Cuminaldehyde (BioDeep_00000001118)

 

Secondary id: BioDeep_00000860125

human metabolite PANOMIX_OTCML-2023 Endogenous Antitumor activity Cytotoxicity Volatile Flavor Compounds natural product


代谢物信息卡片


4-(1-Methylethyl)benzaldehyde

化学式: C10H12O (148.08881019999998)
中文名称: 4-异丙基苯甲醛, 枯名醛
谱图信息: 最多检出来源 Homo sapiens(blood) 0.1%

Reviewed

Last reviewed on 2024-07-11.

Cite this Page

Cuminaldehyde. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/cuminaldehyde (retrieved 2024-11-21) (BioDeep RN: BioDeep_00000001118). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c1cc(ccc1C=O)C(C)C
InChI: InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3

描述信息

Cuminaldehyde is the biologically active constituent of Cuminum cyminum seed oil. C. cyminum seed-derived materials have an inhibitory effect in vitro against rat lens aldose reductase and alpha-glucosidase. This inhibitory action cuminaldehyde suggest a potential utility as an antidiabetic therapeutic. (PMID:15796577). Cuminaldehyde is a volatile compound representative of cumin aroma present in trace amounts in the blood and milk of ewes fed with cumin seed. (PMID:8738023). The terpenoid cuminaldehyde, undergoes reduction biotransformation in mammals, but not oxidation. (PMID:2815827).
Cuminaldehyde is a member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities. It has a role as an insecticide, a volatile oil component and a plant metabolite. It derives from a hydride of a cumene.
4-Isopropylbenzaldehyde is a natural product found in Xylopia aromatica, Xylopia sericea, and other organisms with data available.
See also: Paeonia lactiflora root (part of).
A member of the class of benzaldehydes that is benzaldehyde substituted by an isopropyl group at position 4. It is a component of essential oils from Cumin and exhibits insecticidal activities.
Found in many essential oils, including eucalyptus, cumin and cassiaand is also present in grilled or roast beef and cognac. Flavouring agent

Cuminaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=122-03-2 (retrieved 2024-07-11) (CAS RN: 122-03-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Cuminaldehyde is the major component of Cuminum cyminum, a natural aldehyde with inhibitory effect on alpha-synuclein fibrillation and cytotoxicity. Cuminaldehyde shows anticancer activity[1].
Cuminaldehyde is the major component of Cuminum cyminum, a natural aldehyde with inhibitory effect on alpha-synuclein fibrillation and cytotoxicity. Cuminaldehyde shows anticancer activity[1].

同义名列表

52 个代谢物同义名

InChI=1/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H; 4-07-00-00723 (Beilstein Handbook Reference); Cuminal P-(1-methylethyl)benzaldehyde; Cuminal p-(1-methylethyl)benzaldehyde; Cuminaldehyde, analytical standard; p-Isopropylbenzenecarboxaldehyde; Benzaldehyde, 4-(1-methylethyl)-; 4-Isopropylphenylcarboxaldehyde; (4-isopropyl-phenyl)-methanone; Cuminaldehyde, >=98\\%, FCC, FG; 4-Isopropylbenzenecarboxylate; p-(1-methylethyl)benzaldehyde; 4-(1-Methylethyl)benzaldehyde; 4-(Propan-2-Yl)Benzaldehyde; 4-(Methylethyl)benzaldehyde; p-Isopropylbenzaldehyde, f; Benzaldehyde, p-isopropyl-; 4-(isopropyl)benzaldehyde; 4-propan-2-ylbenzaldehyde; p-isopropyl benzaldehyde; p-iso-Propylbenzaldehyde; 4(isopropyl)benzaldehyde; 4-Isopropyl-benzaldehyde; p-isopropyl-Benzaldehyde; 4-isopropyl benzaldehyde; 4(2-propyl)-benzaldehyde; 4-isopropylbenzaldehyde; P-ISOPROPYLBENZALDEHYDE; 4isopropylbenzaldehyde; 4-i-propylbenzaldehyde; CUMINIC ALDEHYDE [FCC]; CUMINALDEHYDE [FHFI]; Cuminaldehyde, 98\\%; 4-iPr-Benzaldehyde; CUMINALDEHYDE [MI]; p-Cuminic aldehyde; cuminic aldehyde; Cuminyl aldehyde; p-cumic aldehyde; WLN: VHR DY1 & 1; Cumic aldehyde; Cumin aldehyde; Cuminadlehyde; Cuminaldehyde; Cuminaldehyd; Tox21_300712; cumaldehyde; AI3-01853; cuminal; Cumal; 4-Isopropylbenzaldehyde; 4-Isopropylbenzaldehyde



