Butin_(molecule) (BioDeep_00000000956)

 

Secondary id: BioDeep_00000268421, BioDeep_00000407008

PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-2,3-DIHYDRO-7-HYDROXY-, (2S)-

化学式: C15H12O5 (272.0685)
中文名称: 漆黄素, 漆黄素 ( 紫铆素)
谱图信息: 最多检出来源 Viridiplantae(otcml) 32.75%

分子结构信息

SMILES: C1(O)C=C2O[C@]([H])(C3C=CC(O)=C(O)C=3)CC(=O)C2=CC=1
InChI: InChI=1S/C15H12O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-6,14,16-17,19H,7H2

描述信息

Butin is a trihydroxyflavanone in which the three hydroxy substituents are located at positions 3, 4 and 7. It is found in Acacia mearnsii, Vernonia anthelmintica and Dalbergia odorifera and has a protective affect against oxidative stress-induced mitochondrial dysfunction. It has a role as an antioxidant, a protective agent and a metabolite. It is a trihydroxyflavanone and a member of 4-hydroxyflavanones.
Butin is a natural product found in Dipteryx lacunifera, Acacia vestita, and other organisms with data available.
A trihydroxyflavanone in which the three hydroxy substituents are located at positions 3, 4 and 7. It is found in Acacia mearnsii, Vernonia anthelmintica and Dalbergia odorifera and has a protective affect against oxidative stress-induced mitochondrial dysfunction.
(-)-Butin is the S enantiomer of Butin. Butin is a major biologically active flavonoid isolated from the heartwood of Dalbergia odorifera, with strong antioxidant, antiplatelet and anti-inflammatory activities[1][2].
(-)-Butin is the S enantiomer of Butin. Butin is a major biologically active flavonoid isolated from the heartwood of Dalbergia odorifera, with strong antioxidant, antiplatelet and anti-inflammatory activities[1][2].
(-)-Butin is the S enantiomer of Butin. Butin is a major biologically active flavonoid isolated from the heartwood of Dalbergia odorifera, with strong antioxidant, antiplatelet and anti-inflammatory activities[1][2].
(-)-Butin is the S enantiomer of Butin. Butin is a major biologically active flavonoid isolated from the heartwood of Dalbergia odorifera, with strong antioxidant, antiplatelet and anti-inflammatory activities[1][2].
Butin is a major biologically active flavonoid isolated from the heartwood of Dalbergia odorifera, with strong antioxidant, antiplatelet and anti-inflammatory activities. Butin significantly alleviates myocardial infarction and improves heart function, together with prevents diabetes-induced cardiac oxidative damage in rat[1][2].
Butin is a major biologically active flavonoid isolated from the heartwood of Dalbergia odorifera, with strong antioxidant, antiplatelet and anti-inflammatory activities. Butin significantly alleviates myocardial infarction and improves heart function, together with prevents diabetes-induced cardiac oxidative damage in rat[1][2].

同义名列表

14 个代谢物同义名

4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-2,3-DIHYDRO-7-HYDROXY-, (2S)-; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-, (S)-; (2S)-2-(3,4-DIHYDROXYPHENYL)-2,3-DIHYDRO-7-HYDROXY-4H-1-BENZOPYRAN-4-ONE; (2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-4H-chromen-4-one; (2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydrochromen-4-one; (S)-7,3,4-TRIHYDROXYFLAVANONE; FLAVANONE, 3,4,7-TRIHYDROXY-; 7,3,4-Trihydroxyflavanone; UNII-S23T8BI9DD; S23T8BI9DD; (-)-Butin; Butin; 3,4,7-Trihydroxyflavanone; Butin



数据库引用编号

23 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

1 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(1)

PharmGKB(0)

