Methyl linoleate (BioDeep_00000017263)

 

Secondary id: BioDeep_00000619011, BioDeep_00000723954, BioDeep_00000860737

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


Methyl linoleate, United States Pharmacopeia (USP) Reference Standard

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 Chinese Herbal Medicine(otcml) 1.64%

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

Methyl linoleate is a fatty acid methyl ester of linoleic acid. It has been isolated from Neolitsea daibuensis. It has a role as a plant metabolite. It is functionally related to a linoleic acid.
Methyl linoleate is a natural product found in Tussilago farfara, Azadirachta indica, and other organisms with data available.
Methyl linoleate belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
A fatty acid methyl ester of linoleic acid. It has been isolated from Neolitsea daibuensis.
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

67 个代谢物同义名

Methyl linoleate, United States Pharmacopeia (USP) Reference Standard; 9,12-Octadecadienoic acid (9Z,12Z)-, methyl ester; (9Z,12Z)-octadeca-9,12-dienoic acid methyl ester; (9Z,12Z)-9,12-Octadecadienoic acid methyl ester; cis-9,cis-12-Octadecadienoic acid, methyl ester; methyl linoleate, 1-(14)C-labeled, (Z,Z)-isomer; 9,12-Octadecadienoic acid, methyl ester, (Z,Z)-; cis,cis-octadeca-9,12-dienoic acid methyl ester; cis-9,cis-12-Octadecadienoic acid methyl ester; Octadecadienoic acid methyl ester, 9,12-(Z,Z)-; 9,12-Octadecadienoic acid (Z,Z)-, methyl ester; 9,12-Octadecadienoic acid, methyl ester, (Z,Z); (Z,Z)-9,12-octadecadienoic acid methyl ester; Methyl ester(Z,Z)-9,12-Octadecadienoic acid; (9Z,12Z)-Octadecadienoic acid methyl ester; 1-O-Methyl (9Z,12Z)-octadecadienoic acid; 1-O-Methyl-(9Z,12Z)-octadecadienoic acid; Methyl 9-cis,12-cis-octadecadienoic acid; 9,12-Octadecadienoic acid, methyl ester; Methyl (9Z,12Z)-9,12-octadecadienoate #; methyl (9Z,12Z)-octadeca-9,12-dienoate; (9Z,12Z)-Methyl octadeca-9,12-dienoate; methyl (9E,12Z)-octadeca-9,12-dienoate; Methyl cis,cis-9, 12-octadecadienoate; (9Z,12Z)-Methyloctadeca-9,12-dienoate; Methyl linoleate, analytical standard; Methyl (9Z,12Z)-9,12-octadecadienoate; Methyl 9-cis,12-cis-octadecadienoate; 1-O-methyl-(9Z,12Z)-octadecadienoate; Methyl cis,cis-9,12-octadecadienoate; 1-O-Methyl (9Z,12Z)-octadecadienoate; METHYL CIS-9,CIS-12-OCTADECADIENOATE; Methyl (Z,Z)-9,12-octadecadienoate; Linoleic acid, methyl ester (8CI); Methyl (9Z,12Z)-octadecadienoate; cis-Linoleic acid methyl ester; Methyl (Z,Z)-9,12-octadienoate; Methyl 9Z,12Z-octadecadienoate; methyl linoleate, (E,Z)-isomer; methyl linoleate, (Z,E)-isomer; methyl linoleate, (E,E)-isomer; Methyl octadeca-9,12-dienoate; METHYL CIS-9,CIS-12 LINOLEATE; Methyl linoleate, >=99\\% (GC); METHYL OCTADEC-9,12-DIENOATE; Telfairic Acid methyl ester; Linoleic acid, methyl ester; linoleic acid-methyl ester; linoleic acid methyl ester; Linoleic acid,methyl ester; METHYL LINOLEATE [USP-RS]; Methyl linoleate, native; Natural methyl linoleate; Methyl octadecadienoate; METHYL LINOLEATE [INCI]; Linoleate methyl ester; METHYL LINOLEATE [MI]; Methyl linoleic acid; Methyl lineoleate; Methyl linoleate; UNII-24N6726DE5; Methyl linolate; Tox21_302917; Tox21_201403; 24N6726DE5; AI3-03520; Methyl



