Chamazulen (BioDeep_00000868905)

Main id: BioDeep_00000000655

 

PANOMIX_OTCML-2023


代谢物信息卡片


4-05-00-01736 (Beilstein Handbook Reference)

化学式: C14H16 (184.1252)
中文名称: 母菊薁
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCC1=CC2=C(C=CC2=C(C=C1)C)C
InChI: InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3

描述信息

同义名列表

19 个代谢物同义名

4-05-00-01736 (Beilstein Handbook Reference); AZULENE, 1,4-DIMETHYL-7-ETHYL-; Azulene, 7-ethyl-1,4-dimethyl-; 7-ethyl-1,4-dimethyl-azulene; 7-ethyl-1,4-dimethylazulene; 1,4-Dimethyl-7-ethylazulene; EINECS 208-449-6; LMPR01030031; Chamazulene; Dimethulene; BRN 1306577; Chamazulen; Camazulene; Dimethulen; 529-05-5; BA 2784; C09633; Chamazulene; Chamazulene



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)

17 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 11 BCL2, CASP3, CAT, CYP2C9, CYP2D6, CYP3A4, MME, NOS3, PHB1, PTEN, PTGS2
Peripheral membrane protein 3 CYP1B1, GORASP1, PTGS2
Endoplasmic reticulum membrane 6 BCL2, CYP1B1, CYP2C9, CYP2D6, CYP3A4, PTGS2
Nucleus 6 AMIGO2, BCL2, CASP3, NOS3, PHB1, PTEN
cytosol 6 BCL2, CASP3, CAT, GPT, NOS3, PTEN
dendrite 1 MME
trans-Golgi network 1 MME
nucleoplasm 4 CASP3, NOS3, PHB1, PTEN
Cell membrane 4 AMIGO2, MME, PHB1, TNF
Cytoplasmic side 1 GORASP1
Golgi apparatus membrane 1 GORASP1
Synapse 2 ACAN, MME
cell surface 3 MME, PHB1, TNF
glutamatergic synapse 2 ACAN, CASP3
Golgi apparatus 2 GORASP1, NOS3
Golgi membrane 2 GORASP1, NOS3
mitochondrial inner membrane 1 PHB1
neuronal cell body 3 CASP3, MME, TNF
synaptic vesicle 1 MME
Presynapse 1 MME
plasma membrane 8 AMIGO2, BTC, CYP2C9, MME, NOS3, PHB1, PTEN, TNF
Membrane 9 AMIGO2, BCL2, BTC, CAT, CYP1B1, CYP2D6, CYP3A4, MME, PHB1
apical plasma membrane 1 PTEN
axon 1 MME
brush border 1 MME
caveola 2 NOS3, PTGS2
extracellular exosome 5 ADAMTS3, CAT, GPT, MME, PHB1
endoplasmic reticulum 3 BCL2, CYP2D6, PTGS2
extracellular space 5 ACAN, ADAMTS3, BTC, IL6, TNF
lysosomal lumen 1 ACAN
perinuclear region of cytoplasm 1 NOS3
mitochondrion 5 BCL2, CAT, CYP1B1, CYP2D6, PHB1
protein-containing complex 3 BCL2, CAT, PTGS2
intracellular membrane-bounded organelle 5 CAT, CYP1B1, CYP2C9, CYP2D6, CYP3A4
Microsome membrane 5 CYP1B1, CYP2C9, CYP2D6, CYP3A4, PTGS2
postsynaptic density 2 CASP3, PTEN
Single-pass type I membrane protein 1 AMIGO2
Secreted 2 ADAMTS3, IL6
extracellular region 7 ACAN, ADAMTS3, BTC, CAT, IL6, PTEN, TNF
cytoplasmic side of plasma membrane 1 PTEN
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, CYP2D6
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 1 CAT
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 2 ACAN, ADAMTS3
dendritic spine 1 PTEN
cytoplasmic vesicle 1 MME
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 2 MME, PHB1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 MME, TNF
Mitochondrion inner membrane 1 PHB1
Membrane raft 2 MME, TNF
pore complex 1 BCL2
focal adhesion 2 CAT, MME
GABA-ergic synapse 1 ACAN
cis-Golgi network 1 GORASP1
extracellular matrix 1 ADAMTS3
Peroxisome 1 CAT
basement membrane 1 ACAN
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Cell projection, dendritic spine 1 PTEN
Nucleus, PML body 1 PTEN
PML body 1 PTEN
