Green leaf volatiles: biosynthesis, biological functions and their applications in biotechnology.

Plants have evolved numerous constitutive and inducible defence mechanisms to cope with biotic and abiotic stresses. These stresses induce the expression of various genes to activate defence-related pathways that result in the release of defence chemicals. One of these defence mechanisms is the oxylipin pathway, which produces jasmonates, divinylethers and green leaf volatiles (GLVs) through the peroxidation of polyunsaturated fatty acids (PUFAs). GLVs have recently emerged as key players in plant defence, plant-plant interactions and plant-insect interactions. Some GLVs inhibit the growth and propagation of plant pathogens, including bacteria, viruses and fungi. In certain cases, GLVs released from plants under herbivore attack can serve as aerial messengers to neighbouring plants and to attract parasitic or parasitoid enemies of the herbivores. The plants that perceive these volatile signals are primed and can then adapt in preparation for the upcoming challenges. Due to their 'green note' odour, GLVs impart aromas and flavours to many natural foods, such as vegetables and fruits, and therefore, they can be exploited in industrial biotechnology. The aim of this study was to review the progress and recent developments in research on the oxylipin pathway, with a specific focus on the biosynthesis and biological functions of GLVs and their applications in industrial biotechnology.

[1]  M. Holsters,et al.  Nod factor structures, responses, and perception during initiation of nodule development. , 2002, Glycobiology.

[2]  S. Dellaporta,et al.  tasselseed1 Is a Lipoxygenase Affecting Jasmonic Acid Signaling in Sex Determination of Maize , 2009, Science.

[3]  Mats Hamberg,et al.  Diversity of the Enzymatic Activity in the Lipoxygenase Gene Family of Arabidopsis thaliana , 2009, Lipids.

[4]  T. Cheesbrough,et al.  [53] Lipoxygenase from soybeans: EC 1.13.11.12 Linoleate:oxygen oxidoreductase , 1981 .

[5]  C. Langebartels,et al.  Emissions of Oxygenated Volatile Organic Compounds from Plants Part I: Emissions from Lipoxygenase Activity , 2003 .

[6]  M. Hamberg,et al.  Oxylipins Produced by the 9-Lipoxygenase Pathway in Arabidopsis Regulate Lateral Root Development and Defense Responses through a Specific Signaling Cascade[W] , 2007, The Plant Cell Online.

[7]  P. Thonart,et al.  The lipoxygenase metabolic pathway in plants: potential for industrial production of natural green leaf volatiles , 2010 .

[8]  G. Arimura,et al.  Chemical and molecular ecology of herbivore-induced plant volatiles: proximate factors and their ultimate functions. , 2009, Plant & cell physiology.

[9]  Ivo Feussner,et al.  Lipoxygenases - Structure and reaction mechanism. , 2009, Phytochemistry.

[10]  E. Farmer,et al.  Jasmonates and related oxylipins in plant responses to pathogenesis and herbivory. , 2003, Current opinion in plant biology.

[11]  M. Farag,et al.  (Z)-3-Hexenol induces defense genes and downstream metabolites in maize , 2005, Planta.

[12]  K. Goellner,et al.  Priming: it’s all the world to induced disease resistance , 2008 .

[13]  C. Kost,et al.  Priming of indirect defences. , 2006, Ecology letters.

[14]  J. Thompson,et al.  Molecular characterization of an Arabidopsis gene encoding hydroperoxide lyase, a cytochrome P-450 that is wound inducible. , 1998, Plant physiology.

[15]  A. Schaller,et al.  Enzymes in jasmonate biosynthesis - structure, function, regulation. , 2009, Phytochemistry.

[16]  In Sun Hwang,et al.  The Pepper 9-Lipoxygenase Gene CaLOX1 Functions in Defense and Cell Death Responses to Microbial Pathogens1[C][W][OA] , 2009, Plant Physiology.

