263399-35-5Relevant academic research and scientific papers
FATTY ACIDS IN SEED OIL FROM TURNERA ULMIFOLIA
Hosamani, Kallappa M.
, p. 1363 - 1366 (1993)
The seeds oil from turnera ulmifolia was found to contain the unusual fatty acids, 9,10-epoxy-octadec-cis-12-enoic acid (vernolic acid, 22.3percent), 7-(2-octacyclopropen-1-yl)heptanoic acid (malvalic acid, 5.6percent) and 8-(2-octacyclopropen-1-yl)octanoic acid (sterculic acid 4.3percent) along with other normal fatty acids.These fatty acids were characterized by FTIR, NMR, mass spectrometry, GC and chemical degradations.
Molecular characterization of NbEH1 and NbEH2, two epoxide hydrolases from Nicotiana benthamiana
Huang, Fong-Chin,Schwab, Wilfried
, p. 6 - 15 (2013/07/11)
Plant epoxide hydrolases (EH) form two major clades, named EH1 and EH2. To gain a better understanding of the biochemical roles of the two classes, NbEH1.1 and NbEH2.1 were isolated from Nicotiana benthamiana and StEH from potato and heterologously expressed in Escherichia coli. The purified recombinant proteins were assayed with a variety of substrates. NbEH1.1 only accepted some aromatic epoxides, and displayed the highest enzyme activity towards phenyl glycidyl ether. In contrast, NbEH2.1 displayed a broad substrate range and similar substrate specificity as StEH. The latter enzymes showed activity towards all fatty acid epoxides examined. The activity (Vmax) of NbEH1.1 towards phenyl glycidyl ether was 10 times higher than that of NbEH2.1. On the contrary, NbEH2.1 converted cis-9,10-epoxystearic acid with Vmax of 3.83 μmol min mg-1 but NbEH1.1 could not hydrolyze cis-9,10- epoxystearic acid. Expression analysis revealed that NbEH1.1 is induced by infection with tobacco mosaic virus (TMV) and wounding, whereas NbEH2.1 is present at a relatively constant level, not influenced by treatment with TMV and wounding. NbEH1.1 transcripts were present predominantly in roots, whereas NbEH2.1 mRNAs were detected primarily in leaves and stems. Overall, these two types of tobacco EH enzymes are distinguished not only by their gene expression, but also by different substrate specificities. EH1 seems not to participate in cutin biosynthesis and it may play a role in generating signals for activation of certain defence and stress responses in tobacco. However, members of the EH2 group hydrate fatty acid epoxides and may be involved in cutin monomer production in plants.
Linoleic acid epoxide promotes the maintenance of mitochondrial function and active Na+ transport following hypoxia
Nowak, Grazyna,Grant, David F.,Moran, Jeffery H.
, p. 161 - 175 (2008/12/21)
Low concentrations of arachidonic acid monoepoxides protect against ischemia/reperfusion injury. This study examined whether low concentrations of the linoleic acid monoepoxide, cis-12,13-epoxy-9-octadecenoic acid (12,13-EOA), protect renal cells against decreases in mitochondrial and transport functions induced by hypoxia/reoxygenation. Primary cultures of rabbit renal proximal tubular cells (RPTC) were pretreated with diluent or 1, 5, or 10μM 12,13-EOA for 1h and exposed to 2h hypoxia/0.5h reoxygenation in the absence of 12,13-EOA. Basal respiration, oligomycin-sensitive oxygen consumption (QO2), and ATP content decreased 31, 35 and 65%, respectively, following hypoxia/reoxygenation. Hypoxia/reoxygenation also increased mitochondrial membrane potential (ΔΨm). Pretreatment with 12,13-EOA prevented decreases in basal and oligomycin-sensitive QO2s and increases in ΔΨm. Despite the protection against decreases in mitochondrial function, 12,13-EOA pretreatment did not prevent the initial decrease in intracellular ATP content following hypoxia. However, pretreatment did accelerate the recovery of intracellular ATP levels during reoxygenation. Pretreatment with 12,13-EOA also prevented hypoxia-induced decreases in active Na+ transport. Ouabain-sensitive QO2 (a marker of active Na+ transport) decreased 38% following hypoxia/reoxygenation but was maintained in RPTC pretreated with 1, 5 or 10μM 12,13-EOA prior to hypoxia. Pretreatment of RPTC with the hydrolyzed product of 12,13-EOA, 12,13-dihydroxyoctadecenoic acid, did not have any protective effects against mitochondrial dysfunction and decreases in active Na+ transport. Thus, this is the first report demonstrating that preconditioning of RPTC with low concentrations of 12,13-EOA, but not its hydrolyzed product, maintains mitochondrial respiration, accelerates restoration of ATP levels, and prevents decreases in active Na+ transport following hypoxia/reoxygenation.
Oxygenated Fatty Acids with Anti-rice Blast Fungus Activity in Rice Plants
Kato, Tadahiro,Yamaguchi, Yoshihiro,Namai, Tsuneo,Hirukawa, Toshifumi
, p. 283 - 287 (2007/10/02)
Expecting that the different characteristics of rice plants against rice blast fungus, that is, susceptibility of the weaker cultivar, Sasanishiki and resistance of the stronger cultivars, Fukuyuki and Fukunishiki, may be due to the absence or presence of anti-fungus compounds in the rice plants, the anti-rice blast fungus substances in these three kinds of rice plants were explored.We found five epoxides and five allyl alcohols as anti-rice blast fungus compounds.The epoxides were 12,13-epoxy- and 9,10-epoxylinoleic acids, and 15,16-epoxy-, 12,13-epoxy-, and 9,10-epoxylinolenic acids.The allyl alcohols are 13-hydroxy and 9-hydroxy linoleic acids, and 16-hydroxy, 13-hydroxy, and 9-hydroxy linolenic acids.In inoculated Sasanishiki, the activity is due to the formation of the allyl alcohols.