数据库引用编号

16 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)

62 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]
  • Arturo Morales, Susana Marmesat, M Carmen Dobarganes, Gloria Márquez-Ruiz, Joaquín Velasco. Evaporative light scattering detector in normal-phase high-performance liquid chromatography determination of FAME oxidation products. Journal of chromatography. A. 2012 Sep; 1254(?):62-70. doi: 10.1016/j.chroma.2012.07.028. [PMID: 22840820]
  • Xiaoqing Cai, Omar M Khdour, Jennifer Jaruvangsanti, Sidney M Hecht. Simplified bicyclic pyridinol analogues protect mitochondrial function. Bioorganic & medicinal chemistry. 2012 Jun; 20(11):3584-95. doi: 10.1016/j.bmc.2012.03.075. [PMID: 22560834]
  • Mizuki Takashima, Mototada Shichiri, Yoshihisa Hagihara, Yasukazu Yoshida, Etsuo Niki. Reactivity toward oxygen radicals and antioxidant action of thiol compounds. BioFactors (Oxford, England). 2012 May; 38(3):240-8. doi: 10.1002/biof.1014. [PMID: 22488889]
  • Marja Kähkönen, Petri Kylli, Velimatti Ollilainen, Juha-Pekka Salminen, Marina Heinonen. Antioxidant activity of isolated ellagitannins from red raspberries and cloudberries. Journal of agricultural and food chemistry. 2012 Feb; 60(5):1167-74. doi: 10.1021/jf203431g. [PMID: 22229937]
  • Yang Liu, Huai-feng Yi, Yu Chen, Yu-long Wu, Ming-de Yang, Zeng Chen, Jun-mao Tong. [Column chromatography purification and analysis of biodiesel by transesterification]. Guang pu xue yu guang pu fen xi = Guang pu. 2012 Feb; 32(2):505-9. doi: ". [PMID: 22512199]
  • 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]
  • 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]
  • Geórgia de Sousa Ferreira Soares, Vinicius de Morais Gomes, Anderson Dos Reis Albuquerque, Manoel Barbosa Dantas, Raul Rosenhain, Antônio Gouveia de Souza, Darlene Camati Persunh, Carlos Alberto de Almeida Gadelha, Maria José de Carvalho Costa, Tatiane Santi Gadelha. Spectroscopic and thermooxidative analysis of organic okra oil and seeds from Abelmoschus esculentus. TheScientificWorldJournal. 2012; 2012(?):847471. doi: 10.1100/2012/847471. [PMID: 22645459]
  • 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]
  • Hugo J de Boer, Vichith Lamxay, Lars Björk. Steam sauna and mother roasting in Lao PDR: practices and chemical constituents of essential oils of plant species used in postpartum recovery. BMC complementary and alternative medicine. 2011 Dec; 11(?):128. doi: 10.1186/1472-6882-11-128. [PMID: 22171719]
  • Pratibha Nand, Sushma Drabu, Rajinder K Gupta. Antimicrobial investigation of Linum usitatissimum for the treatment of acne. Natural product communications. 2011 Nov; 6(11):1701-4. doi: . [PMID: 22224292]
  • Anat Elmann, Sharon Mordechay, Hilla Erlank, Alona Telerman, Miriam Rindner, Rivka Ofir. Anti-neuroinflammatory effects of the extract of Achillea fragrantissima. BMC complementary and alternative medicine. 2011 Oct; 11(?):98. doi: 10.1186/1472-6882-11-98. [PMID: 22018032]
  • 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]
  • Konstantia Graikou, Suzanne Kapeta, Nektarios Aligiannis, George Sotiroudis, Niki Chondrogianni, Efstathios Gonos, Ioanna Chinou. Chemical analysis of Greek pollen - Antioxidant, antimicrobial and proteasome activation properties. Chemistry Central journal. 2011 Jun; 5(1):33. doi: 10.1186/1752-153x-5-33. [PMID: 21699688]
