Dillapiol (BioDeep_00001874114)

Main id: BioDeep_00000008096

 

natural product


代谢物信息卡片


Dillapiole

化学式: C12H14O4 (222.0892)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=CCc1cc2c(c(c1OC)OC)OCO2
InChI: InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3

描述信息

A natural product found in Anethum graveolens.

同义名列表

3 个代谢物同义名

Dillapiole; Dillapiol; Dillapiole



数据库引用编号

14 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)

105 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
Cytoplasm 8 ANG, CASP3, CYP1A1, CYP2A6, CYP3A4, MSMP, NT5C1A, POLB
Peripheral membrane protein 2 ACHE, CYP1A1
Endosome membrane 1 ADRB2
Endoplasmic reticulum membrane 4 CYP1A1, CYP2A6, CYP3A4, HMGCR
Nucleus 6 ACHE, ADRB2, ANG, CASP3, POLB, PPARA
cytosol 3 ANG, CASP3, NT5C1A
nucleoplasm 3 CASP3, POLB, PPARA
Cell membrane 2 ACHE, ADRB2
Multi-pass membrane protein 3 ADRB2, HMGCR, KCNA3
Synapse 1 ACHE
cell surface 1 ACHE
glutamatergic synapse 2 CASP3, KCNA3
Golgi apparatus 2 ACHE, ADRB2
Golgi membrane 1 INS
growth cone 1 ANG
lysosomal membrane 1 GAA
mitochondrial inner membrane 1 CYP1A1
neuromuscular junction 1 ACHE
neuronal cell body 2 ANG, CASP3
presynaptic membrane 1 KCNA3
Lysosome 2 ADRB2, GAA
endosome 1 ADRB2
plasma membrane 6 ACHE, ADRB2, BCHE, EDNRA, GAA, KCNA3
Membrane 7 ACHE, ADRB2, CYP2A6, CYP3A4, GAA, HMGCR, KCNA3
apical plasma membrane 1 ADRB2
axon 1 KCNA3
extracellular exosome 1 GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 1 HMGCR
extracellular space 6 ACHE, ANG, BCHE, IL6, INS, MSMP
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 ACHE, KCNA3
mitochondrion 1 CYP1A1
protein-containing complex 1 POLB
intracellular membrane-bounded organelle 4 CYP1A1, CYP2A6, CYP3A4, GAA
Microsome membrane 2 CYP1A1, CYP3A4
postsynaptic density 1 CASP3
Secreted 7 ACHE, ANG, BCHE, GAA, IL6, INS, MSMP
extracellular region 6 ACHE, ANG, BCHE, GAA, IL6, INS
Extracellular side 1 ACHE
actin cytoskeleton 1 ANG
nucleolus 1 ANG
Early endosome 1 ADRB2
postsynaptic membrane 1 KCNA3
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 1 KCNA3
microtubule 1 POLB
basement membrane 2 ACHE, ANG
peroxisomal membrane 1 HMGCR
receptor complex 1 ADRB2
chromatin 1 PPARA
Chromosome 1 ANG
Nucleus, nucleolus 1 ANG
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 2]: Cell membrane 1 KCNA3
endosome lumen 1 INS
tertiary granule membrane 1 GAA
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
side of membrane 1 ACHE
Peroxisome membrane 1 HMGCR
voltage-gated potassium channel complex 1 KCNA3
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 BCHE, IL6, INS
endocytic vesicle 1 ANG
transport vesicle 1 INS
azurophil granule membrane 1 GAA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
neuronal dense core vesicle 1 ADRB2
nuclear envelope lumen 1 BCHE
calyx of Held 1 KCNA3
clathrin-coated endocytic vesicle membrane 1 ADRB2
cytoplasmic microtubule 1 CYP2A6
synaptic cleft 1 ACHE
ficolin-1-rich granule membrane 1 GAA
spindle microtubule 1 POLB
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 KCNA3
hemoglobin complex 1 HBM
haptoglobin-hemoglobin complex 1 HBM
angiogenin-PRI complex 1 ANG
interleukin-6 receptor complex 1 IL6
autolysosome lumen 1 GAA
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
[Isoform H]: Cell membrane 1 ACHE


