sulfurein (BioDeep_00000000826)

 

Secondary id: BioDeep_00000270745

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


(2Z)-2-[[3,4-bis(oxidanyl)phenyl]methylidene]-6-oxidanyl-1-benzofuran-3-one

化学式: C15H10O5 (270.052821)
中文名称: 硫黄菊素
谱图信息: 最多检出来源 Viridiplantae(plant) 11.85%

分子结构信息

SMILES: C1=CC(=C(C=C1C=C2C(=O)C3=C(O2)C=C(C=C3)O)O)O
InChI: InChI=1S/C15H10O5/c16-9-2-3-10-13(7-9)20-14(15(10)19)6-8-1-4-11(17)12(18)5-8/h1-7,16-18H/b14-6-

描述信息

Sulfuretin is a member of 1-benzofurans.
Sulfuretin is a natural product found in Calanticaria bicolor, Dipteryx lacunifera, and other organisms with data available.
Sulfuretin inhibits the inflammatory response by suppressing the NF-κB pathway. Sulfuretin can be used for the research of allergic airway inflammation. Sulfuretin reduces oxidative stress, platelet aggregation, and mutagenesis[1]. Sulfuretin is a competitive and potent inhibitor of monophenolase and diphenolase activities with the IC50 of 13.64 μM[2].
Sulfuretin inhibits the inflammatory response by suppressing the NF-κB pathway. Sulfuretin can be used for the research of allergic airway inflammation. Sulfuretin reduces oxidative stress, platelet aggregation, and mutagenesis[1]. Sulfuretin is a competitive and potent inhibitor of monophenolase and diphenolase activities with the IC50 of 13.64 μM[2].

同义名列表

33 个代谢物同义名

(2Z)-2-[[3,4-bis(oxidanyl)phenyl]methylidene]-6-oxidanyl-1-benzofuran-3-one; 3(2H)-BENZOFURANONE, 2-((3,4-DIHYDROXYPHENYL)METHYLENE)-6-HYDROXY-, (2Z)-; 3(2H)-Benzofuranone, 2-[(3,4-dihydroxyphenyl)methylene]-6-hydroxy-, (2Z)-; 3(2H)-Benzofuranone, 2-((3,4-dihydroxyphenyl)methylene)-6-hydroxy-, (Z)-; (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-1-benzofuran-3-one; (Z)-2-[(3,4-dihydroxyphenyl)methylene]-6-hydroxy-2H-benzofuran-3-one; (Z)-2-((3,4-Dihydroxyphenyl)methylene)-6-hydroxy-2H-benzofuran-3-one; (2Z)-2-(3,4-Dihydroxybenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one #; (2Z)-2-[(3,4-dihydroxyphenyl)methylidene]-6-hydroxy-3-benzofuranone; (2Z)-2-(3,4-Dihydroxybenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one; (2Z)-2-[(3,4-dihydroxyphenyl)methylene]-6-hydroxy-benzofuran-3-one; (z)-2-(3,4-dihydroxybenzylidene)-6-hydroxybenzofuran-3(2h)-one; 3(2H)-BENZOFURANONE, 2-(3,4-DIHYDROXYBENZYLIDENE)-6-HYDROXY-; (2Z)-2-(3,4-dihydroxybenzylidene)-6-hydroxy-coumaran-3-one; 2-(3,4-dihydroxybenzylidene)-6-hydroxy-3(2H)-benzofuranone; 3,4,6-Trihydroxyaurone; 3,4,6-Trihydroxybenzalcoumaranone; Benzofran-3-one, 2-[3,4-dihydroxybenzylidene]-6-hydroxy-; 3,4,6-TRIHYDROXYBENZALCOUMARANONE; ISOLIQUIRITIGENIN METABOLITE M3; RGNXWPVNPFAADO-NSIKDUERSA-N; Aurone, 6,3,4-trihydroxy-; 3,4,6-trihydroxyaurone; 3,4,6-Trihydroxyaurone; 6,3,4-Trihydroxyaurone; aurone sulfuretin; SULFURETIN [MI]; MEGxp0_001715; ACon1_000213; Sulphuretin; Sulfuretin; sulfurein; 120-05-8; Sulphuretin