71 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 13 AKT1, BCL2, CASP3, CAT, EGFR, HTT, MAP2K4, MAPK8, NFE2L2, PIK3CA, PRKAA2, TYR, TYRP1
Peripheral membrane protein 2 ACHE, CYP1B1
Endosome membrane 3 EGFR, HTT, TYRP1
Endoplasmic reticulum membrane 4 BCL2, CYP1B1, EGFR, HSP90B1
Nucleus 14 ACHE, AKT1, BCL2, CASP3, EGFR, HSP90B1, HTT, JUN, JUND, MAP2K4, MAPK8, NFE2L2, OGG1, PRKAA2
autophagosome 1 HTT
cytosol 12 AKT1, BCL2, CASP3, CAT, HSP90B1, HTT, MAP2K4, MAPK8, NFE2L2, OGG1, PIK3CA, PRKAA2
dendrite 2 HTT, PRKAA2
centrosome 1 NFE2L2
nucleoplasm 9 AKT1, CASP3, HTT, JUN, JUND, MAPK8, NFE2L2, OGG1, PRKAA2
RNA polymerase II transcription regulator complex 3 JUN, JUND, NFE2L2
Cell membrane 4 ACHE, AKT1, EGFR, HTT
lamellipodium 2 AKT1, PIK3CA
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 1 HTT
Synapse 3 ACHE, HTT, MAPK8
cell cortex 1 AKT1
cell junction 1 EGFR
cell surface 2 ACHE, EGFR
glutamatergic synapse 3 AKT1, CASP3, EGFR
Golgi apparatus 4 ACHE, HTT, NFE2L2, PRKAA2
Golgi membrane 1 EGFR
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, PRKAA2
postsynapse 1 AKT1
presynaptic membrane 1 HTT
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 NFE2L2
Lysosome 1 TYR
endosome 1 EGFR
plasma membrane 6 ACHE, AKT1, EGFR, HTT, NFE2L2, PIK3CA
Membrane 8 ACHE, AKT1, BCL2, CAT, CYP1B1, EGFR, HSP90B1, PRKAA2
apical plasma membrane 1 EGFR
axon 4 HTT, MAP2K4, MAPK8, PRKAA2
basolateral plasma membrane 1 EGFR
extracellular exosome 3 CAT, HSP90B1, SOD2
endoplasmic reticulum 3 BCL2, HSP90B1, HTT
extracellular space 2 ACHE, EGFR
perinuclear region of cytoplasm 6 ACHE, EGFR, HSP90B1, HTT, PIK3CA, TYR
intercalated disc 1 PIK3CA
mitochondrion 5 BCL2, CAT, CYP1B1, OGG1, SOD2
protein-containing complex 7 AKT1, BCL2, CAT, EGFR, HSP90B1, HTT, OGG1
intracellular membrane-bounded organelle 3 CAT, CYP1B1, TYR
Microsome membrane 1 CYP1B1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 3 EGFR, TYR, TYRP1
Secreted 1 ACHE
extracellular region 3 ACHE, CAT, HSP90B1
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Mitochondrion matrix 1 SOD2
mitochondrial matrix 3 CAT, OGG1, SOD2
Extracellular side 1 ACHE
transcription regulator complex 2 JUN, JUND
