Pulegone (BioDeep_00000017531)

 

Secondary id: BioDeep_00000000844

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (theta)-

化学式: C10H16O (152.1201)
中文名称: 长叶薄荷酮, (+)-长叶薄荷酮, 胡薄荷酮, p-Menth-4（8）-en-3-one, 5-甲基-2-(1-甲基亚乙基)环己酮
谱图信息: 最多检出来源 Homo sapiens(plant) 19.36%

分子结构信息

SMILES: C1(=C(/C)\C)\CC[C@@H](C)CC\1=O
InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3

描述信息

Pulegone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. It is formally classified as a cyclic ketone although it is biochemically a monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Pulegone is a hydrophobic, neutral compound that is insoluble in water. It exists as a clear, colorless oil. There are two isomers of Pulegone (the R and the S isomer), with the R isomer being more common. It is used industrially as a food additive and a perfuming agent. Pulegone has a fresh, minty or peppermint odor and a minty, fruity or green taste. It is found naturally in the essential oils of a variety of plants such as Nepeta cataria (catnip), Hedeoma pulegioides (pennyroyal), and Mentha species. It is also found in a number of plant foods and spices such as blackberryies, black currants, bell peppers, cornmint, rosemary, black tea, thyme, orange mint, peppermint, and spearmint, which makes it a potential biomarker for the consumption of these food products. Pulegone is also one of more than 140 terpenes that are found in cannabis plants (PMID:6991645 ).
Pulegone, also known as (+)-(R)-pulegone or (1r)-(+)-P-menth-4(8)-en-3-one, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, pulegone is considered to be an isoprenoid lipid molecule. Pulegone is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Pulegone can be found in a number of food items such as globe artichoke, sacred lotus, garden onion, and rubus (blackberry, raspberry), which makes pulegone a potential biomarker for the consumption of these food products. Pulegone can be found primarily in saliva. Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal. It is classified as a monoterpene .
(+)-pulegone is the (5R)-enantiomer of p-menth-4(8)-en-3-one.
Pulegone is a natural product found in Hedeoma multiflora, Clinopodium dalmaticum, and other organisms with data available.
See also: Agathosma betulina leaf (part of).
The (5R)-enantiomer of p-menth-4(8)-en-3-one.
Pulegone, the major chemical constituent of Nepeta catariaessential oil which is an aromatic herb, is one of avian repellents[1]. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations[2].
Pulegone, the major chemical constituent of Nepeta catariaessential oil which is an aromatic herb, is one of avian repellents[1]. The molecular target for the repellent action of Pulegone in avian species is nociceptive TRP ankyrin 1 (TRPA1). Pulegone stimulates both TRPM8 and TRPA1 channel in chicken sensory neurons and suppresses the former but not the latter at high concentrations[2].

同义名列表

66 个代谢物同义名

Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (theta)-; (+)-Pulegone, primary pharmaceutical reference standard; Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (5R)-; Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (R)-; 5-Methyl-2-(1-methylethylidene)cyclohexanone, (R)-; (5R)-5-methyl-2-(propan-2-ylidene)cyclohexan-1-one; (5R)-5-Methyl-2-(1-methylethylidene)cyclohexanone; (R)-5-Methyl-2-(1-methylethylidene)cyclohexanone; (5R)-5-methyl-2-propan-2-ylidenecyclohexan-1-one; (R)-5-methyl-2-(propan-2-ylidene)cyclohexanone; (+)-1-Methyl-4-isopropylidene-3-cyclohexanone; (5R)-2-isopropylidene-5-methyl-cyclohexanone; 5-Methyl-2-(1-methylethylidene)cyclohexanone; (5R)-2-isopropylidene-5-methylcyclohexanone; doi:10.14272/NZGWDASTMWDZIW-MRVPVSSYSA-N.1; (R)-2-Isopropylidene-5-methylcyclohexanone; 1-Isopropylidene-4-methyl-2-cyclohexanone; 1-Methyl-4-isopropylidene-3-cyclohexanone; (R)-(+)-Pulegone, 85\\%, technical grade; 10.14272/NZGWDASTMWDZIW-MRVPVSSYSA-N.1; 3-Methyl-6-isopropylidenecyclohexanone; (+)-Pulegone, analytical standard; p-MENTH-4(8)-EN-3-ONE, (R)-(+)-; 4(8)-p-Menthen-3-one, (R)-(+)-; (1R)-(+)-p-Menth-4(8)-en-3-one; (R)-(+)-P-MENTH-4(8)-EN-3-ONE; 4(8)-p-Menthen-3-one, delta-; (+)-4(8)-Para-menthen-3-one; 1beta-p-menth-4(8)-en-3-one; (R)-p-Menth-4(8)-en-3-one; (R)-(+)-Pulegone, >=90\\%; (R)-(+)-Pulegone, 97\\%; p-Menth-4(8)-en-3-one; pulegone, (R)-isomer; pulegone, (S)-isomer; (R)-Pulegone - 90\\%; Pulegone (natural); (+)-(R)-Pulegone; (R)-(+)-Pulegone; PULEGONE (IARC); cis-isopulegone; PULEGONE [IARC]; PULEGONE [FHFI]; UNII-4LF2673R3G; R-(+)-Pulegone; PULEGONE, (D); PULEGONE [MI]; (1R)-PULEGONE; (R)-Pulegone; (+)-Pulegone; Pulegone, d-; Pulegone,(S); Tox21_200206; CAS-89-82-7; isopulegone; d-Pulegone; L-Pulegone; 4LF2673R3G; FEMA 2963; AI3-11218; NSC 15334; Pulegone; Pulegon; Pulegone; Pulegone; p-Menth-4(8)-en-3-one