[17]  Liping Zhang,et al.  A Tea Hydroperoxide Lyase Gene, CsiHPL1, Regulates Tomato Defense Response Against Prodenia Litura (Fabricius) and Alternaria Alternata f. sp. Lycopersici by Modulating Green Leaf Volatiles (GLVs) Release and Jasmonic Acid (JA) Gene Expression , 2013, Plant Molecular Biology Reporter.

[18]  P. M. Findeis,et al.  Cationic substrates of soybean lipoxygenase-1. , 2011, Bioorganic chemistry.

[19]  J. Hubert,et al.  Acaricidal effects of natural six-carbon and nine-carbon aldehydes on stored-product mites , 2008, Experimental and Applied Acarology.

[20]  Xueyong Yang,et al.  The Expression Profiling of the Lipoxygenase (LOX) Family Genes During Fruit Development, Abiotic Stress and Hormonal Treatments in Cucumber (Cucumis sativus L.) , 2012, International journal of molecular sciences.

[21]  J. Tumlinson,et al.  Airborne signals prime plants against insect herbivore attack. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[22]  R. Malheiro,et al.  Volatile profile of Arbutus unedo L. fruits through ripening stage , 2011 .

[23]  F. Daayf,et al.  Signaling cross-talk in plant disease resistance. , 2013, Plant science : an international journal of experimental plant biology.

[24]  T. Hamilton-Kemp,et al.  Interaction with and effects on the profile of proteins of Botrytis cinerea by C6 aldehydes. , 2007, Journal of agricultural and food chemistry.

[25]  S. Ryu.  Phospholipid-derived signaling mediated by phospholipase A in plants. , 2004, Trends in plant science.

[26]  P. Schieberle,et al.  Characterization of the key aroma compounds in the beverage prepared from Darjeeling black tea: quantitative differences between tea leaves and infusion. , 2006, Journal of agricultural and food chemistry.

[27]  José León,et al.  Differential distribution of the lipoxygenase pathway enzymes within potato chloroplasts. , 2006, Journal of experimental botany.

[28]  R. Fall,et al.  Volatile organic compounds emitted after leaf wounding: On‐line analysis by proton‐transfer‐reaction mass spectrometry , 1999 .

[29]  I. Feussner,et al.  The lipoxygenase-dependent oxygenation of lipid body membranes is promoted by a patatin-type phospholipase in cucumber cotyledons , 2010, Journal of experimental botany.

[30]  J. Blein,et al.  Involvement of Lipoxygenase-dependent Production of Fatty Acid Hydroperoxides in the Development of the Hypersensitive Cell Death induced by Cryptogein on Tobacco Leaves* , 1999, The Journal of Biological Chemistry.

[31]  D. Hannapel,et al.  Lipoxygenase Is Involved in the Control of Potato Tuber Development , 2001, Plant Cell.

[32]  I. Baldwin,et al.  Shared signals -'alarm calls' from plants increase apparency to herbivores and their enemies in nature. , 2007, Ecology letters.

[33]  J. Gershenzon,et al.  Characterization of a BAHD acyltransferase responsible for producing the green leaf volatile (Z)-3-hexen-1-yl acetate in Arabidopsis thaliana. , 2007, The Plant journal : for cell and molecular biology.

[34]  Huan-wen Meng,et al.  Isolation, Expression, and Characterization of a Hydroperoxide Lyase Gene from Cucumber , 2013, International journal of molecular sciences.

[35]  V. Tešević,et al.  Volatile compounds in medlar fruit (Mespilus germanica L.) at two ripening stages , 2013 .

[36]  D. Kliebenstein,et al.  Distinct Roles of Jasmonates and Aldehydes in Plant-Defense Responses , 2008, PloS one.

[37]  John H. Loughrin,et al.  How caterpillar-damaged plants protect themselves by attracting parasitic wasps. , 1995, Proceedings of the National Academy of Sciences of the United States of America.

[38]  K. Matsui,et al.  Intermittent exposure to traces of green leaf volatiles triggers a plant response , 2012, Scientific Reports.

