cis-Isopulegone (BioDeep_00000020567)

   

human metabolite Endogenous Volatile Flavor Compounds natural product


代谢物信息卡片


[4-(prop-1-en-2-yl)cyclohexyl]methanol

化学式: C10H18O (154.1357578)
中文名称: [4-（丙-1-烯-2-基）环己基]甲醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C(C)C1CCC(CO)CC1
InChI: InChI=1S/C10H18O/c1-8(2)10-5-3-9(7-11)4-6-10/h9-11H,1,3-7H2,2H3

描述信息

cis-Isopulegone is found in fats and oils. cis-Isopulegone is a minor constituent of Perilla species.
Minor constituent of Perilla subspecies cis-Isopulegone is found in fats and oils.

同义名列表

10 个代谢物同义名

[4-(prop-1-en-2-yl)cyclohexyl]methanol; cis-P-Menth-8-en-7-ol; pulegone, (R)-isomer; pulegone, (S)-isomer; cis-isopulegone; trans-Shisool; isopulegone; Pulegone; [4-(Prop-1-en-2-yl)cyclohexyl]methanol; trans-Shisool



数据库引用编号

10 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)

21 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Yanina Estefanía Rossi, Lilián Canavoso, Sara María Palacios. Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)+-pulegone and menthone. Fitoterapia. 2012 Mar; 83(2):336-42. doi: 10.1016/j.fitote.2011.11.019. [PMID: 22155595]
  • Alessandra Bertoli, Michele Leonardi, Justyna Krzyzanowska, Wieslaw Oleszek, Luisa Pistelli. In vitro production of M. × piperita not containing pulegone and menthofuran. Acta biochimica Polonica. 2012; 59(3):417-23. doi: . [PMID: 22946028]
  • Charalabos D Kanakis, Eleftherios A Petrakis, Athanasios C Kimbaris, Christos Pappas, Petros A Tarantilis, Moschos G Polissiou. Classification of Greek Mentha pulegium L. (Pennyroyal) samples, according to geographical location by Fourier transform infrared spectroscopy. Phytochemical analysis : PCA. 2012 Jan; 23(1):34-43. doi: 10.1002/pca.1322. [PMID: 21618307]
  • Sandra Valeria Santos de Cerqueira, Antonio Nei Santana Gondim, Danilo Roman-Campos, Jader Santos Cruz, Amilton Gustavo da Silva Passos, Sandra Lauton-Santos, Aline Lara, Silvia Guatimosim, Eduardo Antonio Conde-Garcia, Evaleide Diniz de Oliveira, Carla Maria Lins de Vasconcelos. R(+)-pulegone impairs Ca²+ homeostasis and causes negative inotropism in mammalian myocardium. European journal of pharmacology. 2011 Dec; 672(1-3):135-42. doi: 10.1016/j.ejphar.2011.09.186. [PMID: 22004607]
  • Ali Reza Khosravi, Hojjatollah Shokri, Mohammadhassan Minooeianhaghighi. Inhibition of aflatoxin production and growth of Aspergillus parasiticus by Cuminum cyminum, Ziziphora clinopodioides, and Nigella sativa essential oils. Foodborne pathogens and disease. 2011 Dec; 8(12):1275-80. doi: 10.1089/fpd.2011.0929. [PMID: 21861703]
  • Maricel Valeria Santoro, Julio Zygadlo, Walter Giordano, Erika Banchio. Volatile organic compounds from rhizobacteria increase biosynthesis of essential oils and growth parameters in peppermint (Mentha piperita). Plant physiology and biochemistry : PPB. 2011 Oct; 49(10):1177-82. doi: 10.1016/j.plaphy.2011.07.016. [PMID: 21843946]
  • . Toxicology and carcinogenesis studies of pulegone (CAS No. 89-82-7) in F344/N rats and B6C3F1 mice (gavage studies). National Toxicology Program technical report series. 2011 Aug; ?(563):1-201. doi: . [PMID: 21921962]
  • Paola Gonzalez-Audino, María Inés Picollo, Anabella Gallardo, Ariel Toloza, Claudia Vassena, Gastón Mougabure-Cueto. Comparative toxicity of oxygenated monoterpenoids in experimental hydroalcoholic lotions to permethrin-resistant adult head lice. Archives of dermatological research. 2011 Jul; 303(5):361-6. doi: 10.1007/s00403-010-1110-z. [PMID: 21174108]