collagen-containing extracellular matrix 1 ACAN
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, neuron projection 1 PTEN
neuron projection 2 PTEN, PTGS2
cell projection 1 PTEN
phagocytic cup 1 TNF
cytoskeleton 1 NOS3
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
secretory granule membrane 1 MME
Golgi lumen 1 ACAN
endoplasmic reticulum lumen 2 IL6, PTGS2
endocytic vesicle membrane 1 NOS3
Schmidt-Lanterman incisure 1 PTEN
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
perineuronal net 1 ACAN
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
clathrin-coated endocytic vesicle membrane 1 BTC
death-inducing signaling complex 1 CASP3
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
myelin sheath adaxonal region 1 PTEN
neuron projection terminus 1 MME
BAD-BCL-2 complex 1 BCL2
[Isoform alpha]: Secreted 1 PTEN
perisynaptic extracellular matrix 1 ACAN
mitochondrial prohibitin complex 1 PHB1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Ding Ma, Jinlong He, Dapeng He. Chamazulene reverses osteoarthritic inflammation through regulation of matrix metalloproteinases (MMPs) and NF-kβ pathway in in-vitro and in-vivo models. Bioscience, biotechnology, and biochemistry. 2020 Feb; 84(2):402-410. doi: 10.1080/09168451.2019.1682511. [PMID: 31642732]
  • Daniel Luiz Reis Simas, Max Samuel Mérida-Reyes, Manuel Alejandro Muñoz-Wug, Millena Santos Cordeiro, Thais Biondino Sardella Giorno, Edwin Adolfo Taracena, Bessie Evelyn Oliva-Hernández, José Vicente Martínez-Arévalo, Patricia Dias Fernandes, Juan Francisco Pérez-Sabino, Antonio Jorge Ribeiro da Silva. Chemical composition and evaluation of antinociceptive activity of the essential oil of Stevia serrata Cav. from Guatemala. Natural product research. 2019 Feb; 33(4):577-579. doi: 10.1080/14786419.2017.1399376. [PMID: 29130346]
  • Mehdi Sharifi-Rad, Jolanta Nazaruk, Letizia Polito, Maria Flaviana Bezerra Morais-Braga, Janaína Esmeraldo Rocha, Henrique Douglas Melo Coutinho, Bahare Salehi, Giulia Tabanelli, Chiara Montanari, María Del Mar Contreras, Zubaida Yousaf, William N Setzer, Deepa R Verma, Miquel Martorell, Antoni Sureda, Javad Sharifi-Rad. Matricaria genus as a source of antimicrobial agents: From farm to pharmacy and food applications. Microbiological research. 2018 Oct; 215(?):76-88. doi: 10.1016/j.micres.2018.06.010. [PMID: 30172312]
  • Reda M Abdelhameed, Hassan Abdel-Gawad, Mohamed Taha, Bahira Hegazi. Separation of bioactive chamazulene from chamomile extract using metal-organic framework. Journal of pharmaceutical and biomedical analysis. 2017 Nov; 146(?):126-134. doi: 10.1016/j.jpba.2017.08.020. [PMID: 28869815]
  • Evangelos C Michelakis, Epameinondas Evergetis, Sofia D Koulocheri, Serkos A Haroutounian. Exploitation of Artemisia arborescens as a Renewable Source of Chamazulene: Seasonal Variation and Distillation Conditions. Natural product communications. 2016 Oct; 11(10):1513-1516. doi: ". [PMID: 30549610]
  • Wen-Juan Zhang, Chun-Xue You, Kai Yang, Ying Wang, Yang Su, Zhu-Feng Geng, Shu-Shan Du, Cheng-Fang Wang, Zhi-Wei Deng, Yong-Yan Wang. Bioactivity and chemical constituents of the essential oil from Dendranthema indicum (L.) Des Moul. against two stored insects. Journal of oleo science. 2015; 64(5):553-60. doi: 10.5650/jos.ess14231. [PMID: 25843281]