  • An Philippaerts, Steven Goossens, Pierre A Jacobs, Bert F Sels. Catalytic production of conjugated fatty acids and oils. ChemSusChem. 2011 Jun; 4(6):684-702. doi: 10.1002/cssc.201100086. [PMID: 21634014]
  • 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]
  • Jinyun Yuan, Zuozuo Ai, Zhibin Zhang, Riming Yan, Qinggui Zeng, Du Zhu. [Microbial oil production by Trichosporon cutaneum B3 using cassava starch]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2011 Mar; 27(3):453-60. doi: ". [PMID: 21650027]
  • Mohamed Farag, Mohamed H M Ahmed, Heba Yousef, Adel A H Abdel-Rahman. Repellent and insecticidal activities of Melia azedarach L. against cotton leafworm, Spodoptera littoralis (Boisd.). Zeitschrift fur Naturforschung. C, Journal of biosciences. 2011 Mar; 66(3-4):129-35. doi: 10.1515/znc-2011-3-406. [PMID: 21630586]
  • 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]
  • Rafik Balti, Ali Bougatef, Nedra El Hadj Ali, Naourez Ktari, Kemel Jellouli, Naima Nedjar-Arroume, Pascal Dhulster, Moncef Nasri. Comparative Study on Biochemical Properties and Antioxidative Activity of Cuttlefish (Sepia officinalis) Protein Hydrolysates Produced by Alcalase and Bacillus licheniformis NH1 Proteases. Journal of amino acids. 2011; 2011(?):107179. doi: 10.4061/2011/107179. [PMID: 22312455]
  • Juan Peng, Jian-Ping Yuan, Chou-Fei Wu, Jiang-Hai Wang. Fucoxanthin, a marine carotenoid present in brown seaweeds and diatoms: metabolism and bioactivities relevant to human health. Marine drugs. 2011; 9(10):1806-1828. doi: 10.3390/md9101806. [PMID: 22072997]
  • 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]
  • Atnan Uğur, Ipek Süntar, Sinem Aslan, Ilkay Erdoğan Orhan, Murat Kartal, Nazim Sekeroğlu, Dursun Eşiyok, Bilge Sener. Variations in fatty acid compositions of the seed oil of Eruca sativa Mill. caused by different sowing periods and nitrogen forms. Pharmacognosy magazine. 2010 Oct; 6(24):305-8. doi: 10.4103/0973-1296.71801. [PMID: 21120033]
  • Jean Soon Park, Hong Wook Kim, Bridget D Mathison, Michael G Hayek, Stefan Massimino, Gregory A Reinhart, Boon P Chew. Astaxanthin uptake in domestic dogs and cats. Nutrition & metabolism. 2010 Jun; 7(?):52. doi: 10.1186/1743-7075-7-52. [PMID: 20565958]
  • Teresa Domínguez, M Luisa Hernández, Joyce C Pennycooke, Pedro Jiménez, José Manuel Martínez-Rivas, Carlos Sanz, Eric J Stockinger, José J Sánchez-Serrano, Maite Sanmartín. Increasing omega-3 desaturase expression in tomato results in altered aroma profile and enhanced resistance to cold stress. Plant physiology. 2010 Jun; 153(2):655-65. doi: 10.1104/pp.110.154815. [PMID: 20382895]
  • Kevin Huvaere, Daniel R Cardoso, Paula Homem-de-Mello, Signe Westermann, Leif H Skibsted. Light-induced oxidation of unsaturated lipids as sensitized by flavins. The journal of physical chemistry. B. 2010 Apr; 114(16):5583-93. doi: 10.1021/jp9121744. [PMID: 20377218]
  • 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]
  • Emilie Combet, Tom Preston, Kenneth E L McColl. Development of an in vitro system combining aqueous and lipid phases as a tool to understand gastric nitrosation. Rapid communications in mass spectrometry : RCM. 2010 Mar; 24(5):529-34. doi: 10.1002/rcm.4388. [PMID: 20112267]
  • 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]
  • Claudia Giuliani, Roberto Maria Pellegrino, Bruno Tirillini, Laura Maleci Bini. The role of secreting structures position on the leaf volatile organic compounds of Hypericum androsaemum. Natural product communications. 2010 Jan; 5(1):107-10. doi: . [PMID: 20184033]