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(0)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

  • p-cymene degradation: p-cymene + H+ + O2 + a reduced ferredoxin [iron-sulfur] cluster ⟶ 4-isopropylbenzyl alcohol + H2O + an oxidized ferredoxin [iron-sulfur] cluster
  • p-cymene degradation to p-cumate: p-cymene + H+ + O2 + a reduced ferredoxin [iron-sulfur] cluster ⟶ 4-isopropylbenzyl alcohol + H2O + an oxidized ferredoxin [iron-sulfur] cluster
  • p-cymene degradation to p-cumate: p-cymene + H+ + NADH + O2 ⟶ p-cumic alcohol + H2O + NAD+

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

256 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

  • Mohd Nazam Ansari, Najeeb Ur Rehman, Abdul Samad, Wasim Ahmad. Pharmacological Basis for the Antidiarrheal and Antispasmodic Effects of Cuminaldehyde in Experimental Animals: In Silico, Ex Vivo and In Vivo Studies. Frontiers in bioscience (Landmark edition). 2024 Jan; 29(1):43. doi: 10.31083/j.fbl2901043. [PMID: 38287835]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Xiao Zhai, Jieying Liu, Miao Yu, Qian Zhang, Ming Li, Nan Zhao, Juntao Liu, Yingna Song, Liangkun Ma, Rongrong Li, Zongxu Qiao, Guifen Zhao, Ruiping Wang, Xinhua Xiao. Nontargeted metabolomics reveals the potential mechanism underlying the association between birthweight and metabolic disturbances. BMC pregnancy and childbirth. 2023 Jan; 23(1):14. doi: 10.1186/s12884-023-05346-6. [PMID: 36624413]
  • Kannan Duraisamy, Pari Leelavinothan, Paari Ellappan, Tulsi Deepak Singh Balaji, Ponnulakshmi Rajagopal, Selvaraj Jayaraman, Shyamaldevi Babu. Cuminaldehyde ameliorates hyperglycemia in diabetic mice. Frontiers in bioscience (Elite edition). 2022 09; 14(4):24. doi: 10.31083/j.fbe1404024. [PMID: 36575850]
  • Fatemeh Ghiasi, Mohammad Hadi Eskandari, Mohammad Taghi Golmakani, Hadi Hashemi Gahruie, Reza Zarei, Fakhraddin Naghibalhossaini, Seyed Mohammad Hashem Hosseini. A novel promising delivery system for cuminaldehyde using gelled lipid nanoparticles: Characterization and anticancer, antioxidant, and antibacterial activities. International journal of pharmaceutics. 2021 Dec; 610(?):121274. doi: 10.1016/j.ijpharm.2021.121274. [PMID: 34752917]
  • Lin Lin, Xue Liao, Changzhu Li, Mohamed A Abdel-Samie, Subramanian Siva, Haiying Cui. Cold nitrogen plasma modified cuminaldehyde/β-cyclodextrin inclusion complex and its application in vegetable juices preservation. Food research international (Ottawa, Ont.). 2021 03; 141(?):110132. doi: 10.1016/j.foodres.2021.110132. [PMID: 33641999]
  • Vanshita Goel, Lachhman Das Singla, Diptiman Choudhury. Cuminaldehyde induces oxidative stress-mediated physical damage and death of Haemonchus contortus. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Oct; 130(?):110411. doi: 10.1016/j.biopha.2020.110411. [PMID: 32682984]
  • Sheida Koohsari, Mohammad Abbas Sheikholeslami, Siavash Parvardeh, Shiva Ghafghazi, Sanam Samadi, Yalda Khazaei Poul, Ramin Pouriran, Saba Amiri. Antinociceptive and antineuropathic effects of cuminaldehyde, the major constituent of Cuminum cyminum seeds: Possible mechanisms of action. Journal of ethnopharmacology. 2020 Jun; 255(?):112786. doi: 10.1016/j.jep.2020.112786. [PMID: 32222574]