  • Arman Zargaran, Afshin Borhani-Haghighi, Pouya Faridi, Saeid Daneshamouz, Gholamreza Kordafshari, Abdolali Mohagheghzadeh. Potential effect and mechanism of action of topical chamomile (Matricaria chammomila L.) oil on migraine headache: A medical hypothesis. Medical hypotheses. 2014 Nov; 83(5):566-9. doi: 10.1016/j.mehy.2014.08.023. [PMID: 25238714]
  • Luigi Ornano, Alessandro Venditti, Mauro Ballero, Cinzia Sanna, Luana Quassinti, Massimo Bramucci, Giulio Lupidi, Fabrizio Papa, Sauro Vittori, Filippo Maggi, Armanodoriano Bianco. Chemopreventive and antioxidant activity of the chamazulene-rich essential oil obtained from Artemisia arborescens L. growing on the Isle of La Maddalena, Sardinia, Italy. Chemistry & biodiversity. 2013 Aug; 10(8):1464-74. doi: 10.1002/cbdv.201200435. [PMID: 23939794]
  • Hafsia Bouzenna, Lamia Krichen. Pelargonium graveolens L'Her. and Artemisia arborescens L. essential oils: chemical composition, antifungal activity against Rhizoctonia solani and insecticidal activity against Rhysopertha dominica. Natural product research. 2013; 27(9):841-6. doi: 10.1080/14786419.2012.711325. [PMID: 22840199]
  • A Jamalian, M Shams-Ghahfarokhi, K Jaimand, N Pashootan, A Amani, M Razzaghi-Abyaneh. Chemical composition and antifungal activity of Matricaria recutita flower essential oil against medically important dermatophytes and soil-borne pathogens. Journal de mycologie medicale. 2012 Dec; 22(4):308-15. doi: 10.1016/j.mycmed.2012.09.003. [PMID: 23518164]
  • Sandra Irmisch, Sandra T Krause, Grit Kunert, Jonathan Gershenzon, Jörg Degenhardt, Tobias G Köllner. The organ-specific expression of terpene synthase genes contributes to the terpene hydrocarbon composition of chamomile essential oils. BMC plant biology. 2012 Jun; 12(?):84. doi: 10.1186/1471-2229-12-84. [PMID: 22682202]
  • Christine Tschiggerl, Franz Bucar. Guaianolides and volatile compounds in chamomile tea. Plant foods for human nutrition (Dordrecht, Netherlands). 2012 Jun; 67(2):129-35. doi: 10.1007/s11130-012-0277-1. [PMID: 22410959]
  • Maria del Carmen Romero, Adela Valero, Joaquina Martín-Sánchez, María Concepción Navarro-Moll. Activity of Matricaria chamomilla essential oil against anisakiasis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2012 Apr; 19(6):520-3. doi: 10.1016/j.phymed.2012.02.005. [PMID: 22397992]
  • M Militello, L Settanni, A Aleo, C Mammina, G Moschetti, G M Giammanco, M Amparo Blàzquez, A Carrubba. Chemical composition and antibacterial potential of Artemisia arborescens L. essential oil. Current microbiology. 2011 Apr; 62(4):1274-81. doi: 10.1007/s00284-010-9855-3. [PMID: 21188586]
  • Martina Köberl, Henry Müller, Elshahat M Ramadan, Gabriele Berg. Desert farming benefits from microbial potential in arid soils and promotes diversity and plant health. PloS one. 2011; 6(9):e24452. doi: 10.1371/journal.pone.0024452. [PMID: 21912695]
  • Ompal Singh, Zakia Khanam, Neelam Misra, Manoj Kumar Srivastava. Chamomile (Matricaria chamomilla L.): An overview. Pharmacognosy reviews. 2011 Jan; 5(9):82-95. doi: 10.4103/0973-7847.79103. [PMID: 22096322]
