Punicic acid (BioDeep_00000002820)

Main id: BioDeep_00000000717

 

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds natural product


代谢物信息卡片


cis-9, trans-11, trans-13-octadecatrienoic acid

化学式: C18H30O2 (278.224568)
中文名称: (Z,E,Z)-9,11,13-十八碳三烯酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C(=O)(O)CCCCCCC/C=C\C=C\C=C\CCCC
InChI: InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7+,10-9-

描述信息

alpha-Eleostearic acid is found in bitter gourd. alpha-Eleostearic acid is isolated from seed oil of Momordica charantia (bitter melon
Isolated from seed oil of Momordica charantia (bitter melon). alpha-Eleostearic acid is found in bitter gourd and fruits.

同义名列表

55 个代谢物同义名

cis-9, trans-11, trans-13-octadecatrienoic acid; 9cis,11trans,13trans-Conjugated linolenic acid; 9-trans,11-cis,13-trans-Octadecatrienoic acid; (9E,11Z,13E)-octadeca-9,11,13-trienoic acid; cis-9,trans-11,cis-13-Octadecatrienoic acid; 9trans,11-cis,13trans-Octadecatrienoic acid; (9Z,11E,13Z)-octadeca-9,11,13-trienoic acid; (9E,11Z,13E)-9,11,13-Octadecatrienoic acid; 9-trans,11-cis,13-trans-Octadecatrienoate; 9trans,11-cis,13trans-Octadecatrienoate; (9E,11Z,13E)-9,11,13-Octadecatrienoate; 9(Z),11(E),13(Z)-OCTADECATRIENOIC ACID; (e,Z,e)-9,11,13-Octadecatrienoic acid; 9t,11C,13t-Conjugated linolenic acid; t9,C11,t13-Conjugated linolenic acid; 9,11,13-Conjugated linolenic acid; Octadeca-9t,11C,13t-trienoic acid; (e,Z,e)-9,11,13-Octadecatrienoate; Eleostearic acid, (Z,e,e)-isomer; t9,C11,t13-Conjugated linolenate; Eleostearic acid, (e,Z,e)-isomer; 9Z,11E,13E-octadecatrienoic acid; Eleostearic acid, (e,e,e)-isomer; Eleostearic acid, (Z,Z,e)-isomer; 9t,11C,13t-Conjugated linolenate; C18:3 N-5 trans, 7 cis, 9 trans; Octadeca-9t,11C,13t-triensaeure; 9,11,13-Octadecatrienoic acid; Octadeca-9t,11C,13t-trienoate; 9E,11Z,13E-Octadecatrienoate; t9,C11,t13-Linolenic acid; 9t,11C,13t-Linolenic acid; α-Eleostearic Acid; alpha-Eleostearic acid; 9t,11C,13t-Linolenate; t9,C11,t13-Linolenate; a-Eleostearic acid; Α-eleostearic acid; alpha-Eleostearate; Trichosanic acid; Eleostearic acid; t9,C11,t13-CLnA; 9t,11C,13t-CLnA; 9t,11C,13t-CLN; 9C,11t,13t-CLN; Α-eleostearate; a-Eleostearate; Punicinic acid; t9,C11,t13-CLN; Punicic acid; α-ESA; 9,11,13-CLN; Punicate; Punicic acid; (9Z,11E,13E)-Octadecatrienoic acid



数据库引用编号

26 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)

