Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity.

Abstract:

:Phytoalexins are inducible chemical defenses produced by plants in response to diverse forms of stress, including microbial attack. Our search for phytoalexins from cruciferous plants resistant to economically important fungal diseases led us to examine stinkweed or pennycress (Thlaspi arvense), a potential source of disease resistance to blackleg. We have investigated phytoalexin production in leaves of T. arvense under abiotic (copper chloride) and biotic elicitation by Leptosphaeria maculans (Desm.) Ces. et de Not. [asexual stage Phoma lingam (Tode ex Fr.) Desm.], and report here two phytoalexins, wasalexin A and arvelexin (4-methoxyindolyl-3-acetonitrile), their syntheses and antifungal activity against isolates of P. lingam/L. maculans, as well as the isolation of isovitexin, a constitutive glycosyl flavonoid of stinkweed, having antioxidant properties but devoid of antifungal activity.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Pedras MS,Chumala PB,Suchy M

doi

10.1016/s0031-9422(03)00441-2

subject

Has Abstract

pub_date

2003-11-01 00:00:00

pages

949-56

issue

5

eissn

0031-9422

issn

1873-3700

pii

S0031942203004412

journal_volume

64

pub_type

杂志文章
  • Transition state analysis of adenosine nucleosidase from yellow lupin (Lupinus luteus).

    abstract::The transition state of adenosine nucleosidase (EC 3.2.2.7) isolated from yellow lupin (Lupinus luteus) was determined based upon a series of heavy atom kinetic isotope effects. Adenosine labeled with 13C, 2H, and 15N was analyzed by liquid chromatography/electrospray mass spectrometry to determine kinetic isotope eff...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.10.006

    authors: Bates C,Kendrick Z,McDonald N,Kline PC

    更新日期:2006-01-01 00:00:00

  • Five labdane diterpenoids from the seeds of Aframomum zambesiacum.

    abstract::Five labdane diterpenoids, (3-5), zambesiacolactone A (7) and zambesiacolactone B (8), were isolated from the seeds of Aframomum zambesiacum (Baker) K. Schum., along with five known labdanes and a linear sesquiterpene, nerolidol. Their structures were elucidated by spectroscopic analysis. Their antiplasmodial activity...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.10.015

    authors: Kenmogne M,Prost E,Harakat D,Jacquier MJ,Frédérich M,Sondengam LB,Zèches M,Waffo-Téguo P

    更新日期:2006-03-01 00:00:00

  • An extensive study on the chemical diversity of lipophilic extractives from Eucalyptus globulus wood.

    abstract::Three mature Eucalyptus globulus trees with 40 years of age were studied at three height levels (0%, 35%, and 60% of total tree height) and at three radial regions (sapwood, inner and outer heartwood). The composition of lipophilic extracts was evaluated and an extensive list of 202 compounds was reported for the firs...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112520

    authors: Gominho J,Lourenço A,Marques AV,Pereira H

    更新日期:2020-12-01 00:00:00

  • A bidesmosidic triterpene saponin from Cephalaria transsylvanica.

    abstract::The structure of cephalaria saponin B, isolated from Cephalaria transsylvanica was elucidated as 3-O-([beta-D-xylopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-->2)-beta-D- xylopyranosyl]-[28-O-beta-D-glucopyranosyl])-3beta,23-dihydroxy-12(13)-oleanene-28-oic acid. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(94)00789-v

    authors: Alankuş-Calişkan O,Anil H

    更新日期:1995-04-01 00:00:00

  • The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements.

    abstract::Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixture...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00266-1

    authors: Bülow N,Konig WA

    更新日期:2000-09-01 00:00:00

  • Tumor promoting diterpenes from Euphorbia leuconeura L.

    abstract::Diterpene esters of the phorbol and ingenol types are known to be highly active tumor promoting agents that typically occur in members of the Euphorbiaceae. In the present work, Euphorbia leuconeura, a rare indoor plant, is analyzed for its tumor promoting potential. Latex as well as total leaf extracts exhibited Epst...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00016-3

    authors: Vogg G,Mattes E,Rothenburger J,Hertkorn N,Achatz S,Sandermann H Jr

    更新日期:1999-05-01 00:00:00

  • Structure and antiviral activity of sulfated fucans from Stoechospermum marginatum.

