Tannins in plant-herbivore interactions.

Abstract:

:Tannins are the most abundant secondary metabolites made by plants, commonly ranging from 5% to 10% dry weight of tree leaves. Tannins can defend leaves against insect herbivores by deterrence and/or toxicity. Contrary to early theories, tannins have no effect on protein digestion in insect herbivores. By contrast, in vertebrate herbivores tannins can decrease protein digestion. Tannins are especially prone to oxidize in insects with high pH guts, forming semiquinone radicals and quinones, as well as other reactive oxygen species. Tannin toxicity in insects is thought to result from the production of high levels of reactive oxygen species. Tannin structure has an important effect on biochemical activity. Ellagitannins oxidize much more readily than do gallotannins, which are more oxidatively active than most condensed tannins. The ability of insects to tolerate ingested tannins comes from a variety of biochemical and physical defenses in their guts, including surfactants, high pH, antioxidants, and a protective peritrophic envelope that lines the midgut. Most work on the ecological roles of tannins has been correlative, e.g., searching for negative associations between tannins and insect performance. A greater emphasis on manipulative experiments that control tannin levels is required to make further progress on the defensive functions of tannins. Recent advances in the use of molecular methods has permitted the production of tannin-overproducing transgenic plants and a better understanding of tannin biosynthetic pathways. Many research areas remain in need of further work, including the effects of different tannin types on different types of insects (e.g., caterpillars, grasshoppers, sap-sucking insects).

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Barbehenn RV,Peter Constabel C

doi

10.1016/j.phytochem.2011.01.040

subject

Has Abstract

pub_date

2011-09-01 00:00:00

pages

1551-65

issue

13

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(11)00069-0

journal_volume

72

pub_type

杂志文章,评审
  • Triterpene glycosides from Schefflera octophylla.

    abstract::In addition to 3-epi-betulinic acid, three triterpene glycosides were isolated from leaves of Schefflera octophylla. The structures of the glycosides have been determined as 28-O-[alpha-L-rhamnopyranosyl(1----4)-O-beta-D-glucopyranosyl(1----6)-be ta-D- glucopyranosides of 3 alpha-hydroxy-lup-20(29)-ene-23,28-dioic aci...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(91)83647-4

    authors: Sung TV,Steglich W,Adam G

    更新日期:1991-01-01 00:00:00

  • Cardiac glycosides from Yellow Oleander (Thevetia peruviana) seeds.

    abstract::Thevetia cardiac glycosides can lead to intoxication, thus they are important indicators for forensic and pharmacologic surveys. Six thevetia cardiac glycosides, including two with unknown structures, were isolated from the seeds of the Yellow Oleander (Thevetia peruviana (Pers.) K. Shum., Apocynaceae). LC-ESI⁺-MS(/MS...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2011.11.019

    authors: Kohls S,Scholz-Böttcher BM,Teske J,Zark P,Rullkötter J

    更新日期:2012-03-01 00:00:00

  • Megastigmane and iridoid glucosides from Clerodendrum inerme.

    abstract::From the aerial parts of Clerodendrum inerme, two megastigmane glucosides (sammangaosides A and B) and a iridoid glucoside (sammangaoside C) were isolated together with 15 known compounds. The structural elucidations were based on analyses of physical and spectroscopic data. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00208-4

    authors: Kanchanapoom T,Kasai R,Chumsri P,Hiraga Y,Yamasaki K

    更新日期:2001-09-01 00:00:00

  • Coumaronochromones and flavanones from Euchresta formosana roots.

    abstract::Four coumaronochromones, formosanatins A-D (-4), and a flavanone, euchrenone a(16), along with four known compounds, euchretins E and G, euchrestaflavanone A, and daidzein, were isolated from the roots of Euchresta formosana. The structures of - were established by spectroscopic analyses. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00017-1

    authors: Lo WL,Chang FR,Hsieh TJ,Wu YC

    更新日期:2002-08-01 00:00:00

  • Isolation of steroidal glycoalkaloids from Solanum incanum by two countercurrent chromatographic methods.

    abstract::Using a bioassay for inhibition of plant growth and a combination of two countercurrent chromatographies: rotation locular countercurrent chromatography and droplet countercurrent chromatography, two biologically active glycosidal alkaloids, solasonine and solamargine were isolated from fresh ripe fruit of Solanum inc...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(91)83753-8

    authors: Fukuhara K,Kubo I

    更新日期:1991-01-01 00:00:00

  • Phenylethanoid glycosides of Sesamum indicum.

