AI3-03520 (BioDeep_00000860737)

Main id: BioDeep_00000017263

 

PANOMIX_OTCML-2023


代谢物信息卡片


9,12-Octadecadienoic acid (9Z,12Z)-, methyl ester

化学式: C19H34O2 (294.2558664)
中文名称: 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(OC)=O
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

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

24 个代谢物同义名

9,12-Octadecadienoic acid (9Z,12Z)-, methyl ester; (9Z,12Z)-octadeca-9,12-dienoic acid methyl ester; 9,12-Octadecadienoic acid, methyl ester, (Z,Z)-; 9,12-Octadecadienoic acid (Z,Z)-, methyl ester; 9,12-Octadecadienoic acid, methyl ester; methyl (9Z,12Z)-octadeca-9,12-dienoate; Methyl 9-cis,12-cis-octadecadienoate; Methyl cis,cis-9,12-octadecadienoate; Linoleic acid, methyl ester (8CI); Linoleic acid, methyl ester; linoleic acid methyl ester; Linoleic acid,methyl ester; Methyl linoleate, native; Methyl octadecadienoate; Methyl lineoleate; EINECS 203-993-0; Methyl linoleate; NCGC00164324-01; FEMA No. 3411; L1876_SIGMA; 62280_FLUKA; NSC 93981; AI3-03520; 112-63-0



数据库引用编号

6 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)

145 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。



文献列表

  • Rabia Alghazeer, Abdullah A Burwaiss, Nazlin K Howell, Wafa S Alansari, Ghalia Shamlan, Areej A Eskandrani. Determining the Cytotoxicity of Oxidized Lipids in Cultured Caco-2 Cells Using Bioimaging Techniques. Molecules (Basel, Switzerland). 2020 Apr; 25(7):. doi: 10.3390/molecules25071693. [PMID: 32272768]
  • Chi-Na Zhao, Zong-Li Yao, Dan Yang, Jian Ke, Qing-Lai Wu, Jun-Kai Li, Xu-Dong Zhou. Chemical Constituents from Fraxinus hupehensis and Their Antifungal and Herbicidal Activities. Biomolecules. 2020 01; 10(1):. doi: 10.3390/biom10010074. [PMID: 31906487]
  • Rocío Casadey, Cecilia Challier, Alejandro Senz, Susana Criado. Antioxidant ability of tyrosol and derivative-compounds in the presence of O2(1Δg)-species. Studies of synergistic antioxidant effect with commercial antioxidants. Food chemistry. 2019 Jul; 285(?):275-281. doi: 10.1016/j.foodchem.2019.01.161. [PMID: 30797345]
  • Aline Rocha de Melo, Israel J Pereira Garcia, José Eduardo Serrão, Hérica Lima Santos, Luciana A Rodrigues Dos Santos Lima, Stênio Nunes Alves. Toxicity of different fatty acids and methyl esters on Culex quinquefasciatus larvae. Ecotoxicology and environmental safety. 2018 Jun; 154(?):1-5. doi: 10.1016/j.ecoenv.2018.02.009. [PMID: 29448064]
  • Chryssostomos Chatgilialoglu, Carla Ferreri, Maurizio Guerra, Abdelouahid Samadi, Vincent W Bowry. The Reaction of Thiyl Radical with Methyl Linoleate: Completing the Picture. Journal of the American Chemical Society. 2017 04; 139(13):4704-4714. doi: 10.1021/jacs.6b11320. [PMID: 28253623]
  • Hui Fan, Jonathan Smuts, Ling Bai, Phillip Walsh, Daniel W Armstrong, Kevin A Schug. Gas chromatography-vacuum ultraviolet spectroscopy for analysis of fatty acid methyl esters. Food chemistry. 2016 Mar; 194(?):265-71. doi: 10.1016/j.foodchem.2015.08.004. [PMID: 26471553]
  • Katarzyna Jodko-Piórecka, Grzegorz Litwinienko. Antioxidant activity of dopamine and L-DOPA in lipid micelles and their cooperation with an analogue of α-tocopherol. Free radical biology & medicine. 2015 Jun; 83(?):1-11. doi: 10.1016/j.freeradbiomed.2015.02.006. [PMID: 25701434]
  • Aya Umeno, Mizuki Takashima, Kazutoshi Murotomi, Yoshihiro Nakajima, Taisuke Koike, Toshiki Matsuo, Yasukazu Yoshida. Radical-scavenging Activity and Antioxidative Effects of Olive Leaf Components Oleuropein and Hydroxytyrosol in Comparison with Homovanillic Alcohol. Journal of oleo science. 2015; 64(7):793-800. doi: 10.5650/jos.ess15042. [PMID: 26136177]
