Nepetalactone (BioDeep_00001867542)

Main id: BioDeep_00000000699

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS-(4aalpha,7alpha,7aalpha))-

化学式: C10H14O2 (166.0994)
中文名称: 顺反式荆芥内酯
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC([C@]1([H])[C@@]2([H])[C@H](CC1)C)=COC2=O
InChI: InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3/t6-,8+,9+/m0/s1

描述信息

Cis-trans-nepetalactone is a cyclopentapyran that is (4aS,7aR)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aS,7S,7aR-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It is an aphid sex pheromone and cat attractant, and exhibits antibacterial, antifungal, and analgesic properties. It has a role as a pheromone, a plant metabolite, an insect attractant, an analgesic, an insect repellent, an antibacterial agent and an antifungal agent. It is an iridoid monoterpenoid and a cyclopentapyran.
Nepetalactone cis-trans-form is a natural product found in Nepeta cataria, Nepeta tuberosa, and Nepeta racemosa with data available.
A cyclopentapyran that is (4aS,7aR)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aS,7S,7aR-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It is an aphid sex pheromone and cat attractant, and exhibits antibacterial, antifungal, and analgesic properties.
4aα,7α,7aα-Nepetalactone exhibits antibacterial activity, and inhibits Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhi and Enterococcus faecalis.

同义名列表

28 个代谢物同义名

Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS-(4aalpha,7alpha,7aalpha))-; Cyclopenta[c]pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aR)-; Cyclopenta(c)pyran-1(4aH)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, (4aS,7S,7aR)-; (4aS)-5,6,7,7aalpha-tetrahydro-4,7alpha-dimethylcyclopenta[c]pyran-1(4aH)-one; (4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4aH)-one; (4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one; (4aS,7S,7aR)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-1-one; nepetalactone, (4aR-(4aalpha,7beta,7aalpha))-isomer; nepetalactone, (4aalpha,7alpha,7abeta)-isomer; 4a.alpha.,7.alpha.,7a.alpha.-Nepetalactone; 4a alpha,7 alpha,7 alpha-Nepetalactone; 4aalpha,7alpha,7aalpha-Nepetalactone; NEPETALACTONE CIS-TRANS-FORM [MI]; Nepetalactone, (+)-(4AS,7S,7AR)-; (+)-(4aS,7S,7aR)-Nepetalactone; Nepetalactone cis-trans-form; (+)-cis,trans-Nepetalactone; 4a|A,7|A,7a|A-Nepetalactone; ZDKZHVNKFOXMND-NBEYISGCSA-N; (4aS,7S,7aR)-nepetalactone; 4aα,7α,7aα-Nepetalactone; cis-trans-Nepetalactone; Z,E-NEPETALACTONE; UNII-7TM7PE24UW; nepetalactone; NEPETALACTON; 7TM7PE24UW; Nepetalactone cis-trans-form