    abstract::From a water extract of whole plants of Sesamum indicum, two new, and six known phenylethanoid glycosides, and three new triglycosides which had the same sugar sequence were isolated. The structures of the new compounds were elucidated from chemical and spectroscopic evidence. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(93)85348-u

    authors: Suzuki N,Miyase T,Ueno A

    更新日期:1993-10-01 00:00:00

  • Oleanane triterpenes with protein tyrosine phosphatase 1B inhibitory activity from aerial parts of Lantana camara collected in Indonesia and Japan.

    abstract::During the search for new protein tyrosine phosphatase (PTP) 1B inhibitors, EtOH extracts from the aerial parts of Lantana camara L. (lantana) collected at Manado (Indonesia) and two subtropical islands in Japan (Ishigaki and Iriomote Islands, Okinawa) exhibited potent inhibitory activities against PTP1B in an enzyme ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2017.08.020

    authors: Abdjul DB,Yamazaki H,Maarisit W,Rotinsulu H,Wewengkang DS,Sumilat DA,Kapojos MM,Losung F,Ukai K,Namikoshi M

    更新日期:2017-12-01 00:00:00

  • Substrate specificity in phospholipid transformations by plant phospholipase D isoenzymes.

    abstract::Phospholipase D (PLD) catalyzes the hydrolysis and transesterification of glycerophospholipids at the terminal phosphodiester bond. In many plants, several isoforms of PLD have been identified without knowing their functional differences. In this paper, the specificities of two PLD isoenzymes from white cabbage (Brass...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.01.011

    authors: Dippe M,Ulbrich-Hofmann R

    更新日期:2009-02-01 00:00:00

  • Chalcones and other constituents of Dorstenia prorepens and Dorstenia zenkeri.

    abstract::The twigs of Dorstenia prorepens furnished the digeranylated chalcone, 5,3'-(3,7-dimethyl-2,6-octadienyl)-3,4, 2',4'-tetrahydroxychalcone while Dorstenia zenkeri yielded the 3',4'-(3-hydroxy-2,2-dimethyldihydropyrano)-4,2'-dihydroxychalcone and a bichalcone. 4-Hydroxylonchocarpin was found in both plants. D. prorepens...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00483-6

    authors: Abegaz BM,Ngadjui BT,Dongo E,Ngameni B,Nindi MN,Bezabih M

    更新日期:2002-04-01 00:00:00

  • Biosynthesis of tetrahydroanthraquinones in fungi.

    abstract::The tetrahydroanthraquinones (1S,3S)-austrocortilutein (4) and (1S,3S)-austrocortirubin (7) are octaketides formed in the fruit bodies of the fungus Dermocybe splendida via the gentiobioside 2 of the dihydroanthracenone (S)-torosachrysone (1). ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00181-3

    authors: Elsworth C,Gill M,Saubern S

    更新日期:2000-09-01 00:00:00

  • Gentisic acid conjugates of Medicago truncatula roots.

    abstract::Three phenolic glycosides 5-O-{[5''-O-E-(4'''-O-threo-guaiacylglycerol)-feruloyl]-beta-apiofuranosyl-(1-->2)-beta-xylopyranosyl} gentisic acid, 5-O-[(5''-O-vanilloyl)-beta-apiofuranosyl-(1-->2)-beta-xylopyranosyl] gentisic acid and 1-O-[E-(4'''-O-threo-guaiacylglycerol)-feruloyl]-3-O-beta-galacturonopyranosyl glycerol...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2009.07.021

    authors: Stochmal A,Kowalska I,Janda B,Perrone A,Piacente S,Oleszek W

    更新日期:2009-07-01 00:00:00

  • Triterpenoids and their glycosides from the bark of Schefflera octophylla.

    abstract::A new triterpene and its glycosides were isolated from the bark of Schefflera octophylla together with asiatic acid and asiaticoside. Based on spectroscopic data, especially 2DNMR, and chemical transformations the structures of the new compounds were determined as 3 alpha-hydroxy-urs-12-ene-23,28-dioic acid and 3 alph...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(91)83042-j

    authors: Sung TV,Lavaud C,Porzel A,Steglich W,Adam G

    更新日期:1992-01-01 00:00:00

  • Xanthones from Hypericum roeperanum.

    abstract::Four new xanthones have been isolated from the roots of Hypericum roeperanum. Their structures have been established by a combination of spectroscopic and chemical methods as 1,6-dihydroxy-5-methoxy-4',5'-dihydro-4',4',5'-trimethylfurano- (2',3':3,4)-xanthone (5-O-methyl-2-deprenylrheediaxanthone B), 1,6-dihydroxy-5-m...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/0031-9422(96)00284-1

    authors: Rath G,Potterat O,Mavi S,Hostettmann K

    更新日期:1996-09-01 00:00:00

  • Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and O-Methyltransferase.

