Brazilein (BioDeep_00000277527)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


Benz(b)indeno(1,2-d)pyran-9(6H)-one, 6a,7-dihydro-3,6a,10-trihydroxy-

化学式: C16H12O5 (284.0685)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 83.41%

分子结构信息

SMILES: C1C2=CC(=C(C=C2C3=C4C=CC(=O)C=C4OCC31O)O)O
InChI: InChI=1S/C16H12O5/c17-9-1-2-10-14(4-9)21-7-16(20)6-8-3-12(18)13(19)5-11(8)15(10)16/h1-5,18-20H,6-7H2

描述信息

A organic heterotetracyclic compound that is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood).

同义名列表

5 个代谢物同义名

Brazilein; Benz(b)indeno(1,2-d)pyran-9(6H)-one, 6a,7-dihydro-3,6a,10-trihydroxy-; Benz[b]indeno[1,2-d]pyran-9(6H)-one, 6a,7-dihydro-3,6a,10-trihydroxy-; 6a,9,10-Trihydroxy-6a,7-dihydrobenzo[b]indeno[1,2-d]pyran-3(6H)-one; 6a,9,10-trihydroxy-6,7-dihydroindeno[2,1-c]chromen-3-one



数据库引用编号

32 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)

4 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

  • Wenqian He, Qingfei Fan, Lan Zhou, Fengmei Huang, Xian Jiang, Zhi Na, Huabin Hu, Qishi Song. [Preparation of brazilein from Caesalpinia sappan by high performance countercurrent chromatography]. Se pu = Chinese journal of chromatography. 2020 Dec; 38(12):1363-1368. doi: 10.3724/sp.j.1123.2020.03016. [PMID: 34213250]
  • Zhongyan Mou, Yan Wang, Yongmei Li. RETRACTED: Brazilein induces apoptosis and G1/G0 phase cell cycle arrest by up-regulation of miR-133a in human vestibular schwannoma cells. Experimental and molecular pathology. 2019 04; 107(?):95-101. doi: 10.1016/j.yexmp.2018.12.010. [PMID: 30610843]
  • M S Rita de Cássia Mattos, Helton P Lemes, Sebastião R Ferreira-Filho. Correlation between pre- and post-dialysis blood pressure levels in hemodialysis patients with intradialytic hypertension. International urology and nephrology. 2016 Dec; 48(12):2095-2099. doi: 10.1007/s11255-016-1427-4. [PMID: 27671906]
  • Zhi-Yi Yuan, Fan Lei, Yu-Shuang Chai, Hao Wu, Shuang Zhao, Yu-Gang Wang, Tian-Shi Feng, Hui-Ying Li, Hui-Yu Li, Hong-Lei Zhan, Dong-Ming Xing, Li-Jun DU. Reproductive toxicity of brazilein in ICR mice. Chinese journal of natural medicines. 2016 Jun; 14(6):441-8. doi: 10.1016/s1875-5364(16)30041-3. [PMID: 27473962]
  • Xiao-Jin Yan, Yu-Shuang Chai, Zhi-Yi Yuan, Xin-Pei Wang, Jing-Fei Jiang, Fan Lei, Dong-Ming Xing, Li-Jun DU. Brazilein inhibits neuronal inflammation induced by cerebral ischemia and oxygen-glucose deprivation through targeting NOD2 expression. Chinese journal of natural medicines. 2016 May; 14(5):354-62. doi: 10.3724/sp.j.1009.2016.00354. [PMID: 27478098]
  • Watsaka Siriangkhawut, Yaowalak Khanhuathon, Piyanete Chantiratikul, Kraingkrai Ponhong, Kate Grudpan. A Green Sequential Injection Spectrophotometric Approach Using Natural Reagent Extracts from Heartwood of Ceasalpinia sappan Linn. for Determination of Aluminium. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2016; 32(3):329-36. doi: 10.2116/analsci.32.329. [PMID: 26960614]
  • Kui-Jin Kim, Kye-Yoon Yoon, Hyung-Sun Yoon, Sei-Ryang Oh, Boo-Yong Lee. Brazilein Suppresses Inflammation through Inactivation of IRAK4-NF-κB Pathway in LPS-Induced Raw264.7 Macrophage Cells. International journal of molecular sciences. 2015 Nov; 16(11):27589-98. doi: 10.3390/ijms161126048. [PMID: 26593910]