[39]  M. Hamberg,et al.  Hydroperoxide lyases (CYP74C and CYP74B) catalyze the homolytic isomerization of fatty acid hydroperoxides into hemiacetals. , 2006, Biochimica et biophysica acta.

[40]  Ivo Feussner,et al.  The lipoxygenase pathway. , 2003, Annual review of plant biology.

[41]  A. Brash,et al.  Allene oxide synthases and allene oxides. , 2002, Prostaglandins & other lipid mediators.

[42]  A. V. Van Dijken,et al.  Characterization of three cloned and expressed 13-hydroperoxide lyase isoenzymes from alfalfa with unusual N-terminal sequences and different enzyme kinetics. , 2000, European journal of biochemistry.

[43]  I. Feussner,et al.  Comparative molecular and biochemical characterization of segmentally duplicated 9-lipoxygenase genes ZmLOX4 and ZmLOX5 of maize , 2010, Planta.

[44]  W. Schwab,et al.  Cloning and characterization of a 9-lipoxygenase gene induced by pathogen attack from Nicotiana benthamiana for biotechnological application , 2011, BMC biotechnology.

[45]  I. Feussner,et al.  Attacks by a piercing-sucking insect (Myzus persicae Sultzer) or a chewing insect (Leptinotarsa decemlineata Say) on potato plants (Solanum tuberosum L.) induce differential changes in volatile compound release and oxylipin synthesis , 2009, Journal of experimental botany.

[46]  I. Feussner,et al.  Fatty acid 9‐ and 13‐hydroperoxide lyases from cucumber1 , 2000, FEBS letters.

[47]  J. Blein,et al.  The combined action of 9 lipoxygenase and galactolipase is sufficient to bring about programmed cell death during tobacco hypersensitive response , 2005 .

[48]  B. Vosman,et al.  Exploiting natural variation to identify insect-resistance genes. , 2011, Plant biotechnology journal.

[49]  A. Schaller,et al.  Enzymes in Jasmonate Biosynthesis — Structure, Function, Regulation , 2010 .

[50]  C. Wasternack,et al.  Metabolic profiling of oxylipins in germinating cucumber seedlings – lipoxygenase-dependent degradation of triacylglycerols and biosynthesis of volatile aldehydes , 2002, Planta.

[51]  I. Feussner,et al.  Disruption of a maize 9-lipoxygenase results in increased resistance to fungal pathogens and reduced levels of contamination with mycotoxin fumonisin. , 2007, Molecular plant-microbe interactions : MPMI.

[52]  Jean-Luc Cacas,et al.  The 9-lipoxygenase GhLOX1 gene is associated with the hypersensitive reaction of cotton Gossypium hirsutum to Xanthomonas campestris pv malvacearum. , 2007, Plant physiology and biochemistry : PPB.

[53]  Beom-Soon Choi,et al.  The lipoxygenase gene family: a genomic fossil of shared polyploidy between Glycine max and Medicago truncatula , 2008, BMC Plant Biology.

[54]  Hiroyuki Yamamoto,et al.  Characterization of a hydroperoxide lyase gene and effect of C6-volatiles on expression of genes of the oxylipin metabolism in Citrus. , 2003, Journal of plant physiology.

[55]  J. Carlson,et al.  Plant Defense Priming against Herbivores: Getting Ready for a Different Battle1 , 2008, Plant Physiology.

[56]  I. Feussner,et al.  Lipid Peroxidation during the Hypersensitive Response in Potato in the Absence of 9-Lipoxygenases* , 2003, Journal of Biological Chemistry.

[57]  Robert C Schuurink,et al.  Regulation of floral scent production in petunia revealed by targeted metabolomics. , 2003, Phytochemistry.

[59]  I. Baldwin,et al.  Priming of plant defense responses in nature by airborne signaling between Artemisia tridentata and Nicotiana attenuata , 2006, Oecologia.

[60]  W. Mu,et al.  Molecular cloning, expression, and enzymatic characterization of Solanum tuberosum hydroperoxide lyase , 2012, European Food Research and Technology.

