Butein (BioDeep_00000000478)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


2 inverted exclamation mark ,3,4,4 inverted exclamation mark -tetrahydroxy Chalcone

化学式: C15H12O5 (272.0684702)
中文名称: 紫柳花素, 紫铆花素, 紫铆因, 紫铆查尔酮
谱图信息: 最多检出来源 Viridiplantae(plant) 1.12%

分子结构信息

SMILES: C1(O)=CC=C(C(=O)/C=C/C2C=CC(O)=C(O)C=2)C(O)=C1
InChI: InChI=1S/C15H12O5/c16-10-3-4-11(14(19)8-10)12(17)5-1-9-2-6-13(18)15(20)7-9/h1-8,16,18-20H/b5-1+

描述信息

Butein is a chalcone that is (E)-chalcone bearing four additional hydroxy substituents at positions 2, 3, 4 and 4. It has a role as a tyrosine kinase inhibitor, an antioxidant, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an antineoplastic agent, a geroprotector, a radiosensitizing agent, a hypoglycemic agent and a plant metabolite. It is a member of chalcones and a polyphenol.
Butein is a natural product found in Dahlia pinnata, Calanticaria bicolor, and other organisms with data available.
Butein is a flavonoid obtained from the seed of Cyclopia subternata. It is a specific protein tyrosine kinase inhibitor that induces apoptosis. (NCI)
See also: Semecarpus anacardium juice (part of).
A chalcone that is (E)-chalcone bearing four additional hydroxy substituents at positions 2, 3, 4 and 4.
C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor
Butein, also known as 2,3,4,4-tetrahydroxychalcone, is a member of the class of compounds known as 2-hydroxychalcones. 2-hydroxychalcones are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2-position. Thus, butein is considered to be a flavonoid lipid molecule. Butein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Butein is a bitter tasting compound found in broad bean, which makes butein a potential biomarker for the consumption of this food product. Butein is a chalcone of the chalconoids. It can be found in Toxicodendron vernicifluum (or formerly Rhus verniciflua), Dahlia, Butea (Butea monosperma) and Coreopsis It has antioxidative, aldose reductase and advanced glycation endproducts inhibitory effects. It is also a sirtuin-activating compound, a chemical compound having an effect on sirtuins, a group of enzymes that use NAD+ to remove acetyl groups from proteins. It turned out that buteins possess a high ability to inhibit aromatase process in the human body, for this reason, the use of these compounds in the treatment of breast cancer on the estrogen ground has been taken into account. The first attempts of sport pro-hormone supplementation with the use of buteins took place in Poland .
Butein is a cAMP-specific PDE inhibitor with an IC50 of 10.4 μM for PDE4[1]. Butein is a specific protein tyrosine kinase inhibitor with IC50s of 16 and 65 μM for EGFR and p60c-src in HepG2 cells[2]. Butein sensitizes HeLa cells to Cisplatin through AKT and ERK/p38 MAPK pathways by targeting FoxO3a[3]. Butein is a SIRT1 activator (STAC).
Butein is a cAMP-specific PDE inhibitor with an IC50 of 10.4 μM for PDE4[1]. Butein is a specific protein tyrosine kinase inhibitor with IC50s of 16 and 65 μM for EGFR and p60c-src in HepG2 cells[2]. Butein sensitizes HeLa cells to Cisplatin through AKT and ERK/p38 MAPK pathways by targeting FoxO3a[3]. Butein is a SIRT1 activator (STAC).

