rac 12-Oxophytodienoic Acid

  • CAT Number: R013866
  • CAS Number: 85551-10-6
  • Molecular Formula: C18H28O3
  • Molecular Weight: 292.419
  • Purity: ≥95%
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12-<wbr />oxo Phytodienoic acid (OPDA)(CAS: 85551-10-6) is a biologically active, immediate precursor of 7-<wbr /><em>epi</em> jasmonic acid. In addition to its link with jasmonic acid activity, OPDA appears to play an independent role in mediating resistance to pathogens and pests. As an endogenous signal transducer, OPDA has been show to increase alkaloid biosynthesis in <em>E. californica</em> cell cultures, increase tendril coiling of <em>B. dioica</em>, and suppress jasmonic acid-<wbr />induced programmed cell death in a conditional <em>A. flu</em> mutant.

Catalog Number R013866
CAS Number 85551-10-6
Molecular Formula

C18H28O3

Purity 95%
Storage -80°C
IUPAC Name 8-[(1S,5S)-4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoic acid
InChI InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-/t15-,16-/m0/s1
InChIKey PMTMAFAPLCGXGK-JMTMCXQRSA-N
SMILES CCC=CCC1C(C=CC1=O)CCCCCCCC(=O)O
Reference

[1]. Commun Integr Biol. 2020 May 13;13(1):63-66. doi: 10.1080/19420889.2020.1763562. eCollection 2020.<br />
Maize defense elicitor, 12-oxo-phytodienoic acid, prolongs aphid salivation.<br />
Grover S(1), Varsani S(1), Kolomiets MV(2), Louis J(1)(3).<br />
Author information: (1)Department of Entomology, University of Nebraska-Lincoln, Lincoln, NE, USA. (2)Department of Plant Pathology and Microbiology, Texas A &amp; M University, College Station, TX, USA. (3)Department of Biochemistry, University of Nebraska-Lincoln, Lincoln, NE, USA.<br />
12-Oxo-phytodienoic acid (OPDA), an intermediate in the jasmonic acid (JA) biosynthesis pathway, regulates diverse signaling functions in plants, including enhanced resistance to insect pests. We previously demonstrated that OPDA promoted enhanced callose accumulation and heightened resistance to corn leaf aphid (CLA; Rhopalosiphum maidis), a phloem sap-sucking insect pest of maize (Zea mays). In this study, we used the electrical penetration graph (EPG) technique to monitor and quantify the different CLA feeding patterns on the maize JA-deficient 12-oxo-phytodienoic acid reductase (opr7opr8) plants. CLA feeding behavior was unaffected on B73, opr7opr8 control plants (- OPDA), and opr7opr8 plants that were pretreated with OPDA (+ OPDA). However, exogenous application of OPDA on opr7opr8 plants prolonged aphid salivation, a hallmark of aphids&#39; ability to suppress the plant defense responses. Collectively, our results indicate that CLA utilizes its salivary secretions to suppress or unplug the OPDA-mediated sieve element occlusions in maize.<br />
DOI: 10.1080/19420889.2020.1763562 PMCID: PMC7238879 PMID: 32489516<br />
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[2]. Plant Physiol. 2019 Apr;179(4):1402-1415. doi: 10.1104/pp.18.01472. Epub 2019 Jan 14.<br />
12-Oxo-Phytodienoic Acid Acts as a Regulator of Maize Defense against Corn Leaf Aphid.<br />
Varsani S(1), Grover S(1), Zhou S(2)(3), Koch KG(1), Huang PC(4), Kolomiets MV(4), Williams WP(5), Heng-Moss T(1), Sarath G(6), Luthe DS(7), Jander G(2), Louis J(8)(9).<br />
Author information: (1)Department of Entomology, University of Nebraska, Lincoln, Nebraska 68583. (2)Boyce Thompson Institute, Cornell University, Ithaca, New York 14853. (3)School of Integrated Plant Sciences, Cornell University, Ithaca, New York 14853. (4)Department of Plant Pathology and Microbiology, Texas A&amp;M University, College Station, Texas 77843. (5)United States Department of Agriculture-Agricultural Research Service, Corn Host Plant Resistance Research Unit, Mississippi State, Mississippi 39762. (6)Wheat, Sorghum, and Forage Research Unit, United States Department of Agriculture-Agricultural Research Service, Lincoln, Nebraska 68583. (7)Department of Plant Science, Pennsylvania State University, University Park, Pennsylvania 16802. (8)Department of Entomology, University of Nebraska, Lincoln, Nebraska 68583 [email protected]. (9)Department of Biochemistry, University of Nebraska, Lincoln, Nebraska 68583.<br />
