Identification of phenylamide phytoalexins and characterization of inducible phenylamide metabolism in wheat.

Abstract:

:Changes in specialized metabolites were analyzed in wheat leaves inoculated with Bipolaris sorokiniana, the causal agent of spot blotch of Poaceae species. HPLC analysis detected the accumulation of six compounds in B. sorokiniana-infected leaves. Of these, we purified two compounds by silica gel and ODS column chromatography and preparative HPLC, and identified them as cinnamic acid amides, N-cinnamoyl-9-hydroxy-8-oxotryptamine and N-cinnamoyl-8-oxotryptamine, by spectroscopic analyses. The remaining four compounds were predicted to be p-coumaric acid amides of hydroxyputrescine, hydroxyagmatine, hydroxydehydroagmatine, and agmatine by mass spectrometry. The accumulation of two cinnamic acid amides was also induced by Fusarium graminearum infection, and by treatment with CuCl2, jasmonic acid, and isopentenyladenine. Antifungal activity of these amides was shown by inhibition of conidial germination and germ tube elongation of F. graminearum and Alternaria brassicicola, indicating that they act as phytoalexins. The accumulation of these amides also detected in barley leaves treated with CuCl2. We examined the accumulation of 25 phenylamides in B. sorokiniana-infected wheat leaves using LC-MS/MS. Hydroxycinnamic acid amides of tryptamine, serotonin, putrescine, and agmatine, were induced after infection with B. sorokiniana. Thus, the induced accumulation of two groups of phenylamides, cinnamic acid amides with indole amines, and p-coumaric acid amides with putrescine and agmatine related amines, represents a major metabolic response of wheat to pathogen infection.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Ube N,Harada D,Katsuyama Y,Osaki-Oka K,Tonooka T,Ueno K,Taketa S,Ishihara A

doi

10.1016/j.phytochem.2019.112098

subject

Has Abstract

pub_date

2019-11-01 00:00:00

pages

112098

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(19)30414-5

journal_volume

167

pub_type

杂志文章
  • Triterpene saponins from Eryngium kotschyi.

    abstract::Four new oleanane-type saponins 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyl-22-O-β,β-dimethylacryloylA1-barrigenol (1), 3-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucuronopyranosyl-22-O-angeloylA1-barrigenol (2), 3-O-β-D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 6)]-β-D-glucopyranosyl-21,22,28-O-triacetyl-(...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.11.017

    authors: Aslan Erdem S,Mitaine-Offer AC,Miyamoto T,Kartal M,Lacaille-Dubois MA

    更新日期:2015-02-01 00:00:00

  • p-coumaric acid esters from Tanacetum longifolium.

    abstract::Two new long chain alkyl p-coumaric acid esters (2-3) along with eicosanyl trans-p-coumarate (1) were isolated from chloroform extract of the roots of Tanacetum longifolium. The structures of new compounds were assigned as 21'-hydroxyheneicosanyl-4-hydroxy-(cis and trans) p-coumarate (2a, 2b) and 27'-hydroxy heptacosa...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2003.08.023

    authors: Mahmood U,Kaul VK,Acharya R,Jirovetz L

    更新日期:2003-10-01 00:00:00

  • Oxytrofalcatins A-F, N-benzoylindole analogues from the roots of Oxytropis falcata (Leguminosae).

    abstract::Indole alkaloids, oxytrofalcatins A-F (1-6), together with five other known alkaloids (7-11), were isolated from the roots of Oxytropis falcata. Their structures were elucidated by comprehensive spectroscopic analyses, including using 1D and 2D NMR spectroscopy and mass spectrometry. This is the first report of N-benz...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2010.02.010

    authors: Chen WH,Wu QX,Wang R,Shi YP

    更新日期:2010-06-01 00:00:00

  • Biosynthesis of the dimethylallyl moiety of glabrol in Glycyrrhiza glabra hairy root cultures via a non-mevalonate pathway.