    abstract::Carrot (Daucus carota subsp. sativus) is a widely cultivated root vegetable of high economic importance. The aroma of carrot roots and aboveground organs is mainly defined by terpenes. We found that leaves of orange carrot cultivar also produce considerable amounts of the phenylpropenes methyleugenol and methylisoeuge...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2018.12.020

    authors: Yahyaa M,Berim A,Nawade B,Ibdah M,Dudareva N,Ibdah M

    更新日期:2019-03-01 00:00:00

  • A new triterpenoid from the fern Adiantum lunulatum and evaluation of antibacterial activity.

    abstract::A new triterpenoid, 22,29xi-epoxy-30-norhopane-13beta-ol (1) was isolated together with six known compounds viz., fern-9(11)-en-6alpha-ol. fern-9(11)-ene, fern-9(11)-en-25-oic acid, fern-9(11)-en-28-ol, filicenol-B, adiantone and oxidation product of fern-9(11)-en-6alpha-ol obtained as 6-oxofern-9(11)-ene from the who...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00334-4

    authors: Reddy VL,Ravikanth V,Rao TP,Diwan PV,Venkateswarlu Y

    更新日期:2001-01-01 00:00:00

  • Distribution of flavonoids in the Myristicaceae.

    abstract::During the past two decades the study of the Myristicaceae species has increased, and many flavonoids of different types have been isolated. This review discusses the flavonoids presently known in the Myristicaceae. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0031-9422(00)00114-x

    authors: Valderrama JC

    更新日期:2000-11-01 00:00:00

  • On the propensity of lignin to associate: a size exclusion chromatography study with lignin derivatives isolated from different plant species.

    abstract::Despite evidence that lignin associates under both aqueous and organic media, the magnitude and nature of the underlying driving forces are still a matter of discussion. The present paper addresses this issue by examining both solution properties and size exclusion behaviour of lignins isolated from five different spe...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.05.026

    authors: Guerra A,Gaspar AR,Contreras S,Lucia LA,Crestini C,Argyropoulos DS

    更新日期:2007-10-01 00:00:00

  • Protein phosphorylation in Nicotiana tabacum cells in response to perception of lipopolysaccharides from Burkholderia cepacia.

    abstract::Bacterial LPS have the ability to act as modulators of the innate immune response in plants. Complex and largely unresolved perception systems exist for LPS on the plant cell surfaces that lead to the activation of multiple intracellular defense signaling pathways. The aim of the present study was to investigate the p...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.09.005

    authors: Gerber IB,Dubery IA

    更新日期:2004-11-01 00:00:00

  • Deoxyarteannuin B, dihydro-deoxyarteannuin B and trans-5-hydroxy-2-isopropenyl-5-methylhex-3-en-1-ol from Artemisia anuua.

    abstract::The amorphane sesquiterpenes, deoxyarteannuin B and dihydro-deoxyarteannuin B, were isolated from Artemisia annua and their structures mainly determined by two-dimensional NMR spectoscopic analyses. The irregular monoterpene, trans-5-hydroxy-2-isopropenyl-5-methylhex-3-en-1-ol, was also characterized in the same way, ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00358-2

    authors: Sy LK,Brown GD

    更新日期:2001-12-01 00:00:00

  • Antitumor sterols from the mycelia of Cordyceps sinensis.

    abstract::Activity guided fractionations led to the isolation of two antitumor compounds 5 alpha,8 alpha-epidioxy-24(R)-methylcholesta-6,22-dien-3 beta-D-glucopyranoside and 5,6-epoxy-24(R)-methylcholesta-7,22-dien-3 beta-ol from the methanol extract of Cordyceps sinensis. Two previously known compounds, ergosteryl-3-O-beta-D-g...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00128-4

    authors: Bok JW,Lermer L,Chilton J,Klingeman HG,Towers GH

    更新日期:1999-08-01 00:00:00

  • NMR studies of molecular structure in fruit cuticle polyesters.

    abstract::The cuticle of higher plants functions primarily as a protective barrier for the leaves and fruits, controlling microbial attack as well as the diffusion of water and chemicals from the outside environment. Its major chemical constituents are waxes (for waterproofing) and cutin (a structural support polymer). However,...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(01)00106-6

    authors: Fang X,Qiu F,Yan B,Wang H,Mort AJ,Stark RE

    更新日期:2001-07-01 00:00:00

  • Galactan sulfate of Grateloupia indica: Isolation, structural features and antiviral activity.