    abstract::A sulfated fucan containing fraction (SmWE) was isolated from water extract of the brown seaweed Stoechospermum marginatum collected from the Arabian Sea. Anion exchange chromatography of the crude fraction results in the production of a sulfated fucan (F3) having a molecular mass of 40 kDa and specific rotation [alph...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.05.024

    authors: Adhikari U,Mateu CG,Chattopadhyay K,Pujol CA,Damonte EB,Ray B

    更新日期:2006-11-01 00:00:00

  • Developments in aspects of ecological phytochemistry: the role of cis-jasmone in inducible defence systems in plants.

    abstract::The challenges and opportunities for protecting agricultural production of food and other materials will be met through exploiting the induction of defence pathways in plants to control pests, diseases and weeds. These approaches will involve processes that can be activated by application of natural products, patented...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2007.09.025

    authors: Pickett JA,Birkett MA,Bruce TJ,Chamberlain K,Gordon-Weeks R,Matthes MC,Napier JA,Smart LE,Woodcock CM

    更新日期:2007-11-01 00:00:00

  • Purification and spectroscopic studies on catechol oxidase from lemon balm (Melissa officinalis).

    abstract::A catechol oxidase from lemon balm (Melissa officinalis) moCO which only catalyzes the oxidation of catechols to quinones without hydroxylating tyrosine was purified. The molecular mass of the M. officinalis enzyme of 39,370 Da was obtained by MALDI mass spectrometry and the isoelectric point was determined to be 3.4....

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2012.05.022

    authors: Rompel A,Büldt-Karentzopoulos K,Molitor C,Krebs B

    更新日期:2012-09-01 00:00:00

  • Defense and signalling metabolites of the crucifer Erucastrum canariense: Synchronized abiotic induction of phytoalexins and galacto-oxylipins.

    abstract::Erucastrum canariense Webb & Berthel. (Brassicaceae) is a wild crucifer that grows in rocky soils, in salt and water stressed habitats, namely in the Canary Islands and similar environments. Abiotic stress induced by copper chloride triggered formation of a phytoalexin and galacto-oxylipins in E. canariense, whereas w...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.03.005

    authors: Pedras MSC,To QH

    更新日期:2017-07-01 00:00:00

  • Saikosaponin derivatives from Bupleurum wenchuanense.

    abstract::From the roots of Bupleurum wenchuanense 14 derivatives of saikosaponin were isolated and identified as 2"-O-beta-D-xylopyranosylsaikosaponin b2, 3",6"-O O-diacetylsaikosaponin b2, 2"-O-beta-D-glucopyranosylsaikosaponin b2, saikosaponin b2, 6"-O-acetylsaikosaponin b2, saikosaponin d, 2"-O-acetylsaikosaponin d, 3"-O-ac...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(93)85049-w

    authors: Luo SQ,Lin LZ,Cordell GA

    更新日期:1993-07-01 00:00:00

  • Dammarane-type saponins from Gynostemma pentaphyllum.

    abstract::Seven dammarane glycosides, gypenosides GC1 to GC7, together with ten known compounds, gypenosides V, XIV, XLII-XLVI, gynosaponins TN-1, -2, and gymnemaside VI, were isolated from the methanol extract of the aerial parts of Gynostemma pentaphyllum. Their structures were elucidated by both analysis of 1D and 2D NMR spe...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.04.003

    authors: Kim JH,Han YN

    更新日期:2011-08-01 00:00:00

  • Acylated flavonol glycosides from leaves of Planchonia grandis.

    abstract::Three acylated flavonol glycosides have been identified from leaves of Planchonia grandis Ridley. They possess kaempferol as aglycone and two triglycosidic chains substituting hydroxyl groups at the 3- and 7-positions. The first glycosidic unit of each chain is esterified by a cis or trans p-coumaric acid. Structural ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(03)00215-2

    authors: Crublet ML,Long C,Sévenet T,Hadi HA,Lavaud C

    更新日期:2003-09-01 00:00:00

  • Ultraviolet-B radiation modifies the quantitative and qualitative profile of flavonoids and amino acids in grape berries.

    abstract::Grapevine cv. Tempranillo fruit-bearing cuttings were exposed to supplemental ultraviolet-B (UV-B) radiation under controlled conditions, in order to study its effect on grape traits, ripening, amino acids and flavonoid profile. The plants were exposed to two doses of UV-B biologically effective (5.98 and 9.66kJm(-2)d...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2014.03.014

    authors: Martínez-Lüscher J,Torres N,Hilbert G,Richard T,Sánchez-Díaz M,Delrot S,Aguirreolea J,Pascual I,Gomès E

    更新日期:2014-06-01 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

  • Anti-tumour-promoting glyceroglycolipids from the green alga, Chlorella vulgaris.