41 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

  • Zarrin Basharat, Zainab Murtaza, Aisha Siddiqa, Sulaiman Mohammed Alnasser, Alotaibi Meshal. Therapeutic target mapping from the genome of Kingella negevensis and biophysical inhibition assessment through PNP synthase binding with traditional medicinal compounds. Molecular diversity. 2024 Apr; 28(2):581-594. doi: 10.1007/s11030-023-10604-y. [PMID: 36645537]
  • Lingling Zhang, Pan Wu, Wenying Li, Tao Feng, Jay Shockey, Liang Chen, Lin Zhang, Shiyou Lü. Triacylglycerol biosynthesis in shaded seeds of tung tree (Vernicia fordii) is regulated in part by Homeodomain Leucine Zipper 21. The Plant journal : for cell and molecular biology. 2021 12; 108(6):1735-1753. doi: 10.1111/tpj.15540. [PMID: 34643970]
  • Alexander Beatty, Tanu Singh, Yulia Y Tyurina, Vladimir A Tyurin, Svetlana Samovich, Emmanuelle Nicolas, Kristen Maslar, Yan Zhou, Kathy Q Cai, Yinfei Tan, Sebastian Doll, Marcus Conrad, Aravind Subramanian, Hülya Bayır, Valerian E Kagan, Ulrike Rennefahrt, Jeffrey R Peterson. Ferroptotic cell death triggered by conjugated linolenic acids is mediated by ACSL1. Nature communications. 2021 04; 12(1):2244. doi: 10.1038/s41467-021-22471-y. [PMID: 33854057]
  • Debjyoti Paul, Krishnendu Manna, Aaveri Sengupta, Sayani Mukherjee, Sanjit Dey, Prasanta K Bag, Pubali Dhar. A novel nanoformulation of α-eleostearic acid restores molecular pathogenesis of hypersensitivity. Nanomedicine (London, England). 2019 03; 14(5):529-552. doi: 10.2217/nnm-2018-0450. [PMID: 30753111]
  • Anura P Jayasooriya. How to safeguard an appropriate "all trans retinoic acid" concentration to keep cell division on track: Exploring therapeutic hotspots from metabolomics. Medical hypotheses. 2018 Dec; 121(?):56. doi: 10.1016/j.mehy.2018.09.020. [PMID: 30396492]
  • Peng Cui, Qiang Lin, Dongming Fang, Lingling Zhang, Rongjun Li, Junyong Cheng, Fei Gao, Jay Shockey, Songnian Hu, Shiyou Lü. Tung Tree (Vernicia fordii, Hemsl.) Genome and Transcriptome Sequencing Reveals Co-Ordinate Up-Regulation of Fatty Acid β-Oxidation and Triacylglycerol Biosynthesis Pathways During Eleostearic Acid Accumulation in Seeds. Plant & cell physiology. 2018 Oct; 59(10):1990-2003. doi: 10.1093/pcp/pcy117. [PMID: 30137600]
  • Inès Belhaj, Sawsan Amara, Goetz Parsiegla, Priscila Sutto-Ortiz, Moulay Sahaka, Hafedh Belghith, Audric Rousset, Dominique Lafont, Frédéric Carrière. Galactolipase activity of Talaromyces thermophilus lipase on galactolipid micelles, monomolecular films and UV-absorbing surface-coated substrate. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2018 09; 1863(9):1006-1015. doi: 10.1016/j.bbalip.2018.05.016. [PMID: 29859246]
  • Meddy El Alaoui, Laurent Soulère, Alexandre Noiriel, Priscila Sutto-Ortiz, Lucie Grand, Florence Popowycz, Jorge Alberto Rodríguez-González, Yves Queneau, Abdelkarim Abousalham. A Continuous and Sensitive Spectrophotometric Assay for Lipase and Phospholipase A Activities Using α-Eleostearic Acid-Containing Substrates. Methods in molecular biology (Clifton, N.J.). 2018; 1835(?):119-128. doi: 10.1007/978-1-4939-8672-9_5. [PMID: 30109648]
  • Erwann Durand, André Delavault, Claire Bourlieu, Jérôme Lecomte, Bruno Baréa, Maria Cruz Figueroa Espinoza, Eric A Decker, Françoise Michel Salaun, Gilles Kergourlay, Pierre Villeneuve. Eleostearic phospholipids as probes to evaluate antioxidants efficiency against liposomes oxidation. Chemistry and physics of lipids. 2017 12; 209(?):19-28. doi: 10.1016/j.chemphyslip.2017.10.006. [PMID: 29061286]
  • Gou-Chun Chen, Wen-Hung Chen, Kuo-Tang Tseng, Pei-Min Chao. The anti-adiposity effect of bitter melon seed oil is solely attributed to its fatty acid components. Lipids in health and disease. 2017 Sep; 16(1):186. doi: 10.1186/s12944-017-0578-3. [PMID: 28962621]
  • Harold K Abaidoo-Ayin, Prince G Boakye, Kerby C Jones, Victor T Wyatt, Samuel A Besong, Stephen E Lumor. Compositional Analyses and Shelf-Life Modeling of Njangsa (Ricinodendron heudelotii) Seed Oil Using the Weibull Hazard Analysis. Journal of food science. 2017 Aug; 82(8):1799-1806. doi: 10.1111/1750-3841.13767. [PMID: 28631807]