同义名列表

54 个代谢物同义名

2 inverted exclamation mark ,3,4,4 inverted exclamation mark -tetrahydroxy Chalcone; 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-, (2E)-; 2-Propen-1-one,1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-, (2E)-; 2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(3,4-DIHYDROXYPHENYL)-, (E)-; (2E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one; (2E)-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one; (E)-1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one; (E)-1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one; 2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-; 2-Propen-1-one,1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-; (E)-3-(3,4-Dihydroxy-phenyl)-1-(2,4-dihydroxy-phenyl)-propenone; 1-(2,4-Dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one; 3-(3,4-Dihydroxy-phenyl)-1-(2,4-dihydroxy-phenyl)-propenone; Acrylophenone, 2,4-dihydroxy-3-(3,4-dihydroxyphenyl)-; Chalcone, 2,3,4,4-tetrahydroxy-(7CI,8CI); 2,3,4,4-Tetrahydroxychalcone; Butein; (E)-2,3,4,4-terahydroxychalcone; Chalcone, 2,3,4,4-tetrahydroxy-; ISOLIQUIRITIGENIN METABOLITE M4; TETRAHYDROXYCHALCONE, 3,4,2,4-; 2,3,4,4-tetrahydroxy Chalcone; 2,3,4,4-Tetrahydroxy-chalcone; 3,4,2,4-Tetrahydroxychalcone; 2,4,3,4-tetrahydroxychalcone; 2,3,4,4-tetrahydroxychalcone; 3,4,2,4-tetrahydroxychalone; 3,4,2,4-Tetrahydroxychalone; Butein, analytical standard; UNII-4WVS5M0LGF; Butein, solid; LAVENDUSTINC; HSCI1_000162; 4WVS5M0LGF; AC1NQY7L; Butein; 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one; Chalcone, 2,3,4,4-tetrahydroxy- (7CI,8CI); 2′,3,4,4′-Tetrahydroxychalcone; 2′,4′,3,4-Tetrahydroxychalcone; 2,3,4,4-Tetrahydrochalcone; EINECS 207-659-5; NCGC00163519-01; MolMap_000005; NCI60_018489; AIDS-057944; B178_SIGMA; 21849-70-7; AIDS057944; ST5331397; NSC652892; 487-52-5; C08578; (E) -1- (2,4-Dihydroxyphenyl) -3- (3,4-dihydroxyphenyl) -2-propen-1-one; 2’,3,4,4’-tetrahydroxy Chalcone



数据库引用编号

26 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

6 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(3)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

187 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

  • Mujeeba Rehman, Rishabh Chaudhary, Sonu Rajput, Vipul Agarwal, Arjun Singh Kaushik, Siddhi Srivastava, Sukriti Srivastava, Rohit Singh, Irfan Aziz, Sanjay Singh, Vikas Mishra. Butein ameliorates chronic stress induced atherosclerosis via targeting anti-inflammatory, anti-fibrotic and BDNF pathways. Physiology & behavior. 2023 Apr; 267(?):114207. doi: 10.1016/j.physbeh.2023.114207. [PMID: 37100219]
  • Somayeh Mahdinloo, Salar Hemmati, Hadi Valizadeh, Mohammad Mahmoudian, Javad Mahmoudi, Leyla Roshangar, Muhammad Sarfraz, Parvin Zakeri-Milani. Synthesis and preparation of vitamin A coupled butein-loaded solid lipid nanoparticles for liver fibrosis therapy in rats. International journal of pharmaceutics. 2022 Sep; 625(?):122063. doi: 10.1016/j.ijpharm.2022.122063. [PMID: 35964827]
  • Pei Zhang, Jiale Zhang, Huahong Quan, Pengtao Chen, Jingcheng Wang, Yuan Liang. Effects of butein on human osteosarcoma cell proliferation, apoptosis, and autophagy through oxidative stress. Human & experimental toxicology. 2022 Jan; 41(?):9603271221074346. doi: 10.1177/09603271221074346. [PMID: 35130734]