    abstract::Two new monogalactosyl diacylglycerols were isolated from the freshwater green alga, Chlorella vulgaris, as anti-tumour promoters, together with three monogalactosyl diacylglycerols and two digalactosyl diacylglycerols. The new monogalactosyl diacylglycerol containing (7Z,10Z)-hexadecadienoic acid showed a more potent...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(95)00458-j

    authors: Morimoto T,Nagatsu A,Murakami N,Sakakibara J,Tokuda H,Nishino H,Iwashima A

    更新日期:1995-11-01 00:00:00

  • Meroterpenoids with diverse structures and anti-inflammatory activities from Rhododendron anthopogonoides.

    abstract::Eight pairs of meroterpenoid enantiomers and four achiral meroterpenoids were isolated from Rhododendron anthopogonoides Maxim. Seventeen of them, named (+)-/(-)-anthoponoids A-G, (+)-daurichromene D, and anthoponoids H and I, are undescribed compounds with structural diversity. Their structures were characterized her...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2020.112524

    authors: Shi Q,Li TT,Wu YM,Sun XY,Lei C,Li JY,Hou AJ

    更新日期:2020-12-01 00:00:00

  • Ester-type cephalotaxus alkaloids from Cephalotaxus harringtonia var. drupacea.

    abstract::Three alkaloids, neoharringtonine, homoneoharringtonine and 3'S-hydroxyneoharringtonine, were isolated from the leaves and stems of Cephalotaxus harringtonia var. drupacea. Their structures were established by spectroscopic methods, including two-dimensional NMR and CD spectra, and their antileukaemic activity was eva...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(96)00574-2

    authors: Takano I,Yasuda I,Nishijima M,Yanagi Y,Takeya K,Itokawa H

    更新日期:1997-02-01 00:00:00

  • Oleanane-type triterpene oligoglycosides with pancreatic lipase inhibitory activity from the pericarps of Sapindus rarak.

    abstract::The methanolic extract from the pericarps of Sapindus rarak DC. was found to show pancreatic lipase inhibitory activity (IC50=ca. 614 microg/mL). From the extract, oleanane-type triterpene oligoglycosides, rarasaponins I-III (1-3), and raraoside A (4), were isolated together with 13 known saponins and four known sesqu...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.06.015

    authors: Morikawa T,Xie Y,Asao Y,Okamoto M,Yamashita C,Muraoka O,Matsuda H,Pongpiriyadacha Y,Yuan D,Yoshikawa M

    更新日期:2009-06-01 00:00:00

  • Metabolic fate of 3α,5-cycloandrostanes in the endogenous lactonization pathway of Aspergillus tamarii KITA.

    abstract::A series of 3α,5-cycloandrostane analogues with a range of functionality (6α and 6β alcohols and ketone) at carbon 6 were tested in the endogenous lactonization pathway in Aspergillus tamarii KITA. This metabolic route converts progesterone to testololactone in high yield through a four step enzymatic pathway. To date...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.09.003

    authors: Hunter AC,Patel S,Dedi C,Dodd HT,Bryce RA

    更新日期:2015-11-01 00:00:00

  • Converting S-limonene synthase to pinene or phellandrene synthases reveals the plasticity of the active site.

    abstract::S-limonene synthase is a model monoterpene synthase that cyclizes geranyl pyrophosphate (GPP) to form S-limonene. It is a relatively specific enzyme as the majority of its products are composed of limonene. In this study, we converted it to pinene or phellandrene synthases after introducing N345A/L423A/S454A or N345I ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.02.017

    authors: Xu J,Ai Y,Wang J,Xu J,Zhang Y,Yang D

    更新日期:2017-05-01 00:00:00

  • Reassessment of effects on lignification and vascular development in the irx4 Arabidopsis mutant.

    abstract::The Arabidopsis thaliana irregular xylem4 (irx4) cinnamoyl-CoA reductase 1 (CCR1) mutant was reassessed for its purported exclusive rate-limiting or key effects on lignification. Analyses of gross growth characteristics and stem cross-section anatomy, from seedling emergence to senescence, revealed that stunted irx4 m...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.12.016

    authors: Patten AM,Cardenas CL,Cochrane FC,Laskar DD,Bedgar DL,Davin LB,Lewis NG

    更新日期:2005-09-01 00:00:00

  • The phytoalexins from cauliflower, caulilexins A, B and C: isolation, structure determination, syntheses and antifungal activity.