文献列表

  • Amner Muñoz-Acevedo, María C González, Jesús E Alonso, Karen C Flórez. The Repellent Capacity against Sitophilus zeamais (Coleoptera: Curculionidae) and In Vitro Inhibition of the Acetylcholinesterase Enzyme of 11 Essential Oils from Six Plants of the Caribbean Region of Colombia. Molecules (Basel, Switzerland). 2024 Apr; 29(8):. doi: 10.3390/molecules29081753. [PMID: 38675573]
  • Inès Jallali, Hédia Hannachi, Yosr Zaouali, Abderrazek Smaoui, Chedly Abdelly, Riadh Ksouri. Crithmum maritimum L. Volatile Compound's Diversity Through Tunisian Populations: Use of a Plant Organ-Based Statistical Approach for Chemotype Identification. Chemistry & biodiversity. 2023 Oct; ?(?):e202300827. doi: 10.1002/cbdv.202300827. [PMID: 37884443]
  • Takao Koeduka, Bunta Watanabe, Konomi Shirahama, Masaru Nakayasu, Shiro Suzuki, Takumi Furuta, Hideyuki Suzuki, Kenji Matsui, Tomoyuki Kosaka, Shin-Ichi Ozaki. Biosynthesis of dillapiole/apiole in dill (Anethum graveolens): characterization of regioselective phenylpropene O-methyltransferase. The Plant journal : for cell and molecular biology. 2023 02; 113(3):562-575. doi: 10.1111/tpj.16068. [PMID: 36534115]
  • Daniel Luís Viana Cruz, Tania Cristina Sumita, Mayla Silva Leão Ferreira, Junielson Soares da Silva, Ana Cristina da Silva Pinto, José Fernando Marques Barcellos, Míriam Silva Rafael. Histopathological, cytotoxicological, and genotoxic effects of the semi-synthetic compound dillapiole n-butyl ether in Balb/C mice. Journal of toxicology and environmental health. Part A. 2020 09; 83(17-18):604-615. doi: 10.1080/15287394.2020.1804026. [PMID: 32787530]
  • Lina Cristina Salazar, Adriana Ortiz-Reyes, Diana Marcela Rosero, Tatiana Lobo-Echeverri. Dillapiole in Piper holtonii as an Inhibitor of the Symbiotic Fungus Leucoagaricus gongylophorus of Leaf-Cutting Ants. Journal of chemical ecology. 2020 Aug; 46(8):668-674. doi: 10.1007/s10886-020-01170-w. [PMID: 32173778]
  • Carla Guijarro-Real, Adrián Rodríguez-Burruezo, Jaime Prohens, María D Raigón, Ana Fita. HS-SPME analysis of the volatiles profile of water celery (Apium nodiflorum), a wild vegetable with increasing culinary interest. Food research international (Ottawa, Ont.). 2019 07; 121(?):765-775. doi: 10.1016/j.foodres.2018.12.054. [PMID: 31108807]
  • Alexander V Samet, Oksana G Shevchenko, Vyacheslav V Rusak, Eduard M Chartov, Andrey B Myshlyavtsev, Daniil A Rusanov, Marina N Semenova, Victor V Semenov. Antioxidant Activity of Natural Allylpolyalkoxybenzene Plant Essential Oil Constituents. Journal of natural products. 2019 Jun; ?(?):. doi: 10.1021/acs.jnatprod.8b00878. [PMID: 31244145]
  • V S Lima, A C Pinto, M S Rafael. Effect of isodillapiole on the expression of the insecticide resistance genes GSTE7 and CYP6N12 in Aedes aegypti from central Amazonia. Genetics and molecular research : GMR. 2015 Dec; 14(4):16728-35. doi: 10.4238/2015.december.11.20. [PMID: 26681019]
  • Anderson M Gaia, Lydia F Yamaguchi, Christopher S Jeffrey, Massuo J Kato. Age-dependent changes from allylphenol to prenylated benzoic acid production in Piper gaudichaudianum Kunth. Phytochemistry. 2014 Oct; 106(?):86-93. doi: 10.1016/j.phytochem.2014.06.013. [PMID: 25041698]
  • Eliezer H Pires Aciole, Nilza N Guimarães, Andre S Silva, Erima M Amorim, Sergio M Nunomura, Ana Cristina L Garcia, Kênya S Cunha, Claudia Rohde. Genetic toxicity of dillapiol and spinosad larvicides in somatic cells of Drosophila melanogaster. Pest management science. 2014 Apr; 70(4):559-65. doi: 10.1002/ps.3573. [PMID: 23650150]