  • Peng Liu, Quanli Pan. Butein Inhibits Oxidative Stress Injury in Rats with Chronic Heart Failure via ERK/Nrf2 Signaling. Cardiovascular therapeutics. 2022; 2022(?):8684014. doi: 10.1155/2022/8684014. [PMID: 35069800]
  • Jaeyool Jang, Seo-Hyuk Chang, Dawoon Song, No-Joon Song, Saeroarum Han, Seungjun Oh, Ui Jeong Yun, Jee-Yin Ahn, Sukchan Lee, Jin-Mo Ku, Kye Won Park. Butein-Enriched Fractions of Butea monosperma (Lam.) Taub. Flower Decrease Weight Gains and Increase Energy Expenditure in High-Fat Diet-Induced Obese Mice. Journal of medicinal food. 2021 Dec; 24(12):1271-1279. doi: 10.1089/jmf.2021.k.0074. [PMID: 34847724]
  • Hardeep Singh Tuli, Ruchira Joshi, Diwakar Aggarwal, Ginpreet Kaur, Jagjit Kaur, Manoj Kumar, Nidarshana Chaturvedi Parashar, Md Asaduzzaman Khan, Katrin Sak. Molecular mechanisms underlying chemopreventive potential of butein: Current trends and future perspectives. Chemico-biological interactions. 2021 Dec; 350(?):109699. doi: 10.1016/j.cbi.2021.109699. [PMID: 34648814]
  • Mehmet Akif Ramazanoglu, Tuncay Toprak, Mehmet Remzi Erdem, Gulistan Gumrukcu, Hatice Kucuk, Feridun Sengor. Effects of butein on renal ischemia/reperfusion injury: An experimental study. Archivio italiano di urologia, andrologia : organo ufficiale [di] Societa italiana di ecografia urologica e nefrologica. 2020 Dec; 92(4):. doi: 10.4081/aiua.2020.4.335. [PMID: 33348962]
  • Renalison Farias-Pereira, Zhenyu Zhang, Cheon-Seok Park, Daeyoung Kim, Kee-Hong Kim, Yeonhwa Park. Butein inhibits lipogenesis in Caenorhabditis elegans. BioFactors (Oxford, England). 2020 Sep; 46(5):777-787. doi: 10.1002/biof.1667. [PMID: 32663368]
  • D Sathya Prabhu, V Devi Rajeswari. PPAR-Gamma as putative gene target involved in Butein mediated anti-diabetic effect. Molecular biology reports. 2020 Jul; 47(7):5273-5283. doi: 10.1007/s11033-020-05605-1. [PMID: 32642916]
  • Basem M Abdallah, Enas M Ali. Butein Promotes Lineage Commitment of Bone Marrow-Derived Stem Cells into Osteoblasts via Modulating ERK1/2 Signaling Pathways. Molecules (Basel, Switzerland). 2020 Apr; 25(8):. doi: 10.3390/molecules25081885. [PMID: 32325749]
  • Bianca Hemmeryckx, Christine Vranckx, Dries Bauters, H Roger Lijnen, Ilse Scroyen. Does butein affect adipogenesis?. Adipocyte. 2019 12; 8(1):209-222. doi: 10.1080/21623945.2019.1617619. [PMID: 31094273]
  • 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]
  • C Zhang, X Zong, Y Han. Effect of butein and glucose on oxidative stress and p38 activation marker in non-small cell lung cancer cell. Human & experimental toxicology. 2019 Oct; 38(10):1155-1167. doi: 10.1177/0960327119851250. [PMID: 31215238]
  • D Sathya Prabhu, V Devi Rajeswari. In vitro and in silico analyses of Vicia faba L. on Peroxisome proliferator-activated receptor gamma. Journal of cellular biochemistry. 2018 09; 119(9):7729-7737. doi: 10.1002/jcb.27123. [PMID: 29923224]
  • Ghedeir M Alshammari, Aristatile Balakrishnan, Thirunavukkarasu Chinnasamy. Butein protects the nonalcoholic fatty liver through mitochondrial reactive oxygen species attenuation in rats. BioFactors (Oxford, England). 2018 May; 44(3):289-298. doi: 10.1002/biof.1428. [PMID: 29672963]
  • Chie Ishikawa, Masachika Senba, Naoki Mori. Butein inhibits NF-κB, AP-1 and Akt activation in adult T-cell leukemia/lymphoma. International journal of oncology. 2017 Aug; 51(2):633-643. doi: 10.3892/ijo.2017.4026. [PMID: 28586006]
