Chemical Constituents of the Style of Zea mays L. with Glycation Inhibitory Activity

Suzuki, Ryuichiro; Iijima, Miki; Okada, Yoshihito; Okuyama, Toru

doi:10.1248/cpb.55.153

Cited by 30 publications

(28 citation statements)

References 22 publications

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“…similarity, a 60-ng sample of compound 12-methyl ester displayed several one-dimensional 1 H-NMR resonances in C 6 D 6 consistent with the aromatic b-macrocarpene derivative previously described as compound 1 (Suzuki et al, 2007 To examine whether zealexins are produced specifically in response to virulent pathogens such as C. graminicola and Cochliobolus heterostrophus or whether they are a more general response to fungi that are not maize stem pathogens such as R. microsporus, Colletotrichum sublineolum, and Aspergillus flavus, inoculated stems were analyzed after 24 h. Exposure to C. heterostrophus, R. microsporus, C. sublineolum, and A. flavus all resulted in accumulation of zealexins A1-3 and B1, whereas inoculation with C. graminicola elicited an attenuated response that was not statistically different from mock inoculation (Fig. 2, A-D).…”

supporting

confidence: 67%

“…We also obtained onedimensional 1 H-NMR data on analyte 12 that is consistent with an additional C2-C3 double bond and C8 alcohol imposed upon zealexin B1, resulting in a skeleton with aromatic and nonaromatic carbon ring systems. While the proposed identity of analyte 12 is tentative, the existence of this structure is certain, as it has been previously isolated and identified from a 30-kg extraction of maize style tissue (Suzuki et al, 2007). Clearly there is additional chemical diversity yet to be discovered within the current analyses and additional maize varieties, tissues, and infection time courses.…”

Section: Discussionmentioning

confidence: 88%

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Novel Acidic Sesquiterpenoids Constitute a Dominant Class of Pathogen-Induced Phytoalexins in Maize

et al. 2011

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Nonvolatile terpenoid phytoalexins occur throughout the plant kingdom, but until recently were not known constituents of chemical defense in maize (Zea mays). We describe a novel family of ubiquitous maize sesquiterpenoid phytoalexins, termed zealexins, which were discovered through characterization of Fusarium graminearum-induced responses. Zealexins accumulate to levels greater than 800 μg g−1 fresh weight in F. graminearum-infected tissue. Their production is also elicited by a wide variety of fungi, Ostrinia nubilalis herbivory, and the synergistic action of jasmonic acid and ethylene. Zealexins exhibit antifungal activity against numerous phytopathogenic fungi at physiologically relevant concentrations. Structural elucidation of four members of this complex family revealed that all are acidic sesquiterpenoids containing a hydrocarbon skeleton that resembles β-macrocarpene. Induced zealexin accumulation is preceded by increased expression of the genes encoding TERPENE SYNTHASE6 (TPS6) and TPS11, which catalyze β-macrocarpene production. Furthermore, zealexin accumulation displays direct positive relationships with the transcript levels of both genes. Microarray analysis of F. graminearum-infected tissue revealed that Tps6/Tps11 were among the most highly up-regulated genes, as was An2, an ent-copalyl diphosphate synthase associated with production of kauralexins. Transcript profiling suggests that zealexins cooccur with a number of antimicrobial proteins, including chitinases and pathogenesis-related proteins. In addition to zealexins, kauralexins and the benzoxazinoid 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one-glucose (HDMBOA-glucose) were produced in fungal-infected tissue. HDMBOA-glucose accumulation occurred in both wild-type and benzoxazine-deficient1 (bx1) mutant lines, indicating that Bx1 gene activity is not required for HDMBOA biosynthesis. Together these results indicate an important cooperative role of terpenoid phytoalexins in maize biochemical defense.

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supporting

confidence: 67%

Section: Discussionmentioning

confidence: 88%

Novel Acidic Sesquiterpenoids Constitute a Dominant Class of Pathogen-Induced Phytoalexins in Maize

et al. 2011

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“…4a-b, Supplementary Fig. 9, Supplementary Table 6) and low levels of the aromatic variant ZC2 29, 46 . As novel compounds ZA5 and ZB3 produce characteristic (EI) spectra (Supplementary Fig.…”

Section: Resultsmentioning

confidence: 99%

Genetic elucidation of complex biochemical traits mediating maize innate immunity