  • Jin Young Kim, Jeong-Yong Cho, Young Kyu Ma, Yu Geon Lee, Jae-Hak Moon. Nonallergenic urushiol derivatives inhibit the oxidation of unilamellar vesicles and of rat plasma induced by various radical generators. Free radical biology & medicine. 2014 Jun; 71(?):379-389. doi: 10.1016/j.freeradbiomed.2014.03.041. [PMID: 24721153]
  • Qingsu Xia, Jun-Jie Yin, Yuewei Zhao, Yuh-Sen Wu, Yu-Qui Wang, Liang Ma, Shoujun Chen, Xin Sun, Peter P Fu, Hongtao Yu. UVA photoirradiation of nitro-polycyclic aromatic hydrocarbons-induction of reactive oxygen species and formation of lipid peroxides. International journal of environmental research and public health. 2013 Mar; 10(3):1062-84. doi: 10.3390/ijerph10031062. [PMID: 23493032]
  • Daniel R Cardoso, Regina S Scurachio, Willy G Santos, Paula Homem-de-Mello, Leif H Skibsted. Riboflavin-photosensitized oxidation is enhanced by conjugation in unsaturated lipids. Journal of agricultural and food chemistry. 2013 Mar; 61(9):2268-75. doi: 10.1021/jf305280x. [PMID: 23402498]
  • Youji Okada, Haruo Okajima, Kazuo Takeshita, Masato Kanamori. Kinetic study of Sasa veitchii extract as a radical scavenger and an antioxidant. Journal of food science. 2012 Nov; 77(11):C1211-7. doi: 10.1111/j.1750-3841.2012.02943.x. [PMID: 23057490]
  • Akio Kadowaki, Satoshi Iwamoto, Ryo Yamauchi. Reaction products of [60]fullerene during the autoxidation of methyl linoleate in bulk phase. Chemistry and physics of lipids. 2012 Feb; 165(2):178-85. doi: 10.1016/j.chemphyslip.2011.12.008. [PMID: 22209921]
  • Akio Kadowaki, Satoshi Iwamoto, Ryo Yamauchi. The antioxidative effect of fullerenes during the peroxidation of methyl linoleate in toluene. Bioscience, biotechnology, and biochemistry. 2012; 76(1):212-4. doi: 10.1271/bbb.110739. [PMID: 22232272]
  • T A Misharina, E S Alinkina, L D Fatkullina, A K Vorob'eva, I B Medvedeva, E B Burlakova. [Influence of the composition of essential oils on their antioxidant and antiradical properties]. Prikladnaia biokhimiia i mikrobiologiia. 2012 Jan; 48(1):117-23. doi: ". [PMID: 22567894]
  • 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]
  • Yuewei Zhao, Qingsu Xia, Jun-Jie Yin, Hongtao Yu, Peter P Fu. Photoirradiation of polycyclic aromatic hydrocarbon diones by UVA light leading to lipid peroxidation. Chemosphere. 2011 Sep; 85(1):83-91. doi: 10.1016/j.chemosphere.2011.05.040. [PMID: 21680011]
  • Philip T Lynett, Krista Butts, Vipraja Vaidya, Graham E Garrett, Derek A Pratt. The mechanism of radical-trapping antioxidant activity of plant-derived thiosulfinates. Organic & biomolecular chemistry. 2011 May; 9(9):3320-30. doi: 10.1039/c1ob05192j. [PMID: 21445384]
  • Atanu Biswas, Brajendra K Sharma, Karl Vermillion, J L Willett, H N Cheng. Preparation of acetonides from soybean oil, methyl soyate, and fatty esters. Journal of agricultural and food chemistry. 2011 Apr; 59(7):3066-70. doi: 10.1021/jf1026229. [PMID: 21375297]
  • Zhu Zhu, Lin Ma, Hai-yan Zhu, Xiao-sheng Yang, Xiao-jiang Hao. [Studies on the chemical constituents of Laportea bulbifera]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 Feb; 34(2):223-5. doi: ". [PMID: 21823478]
  • Roman Shchepin, Matias N Möller, Hye-young H Kim, Duane M Hatch, Silvina Bartesaghi, Balaraman Kalyanaraman, Rafael Radi, Ned A Porter. Tyrosine-lipid peroxide adducts from radical termination: para coupling and intramolecular Diels-Alder cyclization. Journal of the American Chemical Society. 2010 Dec; 132(49):17490-500. doi: 10.1021/ja106503a. [PMID: 21090613]