  • 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]
  • Ganesan Padmavathi, Nand Kishor Roy, Devivasha Bordoloi, Frank Arfuso, Srishti Mishra, Gautam Sethi, Anupam Bishayee, Ajaikumar B Kunnumakkara. Butein in health and disease: A comprehensive review. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Feb; 25(?):118-127. doi: 10.1016/j.phymed.2016.12.002. [PMID: 28190465]
  • Hyeong Sim Choi, Min Kyoung Kim, Youn Kyung Choi, Yong Cheol Shin, Sung-Gook Cho, Seong-Gyu Ko. Rhus verniciflua Stokes (RVS) and butein induce apoptosis of paclitaxel-resistant SKOV-3/PAX ovarian cancer cells through inhibition of AKT phosphorylation. BMC complementary and alternative medicine. 2016 Apr; 16(?):122. doi: 10.1186/s12906-016-1103-3. [PMID: 27121110]
  • Christian Molitor, Stephan Gerhard Mauracher, Annette Rompel. Aurone synthase is a catechol oxidase with hydroxylase activity and provides insights into the mechanism of plant polyphenol oxidases. Proceedings of the National Academy of Sciences of the United States of America. 2016 Mar; 113(13):E1806-15. doi: 10.1073/pnas.1523575113. [PMID: 26976571]
  • Mahmut Toprak. Fluorescence study on the interaction of human serum albumin with Butein in liposomes. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2016 Feb; 154(?):108-113. doi: 10.1016/j.saa.2015.10.023. [PMID: 26519918]
  • Ziwei Song, Muthu K Shanmugam, Hanry Yu, Gautam Sethi. Butein and Its Role in Chronic Diseases. Advances in experimental medicine and biology. 2016; 928(?):419-433. doi: 10.1007/978-3-319-41334-1_17. [PMID: 27671826]
  • Cornelia Kaintz, Rupert L Mayer, Franz Jirsa, Heidi Halbwirth, Annette Rompel. Site-directed mutagenesis around the CuA site of a polyphenol oxidase from Coreopsis grandiflora (cgAUS1). FEBS letters. 2015 Mar; 589(7):789-97. doi: 10.1016/j.febslet.2015.02.009. [PMID: 25697959]
  • Pei-Yu Yang, Dan-Ning Hu, I-Ching Lin, Fu-Shing Liu. Butein Shows Cytotoxic Effects and Induces Apoptosis in Human Ovarian Cancer Cells. The American journal of Chinese medicine. 2015; 43(4):769-82. doi: 10.1142/s0192415x15500482. [PMID: 26119952]
  • 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]
  • 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]
  • 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]
  • Hai-tao Bian, Jun Zhao, Hua Huang, Qiao-li Yang, Yan Liu. [Chemical constituents from seeds of Sophora alopecuroides]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Jan; 37(1):72-3. doi: ". [PMID: 25090709]
  • Chul Lee, Jin Woo Lee, Qinghao Jin, Dae Sik Jang, Sung-Joon Lee, Dongho Lee, Jin Tae Hong, Youngsoo Kim, Mi Kyeong Lee, Bang Yeon Hwang. Inhibitory constituents of the heartwood of Dalbergia odorifera on nitric oxide production in RAW 264.7 macrophages. Bioorganic & medicinal chemistry letters. 2013 Jul; 23(14):4263-6. doi: 10.1016/j.bmcl.2013.04.032. [PMID: 23743282]
  • No-Joon Song, Hyang-Jin Yoon, Ki Hyun Kim, So-Ra Jung, Woo-Seok Jang, Cho-Rong Seo, Young Min Lee, Dae-Hyuk Kweon, Joung-Woo Hong, Jeong-Soo Lee, Ki-Moon Park, Kang Ro Lee, Kye Won Park. Butein is a novel anti-adipogenic compound. Journal of lipid research. 2013 May; 54(5):1385-96. doi: 10.1194/jlr.m035576. [PMID: 23468131]