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

74 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

  • Samuel J Smit, Sefa Ayten, Barbara A Radzikowska, John P Hamilton, Swen Langer, William P Unsworth, Tony R Larson, C Robin Buell, Benjamin R Lichman. The genomic and enzymatic basis for iridoid biosynthesis in cat thyme (Teucrium marum). The Plant journal : for cell and molecular biology. 2024 Jun; 118(5):1589-1602. doi: 10.1111/tpj.16698. [PMID: 38489316]
  • Erik Nunes Gomes, Bo Yuan, Harna K Patel, Anthony Lockhart, Christian A Wyenandt, Qingli Wu, James E Simon. Implications of the Propagation Method for the Phytochemistry of Nepeta cataria L. throughout a Growing Season. Molecules (Basel, Switzerland). 2024 Apr; 29(9):. doi: 10.3390/molecules29092001. [PMID: 38731491]
  • Cassie Sims, Michael A Birkett, Neil J Oldham, Robert A Stockman, David M Withall. Pea aphid odorant-binding protein OBP6 discriminates between aphid sex pheromone components, aphid alarm pheromones and host plant volatiles. Insect biochemistry and molecular biology. 2023 Oct; ?(?):104026. doi: 10.1016/j.ibmb.2023.104026. [PMID: 37827436]
  • Gunjan Tiwari, Trishna Chaturvedi, Anil Kumar Gupta, Raj Kishori Lal, Ram Swaroop Verma, Ramesh Kumar Srivastava, Pooja Singh, Bhavana Gangwar, M P Darokar, Sunita Singh Dhawan. Assessment of Genetic Diversity, Micromorphology and Antimicrobial Activity in Nepeta cataria L. Chemistry & biodiversity. 2023 Feb; 20(2):e202200241. doi: 10.1002/cbdv.202200241. [PMID: 36655301]
  • Christophe Duplais, Nicolas Papon, Vincent Courdavault. Tracking the Origin and Evolution of Plant Metabolites. Trends in plant science. 2020 12; 25(12):1182-1184. doi: 10.1016/j.tplants.2020.08.010. [PMID: 32896488]
  • Neda Aničić, Dragana Matekalo, Marijana Skorić, Jasmina Nestorović Živković, Luka Petrović, Milan Dragićević, Slavica Dmitrović, Danijela Mišić. Alterations in nepetalactone metabolism during polyethylene glycol (PEG)-induced dehydration stress in two Nepeta species. Phytochemistry. 2020 Jun; 174(?):112340. doi: 10.1016/j.phytochem.2020.112340. [PMID: 32172017]
  • Benjamin R Lichman, Grant T Godden, John P Hamilton, Lira Palmer, Mohamed O Kamileen, Dongyan Zhao, Brieanne Vaillancourt, Joshua C Wood, Miao Sun, Taliesin J Kinser, Laura K Henry, Carlos Rodriguez-Lopez, Natalia Dudareva, Douglas E Soltis, Pamela S Soltis, C Robin Buell, Sarah E O'Connor. The evolutionary origins of the cat attractant nepetalactone in catnip. Science advances. 2020 05; 6(20):eaba0721. doi: 10.1126/sciadv.aba0721. [PMID: 32426505]
  • Lira Palmer, Sarah E O'Connor. Virus-Induced Gene Silencing in Nepeta. Methods in molecular biology (Clifton, N.J.). 2020; 2172(?):111-121. doi: 10.1007/978-1-0716-0751-0_9. [PMID: 32557365]
  • Slavica Dmitrović, Milan Dragićević, Jelena Savić, Milica Milutinović, Suzana Živković, Vuk Maksimović, Dragana Matekalo, Danijela Mišić. Nepetalactone-rich essential oil mitigates phosphinothricin-induced ammonium toxicity in Arabidopsis thaliana (L.) Heynh. Journal of plant physiology. 2019 Jun; 237(?):87-94. doi: 10.1016/j.jplph.2019.04.006. [PMID: 31034969]
  • William Reichert, Jadrian Ejercito, Tom Guda, Xujun Dong, Qingli Wu, Anandasankar Ray, James E Simon. Repellency Assessment of Nepeta cataria Essential Oils and Isolated Nepetalactones on Aedes aegypti. Scientific reports. 2019 02; 9(1):1524. doi: 10.1038/s41598-018-36814-1. [PMID: 30728370]
  • Nathaniel H Sherden, Benjamin Lichman, Lorenzo Caputi, Dongyan Zhao, Mohamed O Kamileen, C Robin Buell, Sarah E O'Connor. Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry. Phytochemistry. 2018 Jan; 145(?):48-56. doi: 10.1016/j.phytochem.2017.10.004. [PMID: 29091815]
