Methyl linoleate (BioDeep_00000723954)

Main id: BioDeep_00000017263

Secondary id: BioDeep_00000860951

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Methyl octadeca-9,12-dienoate

化学式: C19H34O2 (294.2559)
中文名称: 甲基反亚油酸甲酯, 亚油酸甲酯
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCC/C=C/C/C=C/CCCCCCCC(=O)OC
InChI: InChI=1S/C19H34O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11H,3-6,9,12-18H2,1-2H3/b8-7+,11-10+

描述信息

D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides
Mixture with CNB89-S (*FEMA 3411*) is used as a flavouring ingredient. Methyl linoleate is found in many foods, some of which are white mustard, cloves, soft-necked garlic, and flaxseed.
Methyl linoleate, a major active constituent of Sageretia thea?fruit (HFSF), is a major anti-melanogenic compound. Methyl linoleate downregulates microphthalmia-associated transcription factor (MITF)?and tyrosinase-related proteins[1].
Methyl linoleate, a major active constituent of Sageretia thea?fruit (HFSF), is a major anti-melanogenic compound. Methyl linoleate downregulates microphthalmia-associated transcription factor (MITF)?and tyrosinase-related proteins[1].

同义名列表

4 个代谢物同义名

Methyl octadeca-9,12-dienoate; Methyl linolelaidate; Methyl linoleate; Methyl linolelaidate