  • Cheng-Wu Fang, Jia-Jia Chen, Shou-Jin Liu. [Studies on the chemical constituents of rhizoma of Coniogramme japonica]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2010 Apr; 33(4):557-9. doi: ". [PMID: 20845785]
  • Fumie Saito, Satoshi Iwamoto, Ryo Yamauchi. Reaction products of gamma-tocopherol with (E)-4-oxo-2-nonenal in acidic acetonitrile. Bioscience, biotechnology, and biochemistry. 2010; 74(1):168-74. doi: 10.1271/bbb.90681. [PMID: 20057122]
  • Mizuka Nagai, Yoshiyuki Watanabe, Masato Nomura. Synthesis of acyl arbutin by an immobilized lipase and its suppressive ability against lipid oxidation in a bulk system and O/W emulsion. Bioscience, biotechnology, and biochemistry. 2009 Nov; 73(11):2501-5. doi: 10.1271/bbb.90504. [PMID: 19897895]
  • L Tesoriere, M Allegra, C Gentile, M A Livrea. Betacyanins as phenol antioxidants. Chemistry and mechanistic aspects of the lipoperoxyl radical-scavenging activity in solution and liposomes. Free radical research. 2009 Aug; 43(8):706-17. doi: 10.1080/10715760903037681. [PMID: 19548153]
  • Halina Mojzisova, Stéphanie Bonneau, Philippe Maillard, Kristian Berg, Daniel Brault. Photosensitizing properties of chlorins in solution and in membrane-mimicking systems. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 2009 Jun; 8(6):778-87. doi: 10.1039/b822269j. [PMID: 19492105]
  • Peter Sirmah, Stéphane Dumarçay, Eric Masson, Philippe Gérardin. Unusual amount of (-)-mesquitol from the heartwood of Prosopis juliflora. Natural product research. 2009; 23(2):183-9. doi: 10.1080/14786410801940968. [PMID: 19173126]
  • Natalia Fagali, Angel Catalá. Antioxidant activity of conjugated linoleic acid isomers, linoleic acid and its methyl ester determined by photoemission and DPPH techniques. Biophysical chemistry. 2008 Sep; 137(1):56-62. doi: 10.1016/j.bpc.2008.07.001. [PMID: 18656302]
  • Atanu Biswas, Brajendra K Sharma, J L Willett, Atanu Advaryu, S Z Erhan, H N Cheng. Azide derivatives of soybean oil and fatty esters. Journal of agricultural and food chemistry. 2008 Jul; 56(14):5611-6. doi: 10.1021/jf800123t. [PMID: 18558698]
  • Taina I Pajunen, Mikael P Johansson, Tapio Hase, Anu Hopia. Autoxidation of conjugated linoleic acid methyl ester in the presence of alpha-tocopherol: the hydroperoxide pathway. Lipids. 2008 Jul; 43(7):599-610. doi: 10.1007/s11745-008-3195-0. [PMID: 18546029]
  • Youji Okada, Kaoru Tanaka, Eisuke Sato, Haruo Okajima. Antioxidant activity of the new thiosulfinate derivative, S-benzyl phenylmethanethiosulfinate, from Petiveria alliacea L. Organic & biomolecular chemistry. 2008 Mar; 6(6):1097-102. doi: 10.1039/b715727d. [PMID: 18327337]
  • Jun-Jie Yin, Qingsu Xia, Shu-Hui Cherng, I-Wah Tang, Peter P Fu, Ge Lin, Hongtao Yu, Diógenes Herreño Sáenz. UVA photoirradiation of oxygenated benz[a]anthracene and 3-methylcholanthene--generation of singlet oxygen and induction of lipid peroxidation. International journal of environmental research and public health. 2008 Mar; 5(1):26-31. doi: 10.3390/ijerph5010026. [PMID: 18441402]
  • J J Yin, Q Xia, P P Fu. UVA photoirradiation of anhydroretinol--formation of singlet oxygen and superoxide. Toxicology and industrial health. 2007 Nov; 23(10):625-31. doi: 10.1177/0748233708090909. [PMID: 18717521]