  • 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]
  • Mohd Suhail, Safia Suhail, Bharat Kumar Gupta, Vinay Bharat. Malondialdehyde and Antioxidant Enzymes in Maternal and Cord Blood, and their Correlation in Normotensive and Preeclamptic Women. Journal of clinical medicine research. 2009 Aug; 1(3):150-7. doi: 10.4021/jocmr2009.07.1252. [PMID: 22493649]
  • Songhee Jeon, Nan-Hyung Kim, Byung-Soo Koo, Ji-Young Kim, Ai-Young Lee. Lotus (Nelumbo nuficera) flower essential oil increased melanogenesis in normal human melanocytes. Experimental & molecular medicine. 2009 Jul; 41(7):517-25. doi: 10.3858/emm.2009.41.7.057. [PMID: 19322028]
  • 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]
  • Vitaly A Roginsky, Vadim N Tashlitsky, Vladimir P Skulachev. Chain-breaking antioxidant activity of reduced forms of mitochondria-targeted quinones, a novel type of geroprotectors. Aging. 2009 May; 1(5):481-9. doi: 10.18632/aging.100049. [PMID: 20195487]
  • Chenxi Zhao, Yingxu Zeng, Mingzhu Wan, Rongxi Li, Yizeng Liang, Chengyong Li, Zhongda Zeng, Foo-Tim Chau. Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods. Journal of separation science. 2009 Feb; 32(4):660-70. doi: 10.1002/jssc.200800484. [PMID: 19212980]
  • Bassie B Marvey. Extrudate versus powder silica alumina as support for Re₂O₇ catalyst in the metathesis of seed oil-derivatives - a comparison. International journal of molecular sciences. 2009 Jan; 10(1):213-220. doi: 10.3390/ijms10010213. [PMID: 19333442]
  • 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]
  • Takafumi Hara, Akira Hirasawa, Qi Sun, Taka-aki Koshimizu, Chisato Itsubo, Keiko Sadakane, Takeo Awaji, Gozoh Tsujimoto. Flow cytometry-based binding assay for GPR40 (FFAR1; free fatty acid receptor 1). Molecular pharmacology. 2009 Jan; 75(1):85-91. doi: 10.1124/mol.108.052225. [PMID: 18927207]
  • Luisa Tesoriere, Marco Fazzari, Francesa Angileri, Carla Gentile, Maria A Livrea. In vitro digestion of betalainic foods. Stability and bioaccessibility of betaxanthins and betacyanins and antioxidative potential of food digesta. Journal of agricultural and food chemistry. 2008 Nov; 56(22):10487-92. doi: 10.1021/jf8017172. [PMID: 18959410]
  • Jessica Barillari, Renato Iori, Alessio Papi, Marina Orlandi, Giovanna Bartolini, Simone Gabbanini, Gian Franco Pedulli, Luca Valgimigli. Kaiware Daikon (Raphanus sativus L.) extract: a naturally multipotent chemopreventive agent. Journal of agricultural and food chemistry. 2008 Sep; 56(17):7823-30. doi: 10.1021/jf8011213. [PMID: 18665601]
  • 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]
  • Rabia Alghazeer, Hongliang Gao, Nazlin K Howell. Cytotoxicity of oxidised lipids in cultured colonal human intestinal cancer cells (caco-2 cells). Toxicology letters. 2008 Aug; 180(3):202-11. doi: 10.1016/j.toxlet.2008.06.859. [PMID: 18625293]
  • Rosario Zamora, Francisco J Hidalgo. Contribution of lipid oxidation products to acrylamide formation in model systems. Journal of agricultural and food chemistry. 2008 Aug; 56(15):6075-80. doi: 10.1021/jf073047d. [PMID: 18624449]
  • Mathieu Frenette, Juan C Scaiano. Evidence for hydroxyl radical generation during lipid (linoleate) peroxidation. Journal of the American Chemical Society. 2008 Jul; 130(30):9634-5. doi: 10.1021/ja801858e. [PMID: 18597469]
  • 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]
