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 (152.12010859999998)
中文名称: (+)-长叶薄荷酮, 胡薄荷酮, 5-甲基-2-(1-甲基亚乙基)环己酮, 长叶薄荷酮
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 1.7%

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

63 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



数据库引用编号

25 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。



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]
  • Chanchan Liu, Narayanan Srividya, Amber N Parrish, Wei Yue, Mingqiu Shan, Qinan Wu, B Markus Lange. Morphology of glandular trichomes of Japanese catnip (Schizonepeta tenuifolia Briquet) and developmental dynamics of their secretory activity. Phytochemistry. 2018 Jun; 150(?):23-30. doi: 10.1016/j.phytochem.2018.02.018. [PMID: 29533838]
  • 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]
  • Mijat Božović, Rino Ragno. Calamintha nepeta (L.) Savi and its Main Essential Oil Constituent Pulegone: Biological Activities and Chemistry. Molecules (Basel, Switzerland). 2017 Feb; 22(2):. doi: 10.3390/molecules22020290. [PMID: 28216606]
  • M S Abu-Darwish, C Cabral, M J Gonçalves, C Cavaleiro, M T Cruz, M Paoli, F Tomi, T Efferth, L Salgueiro. Ziziphora tenuior L. essential oil from Dana Biosphere Reserve (Southern Jordan); Chemical characterization and assessment of biological activities. Journal of ethnopharmacology. 2016 Dec; 194(?):963-970. doi: 10.1016/j.jep.2016.10.076. [PMID: 27815078]
  • Dragana Stojičić, Svetlana Tošić, Violeta Slavkovska, Bojan Zlatković, Snežana Budimir, Dušica Janošević, Branka Uzelac. Glandular trichomes and essential oil characteristics of in vitro propagated Micromeria pulegium (Rochel) Benth. (Lamiaceae). Planta. 2016 Aug; 244(2):393-404. doi: 10.1007/s00425-016-2513-7. [PMID: 27074837]
  • E Darvishi, D Kahrizi, S Bahraminejad, M Mansouri. In vitro induction of α-pinene, pulegone, menthol, menthone and limonene in cell suspension culture of pennyroyal (Mentha pulegium). Cellular and molecular biology (Noisy-le-Grand, France). 2016 Mar; 62(3):7-9. doi: . [PMID: 27064866]
  • Prawez Alam, Mahmoud Fayez Saleh, Maged Saad Abdel-Kader. Quantitative estimation of pulegone in Mentha longifolia growing in Saudi Arabia. Is it safe to use?. Pakistan journal of pharmaceutical sciences. 2016 Mar; 29(2):389-96. doi: . [PMID: 27087088]
  • Zheng Jiang, Hong Wang, Qi-nan Wu, Wei Yue, Da-wei Wu, Xiu-he Fan. [Qualitative and Quantitative Analysis of Major Constituents of Gland Products in Peltate Glandular Trichomes of Schizonepetae Spica]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2016 Jan; 39(1):31-6. doi: ". [PMID: 30079698]
  • Yukari Sunohara, Yohei Baba, Shigeru Matsuyama, Kaori Fujimura, Hiroshi Matsumoto. Screening and identification of phytotoxic volatile compounds in medicinal plants and characterizations of a selected compound, eucarvone. Protoplasma. 2015 Jul; 252(4):1047-59. doi: 10.1007/s00709-014-0739-4. [PMID: 25534256]
  • Guanying Hu, Xing Yuan, Sanyin Zhang, Ruru Wang, Miao Yang, Chunjie Wu, Zhigang Wu, Xiao Ke. Research on choleretic effect of menthol, menthone, pluegone, isomenthone, and limonene in DanShu capsule. International immunopharmacology. 2015 Feb; 24(2):191-197. doi: 10.1016/j.intimp.2014.12.001. [PMID: 25499726]
  • Franco Matías Escobar, María Carola Sabini, Laura Noelia Cariddi, Liliana Inés Sabini, Fernando Mañas, Andrea Cristofolini, Guillermo Bagnis, Mauro Nicolas Gallucci, Lilia Renée Cavaglieri. Safety assessment of essential oil from Minthostachys verticillata (Griseb.) Epling (peperina): 90-days oral subchronic toxicity study in rats. Regulatory toxicology and pharmacology : RTP. 2015 Feb; 71(1):1-7. doi: 10.1016/j.yrtph.2014.11.001. [PMID: 25445298]
  • 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]
  • He Qin Li, Qi Zhi Liu, Zhi Long Liu, Shu Shan Du, Zhi Wei Deng. Chemical composition and nematicidal activity of essential oil of Agastache rugosa against Meloidogyne incognita. Molecules (Basel, Switzerland). 2013 Apr; 18(4):4170-80. doi: 10.3390/molecules18044170. [PMID: 23571530]
  • Alexandra Esther, Ralf Tilcher, Jens Jacob. Assessing the effects of three potential chemical repellents to prevent bird damage to corn seeds and seedlings. Pest management science. 2013 Mar; 69(3):425-30. doi: 10.1002/ps.3288. [PMID: 22499556]