  • G Márquez-Ruiz, F Holgado, M C García-Martínez, M C Dobarganes. A direct and fast method to monitor lipid oxidation progress in model fatty acid methyl esters by high-performance size-exclusion chromatography. Journal of chromatography. A. 2007 Sep; 1165(1-2):122-7. doi: 10.1016/j.chroma.2007.08.001. [PMID: 17706232]
  • Vitaly Roginsky, Galina A Zheltukhina, Vladimir E Nebolsin. Efficacy of metmyoglobin and hemin as a catalyst of lipid peroxidation determined by using a new testing system. Journal of agricultural and food chemistry. 2007 Aug; 55(16):6798-806. doi: 10.1021/jf0714362. [PMID: 17625877]
  • Levon Tavadyan, Avet Khachoyan, Gagik Martoyan, Afaf Kamal-Eldin. Numerical revelation of the kinetic significance of individual steps in the reaction mechanism of methyl linoleate peroxidation inhibited by alpha-tocopherol. Chemistry and physics of lipids. 2007 May; 147(1):30-45. doi: 10.1016/j.chemphyslip.2007.03.002. [PMID: 17445788]
  • L Tesoriere, M Allegra, D Butera, C Gentile, M A Livrea. Kinetics of the lipoperoxyl radical-scavenging activity of indicaxanthin in solution and unilamellar liposomes. Free radical research. 2007 Feb; 41(2):226-33. doi: 10.1080/10715760601026614. [PMID: 17364949]
  • Qingsu Xia, Jun Jie Yin, Peter P Fu, Mary D Boudreau. Photo-irradiation of Aloe vera by UVA--formation of free radicals, singlet oxygen, superoxide, and induction of lipid peroxidation. Toxicology letters. 2007 Jan; 168(2):165-75. doi: 10.1016/j.toxlet.2006.11.015. [PMID: 17197137]
  • Dejan D Andjelkovic, Byungrok Min, Dong Ahn, Richard C Larock. Elucidation of structural isomers from the homogeneous rhodium-catalyzed isomerization of vegetable oils. Journal of agricultural and food chemistry. 2006 Dec; 54(25):9535-43. doi: 10.1021/jf0612124. [PMID: 17147443]
  • Suhur Saeed, Duncan Gillies, Gabriele Wagner, Nazlin K Howell. ESR and NMR spectroscopy studies on protein oxidation and formation of dityrosine in emulsions containing oxidised methyl linoleate. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2006 Aug; 44(8):1385-92. doi: 10.1016/j.fct.2006.03.005. [PMID: 16690189]
  • Kai Xin Hay, Viduranga Yashasvi Waisundara, Mark Timmins, Boxin Ou, Kathleen Pappalardo, Nancy McHale, Dejian Huang. High-throughput quantitation of peroxyl radical scavenging capacity in bulk oils. Journal of agricultural and food chemistry. 2006 Jul; 54(15):5299-305. doi: 10.1021/jf061410v. [PMID: 16848509]
  • Qingsu Xia, Jun J Yin, Wayne G Wamer, Shu-Hui Cherng, Mary D Boudreau, Paul C Howard, Hongtao Yu, Peter P Fu. Photoirradiation of retinyl palmitate in ethanol with ultraviolet light--formation of photodecomposition products, reactive oxygen species, and lipid peroxides. International journal of environmental research and public health. 2006 Jun; 3(2):185-90. doi: 10.3390/ijerph2006030021. [PMID: 16823091]
  • Diógenes Herreno-Sáenz, Qingsu Xia, Li-Ting Chiu, Peter P Fu. UVA photoirradiation of halogenated-polycyclic aromatic hydrocarbons leading to induction of lipid peroxidation. International journal of environmental research and public health. 2006 Jun; 3(2):191-5. doi: 10.3390/ijerph2006030022. [PMID: 16823092]
  • Qingsu Xia, Jun Jie Yin, Shu-Hui Cherng, Wayne G Wamer, Mary Boudreau, Paul C Howard, Peter P Fu. UVA photoirradiation of retinyl palmitate--formation of singlet oxygen and superoxide, and their role in induction of lipid peroxidation. Toxicology letters. 2006 May; 163(1):30-43. doi: 10.1016/j.toxlet.2005.09.010. [PMID: 16384671]