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

271 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表


文献列表

  • Yuewei Zhao, Qingsu Xia, Jun Jie Yin, Ge Lin, Peter P Fu. Photoirradiation of dehydropyrrolizidine alkaloids--formation of reactive oxygen species and induction of lipid peroxidation. Toxicology letters. 2011 Sep; 205(3):302-9. doi: 10.1016/j.toxlet.2011.06.020. [PMID: 21723383]
  • Giuseppe Cefarelli, Brigida D'Abrosca, Antonio Fiorentino, Angelina Izzo, Claudio Mastellone, Severina Pacifico, Vincenzo Piscopo. Free-radical-scavenging and antioxidant activities of secondary metabolites from reddened cv. Annurca apple fruits. Journal of agricultural and food chemistry. 2006 Feb; 54(3):803-9. doi: 10.1021/jf052632g. [PMID: 16448186]
  • Marek Gogolewski, Malgorzata Nogala-Kalucka, Grzegorz Galuba. Studies on dimerisation of tocopherols under the influence of methyl linoleate peroxides. Die Nahrung. 2003 Apr; 47(2):74-8. doi: 10.1002/food.200390030. [PMID: 12744282]
  • E M Mäkinen, A I Hopia. Effects of alpha-tocopherol and ascorbyl palmitate on the isomerization and decomposition of methyl linoleate hydroperoxides. Lipids. 2000 Nov; 35(11):1215-23. doi: 10.1007/s11745-000-0638-3. [PMID: 11132181]
  • Y Okimotoa, A Watanabea, E Nikia, T Yamashitab, N Noguchia. A novel fluorescent probe diphenyl-1-pyrenylphosphine to follow lipid peroxidation in cell membranes. FEBS letters. 2000 Jun; 474(2-3):137-40. doi: 10.1016/s0014-5793(00)01587-8. [PMID: 10838073]
  • M Tokita, M Morita. Identification of new geometric isomers of methyl linoleate hydroperoxide and their chromatographic behavior. Bioscience, biotechnology, and biochemistry. 2000 May; 64(5):1044-6. doi: 10.1271/bbb.64.1044. [PMID: 10879477]
  • W Adam, S Andler, C R Saha-Möller. DNA cleavage induced by oxyl radicals generated in the photosensitized decomposition of fatty ester hydroperoxides derived from oleic and linoleic acid. Archives of biochemistry and biophysics. 1998 Jan; 349(2):261-6. doi: 10.1006/abbi.1997.0353. [PMID: 9448713]
  • R Yamauchi, K Goto, K Kato. Reaction of alpha-tocopherol in heated bulk phase in the presence of methyl linoleate (13S)-hydroperoxide or methyl linoleate. Lipids. 1998 Jan; 33(1):77-85. doi: 10.1007/s11745-998-0182-1. [PMID: 9470176]
  • M Oarada, N Kurita, M Miyaji. The effect of methyl linoleate hydroperoxides and radical initiator 2,2'-azobis (2-amidinopropane) dihydrochloride on antibody production by mouse spleen cells. Journal of nutritional science and vitaminology. 1997 Jun; 43(3):377-85. doi: 10.3177/jnsv.43.377. [PMID: 9268925]
  • A Hopia, S W Huang, E N Frankel. Effect of alpha-tocopherol and Trolox on the decomposition of methyl linoleate hydroperoxides. Lipids. 1996 Apr; 31(4):357-65. doi: 10.1007/bf02522920. [PMID: 8743046]
  • M Oarada, N Kurita, K Terao, M Miyaji. Effect of methyl linoleate hydroperoxides on murine natural killer cell-mediated cytotoxicity. Journal of nutritional science and vitaminology. 1995 Dec; 41(6):707-11. doi: 10.3177/jnsv.41.707. [PMID: 8926542]
  • M Rafiquzzaman, K Komagoe, K Tamagake. Comparative catalytic activity of hemin and hematin in the breakdown of methyllinoleate hydroperoxide and peroxidation of methyllinoleate in methanol. Chemical & pharmaceutical bulletin. 1995 Jun; 43(6):905-9. doi: 10.1248/cpb.43.905. [PMID: 7641308]
  • M Oarada, K Terao. Injury of mouse lymphocytes caused by exogenous methyl linoleate hydroperoxides in vitro. Biochimica et biophysica acta. 1992 Dec; 1165(2):135-40. doi: 10.1016/0005-2760(92)90178-x. [PMID: 1280468]
  • W Chamulitrat, H Iwahashi, D J Kelman, R P Mason. Evidence against the 1:2:2:1 quartet DMPO spectrum as the radical adduct of the lipid alkoxyl radical. Archives of biochemistry and biophysics. 1992 Aug; 296(2):645-9. doi: 10.1016/0003-9861(92)90621-3. [PMID: 1321592]
  • H Chen, D J Lee, E G Schanus. The inhibitory effect of water on the Co2+ and Cu2+ catalyzed decomposition of methyl linoleate hydroperoxides. Lipids. 1992 Mar; 27(3):234-9. doi: 10.1007/bf02536184. [PMID: 1522767]
  • M Oarada, N Kurita, M Miyaji, K Terao. Depression of phagocytic activity of human polymorphonuclear leukocytes by methyl linoleate hydroperoxides. Journal of nutritional science and vitaminology. 1991 Dec; 37(6):625-8. doi: 10.3177/jnsv.37.625. [PMID: 1819649]
  • K Kikugawa, T Kato, A Hayasaka. Formation of dityrosine and other fluorescent amino acids by reaction of amino acids with lipid hydroperoxides. Lipids. 1991 Nov; 26(11):922-9. doi: 10.1007/bf02535978. [PMID: 1805097]