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • aurone biosynthesis: 2',3,4,4',6'-pentahydroxychalcone 4'-O-β-D-glucoside + O2 ⟶ H2O + bracteatin 6-O-glucoside

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

  • aurone biosynthesis: O2 + butein 4'-β-D-glucoside ⟶ H2O + aureusidin 6-O-glucoside
  • aurone biosynthesis: 2',3,4,4',6'-pentahydroxychalcone 4'-O-β-D-glucoside + O2 ⟶ H2O + aureusidin 6-O-glucoside

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

25 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。



文献列表

  • 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]
  • Miroslav Novakovic, Iris Djordjevic, Nina Todorovic, Snezana Trifunovic, Boban Andjelkovic, Boris Mandic, Milka Jadranin, Ivan Vuckovic, Vlatka Vajs, Slobodan Milosavljevic, Vele Tesevic. New aurone epoxide and auronolignan from the heartwood of Cotinus coggygria Scop. Natural product research. 2019 Oct; 33(19):2837-2844. doi: 10.1080/14786419.2018.1508141. [PMID: 30513208]
  • 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]
  • Suji Kim, No-Joon Song, Gahee Bahn, Seo-Hyuk Chang, Ui Jeong Yun, Jin-Mo Ku, Dong-Gyu Jo, Kye Won Park. Atf3 induction is a therapeutic target for obesity and metabolic diseases. Biochemical and biophysical research communications. 2018 10; 504(4):903-908. doi: 10.1016/j.bbrc.2018.09.048. [PMID: 30224057]
  • Pingdong Jiang, Hui Sun. Sulfuretin alleviates atopic dermatitis-like symptoms in mice via suppressing Th2 cell activity. Immunologic research. 2018 10; 66(5):611-619. doi: 10.1007/s12026-018-9025-4. [PMID: 30159861]
  • Ramakanta Lamichhane, Se-Gun Kim, Sona Kang, Kyung-Hee Lee, Prakash Raj Pandeya, Hyun-Ju Jung. Exploration of Underlying Mechanism of Anti-adipogenic Activity of Sulfuretin. Biological & pharmaceutical bulletin. 2017 Sep; 40(9):1366-1373. doi: 10.1248/bpb.b17-00049. [PMID: 28579594]
  • 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]
  • Kangsan Roh, Suji Kim, Hee Kang, Jin-Mo Ku, Kye Won Park, Sukchan Lee. Sulfuretin has therapeutic activity against acquired lymphedema by reducing adipogenesis. Pharmacological research. 2017 Jul; 121(?):230-239. doi: 10.1016/j.phrs.2017.05.003. [PMID: 28483479]
  • Tae Gyu Nam, Bong Han Lee, Hyo-Kyoung Choi, Ahmad Rois Mansur, Sang Gil Lee, Dae-Ok Kim. Rhus verniciflua Stokes Extract and Its Flavonoids Protect PC-12 Cells against H2O2-Induced Cytotoxicity. Journal of microbiology and biotechnology. 2017 Jun; 27(6):1090-1097. doi: 10.4014/jmb.1612.12018. [PMID: 28376611]
  • Nguyen Phuong Thao, Bui Thi Thuy Luyen, Bui Huu Tai, Nguyen Manh Cuong, Youn Chul Kim, Chau Van Minh, Young Ho Kim. Chemical constituents of Miliusa balansae leaves and inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells. Bioorganic & medicinal chemistry letters. 2015 Sep; 25(18):3859-63. doi: 10.1016/j.bmcl.2015.07.056. [PMID: 26238320]
  • Guan Chen, Cheng-Bin Cui, Ai-Di Qi, Chang-Wei Li, Zun-Wei Tao, Rong Ren. Polyanthumin, a novel cyclobutane chalcone trimmer from Memecylon polyanthum. Journal of Asian natural products research. 2015; 17(2):170-7. doi: 10.1080/10286020.2014.945439. [PMID: 25434469]