  • Muneyuki Maekawa, Kazuaki Kawai, Yoshikazu Takahashi, Hikaru Nakamura, Takumi Watanabe, Ryuichi Sawa, Kenji Hachisuka, Hiroshi Kasai. Identification of 4-oxo-2-hexenal and other direct mutagens formed in model lipid peroxidation reactions as dGuo adducts. Chemical research in toxicology. 2006 Jan; 19(1):130-8. doi: 10.1021/tx050236m. [PMID: 16411666]
  • Kari A Trumbull, Bruce P Branchaud. An oxidatively releasable caging group that senses lipid peroxidation. Bioorganic & medicinal chemistry letters. 2005 Dec; 15(24):5544-7. doi: 10.1016/j.bmcl.2005.08.079. [PMID: 16202588]
  • Laura Nyström, Marjukka Mäkinen, Anna-Maija Lampi, Vieno Piironen. Antioxidant activity of steryl ferulate extracts from rye and wheat bran. Journal of agricultural and food chemistry. 2005 Apr; 53(7):2503-10. doi: 10.1021/jf048051t. [PMID: 15796586]
  • José-Ramón Morelló, Satu Vuorela, Maria-Paz Romero, Maria-José Motilva, Marina Heinonen. Antioxidant activity of olive pulp and olive oil phenolic compounds of the arbequina cultivar. Journal of agricultural and food chemistry. 2005 Mar; 53(6):2002-8. doi: 10.1021/jf048386a. [PMID: 15769127]
  • Y Okada, K Tanaka, I Fujita, E Sato, H Okajima. Antioxidant activity of thiosulfinates derived from garlic. Redox report : communications in free radical research. 2005; 10(2):96-102. doi: 10.1179/135100005x38851. [PMID: 15949130]
  • Subhash C Mojumdar, David A Becker, Gino A DiLabio, James J Ley, L Ross C Barclay, K U Ingold. Kinetic studies on stilbazulenyl-bis-nitrone (STAZN), a nonphenolic chain-breaking antioxidant in solution, micelles, and lipid membranes. The Journal of organic chemistry. 2004 Apr; 69(9):2929-36. doi: 10.1021/jo030390i. [PMID: 15104428]
  • Kenichi Yanagimoto, Hirotomo Ochi, Kwang-Geun Lee, Takayuki Shibamoto. Antioxidative activities of volatile extracts from green tea, oolong tea, and black tea. Journal of agricultural and food chemistry. 2003 Dec; 51(25):7396-401. doi: 10.1021/jf030127i. [PMID: 14640590]
  • Kazuyuki Hiramoto, Takumi Ohkawa, Natsuki Oikawa, Kiyomi Kikugawa. Is nitric oxide (NO) an antioxidant or a prooxidant for lipid peroxidation?. Chemical & pharmaceutical bulletin. 2003 Sep; 51(9):1046-50. doi: 10.1248/cpb.51.1046. [PMID: 12951445]
  • Vitaly Roginsky, Tatyana Barsukova, Denis Loshadkin, Evgeny Pliss. Substituted p-hydroquinones as inhibitors of lipid peroxidation. Chemistry and physics of lipids. 2003 Sep; 125(1):49-58. doi: 10.1016/s0009-3084(03)00068-9. [PMID: 14625075]
  • Rosario Zamora, Francisco J Hidalgo. Comparative methyl linoleate and methyl linolenate oxidation in the presence of bovine serum albumin at several lipid/protein ratios. Journal of agricultural and food chemistry. 2003 Jul; 51(16):4661-7. doi: 10.1021/jf025918j. [PMID: 14705893]
  • Carolyn F Goodridge, Randolph M Beaudry, James J Pestka, Denise M Smith. Solid phase microextraction-gas chromatography for quantifying headspace hexanal above freeze-dried chicken myofibrils. Journal of agricultural and food chemistry. 2003 Jul; 51(15):4185-90. doi: 10.1021/jf0260646. [PMID: 12848482]
  • Vitaly Roginsky. Chain-breaking antioxidant activity of natural polyphenols as determined during the chain oxidation of methyl linoleate in Triton X-100 micelles. Archives of biochemistry and biophysics. 2003 Jun; 414(2):261-70. doi: 10.1016/s0003-9861(03)00143-7. [PMID: 12781778]
  • Alberto Dávalos, Carmen Gómez-Cordovés, Begoña Bartolomé. Commercial dietary antioxidant supplements assayed for their antioxidant activity by different methodologies. Journal of agricultural and food chemistry. 2003 Apr; 51(9):2512-9. doi: 10.1021/jf021030j. [PMID: 12696929]