  • Sebastiaan Bol, Jana Caspers, Lauren Buckingham, Gail Denise Anderson-Shelton, Carrie Ridgway, C A Tony Buffington, Stefan Schulz, Evelien M Bunnik. Responsiveness of cats (Felidae) to silver vine (Actinidia polygama), Tatarian honeysuckle (Lonicera tatarica), valerian (Valeriana officinalis) and catnip (Nepeta cataria). BMC veterinary research. 2017 Mar; 13(1):70. doi: 10.1186/s12917-017-0987-6. [PMID: 28302120]
  • M Dehghany Ashkezary, F Aboee-Mehrizi, P Moradi. SiO2@antisense molecules covered by nepetalactone, extracted from Nepeta gloeocephala, inhibits ILK phosphorylation and downstream PKB/AKT signaling in HeLa cells. Cancer gene therapy. 2017 Jan; 24(1):28-32. doi: 10.1038/cgt.2016.75. [PMID: 27982018]
  • Sándor Koczor, Ferenc Szentkirályi, John A Pickett, Michael A Birkett, Miklós Tóth. Aphid Sex Pheromone Compounds Interfere with Attraction of Common Green Lacewings to Floral Bait. Journal of chemical ecology. 2015 Jun; 41(6):550-6. doi: 10.1007/s10886-015-0585-7. [PMID: 25956798]
  • Danijela Mišić, Branislav Siler, Uroš Gašić, Stevan Avramov, Suzana Zivković, Jasmina Nestorović Živković, Milica Milutinović, Zivoslav Tešić. Simultaneous UHPLC/DAD/(+/-)HESI-MS/MS analysis of phenolic acids and nepetalactones in methanol extracts of Nepeta species: a possible application in chemotaxonomic studies. Phytochemical analysis : PCA. 2015 Jan; 26(1):72-85. doi: 10.1002/pca.2538. [PMID: 25431035]
  • G Gkinis, A Michaelakis, G Koliopoulos, E Ioannou, O Tzakou, V Roussis. Evaluation of the repellent effects of Nepeta parnassica extract, essential oil, and its major nepetalactone metabolite against mosquitoes. Parasitology research. 2014 Mar; 113(3):1127-34. doi: 10.1007/s00436-013-3750-3. [PMID: 24449446]
  • Güzin Kekeç, Salih Mutlu, Lokman Alpsoy, M Serdal Sakçali, Ökkes Atici. Genotoxic effects of catmint (Nepeta meyeri Benth.) essential oils on some weed and crop plants. Toxicology and industrial health. 2013 Jul; 29(6):504-13. doi: 10.1177/0748233712440135. [PMID: 22434692]
  • J J Zhu, D R Berkebile, C A Dunlap, A Zhang, D Boxler, K Tangtrakulwanich, R W Behle, F Baxendale, G Brewer. Nepetalactones from essential oil of Nepeta cataria represent a stable fly feeding and oviposition repellent. Medical and veterinary entomology. 2012 Jun; 26(2):131-8. doi: 10.1111/j.1365-2915.2011.00972.x. [PMID: 21781140]
  • Adrian Martin Pohlit, Norberto Peporine Lopes, Renata Antonaci Gama, Wanderli Pedro Tadei, Valter Ferreira de Andrade Neto. Patent literature on mosquito repellent inventions which contain plant essential oils--a review. Planta medica. 2011 Apr; 77(6):598-617. doi: 10.1055/s-0030-1270723. [PMID: 21328177]
  • Michael A Birkett, Ahmed Hassanali, Solveig Hoglund, Jan Pettersson, John A Pickett. Repellent activity of catmint, Nepeta cataria, and iridoid nepetalactone isomers against Afro-tropical mosquitoes, ixodid ticks and red poultry mites. Phytochemistry. 2011 Jan; 72(1):109-14. doi: 10.1016/j.phytochem.2010.09.016. [PMID: 21056438]
  • Abier Sofrata, Ellen M Santangelo, Muhammad Azeem, Anna-Karin Borg-Karlson, Anders Gustafsson, Katrin Pütsep. Benzyl isothiocyanate, a major component from the roots of Salvadora persica is highly active against Gram-negative bacteria. PloS one. 2011; 6(8):e23045. doi: 10.1371/journal.pone.0023045. [PMID: 21829688]
  • Sándor Koczor, Ferenc Szentkirályi, Michael A Birkett, John A Pickett, Erzsébet Voigt, Miklós Tóth. Attraction of Chrysoperla carnea complex and Chrysopa spp. lacewings (Neuroptera: Chrysopidae) to aphid sex pheromone components and a synthetic blend of floral compounds in Hungary. Pest management science. 2010 Dec; 66(12):1374-9. doi: 10.1002/ps.2030. [PMID: 20949547]