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(1)

PlantCyc(1)

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)

85 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 8 BCL2, CASP1, CYP1A1, CYP2E1, CYP3A4, HPGDS, IL18, NLRP3
Peripheral membrane protein 4 ACHE, CYP1A1, CYP1B1, CYP2E1
Endoplasmic reticulum membrane 7 BCL2, CYP1A1, CYP1A2, CYP1B1, CYP2E1, CYP3A4, TRPM8
Nucleus 3 ACHE, BCL2, NLRP3
cytosol 7 ANK1, BCL2, CASP1, GPT, HPGDS, IL18, NLRP3
nucleoplasm 1 HPGDS
Cell membrane 5 ACHE, CASP1, TNF, TRPA1, TRPM8
Multi-pass membrane protein 2 TRPA1, TRPM8
Golgi apparatus membrane 1 NLRP3
Synapse 1 ACHE
cell surface 2 ACHE, TNF
Golgi apparatus 1 ACHE
Golgi membrane 1 NLRP3
mitochondrial inner membrane 2 CYP1A1, CYP2E1
neuromuscular junction 1 ACHE
neuronal cell body 1 TNF
sarcolemma 1 ANK1
Cytoplasm, cytosol 2 IL18, NLRP3
plasma membrane 8 ACHE, ANK1, BCHE, CASP1, IFNLR1, TNF, TRPA1, TRPM8
Membrane 9 ACHE, ANK1, BCL2, CYP1B1, CYP3A4, IFNLR1, NLRP3, TRPA1, TRPM8
basolateral plasma membrane 1 ANK1
extracellular exosome 1 GPT
endoplasmic reticulum 2 BCL2, NLRP3
extracellular space 6 ACHE, BCHE, IL18, IL4, IL5, TNF
perinuclear region of cytoplasm 1 ACHE
mitochondrion 4 BCL2, CYP1A1, CYP1B1, NLRP3
protein-containing complex 2 BCL2, CASP1
intracellular membrane-bounded organelle 6 CYP1A1, CYP1A2, CYP1B1, CYP2E1, CYP3A4, HPGDS
Microsome membrane 5 CYP1A1, CYP1A2, CYP1B1, CYP2E1, CYP3A4
Single-pass type I membrane protein 1 IFNLR1
Secreted 6 ACHE, BCHE, IL18, IL4, IL5, NLRP3
extracellular region 7 ACHE, BCHE, IL18, IL4, IL5, NLRP3, TNF
cytoplasmic side of plasma membrane 1 ANK1
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Extracellular side 1 ACHE
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 TNF, TRPM8
Z disc 1 ANK1
nucleolus 1 CASP1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 ANK1
Mitochondrion inner membrane 2 CYP1A1, CYP2E1
Membrane raft 2 TNF, TRPM8
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 ANK1
microtubule 1 CASP1
axolemma 1 ANK1
basement membrane 1 ACHE
sarcoplasmic reticulum 1 ANK1
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 2 CASP1, NLRP3
neuron projection 1 ANK1
stereocilium bundle 1 TRPA1
phagocytic cup 1 TNF
cytoskeleton 1 ANK1
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
Endomembrane system 1 NLRP3
M band 1 ANK1
microtubule organizing center 1 NLRP3
side of membrane 1 ACHE
myelin sheath 1 BCL2
plasma membrane raft 1 TRPM8
endoplasmic reticulum lumen 1 BCHE
nuclear envelope lumen 1 BCHE
AIM2 inflammasome complex 1 CASP1
synaptic cleft 1 ACHE
canonical inflammasome complex 1 CASP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
spectrin-associated cytoskeleton 1 ANK1
ankyrin-1 complex 1 ANK1
BAD-BCL-2 complex 1 BCL2
[Isoform Mu18]: Sarcoplasmic reticulum 1 ANK1
[Isoform Mu19]: Sarcoplasmic reticulum 1 ANK1
[Isoform Mu20]: Sarcoplasmic reticulum 1 ANK1
[Isoform H]: Cell membrane 1 ACHE
IPAF inflammasome complex 1 CASP1
NLRP1 inflammasome complex 1 CASP1
protease inhibitor complex 1 CASP1
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Aleksandra Maria Izdebska, Małgorzata Kłyś, Magdalena Nowak-Chmura, Sylwia Koczanowicz. Lower dose of plant substance more effective in repelling Rhyzopertha dominica F . (Coleoptera, Bostrichidae) and Sitophilus granarius L. (Coleoptera, Dryophthoridae). Annals of agricultural and environmental medicine : AAEM. 2023 Sep; 30(3):407-412. doi: 10.26444/aaem/163326. [PMID: 37772516]