  • 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]
  • Shuichi Shimakawa, Yasukazu Yoshida, Etsuo Niki. Antioxidant action of a lipophilic nitroxyl radical, cyclohexane-1-spiro-2'-(4'-oxyimidazolidine-1'-oxyl) -5'-spiro-1'-cyclohexane, against lipid peroxidation under hypoxic conditions. Lipids. 2003 Mar; 38(3):225-31. doi: 10.1007/s11745-003-1055-3. [PMID: 12784862]
  • Marja P Kähkönen, Marina Heinonen. Antioxidant activity of anthocyanins and their aglycons. Journal of agricultural and food chemistry. 2003 Jan; 51(3):628-33. doi: 10.1021/jf025551i. [PMID: 12537433]
  • Ranieri Bizzarri, Benedetta Cerbai, Francesca Signori, Roberto Solaro, Ettore Bergamini, Ilaria Tamburini, Emo Chiellini. New perspectives for (S)-dolichol and (S)- nor dolichol synthesis and biological functions. Biogerontology. 2003; 4(6):353-63. doi: 10.1023/b:bgen.0000006555.87407.04. [PMID: 14739706]
  • Yasukazu Yoshida, Noriko Noguchi, Akira Watanabe, Yoshihide Iwaki, Makoto Yanagisawa, Tatsuhiko Kodama, Osamu Cynshi, Etsuo Niki. Antioxidant action of 2,2,4,6-tetra-substituted 2,3-dihydro-5-hydroxybenzofuran against lipid peroxidation: effects of substituents and side chain. Free radical research. 2002 Nov; 36(11):1171-8. doi: 10.1080/1071576021000016436. [PMID: 12592669]
  • Darwin W Reed, Christopher K Savile, Xiao Qiu, Peter H Buist, Patrick S Covello. Mechanism of 1,4-dehydrogenation catalyzed by a fatty acid (1,4)-desaturase of Calendula officinalis. European journal of biochemistry. 2002 Oct; 269(20):5024-9. doi: 10.1046/j.1432-1033.2002.03209.x. [PMID: 12383261]
  • Francisco J Hidalgo, Rosario Zamora. Methyl linoleate oxidation in the presence of bovine serum albumin. Journal of agricultural and food chemistry. 2002 Sep; 50(19):5463-7. doi: 10.1021/jf0255376. [PMID: 12207492]
  • Carla D Nuchi, Pilar Hernandez, D Julian McClements, Eric A Decker. Ability of lipid hydroperoxides to partition into surfactant micelles and alter lipid oxidation rates in emulsions. Journal of agricultural and food chemistry. 2002 Sep; 50(19):5445-9. doi: 10.1021/jf020095j. [PMID: 12207489]
  • X Zhang, G Eigendorf, D W Stebbing, S D Mansfield, J N Saddler. Degradation of trilinolein by laccase enzymes. Archives of biochemistry and biophysics. 2002 Sep; 405(1):44-54. doi: 10.1016/s0003-9861(02)00331-4. [PMID: 12176056]
  • Jens K S Møller, Laurette Sosniecki, Leif H Skibsted. Effect of nitrosylmyoglobin and saturated fatty acid anions on metmyoglobin-catalyzed oxidation of aqueous methyl linoleate emulsions. Biochimica et biophysica acta. 2002 Mar; 1570(2):129-34. doi: 10.1016/s0304-4165(02)00186-1. [PMID: 11985897]
  • Noriko Noguchi, Akihiro Nakada, Yasuhiro Itoh, Akira Watanabe, Etsuo Niki. Formation of active oxygen species and lipid peroxidation induced by hypochlorite. Archives of biochemistry and biophysics. 2002 Jan; 397(2):440-7. doi: 10.1006/abbi.2001.2689. [PMID: 11795906]
  • Yasukazu Yoshida, Etsuo Niki. Antioxidant effects of alpha- and gamma-carboxyethyl-6-hydroxychromans. BioFactors (Oxford, England). 2002; 16(3-4):93-103. doi: 10.1002/biof.5520160305. [PMID: 14530597]
  • C D Nuchi, D J McClements, E A Decker. Impact of tween 20 hydroperoxides and iron on the oxidation of methyl linoleate and salmon oil dispersions. Journal of agricultural and food chemistry. 2001 Oct; 49(10):4912-6. doi: 10.1021/jf010370m. [PMID: 11600043]