  • Dong-Sung Lee, Bin Li, Kyoung-Su Kim, Gil-Saeng Jeong, Eun-Cheol Kim, Youn-Chul Kim. Butein protects human dental pulp cells from hydrogen peroxide-induced oxidative toxicity via Nrf2 pathway-dependent heme oxygenase-1 expressions. Toxicology in vitro : an international journal published in association with BIBRA. 2013 Mar; 27(2):874-81. doi: 10.1016/j.tiv.2013.01.003. [PMID: 23318726]
  • Anuradha Sehrawat, Vijay Kumar. Butein imparts free radical scavenging, anti-oxidative and proapoptotic properties in the flower extracts of Butea monosperma. Biocell : official journal of the Sociedades Latinoamericanas de Microscopia Electronica ... et. al. 2012 Aug; 36(2):63-71. doi: . [PMID: 23185781]
  • 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]
  • Naghma Khan, Vaqar M Adhami, Farrukh Afaq, Hasan Mukhtar. Butein induces apoptosis and inhibits prostate tumor growth in vitro and in vivo. Antioxidants & redox signaling. 2012 Jun; 16(11):1195-204. doi: 10.1089/ars.2011.4162. [PMID: 22114764]
  • 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]
  • Gabriele Multhoff, Jürgen Radons. Radiation, inflammation, and immune responses in cancer. Frontiers in oncology. 2012; 2(?):58. doi: 10.3389/fonc.2012.00058. [PMID: 22675673]
  • 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]
  • Lei Ma, Zhengyi Yang, Chenjing Li, Zhiyuan Zhu, Xu Shen, Lihong Hu. Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1). Journal of enzyme inhibition and medicinal chemistry. 2011 Oct; 26(5):643-8. doi: 10.3109/14756366.2010.543420. [PMID: 21222511]
  • Sho Ohno, Munetaka Hosokawa, Atsushi Hoshino, Yoshikuni Kitamura, Yasumasa Morita, Kyeung-Ii Park, Akiko Nakashima, Ayumi Deguchi, Fumi Tatsuzawa, Motoaki Doi, Shigeru Iida, Susumu Yazawa. A bHLH transcription factor, DvIVS, is involved in regulation of anthocyanin synthesis in dahlia (Dahlia variabilis). Journal of experimental botany. 2011 Oct; 62(14):5105-16. doi: 10.1093/jxb/err216. [PMID: 21765172]
  • Soon-Sen Leow, Shamala Devi Sekaran, Kalyana Sundram, YewAi Tan, Ravigadevi Sambanthamurthi. Differential transcriptomic profiles effected by oil palm phenolics indicate novel health outcomes. BMC genomics. 2011 Aug; 12(?):432. doi: 10.1186/1471-2164-12-432. [PMID: 21864415]
  • Elizabeth A Mazzio, Fran Close, Karam F A Soliman. The biochemical and cellular basis for nutraceutical strategies to attenuate neurodegeneration in Parkinson's disease. International journal of molecular sciences. 2011 Jan; 12(1):506-69. doi: 10.3390/ijms12010506. [PMID: 21340000]
  • Gil-Saeng Jeong, Dong-Sung Lee, Mi-Young Song, Byung-Hyun Park, Dae-Gill Kang, Ho-Sub Lee, Kang-Beom Kwon, Youn-Chul Kim. Butein from Rhus verniciflua protects pancreatic β cells against cytokine-induced toxicity mediated by inhibition of nitric oxide formation. Biological & pharmaceutical bulletin. 2011; 34(1):97-102. doi: 10.1248/bpb.34.97. [PMID: 21212525]
  • Karin Schlangen, Silvija Miosic, Jana Thill, Heidi Halbwirth. Cloning, functional expression, and characterization of a chalcone 3-hydroxylase from Cosmos sulphureus. Journal of experimental botany. 2010 Jul; 61(12):3451-9. doi: 10.1093/jxb/erq169. [PMID: 20566567]
  • 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]
  • Zafar Rasheed, Nahid Akhtar, Abubakar Khan, Khursheed A Khan, Tariq M Haqqi. Butrin, isobutrin, and butein from medicinal plant Butea monosperma selectively inhibit nuclear factor-kappaB in activated human mast cells: suppression of tumor necrosis factor-alpha, interleukin (IL)-6, and IL-8. The Journal of pharmacology and experimental therapeutics. 2010 May; 333(2):354-63. doi: 10.1124/jpet.109.165209. [PMID: 20164300]