  • Zhi Long Liu, Sha Sha Chu, Guo Hua Jiang. Toxicity of Schizonpeta multifida essential oil and its constituent compounds towards two grain storage insects. Journal of the science of food and agriculture. 2011 Mar; 91(5):905-9. doi: 10.1002/jsfa.4263. [PMID: 21384358]
  • E Viveros-Valdez, C Rivas-Morales, A Oranday-Cardenas, M J Verde-Star, P Carranza-Rosales. Antimicrobial activity of Hedeoma drummondii against opportunistic pathogens. Pakistan journal of biological sciences : PJBS. 2011 Feb; 14(4):305-7. doi: 10.3923/pjbs.2011.305.307. [PMID: 21870634]
  • Sheng Yu, Yiwen Chen, Li Zhang, Mingqiu Shan, Yuping Tang, Anwei Ding. Quantitative comparative analysis of the bio-active and toxic constituents of leaves and spikes of Schizonepeta tenuifolia at different harvesting times. International journal of molecular sciences. 2011; 12(10):6635-44. doi: 10.3390/ijms12106635. [PMID: 22072908]
  • Niko S Radulović, Polina D Blagojević. Plant volatiles providing additional evidences to the occurence of a wild-growing population of Calamintha vardarensis (Greuter et Burdet) Šilić outside of its natural habitat. Chemistry & biodiversity. 2010 Dec; 7(12):2856-68. doi: 10.1002/cbdv.201000144. [PMID: 21161998]
  • B Marongiu, A Piras, S Porcedda, D Falconieri, A Maxia, M J Gonçalves, C Cavaleiro, L Salgueiro. Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae). Natural product research. 2010 Nov; 24(18):1734-42. doi: 10.1080/14786410903108944. [PMID: 20981614]
  • Vera Lucia Sardá Ribeiro, Jaqueline Campiol Dos Santos, Sérgio A L Bordignon, Miriam A Apel, Amélia T Henriques, Gilsane L von Poser. Acaricidal properties of the essential oil from Hesperozygis ringens (Lamiaceae) on the cattle tick Riphicephalus (Boophilus) microplus. Bioresource technology. 2010 Apr; 101(7):2506-9. doi: 10.1016/j.biortech.2009.11.016. [PMID: 19954969]
  • Eleftherios A Petrakis, Athanasios C Kimbaris, Christos S Pappas, Petros A Tarantilis, Moschos G Polissiou. Quantitative determination of pulegone in pennyroyal oil by FT-IR spectroscopy. Journal of agricultural and food chemistry. 2009 Nov; 57(21):10044-8. doi: 10.1021/jf9026052. [PMID: 19817373]
  • Jian-xia Mo, Cheng Jiang, Xia-yan Zhang. [Studies on characteristics of volatile oil and micro-identification between Herba Pogostemonis and Herba Agastachis rugosae]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Nov; 32(11):1675-7. doi: ". [PMID: 20218287]
  • Mounira Mkaddem, Jalloul Bouajila, Monia Ennajar, Ahmed Lebrihi, Florence Mathieu, Mehrez Romdhane. Chemical composition and antimicrobial and antioxidant activities of Mentha (longifolia L. and viridis) essential oils. Journal of food science. 2009 Sep; 74(7):M358-63. doi: 10.1111/j.1750-3841.2009.01272.x. [PMID: 19895481]
  • Suzana V Brankovic, Dusanka V Kitic, Mirjana M Radenkovic, Slavimir M Veljkovic, Tatjana D Golubovic. Calcium blocking activity as a mechanism of the spasmolytic effect of the essential oil of Calamintha glandulosa Silic on the isolated rat ileum. General physiology and biophysics. 2009; 28 Spec No(?):174-8. doi: ". [PMID: 19893097]
  • Damião P de Sousa, Genival A S Júnior, Luciana N Andrade, Flávia R Calasans, Xirley P Nunes, José M Barbosa-Filho, Josemar S Batista. Structure and spasmolytic activity relationships of monoterpene analogues found in many aromatic plants. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2008 Nov; 63(11-12):808-12. doi: 10.1515/znc-2008-11-1205. [PMID: 19227827]
  • Dietland Müller-Schwarze, Vera Thoss. Defense on the rocks: low monoterpenoid levels in plants on pillars without mammalian herbivores. Journal of chemical ecology. 2008 Nov; 34(11):1377-81. doi: 10.1007/s10886-008-9543-y. [PMID: 18925383]
