C18:3n-6,9,13 (BioDeep_00000607138)
代谢物信息卡片
(5Z,9Z,12E)-octadeca-5,9,12-trienoic acid
化学式: C18H30O2 (278.224568)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCC=CCC=CCCC=CCCCC(=O)O
InChI: InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,13-14H,2-5,8,11-12,15-17H2,1H3,(H,19,20)/b7-6+,10-9+,14-13+
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:180181
- ChEBI: CHEBI:180172
- PubChem: 5312494
- PubChem: 5312493
- Metlin: METLIN74014
- Metlin: METLIN74013
- CAS: 13237-97-3
- CAS: 2441-53-4
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)
0 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
- Xiaodan Wu, Sansan Bao, Linan Sun, Maoyu Zhang, Liang Yu, Ying Wang, Yujie Fu. A new integrated strategy for high purity pinolenic acid production from Pinus koraiensis Sieb. et Zucc seed oil and evaluation of its hypolipidemic activity in vivo.
Fitoterapia.
2024 Jun; 175(?):105842. doi:
10.1016/j.fitote.2024.105842. [PMID: 38296168] - Rabaa Takala, Dipak P Ramji, Ernest Choy. The Beneficial Effects of Pine Nuts and Its Major Fatty Acid, Pinolenic Acid, on Inflammation and Metabolic Perturbations in Inflammatory Disorders.
International journal of molecular sciences.
2023 Jan; 24(2):. doi:
10.3390/ijms24021171. [PMID: 36674687] - Rabaa Takala, Dipak P Ramji, Robert Andrews, You Zhou, Mustafa Farhat, Mohammed Elmajee, Shelley Rundle, Ernest Choy. Pinolenic acid exhibits anti-inflammatory and anti-atherogenic effects in peripheral blood-derived monocytes from patients with rheumatoid arthritis.
Scientific reports.
2022 05; 12(1):8807. doi:
10.1038/s41598-022-12763-8. [PMID: 35614190] - Seong Chul Jin, Mi Hye Kim, La Yoon Choi, Yeon Kyung Nam, Woong Mo Yang. Fat regulatory mechanisms of pine nut oil based on protein interaction network analysis.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2021 Jun; 86(?):153557. doi:
10.1016/j.phymed.2021.153557. [PMID: 33852976] - Ella J Baker, Elizabeth A Miles, Philip C Calder. A review of the functional effects of pine nut oil, pinolenic acid and its derivative eicosatrienoic acid and their potential health benefits.
Progress in lipid research.
2021 04; 82(?):101097. doi:
10.1016/j.plipres.2021.101097. [PMID: 33831456] - Karina V Sørensen, Svend S Korfitzen, Mads H Kaspersen, Elisabeth Rexen Ulven, Jeppe H Ekberg, Annette Bauer-Brandl, Trond Ulven, Kurt Højlund. Acute effects of delayed-release hydrolyzed pine nut oil on glucose tolerance, incretins, ghrelin and appetite in healthy humans.
Clinical nutrition (Edinburgh, Scotland).
2021 04; 40(4):2169-2179. doi:
10.1016/j.clnu.2020.09.043. [PMID: 33059911] - Ella J Baker, Carina A Valenzuela, Wies T M van Dooremalen, Leyre Martínez-Fernández, Parveen Yaqoob, Elizabeth A Miles, Philip C Calder. Gamma-Linolenic and Pinolenic Acids Exert Anti-Inflammatory Effects in Cultured Human Endothelial Cells Through Their Elongation Products.
Molecular nutrition & food research.
2020 10; 64(20):e2000382. doi:
10.1002/mnfr.202000382. [PMID: 32898315] - Jing Zhang, Sun-Dong Zhang, Peng Wang, Na Guo, Wei Wang, Li-Ping Yao, Qing Yang, Thomas Efferth, Jiao Jiao, Yu-Jie Fu. Pinolenic acid ameliorates oleic acid-induced lipogenesis and oxidative stress via AMPK/SIRT1 signaling pathway in HepG2 cells.