[61]  Jianan Huang,et al.  Comparison of catechins and volatile compounds among different types of tea using high performance liquid chromatograph and gas chromatograph mass spectrometer , 2011 .

[62]  G. Howe,et al.  Tomato allene oxide synthase and fatty acid hydroperoxide lyase, two cytochrome P450s involved in oxylipin metabolism, are targeted to different membranes of chloroplast envelope. , 2001, Plant physiology.

[63]  A. Hatanaka.  The biogeneration of green odour by green leaves , 1993 .

[64]  J. Xiong,et al.  Production of (2E)-hexenal by a hydroperoxide lyase from Amaranthus tricolor and salt-adding steam distillation for the separation , 2012, European Food Research and Technology.

[65]  K. Akimitsu,et al.  Role of hydroperoxide lyase in white-backed planthopper (Sogatella furcifera Horváth)-induced resistance to bacterial blight in rice, Oryza sativa L. , 2010, The Plant journal : for cell and molecular biology.

[66]  A. Kobayashi,et al.  Green leaf volatiles enhance methyl jasmonate response in Arabidopsis. , 2012, Journal of bioscience and bioengineering.

[67]  F. Jüttner,et al.  Volatile Products of the Lipoxygenase Pathway Evolved from Phaseolus vulgaris (L.) Leaves Inoculated with Pseudomonas syringae pv phaseolicola , 1993, Plant physiology.

[68]  S. De Domenico,et al.  Plant Cytochrome CYP74 Family: Biochemical Features, Endocellular Localisation, Activation Mechanism in Plant Defence and Improvements for Industrial Applications , 2009, Chembiochem : a European journal of chemical biology.

[69]  K. Matsui.  Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism. , 2006, Current opinion in plant biology.

[70]  M. Heil,et al.  Within-plant signaling by volatiles leads to induction and priming of an indirect plant defense in nature , 2007, Proceedings of the National Academy of Sciences.

[71]  J. Haeggström,et al.  Lipoxygenase and leukotriene pathways: biochemistry, biology, and roles in disease. , 2011, Chemical reviews.

[72]  J. Vliegenthart,et al.  Intracellular localization of lipoxygenases-1 and -2 in germinating soybean seeds by indirect labeling with protein a-colloidal gold complexes. , 1984, Plant physiology.

[73]  M. Held,et al.  Priming by airborne signals boosts direct and indirect resistance in maize. , 2006, The Plant journal : for cell and molecular biology.

[74]  W. Schwab,et al.  Identification of lipoxygenase (LOX) genes putatively involved in fruit flavour formation in apple (Malus × domestica) , 2013, Tree Genetics & Genomes.

[75]  Field evaluation of (E)-2-hexenal efficacy for behavioral manipulation of egg parasitoids in soybean , 2014, BioControl.

[76]  A. Brash.  Mechanistic aspects of CYP74 allene oxide synthases and related cytochrome P450 enzymes. , 2009, Phytochemistry.

[77]  C. Ryu,et al.  Airborne Induction and Priming of Plant Defenses against a Bacterial Pathogen1[C][OA] , 2009, Plant Physiology.

[78]  L. Rao,et al.  Fingerprint of black teas from India: identification of the regio-specific characteristics , 2002 .

[79]  A. Champion,et al.  Association of lipoxygenase response with resistance of various cotton genotypes to the bacterial blight disease , 2008 .

[80]  J. Siedow.  PLANT LIPOXYGENASE: STRUCTURE AND FUNCTION , 1991 .

[81]  Xuemin Wang,et al.  Patatin-related phospholipase A: nomenclature, subfamilies and functions in plants. , 2010, Trends in plant science.

[82]  B. Lee,et al.  Cloning and secretion of tomato hydroperoxide lyase in Pichia pastoris , 2005 .

[83]  Ü. Niinemets,et al.  Quantitative patterns between plant volatile emissions induced by biotic stresses and the degree of damage , 2013, Front. Plant Sci..