  • Dae-Geun Song, Joo Young Lee, Eun Ha Lee, Sang Hoon Jung, Chu Won Nho, Kwang Hyun Cha, Song Yi Koo, Cheol-Ho Pan. Inhibitory effects of polyphenols isolated from Rhus verniciflua on Aldo-keto reductase family 1 B10. BMB reports. 2010 Apr; 43(4):268-72. doi: 10.5483/bmbrep.2010.43.4.268. [PMID: 20423612]
  • E Paul Cherniack. The potential influence of plant polyphenols on the aging process. Forschende Komplementarmedizin (2006). 2010; 17(4):181-7. doi: 10.1159/000319143. [PMID: 20829595]
  • Zafar Rasheed, Nahid Akhtar, Tariq M Haqqi. Pomegranate extract inhibits the interleukin-1β-induced activation of MKK-3, p38α-MAPK and transcription factor RUNX-2 in human osteoarthritis chondrocytes. Arthritis research & therapy. 2010; 12(5):R195. doi: 10.1186/ar3166. [PMID: 20955562]
  • Mona Semalty, Ajay Semalty, Ashutosh Badola, Geeta Pant Joshi, M S M Rawat. Semecarpus anacardium Linn.: A review. Pharmacognosy reviews. 2010 Jan; 4(7):88-94. doi: 10.4103/0973-7847.65328. [PMID: 22228947]
  • Xiao-Yu Wang, Hai-Ming Shi, Li Zhang, Xiao-Bo Li. A new chalcone glycoside, a new tetrahydrofuranoid lignan, and antioxidative constituents from the stems and leaves of Viburnum propinquum. Planta medica. 2009 Sep; 75(11):1262-5. doi: 10.1055/s-0029-1185523. [PMID: 19330766]
  • Zengbao Wu, Bin Wang, Yuying Zhao, Xiuwei Yang, Hong Liang. [Chalcones from Bauhinia glauca subsp. pernervosa]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Jul; 34(13):1676-8. doi: ". [PMID: 19873779]
  • 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]
  • Guiyun Wang, Chao Ma. [Studies on phenolic compounds from Sophora alopecuroides]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 May; 34(10):1238-40. doi: ". [PMID: 19673386]
  • 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]
  • Preetha Anand, Ajaikumar B Kunnumakkara, Ajaikumar B Kunnumakara, Chitra Sundaram, Kuzhuvelil B Harikumar, Sheeja T Tharakan, Oiki S Lai, Bokyung Sung, Bharat B Aggarwal. Cancer is a preventable disease that requires major lifestyle changes. Pharmaceutical research. 2008 Sep; 25(9):2097-116. doi: 10.1007/s11095-008-9661-9. [PMID: 18626751]
  • 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]
  • 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]
  • Alistair K Brown, Athina Papaemmanouil, Veemal Bhowruth, Apoorva Bhatt, Lynn G Dover, Gurdyal S Besra. Flavonoid inhibitors as novel antimycobacterial agents targeting Rv0636, a putative dehydratase enzyme involved in Mycobacterium tuberculosis fatty acid synthase II. Microbiology (Reading, England). 2007 Oct; 153(Pt 10):3314-3322. doi: 10.1099/mic.0.2007/009936-0. [PMID: 17906131]
  • So-Yeon Kim, Eun-Jeon Park, Yu-Zhe Zhao, Dong Hwan Sohn. Butein suppresses bile acid-induced hepatocyte apoptosis through a JNK-dependent but ERK-independent pathway. Planta medica. 2007 Jul; 73(8):777-81. doi: 10.1055/s-2007-981547. [PMID: 17592815]
  • Manoj K Pandey, Santosh K Sandur, Bokyung Sung, Gautam Sethi, Ajaikumar B Kunnumakkara, Bharat B Aggarwal. Butein, a tetrahydroxychalcone, inhibits nuclear factor (NF)-kappaB and NF-kappaB-regulated gene expression through direct inhibition of IkappaBalpha kinase beta on cysteine 179 residue. The Journal of biological chemistry. 2007 Jun; 282(24):17340-50. doi: 10.1074/jbc.m700890200. [PMID: 17439942]
