TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (BioDeep_00000017444)

 

Secondary id: BioDeep_00000872115

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


1-(9Z,12Z-Octadecadienoyl)-2-(9Z,12Z-octadecadienoyl)-3-(9Z,12Z-octadecadienoyl)-glycerol

化学式: C57H98O6 (878.7363008)
中文名称: 甘油三亚油酸酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 9.09%

分子结构信息

SMILES: C(OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)[C@]([H])(OC(CCCCCCC/C=C\C/C=C\CCCCC)=O)COC(CCCCCCC/C=C\C/C=C\CCCCC)=O
InChI: InChI=1S/C57H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h16-21,25-30,54H,4-15,22-24,31-53H2,1-3H3/b19-16-,20-17-,21-18-,28-25-,29-26-,30-27-

描述信息

TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is a trilinoleic acid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid tri-esters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position, one chain of linoleic acid at the C-2 position and one chain of linoleic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.
1,2,3-trilinoleoylglycerol is a triglyceride formed by acylation of the three hydroxy groups of glycerol with linoleic acid. It has a role as a mouse metabolite. It is a triglyceride, a TG(18:2/18:2/18:2) and a linoleoyl containing 1,2,3-triacyl-sn-glycerol. It is functionally related to a linoleic acid.
Trilinolein is a natural product found in Lysiphlebia japonica, Phoradendron reichenbachianum, and other organisms with data available.
See also: Coix lacryma-jobi seed (part of).
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors
Trilinolein is an endogenous metabolite.
Trilinolein is an endogenous metabolite.

同义名列表

68 个代谢物同义名

1-(9Z,12Z-Octadecadienoyl)-2-(9Z,12Z-octadecadienoyl)-3-(9Z,12Z-octadecadienoyl)-glycerol; 1,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate; 2,3-bis[[(9Z,12Z)-octadeca-9,12-dienoyl]oxy]propyl (9Z,12Z)-octadeca-9,12-dienoate; 2,3-Bis[(9Z,12Z)-9,12-octadecadienoyloxy]propyl (9Z,12Z)-9,12-octadecadienoate #; Propane-1,2,3-triyl (9Z,9Z,9Z,12Z,12Z,12Z)-tris(octadeca-9,12-dienoate); propane-1,2,3-triyl (9Z,12Z,9Z,12Z,9Z,12Z)tris-octadeca-9,12-dienoate; 9,12-OCTADECADIENOIC ACID (9Z,12Z)-, 1,1,1-(1,2,3-PROPANETRIYL) ESTER; 9,12-Octadecadienoic acid (9Z,12Z)-, 1,2,3-propanetriyl ester; 9,12-Octadecadienoic acid (Z,Z)-, 1,2,3-propanetriyl ester; (Z,Z)-9,12-Octadecadienoic acid, 1,2,3-propanetriyl ester; Propane-1,2,3-triyl tris((9Z,12Z)-octadeca-9,12-dienoate); 9,12-Octadecadienoic acid, 1,2,3-propanetriyl ester; 1,2,3-Propenetriol tri(9,12-octadecadienoic acid); 1,2,3-Tri-(cis,cis-9,12-octadecadienoyl)glycerol; 1,2,3-Tri(cis,cis-9,12-octadecadienoyl) Glycerol; Tracylglycerol(18:2omega6/18:2omega6/18:2omega6); TG [18:2(omega-6)/18:2(omega-6)/18:2(omega-6)]; 1,2,3-Propenetriol tri(9,12-octadecadienoate); 1,2,3-Propenetriol tri(9,12-octadecaienoate); 1-linoleoyl-2-linoleoyl-3-linoleoyl-glycerol; Glyceryl trilinoleate, >=98\\% (TLC), liquid; 1,2,3-tri-(9Z,12Z-octadecadienoyl)-glycerol; 1,2,3-tri-(9Z,12Z)-octadecadienoylglycerol; Glyceryl trilinoleate, analytical standard; 1,2,3-tri-(9Z,12Z-octadecadienoyl)glycerol; TG(18:2(9Z,12Z)/18:2(9Z,12Z)/18:2(9Z,12Z)); Linoleic acid, 1,2,3-propanetriyl ester; TG(18:2omega6/18:2omega6/18:2omega6); Tracylglycerol(18:2n6/18:2n6/18:2n6); Tracylglycerol(18:2w6/18:2w6/18:2w6); 1,2,3-Propanetriol trilinoleic acid; Glycerol Tri-9,12-octadecadienoate; 1,2,3-Propanetriol trilinoleate; Triacylglycerol(18:2/18:2/18:2); Tracylglycerol(18:2/18:2/18:2); trilinolein, (all-E)-isomer; 1,2,3-Trilinoleoylglycerol; TAG(18:2n6/18:2n6/18:2n6); TAG(18:2w6/18:2w6/18:2w6); Glyceryl trilinoleic acid; TG(18:2n6/18:2n6/18:2n6); TG(18:2w6/18:2w6/18:2w6); linoleoyl triglyceride; Glyceryl trilinoleate; Triacylglycerol(54:6); glycerol trilinoleate; Tracylglycerol(54:6); trilinoleic glycerol; TAG(18:2/18:2/18:2); TG(18:2/18:2/18:2); TRILINOLEIN [INCI]; TG 18:2_18:2_18:2; trilinolein C18:2; Triacylglycerol; trilinoelaidate; Trilinolelaidin; UNII-V5LJ52OGS7; LINOLEIN, TRI-; trilinoelaidin; Triglyceride; Trilinolein; EFADERMA-F; V5LJ52OGS7; TAG(54:6); TG(54:6); TG 54:6; TG; Linolein



