Vernolic acid (leukotoxin B[1]) is a long chain fatty acid that is monounsaturated and contains an epoxide. It is the R,R-cis epoxide derived from the C12–C13 alkene of linoleic acid.[2] Vernolic acid was first definitively characterized in 1954.[3] It is a major component in vernonia oil, which is produced in abundance by the genera Vernonia and Euphorbia and is a potentially useful biofeedstock.
Vernonia oil is extracted from the seeds of the Vernonia galamensis (ironweed), a plant native to eastern Africa. The seeds contain about 40 to 42% oil of which 73 to 80% is vernolic acid. The best varieties of V. anthelmintica contain about 30% less vernolic acid.
Vernolic acid is not commonly found in plants in significant quantities, but some plants which do contain it are Vernonia, Stokesia, Crepis (from the daisy family), and Euphorbia lagascae and Bernardia pulchella from the Euphorbiaceae.[4]
Potential applicationsedit
Vernonia oil has been proposed as a precursor to adhesives, varnishes and paints, and industrial coatings. Its low viscosity recommends its use as a nonvolatile solvent in oil-based paints since it will become incorporated in the dry paint rather than evaporating into the air.[5]
In its application as an epoxy oil,[6] vernonia oil competes with soybean or linseed oil, which supply most of the market for these applications. Its low viscosity makes it more desirable than fully epoxidized linseed or soybean oils. It is comparable to partially epoxidized linseed or soybean oil.[7]
Toxicityedit
In a variety of mammalian species, vernolic acid is made by the metabolism of linoleic acid by cytochrome P450epoxygenase enzymes; under these circumstances it is termed leukotoxin because of its toxic effects on leukocytes and other cell types and of its ability to produce multiple organ failure and respiratory distress when injected into rodent animal models of the acute respiratory distress syndrome.[8][9] These effects appear due to the conversion of vernolic acid to its dihydroxy counterparts, 12S,13R- and 12R,13S-dihydroxy-cis-9-octadecenoic acids by soluble epoxide hydrolase (this dihydroxy mixture has been termed leukotoxin diol).[10][9] Some studies suggest but have not yet proven that vernolic acid is responsible for or contributes to multiple organ failure, respiratory distress, and certain other cataclysmic diseases in humans (see epoxygenase subsection on linoleic acid).
^National Center for Biotechnology Information. "PubChem Compound Summary for CID 6449780, Vernolic acid". PubChem. Retrieved 29 May 2023.
^Metzger, J. O.; Bornscheuer, U. (2006). "Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification". Applied Microbiology and Biotechnology. 71 (1): 13–22. doi:10.1007/s00253-006-0335-4. PMID 16604360. S2CID 28601501.
^Gunstone FD (1954). "Fatty acids. Part II. The nature of the oxygenated acid present in Vernonia anthelmintica (Willd.) seed oil". Journal of the Chemical Society. 1954: 1611–1616. doi:10.1039/JR9540001611.
^Cahoon EB, Ripp KG, Hall SE, McGonigle B (February 2002). "Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed". Plant Physiology. 128 (2): 615–24. doi:10.1104/pp.010768. PMC148923. PMID 11842164.
^Teynor TM, Putnam DJ, Oplinger ES, Oelke EA, Kelling KA, Doll JD (February 1992). "Vernonia". Alternative Field Crops Manual. Retrieved 2006-09-10.
^Mohamed AI, Mebrahtu T, Andebrhan T (1999). Janick J (ed.). "Variability in oil and vernolic acid contents in the new Vernonia galamensis collection from East Africa". Perspectives on New Crops and New Uses: 272–274. Retrieved 2006-09-10.
^Muturi P, Wang D, Dirlikov S (1994). "Epoxidized vegetable oils as reactive diluents I. Comparison of vernonia, epoxidized soybean and epoxidized linseed oils". Progress in Organic Coatings. 25: 85–94. doi:10.1016/0300-9440(94)00504-4.
^Linhartová I, Bumba L, Mašín J, Basler M, Osička R, Kamanová J, Procházková K, Adkins I, Hejnová-Holubová J, Sadílková L, Morová J, Sebo P (November 2010). "RTX proteins: a highly diverse family secreted by a common mechanism". FEMS Microbiology Reviews. 34 (6): 1076–112. doi:10.1111/j.1574-6976.2010.00231.x. PMC3034196. PMID 20528947.