  • T Nakayama, K Hori, K Terazawa, S Kawakishi. Comparison of the cytotoxicity of different hydroperoxides to V79 cells. Free radical research communications. 1991; 14(3):173-8. doi: 10.3109/10715769109088946. [PMID: 2060862]
  • E N Frankel, W E Neff, D Weisleder. Determination of methyl linoleate hydroperoxides by 13C nuclear magnetic resonance spectroscopy. Methods in enzymology. 1990; 186(?):380-7. doi: 10.1016/0076-6879(90)86131-e. [PMID: 2233305]
  • G Williamson. Multiple forms of glutathione S-transferase from pig liver--reaction with methyl linoleate hydroperoxides. The International journal of biochemistry. 1989; 21(1):23-30. doi: 10.1016/0020-711x(89)90023-2. [PMID: 2753198]
  • T Iio, K Yoden. Formation of fluorescent substances from degradation products of methyl linoleate hydroperoxides with amino compound. Lipids. 1988 Nov; 23(11):1069-72. doi: 10.1007/bf02535654. [PMID: 3237007]
  • K Hasegawa, K Fujimoto, T Kaneda, E N Frankel. Characterization of fluorescent products from reaction of methyl linoleate hydroperoxides with adenine in the presence of Fe2+ and ascorbic acid. Biochimica et biophysica acta. 1988 Oct; 962(3):371-6. doi: 10.1016/0005-2760(88)90267-6. [PMID: 3167087]
  • M Oarada, E Ito, K Terao, T Miyazawa, K Fujimoto, T Kaneda. The effect of dietary lipid hydroperoxide on lymphoid tissues in mice. Biochimica et biophysica acta. 1988 May; 960(2):229-35. doi: 10.1016/0005-2760(88)90068-9. [PMID: 3365444]
  • M Oarada, T Miyazawa, K Fujimoto, T Kaneda, E Ito, K Terao. Effect of dietary lipid peroxides on lymphoid tissues. Basic life sciences. 1988; 49(?):327-30. doi: 10.1007/978-1-4684-5568-7_49. [PMID: 3250489]
  • E N Frankel, E Selke, W E Neff. Thermal decomposition of methyl linoleate and methyl linolenate hydroperoxides analyzed by capillary gas chromatography. Basic life sciences. 1988; 49(?):319-26. doi: 10.1007/978-1-4684-5568-7_48. [PMID: 3250488]
  • M Kodama, F Inoue, T Nakayama, C Nagata. Activation of deoxycholic acid by the lipid peroxy radical and its covalent binding to nucleic acids. Archives of biochemistry and biophysics. 1987 Nov; 258(2):574-8. doi: 10.1016/0003-9861(87)90379-1. [PMID: 2445290]
  • J Terao, B P Lim, H Murakami, S Matsushita. Quinone formation from carcinogenic benzo[a]pyrene mediated by lipid peroxidation in phosphatidylcholine liposomes. Archives of biochemistry and biophysics. 1987 May; 254(2):472-81. doi: 10.1016/0003-9861(87)90126-3. [PMID: 3579313]
  • M Oarada, T Miyazawa, T Kaneda. Distribution of 14C after oral administration of [U-14C]labeled methyl linoleate hydroperoxides and their secondary oxidation products in rats. Lipids. 1986 Feb; 21(2):150-4. doi: 10.1007/bf02534437. [PMID: 3083174]
  • K Kikugawa, T Kato, Y Konoe, A Sawamura. Effects of methyl linoleate hydroperoxide and hydrogen peroxide on N-nitrosation of dimethylamine. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1985 Mar; 23(3):339-42. doi: 10.1016/0278-6915(85)90002-x. [PMID: 4040086]
  • T Kato, K Kikugawa. Effect of organic solvents and unsaturated fatty acids on nitrosamine formation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1984 Jun; 22(6):419-23. doi: 10.1016/0278-6915(84)90323-5. [PMID: 6539731]
  • T Imagawa, T Watanabe, T Nakamura. Inhibition of palmitate oxidation in mitochondria by lipid hydroperoxides. Journal of biochemistry. 1984 Mar; 95(3):771-8. doi: 10.1093/oxfordjournals.jbchem.a134668. [PMID: 6725234]
  • M Mihara, M Uchiyama, Y Yamane. [Effects of the addition of biological antioxidants on the thiobarbituric acid (TBA) reaction]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1983 Aug; 103(8):889-94. doi: 10.1248/yakushi1947.103.8_889. [PMID: 6663467]
  • E J Arffmann, K S Rasmussen, F N Hansen. Effect of some fatty acid methyl esters on gastrointestinal carcinogenesis by N-methyl-N-nitro-N-nitrosoguanidine in rats. Journal of the National Cancer Institute. 1981 Nov; 67(5):1071-5. doi: ". [PMID: 6946248]
  • A Shiotani, T Watanabe, I Matsuoka, T Nakamura. Comparative studies on the effects of linoleate and methyl linoleate and their hydroperoxides on the respiration and reactivities of rat heart mitochondria. Journal of biochemistry. 1980 Sep; 88(3):677-83. doi: 10.1093/oxfordjournals.jbchem.a133019. [PMID: 6448251]
  • W R Anderson, W C Tan, T Takatori, O S Privett. Toxic effects of hydroperoxide injections on rat lung. A light microscopical and ultrastructural study. Archives of pathology & laboratory medicine. 1976 Mar; 100(3):154-62. doi: NULL. [PMID: 946403]
  • A BANKS, E EDDIE, J G SMITH. Reactions of cytochrome-c with methyl linoleate hydroperoxide. Nature. 1961 Jun; 190(?):908-9. doi: 10.1038/190908a0. [PMID: 13686599]