  • Jun-Hyeong Lee, Mikyung Kim, Kyung-Hwa Chang, Cheol Yi Hong, Chun-Soo Na, Mi-Sook Dong, Dongho Lee, Moo-Yeol Lee. Antiplatelet effects of Rhus verniciflua stokes heartwood and its active constituents--fisetin, butein, and sulfuretin--in rats. Journal of medicinal food. 2015 Jan; 18(1):21-30. doi: 10.1089/jmf.2013.3116. [PMID: 25372471]
  • 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]
  • Soon Jung Choi, Min Young Lee, Hyoung Jo, Soon Sung Lim, Sang Hoon Jung. Preparative isolation and purification of neuroprotective compounds from Rhus verniciflua by high speed counter-current chromatography. Biological & pharmaceutical bulletin. 2012; 35(4):559-67. doi: 10.1248/bpb.35.559. [PMID: 22466561]
  • Woncheol Choi, Hyunsik Jung, Kyungsuk Kim, Sookyung Lee, Seongwoo Yoon, Jaehyun Park, Sehyun Kim, Seongha Cheon, Wankyo Eo, Sanghun Lee. Rhus verniciflua stokes against advanced cancer: a perspective from the Korean Integrative Cancer Center. Journal of biomedicine & biotechnology. 2012; 2012(?):874276. doi: 10.1155/2012/874276. [PMID: 22174564]
  • Sanja Matic, Snezana Stanic, Desanka Bogojevic, Slavica Solujic, Nevena Grdovic, Melita Vidakovic, Mirjana Mihailovic. Genotoxic potential of Cotinus coggygria Scop. (Anacardiaceae) stem extract in vivo. Genetics and molecular biology. 2011 Apr; 34(2):298-303. doi: 10.1590/s1415-47572011005000001. [PMID: 21734833]
  • Pilar Puebla, Yoko Oshima-Franco, Luiz M Franco, Marcio G Dos Santos, Renata V da Silva, Leandro Rubem-Mauro, Arturo San Feliciano. Chemical constituents of the bark of Dipteryx alata vogel, an active species against Bothrops jararacussu venom. Molecules (Basel, Switzerland). 2010 Nov; 15(11):8193-204. doi: 10.3390/molecules15118193. [PMID: 21076386]
  • 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]
  • 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]
  • Ji Hye Kim, Chang Hwa Jung, Bo-Hyoung Jang, Ho Yeon Go, Jong-Hyeong Park, You-Kyung Choi, Seong Il Hong, Yong Cheol Shin, Seong-Gyu Ko. Selective cytotoxic effects on human cancer cell lines of phenolic-rich ethyl-acetate fraction from Rhus verniciflua Stokes. The American journal of Chinese medicine. 2009; 37(3):609-20. doi: 10.1142/s0192415x09007090. [PMID: 19606519]
  • Eun Ha Lee, Dae-Geun Song, Joo Young Lee, Cheol-Ho Pan, Byung Hun Um, Sang Hoon Jung. Inhibitory effect of the compounds isolated from Rhus verniciflua on aldose reductase and advanced glycation endproducts. Biological & pharmaceutical bulletin. 2008 Aug; 31(8):1626-30. doi: 10.1248/bpb.31.1626. [PMID: 18670102]
  • Ai-Lin Liu, Hai-Di Wang, Simon MingYuen Lee, Yi-Tao Wang, Guan-Hua Du. Structure-activity relationship of flavonoids as influenza virus neuraminidase inhibitors and their in vitro anti-viral activities. Bioorganic & medicinal chemistry. 2008 Aug; 16(15):7141-7. doi: 10.1016/j.bmc.2008.06.049. [PMID: 18640042]
  • Chang Hwa Jung, Ji Hye Kim, Myung Hee Hong, Ho Moon Seog, Seong Hoon Oh, Pan Jae Lee, Gyung Jun Kim, Hyung Min Kim, Jae Young Um, Seong-Gyu Ko. Phenolic-rich fraction from Rhus verniciflua Stokes (RVS) suppress inflammatory response via NF-kappaB and JNK pathway in lipopolysaccharide-induced RAW 264.7 macrophages. Journal of ethnopharmacology. 2007 Apr; 110(3):490-7. doi: 10.1016/j.jep.2006.10.013. [PMID: 17112694]