[84]  G. Mita,et al.  9-lipoxygenase metabolism is involved in the almond/Aspergillus carbonarius interaction. , 2007, Journal of experimental botany.

[85]  Xu-dong Zhu,et al.  The rice hydroperoxide lyase OsHPL3 functions in defense responses by modulating the oxylipin pathway. , 2012, The Plant journal : for cell and molecular biology.

[86]  Martin J. Mueller,et al.  ROS-mediated lipid peroxidation and RES-activated signaling. , 2013, Annual review of plant biology.

[87]  A. Brash,et al.  On the Role of Molecular Oxygen in Lipoxygenase Activation , 2010, The Journal of Biological Chemistry.

[88]  Jean-Marc Nicaud,et al.  Predicted secondary structure of hydroperoxide lyase from green bell pepper cloned in the yeast Yarrowia lipolytica , 2010 .

[89]  J. Vliegenthart,et al.  Fatty Acid Hydroperoxide Lyase: A Plant Cytochrome P450 Enzyme Involved in Wound Healing and Pest Resistance , 2001, Chembiochem : a European journal of chemical biology.

[90]  D. Phillips,et al.  The formation of cis-3-nonenal, trans-2-nonenal and hexanal from linoleic acid hydroperoxide isomers by a hydroperoxide cleavage enzyme system in cucumber (Cucumis sativus) fruits. , 1976, Biochimica et biophysica acta.

[91]  I. Baldwin,et al.  Defence on demand: mechanisms behind optimal defence patterns. , 2012, Annals of botany.

[92]  K. Matsui,et al.  E-2-hexenal promotes susceptibility to Pseudomonas syringae by activating jasmonic acid pathways in Arabidopsis , 2013, Front. Plant Sci..

[93]  M. Hamberg,et al.  Evaluation of the Antimicrobial Activities of Plant Oxylipins Supports Their Involvement in Defense against Pathogens1[W] , 2005, Plant Physiology.

[94]  Anne Plotto,et al.  Evaluation of volatiles from two subtropical strawberry cultivars using GC-olfactometry, GC-MS odor activity values, and sensory analysis. , 2011, Journal of agricultural and food chemistry.

[95]  Ian T. Baldwin,et al.  Volatile Signaling in Plant-Plant Interactions: "Talking Trees" in the Genomics Era , 2006, Science.

[96]  Godelieve Gheysen,et al.  Hormone defense networking in rice: tales from a different world. , 2013, Trends in plant science.

[97]  I. Baldwin,et al.  Silencing the Jasmonate Cascade: Induced Plant Defenses and Insect Populations , 2004, Science.

[98]  Georg Wohlfahrt,et al.  Detection of Plant Volatiles after Leaf Wounding and Darkening by Proton Transfer Reaction “Time-of-Flight” Mass Spectrometry (PTR-TOF) , 2011, PloS one.

[99]  J. Gershenzon.  Plant volatiles carry both public and private messages , 2007, Proceedings of the National Academy of Sciences.

[100]  K. Matsui,et al.  Direct fungicidal activities of C6-aldehydes are important constituents for defense responses in Arabidopsis against Botrytis cinerea. , 2008, Phytochemistry.

[101]  T. Nishioka,et al.  Changing green leaf volatile biosynthesis in plants: An approach for improving plant resistance against both herbivores and pathogens , 2006, Proceedings of the National Academy of Sciences.

[102]  P. Thonart,et al.  Optimization and scaling up of a biotechnological synthesis of natural green leaf volatiles using Beta vulgaris hydroperoxide lyase , 2012 .

[103]  P. Oeller,et al.  Plant Volatile Compounds: Sensory Cues for Health and Nutritional Value? , 2006 .

[104]  Y. Lou,et al.  (Z)-3-Hexenal, One of the Green Leaf Volatiles, Increases Susceptibility of Rice to the White-Backed Planthopper Sogatella furcifera , 2015, Plant Molecular Biology Reporter.