European journal of pharmacology.
2019 Oct; 861(?):172618. doi:
10.1016/j.ejphar.2019.172618. [PMID: 31430456] - Yasuyo Yamaoka, Seungjun Shin, Bae Young Choi, Hanul Kim, Sunghoon Jang, Masataka Kajikawa, Takashi Yamano, Fantao Kong, Bertrand Légeret, Hideya Fukuzawa, Yonghua Li-Beisson, Youngsook Lee. The bZIP1 Transcription Factor Regulates Lipid Remodeling and Contributes to ER Stress Management in Chlamydomonas reinhardtii.
The Plant cell.
2019 05; 31(5):1127-1140. doi:
10.1105/tpc.18.00723. [PMID: 30894460] - Jiwon Kim, Min-Yu Chung, Hee-Don Choi, In-Wook Choi, Byung Hee Kim. Enzymatic Synthesis of Structured Monogalactosyldiacylglycerols Enriched in Pinolenic Acid.
Journal of agricultural and food chemistry.
2018 Aug; 66(30):8079-8085. doi:
10.1021/acs.jafc.8b02599. [PMID: 29998729] - Min-Yu Chung, In-Hwan Kim, Byung Hee Kim. Preparation of Pinolenic Acid Concentrates from Pine Nut Oil Fatty Acids by Solvent Fractionation.
Journal of oleo science.
2018; 67(11):1373-1379. doi:
10.5650/jos.ess18100. [PMID: 30404957] - Heejin Kim, Nakyung Choi, Hak-Ryul Kim, Junsoo Lee, In-Hwan Kim. Preparation of High Purity Δ5-Olefinic Acids from Pine Nut Oil via Repeated Lipase-Catalyzed Esterification.
Journal of oleo science.
2018; 67(11):1435-1442. doi:
10.5650/jos.ess18136. [PMID: 30404964] - Min-Yu Chung, Hyunjoon Woo, Juyeon Kim, Daecheol Kong, Hee-Don Choi, In-Wook Choi, In-Hwan Kim, Sang K Noh, Byung Hee Kim. Pinolenic Acid in Structured Triacylglycerols Exhibits Superior Intestinal Lymphatic Absorption As Compared to Pinolenic Acid in Natural Pine Nut Oil.
Journal of agricultural and food chemistry.
2017 Mar; 65(8):1543-1549. doi:
10.1021/acs.jafc.6b05216. [PMID: 28198188] - Ah Ron Lee, Sung Nim Han. Pinolenic Acid Downregulates Lipid Anabolic Pathway in HepG2 Cells.
Lipids.
2016 07; 51(7):847-55. doi:
10.1007/s11745-016-4149-6. [PMID: 27084371] - Da Som No, Ting Ting Zhao, Yangha Kim, Mi-Ra Yoon, Jeom-Sig Lee, In-Hwan Kim. Preparation of highly purified pinolenic acid from pine nut oil using a combination of enzymatic esterification and urea complexation.
Food chemistry.
2015 Mar; 170(?):386-93. doi:
10.1016/j.foodchem.2014.08.074. [PMID: 25306361] - Da Som No, Tingting Zhao, Junsoo Lee, Jeom-Sig Lee, In-Hwan Kim. Synthesis of phytosteryl ester containing pinolenic acid in a solvent-free system using immobilized Candida rugosa lipase.
Journal of agricultural and food chemistry.
2013 Sep; 61(37):8934-40. doi:
10.1021/jf402953n. [PMID: 23988007] - Ngoc Hoan Le, Sunhye Shin, Thai Hien Tu, Chu-Sook Kim, Ji-Hye Kang, Goto Tsuyoshi, Kawada Teruo, Sung Nim Han, Rina Yu. Diet enriched with korean pine nut oil improves mitochondrial oxidative metabolism in skeletal muscle and brown adipose tissue in diet-induced obesity.
Journal of agricultural and food chemistry.
