Petroselinic acid (BioDeep_00000000628)

 

Secondary id: BioDeep_00000415894, BioDeep_00000864600, BioDeep_00001867534

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 natural product


代谢物信息卡片


Petroselinic acid; Petroselic acid; 5-heptadecylene-1-carboxylic acid; delta-5-octadecylenic acid; cis-6-octadecenoic acid; C18:1n-12

化学式: C18H34O2 (282.2559)
中文名称: 芹子酸, 岩芹酸, 十八碳6烯酸, 十八碳 6 烯酸, 6Z-十八碳烯酸, 岩芹炔酸
谱图信息: 最多检出来源 Viridiplantae(plant) 21.11%

分子结构信息

SMILES: C(=C/CCCCCCCCCCC)/CCCCC(=O)O
InChI: InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h12-13H,2-11,14-17H2,1H3,(H,19,20)

描述信息

Petroselinic acid, also known as (6Z)-Octadecenoic acid, is an 18-carbon unsaturated fatty acid that occurs naturally in several animal and vegetable fats and oils. It is a white powder and is commercially available. In chemical terms, petroselinic acid is classified as a monounsaturated omega-12 fatty acid, abbreviated as 18:1 cis-6. Petroselinic acid is a positional isomer of oleic acid. The term "petroselinic" means related to, or derived from, oil of Petroselinum, or oil of parsley. Petroselinic acid was first isolated from parsley seed oil in 1909. Petroselinic acid occurs in high amounts in plants in the Apiaceae family (a family of mostly aromatic flowering plants named after the genus Apium and commonly known as the celery, carrot or parsley family), Araliaceae (a family of flowering plants composed of about 43 genera and around 1500 species consisting of primarily woody plants and some herbaceous plants), Griselinia (Griseliniaceae) and in Garryaceae. The occurrence of petroselinic acid as the major fatty acid is used in chemosystematics as a proof of a close relationship of several families within the Apiales as well as within the Garryales. Petroselonic acid has been found in coriander (Coriandrum sativum) and cumin (Cuminum cyminum) and caraway seeds. In addition, petroselinic acid has been found in minor amounts in several fats of plant and animal origin, including in human sources. Petroselinic acid is an important oleochemical material for the food, cosmetics, chemistry and pharmaceutical industry (PMID: 16604360) as it can be easily processed into lauric and adipinic acid.
Petroselinic acid is the cis-isomer of octadec-6-enoic acid, a long-chain fatty acid. It has a role as a plant metabolite. It is a conjugate acid of a petroselinate.
Petroselinic acid is a natural product found in Staphisagria macrosperma, Eleutherococcus sessiliflorus, and other organisms with data available.
Found in umbelliferous seed oils e.g. major constituent of oils of parsley, ivy, fennel, celery and others [DFC].
Petroselinic acid, a positional isomer of oleic acid, is isolated from the vegetable oil of Coriandrum sativum fruits.
Petroselinic acid, a positional isomer of oleic acid, is isolated from the vegetable oil of Coriandrum sativum fruits.