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, EGFR
perikaryon 1 MAP2K4
microtubule cytoskeleton 1 AKT1
Melanosome membrane 2 TYR, TYRP1
midbody 1 HSP90B1
Early endosome 1 HTT
cell-cell junction 1 AKT1
Golgi-associated vesicle 1 TYR
vesicle 1 AKT1
postsynaptic membrane 1 HTT
Membrane raft 2 EGFR, HTT
pore complex 1 BCL2
Cell junction, focal adhesion 1 HTT
focal adhesion 4 CAT, EGFR, HSP90B1, HTT
spindle 1 AKT1
mitochondrial nucleoid 1 SOD2
Peroxisome 1 CAT
basement membrane 1 ACHE
intracellular vesicle 2 EGFR, TYRP1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 HSP90B1
nuclear speck 2 OGG1, PRKAA2
dendrite cytoplasm 1 MAP2K4
Late endosome 1 HTT
receptor complex 1 EGFR
Cell projection, neuron projection 1 HTT
neuron projection 1 HTT
ciliary basal body 1 AKT1
chromatin 3 JUN, JUND, NFE2L2
mediator complex 1 NFE2L2
centriole 1 HTT
nuclear chromosome 1 JUN
Lipid-anchor, GPI-anchor 1 ACHE
Endomembrane system 1 HTT
Cytoplasmic vesicle membrane 1 HTT
Nucleus, nucleoplasm 1 OGG1
Melanosome 3 HSP90B1, TYR, TYRP1
cytoplasmic stress granule 1 PRKAA2
Nucleus speckle 1 OGG1
euchromatin 1 JUN
side of membrane 1 ACHE
myelin sheath 1 BCL2
sperm plasma membrane 1 HSP90B1
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 HSP90B1
nuclear matrix 1 OGG1
transcription repressor complex 1 JUND
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
Nucleus matrix 1 OGG1
clathrin-coated endocytic vesicle membrane 2 EGFR, TYRP1
Sarcoplasmic reticulum lumen 1 HSP90B1
synaptic cleft 1 ACHE
protein-DNA complex 1 NFE2L2
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
nucleotide-activated protein kinase complex 1 PRKAA2
postsynaptic cytosol 1 HTT
presynaptic cytosol 1 HTT
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
endocytic vesicle lumen 1 HSP90B1
transcription factor AP-1 complex 2 JUN, JUND
catalase complex 1 CAT
inclusion body 1 HTT
endoplasmic reticulum chaperone complex 1 HSP90B1
BAD-BCL-2 complex 1 BCL2
[Isoform H]: Cell membrane 1 ACHE
serotonergic synapse 1 HTT
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Huntingtin]: Cytoplasm 1 HTT
[Huntingtin, myristoylated N-terminal fragment]: Cytoplasmic vesicle, autophagosome 1 HTT