  • Olga Yurchenko, Jay M Shockey, Satinder K Gidda, Maxwell I Silver, Kent D Chapman, Robert T Mullen, John M Dyer. Engineering the production of conjugated fatty acids in Arabidopsis thaliana leaves. Plant biotechnology journal. 2017 Aug; 15(8):1010-1023. doi: 10.1111/pbi.12695. [PMID: 28083898]
  • Ya-Yuan Chang, Hui-Min Su, Szu-Han Chen, Wen-Tsong Hsieh, Jong-Ho Chyuan, Pei-Min Chao. Roles of Peroxisome Proliferator-Activated Receptor α in Bitter Melon Seed Oil-Corrected Lipid Disorders and Conversion of α-Eleostearic Acid into Rumenic Acid in C57BL/6J Mice. Nutrients. 2016 Dec; 8(12):. doi: 10.3390/nu8120805. [PMID: 27973445]
  • Meddy El Alaoui, Laurent Soulère, Alexandre Noiriel, Florence Popowycz, Abdallah Khatib, Yves Queneau, Abdelkarim Abousalham. A continuous spectrophotometric assay that distinguishes between phospholipase A1 and A2 activities. Journal of lipid research. 2016 08; 57(8):1589-97. doi: 10.1194/jlr.d065961. [PMID: 27194811]
  • Gou-Chun Chen, Hui-Min Su, Yu-Shun Lin, Po-Yen Tsou, Jong-Ho Chyuan, Pei-Min Chao. A conjugated fatty acid present at high levels in bitter melon seed favorably affects lipid metabolism in hepatocytes by increasing NAD(+)/NADH ratio and activating PPARα, AMPK and SIRT1 signaling pathway. The Journal of nutritional biochemistry. 2016 07; 33(?):28-35. doi: 10.1016/j.jnutbio.2016.03.009. [PMID: 27260465]
  • Paweł Górnaś, Magdalena Rudzińska, Marianna Raczyk, Inga Mišina, Dalija Segliņa. Impact of Cultivar on Profile and Concentration of Lipophilic Bioactive Compounds in Kernel Oils Recovered from Sweet Cherry (Prunus avium L.) by-Products. Plant foods for human nutrition (Dordrecht, Netherlands). 2016 Jun; 71(2):158-64. doi: 10.1007/s11130-016-0538-5. [PMID: 26984340]
  • Erwann Durand, Yu Zhao, John N Coupland, Ryan J Elias. Assessing Interactions between Lipophilic and Hydrophilic Antioxidants in Food Emulsions. Journal of agricultural and food chemistry. 2015 Dec; 63(49):10655-61. doi: 10.1021/acs.jafc.5b04152. [PMID: 26479322]
  • Meddy El Alaoui, Alexandre Noiriel, Laurent Soulère, Lucie Grand, Yves Queneau, Abdelkarim Abousalham. Development of a high-throughput assay for measuring phospholipase A activity using synthetic 1,2-α-eleostearoyl-sn-glycero-3-phosphocholine coated on microtiter plates. Analytical chemistry. 2014 Nov; 86(21):10576-83. doi: 10.1021/ac502096v. [PMID: 25266374]
  • Hassen Mohamed Sbihi, Imededdine Arbi Nehdi, Saud Ibrahim Al-Resayes. Characterization of white Mahlab (Prunus mahaleb L.) seed oil: a rich source of α-eleostearic acid. Journal of food science. 2014 May; 79(5):C795-801. doi: 10.1111/1750-3841.12467. [PMID: 24754875]
  • Kun Huang, Zengshe Liu, Jinwen Zhang, Shouhai Li, Mei Li, Jianling Xia, Yonghong Zhou. Epoxy monomers derived from tung oil fatty acids and its regulable thermosets cured in two synergistic ways. Biomacromolecules. 2014 Mar; 15(3):837-43. doi: 10.1021/bm4018929. [PMID: 24484324]
  • Q Q Cui, Y C Chen, X J Han, Z Y Zhan, L Y Lin, L L Si, Y D Wang. Expression analysis of VfDGAT2 in various tissues of the tung tree and in transgenic yeast. Genetics and molecular research : GMR. 2013 Dec; 12(4):6554-64. doi: 10.4238/2013.december.11.7. [PMID: 24391002]
  • Robson Simplício de Sousa, Alessandro Oliveira de Moraes Nogueira, Viviane Gobel Marques, Rosilene Maria Clementin, Vânia Rodrigues de Lima. Effects of α-eleostearic acid on asolectin liposomes dynamics: relevance to its antioxidant activity. Bioorganic chemistry. 2013 Dec; 51(?):8-15. doi: 10.1016/j.bioorg.2013.08.004. [PMID: 24076476]
  • Carole Serveau-Avesque, Robert Verger, Jorge A Rodriguez, Abdelkarim Abousalham. Development of a high-throughput assay for measuring lipase activity using natural triacylglycerols coated on microtiter plates. The Analyst. 2013 Sep; 138(18):5230-8. doi: 10.1039/c3an36699e. [PMID: 23851449]
  • S Obitsu, K Sakata, R Teshima, K Kondo. Eleostearic acid induces RIP1-mediated atypical apoptosis in a kinase-independent manner via ERK phosphorylation, ROS generation and mitochondrial dysfunction. Cell death & disease. 2013 Jun; 4(?):e674. doi: 10.1038/cddis.2013.188. [PMID: 23788031]
  • Siddhartha S Saha, Mahua Ghosh. Protective effect of conjugated linolenic acid isomers present in vegetable oils against arsenite-induced renal toxicity in rat model. Nutrition (Burbank, Los Angeles County, Calif.). 2013 Jun; 29(6):903-10. doi: 10.1016/j.nut.2012.12.013. [PMID: 23422533]
