoorientin and UDP-rhamnose as substrates and converts them to rhamnosylisoorientin. Sm1 encodes a multidomain UDP-rhamnose synthase (RHS1) that converts UDP-glucose into UDP-Lrhamnose. Here, we demonstrate that RHS1 shows unexpected substrate plasticity in converting the glucose moiety in rhamnosylisoorientin to 4-keto-6-deoxy glucose, resulting in maysin. Both Sm1 and Sm2 are direct targets of P1, as demonstrated by chromatin immunoprecipitation experiments. The molecular characterization of Sm1 and Sm2 described here completes the maysin biosynthetic pathway, providing powerful tools for engineering tolerance to maize earworm in maize and other plants.

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“…To date, several flavonoids, such as maysin, apigmaysin, and 3-methoxymaysine, ax-4-OH-maysin, among others, have been isolated and identified from corn silk (Waiss et al 1979;Snook et al 1995;Ren et al 2009). Recently, the authors successfully isolated and identified five flavones glycosides from corn silk, including 2''-o-α-l-rhamnosyl-6-C-3''-deoxyglucosyl-3'-methoxyluteolin (Compound I), ax-5''-methane-3'-methoxymaysin (Compound II), ax-4''-OH-3'-methoxymaysin (Compound III), 6,4'-dihydroxy-3'-methoxyflavone-7-o-glucoside (Compound IV), and 7,4'-dihydroxy-3'-methoxyflavone-2"-o-α-l-rhamnosyl-6-C-fucoside (Compound V) (Figure 1) (Yi et al 1997).…”

mentioning

confidence: 99%

Antioxidative activity of five flavones glycosides from corn silk (Stigma maydis)

Ren¹,

Qiao²,

Xiao-lin³

2013

Czech J. Food Sci.

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Maysin, a Flavone Glycoside from Corn Silks with Antibiotic Activity Toward Corn Earworm13

Cited by 157 publications

References 0 publications

A Genome-Wide Regulatory Framework Identifies Maize Pericarp Color1 Controlled Genes

A Genome-Wide Regulatory Framework Identifies Maize Pericarp Color1 Controlled Genes

Identification and Characterization of Maize salmon silks Genes Involved in Insecticidal Maysin Biosynthesis

Antioxidative activity of five flavones glycosides from corn silk (Stigma maydis)

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