Brazilin (BioDeep_00000000345)

 

Secondary id: BioDeep_00000176814, BioDeep_00001875897

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(1R,10S)-8-oxatetracyclo[8.7.0.0?,?.0??,??]heptadeca-2(7),3,5,12,14,16-hexaene-5,10,14,15-tetrol

化学式: C16H14O5 (286.0841194)
中文名称: 巴西苏木素, 苏枋精
谱图信息: 最多检出来源 Viridiplantae(plant) 8.33%

分子结构信息

SMILES: C1(O)C=CC2C3C4C=C(O)C(O)=CC=4CC3(O)COC=2C=1
InChI: InChI=1S/C16H14O5/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/h1-5,15,17-20H,6-7H2

描述信息

Brazilin is a organic heterotetracyclic compound that is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood). It has a role as a plant metabolite, a histological dye, an antineoplastic agent, a biological pigment, an anti-inflammatory agent, an apoptosis inducer, an antioxidant, an antibacterial agent, a NF-kappaB inhibitor and a hepatoprotective agent. It is an organic heterotetracyclic compound, a member of catechols and a tertiary alcohol.
Brazilin is a natural product found in Guilandina bonduc, Biancaea decapetala, and other organisms with data available.
A organic heterotetracyclic compound that is a red pigment obtained from the wood of Caesalpinia echinata (Brazil-wood) or Caesalpinia sappan (sappan-wood).
Brazilin is a red dye precursor obtained from the heartwood of several species of tropical hardwoods. Brazilin inhibits the cells proliferation, promotes apoptosis, and induces autophagy through the AMPK/mTOR pathway. Brazilin shows chondroprotective and anti-inflammatory activities[1][2][3].
Brazilin is a red dye precursor obtained from the heartwood of several species of tropical hardwoods. Brazilin inhibits the cells proliferation, promotes apoptosis, and induces autophagy through the AMPK/mTOR pathway. Brazilin shows chondroprotective and anti-inflammatory activities[1][2][3].

同义名列表

21 个代谢物同义名

(1R,10S)-8-oxatetracyclo[8.7.0.0?,?.0??,??]heptadeca-2(7),3,5,12,14,16-hexaene-5,10,14,15-tetrol; Benz(b)indeno(1,2-d)pyran-3,6a,9,10(6H)-tetrol, 7,11b-dihydro-, (6aS,11bR)-; Benz[b]indeno[1,2-d]pyran-3,6a,9,10(6H)-tetrol, 7,11b-dihydro-,(6aS,11bR)-; (6AS,11BR)-7,11B-DIHYDROBENZ(B)INDENO(1,2-D)PYRAN-3,6A,9,10(6H)-TETROL; Benz(b)indeno(1,2-d)pyran-3,6a,9,10(6H)-tetrol, 7,11b-dihydro- (VAN); (6aS,11bR)-7,11b-dihydroindeno[2,1-c]chromene-3,6a,9,10(6H)-tetrol; (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,6a,9,10-tetrol; 7,11b-Dihydrobenz(b)indeno(1,2-d)pyran-3,6a,9,10(6H)-tetrol; c.i. natural red 24; C.I.Natural Red 24; UNII-FZ39SW1K10; Superbresiline; Natural Red 24; BRAZILIN [MI]; (+)-BRAZILIN; Braziletto; FZ39SW1K10; BRASILINE; brasilin; Brazilin; (6aS) -6,6a,7,11bbeta-Tetrahydrobenzo [ b ] indeno [ 1,2-d ] pyran-3,6abeta,9,10-tetraol



数据库引用编号

33 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)