  • Steven Pastor, Kandan Sethumadhavan, Abul H J Ullah, Satinder Gidda, Heping Cao, Catherine Mason, Dorselyn Chapital, Brian Scheffler, Robert Mullen, John Dyer, Jay Shockey. Molecular properties of the class III subfamily of acyl-coenyzme A binding proteins from tung tree (Vernicia fordii). Plant science : an international journal of experimental plant biology. 2013 Apr; 203-204(?):79-88. doi: 10.1016/j.plantsci.2012.12.009. [PMID: 23415331]
  • Yuting Tian, Zhenbo Xu, Baodong Zheng, Y Martin Lo. Optimization of ultrasonic-assisted extraction of pomegranate (Punica granatum L.) seed oil. Ultrasonics sonochemistry. 2013 Jan; 20(1):202-8. doi: 10.1016/j.ultsonch.2012.07.010. [PMID: 22964031]
  • Siddhartha S Saha, Pritha Dasgupta, Sumita Sengupta Bandyopadhyay, Mahua Ghosh. Synergistic effect of conjugated linolenic acid isomers against induced oxidative stress, inflammation and erythrocyte membrane disintegrity in rat model. Biochimica et biophysica acta. 2012 Dec; 1820(12):1951-70. doi: 10.1016/j.bbagen.2012.08.021. [PMID: 22967758]
  • Zhongyan Sun, Han Wang, Shuhong Ye, Shan Xiao, Jing Liu, Wenwen Wang, Dandan Jiang, Xiao Liu, Jihui Wang. Beta-eleostearic acid induce apoptosis in T24 human bladder cancer cells through reactive oxygen species (ROS)-mediated pathway. Prostaglandins & other lipid mediators. 2012 Oct; 99(1-2):1-8. doi: 10.1016/j.prostaglandins.2012.04.001. [PMID: 22609276]
  • Siddhartha S Saha, Mahua Ghosh. Antioxidant and anti-inflammatory effect of conjugated linolenic acid isomers against streptozotocin-induced diabetes. The British journal of nutrition. 2012 Sep; 108(6):974-83. doi: 10.1017/s0007114511006325. [PMID: 22182422]
  • Christine F Coursodon-Boyiddle, Chelsea L Snarrenberg, Camille K Adkins-Rieck, Josep Bassaganya-Riera, Raquel Hontecillas, Peter Lawrence, J Thomas Brenna, Zeina E Jouni, Bohuslav Dvorak. Pomegranate seed oil reduces intestinal damage in a rat model of necrotizing enterocolitis. American journal of physiology. Gastrointestinal and liver physiology. 2012 Sep; 303(6):G744-51. doi: 10.1152/ajpgi.00248.2012. [PMID: 22821948]
  • Moumita Pal, M Ghosh. Prophylactic effect of α-linolenic acid and α-eleostearic acid against MeHg induced oxidative stress, DNA damage and structural changes in RBC membrane. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Aug; 50(8):2811-8. doi: 10.1016/j.fct.2012.05.038. [PMID: 22683484]
  • Pei-Hsuan Chen, Gou-Chun Chen, Mei-Fang Yang, Cheng-Hsien Hsieh, Shu-Han Chuang, Hsin-Ling Yang, Yueh-Hsiung Kuo, Jong-Ho Chyuan, Pei-Min Chao. Bitter melon seed oil-attenuated body fat accumulation in diet-induced obese mice is associated with cAMP-dependent protein kinase activation and cell death in white adipose tissue. The Journal of nutrition. 2012 Jul; 142(7):1197-204. doi: 10.3945/jn.112.159939. [PMID: 22623391]
  • Siddhartha S Saha, Anirban Chakraborty, Santinath Ghosh, Mahua Ghosh. Comparative study of hypocholesterolemic and hypolipidemic effects of conjugated linolenic acid isomers against induced biochemical perturbations and aberration in erythrocyte membrane fluidity. European journal of nutrition. 2012 Jun; 51(4):483-95. doi: 10.1007/s00394-011-0233-0. [PMID: 21814874]
  • Richa Rawat, Xiao-Hong Yu, Marie Sweet, John Shanklin. Conjugated fatty acid synthesis: residues 111 and 115 influence product partitioning of Momordica charantia conjugase. The Journal of biological chemistry. 2012 May; 287(20):16230-7. doi: 10.1074/jbc.m111.325316. [PMID: 22451660]
  • Golaleh Asghari, Sara Sheikholeslami, Parvin Mirmiran, Abdolreza Chary, Mehdi Hedayati, Abbas Shafiee, Fereidoun Azizi. Effect of pomegranate seed oil on serum TNF-α level in dyslipidemic patients. International journal of food sciences and nutrition. 2012 May; 63(3):368-71. doi: 10.3109/09637486.2011.631521. [PMID: 22044195]
  • Moumita Pal, M Ghosh. Studies on comparative efficacy of α-linolenic acid and α-eleostearic acid on prevention of organic mercury-induced oxidative stress in kidney and liver of rat. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Mar; 50(3-4):1066-72. doi: 10.1016/j.fct.2011.12.042. [PMID: 22269903]