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

7 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(7)

PharmGKB(0)

51 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

  • Xianghong Lin, Na Deng, Huijuan Li, Jingxian Duan, Wenqiu Chen, Tao Liu, Sujiao Sun, Jimin Chu. The skin photoprotective effect of trilinolein: Induction of cellular autophagy via the AMPK-mTOR signaling pathway. Toxicology and applied pharmacology. 2024 02; 483(?):116836. doi: 10.1016/j.taap.2024.116836. [PMID: 38272316]
  • Marie-José Vallier, Carine Le Bourvellec, Olivier Dangles. Iron-induced peroxidation of trilinolein nano-emulsions under model gastric conditions and its inhibition by dietary phenolic antioxidants. Food & function. 2020 Oct; 11(10):9144-9156. doi: 10.1039/d0fo01767a. [PMID: 33026020]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
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  • Michael Stephany, Stephanie Bader-Mittermaier, Ute Schweiggert-Weisz, Reinhold Carle. Lipoxygenase activity in different species of sweet lupin (Lupinus L.) seeds and flakes. Food chemistry. 2015 May; 174(?):400-6. doi: 10.1016/j.foodchem.2014.11.029. [PMID: 25529698]
  • Fuki Kitamura, Hiroyuki Watanabe, Aya Umeno, Yasukazu Yoshida, Kenji Kurata, Naohiro Gotoh. Oxidized trilinoleate and tridocosahexaenoate induce pica behavior and change locomotor activity. Journal of oleo science. 2013; 62(4):207-12. doi: 10.5650/jos.62.207. [PMID: 23535307]
  • Fabiola De Marchi, Roberta Seraglia, Laura Molin, Pietro Traldi, Mirko De Rosso, Annarita Panighel, Antonio Dalla Vedova, Massimo Gardiman, Mirella Giust, Riccardo Flamini. Seed oil triglyceride profiling of thirty-two hybrid grape varieties. Journal of mass spectrometry : JMS. 2012 Sep; 47(9):1113-9. doi: 10.1002/jms.3010. [PMID: 22972779]
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  • Kuen-Daw Tsai, Shu-Mei Yang, Jen-Chih Lee, Ho-Yiu Wong, Chuen-Ming Shih, Ting-Hui Lin, Min-Jen Tseng, Wei Chen. Panax notoginseng Attenuates Bleomycin-Induced Pulmonary Fibrosis in Mice. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):404761. doi: 10.1155/2011/404761. [PMID: 21423633]
  • Pei-Yu Chou, Guan-Jhong Huang, Chun-Hsu Pan, Yi-Chung Chien, Ying-Yi Chen, Chieh-Hsi Wu, Ming-Jyh Sheu, Hsu-Chen Cheng. Trilinolein inhibits proliferation of human non-small cell lung carcinoma A549 through the modulation of PI3K/Akt pathway. The American journal of Chinese medicine. 2011; 39(4):803-15. doi: 10.1142/s0192415x11009214. [PMID: 21721158]