同义名列表

58 个代谢物同义名

Petroselinic acid; Petroselic acid; 5-heptadecylene-1-carboxylic acid; delta-5-octadecylenic acid; cis-6-octadecenoic acid; C18:1n-12; petroselinic acid, sodium salt, (Z)-isomer; Petroselinic acid, analytical standard; CIS-5-HEPTADECYLENE-1-CARBOXYLIC ACID; 0DA8F903-431D-46A3-A3AC-0E0BE12DC1EE; 5-heptadecylene-1-carboxylic acid; Petroselinic acid, >=99\\%, powder; cis-omega-12-octadecenoic acid; cis-Delta(6)-octadecenoic acid; CIS-.DELTA.6-OCTADECENOIC ACID; petroselinic acid, (Z)-isomer; petroselinic acid, (E)-isomer; (6Z)-6-Octadecenoic acid #; 6-Octadecenoic acid, (6Z)-; delta-5-octadecylenic acid; Octadecenoic acid, 6-(Z)-; 6-Octadecenoic acid, (Z)-; cis- -6-Octadecenoic acid; (6Z)-octadec-6-enoic acid; cis-octadec-6-enoic acid; (Z)-Octadec-6-enoic acid; (6Z)-6-Octadecenoic acid; (Z)-6-octadecenoic acid; cis-6-Octadecenoic acid; PETROSELINIC ACID [MI]; (6Z)-Octadecenoic acid; (6Z)-petroselinic acid; cis-petroselinic acid; (6Z)-Octadec-6-enoate; 6Z-octadecenoic acid; octadec-6-enoic acid; (6Z)-6-Octadecenoate; 6-octadecylenic acid; cis-6-Octadecenoate; (Z)-6-Octadecenoate; 6-octadecenoic acid; Petroseleninsaeure; (6Z)-Octadecenoate; Octadec-6c-ensaere; Octadec-6-ensaeure; petroselenic acid; Petroselinic acid; 6-Octadecensaeure; Petroselinsaeure; Octadec-6-enoate; UNII-3A10DOC461; Petroselic acid; Petroselinate; 3A10DOC461; 18:1(N-12); AI3-36446; C18:1n-12; C18:1n-6; 18:1N-6; FA 18:1; 4I1; Petroselinic acid; (6Z)-Octadecenoic acid



数据库引用编号

27 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)

141 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。

亚细胞结构定位 关联基因列表
Cytoplasm 5 ACP1, G6PD, MTOR, NRP1, RXRA
Peripheral membrane protein 2 G6PD, MTOR
Endoplasmic reticulum membrane 3 DGAT2, FADS3, MTOR
Mitochondrion membrane 1 NRP1
Nucleus 4 MTOR, PLCZ1, PPARA, RXRA
cytosol 8 ACP1, DGAT2, G6PD, LIPE, MTOR, NRP1, PLCZ1, RXRA
dendrite 1 MTOR
mitochondrial membrane 1 NRP1
phagocytic vesicle 1 MTOR
nucleoplasm 5 MTOR, PLCZ1, PPARA, RXRA, TMPRSS2
RNA polymerase II transcription regulator complex 1 RXRA
Cell membrane 4 LIPE, NRP1, TMPRSS2, TRPA1
Cytoplasmic side 1 MTOR
Multi-pass membrane protein 3 DGAT2, FADS3, TRPA1
Golgi apparatus membrane 1 MTOR
glutamatergic synapse 1 NRP1
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
sarcolemma 1 ACP1
Cytoplasm, cytosol 2 G6PD, LIPE
Lysosome 1 MTOR
plasma membrane 4 NRP1, P2RY10, TMPRSS2, TRPA1
Membrane 8 DGAT2, FADS3, G6PD, LIPE, MTOR, NRP1, TMPRSS2, TRPA1
axon 1 NRP1
caveola 1 LIPE
extracellular exosome 3 ACP1, G6PD, TMPRSS2
Lysosome membrane 1 MTOR
endoplasmic reticulum 1 DGAT2
extracellular space 4 IL6, NRP1, PNLIP, PRSS2
perinuclear region of cytoplasm 3 DGAT2, NRP1, PLCZ1
mitochondrion 2 DGAT2, RXRA
intracellular membrane-bounded organelle 2 DGAT2, G6PD
Microsome membrane 1 MTOR
pronucleus 1 PLCZ1
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 NRP1
Secreted 3 IL6, NRP1, PNLIP
extracellular region 4 IL6, PNLIP, PRSS2, TMPRSS2
cytoplasmic side of plasma membrane 2 ACP1, G6PD
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 1 MTOR
[Isoform 2]: Secreted 1 NRP1
transcription regulator complex 1 RXRA
centriolar satellite 1 G6PD
cytoplasmic vesicle 1 NRP1
nucleolus 1 PLCZ1
Early endosome 1 NRP1
Single-pass type II membrane protein 1 TMPRSS2
postsynaptic membrane 1 NRP1
Cytoplasm, perinuclear region 2 DGAT2, PLCZ1
focal adhesion 1 NRP1
perinuclear endoplasmic reticulum membrane 1 DGAT2
extracellular matrix 1 PRSS2
Nucleus, PML body 1 MTOR
PML body 1 MTOR
receptor complex 2 NRP1, RXRA
neuron projection 1 NRP1
chromatin 2 PPARA, RXRA
stereocilium bundle 1 TRPA1
nuclear envelope 2 MTOR, NRP1
Nucleus envelope 1 NRP1
Endomembrane system 1 MTOR
sorting endosome 1 NRP1
Lipid droplet 2 DGAT2, LIPE
Membrane, caveola 1 LIPE
endoplasmic reticulum lumen 1 IL6
azurophil granule lumen 1 PRSS2
neurofilament 1 NRP1
semaphorin receptor complex 1 NRP1
[Transmembrane protease serine 2 catalytic chain]: Secreted 1 TMPRSS2
Cytoplasmic vesicle, phagosome 1 MTOR
sperm head 1 PLCZ1
interleukin-6 receptor complex 1 IL6


