If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.
Synonyms: LOX superpathway
|Superclasses:||Biosynthesis → Secondary Metabolites Biosynthesis → Fatty Acid Derivatives Biosynthesis|
Expected Taxonomic Range: Embryophyta
The lipoxygenase-catalyzed conversion of polyenoic fatty acids, specifically linoleate and linolenate in plants, and the subsequent reactions are collectively called the lipoxygenase pathway. The lipoxygenase pathway plays an important role in plant defense and giving plants the special "fresh green" odor.
Lipoxygenases (LOX) are ubiquitous enzymes in eukaryotes. Depending on the positional specificities, they are further classified as 9-LOX and 13-LOX, converting polyunsaturated fatty acids to 9-hydroperoxides (9-HOPD and 9-HPOT) and 13-hydroperoxides (13-HPOD and 13-HPOT), respectively. The hydroperoxide intermediates are further metabolized by enzymes such as allene oxide synthase (AOS), hydroperoxide lyase (HPL), and divinyl ether synthase (DES), all belonging to the CYP74 family. Depending on the substrate preferences, being either a 9-hydroperoxide or 13-hydroperoxide, these enzymes are divided into 9- or 13-AOS, 9- or 13-HPL, and 9- or 13-DES. 13-AOS is ubiquitous to plants, it leads to the biosynthesis of the plant hormone and signaling molecule jasmonic acid. Similarly, 13-HPL activity has been detected in many plants. It leads to the biosynthesis of the regulatory molecule traumatin (12-oxo-trans-10-dodecenoate). In addition, the aldehydes and alcohols produced by 13-HPL give the unique flavors and tastes to plants, such as the cucumber odor. On the other hand, 9-AOS and 9-HPL have only been detected in a few plants. The 9-AOS product alpha-ketols may be involved in plant development control [Kongrit06]. The 9-HPL derived aldehydes are known as defense compounds [Kuroda05]. The DES activities have also only been detected in a few plants. Divinyl ethers such as colneleic acid and colnelenic acid, derived from DES act as antimicrobials [Itoh01].
Subpathways: jasmonic acid biosynthesis, traumatin and (Z)-3-hexen-1-yl acetate biosynthesis, divinyl ether biosynthesis II, 9-lipoxygenase and 9-hydroperoxide lyase pathway, 9-lipoxygenase and 9-allene oxide synthase pathway, divinyl ether biosynthesis I
Bell95: Bell E, Creelman RA, Mullet JE (1995). "A chloroplast lipoxygenase is required for wound-induced jasmonic acid accumulation in Arabidopsis." Proc Natl Acad Sci U S A 1995;92(19);8675-9. PMID: 7567995
Kongrit06: Kongrit D, Jisaka M, Kobayasi K, Nishigaichi Y, Nishimura K, Nagaya T, Yokota K (2006). "Molecular cloning, functional expression, and tissue distribution of a potato sprout allene oxide synthase involved in a 9-lipoxygenase pathway." Biosci Biotechnol Biochem 70(9);2160-8. PMID: 16960383
Kuroda05: Kuroda H, Oshima T, Kaneda H, Takashio M (2005). "Identification and functional analyses of two cDNAs that encode fatty acid 9-/13-hydroperoxide lyase (CYP74C) in rice." Biosci Biotechnol Biochem 69(8);1545-54. PMID: 16116284
Noordermeer01: Noordermeer MA, Veldink GA, Vliegenthart JF (2001). "Fatty acid hydroperoxide lyase: a plant cytochrome p450 enzyme involved in wound healing and pest resistance." Chembiochem 2(7-8);494-504. PMID: 11828481
Bachmann02: Bachmann A, Hause B, Maucher H, Garbe E, Voros K, Weichert H, Wasternack C, Feussner I (2002). "Jasmonate-induced lipid peroxidation in barley leaves initiated by distinct 13-LOX forms of chloroplasts." Biol Chem 383(10);1645-57. PMID: 12452441