  • Satoshi Seino, Yurie Tanaka, Taro Honma, Miyuki Yanaka, Kenta Sato, Nahoko Shinohara, Junya Ito, Tsuyoshi Tsuduki, Kiyotaka Nakagawa, Teruo Miyazawa, Ikuo Ikeda. Atopic dermatitis causes lipid accumulation in the liver of NC/Nga mouse. Journal of clinical biochemistry and nutrition. 2012 Mar; 50(2):152-7. doi: 10.3164/jcbn.11-29. [PMID: 22448097]
  • Ching-Shu Lai, Mei-Ling Tsai, Vladimir Badmaev, Miguel Jimenez, Chi-Tang Ho, Min-Hsiung Pan. Xanthigen suppresses preadipocyte differentiation and adipogenesis through down-regulation of PPARγ and C/EBPs and modulation of SIRT-1, AMPK, and FoxO pathways. Journal of agricultural and food chemistry. 2012 Feb; 60(4):1094-101. doi: 10.1021/jf204862d. [PMID: 22224971]
  • Lilia D Mendoza, Jorge A Rodriguez, Julien Leclaire, Gerard Buono, Frédéric Fotiadu, Frédéric Carrière, Abdelkarim Abousalham. An ultraviolet spectrophotometric assay for the screening of sn-2-specific lipases using 1,3-O-dioleoyl-2-O-α-eleostearoyl-sn-glycerol as substrate. Journal of lipid research. 2012 Jan; 53(1):185-94. doi: 10.1194/jlr.d019489. [PMID: 22114038]
  • Anne-Catherine Schneider, Pauline Beguin, Sophie Bourez, James W Perfield, Eric Mignolet, Cathy Debier, Yves-Jacques Schneider, Yvan Larondelle. Conversion of t11t13 CLA into c9t11 CLA in Caco-2 cells and inhibition by sterculic oil. PloS one. 2012; 7(3):e32824. doi: 10.1371/journal.pone.0032824. [PMID: 22427892]
  • Irene O C M Vroegrijk, Janna A van Diepen, Sjoerd van den Berg, Irene Westbroek, Hiskias Keizer, Luisa Gambelli, Raquel Hontecillas, Josep Bassaganya-Riera, Gerben C M Zondag, Johannes A Romijn, Louis M Havekes, Peter J Voshol. Pomegranate seed oil, a rich source of punicic acid, prevents diet-induced obesity and insulin resistance in mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Jun; 49(6):1426-30. doi: 10.1016/j.fct.2011.03.037. [PMID: 21440024]
  • Siddhartha S Saha, Mahua Ghosh. Antioxidant effect of vegetable oils containing conjugated linolenic acid isomers against induced tissue lipid peroxidation and inflammation in rat model. Chemico-biological interactions. 2011 Apr; 190(2-3):109-20. doi: 10.1016/j.cbi.2011.02.030. [PMID: 21382362]
  • Ananthan Padmashree, Gopal K Sharma, Anil D Semwal, Amarinder S Bawa. Studies on the antioxygenic activity of bitter gourd (Momordica charantia) and its fractions using various in vitro models. Journal of the science of food and agriculture. 2011 Mar; 91(4):776-82. doi: 10.1002/jsfa.4251. [PMID: 21302334]
  • Takuji Tanaka, Masashi Hosokawa, Yumiko Yasui, Rikako Ishigamori, Kazuo Miyashita. Cancer chemopreventive ability of conjugated linolenic acids. International journal of molecular sciences. 2011; 12(11):7495-509. doi: 10.3390/ijms12117495. [PMID: 22174613]
  • Josep Bassaganya-Riera, Amir J Guri, Raquel Hontecillas. Treatment of Obesity-Related Complications with Novel Classes of Naturally Occurring PPAR Agonists. Journal of obesity. 2011; 2011(?):897894. doi: 10.1155/2011/897894. [PMID: 21253508]
  • S S Saha, M Ghosh. Ameliorative role of conjugated linolenic acid isomers against oxidative DNA damage induced by sodium arsenite in rat model. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2010 Dec; 48(12):3398-405. doi: 10.1016/j.fct.2010.09.011. [PMID: 20851731]
  • Peizhen Yang, Xiangjun Li, Matthew J Shipp, Jay M Shockey, Edgar B Cahoon. Mining the bitter melon (momordica charantia l.) seed transcriptome by 454 analysis of non-normalized and normalized cDNA populations for conjugated fatty acid metabolism-related genes. BMC plant biology. 2010 Nov; 10(?):250. doi: 10.1186/1471-2229-10-250. [PMID: 21080948]
  • Parvin Mirmiran, Mohammad Reza Fazeli, Golaleh Asghari, Abbas Shafiee, Fereidoun Azizi. Effect of pomegranate seed oil on hyperlipidaemic subjects: a double-blind placebo-controlled clinical trial. The British journal of nutrition. 2010 Aug; 104(3):402-6. doi: 10.1017/s0007114510000504. [PMID: 20334708]
  • Xiao-ru Liu, Ze-yuan Deng, Ya-wei Fan, Jing Li, Zhi-han Liu. [Mineral elements analysis of Momordica charantiap seeds by ICP-AES and fatty acid profile identification of seed oil by GC-MS]. Guang pu xue yu guang pu fen xi = Guang pu. 2010 Aug; 30(8):2265-8. doi: . [PMID: 20939353]
  • Michael E Grossmann, Nancy K Mizuno, Todd Schuster, Margot P Cleary. Punicic acid is an omega-5 fatty acid capable of inhibiting breast cancer proliferation. International journal of oncology. 2010 Feb; 36(2):421-6. doi: . [PMID: 20043077]