The corn leaf aphid (CLA; Rhopalosiphum maidis) is a phloem sap-sucking insect that attacks many cereal crops, including maize (Zea mays). We previously showed that the maize inbred line Mp708, which was developed by classical plant breeding, provides enhanced resistance to CLA. Here, using electrophysiological monitoring of aphid feeding behavior, we demonstrate that Mp708 provides phloem-mediated resistance to CLA. Furthermore, feeding by CLA on Mp708 plants enhanced callose deposition, a potential defense mechanism utilized by plants to limit aphid feeding and subsequent colonization. In maize, benzoxazinoids (BX) or BX-derived metabolites contribute to enhanced callose deposition by providing heightened resistance to CLA. However, BX and BX-derived metabolites were not significantly altered in CLA-infested Mp708 plants, indicating BX-independent defense against CLA. Evidence presented here suggests that the constitutively higher levels of 12-oxo-phytodienoic acid (OPDA) in Mp708 plants contributed to enhanced callose accumulation and heightened CLA resistance. OPDA enhanced the expression of ethylene biosynthesis and receptor genes, and the synergistic interactions of OPDA and CLA feeding significantly induced the expression of the transcripts encoding Maize insect resistance1-Cysteine Protease, a key defensive protein against insect pests, in Mp708 plants. Furthermore, exogenous application of OPDA on maize jasmonic acid-deficient plants caused enhanced callose accumulation and heightened resistance to CLA, suggesting that the OPDA-mediated resistance to CLA is independent of the jasmonic acid pathway. We further demonstrate that the signaling function of OPDA, rather than a direct toxic effect, contributes to enhanced CLA resistance in Mp708.<br />
DOI: 10.1104/pp.18.01472 PMCID: PMC6446797 PMID: 30643012 [Indexed for MEDLINE]<br />
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[3]. J Econ Entomol. 2018 Apr 2;111(2):917-922. doi: 10.1093/jee/tox374.<br />
12-Oxo-Phytodienoic Acid Enhances Wheat Resistance to Hessian Fly (Diptera: Cecidomyiidae) Under Heat Stress.<br />
Cheng G(1), Chen MS(2), Zhu L(1).<br />
Author information: (1)Department of Biological Sciences, Fayetteville State University, Fayetteville, NC. (2)USDA-ARS and Department of Entomology, Kansas State University, Manhattan, KS.<br />
12-Oxo-phytodienoic acid (OPDA) plays unique roles in plant defenses against biotic and abiotic stresses. In the current study, we infested two resistant wheat (Triticum aestivum L.) cultivars, &#39;Molly&#39; and &#39;Iris&#39;, with an avirulent Hessian fly population and determined the impact of exogenous OPDA application on wheat resistance to the insect under heat stress. We observed that Molly and Iris treated with OPDA solution prior to the heat treatment exhibited significantly enhanced insect resistance. We also measured OPDA concentrations at Hessian fly feeding sites in Molly infested with Hessian flies. We found that exogenous application of OPDA resulted in increased abundance of endogenous OPDA in Molly seedlings and that OPDA abundance in plants treated with the combination of heat and OPDA was similar to that of plants in the incompatible interaction. Our results suggest that high abundance of endogenous OPDA may be necessary for wheat under heat stress to resist to Hessian fly infestation.<br />
DOI: 10.1093/jee/tox374 PMID: 29420735 [Indexed for MEDLINE]<br />
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[4]. Biochem Biophys Res Commun. 2016 May 13;473(4):1288-1294. doi: 10.1016/j.bbrc.2016.04.060. Epub 2016 Apr 14.<br />
12-oxo-phytodienoic acid, a plant-derived oxylipin, attenuates lipopolysaccharide-induced inflammation in microglia.<br />
Taki-Nakano N(1), Kotera J(2), Ohta H(3).<br />