^ abSpector AA, Kim HY (April 2015). "Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1851 (4): 356–65. doi:10.1016/j.bbalip.2014.07.020. PMC4314516. PMID 25093613.
^Greene JF, Newman JW, Williamson KC, Hammock BD (April 2000). "Toxicity of epoxy fatty acids and related compounds to cells expressing human soluble epoxide hydrolase". Chemical Research in Toxicology. 13 (4): 217–26. doi:10.1021/tx990162c. PMID 10775319.
January 01, 1970
vernolic, acid, leukotoxin, long, chain, fatty, acid, that, monounsaturated, contains, epoxide, epoxide, derived, from, alkene, linoleic, acid, first, definitively, characterized, 1954, major, component, vernonia, which, produced, abundance, genera, vernonia, . Vernolic acid leukotoxin B 1 is a long chain fatty acid that is monounsaturated and contains an epoxide It is the R R cis epoxide derived from the C12 C13 alkene of linoleic acid 2 Vernolic acid was first definitively characterized in 1954 3 It is a major component in vernonia oil which is produced in abundance by the genera Vernonia and Euphorbia and is a potentially useful biofeedstock Vernolic acid Names Preferred IUPAC name 9Z 12S 13R 12 13 epoxyoctadecenoic acid Other names Racemic Linoleic acid 12 13 oxide cis 12 Epoxyoctadeca cis 9 enoic acid Single enantiomer corresponding to IUPAC name isomer 12S 13R epoxy cis 9 octadecenoic acid 12S 13R EpOME Identifiers CAS Number 503 07 1 isomer Y32381 42 3 isomer Y17966 13 1 racemate Y 3D model JSmol isomer Interactive image isomer Interactive image ChemSpider 4444572 isomer N4952464 isomer N PubChem CID 5281128 isomer6449780 isomer UNII FR42854EPW isomer YFF156V3318 isomer Y4S5JF40ZOQ racemate Y InChI InChI 1S C18H32O3 c1 2 3 10 13 16 17 21 16 14 11 8 6 4 5 7 9 12 15 18 19 20 h8 11 16 17H 2 7 9 10 12 15H2 1H3 H 19 20 b11 8 t16 17 m0 s1 NKey CCPPLLJZDQAOHD BEBBCNLGSA N N isomer InChI 1 C18H32O3 c1 2 3 10 13 16 17 21 16 14 11 8 6 4 5 7 9 12 15 18 19 20 h8 11 16 17H 2 7 9 10 12 15H2 1H3 H 19 20 b11 8 t16 17 m0 s1Key CCPPLLJZDQAOHD BEBBCNLGBK isomer InChI 1 C18H32O3 c1 2 3 10 13 16 17 21 16 14 11 8 6 4 5 7 9 12 15 18 19 20 h8 11 16 17H 2 7 9 10 12 15H2 1H3 H 19 20 b11 8 t16 17 m1 s1Key CCPPLLJZDQAOHD GJGKEFFFBZ isomer InChI 1S C18H32O3 c1 2 3 10 13 16 17 21 16 14 11 8 6 4 5 7 9 12 15 18 19 20 h8 11 16 17H 2 7 9 10 12 15H2 1H3 H 19 20 b11 8 t16 17 m1 s1Key CCPPLLJZDQAOHD GJGKEFFFSA N SMILES isomer O C O CCCCCCC C C C C H 1O C H 1CCCCC isomer O C O CCCCCCC C C C C H 1O C H 1CCCCC Properties Chemical formula C 18H 32O 3 Molar mass 296 451 g mol 1 Appearance Colorless oil Melting point 23 to 25 C 73 to 77 F 296 to 298 K Solubility in water Insoluble Solubility in other solvents organic solvents Hazards Occupational safety and health OHS OSH Main hazards flammable Related compounds Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Occurrence 2 Potential applications 3 Toxicity 4 Related compounds 5 ReferencesOccurrence editVernonia oil is extracted from the seeds of the Vernonia galamensis ironweed a plant native to eastern Africa The seeds contain about 40 to 42 oil of which 73 to 80 is vernolic acid The best varieties of V anthelmintica contain about 30 less vernolic acid Vernolic acid is not commonly found in plants in significant quantities but some plants which do contain it are Vernonia Stokesia Crepis from the daisy family and Euphorbia lagascae and Bernardia pulchella from the Euphorbiaceae 4 Potential applications editVernonia oil has been proposed as a precursor to adhesives varnishes and paints and industrial coatings Its low viscosity recommends its use as a nonvolatile solvent in oil based paints since