  • S Ananth, P Vivek, G Saravana Kumar, P Murugakoothan. Performance of Caesalpinia sappan heartwood extract as photo sensitizer for dye sensitized solar cells. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2015 Feb; 137(?):345-50. doi: 10.1016/j.saa.2014.08.083. [PMID: 25233024]
  • G Y Zuo, Z Q Han, X Y Hao, J Han, Z S Li, G C Wang. Synergy of aminoglycoside antibiotics by 3-Benzylchroman derivatives from the Chinese drug Caesalpinia sappan against clinical methicillin-resistant Staphylococcus aureus (MRSA). Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Jun; 21(7):936-41. doi: 10.1016/j.phymed.2014.03.004. [PMID: 24703330]
  • Kaoru Mitani, Fumihide Takano, Tetsuro Kawabata, Ahmed E Allam, Mayumi Ota, Tomoya Takahashi, Nobuo Yahagi, Chikai Sakurada, Shinji Fushiya, Tomihisa Ohta. Suppression of melanin synthesis by the phenolic constituents of sappanwood (Caesalpinia sappan). Planta medica. 2013 Jan; 79(1):37-44. doi: 10.1055/s-0032-1327897. [PMID: 23154842]
  • Wan-Chun Lai, Hui-Chun Wang, Guan-Yu Chen, Juan-Cheng Yang, Michal Korinek, Chia-Jung Hsieh, Hiroshi Nozaki, Ken-Ichiro Hayashi, Chih-Chung Wu, Yang-Chang Wu, Fang-Rong Chang. Using the pER8:GUS reporter system to screen for phytoestrogens from Caesalpinia sappan. Journal of natural products. 2011 Aug; 74(8):1698-706. doi: 10.1021/np100920q. [PMID: 21800859]
  • Tao Yin, Hong-Yu Lu, Shang-Long Zhang, Jing-Mei Liu, Da-Ming Chen. [Fruit-specific expression of sweet protein Brazzein in transgenic tomato plants]. Yi chuan = Hereditas. 2009 Jun; 31(6):663-7. doi: 10.3724/sp.j.1005.2009.00663. [PMID: 19586868]
  • Jiaqi Lan, Jun Hu, Bonan Li, Dongming Xing, Chengcheng Liu, Wei Wang, Lijun Du. Determination of brazilein in rat plasma after intravenous administration by HPLC. Biomedical chromatography : BMC. 2008 Nov; 22(11):1201-5. doi: 10.1002/bmc.1045. [PMID: 18651610]
  • Xiaoling Yan, Wei Wang, Lujun Zhang, Yunan Zhao, Dongming Xing, Lijun Du. A high-performance liquid chromatography with UV-vis detection method for the determination of Brazilein in plant extract. Journal of chromatographic science. 2007 Apr; 45(4):212-5. doi: 10.1093/chromsci/45.4.212. [PMID: 17504570]
  • Yohei Sasaki, Tomokazu Hosokawa, Masahiro Nagai, Seiji Nagumo. In vitro study for inhibition of NO production about constituents of Sappan Lignum. Biological & pharmaceutical bulletin. 2007 Jan; 30(1):193-6. doi: 10.1248/bpb.30.193. [PMID: 17202686]
  • Min Ye, Wei-Dong Xie, Fan Lei, Zhen Meng, Yu-Nan Zhao, Hui Su, Li-Jun Du. Brazilein, an important immunosuppressive component from Caesalpinia sappan L. International immunopharmacology. 2006 Mar; 6(3):426-32. doi: 10.1016/j.intimp.2005.09.012. [PMID: 16428078]
  • Xiaoling Yan, Wei Wang, Dongming Xing, Yunan Zhao, Lijun Du. Development and optimization of a method for the analysis of Brazilein by HPLC with electrochemical detection. Journal of chromatography. A. 2005 Jun; 1077(1):44-8. doi: 10.1016/j.chroma.2005.04.050. [PMID: 15988985]
  • H Puchtler, S N Meloan, F S Waldrop. Application of current chemical concepts to metal-hematein and -brazilein stains. Histochemistry. 1986; 85(5):353-64. doi: 10.1007/bf00982665. [PMID: 2430916]