  • 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]
  • Fabrizio Araniti, Antonio Lupini, Agostino Sorgonà, Filomena Conforti, Mariangela Marrelli, Giancarlo Antonio Statti, Francesco Menichini, Maria Rosa Abenavoli. Allelopathic potential of Artemisia arborescens: isolation, identification and quantification of phytotoxic compounds through fractionation-guided bioassays. Natural product research. 2013; 27(10):880-7. doi: 10.1080/14786419.2012.691491. [PMID: 22687059]
  • A Kasrati, C Alaoui Jamali, K Bekkouche, H Lahcen, M Markouk, H Wohlmuth, D Leach, A Abbad. Essential oil composition and antimicrobial activity of wild and cultivated mint timija (Mentha suaveolens subsp. timija (Briq.) Harley), an endemic and threatened medicinal species in Morocco. Natural product research. 2013; 27(12):1119-22. doi: 10.1080/14786419.2012.708661. [PMID: 22838406]
  • Diana Dobravalskytė, Petras Rimantas Venskutonis, Thierry Talou. Antioxidant properties and essential oil composition of Calamintha grandiflora L. Food chemistry. 2012 Dec; 135(3):1539-46. doi: 10.1016/j.foodchem.2012.05.094. [PMID: 22953891]
  • Pedro Marcos Gomes Soares, Alana de Freitas Pires, Emmanuel Prata de Souza, Ana Maria Sampaio Assreuy, David Neil Criddle. Relaxant effects of the essential oil of Mentha pulegium L. in rat isolated trachea and urinary bladder. The Journal of pharmacy and pharmacology. 2012 Dec; 64(12):1777-84. doi: 10.1111/j.2042-7158.2012.01558.x. [PMID: 23146041]
  • Franco Matías Escobar, Laura Noelia Cariddi, María Carola Sabini, Elina Reinoso, Sonia Beatriz Sutil, Cristina Vanesa Torres, Silvia Matilde Zanon, Liliana Inés Sabini. Lack of cytotoxic and genotoxic effects of Minthostachys verticillata essential oil: studies in vitro and in vivo. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Sep; 50(9):3062-7. doi: 10.1016/j.fct.2012.06.018. [PMID: 22727859]
  • Emine Nur Herken, Ali Celik, Mustafa Aslan, Nilüfer Aydınlık. The constituents of essential oil: antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia. Journal of medicinal food. 2012 Sep; 15(9):835-9. doi: 10.1089/jmf.2011.0315. [PMID: 22871061]
  • Fan Tong, Joel R Coats. Quantitative structure-activity relationships of monoterpenoid binding activities to the housefly GABA receptor. Pest management science. 2012 Aug; 68(8):1122-9. doi: 10.1002/ps.3280. [PMID: 22461383]
  • Mitscheli S Da Rocha, Puttappa R Dodmane, Lora L Arnold, Karen L Pennington, Muhammad M Anwar, Bret R Adams, Sean V Taylor, Clint Wermes, Timothy B Adams, Samuel M Cohen. Mode of action of pulegone on the urinary bladder of F344 rats. Toxicological sciences : an official journal of the Society of Toxicology. 2012 Jul; 128(1):1-8. doi: 10.1093/toxsci/kfs135. [PMID: 22499580]
  • Naglaa Gamil Shehab, Eman Abu-Gharbieh. Constituents and biological activity of the essential oil and the aqueous extract of Micromeria fruticosa (L.) Druce subsp. serpyllifolia. Pakistan journal of pharmaceutical sciences. 2012 Jul; 25(3):687-92. doi: . [PMID: 22713962]
  • Regina Karousou, Effie Hanlidou, Diamando Lazari. Essential-oil diversity of three Calamintha species from Greece. Chemistry & biodiversity. 2012 Jul; 9(7):1364-72. doi: 10.1002/cbdv.201100262. [PMID: 22782882]
  • Niko S Radulović, Polina D Blagojević. Volatile secondary metabolites of Micromeria dalmatica Benth. (Lamiaceae): biosynthetical and chemotaxonomical aspects. Chemistry & biodiversity. 2012 Jul; 9(7):1303-19. doi: 10.1002/cbdv.201100429. [PMID: 22782877]
  • Sung-Hwa Sohn, Sunim Cho, Eun Seok Ji, Sung-Hoon Kim, Minkyu Shin, Moochang Hong, Hyunsu Bae. Microarray analysis of the gene expression profile of HMC-1 mast cells following Schizonepeta tenuifolia Briquet treatment. Cellular immunology. 2012 May; 277(1-2):58-65. doi: 10.1016/j.cellimm.2012.05.012. [PMID: 22726350]
  • Ranil Waliwitiya, Russell A Nicholson, Christopher J Kennedy, Carl A Lowenberger. The synergistic effects of insecticidal essential oils and piperonyl butoxide on biotransformational enzyme activities in Aedes aegypti (Diptera: Culicidae). Journal of medical entomology. 2012 May; 49(3):614-23. doi: 10.1603/me10272. [PMID: 22679869]
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