  • Hoang Ngoc Ai Tran, Soo-Young Bae, Bang-Ho Song, Bang-Hyo Lee, Young-Seok Bae, Young-Ho Kim, Ephraim Philip Lansky, Robert A Newman. Pomegranate (Punica granatum) seed linolenic acid isomers: concentration-dependent modulation of estrogen receptor activity. Endocrine research. 2010 Jan; 35(1):1-16. doi: 10.3109/07435800903524161. [PMID: 20136514]
  • Garima Pande, Casimir C Akoh. Antioxidant capacity and lipid characterization of six Georgia-grown pomegranate cultivars. Journal of agricultural and food chemistry. 2009 Oct; 57(20):9427-36. doi: 10.1021/jf901880p. [PMID: 19743855]
  • Michael E Grossmann, Nancy K Mizuno, Michelle L Dammen, Todd Schuster, Amitabha Ray, Margot P Cleary. Eleostearic Acid inhibits breast cancer proliferation by means of an oxidation-dependent mechanism. Cancer prevention research (Philadelphia, Pa.). 2009 Oct; 2(10):879-86. doi: 10.1158/1940-6207.capr-09-0088. [PMID: 19789297]
  • Gaofeng Yuan, Andrew J Sinclair, Chaojiong Xu, Duo Li. Incorporation and metabolism of punicic acid in healthy young humans. Molecular nutrition & food research. 2009 Oct; 53(10):1336-42. doi: 10.1002/mnfr.200800520. [PMID: 19753607]
  • S S Saha, M Ghosh. Comparative study of antioxidant activity of alpha-eleostearic acid and punicic acid against oxidative stress generated by sodium arsenite. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Oct; 47(10):2551-6. doi: 10.1016/j.fct.2009.07.012. [PMID: 19619603]
  • Bogdan Smyk, Ryszard Amarowicz, Mariusz Szabelski, Ignacy Gryczynski, Zygmunt Gryczynski. Steady-state and time-resolved fluorescence studies of stripped Borage oil. Analytica chimica acta. 2009 Jul; 646(1-2):85-9. doi: 10.1016/j.aca.2009.05.007. [PMID: 19523559]
  • Bertille Carine Tchankou Leudeu, Clergé Tchiégang, Françoise Barbé, Benedicte Nicolas, Jean-Louis Guéant. Ricinodendron heutelotii (Bail.) or Tetracarpidium conophorum Müll. oils fed to male rats lower blood lipids. Nutrition research (New York, N.Y.). 2009 Jul; 29(7):503-9. doi: 10.1016/j.nutres.2009.07.004. [PMID: 19700038]
  • Raquel Hontecillas, Marianne O'Shea, Alexandra Einerhand, Margaret Diguardo, Josep Bassaganya-Riera. Activation of PPAR gamma and alpha by punicic acid ameliorates glucose tolerance and suppresses obesity-related inflammation. Journal of the American College of Nutrition. 2009 Apr; 28(2):184-95. doi: 10.1080/07315724.2009.10719770. [PMID: 19828904]
  • Gao-Feng Yuan, Jing-Qun Yuan, Duo Li. Punicic acid from Trichosanthes kirilowii seed oil is rapidly metabolized to conjugated linoleic acid in rats. Journal of medicinal food. 2009 Apr; 12(2):416-22. doi: 10.1089/jmf.2007.0541. [PMID: 19459746]
  • Masuko Kobori, Mayumi Ohnishi-Kameyama, Yukari Akimoto, Chizuko Yukizaki, Mitsuru Yoshida. Alpha-eleostearic acid and its dihydroxy derivative are major apoptosis-inducing components of bitter gourd. Journal of agricultural and food chemistry. 2008 Nov; 56(22):10515-20. doi: 10.1021/jf8020877. [PMID: 18959405]
  • Raquel Hontecillas, Maggie Diguardo, Elisa Duran, Marcel Orpi, Josep Bassaganya-Riera. Catalpic acid decreases abdominal fat deposition, improves glucose homeostasis and upregulates PPAR alpha expression in adipose tissue. Clinical nutrition (Edinburgh, Scotland). 2008 Oct; 27(5):764-72. doi: 10.1016/j.clnu.2008.07.007. [PMID: 18778878]
  • Mickaël Laguerre, Luis J López-Giraldo, Jérôme Lecomte, Bruno Baréa, Emmanuelle Cambon, Paul Fidèle Tchobo, Nathalie Barouh, Pierre Villeneuve. Conjugated autoxidizable triene (CAT) assay: a novel spectrophotometric method for determination of antioxidant capacity using triacylglycerol as ultraviolet probe. Analytical biochemistry. 2008 Sep; 380(2):282-90. doi: 10.1016/j.ab.2008.06.006. [PMID: 18585362]
  • Makio Morita, Masako Tokita. Hydroxy radical, hexanal, and decadienal generation by autocatalysts in autoxidation of linoleate alone and with eleostearate. Lipids. 2008 Jul; 43(7):589-97. doi: 10.1007/s11745-008-3170-9. [PMID: 18493810]
  • Meenakshi Shukla, Kalpana Gupta, Zafar Rasheed, Khursheed A Khan, Tariq M Haqqi. Bioavailable constituents/metabolites of pomegranate (Punica granatum L) preferentially inhibit COX2 activity ex vivo and IL-1beta-induced PGE2 production in human chondrocytes in vitro. Journal of inflammation (London, England). 2008 Jun; 5(?):9. doi: 10.1186/1476-9255-5-9. [PMID: 18554383]