    abstract::Natural compounds offer interesting pharmacological perspectives for antiviral drug development with regard to broad-spectrum antiviral properties and novel modes of action. In this study, we have analyzed polysaccharide fractions isolated from Grateloupia indica. The crude water extract (GiWE) as well as one fraction...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2007.02.008

    authors: Chattopadhyay K,Mateu CG,Mandal P,Pujol CA,Damonte EB,Ray B

    更新日期:2007-05-01 00:00:00

  • Characterisation of the willow phenylalanine ammonia-lyase (PAL) gene family reveals expression differences compared with poplar.

    abstract::Willow is an important biomass crop for the bioenergy industry, and therefore optimal growth with minimal effects of biotic and abiotic stress is essential. The phenylpropanoid pathway is responsible for the biosynthesis of not only lignin but also of flavonoids, condensed tannins, benzenoids and phenolic glycosides w...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2015.06.005

    authors: de Jong F,Hanley SJ,Beale MH,Karp A

    更新日期:2015-09-01 00:00:00

  • Odd-numbered very-long-chain polyunsaturated fatty acids from the dinoflagellate Amphidinium carterae identified by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry.

    abstract::A method is described for the enrichment of odd very-long-chain polyunsaturated fatty acids (VLCPUFAs) by means of RP-HPLC and argentation TLC from total fatty acids of the dinoflagellate A. carterae and their identification as picolinyl esters by means of microbore liquid chromatography-mass spectrometry with atmosph...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2008.08.021

    authors: Rezanka T,Nedbalová L,Sigler K

    更新日期:2008-11-01 00:00:00

  • 5-Lipoxygenase-derived oxylipins from the red alga Rhodymenia pertusa.

    abstract::The lipid extract of the temperate red alga Rhodymenia pertusa has yielded four eicosanoid metabolites, three of which are new natural products. Using principally NMR and MS techniques, their structures were deduced as 5R,6S-dihydroxy-7(E),9(E),11(Z),14(Z)-eicosatetraenoic acid (5R,6S-diHETE), 5R*,6S*-dihydroxy-7(E),9...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(99)00445-8

    authors: Jiang ZD,Ketchum SO,Gerwick WH

    更新日期:2000-01-01 00:00:00

  • Kaempferol triosides from Reseda muricata.

    abstract::A flavonoid trioside and its coumaryl ester together with seven known flavonoids and five phenolic acids were isolated from the leaves of Reseda muricata. Their structures were elucidated by spectroscopic methods including UV, FAB MS, 1H, 13C and 2D-NMR, DEPT, HMBC and HMQC experiments. The two compounds were identifi...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(00)00479-9

    authors: El-Sayed NH,Omara NM,Yousef AK,Farag AM,Mabry TJ

    更新日期:2001-06-01 00:00:00

  • A chlorinated coumarinolignan from the African medicinal plant, Mondia whitei.

    abstract::The unusual chlorinated coumarinolignan, 5-chloropropacin, along with several other known compounds have been isolated from the roots of Mondia whitei. The structure of the chlorinated coumarinolignan was determined by NMR and mass spectroscopic analyses. ...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2004.11.012

    authors: Patnam R,Kadali SS,Koumaglo KH,Roy R

    更新日期:2005-03-01 00:00:00

  • Thomitrems A and E, two indole-alkaloid isoprenoids from Penicillium crustosum Thom.

    abstract::Two indole-alkaloid isoprenoids were isolated from extracts of Penicillium crustosum Thom grown on rice. Their structures were elucidated on the basis of various NMR experiments and by comparison to the structurally related penitrems. The two compounds, designated thomitrem A and thomitrem E, contain a 18(19)-double b...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/s0031-9422(02)00369-2

    authors: Rundberget T,Wilkins AL

    更新日期:2002-12-01 00:00:00

  • 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

  • Potential sources of high value chemicals from leaves, stems and flowers of Miscanthus sinensis 'Goliath' and Miscanthus sacchariflorus.

    abstract::Society demands chemicals from sustainable sources. Identification of commercially important chemicals in crops increases value in biorefineries and reduces reliance on petrochemicals. Miscanthus sinensis and Miscanthus sacchariflorus are high-yielding distinct plants, which are sources of high-value chemicals and bio...

    journal_title:Phytochemistry

    pub_type: 杂志文章

    doi:10.1016/j.phytochem.2013.04.004

    authors: Parveen I,Wilson T,Donnison IS,Cookson AR,Hauck B,Threadgill MD

    更新日期:2013-08-01 00:00:00