  • Fatemeh Shahdadi, Maliheh Faryabi, Haroon Khan, Ali Salehi Sardoei, Bahman Fazeli-Nasab, Bey Hing Goh, Khang Wen Goh, Ching Siang Tan. Mentha longifolia Essential Oil and Pulegone in Edible Coatings of Alginate and Chitosan: Effects on Pathogenic Bacteria in Lactic Cheese. Molecules (Basel, Switzerland). 2023 Jun; 28(11):. doi: 10.3390/molecules28114554. [PMID: 37299028]
  • Tyler M Wilson, Audra Davis, Reilly E Sonstrom, Justin L Neill, Emma A Ziebarth, Ariel Poulson, Richard E Carlson. Essential Oil Composition and Enantioselective Profile of Agastache urticifolia (Lamiaceae) and Monardella odoratissima (Lamiaceae) from Utah. Molecules (Basel, Switzerland). 2023 Feb; 28(5):. doi: 10.3390/molecules28052249. [PMID: 36903495]
  • Paco Noriega, Lissette Calderón, Andrea Ojeda, Erika Paredes. Chemical Composition, Antimicrobial and Antioxidant Bioautography Activity of Essential Oil from Leaves of Amazon Plant Clinopodium brownei (Sw.). Molecules (Basel, Switzerland). 2023 Feb; 28(4):. doi: 10.3390/molecules28041741. [PMID: 36838728]
  • Muryam Abdul Razzaq, Waqas Younis, Muhammad Nasir Hayat Malik, Tariq G Alsahli, Alamgeer, Shah Jahan, Roma Ehsan, Arquimedes Gasparotto Junior, Asifa Bashir. Pulegone Prevents Hypertension through Activation of Muscarinic Receptors and Cyclooxygenase Pathway in L-NAME-Induced Hypertensive Rats. Cardiovascular therapeutics. 2023; 2023(?):8166840. doi: 10.1155/2023/8166840. [PMID: 37214130]
  • Chao Shou, Yu-Cong Zheng, Jing-Ru Zhan, Chun-Xiu Li, Jian-He Xu. Removing the Obstacle to (-)-Menthol Biosynthesis by Building a Microbial Cell Factory of (+)-cis-Isopulegone from (-)-Limonene. ChemSusChem. 2022 May; 15(9):e202101741. doi: 10.1002/cssc.202101741. [PMID: 34519416]
  • Mohammed Messaoudi, Abdelkrim Rebiai, Barbara Sawicka, Maria Atanassova, Hamza Ouakouak, Imane Larkem, Chukwuebuka Egbuna, Chinaza Godswill Awuchi, Sihem Boubekeur, Mohamed Amine Ferhat, Samir Begaa, Naima Benchikha. Effect of Extraction Methods on Polyphenols, Flavonoids, Mineral Elements, and Biological Activities of Essential Oil and Extracts of Mentha pulegium L. Molecules (Basel, Switzerland). 2021 Dec; 27(1):. doi: 10.3390/molecules27010011. [PMID: 35011242]
  • Haiyan Gong, Lijuan He, Zhilong Zhao, Xinmin Mao, Chen Zhang. The specific effect of (R)-(+)-pulegone on growth and biofilm formation in multi-drug resistant Escherichia coli and molecular mechanisms underlying the expression of pgaABCD genes. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Feb; 134(?):111149. doi: 10.1016/j.biopha.2020.111149. [PMID: 33385683]
  • Mohammadreza Azimi, Jalil Mehrzad, Armita Ahmadi, Elnaz Ahmadi, Ali Ghorbani Ranjbary. Apoptosis Induced by Ziziphora tenuior Essential Oil in Human Colorectal Cancer Cells. BioMed research international. 2021; 2021(?):5522964. doi: 10.1155/2021/5522964. [PMID: 34337019]
  • Qingxin Yang, Jie Luo, Hongjun Lv, Taoqun Wen, Boyu Shi, Xiaobo Liu, Nan Zeng. Pulegone inhibits inflammation via suppression of NLRP3 inflammasome and reducing cytokine production in mice. Immunopharmacology and immunotoxicology. 2019 Jun; 41(3):420-427. doi: 10.1080/08923973.2019.1588292. [PMID: 31134844]
  • I A Rosa, P Rodrigues, A E Bianchini, B P Silveira, F T Ferrari, G Bandeira Junior, A P C Vargas, B Baldisserotto, B M Heinzmann. Extracts of Hesperozygis ringens (Benth.) Epling: in vitro and in vivo antibacterial activity against fish pathogenic bacteria. Journal of applied microbiology. 2019 May; 126(5):1353-1361. doi: 10.1111/jam.14219. [PMID: 30735293]