  • Hee Kang, Yoo-Joung Oh, Ho-Young Choi, In-Hye Ham, Hyun-Su Bae, Sung-Hoon Kim, Kyoo-Seok Ahn. Immunomodulatory effect of Schizonepeta tenuifolia water extract on mouse Th1/Th2 cytokine production in-vivo and in-vitro. The Journal of pharmacy and pharmacology. 2008 Jul; 60(7):901-7. doi: 10.1211/jpp.60.7.0012. [PMID: 18549677]
  • Rigoberto Rios-Estepa, Glenn W Turner, James M Lee, Rodney B Croteau, B Markus Lange. A systems biology approach identifies the biochemical mechanisms regulating monoterpenoid essential oil composition in peppermint. Proceedings of the National Academy of Sciences of the United States of America. 2008 Feb; 105(8):2818-23. doi: 10.1073/pnas.0712314105. [PMID: 18287058]
  • Ling-Jen Chen Ferguson, Edward H Lebetkin, Fred B Lih, Kenneth B Tomer, Horace D Parkinson, Susan J Borghoff, Leo T Burka. 14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. Journal of toxicology and environmental health. Part A. 2007 Sep; 70(17):1416-23. doi: 10.1080/15287390701382720. [PMID: 17687727]
  • Qin Qiu, Jianya Ling, Yuping Ding, Hongwen Chang, Jiang Wang, Tingli Liu. [Comparison of supercritical fluid extraction and steam distillation methods for the extraction of essential oils from Schizonepeta tenuifolia Briq]. Se pu = Chinese journal of chromatography. 2005 Nov; 23(6):646-50. doi: ". [PMID: 16498998]
  • Erika Banchio, Julio Zygadlo, Graciela R Valladares. Quantitative variations in the essential oil of Minthostachys mollis (Kunth.) Griseb. in response to insects with different feeding habits. Journal of agricultural and food chemistry. 2005 Aug; 53(17):6903-6. doi: 10.1021/jf051157j. [PMID: 16104818]
  • Jian-ping Yang, Bei-hua Bao, Li Zhang, An-wei Ding. [Quantitative analysis of pulegone in Herba Schizonepetae]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 May; 30(9):669-70. doi: ". [PMID: 16075729]
  • Erika Banchio, Julio Zygadlo, Graciela R Valladares. Effects of mechanical wounding on essential oil composition and emission of volatiles from Minthostachys mollis. Journal of chemical ecology. 2005 Apr; 31(4):719-27. doi: 10.1007/s10886-005-3540-1. [PMID: 16124247]
  • P M Soares, A M S Assreuy, E P Souza, R F Lima, T O Silva, S R Fontenele, D N Criddle. Inhibitory effects of the essential oil of Mentha pulegium on the isolated rat myometrium. Planta medica. 2005 Mar; 71(3):214-8. doi: 10.1055/s-2005-837819. [PMID: 15770540]
  • F Siano, M Catalfamo, D Cautela, L Servillo, D Castaldo. Analysis of pulegone and its enanthiomeric distribution in mint-flavoured food products. Food additives and contaminants. 2005 Mar; 22(3):197-203. doi: 10.1080/02652030500041581. [PMID: 16019787]
  • Mehmet Emin Duru, Mehmet Oztürk, Aysel Uğur, Ozgür Ceylan. The constituents of essential oil and in vitro antimicrobial activity of Micromeria cilicica from Turkey. Journal of ethnopharmacology. 2004 Sep; 94(1):43-8. doi: 10.1016/j.jep.2004.03.053. [PMID: 15261961]
  • Michael Thomsen, Luis Vitetta, Avni Sali, Matthias Schmidt. Acute liver failure associated with the use of herbal preparations containing black cohosh. The Medical journal of Australia. 2004 Jun; 180(11):598-9; author reply 599. doi: 10.5694/j.1326-5377.2004.tb06109.x. [PMID: 15175000]
  • Shufeng Zhou, Hwee-Ling Koh, Yihuai Gao, Zhi-yuan Gong, Edmund Jon Deoon Lee. Herbal bioactivation: the good, the bad and the ugly. Life sciences. 2004 Jan; 74(8):935-68. doi: 10.1016/j.lfs.2003.09.035. [PMID: 14672753]
  • Soheil S Mahmoud, Rodney B Croteau. Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. Proceedings of the National Academy of Sciences of the United States of America. 2003 Nov; 100(24):14481-6. doi: 10.1073/pnas.2436325100. [PMID: 14623962]