[105]  I. Murray,et al.  The maize lipoxygenase, ZmLOX10, mediates green leaf volatile, jasmonate and herbivore-induced plant volatile production for defense against insect attack. , 2013, The Plant journal : for cell and molecular biology.

[106]  I. Feussner,et al.  Maize 9-lipoxygenase ZmLOX3 controls development, root-specific expression of defense genes, and resistance to root-knot nematodes. , 2008, Molecular plant-microbe interactions : MPMI.

[107]  M. Esquerré-Tugayé,et al.  The incompatible interaction between Phytophthora parasitica var. nicotianae race 0 and tobacco is suppressed in transgenic plants expressing antisense lipoxygenase sequences. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[108]  R. Liechti,et al.  Jasmonate Biochemical Pathway , 2006, Science's STKE.

[109]  Mehmet Turan Ayseli,et al.  Characterization of the most aroma-active compounds in cherry tomato by application of the aroma extract dilution analysis. , 2014, Food chemistry.

[110]  M. Heil,et al.  Herbivore‐induced plant volatiles: targets, perception and unanswered questions , 2014 .

[111]  M. Hamberg,et al.  Role of 9-lipoxygenase and α-dioxygenase oxylipin pathways as modulators of local and systemic defense. , 2012, Molecular plant.

[112]  I. Baldwin,et al.  High levels of jasmonic acid antagonize the biosynthesis of gibberellins and inhibit the growth of Nicotiana attenuata stems. , 2013, The Plant journal : for cell and molecular biology.

[113]  W. Schwab,et al.  Overexpression of hydroperoxide lyase gene in Nicotiana benthamiana using a viral vector system. , 2010, Plant biotechnology journal.

[114]  M. Hamberg,et al.  The "heterolytic hydroperoxide lyase" is an isomerase producing a short-lived fatty acid hemiacetal. , 2004, Biochimica et biophysica acta.

[115]  S. Rothstein,et al.  C6-volatiles derived from the lipoxygenase pathway induce a subset of defense-related genes. , 1998, The Plant journal : for cell and molecular biology.

[116]  V. Gökmen,et al.  Flavor characteristics of seven grades of black tea produced in Turkey. , 2012, Journal of agricultural and food chemistry.

[117]  Alessandra Devoto,et al.  Jasmonate signalling network in Arabidopsis thaliana: crucial regulatory nodes and new physiological scenarios. , 2007, The New phytologist.

[118]  Guodong Wang,et al.  Activation of the Jasmonic Acid Pathway by Depletion of the Hydroperoxide Lyase OsHPL3 Reveals Crosstalk between the HPL and AOS Branches of the Oxylipin Pathway in Rice , 2012, PloS one.

[119]  K. Assigbétsé,et al.  Lipid peroxidation in cotton: Xanthomonas interactions and the role of lipoxygenases during the hypersensitive reaction. , 2002, The Plant journal : for cell and molecular biology.

[120]  I. Feussner,et al.  Biosynthesis of oxylipins in non-mammals. , 2009, Progress in lipid research.

[121]  Zeng Yan,et al.  Wound-induced green leaf volatiles cause the release of acetylated derivatives and a terpenoid in maize. , 2006, Phytochemistry.

[122]  I. Feussner,et al.  A lipoxygenase with linoleate diol synthase activity from Nostoc sp. PCC 7120. , 2008, The Biochemical journal.

[123]  Q. Pan,et al.  Isolation and characterization of two hydroperoxide lyase genes from grape berries , 2012, Molecular Biology Reports.

[124]  I. Lara,et al.  Biosynthesis of volatile aroma compounds in pear fruit stored under long-term controlled-atmosphere conditions , 2003 .

[125]  D. Svergun,et al.  Probing dimerization and structural flexibility of mammalian lipoxygenases by small-angle X-ray scattering. , 2011, Journal of molecular biology.