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

  • Shengxuan Li, Kun Wang, Kai Jiang, Dongmei Xing, Ruhua Deng, Yue Xu, Yue Ding, Huida Guan, Lin-Lin Chen, Dandan Wang, Yang Chen, Wenbo Bu, Yaozu Xiang. Brazilin-Ce nanoparticles attenuate inflammation by de/anti-phosphorylation of IKKβ. Biomaterials. 2024 Mar; 305(?):122466. doi: 10.1016/j.biomaterials.2023.122466. [PMID: 38184960]
  • Zhan Cui, Fang-Yan Guo, Li Li, Fuping Lu, Cheng-Hua Jin, Xiangming Wang, Fufeng Liu. Brazilin-7-acetate, a novel potential drug of Parkinson's disease, hinders the formation of α-synuclein fibril, mitigates cytotoxicity, and decreases oxidative stress. European journal of medicinal chemistry. 2024 Jan; 264(?):115965. doi: 10.1016/j.ejmech.2023.115965. [PMID: 38056304]
  • Chaiwat Arjin, Suriya Tateing, Nuttha Potapohn, Jirapat Arunorat, Kidsadagon Pringproa, Chompunut Lumsangkul, Mintra Seel-Audom, Warintorn Ruksiriwanich, Korawan Sringarm. Brazilin from Caesalpinia sappan inhibits viral infection against PRRSV via CD163ΔSRCR5 MARC-145 cells: an in silico and in vitro studies. Scientific reports. 2022 12; 12(1):21595. doi: 10.1038/s41598-022-26206-x. [PMID: 36517668]
  • Jong Il Park, Sung Jae Kim, Yong Jae Kim, Seung Ji Lee. Protective role of Caesalpinia sappan extract and its main component brazilin against blue light-induced damage in human fibroblasts. Journal of cosmetic dermatology. 2022 Dec; 21(12):7025-7034. doi: 10.1111/jocd.15354. [PMID: 36057446]
  • Biji Chatterjee, Krishna Ghosh, Aishwarya Swain, Kiran Kumar Nalla, Haritha Ravula, Archana Pan, Santosh R Kanade. The phytochemical brazilin suppress DNMT1 expression by recruiting p53 to its promoter resulting in the epigenetic restoration of p21 in MCF7cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jan; 95(?):153885. doi: 10.1016/j.phymed.2021.153885. [PMID: 34920321]
  • Anna Goc, Waldemar Sumera, Matthias Rath, Aleksandra Niedzwiecki. Phenolic compounds disrupt spike-mediated receptor-binding and entry of SARS-CoV-2 pseudo-virions. PloS one. 2021; 16(6):e0253489. doi: 10.1371/journal.pone.0253489. [PMID: 34138966]
  • Sukanya Settharaksa, Chaowalit Monton, Laksana Charoenchai. Optimization of Caesalpinia sappan L. heartwood extraction procedure to obtain the highest content of brazilin and greatest antibacterial activity. Journal of integrative medicine. 2019 Sep; 17(5):351-358. doi: 10.1016/j.joim.2019.05.003. [PMID: 31130448]
  • Yameng Jia, Xiaozhe Tong, Jingyan Fan. [Effect of brazilin on apoptosis and autophagy of tongue cancer Tca8113 cells and its molecular mechanism]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University. 2019 Mar; 39(3):351-356. doi: 10.12122/j.issn.1673-4254.2019.03.14. [PMID: 31068315]
  • Xi Wang, Zi Xiu, Yuru Du, Yiming Li, Juxiang Yang, Yuan Gao, Fangfang Li, Xi Yin, Haishui Shi. Brazilin Treatment Produces Antidepressant- and Anxiolytic-Like Effects in Mice. Biological & pharmaceutical bulletin. 2019; 42(8):1268-1274. doi: 10.1248/bpb.b18-00882. [PMID: 31366864]
  • Daniela Weinmann, Monika Mueller, Sonja M Walzer, Gerhard M Hobusch, Richard Lass, Claudia Gahleitner, Helmut Viernstein, Reinhard Windhager, Stefan Toegel. Brazilin blocks catabolic processes in human osteoarthritic chondrocytes via inhibition of NFKB1/p50. Journal of orthopaedic research : official publication of the Orthopaedic Research Society. 2018 09; 36(9):2431-2438. doi: 10.1002/jor.24013. [PMID: 29704279]