    abstract::Incorporation of [1-13C]glucose indicates that the biosynthesis of the hemiterpene moiety of glabrol, the main prenylated flavanone in the hairy root cultures of Glycyrrhiza glabra, proceeds via a glyceraldehyde/pyruvate non-mevalonate pathway. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00327-7

    authors: Asada Y,Li W,Yoshikawa T

    更新日期:2000-10-01 00:00:00

  • Aromatic compounds produced by Periconia atropurpurea, an endophytic fungus associated with Xylopia aromatica.

    abstract::6,8-Dimethoxy-3-(2'-oxo-propyl)-coumarin (1) and 2,4-dihydroxy-6-[(1'E,3'E)-penta-1',3'-dienyl]-benzaldehyde (2), in addition to the known compound periconicin B (3), were isolated from the ethyl acetate extract of Periconia atropurpurea, an endophytic fungus obtained from the leaves of Xylopia aromatica, a native pla...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.09.005

    authors: Teles HL,Sordi R,Silva GH,Castro-Gamboa I,Bolzani Vda S,Pfenning LH,de Abreu LM,Costa-Neto CM,Young MC,Araújo AR

    更新日期:2006-12-01 00:00:00

  • Solar UV-B radiation modulates chemical defenses against Anticarsia gemmatalis larvae in leaves of field-grown soybean.

    abstract::Although it is well known that solar ultraviolet B (UV-B) radiation enhances plant defenses, there is less knowledge about traits that define insect resistance in field-grown soybean. Here we study the effects of solar UV-B radiation on: a) the induction of phenolic compounds and trypsin proteinase inhibitors (TPI) in...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.05.006

    authors: Dillon FM,Chludil HD,Zavala JA

    更新日期:2017-09-01 00:00:00

  • Secondary mould metabolites of Cladosporium tenuissimum, a hyperparasite of rust fungi.

    abstract::Investigation of the extracts of a culture of Cladosporium tenuissimum, a known hyperparasite of several rust fungi, gave rise to the isolation of cladosporols B-E (2-5). Their structure and stereochemistry were elucidated on the basis of 1H and 13C NMR evidence and CD measures. Cladosporols 1-5 were active in inhibit...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.03.013

    authors: Nasini G,Arnone A,Assante G,Bava A,Moricca S,Ragazzi A

    更新日期:2004-07-01 00:00:00

  • Cytosolic ascorbate peroxidase 2 (cAPX 2) is involved in the soybean response to flooding.

    abstract::Proteomic analyses of soybean seedlings responding to flooding were conducted to identify key proteins involved. The seeds were germinated on a spongy matrix for two days, and then subjected to flooding for three days. After flooding, the total number of roots, the length of the main root, the lengths of the lateral a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.01.007

    authors: Shi F,Yamamoto R,Shimamura S,Hiraga S,Nakayama N,Nakamura T,Yukawa K,Hachinohe M,Matsumoto H,Komatsu S

    更新日期:2008-04-01 00:00:00

  • Corynanthean, eburnan, secoleuconoxine, and pauciflorine alkaloids from Kopsia pauciflora.

    abstract::Eleven indole alkaloids, comprising four corynanthean, two eburnane, one aspidofractinine, one secoleuconoxine, one andranginine, and two pauciflorine type alkaloids were isolated from the stem-bark and leaf extracts of Kopsia pauciflora. Their structures were determined using NMR and MS analyses. The catharinensine t...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.09.014

    authors: Gan CY,Yoganathan K,Sim KS,Low YY,Lim SH,Kam TS

    更新日期:2014-12-01 00:00:00

  • Xylogalacturonan exists in cell walls from various tissues of Arabidopsis thaliana.

    abstract::Evidence is presented for the presence of xylogalacturonan (XGA) in Arabidopsis thaliana. This evidence was obtained by extraction of pectin from the seeds, root, stem, young leaves and mature leaves of A. thaliana, followed by treatment of these pectin extracts with xylogalacturonan hydrolase (XGH). Upon enzymatic tr...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.01.016

    authors: Zandleven J,Sørensen SO,Harholt J,Beldman G,Schols HA,Scheller HV,Voragen AJ