it will become incorporated in the dry paint rather than evaporating into the air 5 In its application as an epoxy oil 6 vernonia oil competes with soybean or linseed oil which supply most of the market for these applications Its low viscosity makes it more desirable than fully epoxidized linseed or soybean oils It is comparable to partially epoxidized linseed or soybean oil 7 Toxicity editIn a variety of mammalian species vernolic acid is made by the metabolism of linoleic acid by cytochrome P450 epoxygenase enzymes under these circumstances it is termed leukotoxin because of its toxic effects on leukocytes and other cell types and of its ability to produce multiple organ failure and respiratory distress when injected into rodent animal models of the acute respiratory distress syndrome 8 9 These effects appear due to the conversion of vernolic acid to its dihydroxy counterparts 12S 13R and 12R 13S dihydroxy cis 9 octadecenoic acids by soluble epoxide hydrolase this dihydroxy mixture has been termed leukotoxin diol 10 9 Some studies suggest but have not yet proven that vernolic acid is responsible for or contributes to multiple organ failure respiratory distress and certain other cataclysmic diseases in humans see epoxygenase subsection on linoleic acid Related compounds editcoronaric acid C9 C10 epoxide of linoleic acid References edit National Center for Biotechnology Information PubChem Compound Summary for CID 6449780 Vernolic acid PubChem Retrieved 29 May 2023 Metzger J O Bornscheuer U 2006 Lipids as renewable resources current state of chemical and biotechnological conversion and diversification Applied Microbiology and Biotechnology 71 1 13 22 doi 10 1007 s00253 006 0335 4 PMID 16604360 S2CID 28601501 Gunstone FD 1954 Fatty acids Part II The nature of the oxygenated acid present in Vernonia anthelmintica Willd seed oil Journal of the Chemical Society 1954 1611 1616 doi 10 1039 JR9540001611 Cahoon EB Ripp KG Hall SE McGonigle B February 2002 Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed Plant Physiology 128 2 615 24 doi 10 1104 pp 010768 PMC 148923 PMID 11842164 Teynor TM Putnam DJ Oplinger ES Oelke EA Kelling KA Doll JD February 1992 Vernonia Alternative Field Crops Manual Retrieved 2006 09 10 Mohamed AI Mebrahtu T Andebrhan T 1999 Janick J ed Variability in oil and vernolic acid contents in the new Vernonia galamensis collection from East Africa Perspectives on New Crops and New Uses 272 274 Retrieved 2006 09 10 Muturi P Wang D Dirlikov S 1994 Epoxidized vegetable oils as reactive diluents I Comparison of vernonia epoxidized soybean and epoxidized linseed oils Progress in Organic Coatings 25 85 94 doi 10 1016 0300 9440 94 00504 4 Linhartova I Bumba L Masin J Basler M Osicka R Kamanova J Prochazkova K Adkins I Hejnova Holubova J Sadilkova L Morova J Sebo P November 2010 RTX proteins a highly diverse family secreted by a common mechanism FEMS Microbiology Reviews 34 6 1076 112 doi 10 1111 j 1574 6976 2010 00231 x PMC 3034196 PMID 20528947 a b Spector AA Kim HY April 2015 Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism Biochimica et Biophysica Acta BBA Molecular and Cell Biology of Lipids 1851 4 356 65 doi 10 1016 j bbalip 2014 07 020 PMC 4314516 PMID 25093613 Greene JF Newman JW Williamson KC Hammock BD April 2000 Toxicity of epoxy fatty acids and related compounds to cells expressing human soluble epoxide hydrolase Chemical Research in Toxicology 13 4 217 26 doi 10 1021 tx990162c PMID 10775319 Retrieved from https en wikipedia org w index php title Vernolic acid amp oldid 1157588217, wikipedia, wiki, book, books, library,