文献列表

  • Yifan Lai, Qingyuan Feng, Rui Zhang, Jing Shang, Hui Zhong. The Great Capacity on Promoting Melanogenesis of Three Compatible Components in Vernonia anthelmintica (L.) Willd. International journal of molecular sciences. 2021 Apr; 22(8):. doi: 10.3390/ijms22084073. [PMID: 33920793]
  • Young Hye Seo, Tuy An Trinh, Seung Mok Ryu, Hyo Seon Kim, Goya Choi, Byeong Cheol Moon, Sang Hee Shim, Dae Sik Jang, Dongho Lee, Ki Sung Kang, Jun Lee. Chemical Constituents from the Aerial Parts of Elsholtzia ciliata and Their Protective Activities on Glutamate-Induced HT22 Cell Death. Journal of natural products. 2020 10; 83(10):3149-3155. doi: 10.1021/acs.jnatprod.0c00756. [PMID: 32991171]
  • Wei Li, Tae In Kim, Ji Hye Kim, Hwan-Suck Chung. Immune Checkpoint PD-1/PD-L1 CTLA-4/CD80 are Blocked by Rhus verniciflua Stokes and its Active Compounds. Molecules (Basel, Switzerland). 2019 Nov; 24(22):. doi: 10.3390/molecules24224062. [PMID: 31717574]
  • Jinfeng Yang, Yong Soo Kwon, Myong Jo Kim. Antimicrobial activity and active compounds of a Rhus verniciflua Stokes extract. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2018 Nov; 73(11-12):457-463. doi: 10.1515/znc-2018-0054. [PMID: 30183668]
  • Hongxia Chen, Chengzhang Wang, Hao Zhou, Ran Tao, Jianzhong Ye, Wenjun Li. Antioxidant capacity and identification of the constituents of ethyl acetate fraction from Rhus verniciflua Stokes by HPLC-MS. Natural product research. 2017 Jul; 31(13):1573-1577. doi: 10.1080/14786419.2016.1277353. [PMID: 28100074]
  • Shi-Xia Huo, Qiong Wang, Xin-Min Liu, Chun-Hui Ge, Li Gao, Xiao-Ming Peng, Ming Yan. The Effect of Butin on the Vitiligo Mouse Model Induced by Hydroquinone. Phytotherapy research : PTR. 2017 May; 31(5):740-746. doi: 10.1002/ptr.5794. [PMID: 28321929]
  • Di Zhou, Hongyan Wei, Zhe Jiang, Xuezheng Li, Kun Jiao, Xiaoguang Jia, Yue Hou, Ning Li. Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap. Bioorganic & medicinal chemistry letters. 2017 02; 27(4):973-978. doi: 10.1016/j.bmcl.2016.12.075. [PMID: 28073678]
  • Myeong Hyeon Park, In Sook Kim, Sun-A Kim, Chun-Soo Na, Cheol Yi Hong, Mi-Sook Dong, Hye Hyun Yoo. Inhibitory effect of Rhus verniciflua Stokes extract on human aromatase activity; butin is its major bioactive component. Bioorganic & medicinal chemistry letters. 2014 Apr; 24(7):1730-3. doi: 10.1016/j.bmcl.2014.02.039. [PMID: 24630560]
  • Namki Cho, Ji Hoon Choi, Heejung Yang, Eun Ju Jeong, Ki Yong Lee, Young Choong Kim, Sang Hyun Sung. Neuroprotective and anti-inflammatory effects of flavonoids isolated from Rhus verniciflua in neuronal HT22 and microglial BV2 cell lines. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Jun; 50(6):1940-5. doi: 10.1016/j.fct.2012.03.052. [PMID: 22465834]
  • So Young Kang, Ji-Young Kang, Myung-Joo Oh. Antiviral activities of flavonoids isolated from the bark of Rhus verniciflua stokes against fish pathogenic viruses In Vitro. Journal of microbiology (Seoul, Korea). 2012 Apr; 50(2):293-300. doi: 10.1007/s12275-012-2068-7. [PMID: 22538659]
  • Chenchen Zhang, Jun Liu, Huijun Pan, Xiaolu Yang, Ka Bian. [Mitochondrial dysfunction induced by excessive ROS/RNS-metabolic cardiovascular disease and traditional Chinese medicines intervention]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Sep; 36(17):2423-8. doi: . [PMID: 22121816]
  • Diana S Antal, Stefan Schwaiger, Ernst P Ellmerer-Müller, Hermann Stuppner. Cotinus coggygria wood: novel flavanone dimer and development of an HPLC/UV/MS method for the simultaneous determination of fourteen phenolic constituents. Planta medica. 2010 Oct; 76(15):1765-72. doi: 10.1055/s-0030-1249878. [PMID: 20446241]