    更新日期:2007-04-01 00:00:00

  • Phenylpropanoid glucosides from Chrozophora obliqua.

    abstract::From the aerial parts of Chrozophora obliqua, two phenylpropanoid glucosides: 4-O-methyl guaiacylglycerol 9-O-beta-glucopyranoside (1) and 4-O-methyl guaiacylglycerol 8-O-beta-glucopyranoside (2) together with syringin, benzyl alcohol glucoside, isorhamnetin-3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and quer...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00262-x

    authors: Mohamed KM

    更新日期:2001-10-01 00:00:00

  • Sesquiterpene lactones from Elephantopus mollis and their anti-inflammatory activities.

    abstract::Seven sesquiterpene lactones, 8-O-methacryloylelephanpane, 2,4-bis-O-methyl-8-O-methacryloylelephanpane, 4-O-ethyl-8-O-methacryloylelephanpane, 8-O-methacryloylisoelephanpane, 2-O-demethyltomenphantopin C, molephantin A, molephantin B, along with ten known ones, were isolated from Elephantopus mollis (Asteraceae). The...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.01.020

    authors: Wu ZN,Zhang YB,Chen NH,Li MJ,Li MM,Tang W,Zhuang L,Li YL,Wang GC

    更新日期:2017-05-01 00:00:00

  • Steroidal saponins from the leaves of Cordyline stricta.

    abstract::Three new spirostanol saponins and two new furostanol saponins were isolated from the fresh leaves of Cordyline stricta. Their structures were elucidated on the basis of spectroscopic analysis, including various 2D NMR techniques, hydrolysis, and by comparison of spectral data of known compounds. Two of the isolated s...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(97)00545-1

    authors: Mimaki Y,Kuroda M,Takaashi Y,Sashida Y

    更新日期:1998-01-01 00:00:00

  • Acylated triterpene saponins from Silene jenisseensis.

    abstract::From the roots of Silene jenisseensis a new trans-p-methoxycinnamoyl triterpene saponin has been isolated along with its cis-p-methoxycinnamoyl isomer as an inseparable mixture. Their structures were established by chemical means and spectroscopic methods including 1D- and 2D-homonuclear and heteronuclear correlation ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00222-s

    authors: Lacaille-Dubois MA,Hanquet B,Cui ZH,Lou ZC,Wagner H

    更新日期:1995-09-01 00:00:00

  • Occurrence and characterization of oils rich in gamma-linolenic acid (III): the taxonomical value of the fatty acids in Echium (Boraginaceae).

    abstract::Fourteen species of the genus Echium (Fam. Boraginaceae) collected in the Macaronesia were surveyed in a search for high levels of gamma-linolenic acid (GLA, 18:3omega6) in the seed oil. High amounts of this fatty acid were found in all of them, ranging from 18.85% (E. pitardii var. pitardii) to 27.42% (E. gentianoide...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00184-4

    authors: Guil-Guerrero JL,Gómez-Mercado F,Rodríguez-García I,Campra-Madrid P,García-Maroto F

    更新日期:2001-09-01 00:00:00

  • Jubanines F-J, cyclopeptide alkaloids from the roots of Ziziphus jujuba.

    abstract::Five Ib-type cyclopeptide alkaloids, jubanines F-J (1-5), and three known compounds, nummularine B (6), daechuine-S3 (7), and mucronine K (8) were isolated from the roots of Ziziphus jujuba. Their structures were fully characterized by spectroscopic analyses in combination with chemical derivatization. Compounds 1-3, ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.09.001

    authors: Kang KB,Ming G,Kim GJ,Ha TK,Choi H,Oh WK,Sung SH

    更新日期:2015-11-01 00:00:00

  • nor-Lignans from the leaves of Styrax ferrugineus (Styracaceae) with antibacterial and antifungal activity.