[126]  J. Manners,et al.  Jasmonate biosynthesis and signaling in monocots: a comparative overview , 2013, Plant Cell Reports.

[127]  Anthony L. Schilmiller,et al.  Harnessing plant trichome biochemistry for the production of useful compounds. , 2008, The Plant journal : for cell and molecular biology.

[128]  K. Matsui,et al.  Role of the Lipoxygenase/lyase Pathway of Host-food Plants in the Host Searching Behavior of Two Parasitoid Species, Cotesia glomerata and Cotesia plutellae , 2006, Journal of Chemical Ecology.

[129]  J. Schultz,et al.  Insect elicitors and exposure to green leafy volatiles differentially upregulate major octadecanoids and transcripts of 12-oxo phytodienoic acid reductases in Zea mays. , 2007, Molecular plant-microbe interactions : MPMI.

[130]  M. Walther,et al.  The N-terminal β-barrel domain of mammalian lipoxygenases including mouse 5-lipoxygenase is not essential for catalytic activity and membrane binding but exhibits regulatory functions. , 2011, Archives of biochemistry and biophysics.

[131]  W. Schwab,et al.  Overexpression of hydroperoxide lyase, peroxygenase and epoxide hydrolase in tobacco for the biotechnological production of flavours and polymer precursors. , 2012, Plant biotechnology journal.

[132]  P. Thonart,et al.  Conversion of green note aldehydes into alcohols by yeast alcohol dehydrogenase , 1999, Biotechnology Letters.

[133]  I. Baldwin,et al.  Insects Betray Themselves in Nature to Predators by Rapid Isomerization of Green Leaf Volatiles , 2010, Science.

[134]  G. Di Sansebastiano,et al.  Subcellular localisation of Medicago truncatula 9/13-hydroperoxide lyase reveals a new localisation pattern and activation mechanism for CYP74C enzymes , 2007, BMC Plant Biology.

[135]  Sufang Zhang,et al.  Plants Attract Parasitic Wasps to Defend Themselves against Insect Pests by Releasing Hexenol , 2007, PloS one.

[136]  C. Wasternack,et al.  Jasmonates: biosynthesis, perception, signal transduction and action in plant stress response, growth and development. An update to the 2007 review in Annals of Botany. , 2013, Annals of botany.

[137]  Yueyun Hong,et al.  The patatin-containing phospholipase A pPLAIIα modulates oxylipin formation and water loss in Arabidopsis thaliana. , 2012, Molecular plant.

[138]  Young Sam Seo,et al.  Cooperation and functional diversification of two closely related galactolipase genes for jasmonate biosynthesis. , 2008, Developmental cell.

[139]  P. Thonart,et al.  Optimisation of expression and immobilized metal ion affinity chromatographic purification of recombinant (His)6-tagged cytochrome P450 hydroperoxide lyase in Escherichia coli. , 2003, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[140]  K. Dehesh,et al.  Rice HYDROPEROXIDE LYASES with Unique Expression Patterns Generate Distinct Aldehyde Signatures in Arabidopsis1 , 2006, Plant Physiology.

[141]  Nathalie Veyrat,et al.  Herbivore-induced maize leaf volatiles affect attraction and feeding behavior of Spodoptera littoralis caterpillars , 2013, Front. Plant Sci..

[142]  B. M. Lange,et al.  Metabolic engineering of plant monoterpenes, sesquiterpenes and diterpenes--current status and future opportunities. , 2013, Plant biotechnology journal.

[143]  I. Baldwin,et al.  Antisense LOX expression increases herbivore performance by decreasing defense responses and inhibiting growth-related transcriptional reorganization in Nicotiana attenuata. , 2003, The Plant journal : for cell and molecular biology.

[144]  D. Oh,et al.  Lipoxygenases: potential starting biocatalysts for the synthesis of signaling compounds. , 2012, Biotechnology advances.

[145]  C. Wasternack,et al.  Jasmonates: an update on biosynthesis, signal transduction and action in plant stress response, growth and development. , 2007, Annals of botany.