  • Tsuyoshi Tsuzuki, Yuki Kawakami. Tumor angiogenesis suppression by alpha-eleostearic acid, a linolenic acid isomer with a conjugated triene system, via peroxisome proliferator-activated receptor gamma. Carcinogenesis. 2008 Apr; 29(4):797-806. doi: 10.1093/carcin/bgm298. [PMID: 18174233]
  • Ji-Yeon Park, Deog-Keun Kim, Zhong-Ming Wang, Pengmei Lu, Soon-Chul Park, Jin-Suk Lee. Production and characterization of biodiesel from tung oil. Applied biochemistry and biotechnology. 2008 Mar; 148(1-3):109-17. doi: 10.1007/s12010-007-8082-2. [PMID: 18418744]
  • Kazunori Koba, Jun Imamura, Asuka Akashoshi, Junko Kohno-Murase, Shoko Nishizono, Mari Iwabuchi, Kazunari Tanaka, Michihiro Sugano. Genetically modified rapeseed oil containing cis-9,trans-11,cis-13-octadecatrienoic acid affects body fat mass and lipid metabolism in mice. Journal of agricultural and food chemistry. 2007 May; 55(9):3741-8. doi: 10.1021/jf063264z. [PMID: 17394332]
  • Rikako Suzuki, Yumiko Yasui, Hiroyuki Kohno, Shingo Miyamoto, Masashi Hosokawa, Kazuo Miyashita, Takuji Tanaka. Catalpa seed oil rich in 9t,11t,13c-conjugated linolenic acid suppresses the development of colonic aberrant crypt foci induced by azoxymethane in rats. Oncology reports. 2006 Nov; 16(5):989-96. doi: 10.3892/or.16.5.989. [PMID: 17016582]
  • Jay M Shockey, Satinder K Gidda, Dorselyn C Chapital, Jui-Chang Kuan, Preetinder K Dhanoa, John M Bland, Steven J Rothstein, Robert T Mullen, John M Dyer. Tung tree DGAT1 and DGAT2 have nonredundant functions in triacylglycerol biosynthesis and are localized to different subdomains of the endoplasmic reticulum. The Plant cell. 2006 Sep; 18(9):2294-313. doi: 10.1105/tpc.106.043695. [PMID: 16920778]
  • J O Metzger, U Bornscheuer. Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Applied microbiology and biotechnology. 2006 Jun; 71(1):13-22. doi: 10.1007/s00253-006-0335-4. [PMID: 16604360]
  • Edgar B Cahoon, Charles R Dietrich, Knut Meyer, Howard G Damude, John M Dyer, Anthony J Kinney. Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds. Phytochemistry. 2006 Jun; 67(12):1166-76. doi: 10.1016/j.phytochem.2006.04.013. [PMID: 16762380]
  • Y Kitamura, M Yamagishi, K Okazaki, T Umemura, T Imazawa, A Nishikawa, W Matsumoto, M Hirose. Lack of chemopreventive effects of alpha-eleostearic acid on 7,12-dimethylbenz[a]anthracene (DMBA) and 1,2-dimethylhydrazine (DMH)-induced mammary and colon carcinogenesis in female Sprague-Dawley rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2006 Feb; 44(2):271-7. doi: 10.1016/j.fct.2004.11.021. [PMID: 16122863]
  • Masao Yamasaki, Takae Kitagawa, Nami Koyanagi, Hitomi Chujo, Hidenori Maeda, Junko Kohno-Murase, Jun Imamura, Hirofumi Tachibana, Koji Yamada. Dietary effect of pomegranate seed oil on immune function and lipid metabolism in mice. Nutrition (Burbank, Los Angeles County, Calif.). 2006 Jan; 22(1):54-9. doi: 10.1016/j.nut.2005.03.009. [PMID: 16226015]
  • Pubali Dhar, Krishna Chattopadhyay, Debasish Bhattacharyya, Anadi Roychoudhury, Arundhat Biswas, Santinath Ghosh. Antioxidative effect of conjugated linolenic acid in diabetic and non-diabetic blood: an in vitro study. Journal of oleo science. 2006; 56(1):19-24. doi: 10.5650/jos.56.19. [PMID: 17693694]
  • Yumiko Yasui, Masashi Hosokawa, Takehiko Sahara, Rikako Suzuki, Satoru Ohgiya, Hiroyuki Kohno, Takuji Tanaka, Kazuo Miyashita. Bitter gourd seed fatty acid rich in 9c,11t,13t-conjugated linolenic acid induces apoptosis and up-regulates the GADD45, p53 and PPARgamma in human colon cancer Caco-2 cells. Prostaglandins, leukotrienes, and essential fatty acids. 2005 Aug; 73(2):113-9. doi: 10.1016/j.plefa.2005.04.013. [PMID: 15961301]
  • Ephraim Philip Lansky, Gregory Harrison, Paul Froom, Wen G Jiang. Pomegranate (Punica granatum) pure chemicals show possible synergistic inhibition of human PC-3 prostate cancer cell invasion across Matrigel. Investigational new drugs. 2005 Mar; 23(2):121-2. doi: 10.1007/s10637-005-5856-7. [PMID: 15744587]
  • Keisuke Arao, Yu-Ming Wang, Nao Inoue, Junichi Hirata, Jae-Young Cha, Koji Nagao, Teruyoshi Yanagita. Dietary effect of pomegranate seed oil rich in 9cis, 11trans, 13cis conjugated linolenic acid on lipid metabolism in obese, hyperlipidemic OLETF rats. Lipids in health and disease. 2004 Nov; 3(?):24. doi: 10.1186/1476-511x-3-24. [PMID: 15533261]