  • 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]
  • Shailendra Kumar Sharma, Prasanna Parasuraman, Gyanendra Kumar, Namita Surolia, Avadhesha Surolia. Green tea catechins potentiate triclosan binding to enoyl-ACP reductase from Plasmodium falciparum (PfENR). Journal of medicinal chemistry. 2007 Feb; 50(4):765-75. doi: 10.1021/jm061154d. [PMID: 17263522]
  • James David Adams, Rubin Wang, Jun Yang, Eric Jungchi Lien. Preclinical and clinical examinations of Salvia miltiorrhiza and its tanshinones in ischemic conditions. Chinese medicine. 2006 Nov; 1(?):3. doi: 10.1186/1749-8546-1-3. [PMID: 17302964]
  • 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]
  • 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]
  • Yun Wang, Franky L Chan, Shiuan Chen, Lai K Leung. The plant polyphenol butein inhibits testosterone-induced proliferation in breast cancer cells expressing aromatase. Life sciences. 2005 May; 77(1):39-51. doi: 10.1016/j.lfs.2004.12.014. [PMID: 15848217]
  • Michael Samoszuk, Jenny Tan, Guillaume Chorn. The chalcone butein from Rhus verniciflua Stokes inhibits clonogenic growth of human breast cancer cells co-cultured with fibroblasts. BMC complementary and alternative medicine. 2005 Mar; 5(?):5. doi: 10.1186/1472-6882-5-5. [PMID: 15757513]
  • 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]
  • Hyun-Mi Kang, Jong-Han Kim, Mi-Young Lee, Kwang-Hee Son, Deok Cho Yang, Nam-In Baek, Byoung-Mog Kwon. Relationship between flavonoid structure and inhibition of farnesyl protein transferase. Natural product research. 2004 Aug; 18(4):349-56. doi: 10.1080/14786410310001622022. [PMID: 15214488]
  • C Selvam, Sanjay M Jachak, K K Bhutani. Cyclooxygenase inhibitory flavonoids from the stem bark of Semecarpus anacardium Linn. Phytotherapy research : PTR. 2004 Jul; 18(7):582-4. doi: 10.1002/ptr.1492. [PMID: 15305321]
  • Dae Gill Kang, An Sook Lee, Yeun Ja Mun, Won Hong Woo, Youn Chul Kim, Eun Jin Sohn, Mi Kyong Moon, Ho Sub Lee. Butein ameliorates renal concentrating ability in cisplatin-induced acute renal failure in rats. Biological & pharmaceutical bulletin. 2004 Mar; 27(3):366-70. doi: 10.1248/bpb.27.366. [PMID: 14993804]
  • Hye Won Lee, Hye Young Ji, Hong Il Lee, Hae-Kyoung Kim, Dong Hwan Sohn, Youn-Chul Kim, Hun Taeg Chung, Hye Suk Lee. Determination of butein in rat serum by high performance liquid chromatography. Journal of pharmaceutical and biomedical analysis. 2004 Jan; 34(1):227-31. doi: 10.1016/j.japna.2003.08.004. [PMID: 14738938]
  • LiLi Zhu, Lirong Chen, Xiaojie Xu. Application of a molecularly imprinted polymer for the effective recognition of different anti-epidermal growth factor receptor inhibitors. Analytical chemistry. 2003 Dec; 75(23):6381-7. doi: 10.1021/ac026371a. [PMID: 14640704]
  • Sung Hee Lee, Ji-Xing Nan, Yu Zhe Zhao, Sun Wook Woo, Eun-Jeon Park, Tai-Hyun Kang, Geom Seog Seo, Youn-Chul Kim, Dong Hwan Sohn. The chalcone butein from Rhus verniciflua shows antifibrogenic activity. Planta medica. 2003 Nov; 69(11):990-4. doi: 10.1055/s-2003-45143. [PMID: 14735434]
  • Dae Gill Kang, Yun Cheol Kim, Eun Jin Sohn, Yun Mi Lee, An Sook Lee, Ming Hao Yin, Ho Sub Lee. Hypotensive effect of butein via the inhibition of angiotensin converting enzyme. Biological & pharmaceutical bulletin. 2003 Sep; 26(9):1345-7. doi: 10.1248/bpb.26.1345. [PMID: 12951484]