  • Adilson Kleber Ferreira, Paulo Luiz de-Sá-Júnior, Kerly Fernanda Mesquita Pasqualoto, Ricardo Alexandre de Azevedo, Diana Aparecida Dias Câmara, André Santos Costa, Carlos Rogério Figueiredo, Alisson Leonardo Matsuo, Mariana Hiromi Massaoka, Aline Vivian Vatti Auada, Ivo Lebrun, Mariana Celestina Frojuello Costa Bernstorff Damião, Maurício Temotheo Tavares, Fátima Maria Motter Magri, Irina Kerkis, Roberto Parise Filho. Cytotoxic effects of dillapiole on MDA-MB-231 cells involve the induction of apoptosis through the mitochondrial pathway by inducing an oxidative stress while altering the cytoskeleton network. Biochimie. 2014 Apr; 99(?):195-207. doi: 10.1016/j.biochi.2013.12.008. [PMID: 24355203]
  • Raúl Rojas-Martínez, Jesús Arrieta, Leticia Cruz-Antonio, Daniel Arrieta-Baez, Antonio Magdiel Velázquez-Méndez, María Elena Sánchez-Mendoza. Dillapiole, isolated from Peperomia pellucida, shows gastroprotector activity against ethanol-induced gastric lesions in Wistar rats. Molecules (Basel, Switzerland). 2013 Sep; 18(9):11327-37. doi: 10.3390/molecules180911327. [PMID: 24064453]
  • Roberto Parise-Filho, Kerly Fernanda Mesquita Pasqualoto, Fátima Maria Motter Magri, Adilson Kleber Ferreira, Bárbara Athayde Vaz Galvão da Silva, Mariana Celestina Frojuello Costa Bernstorff Damião, Maurício Temotheo Tavares, Ricardo Alexandre Azevedo, Aline Vivian Vatti Auada, Michelle Carneiro Polli, Carlos Alberto Brandt. Dillapiole as antileishmanial agent: discovery, cytotoxic activity and preliminary SAR studies of dillapiole analogues. Archiv der Pharmazie. 2012 Dec; 345(12):934-44. doi: 10.1002/ardp.201200212. [PMID: 22996811]
  • Tanya Joffe, Robin V Gunning, Geoff R Allen, Michael Kristensen, Selcan Alptekin, Linda M Field, Graham D Moores. Investigating the potential of selected natural compounds to increase the potency of pyrethrum against houseflies Musca domestica (Diptera: Muscidae). Pest management science. 2012 Feb; 68(2):178-84. doi: 10.1002/ps.2241. [PMID: 21770012]
  • Roberto Parise-Filho, Michelli Pastrello, Carla Emygdio Pereira Camerlingo, Gisele Juni Silva, Leonardo Aguiar Agostinho, Thaís de Souza, Fátima Maria Motter Magri, Roberto Rodrigues Ribeiro, Carlos Alberto Brandt, Michelle Carneiro Polli. The anti-inflammatory activity of dillapiole and some semisynthetic analogues. Pharmaceutical biology. 2011 Nov; 49(11):1173-9. doi: 10.3109/13880209.2011.575793. [PMID: 22014265]
  • Nacim Zouari, Nahed Fakhfakh, Sami Zouari, Mohamed Sellami, Mouna Abid, M A Ayadi, Slah Zaidi, Mohamed Neffati. Volatile and lipid analyses by gas chromatography/mass spectrometry and nutraceutical potential of edible wild Malva aegyptiaca L. (Malvaceae). International journal of food sciences and nutrition. 2011 Sep; 62(6):600-8. doi: 10.3109/09637486.2011.564157. [PMID: 21534888]
  • Victor V Semenov, Alex S Kiselyov, Ilia Y Titov, Irina K Sagamanova, Natalie N Ikizalp, Natalia B Chernysheva, Dmitry V Tsyganov, Leonid D Konyushkin, Sergei I Firgang, Roman V Semenov, Irina B Karmanova, Mikhail M Raihstat, Marina N Semenova. Synthesis of antimitotic polyalkoxyphenyl derivatives of combretastatin using plant allylpolyalkoxybenzenes. Journal of natural products. 2010 Nov; 73(11):1796-802. doi: 10.1021/np1004278. [PMID: 21049975]