Ding

Weckwerth

Poretsky

et al. 2020

Preprint

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Specialized metabolites constitute key layers of immunity underlying crop resistance; however, challenges in resolving complex pathways limit our understanding of their functions and applications. In maize (Zea mays) the inducible accumulation of acidic terpenoids is increasingly considered as a defense regulating disease resistance. To understand maize antibiotic biosynthesis, we integrated association mapping, pan-genome multi-omic correlations, enzyme structure-function studies, and targeted mutagenesis. We now define ten genes in three zealexin (Zx) gene clusters comprised of four sesquiterpene synthases and six cytochrome P450s that collectively drive the production of diverse antibiotic cocktails. Quadruple mutants blocked in the production of β-macrocarpene exhibit a broad-spectrum loss of disease resistance. Genetic redundancies ensuring pathway resiliency to single null mutations are combined with enzyme substrate-promiscuity creating a biosynthetic hourglass pathway utilizing diverse substrates and in vivo combinatorial chemistry to yield complex antibiotic blends. The elucidated genetic basis of biochemical phenotypes underlying disease resistance demonstrates a predominant maize defense pathway and informs innovative strategies for transferring chemical immunity between crops.

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“…Aus phytochemischer Sicht ist die Droge Maisgriffel durch das Vorkommen von Flavonoiden, Tanninen, Phytosterolen, Chlorogensäure, Allantoin, Vitaminen, Mineralien, Kohlenhydraten und etwas ätherischem Öl gekennzeichnet [15][16][17][18][19]. Das Vorliegen ungewöhnlicher Flavonglykoside, wie etwa Maysin und seinen Derivaten wurde beschrieben [20].…”

Section: Inhaltsstoffeunclassified

Unkomplizierte Harnwegsinfektionen: Extrakte aus Maisgriffeln (Zea mays L.) wirken gegen uropathogene E. coli

Rafsanjany¹,

Sendker²,

Lechtenberg³

et al. 2016

Z Phytother

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Zusammenfassung Die Droge Maisgriffel (Maydis stigmata) aus Zea mays L. wird traditionell zur Behandlung unkomplizierter Infektionen der ableitenden Harnwege eingesetzt. K?rzlich publizierte In-vitro-Untersuchungen aus einem Screening zeigen, dass alkoholische Extrakte aus dieser Droge die Adh?sion uropathogener E. coli (UPEC) an T24-Blasenzellen ?verhindern. Zur genaueren Untersuchung wurden aus 4 unterschiedlichen Chargen Maydis stigmata Ethanol-Wasser (1?:?1)-Ex?trakte hergestellt. Innerhalb eines In-vitro-Adh?sionassays (UPEC-Stamm 2980 und ?humane T24-Blasenzellen) wurde eine konzentrationsabh?ngige antiadh?sive Aktivit?t gegen UPEC best?tigt (IC50 = 1040??g/ml). Eine aktivit?tsgeleitete Fraktionierung an Sephadex LH20 ergab die aktive Fraktion XI, die wiederum mittels MPLC und pr?parativer HPLC weiter aufgetrennt wurde. Dies f?hrte zur Isolierung der Subfraktion XIG, die mittels UHPLC/+ESI-QTOF-MS analysiert wurde. Hieraus resultierte das wahrschein?liche Vorliegen der ungew?hnlichen Flavon-C-glykoside Derhamnosylmaysin, 3?-Deoxyrhamnosylmaysin, 3?-O-Methylderhamnosylmaysin, Apiferol und Alternanthin, f?r die eine Mitbeteiligung an der beobachteten antiadh?siven Wirkung diskutiert werden kann.

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Chemical Constituents of the Style of Zea mays L. with Glycation Inhibitory Activity

Cited by 30 publications

References 22 publications

Novel Acidic Sesquiterpenoids Constitute a Dominant Class of Pathogen-Induced Phytoalexins in Maize

Novel Acidic Sesquiterpenoids Constitute a Dominant Class of Pathogen-Induced Phytoalexins in Maize

Genetic elucidation of complex biochemical traits mediating maize innate immunity

Unkomplizierte Harnwegsinfektionen: Extrakte aus Maisgriffeln (Zea mays L.) wirken gegen uropathogene E. coli

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Chemical Constituents of the Style of Zea mays L. with Glycation Inhibitory Activity

Cited by 30 publications

References 22 publications

Novel Acidic Sesquiterpenoids Constitute a Dominant Class of Pathogen-Induced Phytoalexins in Maize

Novel Acidic Sesquiterpenoids Constitute a Dominant Class of Pathogen-Induced Phytoalexins in Maize

Genetic elucidation of complex biochemical traits mediating maize innate immunity

Unkomplizierte Harnwegsinfektionen: Extrakte aus ­Maisgriffeln (Zea mays L.) wirken gegen uropathogene E. coli

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Product

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Unkomplizierte Harnwegsinfektionen: Extrakte aus Maisgriffeln (Zea mays L.) wirken gegen uropathogene E. coli