  • J S Rosa, L Oliveira, R M O F Sousa, C B Escobar, M Fernandes-Ferreira. Bioactivity of some Apiaceae essential oils and their constituents against Sitophilus zeamais (Coleoptera: Curculionidae). Bulletin of entomological research. 2020 Jun; 110(3):406-416. doi: 10.1017/s0007485319000774. [PMID: 31813390]
  • Valério Monteiro-Neto, Cláudio D de Souza, Laoane F Gonzaga, Bruna C da Silveira, Nágila C F Sousa, Jaqueline P Pontes, Deivid M Santos, Wanessa C Martins, Jorge F V Pessoa, Alexsander R Carvalho Júnior, Viviane S S Almeida, Natália M T de Oliveira, Thayla S de Araújo, Daniele Maria-Ferreira, Saulo J F Mendes, Thiago A F Ferro, Elizabeth S Fernandes. Cuminaldehyde potentiates the antimicrobial actions of ciprofloxacin against Staphylococcus aureus and Escherichia coli. PloS one. 2020; 15(5):e0232987. doi: 10.1371/journal.pone.0232987. [PMID: 32407399]
  • Amrita Yadav, Anupam Kujur, Akshay Kumar, Prem Pratap Singh, Vishal Gupta, Bhanu Prakash. Encapsulation of Bunium persicum essential oil using chitosan nanopolymer: Preparation, characterization, antifungal assessment, and thermal stability. International journal of biological macromolecules. 2020 Jan; 142(?):172-180. doi: 10.1016/j.ijbiomac.2019.09.089. [PMID: 31521660]
  • Michael Adu-Frimpong, Wei Qiuyu, Caleb Kesse Firempong, Yusif Mohammed Mukhtar, Qiuxuan Yang, Emmanuel Omari-Siaw, Zhen Lijun, Ximing Xu, Jiangnan Yu. Novel cuminaldehyde self-emulsified nanoemulsion for enhanced antihepatotoxicity in carbon tetrachloride-treated mice. The Journal of pharmacy and pharmacology. 2019 Aug; 71(8):1324-1338. doi: 10.1111/jphp.13112. [PMID: 31168820]
  • M R Haque, S H Ansari. Aromatic aldehyde compound cuminaldehyde protects nonalcoholic fatty liver disease in rats feeding high fat diet. Human & experimental toxicology. 2019 Jul; 38(7):823-832. doi: 10.1177/0960327119842248. [PMID: 30974975]
  • Fatemeh Ghiasi, Mohammad Hadi Eskandari, Mohammad-Taghi Golmakani, Seyed Mohammad Hashem Hosseini. Development of highly stable colloidal dispersions of gelled-oil nanoparticles loaded with cuminaldehyde. Journal of colloid and interface science. 2019 Apr; 541(?):65-74. doi: 10.1016/j.jcis.2019.01.010. [PMID: 30682594]
  • Mohammad Rafiul Haque, H Shahid Ansari. Anti-Obesity Effect of Arq Zeera and Its Main Components Thymol and Cuminaldehyde in High Fat Diet Induced Obese Rats. Drug research. 2018 Nov; 68(11):637-647. doi: 10.1055/a-0590-1956. [PMID: 29635674]
  • Atefeh Farvardin, Asa Ebrahimi, Batul Hosseinpour, Mahmood Khosrowshahli. Effects of growth regulators on callus induction and secondary metabolite production in Cuminum cyminum. Natural product research. 2017 Sep; 31(17):1963-1970. doi: 10.1080/14786419.2016.1272105. [PMID: 28044460]
  • Kuen-Daw Tsai, Yi-Heng Liu, Ta-Wei Chen, Shu-Mei Yang, Ho-Yiu Wong, Jonathan Cherng, Kuo-Shen Chou, Jaw-Ming Cherng. Cuminaldehyde from Cinnamomum verum Induces Cell Death through Targeting Topoisomerase 1 and 2 in Human Colorectal Adenocarcinoma COLO 205 Cells. Nutrients. 2016 May; 8(6):. doi: 10.3390/nu8060318. [PMID: 27231935]
  • Ta-Wei Chen, Kuen-Daw Tsai, Shu-Mei Yang, Ho-Yiu Wong, Yi-Heng Liu, Jonathan Cherng, Kuo-Shen Chou, Yang-Tz Wang, Janise Cuizon, Jaw-Ming Cherng. Discovery of a Novel Anti-Cancer Agent Targeting Both Topoisomerase I & II as Well as Telomerase Activities in Human Lung Adenocarcinoma A549 Cells In Vitro and In Vivo: Cinnamomum verum Component Cuminaldehyde. Current cancer drug targets. 2016; 16(9):796-806. doi: 10.2174/1568009616666160426125526. [PMID: 27113744]