Bate98: Bate NJ, Sivasankar S, Moxon C, Riley JM, Thompson JE, Rothstein SJ (1998). "Molecular characterization of an Arabidopsis gene encoding hydroperoxide lyase, a cytochrome P-450 that is wound inducible." Plant Physiol 1998;117(4);1393-400. PMID: 9701595
Boeglin08: Boeglin WE, Itoh A, Zheng Y, Coffa G, Howe GA, Brash AR (2008). "Investigation of substrate binding and product stereochemistry issues in two linoleate 9-lipoxygenases." Lipids 43(11);979-87. PMID: 18795358
Choi08: Choi HW, Lee BG, Kim NH, Park Y, Lim CW, Song HK, Hwang BK (2008). "A role for a menthone reductase in resistance against microbial pathogens in plants." Plant Physiol 148(1);383-401. PMID: 18599651
Creelman92: Creelman RA, Tierney ML, Mullet JE (1992). "Jasmonic acid/methyl jasmonate accumulate in wounded soybean hypocotyls and modulate wound gene expression." Proc Natl Acad Sci U S A 1992;89(11);4938-41. PMID: 1594598
Creelman95: Creelman RA, Mullet JE (1995). "Jasmonic acid distribution and action in plants: regulation during development and response to biotic and abiotic stress." Proc Natl Acad Sci U S A 1995;92(10);4114-9. PMID: 11607536
Cruz04: Cruz Castillo M, Martinez C, Buchala A, Metraux JP, Leon J (2004). "Gene-specific involvement of beta-oxidation in wound-activated responses in Arabidopsis." Plant Physiol 135(1);85-94. PMID: 15141068
DAuria02: D'Auria JC, Chen F, Pichersky E (2002). "Characterization of an acyltransferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri." Plant Physiol 130(1);466-76. PMID: 12226525
DAuria07: D'Auria JC, Pichersky E, Schaub A, Hansel A, Gershenzon J (2007). "Characterization of a BAHD acyltransferase responsible for producing the green leaf volatile (Z)-3-hexen-1-yl acetate in Arabidopsis thaliana." Plant J 49(2);194-207. PMID: 17163881
Delker07: Delker C, Zolman BK, Miersch O, Wasternack C (2007). "Jasmonate biosynthesis in Arabidopsis thaliana requires peroxisomal beta-oxidation enzymes--additional proof by properties of pex6 and aim1." Phytochemistry 68(12);1642-50. PMID: 17544464
Fammartino06: Fammartino A, Cardinale F, Gobel C, Mene-Saffrane L, Fournier J, Feussner I, Esquerre-Tugaye MT (2006). "Characterisation of a Divinyl Ether Biosynthetic Pathway Specifically Associated with Pathogenesis in Nicotiana tabacum." Plant Physiol 143(1);378-88. PMID: 17085514
Farmer90: Farmer EE, Ryan CA (1990). "Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves." Proc Natl Acad Sci U S A 1990;87(19);7713-6. PMID: 11607107
Fonseca09: Fonseca S, Chini A, Hamberg M, Adie B, Porzel A, Kramell R, Miersch O, Wasternack C, Solano R (2009). "(+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate." Nat Chem Biol 5(5);344-50. PMID: 19349968
Gobel01: Gobel C, Feussner I, Schmidt A, Scheel D, Sanchez-Serrano J, Hamberg M, Rosahl S (2001). "Oxylipin profiling reveals the preferential stimulation of the 9-lipoxygenase pathway in elicitor-treated potato cells." J Biol Chem 276(9);6267-73. PMID: 11085991
Grechkin96: Grechkin AN, Hamberg M (1996). "Divinyl ether synthase from garlic (Allium sativum L.) bulbs: sub-cellular localization and substrate regio-and stereospecificity." FEBS Lett 388(2-3);112-4. PMID: 8690066
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