  • Hyung Seo Hwang, Joong Hyun Shim. Brazilin and Caesalpinia sappan L. extract protect epidermal keratinocytes from oxidative stress by inducing the expression of GPX7. Chinese journal of natural medicines. 2018 Mar; 16(3):203-209. doi: 10.1016/s1875-5364(18)30048-7. [PMID: 29576056]
  • Rinrampai Puttipan, Sunee Chansakaow, Sakornrat Khongkhunthian, Siriporn Okonogi. Caesalpinia sappan: A promising natural source of antimicrobial agent for inhibition of cariogenic bacteria. Drug discoveries & therapeutics. 2018 ; 12(4):197-205. doi: 10.5582/ddt.2018.01035. [PMID: 30224592]
  • Zhan-Yuan Li, Yu Zheng, Yan Chen, Min Pan, Shu-Bei Zheng, Wen Huang, Zhi-Hong Zhou, Han-Yang Ye. Brazilin Ameliorates Diabetic Nephropathy and Inflammation in db/db Mice. Inflammation. 2017 Aug; 40(4):1365-1374. doi: 10.1007/s10753-017-0579-4. [PMID: 28497277]
  • Eun Byeol Lee, Ming Ming Xing, Dae Keun Kim. Lifespan-extending and stress resistance properties of brazilin from Caesalpinia sappan in Caenorhabditis elegans. Archives of pharmacal research. 2017 Jul; 40(7):825-835. doi: 10.1007/s12272-017-0920-3. [PMID: 28667441]
  • Yanyan Jia, Jinyi Zhao, Meiyou Liu, Bingling Li, Ying Song, Yuwen Li, Aidong Wen, Lei Shi. Brazilin exerts protective effects against renal ischemia-reperfusion injury by inhibiting the NF-κB signaling pathway. International journal of molecular medicine. 2016 Jul; 38(1):210-6. doi: 10.3892/ijmm.2016.2616. [PMID: 27247107]
  • 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]
  • Ying-Yang Xu, Jia Yin. Contact dermatitis caused by brazilin in Caesalpinia sappan. Contact dermatitis. 2015 Sep; 73(3):189-90. doi: 10.1111/cod.12412. [PMID: 25960163]
  • Supinya Tewtrakul, Pattreeya Tungcharoen, Teeratad Sudsai, Chatchanok Karalai, Chanita Ponglimanont, Orapun Yodsaoue. Antiinflammatory and Wound Healing Effects of Caesalpinia sappan L. Phytotherapy research : PTR. 2015 Jun; 29(6):850-6. doi: 10.1002/ptr.5321. [PMID: 25760294]
  • Golam Mezbah Uddin, Chul Young Kim, Donghwa Chung, Kyung-A Kim, Sang Hoon Jung. One-step isolation of sappanol and brazilin from Caesalpinia sappan and their effects on oxidative stress-induced retinal death. BMB reports. 2015 May; 48(5):289-94. doi: 10.5483/bmbrep.2015.48.5.189. [PMID: 25248564]
  • Eui-Gil Jung, Kook-Il Han, Seon Gu Hwang, Hyun-Jung Kwon, Bharat Bhusan Patnaik, Yong Hyun Kim, Man-Deuk Han. Brazilin isolated from Caesalpinia sappan L. inhibits rheumatoid arthritis activity in a type-II collagen induced arthritis mouse model. BMC complementary and alternative medicine. 2015 Apr; 15(?):124. doi: 10.1186/s12906-015-0648-x. [PMID: 25896410]
  • 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]
  • Nilesh Prakash Nirmal, Pharkphoom Panichayupakaranant. Antioxidant, antibacterial, and anti-inflammatory activities of standardized brazilin-rich Caesalpinia sappan extract. Pharmaceutical biology. 2015; 53(9):1339-43. doi: 10.3109/13880209.2014.982295. [PMID: 25864864]