  • T Ezure, T Kanayama, C Nishino. Action of the novel antioxidants 4GBE43 and 2BBE43 against lipid peroxidation. Biochemical pharmacology. 2001 Aug; 62(3):335-40. doi: 10.1016/s0006-2952(01)00670-0. [PMID: 11434906]
  • V Roginsky. Superoxide dismutase enhances chain-breaking antioxidant capability of hydroquinones. Free radical research. 2001 Jul; 35(1):55-62. doi: 10.1080/10715760100300591. [PMID: 11697117]
  • Y Okada, H Okajima. Antioxidant effect of capsaicin on lipid peroxidation in homogeneous solution, micelle dispersions and liposomal membranes. Redox report : communications in free radical research. 2001; 6(2):117-22. doi: 10.1179/135100001101536120. [PMID: 11450982]
  • A R Brash. Autoxidation of methyl linoleate: identification of the bis-allylic 11-hydroperoxide. Lipids. 2000 Sep; 35(9):947-52. doi: 10.1007/s11745-000-0604-0. [PMID: 11026614]
  • Y Matsumura, C Satake, M Egami, T Mori. Interaction of gum arabic, maltodextrin and pullulan with lipids in emulsions. Bioscience, biotechnology, and biochemistry. 2000 Sep; 64(9):1827-35. doi: 10.1271/bbb.64.1827. [PMID: 11055384]
  • N Noguchi, K Nishino, E Niki. Antioxidant action of the antihypertensive drug, carvedilol, against lipid peroxidation. Biochemical pharmacology. 2000 May; 59(9):1069-76. doi: 10.1016/s0006-2952(99)00417-7. [PMID: 10704936]
  • N Weber, E Klein, K Vosmann, K D Mukherjee. Antioxidants eliminate stereomutation and thioether formation during lipase-catalyzed thioesterification and transthioesterification for the preparation of uniform cis- and trans-unsaturated thioesters. Chemistry and physics of lipids. 2000 Apr; 105(2):215-23. doi: 10.1016/s0009-3084(00)00125-0. [PMID: 10823469]
  • H H Refsgaard, L Tsai, E R Stadtman. Modifications of proteins by polyunsaturated fatty acid peroxidation products. Proceedings of the National Academy of Sciences of the United States of America. 2000 Jan; 97(2):611-6. doi: 10.1073/pnas.97.2.611. [PMID: 10639127]
  • M P Kähkönen, A I Hopia, H J Vuorela, J P Rauha, K Pihlaja, T S Kujala, M Heinonen. Antioxidant activity of plant extracts containing phenolic compounds. Journal of agricultural and food chemistry. 1999 Oct; 47(10):3954-62. doi: 10.1021/jf990146l. [PMID: 10552749]
  • H Shi, N Noguchi, E Niki. Comparative study on dynamics of antioxidative action of alpha-tocopheryl hydroquinone, ubiquinol, and alpha-tocopherol against lipid peroxidation. Free radical biology & medicine. 1999 Aug; 27(3-4):334-46. doi: 10.1016/s0891-5849(99)00053-2. [PMID: 10468207]
  • S S Pekkarinen, H Stöckmann, K Schwarz, I M Heinonen, A I Hopia. Antioxidant activity and partitioning of phenolic acids in bulk and emulsified methyl linoleate. Journal of agricultural and food chemistry. 1999 Aug; 47(8):3036-43. doi: 10.1021/jf9813236. [PMID: 10552604]
  • X H Wang, T Ohshima, H Ushio, C Koizumi. Proportion of geometrical hydroperoxide isomers generated by radical oxidation of methyl linoleate in homogeneous solution and in aqueous emulsion. Lipids. 1999 Jul; 34(7):675-9. doi: 10.1007/s11745-999-0412-6. [PMID: 10478924]
  • K Miyauchi, T Urakami, H Abeta, H Shi, N Noguchi, E Niki. Action of pyrroloquinolinequinol as an antioxidant against lipid peroxidation in solution. Antioxidants & redox signaling. 1999; 1(4):547-54. doi: 10.1089/ars.1999.1.4-547. [PMID: 11233151]
  • H Shi, N Noguchi, E Niki. Dynamics of antioxidant action of ubiquinol: a reappraisal. BioFactors (Oxford, England). 1999; 9(2-4):141-8. doi: 10.1002/biof.5520090208. [PMID: 10416025]