  • Grazyna Wejnerowska, Alicja Gackowska, Jerzy Gaca. Determination of linoleic acid in toothpaste by gas chromatography with flame ionization detection. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2008 Jun; 24(6):759-62. doi: 10.2116/analsci.24.759. [PMID: 18544865]
  • Jyunichi Kawata, Munekazu Kameda, Mitsuo Miyazawa. Cyclooxygenase-2 inhibitory effects and composition of the volatile oil from the dried roots of Lithospermum erythrorhizon. Journal of natural medicines. 2008 Apr; 62(2):239-43. doi: 10.1007/s11418-007-0221-0. [PMID: 18404332]
  • 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]
  • Zhiqiang Pan, Ameeta K Agarwal, Tao Xu, Qin Feng, Scott R Baerson, Stephen O Duke, Agnes M Rimando. Identification of molecular pathways affected by pterostilbene, a natural dimethylether analog of resveratrol. BMC medical genomics. 2008 Mar; 1(?):7. doi: 10.1186/1755-8794-1-7. [PMID: 18366703]
  • Ji Young Choi, Eun Hyang Choi, Hee Wook Jung, Joon Seok Oh, Won-Hee Lee, Jong Gu Lee, Jong-Keun Son, Youngsoo Kim, Seung Ho Lee. Melanogenesis inhibitory compounds from Saussureae Radix. Archives of pharmacal research. 2008 Mar; 31(3):294-9. doi: 10.1007/s12272-001-1154-0. [PMID: 18409040]
  • 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]
  • L Tesoriere, D Butera, C Gentile, M A Livrea. Bioactive components of caper (Capparis spinosa L.) from Sicily and antioxidant effects in a red meat simulated gastric digestion. Journal of agricultural and food chemistry. 2007 Oct; 55(21):8465-71. doi: 10.1021/jf0714113. [PMID: 17887802]
  • 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]
  • Mahiran Basri, Raja Noor Zaliha Raja Abd Rahman, Afshin Ebrahimpour, Abu Bakar Salleh, Erin Ryantin Gunawan, Mohd Basyaruddin Abd Rahman. Comparison of estimation capabilities of response surface methodology (RSM) with artificial neural network (ANN) in lipase-catalyzed synthesis of palm-based wax ester. BMC biotechnology. 2007 Aug; 7(?):53. doi: 10.1186/1472-6750-7-53. [PMID: 17760990]
  • Patricia D MacLean, Emily C Drake, L Ross, C Barclay. Bilirubin as an antioxidant in micelles and lipid bilayers: its contribution to the total antioxidant capacity of human blood plasma. Free radical biology & medicine. 2007 Aug; 43(4):600-9. doi: 10.1016/j.freeradbiomed.2007.05.020. [PMID: 17640570]
  • 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]
  • Diógenes Herreño Sáenz, Qingsu Xia, Peter P Fu. UVA photoirradiation of methylated benzo[a]pyrene and benzo[e]pyrene leading to induction of lipid peroxidation. International journal of environmental research and public health. 2007 Jun; 4(2):153-7. doi: 10.3390/ijerph2007040010. [PMID: 17617679]
  • Hui-Chan Chen, Qingsu Xia, Shu-Hui Cherng, Shoujun Chen, Ching-Cheng Lai, Hongtao Yu, Peter P Fu. Synthesis and photoirradiation of isomeric ethylchrysenes by UVA light leading to lipid peroxidation. International journal of environmental research and public health. 2007 Jun; 4(2):145-52. doi: 10.3390/ijerph2007040009. [PMID: 17617678]
  • 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]
  • Dongmei Yin, Dangqun Cui, Bin Jia. Construction of a high-efficient expression vector of Delta12 fatty acid desaturase in peanut and its prokaryotical expression. Journal of genetics and genomics = Yi chuan xue bao. 2007 Jan; 34(1):81-8. doi: 10.1016/s1673-8527(07)60009-5. [PMID: 17469780]