  • Seong-Hoon Kim, Ha-Na Lyu, Ye Seul Kim, Yong Hyun Jeon, Wanil Kim, Sangjune Kim, Jong-Kwan Lim, Ho Won Lee, Nam-In Baek, Kwan-Yong Choi, Jaetae Lee, Kyong-Tai Kim. Brazilin Isolated from Caesalpinia sappan suppresses nuclear envelope reassembly by inhibiting barrier-to-autointegration factor phosphorylation. The Journal of pharmacology and experimental therapeutics. 2015 Jan; 352(1):175-84. doi: 10.1124/jpet.114.218792. [PMID: 25369797]
  • Nilesh Prakash Nirmal, Pharkphoom Panichayupakaranant. Anti-Propionibacterium acnes assay-guided purification of brazilin and preparation of brazilin rich extract from Caesalpinia sappan heartwood. Pharmaceutical biology. 2014 Sep; 52(9):1204-7. doi: 10.3109/13880209.2014.884607. [PMID: 24963948]
  • Qing Zhang, Jing-Li Liu, Xiao-Man Qi, Chun-Ting Qi, Qiang Yu. Inhibitory activities of Lignum Sappan extractives on growth and growth-related signaling of tumor cells. Chinese journal of natural medicines. 2014 Aug; 12(8):607-12. doi: 10.1016/s1875-5364(14)60092-3. [PMID: 25156286]
  • 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]
  • Thanasekaran Jayakumar, Chao-Chien Chang, Shoei-Loong Lin, Yung-Kai Huang, Chien-Ming Hu, Antoinet Ramola Elizebeth, Shih-Chang Lin, Cheuk-Sing Choy. Brazilin ameliorates high glucose-induced vascular inflammation via inhibiting ROS and CAMs production in human umbilical vein endothelial cells. BioMed research international. 2014; 2014(?):403703. doi: 10.1155/2014/403703. [PMID: 24716195]
  • Jia Yan-yan, Li Yan, Song Ying, Zhao Jinyi, Dou Fang, Sun Yuan, Wen Ai-dong. A simple high-performance liquid chromatographic method for the determination of brazilin and its application to a pharmacokinetic study in rats. Journal of ethnopharmacology. 2014; 151(1):108-13. doi: 10.1016/j.jep.2013.08.054. [PMID: 24095700]
  • Yanyan Jia, Hujun Wang, Ying Song, Kai Liu, Fang Dou, Chengtao Lu, Jie Ge, Ningjuan Chi, Yi Ding, Wenli Hai, Aidong Wen. Application of a liquid chromatography-tandem mass spectrometry method to the pharmacokinetics, tissue distribution and excretion studies of brazilin in rats. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Jul; 931(?):61-7. doi: 10.1016/j.jchromb.2013.05.017. [PMID: 23777611]
  • Xiao-Zhe Tong, Hui Zhu, Yan Shi, Hai-Tao Xu, Biao Wang, Jiu-Han Zhao. An LC/MS/MS method for simultaneous quantitation of two homoisoflavones: protosappanin B and brazilin with hypoglycemic activity in rat plasma and its application to a comparative pharmacokinetic study in normal and streptozotocin-treated rats. Journal of ethnopharmacology. 2013 Jul; 148(2):682-90. doi: 10.1016/j.jep.2013.05.029. [PMID: 23707335]
  • Zhipeng Deng, Xin Wang, Huanxin Zhao, Shuxiang Cui, Qingqiang Yao, Hong Bai. A validated LC-MS/MS method for rapid determination of brazilin in rat plasma and its application to a pharmacokinetic study. Biomedical chromatography : BMC. 2013 Jun; 27(6):802-6. doi: 10.1002/bmc.2863. [PMID: 23303567]
  • Dipita Bhakta, Sajitha Lulu, G Jayaraman, S Babu, Ramamoorthy Siva. Interaction of plant pigment brazilin with synthetic and natural DNA: spectroscopic and in silico perspective. Interdisciplinary sciences, computational life sciences. 2013 Mar; 5(1):53-9. doi: 10.1007/s12539-013-0148-y. [PMID: 23605640]