  • Alejandra Hernández-Ceruelos, Eduardo Madrigal-Santillán, José Antonio Morales-González, Germán Chamorro-Cevallos, Martha Cassani-Galindo, Eduardo Madrigal-Bujaidar. Antigenotoxic effect of Chamomilla recutita (L.) Rauschert essential oil in mouse spermatogonial cells, and determination of its antioxidant capacity in vitro. International journal of molecular sciences. 2010 Sep; 11(10):3793-802. doi: 10.3390/ijms11103793. [PMID: 21152302]
  • Marziyeh Tolouee, Soheil Alinezhad, Reza Saberi, Ali Eslamifar, Seyed Javad Zad, Kamkar Jaimand, Jaleh Taeb, Mohammad-Bagher Rezaee, Masanobu Kawachi, Masoomeh Shams-Ghahfarokhi, Mehdi Razzaghi-Abyaneh. Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem. International journal of food microbiology. 2010 May; 139(3):127-33. doi: 10.1016/j.ijfoodmicro.2010.03.032. [PMID: 20385420]
  • Juliane Rocha de Sant'anna, Claudinéia Conationi da Silva Franco, Claudia Tiemi Miyamoto, Miriam Machado Cunico, Obdulio Gomes Miguel, Lílian Cristina Côcco, Carlos Itsuo Yamamoto, Cirino Corrêa Junior, Marialba Avezum Alves de Castro-Prado. Genotoxicity of Achillea millefolium essential oil in diploid cells of Aspergillus nidulans. Phytotherapy research : PTR. 2009 Feb; 23(2):231-5. doi: 10.1002/ptr.2596. [PMID: 18803228]
  • Monika Verma, Shashank Kumar Singh, Shashi Bhushan, Harish C Pal, Surinder Kitchlu, Maharaj K Koul, Rajender K Thappa, Ajit K Saxena. Induction of mitochondrial-dependent apoptosis by an essential oil from Tanacetum gracile. Planta medica. 2008 Apr; 74(5):515-20. doi: 10.1055/s-2008-1074503. [PMID: 18401843]
  • Jeong-Dan Cha, Eun-Kyung Jung, Bong-Seop Kil, Kyung-Yeol Lee. Chemical composition and antibacterial activity of essential oil from Artemisia feddei. Journal of microbiology and biotechnology. 2007 Dec; 17(12):2061-5. doi: . [PMID: 18167456]
  • Yasuko Noda, Akitane Mori. Antioxidant activities of uyaku (lindera strychnifolia) leaf extract: a natural extract used in traditional medicine. Journal of clinical biochemistry and nutrition. 2007 Sep; 41(2):139-45. doi: 10.3164/jcbn2007019. [PMID: 18193108]
  • Francesco Lai, Chiara Sinico, Alessandro De Logu, Marco Zaru, Rainer H Müller, Anna M Fadda. SLN as a topical delivery system for Artemisia arborescens essential oil: in vitro antiviral activity and skin permeation study. International journal of nanomedicine. 2007; 2(3):419-25. doi: ". [PMID: 18019840]
  • Mai Ramadan, Bernhard Watzer. Determination of chamazulene carboxylic acid in serum by high-performance liquid chromatography. Development and validation. Journal of chromatography. A. 2006 Nov; 1133(1-2):221-5. doi: 10.1016/j.chroma.2006.08.035. [PMID: 16942774]
  • Diane L McKay, Jeffrey B Blumberg. A review of the bioactivity and potential health benefits of chamomile tea (Matricaria recutita L.). Phytotherapy research : PTR. 2006 Jul; 20(7):519-30. doi: 10.1002/ptr.1900. [PMID: 16628544]
  • Bruno Marongiu, Alessandra Piras, Silvia Porcedda. Comparative analysis of the oil and supercritical CO(2) extract of Artemisia arborescens L. and Helichrysum splendidum (Thunb.) Less. Natural product research. 2006 May; 20(5):421-8. doi: 10.1080/14786410500102977. [PMID: 16644539]