  • J Schwinn, H Sprinz, K Drössler, S Leistner, O Brede. Thiyl radical-induced cis/trans-isomerization of methyl linoleate in methanol and of linoleic acid residues in liposomes. International journal of radiation biology. 1998 Sep; 74(3):359-65. doi: 10.1080/095530098141492. [PMID: 9737538]
  • N Noguchi, M Takahashi, J Tsuchiya, H Yamashita, E Komuro, E Niki. Action of 21-aminosteroid U74006F as an antioxidant against lipid peroxidation. Biochemical pharmacology. 1998 Mar; 55(6):785-91. doi: 10.1016/s0006-2952(97)00533-9. [PMID: 9586950]
  • H Murase, J H Moon, R Yamauchi, K Kato, T Kunieda, T Yoshikawa, J Terao. Antioxidant activity of a novel vitamin E derivative, 2-(alpha-D glucopyranosyl)methyl-2,5,7,8-tetramethylchroman-6-ol. Free radical biology & medicine. 1998 Jan; 24(2):217-25. doi: 10.1016/s0891-5849(97)00221-9. [PMID: 9433895]
  • N Noguchi, H Yamashita, N Gotoh, Y Yamamoto, R Numano, E Niki. 2,2'-Azobis (4-methoxy-2,4-dimethylvaleronitrile), a new lipid-soluble azo initiator: application to oxidations of lipids and low-density lipoprotein in solution and in aqueous dispersions. Free radical biology & medicine. 1998 Jan; 24(2):259-68. doi: 10.1016/s0891-5849(97)00230-x. [PMID: 9433901]
  • 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]
  • N Noguchi, Y Iwaki, M Takahashi, E Komuro, Y Kato, K Tamura, O Cynshi, T Kodama, E Niki. 2,3-Dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran: design and evaluation as a novel radical-scavenging antioxidant against lipid peroxidation. Archives of biochemistry and biophysics. 1997 Jun; 342(2):236-43. doi: 10.1006/abbi.1997.9994. [PMID: 9186484]
  • M C Hanlon, D W Seybert. The pH dependence of lipid peroxidation using water-soluble azo initiators. Free radical biology & medicine. 1997; 23(5):712-9. doi: 10.1016/s0891-5849(97)00024-5. [PMID: 9296447]
  • E Niki. Mechanisms and dynamics of antioxidant action of ubiquinol. Molecular aspects of medicine. 1997; 18 Suppl(?):S63-70. doi: 10.1016/s0098-2997(97)00035-6. [PMID: 9266507]
  • J Radunz-Neto, G Corraze, P Bergot, S J Kaushik. Estimation of essential fatty acid requirements of common carp larvae using semi-purified artificial diets. Archiv fur Tierernahrung. 1996; 49(1):41-8. doi: 10.1080/17450399609381862. [PMID: 8766972]
  • 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 H Lee, J W Park. Lipid peroxidation products mediate damage of superoxide dismutase. Biochemistry and molecular biology international. 1995 Apr; 35(5):1093-102. doi: ". [PMID: 7549928]
  • K Rekdal, T B Melø. UV-initiated autoxidation of methyl linoleate in micelles studied by optical absorption. Chemistry and physics of lipids. 1995 Feb; 75(2):127-36. doi: 10.1016/0009-3084(94)02413-y. [PMID: 7743563]
  • L Iuliano, J Z Pedersen, G Rotilio, D Ferro, F Violi. A potent chain-breaking antioxidant activity of the cardiovascular drug dipyridamole. Free radical biology & medicine. 1995 Feb; 18(2):239-47. doi: 10.1016/0891-5849(94)e0123-z. [PMID: 7744307]
  • G Levin, S Mokady. Antioxidant activity of 9-cis compared to all-trans beta-carotene in vitro. Free radical biology & medicine. 1994 Jul; 17(1):77-82. doi: 10.1016/0891-5849(94)90009-4. [PMID: 7959168]
  • E Niki, S Minamisawa, M Oikawa, E Komuro. Membrane damage from lipid oxidation induced by free radicals and cigarette smoke. Annals of the New York Academy of Sciences. 1993 May; 686(?):29-37; discussion 37. doi: 10.1111/j.1749-6632.1993.tb39150.x. [PMID: 8512255]