  • Muhammad Ishtiaq Ch, Yang F Wen, YiYu Cheng. Gas chromatographic/mass spectrometric analysis of the essential oil of Houttuynia cordata Thunb by using on-column methylation with tetramethylammonium acetate. Journal of AOAC International. 2007 Jan; 90(1):60-7. doi: . [PMID: 17373437]
  • 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]
  • Jianqin Jiang, Yanfang Li, Zhen Chen, Zhida Min, Fengchang Lou. Two novel C29-5beta-sterols from the stems of Opuntia dillenii. Steroids. 2006 Dec; 71(13-14):1073-7. doi: 10.1016/j.steroids.2006.09.005. [PMID: 17112557]
  • Abdelkarim Abousalham, Robert Verger. Continuous measurement of the lipoxygenase-catalyzed oxidation of unsaturated lipids using the monomolecular film technique. Pharmaceutical research. 2006 Oct; 23(10):2469-74. doi: 10.1007/s11095-006-9081-7. [PMID: 16933093]
  • 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]
  • 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 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]
  • Tram Ngoc Ly, Makoto Shimoyamada, Ryo Yamauchi. Isolation and characterization of rosmarinic acid oligomers in Celastrus hindsii Benth leaves and their antioxidative activity. Journal of agricultural and food chemistry. 2006 May; 54(11):3786-93. doi: 10.1021/jf052743f. [PMID: 16719497]
  • M P Germanò, V D'Angelo, T Biasini, R Sanogo, R De Pasquale, S Catania. Evaluation of the antioxidant properties and bioavailability of free and bound phenolic acids from Trichilia emetica Vahl. Journal of ethnopharmacology. 2006 May; 105(3):368-73. doi: 10.1016/j.jep.2005.11.029. [PMID: 16427228]
  • 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]
  • Qingsu Xia, Ming W Chou, Jun J Yin, Paul C Howard, Hongtao Yu, Peter P Fu. Photoirradiation of representative polycyclic aromatic hydrocarbons and twelve isomeric methylbenz[a]anthracene with UVA light: formation of lipid peroxidation. Toxicology and industrial health. 2006 May; 22(4):147-56. doi: 10.1191/0748233706th259oa. [PMID: 16786836]
  • Jie Yang, Martha D Morton, Dennis W Hill, David F Grant. NMR and HPLC-MS/MS analysis of synthetically prepared linoleic acid diol glucuronides. Chemistry and physics of lipids. 2006 Apr; 140(1-2):75-87. doi: 10.1016/j.chemphyslip.2006.01.007. [PMID: 16500631]
  • Markus M Zimmer, Johannes Frank, John H Barker, Hans Becker. Effect of extracts from the Chinese and European mole cricket on wound epithelialization and neovascularization: in vivo studies in the hairless mouse ear wound model. Wound repair and regeneration : official publication of the Wound Healing Society [and] the European Tissue Repair Society. 2006 Mar; 14(2):142-51. doi: 10.1111/j.1743-6109.2006.00104.x. [PMID: 16630103]
  • 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]
  • Leif-Alexander Garbe, Roberto Barbosa de Almeida, Renate Nagel, Karl Wackerbauer, Roland Tressl. Dual positional and stereospecificity of lipoxygenase isoenzymes from germinating barley (green malt): biotransformation of free and esterified linoleic acid. Journal of agricultural and food chemistry. 2006 Feb; 54(3):946-55. doi: 10.1021/jf051993t. [PMID: 16448207]
  • Kuo-Feng Hua, Hsien-Yeh Hsu, Yu-Chang Su, I-Fan Lin, Su-Sing Yang, Ya-Mai Chen, Louis Kuoping Chao. Study on the antiinflammatory activity of methanol extract from seagrass Zostera japonica. Journal of agricultural and food chemistry. 2006 Jan; 54(2):306-11. doi: 10.1021/jf0509658. [PMID: 16417284]
  • 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]