Author information: (1)Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-65 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan; Advanced Drug Research Laboratories, Sohyaku. Innovative Research Division, Mitsubishi Tanabe Pharma Corporation, 2-2-50, Kawagishi, Toda, Saitama 335-8505, Japan. (2)Advanced Drug Research Laboratories, Sohyaku. Innovative Research Division, Mitsubishi Tanabe Pharma Corporation, 2-2-50, Kawagishi, Toda, Saitama 335-8505, Japan. (3)Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-65 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan; School of Life Science and Technology, Tokyo Institute of Technology, 4259-B-65 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. Electronic address: [email protected].<br />
Jasmonates are plant lipid-derived oxylipins that act as key signaling compounds in plant immunity, germination, and development. Although some physiological activities of natural jasmonates in mammalian cells have been investigated, their anti-inflammatory actions in mammalian cells remain unclear. Here, we investigated whether jasmonates protect mouse microglial MG5 cells against lipopolysaccharide (LPS)-induced inflammation. Among the jasmonates tested, only 12-oxo-phytodienoic acid (OPDA) suppressed LPS-induced expression of the typical inflammatory cytokines interleukin-6 and tumor necrosis factor &alpha;. In addition, only OPDA reduced LPS-induced nitric oxide production through a decrease in the level of inducible nitric oxide synthase. Further mechanistic studies showed that OPDA suppressed neuroinflammation by inhibiting nuclear factor &kappa;B and p38 mitogen-activated protein kinase signaling in LPS-activated MG5 cells. In addition, OPDA induced expression of suppressor of cytokine signaling-1 (SOCS-1), a negative regulator of inflammation, in MG5 cells. Finally, we found that the nuclear factor erythroid 2-related factor 2 signaling cascade induced by OPDA is not involved in the anti-inflammatory effects of OPDA. These results demonstrate that OPDA inhibited LPS-induced cell inflammation in mouse microglial cells via multiple pathways, including suppression of nuclear factor &kappa;B, inhibition of p38, and activation of SOCS-1 signaling.<br />
DOI: 10.1016/j.bbrc.2016.04.060 PMID: 27086850 [Indexed for MEDLINE]<br />
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[5]. FEBS J. 2009 Sep;276(17):4693-704. doi: 10.1111/j.1742-4658.2009.07195.x. Epub 2009 Aug 3.<br />
Plant oxylipins: plant responses to 12-oxo-phytodienoic acid are governed by its specific structural and functional properties.<br />
B&ouml;ttcher C(1), Pollmann S.<br />
Author information: (1)CSIRO Plant Industry, Adelaide, Australia.<br />
One of the most challenging questions in modern plant science is how plants regulate their morphological and developmental adaptation in response to changes in their biotic and abiotic environment. A comprehensive elucidation of the underlying mechanisms will help shed light on the extremely efficient strategies of plants in terms of survival and propagation. In recent years, a number of environmental stress conditions have been described as being mediated by signaling molecules of the oxylipin family. In this context, jasmonic acid, its biosynthetic precursor, 12-oxo-phytodienoic acid (OPDA), and also reactive electrophilic species such as phytoprostanes play pivotal roles. Although our understanding of jasmonic acid-dependent processes and jasmonic acid signal-transduction cascades has made considerable progress in recent years, knowledge of the regulation and mode of action of OPDA-dependent plant responses is just emerging. This minireview focuses on recent work concerned with the elucidation of OPDA-specific processes in plants. In this context, aspects such as the differential recruitment of OPDA, either by de novo biosynthesis or by release from cyclo-oxylipin-galactolipids, and the conjugation of free OPDA are discussed.<br />
DOI: 10.1111/j.1742-4658.2009.07195.x PMID: 19663904 [Indexed for MEDLINE]

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