2012 Dec; 60(48):11935-41. doi:
10.1021/jf303548k. [PMID: 23140571] - Young-Gil Pyo, Seung In Hong, Yangha Kim, Byung Hee Kim, In-Hwan Kim. Synthesis of monoacylglycerol containing pinolenic acid via stepwise esterification using a cold active lipase.
Biotechnology progress.
2012 Sep; 28(5):1218-24. doi:
10.1002/btpr.1596. [PMID: 22753389] - Jong-Hun Choi, Byung Hee Kim, Seung In Hong, Chong-Tai Kim, Chul-Jin Kim, Yangha Kim, In-Hwan Kim. Lipase-catalysed production of triacylglycerols enriched in pinolenic acid at the sn-2 position from pine nut oil.
Journal of the science of food and agriculture.
2012 Mar; 92(4):870-6. doi:
10.1002/jsfa.4662. [PMID: 21953622] - Paula Cuadra-Crespo, Francisco M del Amor. Effects of postharvest treatments on fruit quality of sweet pepper at low temperature.
Journal of the science of food and agriculture.
2010 Dec; 90(15):2716-22. doi:
10.1002/jsfa.4147. [PMID: 20812372] - Xue-Mei Zhu, Jiang-Ning Hu, Jung-Ah Shin, Dan Li, Juan Jin, Prakash Adhikari, Casimir C Akoh, Jeung-Hee Lee, Sang-Won Choi, Ki-Teak Lee. Enrichment of pinolenic acid at the sn-2 position of triacylglycerol molecules through lipase-catalyzed reaction.
International journal of food sciences and nutrition.
2010 Mar; 61(2):138-48. doi:
10.3109/09637480903348106. [PMID: 20001760] - Masataka Kajikawa, Katsuyuki T Yamato, Yoshito Kohzu, Shin-ichiro Shoji, Keisuke Matsui, Yoshikazu Tanaka, Yasuyoshi Sakai, Hideya Fukuzawa. A front-end desaturase from Chlamydomonas reinhardtii produces pinolenic and coniferonic acids by omega13 desaturation in methylotrophic yeast and tobacco.
Plant & cell physiology.
2006 Jan; 47(1):64-73. doi:
10.1093/pcp/pci224. [PMID: 16267098] - Jin-Won Lee, Kwang-Won Lee, Seog-Won Lee, In-Hwan Kim, Chul Rhee. Selective increase in pinolenic acid (all-cis-5,9,12-18:3) in Korean pine nut oil by crystallization and its effect on LDL-receptor activity.
Lipids.
2004 Apr; 39(4):383-7. doi:
10.1007/s11745-004-1242-2. [PMID: 15357026] - A J Longman, L V Michaelson, O Sayanova, J A Napier, A K Stobart. An unusual desaturase in Aquilegia vulgaris.
Biochemical Society transactions.
2000 Dec; 28(6):641-3. doi:
10.1042/bst0280641. [PMID: 11171154] - M Sugano, I Ikeda, K Wakamatsu, T Oka. Influence of Korean pine (Pinus koraiensis)-seed oil containing cis-5,cis-9,cis-12-octadecatrienoic acid on polyunsaturated fatty acid metabolism, eicosanoid production and blood pressure of rats.
The British journal of nutrition.
1994 Nov; 72(5):775-83. doi:
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Journal of ocular pharmacology.
1993; 9(4):365-72. doi:
10.1089/jop.1993.9.365. [PMID: 8106842] - N L Verbey, N J van Haeringen, P T de Jong. Modulation of immunogenic keratitis in rabbits by topical administration of poly-unsaturated fatty acids.
Current eye research.
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Archivos latinoamericanos de nutricion.
1986 Sep; 36(3):401-14. doi:
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Prostaglandins, leukotrienes, and medicine.
1986 Aug; 23(2-3):123-7. doi:
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The Journal of nutrition.
1986 Feb; 116(2):198-203. doi:
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Journal of lipid research.
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