  • S Jana, G S Shekhawat. Anethum graveolens: An Indian traditional medicinal herb and spice. Pharmacognosy reviews. 2010 Jul; 4(8):179-84. doi: 10.4103/0973-7847.70915. [PMID: 22228959]
  • Aymen Jabrane, Hichem Ben Jannet, Maha Mastouri, Zine Mighri, Joseph Casanova. Chemical composition and in vitro evaluation of antioxidant and antibacterial activities of the root oil of Ridolfia segetum (L.) Moris from Tunisia. Natural product research. 2010 Apr; 24(6):491-9. doi: 10.1080/14786410802228520. [PMID: 20397101]
  • Inder Pal Singh Kapoor, Bandana Singh, Gurdip Singh, Carola S De Heluani, Marina P De Lampasona, Cesar A N Catalan. Chemistry and antioxidant activity of essential oil and oleoresins of black caraway (Carum bulbocastanum) fruits: Part 69. Journal of the science of food and agriculture. 2010 Feb; 90(3):385-90. doi: 10.1002/jsfa.3824. [PMID: 20355057]
  • Wilson Castro Silva, João Ricardo de Souza Martins, Hellen Emília Menezes de Souza, Horacio Heinzen, Maria Verônica Cesio, Mauricio Mato, Francine Albrecht, João Lúcio de Azevedo, Neiva Monteiro de Barros. Toxicity of Piper aduncum L. (Piperales: Piperaceae) from the Amazon forest for the cattle tick Rhipicephalus (Boophilus) microplus (Acari: Ixodidae). Veterinary parasitology. 2009 Oct; 164(2-4):267-74. doi: 10.1016/j.vetpar.2009.06.006. [PMID: 19573994]
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  • B Marongiu, A Maxia, A Piras, S Porcedda, E Tuveri, M J Gonçalves, C Cavaleiro, L Salgueiro. Isolation of Crithmum maritimum L. volatile oil by supercritical carbon dioxide extraction and biological assays. Natural product research. 2007 Nov; 21(13):1145-50. doi: 10.1080/14786410600911616. [PMID: 17987493]
  • Jason W Budzinski, Vance L Trudeau, Cathy E Drouin, Mitra Panahi, J Thor Arnason, Brian C Foster. Modulation of human cytochrome P450 3A4 (CYP3A4) and P-glycoprotein (P-gp) in Caco-2 cell monolayers by selected commercial-source milk thistle and goldenseal products. Canadian journal of physiology and pharmacology. 2007 Sep; 85(9):966-78. doi: 10.1139/y07-091. [PMID: 18066144]
  • Virginie Treyvaud Amiguet, Philippe Petit, Chieu Anh Ta, Ronaldo Nuñez, Pablo Sánchez-Vindas, Luis Poveda Alvarez, Myron L Smith, John Thor Arnason, Tony Durst. Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense. Journal of natural products. 2006 Jul; 69(7):1005-9. doi: 10.1021/np0504863. [PMID: 16872133]
  • Gurdip Singh, Palanisamy Marimuthu, Carola S de Heluani, Cesar A N Catalan. Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components. Journal of agricultural and food chemistry. 2006 Jan; 54(1):174-81. doi: 10.1021/jf0518610. [PMID: 16390196]
  • Claus M Passreiter, Yasmin Akhtar, Murray B Isman. Insecticidal activity of the essential oil of Ligusticum mutellina roots. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2005 May; 60(5-6):411-4. doi: 10.1515/znc-2005-5-608. [PMID: 16042341]
  • Suresh Walia, Supradeep Saha, Balraj S Parmar. Liquid chromatographic method for the analysis of two plant based insecticide synergists dillapiole and dihydrodillapiole. Journal of chromatography. A. 2004 Aug; 1047(2):229-33. doi: 10.1016/j.chroma.2004.07.009. [PMID: 15460253]
  • V S Prakash Chaturvedula, Sidney M Hecht, Zhijie Gao, Shannon H Jones, Xizhi Feng, David G I Kingston. New neolignans that inhibit DNA polymerase beta lyase. Journal of natural products. 2004 Jun; 67(6):964-7. doi: 10.1021/np030507y. [PMID: 15217274]