  • Wolfgang Engel. In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone. Journal of agricultural and food chemistry. 2003 Oct; 51(22):6589-97. doi: 10.1021/jf034702u. [PMID: 14558782]
  • Kerry L Ringer, Marie E McConkey, Edward M Davis, Gary W Rushing, Rodney Croteau. Monoterpene double-bond reductases of the (-)-menthol biosynthetic pathway: isolation and characterization of cDNAs encoding (-)-isopiperitenone reductase and (+)-pulegone reductase of peppermint. Archives of biochemistry and biophysics. 2003 Oct; 418(1):80-92. doi: 10.1016/s0003-9861(03)00390-4. [PMID: 13679086]
  • Matthew D Sztajnkrycer, Edward J Otten, G Randall Bond, Christopher J Lindsell, Robert J Goetz. Mitigation of pennyroyal oil hepatotoxicity in the mouse. Academic emergency medicine : official journal of the Society for Academic Emergency Medicine. 2003 Oct; 10(10):1024-8. doi: 10.1111/j.1553-2712.2003.tb00569.x. [PMID: 14525732]
  • L-J Chen, E H Lebetkin, L T Burka. Comparative disposition of (R)-(+)-pulegone in B6C3F1 mice and F344 rats. Drug metabolism and disposition: the biological fate of chemicals. 2003 Jul; 31(7):892-9. doi: 10.1124/dmd.31.7.892. [PMID: 12814966]
  • H Oumzil, S Ghoulami, M Rhajaoui, A Ilidrissi, S Fkih-Tetouani, M Faid, A Benjouad. Antibacterial and antifungal activity of essential oils of Mentha suaveolens. Phytotherapy research : PTR. 2002 Dec; 16(8):727-31. doi: 10.1002/ptr.1045. [PMID: 12458474]
  • Dimitra J Daferera, Petros A Tarantilis, Moschos G Polissiou. Characterization of essential oils from lamiaceae species by fourier transform Raman spectroscopy. Journal of agricultural and food chemistry. 2002 Sep; 50(20):5503-7. doi: 10.1021/jf0203489. [PMID: 12236670]
  • Graciela R Valladares, Adriana Zapata, Julio Zygadlo, Erika Banchio. Phytochemical induction by herbivores could affect quality of essential oils from aromatic plants. Journal of agricultural and food chemistry. 2002 Jul; 50(14):4059-61. doi: 10.1021/jf011608+. [PMID: 12083883]
  • L J Chen, E H Lebetkin, L T Burka. Metabolism of (R)-(+)-pulegone in F344 rats. Drug metabolism and disposition: the biological fate of chemicals. 2001 Dec; 29(12):1567-77. doi: . [PMID: 11717176]
  • M Maffei, W Camusso, S Sacco. Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential. Phytochemistry. 2001 Nov; 58(5):703-7. doi: 10.1016/s0031-9422(01)00313-2. [PMID: 11672734]
  • C M Bertea, M Schalk, F Karp, M Maffei, R Croteau. Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene. Archives of biochemistry and biophysics. 2001 Jun; 390(2):279-86. doi: 10.1006/abbi.2001.2378. [PMID: 11396930]
  • H V Thulasiram, V B Bhat, M K Madyastha. Effect of ring size in R-(+)-pulegone-mediated hepatotoxicity: studies on the metabolism of R-(+)-4-methyl-2-(1-methylethylidene)-cyclopentanone and DL-camphorone in rats. Drug metabolism and disposition: the biological fate of chemicals. 2001 Jun; 29(6):821-9. doi: NULL. [PMID: 11353750]
  • M Mucciarelli, W Camusso, C M Bertea, M Maffei. Effect of (+)-pulegone and other oil components of Mentha x Piperita on cucumber respiration. Phytochemistry. 2001 May; 57(1):91-8. doi: 10.1016/s0031-9422(00)00393-9. [PMID: 11336266]
  • S Fuchs, T Beck, A Mosandl. Different stereoselectivity in the reduction of pulegone by Mentha species. Planta medica. 2001 Apr; 67(3):260-2. doi: 10.1055/s-2001-11992. [PMID: 11345699]
  • V Primo, M Rovera, S Zanon, M Oliva, M Demo, J Daghero, L Sabini. [Determination of the antibacterial and antiviral activity of the essential oil from Minthostachys verticillata (Griseb.) Epling]. Revista Argentina de microbiologia. 2001 Apr; 33(2):113-7. doi: ". [PMID: 11494754]