文献列表

  • Ahmed Hajib, Said El Harkaoui, Hasnae Choukri, Aya Khouchlaa, Sarra Aourabi, Naoual El Menyiy, Abdelhakim Bouyahya, Bertrand Matthaeus. Apiaceae Family an Important Source of Petroselinic Fatty Acid: Abundance, Biosynthesis, Chemistry, and Biological Proprieties. Biomolecules. 2023 11; 13(11):. doi: 10.3390/biom13111675. [PMID: 38002357]
  • Zheng Yang, Changsheng Li, Qingli Jia, Cuizhu Zhao, David C Taylor, Dawei Li, Meng Zhang. Transcriptome Analysis Reveals Candidate Genes for Petroselinic Acid Biosynthesis in Fruits of Coriandrum sativum L. Journal of agricultural and food chemistry. 2020 May; 68(19):5507-5520. doi: 10.1021/acs.jafc.0c01487. [PMID: 32320606]
  • Juergen K R Wanner, Do N Dai, Le T Huong, Nguyen V Hung, Erich Schmidt, Leopold Jirovetz. Fatty Acid Methyl Ester Composition of Some Turkish Apiaceae Seed Oils: New Sources for Petroselinic Acid. Natural product communications. 2016 Nov; 11(11):1697-1700. doi: ". [PMID: 30475510]
  • Evelien Uitterhaegen, Klicia A Sampaio, Elisabeth I P Delbeke, Wim De Greyt, Muriel Cerny, Philippe Evon, Othmane Merah, Thierry Talou, Christian V Stevens. Characterization of French Coriander Oil as Source of Petroselinic Acid. Molecules (Basel, Switzerland). 2016 Sep; 21(9):. doi: 10.3390/molecules21091202. [PMID: 27617992]
  • Najla Gooda Sahib, Farooq Anwar, Anwarul-Hassan Gilani, Azizah Abdul Hamid, Nazamid Saari, Khalid M Alkharfy. Coriander (Coriandrum sativum L.): a potential source of high-value components for functional foods and nutraceuticals--a review. Phytotherapy research : PTR. 2013 Oct; 27(10):1439-56. doi: 10.1002/ptr.4897. [PMID: 23281145]
  • Wei-Luen Yu, William Ansari, Nathan G Schoepp, Michael J Hannon, Stephen P Mayfield, Michael D Burkart. Modifications of the metabolic pathways of lipid and triacylglycerol production in microalgae. Microbial cell factories. 2011 Nov; 10(?):91. doi: 10.1186/1475-2859-10-91. [PMID: 22047615]
  • Antonio Ruiz-Vela, Cristóbal Aguilar-Gallardo, Ana M Martínez-Arroyo, Mario Soriano-Navarro, Verónica Ruiz, Carlos Simón. Specific unsaturated fatty acids enforce the transdifferentiation of human cancer cells toward adipocyte-like cells. Stem cell reviews and reports. 2011 Nov; 7(4):898-909. doi: 10.1007/s12015-011-9253-7. [PMID: 21499706]
  • Iness Bettaieb, Soumaya Bourgou, Jezia Sriti, Kamel Msaada, Ferid Limam, Brahim Marzouk. Essential oils and fatty acids composition of Tunisian and Indian cumin (Cuminum cyminum L.) seeds: a comparative study. Journal of the science of food and agriculture. 2011 Aug; 91(11):2100-7. doi: 10.1002/jsfa.4513. [PMID: 21681765]