  • Chang Hwa Jung, Chan-Yong Jun, Sundong Lee, Chong-Hyeong Park, Kiho Cho, Seong-Gyu Ko. Rhus verniciflua stokes extract: radical scavenging activities and protective effects on H2O2-induced cytotoxicity in macrophage RAW 264.7 cell lines. Biological & pharmaceutical bulletin. 2006 Aug; 29(8):1603-7. doi: 10.1248/bpb.29.1603. [PMID: 16880612]
  • Jian-fei Chao, Zhi-qi Yin, Wen-cai Ye, Shou-xun Zhao. [Chemical constituents from branch of Broussonetia papyrifera]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Jul; 31(13):1078-80. doi: ". [PMID: 17048607]
  • Monica Sanchez-Gonzalez, John P N Rosazza. Biocatalytic synthesis of butein and sulfuretin by Aspergillus alliaceus. Journal of agricultural and food chemistry. 2006 Jun; 54(13):4646-50. doi: 10.1021/jf060900k. [PMID: 16787010]
  • 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]
  • Hyon-Seok Jang, Sung-Ho Kook, Young-Ok Son, Jong-Ghee Kim, Young-Mi Jeon, Yong-Suk Jang, Ki-Choon Choi, Ju Kim, Seong-Kyu Han, Kyung-Yeol Lee, Byung-Keon Park, Nam-Pyo Cho, Jeong-Chae Lee. Flavonoids purified from Rhus verniciflua Stokes actively inhibit cell growth and induce apoptosis in human osteosarcoma cells. Biochimica et biophysica acta. 2005 Nov; 1726(3):309-16. doi: 10.1016/j.bbagen.2005.08.010. [PMID: 16213662]
  • J-C Lee, K-Y Lee, J Kim, C-S Na, N-C Jung, G-H Chung, Y-S Jang. Extract from Rhus verniciflua Stokes is capable of inhibiting the growth of human lymphoma cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2004 Sep; 42(9):1383-8. doi: 10.1016/j.fct.2004.03.012. [PMID: 15234068]
  • Kun-Young Park, Geun-Ok Jung, Kyung-Tae Lee, Jongwon Choi, Moo-Young Choi, Gab-Tae Kim, Hyun-Ju Jung, Hee-Juhn Park. Antimutagenic activity of flavonoids from the heartwood of Rhus verniciflua. Journal of ethnopharmacology. 2004 Jan; 90(1):73-9. doi: 10.1016/j.jep.2003.09.043. [PMID: 14698512]
  • Jongwon Choi, Byung-Jae Yoon, Yong Nam Han, Kyung-Tae Lee, Joohun Ha, Hyun-Ju Jung, Hee-Juhn Park. Antirheumatoid arthritis effect of Rhus verniciflua and of the active component, sulfuretin. Planta medica. 2003 Oct; 69(10):899-904. doi: 10.1055/s-2003-45097. [PMID: 14648391]
  • Mee Jung Jung, Hae Young Chung, Sam Sik Kang, Jin Ho Choi, Kae Sun Bae, Jae Sue Choi. Antioxidant activity from the stem bark of Albizzia julibrissin. Archives of pharmacal research. 2003 Jun; 26(6):458-62. doi: 10.1007/bf02976862. [PMID: 12877554]
  • Jeong-Chae Lee, Kye-Taek Lim, Yong-Suk Jang. Identification of Rhus verniciflua Stokes compounds that exhibit free radical scavenging and anti-apoptotic properties. Biochimica et biophysica acta. 2002 Apr; 1570(3):181-91. doi: 10.1016/s0304-4165(02)00196-4. [PMID: 12020808]
  • O Kayser, W R Waters, K M Woods, S J Upton, J S Keithly, A F Kiderlen. Evaluation of in vitro activity of aurones and related compounds against Cryptosporidium parvum. Planta medica. 2001 Nov; 67(8):722-5. doi: 10.1055/s-2001-18357. [PMID: 11731913]
  • J M Pinedo, F Gonzalez de Canales, J L Hinojosa, P Llamas, B M Hausen. Contact dermatitis to sesquiterpene lactones in Inula viscosa Aiton. Contact dermatitis. 1987 Nov; 17(5):322-3. doi: 10.1111/j.1600-0536.1987.tb01492.x. [PMID: 3325222]