  • Dina Morshedi, Farhang Aliakbari, Amir Tayaranian-Marvian, Afshin Fassihi, Francisco Pan-Montojo, Horacio Pérez-Sánchez. Cuminaldehyde as the Major Component of Cuminum cyminum, a Natural Aldehyde with Inhibitory Effect on Alpha-Synuclein Fibrillation and Cytotoxicity. Journal of food science. 2015 Oct; 80(10):H2336-45. doi: 10.1111/1750-3841.13016. [PMID: 26351865]
  • M J Tomy, K V Dileep, S Prasanth, D S Preethidan, A Sabu, C Sadasivan, M Haridas. Cuminaldehyde as a lipoxygenase inhibitor: in vitro and in silico validation. Applied biochemistry and biotechnology. 2014 Sep; 174(1):388-97. doi: 10.1007/s12010-014-1066-0. [PMID: 25080377]
  • Bahman Nickavar, Abrisham Adeli, Azar Nickavar. Analyses of the essential oil from Bunium persicum fruit and its antioxidant constituents. Journal of oleo science. 2014; 63(7):741-6. doi: 10.5650/jos.ess13168. [PMID: 24919477]
  • Swapnil B Patil, Shreehari S Takalikar, Madhav M Joglekar, Vivek S Haldavnekar, Akalpita U Arvindekar. Insulinotropic and β-cell protective action of cuminaldehyde, cuminol and an inhibitor isolated from Cuminum cyminum in streptozotocin-induced diabetic rats. The British journal of nutrition. 2013 Oct; 110(8):1434-43. doi: 10.1017/s0007114513000627. [PMID: 23507295]
  • H B Sowbhagya. Chemistry, technology, and nutraceutical functions of cumin (Cuminum cyminum L): an overview. Critical reviews in food science and nutrition. 2013; 53(1):1-10. doi: 10.1080/10408398.2010.500223. [PMID: 23035918]
  • Hwa-Jeong Yeom, Jae Soon Kang, Gil-Hah Kim, Il-Kwon Park. Insecticidal and acetylcholine esterase inhibition activity of Apiaceae plant essential oils and their constituents against adults of German cockroach (Blattella germanica). Journal of agricultural and food chemistry. 2012 Jul; 60(29):7194-203. doi: 10.1021/jf302009w. [PMID: 22746406]
  • Iness Bettaieb, Soumaya Bourgou, Jezia Sriti, Kamel Msaada, Ferid Limam, Brahim Marzouk. Essential oils and fatty acids composition of Tunisian and Indian cumin (Cuminum cyminum L.) seeds: a comparative study. Journal of the science of food and agriculture. 2011 Aug; 91(11):2100-7. doi: 10.1002/jsfa.4513. [PMID: 21681765]
  • Yuan-Ping Pang, Jewn Giew Park, Shaohua Wang, Anuradha Vummenthala, Rajesh K Mishra, John E McLaughlin, Rong Di, Jennifer Nielsen Kahn, Nilgun E Tumer, Laszlo Janosi, Jon Davis, Charles B Millard. Small-molecule inhibitor leads of ribosome-inactivating proteins developed using the doorstop approach. PloS one. 2011 Mar; 6(3):e17883. doi: 10.1371/journal.pone.0017883. [PMID: 21455295]
  • Qinqin Chen, Xuefang Hu, Jingming Li, Ping Liu, Yang Yang, Yuanying Ni. Preparative isolation and purification of cuminaldehyde and p-menta-1,4-dien-7-al from the essential oil of Cuminum cyminum L. by high-speed counter-current chromatography. Analytica chimica acta. 2011 Mar; 689(1):149-54. doi: 10.1016/j.aca.2011.01.038. [PMID: 21338771]
  • Jun Tian, Xiaoquan Ban, Hong Zeng, Jingsheng He, Bo Huang, Youwei Wang. Chemical composition and antifungal activity of essential oil from Cicuta virosa L. var. latisecta Celak. International journal of food microbiology. 2011 Feb; 145(2-3):464-70. doi: 10.1016/j.ijfoodmicro.2011.01.023. [PMID: 21320730]