  • Roumen V Denev, Ivalina S Kuzmanova, Svetlana M Momchilova, Boryana M Nikolova-Damyanova. Resolution and quantification of isomeric fatty acids by silver ion HPLC: fatty acid composition of aniseed oil (Pimpinella anisum, Apiaceae). Journal of AOAC International. 2011 Jan; 94(1):4-8. doi: . [PMID: 21391475]
  • Robert H Glew, Lu-Te Chuang, Tammy Berry, Henry Okolie, Michael J Crossey, Dorothy J VanderJagt. Lipid profiles and trans fatty acids in serum phospholipids of semi-nomadic Fulani in northern Nigeria. Journal of health, population, and nutrition. 2010 Apr; 28(2):159-66. doi: 10.3329/jhpn.v28i2.4886. [PMID: 20411679]
  • Bochra Laribi, Karima Kouki, Abdelaziz Mougou, Brahim Marzouk. Fatty acid and essential oil composition of three Tunisian caraway (Carum carvi L.) seed ecotypes. Journal of the science of food and agriculture. 2010 Feb; 90(3):391-6. doi: 10.1002/jsfa.3827. [PMID: 20355058]
  • Xiuying Li, Yanhong Zhu, Tong Wu, Shuzhen Zhang, Peter Christie. Using a novel petroselinic Acid embedded cellulose acetate membrane to mimic plant partitioning and in vivo uptake of polycyclic aromatic hydrocarbons. Environmental science & technology. 2010 Jan; 44(1):297-301. doi: 10.1021/es902283x. [PMID: 19950922]
  • Ilkka J Miinalainen, Werner Schmitz, Anne Huotari, Kaija J Autio, Raija Soininen, Emiel Ver Loren van Themaat, Myriam Baes, Karl-Heinz Herzig, Ernst Conzelmann, J Kalervo Hiltunen. Mitochondrial 2,4-dienoyl-CoA reductase deficiency in mice results in severe hypoglycemia with stress intolerance and unimpaired ketogenesis. PLoS genetics. 2009 Jul; 5(7):e1000543. doi: 10.1371/journal.pgen.1000543. [PMID: 19578400]
  • 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]
  • Mi Jung Kim, Jeong Sheop Shin, Jeong-Kook Kim, Mi Chung Suh. Genomic structures and characterization of the 5'-flanking regions of acyl carrier protein and Delta4-palmitoyl-ACP desaturase genes from Coriandrum sativum. Biochimica et biophysica acta. 2005 Sep; 1730(3):235-44. doi: 10.1016/j.bbaexp.2005.06.011. [PMID: 16112758]
  • N Tsevegsuren, K Aitzetmuller, K Vosmann. Geranium sanguineum (Geraniaceae) seed oil: a new source of petroselinic and vernolic acid. Lipids. 2004 Jun; 39(6):571-6. doi: 10.1007/s11745-004-1265-8. [PMID: 15554157]
  • Sébastien Guiet, Richard J Robins, Michele Lees, Isabelle Billault. Quantitative 2H NMR analysis of deuterium distribution in petroselinic acid isolated from parsley seed. Phytochemistry. 2003 Sep; 64(1):227-33. doi: 10.1016/s0031-9422(03)00278-4. [PMID: 12946421]
  • Mi Chung Suh, David J Schultz, John B Ohlrogge. What limits production of unusual monoenoic fatty acids in transgenic plants?. Planta. 2002 Aug; 215(4):584-95. doi: 10.1007/s00425-002-0751-3. [PMID: 12172841]
  • Frédéric Destaillats, Paul Angers. Base-catalyzed derivatization methodology for FA analysis. application to milk fat and celery seed lipid TAG. Lipids. 2002 May; 37(5):527-32. doi: 10.1007/s11745-002-0928-9. [PMID: 12056597]