  • George Gkinis, Biljana Bozin, Neda Mimica-Dukic, Olga Tzakou. Antioxidant activity of Nepeta nuda L. ssp. nuda essential oil rich in nepetalactones from Greece. Journal of medicinal food. 2010 Oct; 13(5):1176-81. doi: 10.1089/jmf.2009.0218. [PMID: 20626246]
  • Jasmina Nestorović, Danijela Misić, Branislav Siler, Marina Soković, Jasmina Glamoclija, Ana Cirić, Vuk Maksimović, Dragoljub Grubisić. Nepetalactone content in shoot cultures of three endemic Nepeta species and the evaluation of their antimicrobial activity. Fitoterapia. 2010 Sep; 81(6):621-6. doi: 10.1016/j.fitote.2010.03.007. [PMID: 20307630]
  • Ali Shafaghat, Khodamali Oji. Nepetalactone content and antibacterial activity of the essential oils from different parts of Nepeta persica. Natural product communications. 2010 Apr; 5(4):625-8. doi: . [PMID: 20433086]
  • Ahmet Adiguzel, Hakan Ozer, Munevver Sokmen, Medine Gulluce, Atalay Sokmen, Hamdullah Kilic, Fikrettin Sahin, Ozlem Baris. Antimicrobial and antioxidant activity of the essential oil and methanol extract of Nepeta cataria. Polish journal of microbiology. 2009; 58(1):69-76. doi: . [PMID: 19469289]
  • Marie Pettersson, C Rikard Unelius, Irena Valterová, Anna-Karin Borg-Karlson. Semiochemicals related to the aphid Cinara pilicornis and its host, Picea abies: a method to assign nepetalactone diastereomers. Journal of chromatography. A. 2008 Feb; 1180(1-2):165-70. doi: 10.1016/j.chroma.2007.12.020. [PMID: 18166192]
  • Cheryl Lans, Nancy Turner, Tonya Khan, Gerhard Brauer, Willi Boepple. Ethnoveterinary medicines used for ruminants in British Columbia, Canada. Journal of ethnobiology and ethnomedicine. 2007 Feb; 3(?):11. doi: 10.1186/1746-4269-3-11. [PMID: 17324258]
  • Kamlesh R Chauhan, Jerome A Klun, Mustapha Debboun, Matthew Kramer. Feeding deterrent effects of catnip oil components compared with two synthetic amides against Aedes aegypti. Journal of medical entomology. 2005 Jul; 42(4):643-6. doi: 10.1603/0022-2585(2005)042[0643:fdeoco]2.0.co;2. [PMID: 16119554]
  • Qing-He Zhang, Kamlesh R Chauhan, Eric F Erbe, Ajay R Vellore, Jeffrey R Aldrich. Semiochemistry of the goldeneyed lacewing Chrysopa oculata: attraction of males to a male-produced pheromone. Journal of chemical ecology. 2004 Sep; 30(9):1849-70. doi: 10.1023/b:joec.0000042406.76705.ab. [PMID: 15586679]
  • Kye Chung Park, Jim Hardie. Electrophysiological characterisation of olfactory sensilla in the black bean aphid, Aphis fabae. Journal of insect physiology. 2004 Jul; 50(7):647-55. doi: 10.1016/j.jinsphys.2004.04.011. [PMID: 15234625]
  • Giorgos Gkinis, Olga Tzakou, Dimitra Iliopoulou, Vassilios Roussis. Chemical composition and biological activity of Nepeta parnassica oils and isolated nepetalactones. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Sep; 58(9-10):681-6. doi: 10.1515/znc-2003-9-1015. [PMID: 14577631]
  • A M Hooper, B Donato, C M Woodcock, J H Park, R L Paul, K S Boo, J Hardie, J A Pickett. Characterization of (1'R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis. Journal of chemical ecology. 2002 Apr; 28(4):849-64. doi: 10.1023/a:1015201129331. [PMID: 12035931]
  • E Kalpoutzakis, N Aligiannis, A Mentis, S Mitaku, C Charvala. Composition of the essential oil of two Nepeta species and in vitro evaluation of their activity against Helicobacter pylori. Planta medica. 2001 Dec; 67(9):880-3. doi: 10.1055/s-2001-18851. [PMID: 11745033]
  • M Ganzera, S Crockett, M R Tellez, I A Khan. Determination of nepetalactone in Nepeta cataria by reversed phase high performance liquid chromatography. Die Pharmazie. 2001 Nov; 56(11):896-7. doi: ". [PMID: 11817179]
  • S Aydin, R Beis, Y Oztürk, K H Baser, C Baser. Nepetalactone: a new opioid analgesic from Nepeta caesarea Boiss. The Journal of pharmacy and pharmacology. 1998 Jul; 50(7):813-7. doi: 10.1111/j.2042-7158.1998.tb07145.x. [PMID: 9720633]