  • Tsuyoshi Tsuzuki, Yoshiko Tokuyama, Miki Igarashi, Kiyotaka Nakagawa, Yusuke Ohsaki, Michio Komai, Teruo Miyazawa. Alpha-eleostearic acid (9Z11E13E-18:3) is quickly converted to conjugated linoleic acid (9Z11E-18:2) in rats. The Journal of nutrition. 2004 Oct; 134(10):2634-9. doi: 10.1093/jn/134.10.2634. [PMID: 15465759]
  • Tsuyoshi Tsuzuki, Yoshiko Tokuyama, Miki Igarashi, Teruo Miyazawa. Tumor growth suppression by alpha-eleostearic acid, a linolenic acid isomer with a conjugated triene system, via lipid peroxidation. Carcinogenesis. 2004 Aug; 25(8):1417-25. doi: 10.1093/carcin/bgh109. [PMID: 14963014]
  • Tsuyoshi Tsuzuki, Miki Igarashi, Toshio Iwata, Yoshie Yamauchi-Sato, Takaya Yamamoto, Kanehide Ogita, Toshihide Suzuki, Teruo Miyazawa. Oxidation rate of conjugated linoleic acid and conjugated linolenic acid is slowed by triacylglycerol esterification and alpha-tocopherol. Lipids. 2004 May; 39(5):475-80. doi: 10.1007/s11745-004-1253-z. [PMID: 15506243]
  • Miki Igarashi, Tsuyoshi Tsuzuki, Tomoko Kambe, Teruo Miyazawa. Recommended methods of fatty acid methylester preparation for conjugated dienes and trienes in food and biological samples. Journal of nutritional science and vitaminology. 2004 Apr; 50(2):121-8. doi: 10.3177/jnsv.50.121. [PMID: 15242016]
  • Tsuyoshi Tsuzuki, Miki Igarashi, Michio Komai, Teruo Miyazawa. The metabolic conversion of 9,11,13-eleostearic acid (18:3) to 9,11-conjugated linoleic acid (18:2) in the rat. Journal of nutritional science and vitaminology. 2003 Jun; 49(3):195-200. doi: 10.3177/jnsv.49.195. [PMID: 12953798]
  • Mari Iwabuchi, Junko Kohno-Murase, Jun Imamura. Delta 12-oleate desaturase-related enzymes associated with formation of conjugated trans-delta 11, cis-delta 13 double bonds. The Journal of biological chemistry. 2003 Feb; 278(7):4603-10. doi: 10.1074/jbc.m210748200. [PMID: 12464604]
  • John M Dyer, Dorselyn C Chapital, Jui-Chang W Kuan, Robert T Mullen, Charlotta Turner, Thomas A McKeon, Armand B Pepperman. Molecular analysis of a bifunctional fatty acid conjugase/desaturase from tung. Implications for the evolution of plant fatty acid diversity. Plant physiology. 2002 Dec; 130(4):2027-38. doi: 10.1104/pp.102.010835. [PMID: 12481086]
  • Ellen Hornung, Christian Pernstich, Ivo Feussner. Formation of conjugated Delta11Delta13-double bonds by Delta12-linoleic acid (1,4)-acyl-lipid-desaturase in pomegranate seeds. European journal of biochemistry. 2002 Oct; 269(19):4852-9. doi: 10.1046/j.1432-1033.2002.03184.x. [PMID: 12354116]
  • Jung-Suck Lee, Jun-ichi Takai, Kazuaki Takahasi, Yasushi Endo, Kenshiro Fujimoto, Seiji Koike, Wataru Matsumoto. Effect of dietary tung oil on the growth and lipid metabolism of laying hens. Journal of nutritional science and vitaminology. 2002 Apr; 48(2):142-8. doi: 10.3177/jnsv.48.142. [PMID: 12171435]
  • M Igarashi, T Miyazawa. Newly recognized cytotoxic effect of conjugated trienoic fatty acids on cultured human tumor cells. Cancer letters. 2000 Feb; 148(2):173-9. doi: 10.1016/s0304-3835(99)00332-8. [PMID: 10695994]
  • P Dhar, S Ghosh, D K Bhattacharyya. Dietary effects of conjugated octadecatrienoic fatty acid (9 cis, 11 trans, 13 trans) levels on blood lipids and nonenzymatic in vitro lipid peroxidation in rats. Lipids. 1999 Feb; 34(2):109-14. doi: 10.1007/s11745-999-0343-2. [PMID: 10102236]
  • P Dhar, D K Bhattacharyya. Nutritional characteristics of oil containing conjugated octadecatrienoic fatty acid. Annals of nutrition & metabolism. 1998; 42(5):290-6. doi: 10.1159/000012746. [PMID: 9812020]
  • M Takenaga, A Hirai, T Terano, Y Tamura, H Kitagawa, S Yoshida. In vitro effect of trichosanic acid, a major component of Trichosanthes japonica on platelet aggregation and arachidonic acid metabolism in human platelets. Prostaglandins, leukotrienes, and essential fatty acids. 1988 Feb; 31(2):65-72. doi: 10.1016/0952-3278(88)90078-6. [PMID: 3357911]
  • J F MEAD, D L FILLERUP, A B DECKER, L R BENNETT. The measurement of fat absorption and distribution using eleostearic acid. The Journal of nutrition. 1952 Apr; 46(4):499-513. doi: 10.1093/jn/46.4.499. [PMID: 14946591]