Menthofuran (BioDeep_00000015317)

Main id: BioDeep_00000001067

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(+)-Menthofuran

化学式: C10H14O (150.1045)
中文名称: (+)-薄荷呋喃, 薄荷呋喃
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C12C[C@@H](CCC=1C(=CO2)C)C
InChI: InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3

描述信息

A menthofuran that is 4,5,6,7-tetrahydro-1-benzofuran substituted by methyl groups at positions 3 and 6 (the 6R-enantiomer).
(r)-menthofuran, also known as 4,5,6,7-tetrahydro-3,6-dimethylbenzofuran or 3,9-epoxy-P-mentha-3,8-diene, is a member of the class of compounds known as aromatic monoterpenoids. Aromatic monoterpenoids are monoterpenoids containing at least one aromatic ring (r)-menthofuran is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (r)-menthofuran is a coffee, earthy, and musty tasting compound found in herbs and spices, mentha (mint), and orange mint, which makes (r)-menthofuran a potential biomarker for the consumption of these food products (r)-menthofuran can be found primarily in saliva.

同义名列表

5 个代谢物同义名

(+)-Menthofuran; Menthofuran; UNII:LK024V9U3C; Menthofuran; Menthofuran



数据库引用编号

16 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

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

70 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


文献列表

  • 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]
  • 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]
  • Niko Radulović, Milan Dekić, Milan Joksović, Rastko Vukićević. Chemotaxonomy of Serbian Teucrium species inferred from essential oil chemical composition: the case of Teucrium scordium L. ssp. scordioides. Chemistry & biodiversity. 2012 Jan; 9(1):106-22. doi: 10.1002/cbdv.201100204. [PMID: 22253108]
  • Sylvain Sutour, Félix Tomi, Pascale Bradesi, Joseph Casanova. Chemical composition of the essential oil from Corsican Mentha aquatica--combined analysis by GC(RI), GC-MS and 13C NMR spectroscopy. Natural product communications. 2011 Oct; 6(10):1479-82. doi: . [PMID: 22164788]
  • 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]
  • Simon Atsbaha Zebelo, Cinzia M Bertea, Simone Bossi, Andrea Occhipinti, Giorgio Gnavi, Massimo E Maffei. Chrysolina herbacea modulates terpenoid biosynthesis of Mentha aquatica L. PloS one. 2011 Mar; 6(3):e17195. doi: 10.1371/journal.pone.0017195. [PMID: 21408066]
  • 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]
  • S Cyrus Khojasteh, Shimako Oishi, Sidney D Nelson. Metabolism and toxicity of menthofuran in rat liver slices and in rats. Chemical research in toxicology. 2010 Nov; 23(11):1824-32. doi: 10.1021/tx100268g. [PMID: 20945912]
  • Mohamed A Ibrahim, Maarit Mäenpää, Viivi Hassinen, Sari Kontunen-Soppela, Lukás Malec, Matti Rousi, Liisa Pietikäinen, Arja Tervahauta, Sirpa Kärenlampi, Jarmo K Holopainen, Elina J Oksanen. Elevation of night-time temperature increases terpenoid emissions from Betula pendula and Populus tremula. Journal of experimental botany. 2010 Jun; 61(6):1583-95. doi: 10.1093/jxb/erq034. [PMID: 20181662]
  • Marios A Menelaou, Hidelisa P Henandez, Francisco A Macías, Jeffrey D Weidenhamer, G Bruce Williamson, Frank R Fronczek, Helga D Fischer, Nikolaus H Fischer. Constituents of Calamintha ashei: effects on Florida sandhill species. Natural product communications. 2010 May; 5(5):685-94. doi: . [PMID: 20521531]
  • Rigoberto Rios-Estepa, Iris Lange, James M Lee, B Markus Lange. Mathematical modeling-guided evaluation of biochemical, developmental, environmental, and genotypic determinants of essential oil composition and yield in peppermint leaves. Plant physiology. 2010 Apr; 152(4):2105-19. doi: 10.1104/pp.109.152256. [PMID: 20147490]
  • Luiz C A Barbosa, Célia R A Maltha, Raphael C Cusati, Róbson R Teixeira, Filipe F Rodrigues, Antônio A Silva, Michael G B Drew, Fyaz M D Ismail. Synthesis and biological evaluation of new ozonides with improved plant growth regulatory activity. Journal of agricultural and food chemistry. 2009 Nov; 57(21):10107-15. doi: 10.1021/jf902540z. [PMID: 19886678]
  • Bharti Sapra, Subheet Jain, A K Tiwary. Percutaneous permeation enhancement by terpenes: mechanistic view. The AAPS journal. 2008; 10(1):120-32. doi: 10.1208/s12248-008-9012-0. [PMID: 18446512]
  • Marco Mucciarelli, Wanda Camusso, Massimo Maffei, Paola Panicco, Carlo Bicchi. Volatile terpenoids of endophyte-free and infected peppermint (Mentha piperita L.): chemical partitioning of a symbiosis. Microbial ecology. 2007 Nov; 54(4):685-96. doi: 10.1007/s00248-007-9227-0. [PMID: 17370029]
  • 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]
  • Jonathan R Latham, Allison K Wilson, Ricarda A Steinbrecher. The mutational consequences of plant transformation. Journal of biomedicine & biotechnology. 2006; 2006(2):25376. doi: 10.1155/jbb/2006/25376. [PMID: 16883050]
  • P Racine, B Auffray. Quenching of singlet molecular oxygen by Commiphora myrrha extracts and menthofuran. Fitoterapia. 2005 Jun; 76(3-4):316-23. doi: 10.1016/j.fitote.2005.03.017. [PMID: 15890469]
  • 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]
  • L-J Chen, E H Lebetkin, L T Burka. Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. Drug metabolism and disposition: the biological fate of chemicals. 2003 Oct; 31(10):1208-13. doi: 10.1124/dmd.31.10.1208. [PMID: 12975329]
  • 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]
  • 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]
  • . . . . doi: . [PMID: 15542490]