    abstract::Chemical examination of the leaves of Styrax ferrugineus yielded 5-[3''-(beta-D-glucopyranosyloxy)propyl]-7-methoxy-2-(3',4'-dimethoxyphenyl) benzofuran, along with the known nor-lignans 5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-methylenedioxyphenyl) benzofuran, 5-(3''-hydroxypropyl)-7-methoxy-2-(3',4'-dimethoxyphenyl)...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00225-9

    authors: Pauletti PM,Araújo AR,Young MC,Giesbrecht AM,Bolzani VD

    更新日期:2000-11-01 00:00:00

  • Steroidal glycosides and cardenolide glycosides from Asclepias fruticosa.

    abstract::Asclepias fruticosa afforded, in addition to five known pregnane glycosides and 11 known cardenolide glycosides, four new pregnane glycosides and eleven new cardenolide glycosides. Structures of these compounds were elucidated by spectroscopic methods and from chemical evidence. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(94)85029-1

    authors: Warashina T,Noro T

    更新日期:1994-09-01 00:00:00

  • Euphane triterpenoids of Cassipourea lanceolata from the Madagascar rainforest.

    abstract::Fractionation of an ethanol extract of a Madagascar collection of the leaves and fruit of Cassipourea lanceolata Tul. led to the isolation of three euphane triterpenoids 1-3. The (1)H and (13)C NMR spectra of all compounds were fully assigned using a combination of 2D NMR experiments, including COSY, TOCSY, HSQC (HMQC...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.12.009

    authors: Hou Y,Cao S,Brodie PJ,Miller JS,Birkinshaw C,Andrianjafy MN,Andriantsiferana R,Rasamison VE,TenDyke K,Shen Y,Suh EM,Kingston DG

    更新日期:2010-04-01 00:00:00

  • Dissection of the network of indolic defence compounds in Arabidopsis thaliana by multiple mutant analysis.

    abstract::Characteristic for cruciferous plants is the synthesis of a complex array of defence-related indolic compounds. In Arabidopsis, these include indol-3-ylmethyl glucosinolates (IMGs), as well as stress-inducible indole-3-carbaldehyde (ICHO)/indole-3-carboxylic acid (ICOOH) derivatives and camalexin. Key enzymes in the b...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2019.01.009

    authors: Müller TM,Böttcher C,Glawischnig E

    更新日期:2019-05-01 00:00:00

  • A triterpenoid saponin from Phytolacca esculenta.

    abstract::A new triterpenoid saponin, 3-O-[beta-D-glucopyranosyl(1----4)-beta-D- xylopyranosyl]-28-O-beta-D-glucopyranosyl-30-methyloleanate-9(11), 12-dien- 2,3,23-trihydroxyl-28-oic acid, was isolated from the roots of Phytolacca esculenta. The structure was assigned by chemical methods and spectral analysis (1H, 13C, DEPT NMR...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(92)83327-u

    authors: Yi YH

    更新日期:1992-07-01 00:00:00

  • The configuration of methyl jasmonate affects paclitaxel and baccatin III production in Taxus cells.

    abstract::All stereoisomers of methyl jasmonate (MJA) were prepared, and their effects on cell yield and promotion of paclitaxel (Taxol) and baccatin III production investigated in cell suspension cultures of Taxus media. (3R,7S)-MJA showed the strongest cell growth inhibition, followed by (3R,7R)-MJA. In contrast, (3S,7R)- and...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00006-6

    authors: Yukimune Y,Hara Y,Nomura E,Seto H,Yoshida S

    更新日期:2000-05-01 00:00:00

  • Antigenotoxic prenylated flavonoids from stem bark of Erythrina latissima.

    abstract::A series of prenylated flavonoids was obtained from antigenotoxic extracts and fractions of stem bark of Erythrina latissima E. Mey (Leguminosae). In addition to five constituents never reported before, i.e. (2S)-5,7-dihydroxy-2-(4-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-6-yl)chroman-4-one (erylatissin D), (2...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.06.003

    authors: Zarev Y,Foubert K,Lucia de Almeida V,Anthonissen R,Elgorashi E,Apers S,Ionkova I,Verschaeve L,Pieters L

    更新日期:2017-09-01 00:00:00

  • Phosphoproteins analysis in plants: a proteomic approach.