  • B Nair. Final report on the safety assessment of Mentha Piperita (Peppermint) Oil, Mentha Piperita (Peppermint) Leaf Extract, Mentha Piperita (Peppermint) Leaf, and Mentha Piperita (Peppermint) Leaf Water. International journal of toxicology. 2001; 20 Suppl 3(?):61-73. doi: . [PMID: 11766133]
  • H V Thulasiram, A K Gadad, M K Madyastha. Role of C-5 chiral center in R-(+)-pulegone-mediated hepatotoxicity: metabolic disposition and toxicity of 5, 5-dimethyl-2-(1-Methylethylidene)-cyclohexanone in rats. Drug metabolism and disposition: the biological fate of chemicals. 2000 Jul; 28(7):833-44. doi: . [PMID: 10859158]
  • S Fuchs, S Zinn, T Beck, A Mosandl. Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies. Journal of agricultural and food chemistry. 1999 Oct; 47(10):4100-5. doi: 10.1021/jf990439e. [PMID: 10552773]
  • B B Vadiraja, N W Gaikwad, K M Madyastha. Hepatoprotective effect of C-phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats. Biochemical and biophysical research communications. 1998 Aug; 249(2):428-31. doi: 10.1006/bbrc.1998.9149. [PMID: 9712713]
  • K M Madyastha, N W Gaikwad. Metabolic fate of S-(-)-pulegone in rat. Xenobiotica; the fate of foreign compounds in biological systems. 1998 Aug; 28(8):723-34. doi: 10.1080/004982598239146. [PMID: 9741951]
  • A M Mølck, M Poulsen, S Tindgard Lauridsen, P Olsen. Lack of histological cerebellar changes in Wistar rats given pulegone for 28 days. Comparison of immersion and perfusion tissue fixation. Toxicology letters. 1998 Mar; 95(2):117-22. doi: 10.1016/s0378-4274(98)00029-0. [PMID: 9635415]
  • I B Anderson, W H Mullen, J E Meeker, Khojasteh-BakhtSC, S Oishi, S D Nelson, P D Blanc. Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature. Annals of internal medicine. 1996 Apr; 124(8):726-34. doi: 10.7326/0003-4819-124-8-199604150-00004. [PMID: 8633832]
  • Z Kalodera, S Pepeljnjak, S Vladimir, N Blazević. Antimicrobial activity of essential oil from Micromeria thymifolia (Scop.) Fritsch. Die Pharmazie. 1994 May; 49(5):376-7. doi: ". [PMID: 8016187]
  • K M Madyastha, C P Raj. Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites. Xenobiotica; the fate of foreign compounds in biological systems. 1993 May; 23(5):509-18. doi: 10.3109/00498259309059391. [PMID: 8342298]
  • D Thomassen, J T Slattery, S D Nelson. Menthofuran-dependent and independent aspects of pulegone hepatotoxicity: roles of glutathione. The Journal of pharmacology and experimental therapeutics. 1990 May; 253(2):567-72. doi: . [PMID: 2338648]
  • B Moorthy, P Madyastha, K M Madyastha. Hepatotoxicity of pulegone in rats: its effects on microsomal enzymes, in vivo. Toxicology. 1989 May; 55(3):327-37. doi: 10.1016/0300-483x(89)90022-x. [PMID: 2541521]
  • B Moorthy, P Madyastha, K M Madyastha. Metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat. Xenobiotica; the fate of foreign compounds in biological systems. 1989 Feb; 19(2):217-24. doi: 10.3109/00498258909034694. [PMID: 2728495]
  • D Thomassen, J T Slattery, S D Nelson. Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. The Journal of pharmacology and experimental therapeutics. 1988 Mar; 244(3):825-9. doi: . [PMID: 3252034]
  • T Mizutani, H Nomura, K Nakanishi, S Fujita. Effects of drug metabolism modifiers on pulegone-induced hepatotoxicity in mice. Research communications in chemical pathology and pharmacology. 1987 Oct; 58(1):75-83. doi: . [PMID: 3432735]
  • M Montes, L Valenzuela, T Wilkomirsky, C Niedmann. [Determination of pulegone in the essential oil of Mentha pulegium L. from Chile]. Annales pharmaceutiques francaises. 1986; 44(2):133-6. doi: ". [PMID: 3777785]