  • Jiao Shi, Bo Chen, Zhi-hua Sun, Chang-qi Hu. [Studies on flavonoid constituents of Caragana intermediia]. Yao xue xue bao = Acta pharmaceutica Sinica. 2003 Aug; 38(8):599-602. doi: ". [PMID: 14628451]
  • Kai Zhang, Kim Ping Wong, Pierce Chow. Conjugation of chlorambucil with GSH by GST purified from human colon adenocarcinoma cells and its inhibition by plant polyphenols. Life sciences. 2003 Apr; 72(23):2629-40. doi: 10.1016/s0024-3205(03)00173-5. [PMID: 12672508]
  • Lili Zhu, Xiaojie Xu. Selective separation of active inhibitors of epidermal growth factor receptor from Caragana jubata by molecularly imprinted solid-phase extraction. Journal of chromatography. A. 2003 Apr; 991(2):151-8. doi: 10.1016/s0021-9673(03)00207-3. [PMID: 12741595]
  • 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]
  • N Y Kim, H O Pae, G S Oh, T H Kang, Y C Kim, H Y Rhew, H T Chung. Butein, a plant polyphenol, induces apoptosis concomitant with increased caspase-3 activity, decreased Bcl-2 expression and increased Bax expression in HL-60 cells. Pharmacology & toxicology. 2001 May; 88(5):261-6. doi: 10.1034/j.1600-0773.2001.d01-114.x. [PMID: 11393587]
  • Z J Cheng, S C Kuo, S C Chan, F N Ko, C M Teng. Antioxidant properties of butein isolated from Dalbergia odorifera. Biochimica et biophysica acta. 1998 Jun; 1392(2-3):291-9. doi: 10.1016/s0005-2760(98)00043-5. [PMID: 9630680]
  • E B Yang, K Zhang, L Y Cheng, P Mack. Butein, a specific protein tyrosine kinase inhibitor. Biochemical and biophysical research communications. 1998 Apr; 245(2):435-8. doi: 10.1006/bbrc.1998.8452. [PMID: 9571170]
  • K Zhang, K P Wong. Inhibition of the efflux of glutathione S-conjugates by plant polyphenols. Biochemical pharmacology. 1996 Nov; 52(10):1631-8. doi: 10.1016/s0006-2952(96)00570-9. [PMID: 8937479]
  • K Hayashi, T Nagamatsu, S Honda, Y Suzuki. Butein ameliorates experimental anti-glomerular basement membrane (GBM) antibody-associated glomerulonephritis in rats (1). Japanese journal of pharmacology. 1996 Jan; 70(1):55-64. doi: 10.1254/jjp.70.55. [PMID: 8822089]
  • C C Yit, N P Das. Cytotoxic effect of butein on human colon adenocarcinoma cell proliferation. Cancer letters. 1994 Jul; 82(1):65-72. doi: 10.1016/0304-3835(94)90147-3. [PMID: 8033070]
  • S Sogawa, Y Nihro, H Ueda, T Miki, H Matsumoto, T Satoh. Protective effects of hydroxychalcones on free radical-induced cell damage. Biological & pharmaceutical bulletin. 1994 Feb; 17(2):251-6. doi: 10.1248/bpb.17.251. [PMID: 8205123]
  • S Sogawa, Y Nihro, H Ueda, A Izumi, T Miki, H Matsumoto, T Satoh. 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors. Journal of medicinal chemistry. 1993 Nov; 36(24):3904-9. doi: 10.1021/jm00076a019. [PMID: 8254620]
  • R Ramanathan, C H Tan, N P Das. Cytotoxic effect of plant polyphenols and fat-soluble vitamins on malignant human cultured cells. Cancer letters. 1992 Mar; 62(3):217-24. doi: 10.1016/0304-3835(92)90099-h. [PMID: 1596866]
  • S Brown, L A Griffiths. Metabolism and excretion of butein, 2',3,4-trihydroxychalcone, 3-O-methylbutein, 4-O-methylbutein and 2',4',4-trihydroxychalcone in the rat. Xenobiotica; the fate of foreign compounds in biological systems. 1983 Nov; 13(11):669-82. doi: 10.3109/00498258309052228. [PMID: 6673378]