  • M Ganzera, P Schneider, H Stuppner. Inhibitory effects of the essential oil of chamomile (Matricaria recutita L.) and its major constituents on human cytochrome P450 enzymes. Life sciences. 2006 Jan; 78(8):856-61. doi: 10.1016/j.lfs.2005.05.095. [PMID: 16137701]
  • Blanca Rivero-Cruz, María Alejandra Rojas, Rogelio Rodríguez-Sotres, Carlos M Cerda-García-Rojas, Rachel Mata. Smooth muscle relaxant action of benzyl benzoates and salicylic acid derivatives from Brickellia veronicaefolia on isolated guinea-pig ileum. Planta medica. 2005 Apr; 71(4):320-5. doi: 10.1055/s-2005-864097. [PMID: 15856407]
  • Saban Kordali, Ahmet Cakir, Ahmet Mavi, Hamdullah Kilic, Ali Yildirim. Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species. Journal of agricultural and food chemistry. 2005 Mar; 53(5):1408-16. doi: 10.1021/jf048429n. [PMID: 15740015]
  • Eva Szöke, Emöke Máday, Sandor A Kiss, Lara Sonnewend, Eva Lemberkovics. Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures. Journal of the American College of Nutrition. 2004 Dec; 23(6):763S-7S. doi: 10.1080/07315724.2004.10719425. [PMID: 15637231]
  • Eva Szoke, Emoke Máday, Erno Tyihák, Inna N Kuzovkina, Eva Lemberkovics. New terpenoids in cultivated and wild chamomile (in vivo and in vitro). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Feb; 800(1-2):231-8. doi: 10.1016/j.jchromb.2003.09.038. [PMID: 14698259]
  • A Hernández-Ceruelos, E Madrigal-Bujaidar, C de la Cruz. Inhibitory effect of chamomile essential oil on the sister chromatid exchanges induced by daunorubicin and methyl methanesulfonate in mouse bone marrow. Toxicology letters. 2002 Sep; 135(1-2):103-110. doi: 10.1016/s0378-4274(02)00253-9. [PMID: 12243869]
  • Eleni Rekka, Michael Chrysselis, Ioanna Siskou, Angeliki Kourounakis. Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity. Chemical & pharmaceutical bulletin. 2002 Jul; 50(7):904-7. doi: 10.1248/cpb.50.904. [PMID: 12130848]
  • K Szentmihályi, E Forgács, M Hajdú, M Then. In vitro study on the transfer of volatile oil components. Journal of pharmaceutical and biomedical analysis. 2001 Mar; 24(5-6):1073-80. doi: 10.1016/s0731-7085(00)00542-2. [PMID: 11248503]
  • E A Rekka, A P Kourounakis, P N Kourounakis. Investigation of the effect of chamazulene on lipid peroxidation and free radical processes. Research communications in molecular pathology and pharmacology. 1996 Jun; 92(3):361-4. doi: . [PMID: 8827832]
  • W Carl, L S Emrich. Management of oral mucositis during local radiation and systemic chemotherapy: a study of 98 patients. The Journal of prosthetic dentistry. 1991 Sep; 66(3):361-9. doi: 10.1016/0022-3913(91)90264-w. [PMID: 1800734]
  • M KUCERA, E MACKEOVA. [Contribution to the presence and amount of chamazulene in solitary growing plants of the species Achillea millefolium L..]. Ceskoslovenska farmacie. 1955 Mar; 4(2):78-80. doi: ". [PMID: 14379238]
  • S BLAZSO. [Further results with chamazulene in the treatment of asthmatic diseases in infancy and childhood]. Schweizerische medizinische Wochenschrift. 1951 Feb; 81(5):110-1. doi: . [PMID: 14845650]