  • Yi Chang, Steven Kuan-Hua Huang, Wan-Jung Lu, Chi-Li Chung, Wei-Lin Chen, Shun-Hua Lu, Kuan-Hung Lin, Joen-Rong Sheu. Brazilin isolated from Caesalpinia sappan L. acts as a novel collagen receptor agonist in human platelets. Journal of biomedical science. 2013 Jan; 20(?):4. doi: 10.1186/1423-0127-20-4. [PMID: 23350663]
  • Pingping Xu, Shuhong Guan, Ruihong Feng, Renneng Tang, Dean Guo. Separation of four homoisoflavonoids from Caesalpinia sappan by high-speed counter-current chromatography. Phytochemical analysis : PCA. 2012 May; 23(3):228-31. doi: 10.1002/pca.1347. [PMID: 21853494]
  • 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]
  • Yohei Sasaki, Maemi Suzuki, Takayuki Matsumoto, Tomokazu Hosokawa, Tsuneo Kobayashi, Katsuo Kamata, Seiji Nagumo. Vasorelaxant activity of Sappan Lignum constituents and extracts on rat aorta and mesenteric artery. Biological & pharmaceutical bulletin. 2010; 33(9):1555-60. doi: 10.1248/bpb.33.1555. [PMID: 20823574]
  • 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]
  • Byung-Min Choi, Ju-A Lee, Shang Shang Gao, Sang Yong Eun, Young-Sup Kim, Shi-Yong Ryu, Yeon-Hee Choi, Raekil Park, Dae Young Kwon, Bok-Ryang Kim. Brazilin and the extract from Caesalpinia sappan L. protect oxidative injury through the expression of heme oxygenase-1. BioFactors (Oxford, England). 2007; 30(3):149-57. doi: 10.1002/biof.5520300302. [PMID: 18525109]
  • Hong-Xi Xu, Song F Lee. The antibacterial principle of Caesalpina sappan. Phytotherapy research : PTR. 2004 Aug; 18(8):647-51. doi: 10.1002/ptr.1524. [PMID: 15476302]
  • Chien Ming Hu, Jaw Jou Kang, Chen Chen Lee, Ching Hao Li, Jiunn Wang Liao, Yu Wen Cheng. Induction of vasorelaxation through activation of nitric oxide synthase in endothelial cells by brazilin. European journal of pharmacology. 2003 May; 468(1):37-45. doi: 10.1016/s0014-2999(03)01639-x. [PMID: 12729841]
  • Woongchon Mar, Hyun-Tai Lee, Kang-Hoon Je, Hye-Young Choi, Eun-Kyoung Seo. A DNA strand-nicking principle of a higher plant, Caesalpinia sappan. Archives of pharmacal research. 2003 Feb; 26(2):147-50. doi: 10.1007/bf02976661. [PMID: 12643592]
  • Y W Xie, D S Ming, H X Xu, H Dong, P P But. Vasorelaxing effects of Caesalpinia sappan involvement of endogenous nitric oxide. Life sciences. 2000 Sep; 67(15):1913-8. doi: 10.1016/s0024-3205(00)00772-4. [PMID: 11043613]
  • L Y Khil, S S Han, S G Kim, T S Chang, S D Jeon, D S So, C K Moon. Effects of brazilin on GLUT4 recruitment in isolated rat epididymal adipocytes. Biochemical pharmacology. 1999 Dec; 58(11):1705-12. doi: 10.1016/s0006-2952(99)00275-0. [PMID: 10571244]
  • S Y Choi, K M Yang, S D Jeon, J H Kim, L Y Khil, T S Chang, C K Moon. Brazilin modulates immune function mainly by augmenting T cell activity in halothane administered mice. Planta medica. 1997 Oct; 63(5):405-8. doi: 10.1055/s-2006-957722. [PMID: 9342942]
  • C K Moon, S H Lee, M O Lee, S G Kim. Effects of Brazilin on glucose oxidation, lipogenesis and therein involved enzymes in adipose tissues from diabetic KK-mice. Life sciences. 1993; 53(16):1291-7. doi: 10.1016/0024-3205(93)90574-m. [PMID: 8412489]
  • C K Moon, K S Park, S G Kim, H S Won, J H Chung. Brazilin protects cultured rat hepatocytes from BrCCl3-induced toxicity. Drug and chemical toxicology. 1992; 15(1):81-91. doi: 10.3109/01480549209035174. [PMID: 1555525]
  • 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]