  • Melissa Dein, John P Munafo. Characterization of Key Odorants in Hoary Mountain Mint, Pycnanthemum incanum. Journal of agricultural and food chemistry. 2019 Mar; 67(9):2589-2597. doi: 10.1021/acs.jafc.8b06803. [PMID: 30789719]
  • You Yeon Choi, Mi Hye Kim, Haesu Lee, Si Yeon Jo, Woong Mo Yang. (R)-(+)-pulegone suppresses allergic and inflammation responses on 2,4-dinitrochlorobenzene-induced atopic dermatitis in mice model. Journal of dermatological science. 2018 Sep; 91(3):292-300. doi: 10.1016/j.jdermsci.2018.06.002. [PMID: 29933898]
  • Yee Ching Ng, Ye Won Kim, Jeong-Su Lee, Sung Joon Lee, Moon Jung Song. Antiviral activity of Schizonepeta tenuifolia Briquet against noroviruses via induction of antiviral interferons. Journal of microbiology (Seoul, Korea). 2018 Sep; 56(9):683-689. doi: 10.1007/s12275-018-8228-7. [PMID: 30141161]
  • Mehdi Teymouri, Ardalan Alizadeh. Chemical composition and antimicrobial activity of the essential oil of Mentha mozaffarianii Jamzad growing wild and cultivated in Iran. Natural product research. 2018 Jun; 32(11):1320-1323. doi: 10.1080/14786419.2017.1342082. [PMID: 28658991]
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  • Efat Jafari, Gholamabbas Ghanbarian, Atefeh Bahmanzadegan. Essential oil composition of aerial parts of Micromeria persica Boiss. from Western of Shiraz, Iran. Natural product research. 2018 Apr; 32(8):991-996. doi: 10.1080/14786419.2017.1374270. [PMID: 28893105]
  • Abdelhakim Bouyahya, Abdeslam Et-Touys, Youssef Bakri, Ahmed Talbaui, Hajiba Fellah, Jamal Abrini, Nadia Dakka. Chemical composition of Mentha pulegium and Rosmarinus officinalis essential oils and their antileishmanial, antibacterial and antioxidant activities. Microbial pathogenesis. 2017 Oct; 111(?):41-49. doi: 10.1016/j.micpath.2017.08.015. [PMID: 28821401]
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  • Marzieh Piryaei, Mir Mahdi Abolghasemi, Hossein Nazemiyeh. Fast determination of Ziziphora tenuior L. essential oil by inorganic-organic hybrid material based on ZnO nanoparticles anchored to a composite made from polythiophene and hexagonally ordered silica. Natural product research. 2015; 29(9):833-7. doi: 10.1080/14786419.2014.989394. [PMID: 25496469]
  • Artur Santos-Miranda, Antonio Nei Gondim, Jose Evaldo Rodrigues Menezes-Filho, Carla Marina Lins Vasconcelos, Jader Santos Cruz, Danilo Roman-Campos. Pharmacological evaluation of R(+)-pulegone on cardiac excitability: role of potassium current blockage and control of action potential waveform. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Sep; 21(10):1146-53. doi: 10.1016/j.phymed.2014.05.007. [PMID: 24912864]
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  • Fabrizio Araniti, Elisa Graña, Manuel J Reigosa, Adela M Sánchez-Moreiras, Maria Rosa Abenavoli. Individual and joint activity of terpenoids, isolated from Calamintha nepeta extract, on Arabidopsis thaliana. Natural product research. 2013; 27(24):2297-303. doi: 10.1080/14786419.2013.827193. [PMID: 23972283]
  • Mario Chessa, Angela Sias, Andrea Piana, Giuseppe Salvatore Mangano, Giacomo Luigi Petretto, Maria Dolores Masia, Bruno Tirillini, Giorgio Pintore. Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham. Natural product research. 2013; 27(2):93-9. doi: 10.1080/14786419.2012.658798. [PMID: 22385272]
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