    abstract::Our continuous search for phytoalexins from crucifers led us to examine phytoalexin production in florets of cauliflower (Brassica oleracea var. botrytis) under abiotic (UV light) elicitation. Four known (isalexin, S-(-)-spirobrassinin, 1-methoxybrassitin, brassicanal C) and three new (caulilexins A-C) phytoalexins we...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2006.05.020

    authors: Pedras MS,Sarwar MG,Suchy M,Adio AM

    更新日期:2006-07-01 00:00:00

  • Metabolomic analysis applied to chemosystematics and evolution of megadiverse Brazilian Vernonieae (Asteraceae).

    abstract::Vernonia sensu lato is the largest and most complex genus of the tribe Vernonieae (Asteraceae). The tribe is chemically characterized by the presence of sesquiterpene lactones and flavonoids. Over the years, several taxonomic classifications have been proposed for Vernonia s.l. and for the tribe; however, there has be...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.03.007

    authors: Gallon ME,Monge M,Casoti R,Da Costa FB,Semir J,Gobbo-Neto L

    更新日期:2018-06-01 00:00:00

  • Abietane diterpenoids and triterpenoic acids from Salvia cilicica and their antileishmanial activities.

    abstract::Bioguided-fractionation of an acetone extract of the roots of Salvia cilicica (Lamiaceae) led to isolation of two new diterpenes, 7-hydroxy-12-methoxy-20-nor-abieta-1,5(10),7,9,12-pentaen-6,14-dione and abieta-8,12-dien-11,14-dione (12-deoxy-royleanone), together with oleanolic acid, ursolic acid, ferruginol, inuroyol...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00361-8

    authors: Tan N,Kaloga M,Radtke OA,Kiderlen AF,Oksüz S,Ulubelen A,Kolodziej H

    更新日期:2002-12-01 00:00:00

  • Phytochemistry and pharmacology of the genus Leonurus: The herb to benefit the mothers and more.

    abstract::Plants belonging to the genus Leonurus, also named motherwort, are traditionally used for anti-gynecological disorder in East Asia, and for sedative in Europe. Chemical investigation of the genus Leonurus not only enriched the natural products library, but also enlarged the pharmacological application of this traditio...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.phytochem.2017.12.016

    authors: Zhang RH,Liu ZK,Yang DS,Zhang XJ,Sun HD,Xiao WL

    更新日期:2018-03-01 00:00:00

  • Anti-HIV-1 and anti-HIV-1-protease substances from Ganoderma lucidum.

    abstract::A new highly oxygenated triterpene named ganoderic acid alpha has been isolated from a methanol extract of the fruiting bodies of Ganoderma lucidum together with twelve known compounds. The structures of the isolated compounds were determined by spectroscopic means including 2D-NMR. Ganoderiol F and ganodermanontriol ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(98)00254-4

    authors: el-Mekkawy S,Meselhy MR,Nakamura N,Tezuka Y,Hattori M,Kakiuchi N,Shimotohno K,Kawahata T,Otake T

    更新日期:1998-11-01 00:00:00

  • O-Galloyl-C-glycosylflavones from Pelargonium reniforme.

    abstract::The unique series of C-2''-acylated C-glycosylflavones is extended by the discovery of the C-8-glucosyl derivatives 2''-O-galloylvitexin and 2''-O-galloylorientin and their C-6 analogues 2''-O-galloylisovitexin and 2''-O-galloylisoorientin, representing the first described O-galloyl-C-glycosylflavones. They are accomp...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00403-4

    authors: Latté KP,Ferreira D,Venkatraman MS,Kolodziej H

    更新日期:2002-02-01 00:00:00

  • Current trends in microbial steroid biotransformation.

    abstract::Microbial transformations of various steroids are reviewed. Developmental studies on immobilization of microbial cells, techniques for selective transformation and better yields of desired metabolites are highlighted. The present position of microbial biotechnology in the steroid drug industry and the future prospects...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0031-9422(00)90685-x

    authors: Mahato SB,Majumdar I

    更新日期:1993-11-01 00:00:00

  • Phytotoxins from the fungus Malbranchea aurantiaca.

    abstract::Bioassay-directed fractionation of an ethyl acetate extract from cultures of the fungus Malbranchea aurantiaca led to the isolation of two phytotoxic compounds, namely, 1-hydroxy-2-oxoeremophil-1(10),7(11),8(9)-trien-12(8)-olide (1) and penicillic acid (2). The structure of 1 was established by spectroscopic and X-ray...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2005.03.005

    authors: Martínez-Luis S,González MC,Ulloa M,Mata R

    更新日期:2005-05-01 00:00:00