[146]  R. Liechti,et al.  Jasmonate Signaling Pathway , 2006, Science's STKE.

[147]  Ivo Feussner,et al.  Lipoxygenases: occurrence, functions and catalysis. , 2006, Journal of plant physiology.

[148]  J. Rose,et al.  Regulation of ripening and opportunities for control in tomato and other fruits. , 2013, Plant biotechnology journal.

[149]  H. Kindl,et al.  Biosynthesis of fatty acid derived aldehydes is induced upon mechanical wounding and its products show fungicidal activities in cucumber. , 2006, Phytochemistry.

[150]  A. Hatanaka,et al.  Green-leaf-derived C6-aroma compounds with potent antibacterial action that act on both Gram-negative and Gram-positive bacteria. , 2002, Journal of agricultural and food chemistry.

[151]  P. Schieberle,et al.  Characterization of the key aroma compounds in pink guava (Psidium guajava L.) by means of aroma re-engineering experiments and omission tests. , 2009, Journal of agricultural and food chemistry.

[152]  Robert Fluhr,et al.  Citrus fruit bitter flavors: isolation and functional characterization of the gene Cm1,2RhaT encoding a 1,2 rhamnosyltransferase, a key enzyme in the biosynthesis of the bitter flavonoids of citrus. , 2004, The Plant journal : for cell and molecular biology.

[153]  B. Møller,et al.  Plant cytochromes P450: tools for pharmacology, plant protection and phytoremediation. , 2003, Current opinion in biotechnology.

[154]  I. Kaplan.  Attracting carnivorous arthropods with plant volatiles: The future of biocontrol or playing with fire? , 2012 .

[155]  J. Engelberth,et al.  Early Transcriptome Analyses of Z-3-Hexenol-Treated Zea mays Revealed Distinct Transcriptional Networks and Anti-Herbivore Defense Potential of Green Leaf Volatiles , 2013, PloS one.

[156]  H. Porta,et al.  Wounding and pathogen infection induce a chloroplast-targeted lipoxygenase in the common bean (Phaseolus vulgaris L.) , 2007, Planta.

[157]  M. Hamberg,et al.  Screening of oxylipins for control of oilseed rape (Brassica napus) fungal pathogens. , 2003, Phytochemistry.

[158]  Claus Schneider,et al.  Control of oxygenation in lipoxygenase and cyclooxygenase catalysis. , 2007, Chemistry & biology.

[159]  G. Howe,et al.  Role of phytohormones in insect-specific plant reactions. , 2012, Trends in plant science.

[160]  G. Di Sansebastiano,et al.  Molecular cloning and characterization of an almond 9-hydroperoxide lyase, a new CYP74 targeted to lipid bodies. , 2005, Journal of experimental botany.

[161]  Yaofa Li,et al.  Identification of plant chemicals attracting and repelling whiteflies , 2014, Arthropod-Plant Interactions.

[162]  Cuiqing Ma,et al.  Microbial transformation of propenylbenzenes for natural flavour production. , 2007, Trends in biotechnology.

[163]  S. Ishiguro,et al.  The DEFECTIVE IN ANTHER DEHISCENCE1 Gene Encodes a Novel Phospholipase A1 Catalyzing the Initial Step of Jasmonic Acid Biosynthesis, Which Synchronizes Pollen Maturation, Anther Dehiscence, and Flower Opening in Arabidopsis , 2001, The Plant Cell Online.

[164]  Dong-Lei Yang,et al.  Roles of plant hormones and their interplay in rice immunity. , 2013, Molecular plant.

[165]  M. Haring,et al.  Green Leaf Volatiles: A Plant’s Multifunctional Weapon against Herbivores and Pathogens , 2013, International journal of molecular sciences.

[166]  D. Hildebrand,et al.  Watermelon (Citrullus lanatus) hydroperoxide lyase greatly increases C6 aldehyde formation in transgenic leaves. , 2005, Journal of agricultural and food chemistry.