    abstract::The study of phosphoproteome on a global scale represents one of the challenges in the post-genomic era. Here, we propose an integrated procedure starting from the crude protein extract, that consists of sequential purification steps, and ending up in the identification of phosphorylation sites. This involves (i) an e...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.07.010

    authors: Laugesen S,Messinese E,Hem S,Pichereaux C,Grat S,Ranjeva R,Rossignol M,Bono JJ

    更新日期:2006-10-01 00:00:00

  • A bidesmosidic triterpene glycoside from the roots of Symphytum officinale.

    abstract::A new bidesmosidic triterpenoidal saponin of hederagenin was isolated from the ethanolic extract of the roots of Symphytum officinale L. Its structure was elucidated by using 1H NMR, 1H-1H COSY NMR, heteronuclear 1H-13C correlated spectroscopy (heteroCOSY), 13C NMR, DEPT, FAB mass spectrometry and chemical evidence as...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)97091-2

    authors: Noorwala M,Mohammad FV,Ahmad VU,Sener B

    更新日期:1994-05-01 00:00:00

  • Hemicellulosic polysaccharides from bamboo shoot cell-walls.

    abstract::Cell-wall polysaccharides of bamboo shoots were extracted with chelating reagent (CDTA, trans-1,2-cyclohexanediamine-N,N,N',N'-tetraacetic acid), Na(2)CO(3) and KOH solutions. Glycosyl composition and glycosyl linkage analyses showed that the hemicellulose was composed of arabinoxylan, (1-->3, 1-->4)-beta-D-glucan, xy...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00237-4

    authors: Edashige Y,Ishii T

    更新日期:1998-11-20 00:00:00

  • Neolignan and flavonoid glycosides in Juniperus communis var. depressa.

    abstract::Two neolignan glycosides (junipercomnosides A and B) were isolated from aerial parts of Juniperus communis var. depressa along with two known neolignan glycosides and seven flavonoid glycosides. The structures of the isolated compounds were determined by spectral analysis, in particular by 2D-NMR analysis. The signifi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2003.10.025

    authors: Nakanishi T,Iida N,Inatomi Y,Murata H,Inada A,Murata J,Lang FA,Iinuma M,Tanaka T

    更新日期:2004-01-01 00:00:00

  • Bioactive terpenoids from sunflower leaves cv. Peredovick.

    abstract::The CH(2)Cl(2) extract of dried leaves of Helianthus annuus L. cv. Peredovick(R) has yielded, in addition to the known sesquiterpene lactones annuolide E and leptocarpin, and the sesquiterpenes heliannuols A, C, D, F, G, H, I, the new bisnorsesquiterpene, annuionone E, and the new sesquiterpenes heliannuol L, helibisa...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00370-9

    authors: Macías FA,Torres A,Galindo JL,Varela RM,Alvarez JA,Molinillo JM

    更新日期:2002-11-01 00:00:00

  • Hypoglycemic triterpenes from Gynostemma pentaphyllum.

    abstract::To search for bioactive gypenosides and their analogues, a saponin enriched fraction and its hydrolyzate from Gynostemma pentaphyllum were phytochemically investigated. Fractionation by diverse chromatographic methods, including HPLC, Sephadex LH-20, silica gel, and C18 reverse phase silica gel, led to the isolation a...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.08.008

    authors: Wang J,Ha TKQ,Shi YP,Oh WK,Yang JL

    更新日期:2018-11-01 00:00:00

  • Mechanisms of survival of necrotrophic fungal plant pathogens in hosts expressing the hypersensitive response.

    abstract::The hypersensitive response (HR), elicited when resistant hosts are infected by incompatible races of biotrophic fungi, has been researched extensively. New studies on host responses to necrotrophic fungi are beginning to show that when the HR occurs in hosts colonized by necrotrophs, fungal growth is accelerated rath...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0031-9422(01)00187-x

    authors: Mayer AM,Staples RC,Gil-ad NL

    更新日期:2001-09-01 00:00:00