  • Moises Martinez-Velazquez, Gustavo Adolfo Castillo-Herrera, Rodrigo Rosario-Cruz, Jose Miguel Flores-Fernandez, Julisa Lopez-Ramirez, Rodolfo Hernandez-Gutierrez, Eugenia del Carmen Lugo-Cervantes. Acaricidal effect and chemical composition of essential oils extracted from Cuminum cyminum, Pimenta dioica and Ocimum basilicum against the cattle tick Rhipicephalus (Boophilus) microplus (Acari: Ixodidae). Parasitology research. 2011 Feb; 108(2):481-7. doi: 10.1007/s00436-010-2069-6. [PMID: 20865426]
  • Hyung Wook Kwon, Soon-Il Kim, Kyu-Sik Chang, J Marshall Clark, Young-Joon Ahn. Enhanced repellency of binary mixtures of Zanthoxylum armatum seed oil, vanillin, and their aerosols to mosquitoes under laboratory and field conditions. Journal of medical entomology. 2011 Jan; 48(1):61-6. doi: 10.1603/me10042. [PMID: 21337949]
  • Tran Trung Hieu, Soon-Il Kim, Hyung Wook Kwon, Young-Joon Ahn. Enhanced repellency of binary mixtures of Zanthoxylum piperitum pericarp steam distillate or Zanthoxylum armatum seed oil constituents and Calophyllum inophyllum nut oil and their aerosols to Stomoxys calcitrans. Pest management science. 2010 Nov; 66(11):1191-8. doi: 10.1002/ps.1993. [PMID: 20628994]
  • Fariba Sharififar, Narguess Yassa, Valiolah Mozaffarian. Bioactivity of major components from the seeds of Bunium persicum (Boiss.) Fedtch. Pakistan journal of pharmaceutical sciences. 2010 Jul; 23(3):300-4. doi: . [PMID: 20566444]
  • Oramas Suttinun, Rudolf Müller, Ekawan Luepromchai. Cometabolic degradation of trichloroethene by Rhodococcus sp. strain L4 immobilized on plant materials rich in essential oils. Applied and environmental microbiology. 2010 Jul; 76(14):4684-90. doi: 10.1128/aem.03036-09. [PMID: 20472723]
  • R J W Meesters, M Duisken, J Hollender. Cytochrome P450-catalysed arene-epoxidation of the bioactive tea tree oil ingredient p-cymene: indication for the formation of a reactive allergenic intermediate?. Xenobiotica; the fate of foreign compounds in biological systems. 2009 Sep; 39(9):663-71. doi: 10.1080/00498250902989094. [PMID: 19480554]
  • Il-Kwon Park, Junheo N Kim, Yeon-Suk Lee, Sang-Gil Lee, Young-Joon Ahn, Sang-Chul Shin. Toxicity of plant essential oils and their components against Lycoriella ingenua (Diptera: Sciaridae). Journal of economic entomology. 2008 Feb; 101(1):139-44. doi: 10.1603/0022-0493(2008)101[139:topeoa]2.0.co;2. [PMID: 18330128]
  • 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]
  • Chao-Bin Xue, Li Zhang, Wan-Chun Luo, Xian-Ye Xie, Lin Jiang, Ting Xiao. 3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors. Bioorganic & medicinal chemistry. 2007 Mar; 15(5):2006-15. doi: 10.1016/j.bmc.2006.12.038. [PMID: 17258462]
  • I Hierro, A Valero, P Pérez, P González, M M Cabo, M P Montilla, M C Navarro. Action of different monoterpenic compounds against Anisakis simplex s.l. L3 larvae. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2004 Jan; 11(1):77-82. doi: 10.1078/0944-7113-00375. [PMID: 14971725]
  • M Désage, B Schaal, J Soubeyrand, P Orgeur, J L Brazier. Gas chromatographic-mass spectrometric method to characterise the transfer of dietary odorous compounds into plasma and milk. Journal of chromatography. B, Biomedical applications. 1996 Apr; 678(2):205-10. doi: 10.1016/0378-4347(95)00527-7. [PMID: 8738023]
  • . . . . doi: . [PMID: 17192005]