  • Frederic Destaillats, Joseph Arul, James E Simon, Robert L Wolff, Paul Angers. Dibutyrate derivatization of monoacylglycerols for the resolution of regioisomers of oleic, petroselinic, and cis-vaccenic acids. Lipids. 2002 Jan; 37(1):111-6. doi: 10.1007/s11745-002-0870-x. [PMID: 11876258]
  • S Mekhedov, E B Cahoon, J Ohlrogge. An unusual seed-specific 3-ketoacyl-ACP synthase associated with the biosynthesis of petroselinic acid in coriander. Plant molecular biology. 2001 Nov; 47(4):507-18. doi: 10.1023/a:1011832611885. [PMID: 11669576]
  • P Avato, F P Fanizzi, I Rosito. The genus Thapsia as a source of petroselinic acid. Lipids. 2001 Aug; 36(8):845-50. doi: 10.1007/s11745-001-0794-5. [PMID: 11592737]
  • N Weber, S Schönwiese, E Klein, K D Mukherjee. Adipose tissue triacylglycerols of rats are modulated differently by dietary isomeric octadecenoic acids from coriander oil and high oleic sunflower oil. The Journal of nutrition. 1999 Dec; 129(12):2206-11. doi: 10.1093/jn/129.12.2006. [PMID: 10573551]
  • Y Takeuchi, Y Yamaoka, S Fukushima, K Miyawaki, K Taguchi, H Yasukawa, S Kishimoto, M Suzuki. Skin penetration enhancing action of cis-unsaturated fatty acids with omega-9, and omega-12-chain lengths. Biological & pharmaceutical bulletin. 1998 May; 21(5):484-91. doi: 10.1248/bpb.21.484. [PMID: 9635505]
  • K D Richter, K D Mukherjee, N Weber. Fat infiltration in liver of rats induced by different dietary plant oils: high oleic-, medium oleic- and high petroselinic acid-oils. Zeitschrift fur Ernahrungswissenschaft. 1996 Sep; 35(3):241-8. doi: 10.1007/bf01625687. [PMID: 8896286]
  • N Weber, K D Richter, E Schulte, K D Mukherjee. Petroselinic acid from dietary triacylglycerols reduces the concentration of arachidonic acid in tissue lipids of rats. The Journal of nutrition. 1995 Jun; 125(6):1563-8. doi: 10.1093/jn/125.6.1563. [PMID: 7782911]
  • S L Marcus, K S Miyata, R A Rachubinski, J P Capone. Transactivation by PPAR/RXR heterodimers in yeast is potentiated by exogenous fatty acid via a pathway requiring intact peroxisomes. Gene expression. 1995; 4(4-5):227-39. doi: . [PMID: 7787415]
  • E B Cahoon, P Dörmann, J B Ohlrogge. Petroselinic acid biosynthesis and production in transgenic plants. Progress in lipid research. 1994; 33(1-2):155-63. doi: 10.1016/0163-7827(94)90018-3. [PMID: 8190735]
  • E B Cahoon, J Shanklin, J B Ohlrogge. Expression of a coriander desaturase results in petroselinic acid production in transgenic tobacco. Proceedings of the National Academy of Sciences of the United States of America. 1992 Dec; 89(23):11184-8. doi: 10.1073/pnas.89.23.11184. [PMID: 1454797]