  • R Gadekar, P K Singour, P K Chaurasiya, R S Pawar, U K Patil. A potential of some medicinal plants as an antiulcer agents. Pharmacognosy reviews. 2010 Jul; 4(8):136-46. doi: 10.4103/0973-7847.70906. [PMID: 22228953]
  • Kristine M Olsen, Alain Hehn, Hélène Jugdé, Rune Slimestad, Romain Larbat, Frédéric Bourgaud, Cathrine Lillo. Identification and characterisation of CYP75A31, a new flavonoid 3'5'-hydroxylase, isolated from Solanum lycopersicum. BMC plant biology. 2010 Feb; 10(?):21. doi: 10.1186/1471-2229-10-21. [PMID: 20128892]
  • Sadia Ferheen, Nighat Afza, Abdul Malik, Lubna Iqbal, Muhammad Azam Rasool, Muhammad Irfan Ali, Rasool Bakhsh Tareen. Galinsosides A and B, bioactive flavanone glucosides from Galinsoga parviflora. Journal of enzyme inhibition and medicinal chemistry. 2009 Oct; 24(5):1128-32. doi: 10.1080/14756360802667688. [PMID: 19772485]
  • Lemonia Valianou, Konstantina Stathopoulou, Ioannis Karapanagiotis, Prokopios Magiatis, Eleni Pavlidou, Alexios-Leandros Skaltsounis, Yannis Chryssoulakis. Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles. Analytical and bioanalytical chemistry. 2009 Jun; 394(3):871-82. doi: 10.1007/s00216-009-2767-z. [PMID: 19352635]
  • Rui Zhang, Sungwook Chae, Kyoung Ah Kang, Mei Jing Piao, Dong Ok Ko, Zhi Hong Wang, Doek Bae Park, Jae Woo Park, Ho Jin You, Jin Won Hyun. Protective effect of butin against hydrogen peroxide-induced apoptosis by scavenging reactive oxygen species and activating antioxidant enzymes. Molecular and cellular biochemistry. 2008 Nov; 318(1-2):33-42. doi: 10.1007/s11010-008-9854-x. [PMID: 18594949]
  • Ilaria Lampronti, Mahmud T H Khan, Monica Borgatti, Nicoletta Bianchi, Roberto Gambari. Inhibitory Effects of Bangladeshi Medicinal Plant Extracts on Interactions between Transcription Factors and Target DNA Sequences. Evidence-based complementary and alternative medicine : eCAM. 2008 Sep; 5(3):303-12. doi: 10.1093/ecam/nem042. [PMID: 18830455]
  • Supaluk Prachayasittikul, Prasit Buraparuangsang, Apilak Worachartcheewan, Chartchalerm Isarankura-Na-Ayudhya, Somsak Ruchirawat, Virapong Prachayasittikul. Antimicrobial and antioxidative activities of bioactive constituents from Hydnophytum formicarum Jack. Molecules (Basel, Switzerland). 2008 Apr; 13(4):904-21. doi: 10.3390/molecules13040904. [PMID: 18463592]
  • M V Sogonov, L A Castlebury, A Y Rossman, L C Mejía, J F White. Leaf-inhabiting genera of the Gnomoniaceae, Diaporthales. Studies in mycology. 2008; 62(?):1-77. doi: 10.3114/sim.2008.62.01. [PMID: 19287541]
  • L Selbmann, G S de Hoog, L Zucconi, D Isola, S Ruisi, A H G Gerrits van den Ende, C Ruibal, F De Leo, C Urzì, S Onofri. Drought meets acid: three new genera in a dothidealean clade of extremotolerant fungi. Studies in mycology. 2008; 61(?):1-20. doi: 10.3114/sim.2008.61.01. [PMID: 19287523]
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  • Won Kyung Jeon, Ju Hyun Lee, Ho Kyoung Kim, A Yeong Lee, Sung Ok Lee, Young Sup Kim, Shi Yong Ryu, Soo Young Kim, Yong Jin Lee, Byoung Seob Ko. Anti-platelet effects of bioactive compounds isolated from the bark of Rhus verniciflua Stokes. Journal of ethnopharmacology. 2006 Jun; 106(1):62-9. doi: 10.1016/j.jep.2005.12.015. [PMID: 16431050]
  • Mei-Hsien Lee, Yi-Pei Lin, Feng-Lin Hsu, Gui-Rong Zhan, Kun-Ying Yen. Bioactive constituents of Spatholobus suberectus in regulating tyrosinase-related proteins and mRNA in HEMn cells. Phytochemistry. 2006 Jun; 67(12):1262-70. doi: 10.1016/j.phytochem.2006.05.008. [PMID: 16782143]
  • Rong-Xia Liu, Qiao Wang, Hong-Zhu Guo, Li Li, Kai-Shun Bi, De-An Guo. Simultaneous determination of 10 major flavonoids in Dalbergia odorifera by high performance liquid chromatography. Journal of pharmaceutical and biomedical analysis. 2005 Sep; 39(3-4):469-76. doi: 10.1016/j.jpba.2005.04.007. [PMID: 15935596]