  • Maike Rudolph, Armin Schlereth, Martina Körner, Kirstin Feussner, Ekkehardt Berndt, Michael Melzer, Ellen Hornung, Ivo Feussner. The lipoxygenase-dependent oxygenation of lipid body membranes is promoted by a patatin-type phospholipase in cucumber cotyledons. Journal of experimental botany. 2011 Jan; 62(2):749-60. doi: 10.1093/jxb/erq310. [PMID: 21081663]
  • Christopher J Pynn, M Victoria Picardi, Tim Nicholson, Dorothee Wistuba, Christian F Poets, Erwin Schleicher, Jesus Perez-Gil, Wolfgang Bernhard. Myristate is selectively incorporated into surfactant and decreases dipalmitoylphosphatidylcholine without functional impairment. American journal of physiology. Regulatory, integrative and comparative physiology. 2010 Nov; 299(5):R1306-16. doi: 10.1152/ajpregu.00380.2010. [PMID: 20811010]
  • 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]
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  • Rodrigo Maestre, Manuel Pazos, Isabel Medina. Involvement of methemoglobin (MetHb) formation and hemin loss in the pro-oxidant activity of fish hemoglobins. Journal of agricultural and food chemistry. 2009 Aug; 57(15):7013-21. doi: 10.1021/jf9006664. [PMID: 19722582]
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  • Atsushi Naito, Tatsuyuki Midorikawa, Teruhiko Yoshino, Motoyasu Ohdera. Lipid peroxides induce early onset of catagen phase in murine hair cycles. International journal of molecular medicine. 2008 Dec; 22(6):725-9. doi: 10.3892/ijmm_00000078. [PMID: 19020769]
  • Ying Xu, Zeng-Jun Guo, Lin Tan, Ming-Zhe Zhou. [Analysis of petroleum fraction of Aconitum taipeicum by GC-MS]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2008 Nov; 31(11):1659-61. doi: ". [PMID: 19260273]
  • Jimin Ren, Ivan Dimitrov, A Dean Sherry, Craig R Malloy. Composition of adipose tissue and marrow fat in humans by 1H NMR at 7 Tesla. Journal of lipid research. 2008 Sep; 49(9):2055-62. doi: 10.1194/jlr.d800010-jlr200. [PMID: 18509197]
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  • Hung-Yu Yang, Ju-Chi Liu, Yen-Ling Chen, Cheng-Hsien Chen, Heng Lin, Jia-Wei Lin, Wen-Ta Chiu, Jin-Jer Chen, Tzu-Hurng Cheng. Inhibitory effect of trilinolein on endothelin-1-induced c-fos gene expression in cultured neonatal rat cardiomyocytes. Naunyn-Schmiedeberg's archives of pharmacology. 2005 Aug; 372(2):160-7. doi: 10.1007/s00210-005-0003-8. [PMID: 16184402]
  • Shi-Chung Chen, Jun-Jack Cheng, Ming-Hsiung Hsieh, Yen-Ling Chu, Pai-Feng Kao, Tzu-Hurng Cheng, Paul Chan. Molecular mechanism of the inhibitory effect of trilinolein on endothelin-1-induced hypertrophy of cultured neonatal rat cardiomyocytes. Planta medica. 2005 Jun; 71(6):525-9. doi: 10.1055/s-2005-864153. [PMID: 15971123]
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