Sinensetin (BioDeep_00000270731)

Main id: BioDeep_00000003832

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-

化学式: C20H20O7 (372.120897)
中文名称: 甜橙黄酮
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c(C(=O)1)(c3OC)c(cc(c3OC)OC)OC(c(c2)cc(c(c2)OC)OC)=C1
InChI: InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3



数据库引用编号

15 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)

69 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

  • Yanhong Sun, Xiaoyan Duan, Fenghe Wang, Huixin Tan, Jiahuan Hu, Wanting Bai, Xinbo Wang, Baolian Wang, Jinping Hu. Inhibitory effects of flavonoids on glucose transporter 1 (GLUT1): From library screening to biological evaluation to structure-activity relationship. Toxicology. 2023 Mar; ?(?):153475. doi: 10.1016/j.tox.2023.153475. [PMID: 36870413]
  • Xiaoqi Wang, Dongli Li, Yong Cao, Chi-Tang Ho, Qingrong Huang. Biotransformation and Quantification of Sinensetin and Its Metabolites in Plasma, Urine, and Feces of Rats. Journal of agricultural and food chemistry. 2021 Dec; 69(47):14143-14150. doi: 10.1021/acs.jafc.1c05024. [PMID: 34797063]
  • Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach. European journal of medicinal chemistry. 2021 Mar; 213(?):113037. doi: 10.1016/j.ejmech.2020.113037. [PMID: 33257172]
  • Dan Liu, Xiangyu Cao, Yuchi Kong, Teng Mu, Jianli Liu. Inhibitory mechanism of sinensetin on α-glucosidase and non-enzymatic glycation: Insights from spectroscopy and molecular docking analyses. International journal of biological macromolecules. 2021 Jan; 166(?):259-267. doi: 10.1016/j.ijbiomac.2020.10.174. [PMID: 33115652]
  • Fahrauk Faramayuda, Totik Sri Mariani, Elfahmi, Sukrasno. Micropropagation and Secondary Metabolites Content of White-Purple Varieties of Orthosiphon aristatus Blume Miq. Pakistan journal of biological sciences : PJBS. 2021 Jan; 24(8):858-867. doi: 10.3923/pjbs.2021.858.867. [PMID: 34486353]
  • Jianwei Chen, Yaojia Lu, Xinyi Ye, Mahmoud Emam, Huawei Zhang, Hong Wang. Current advances in Vibrio harveyi quorum sensing as drug discovery targets. European journal of medicinal chemistry. 2020 Dec; 207(?):112741. doi: 10.1016/j.ejmech.2020.112741. [PMID: 32871343]
  • Seong Min Kim, Sang Eun Ha, Ho Jeong Lee, Shailima Rampogu, Preethi Vetrivel, Hun Hwan Kim, Venu Venkatarame Gowda Saralamma, Keun Woo Lee, Gon Sup Kim. Sinensetin Induces Autophagic Cell Death through p53-Related AMPK/mTOR Signaling in Hepatocellular Carcinoma HepG2 Cells. Nutrients. 2020 Aug; 12(8):. doi: 10.3390/nu12082462. [PMID: 32824273]
  • Xiaoqing Fan, Jie Bai, Minwan Hu, Yanxia Xu, Shengyu Zhao, Yanhong Sun, Baolian Wang, Jinping Hu, Yan Li. Drug interaction study of flavonoids toward OATP1B1 and their 3D structure activity relationship analysis for predicting hepatoprotective effects. Toxicology. 2020 05; 437(?):152445. doi: 10.1016/j.tox.2020.152445. [PMID: 32259555]
  • Jiashun Li, Xiang Jie, Xiaoli Liang, Ziyu Chen, Peifang Xie, Xiping Pan, Beixian Zhou, Jing Li. Sinensetin suppresses influenza a virus-triggered inflammation through inhibition of NF-κB and MAPKs signalings. BMC complementary medicine and therapies. 2020 May; 20(1):135. doi: 10.1186/s12906-020-02918-3. [PMID: 32370749]
  • Angela Bisio, Anna M Schito, Francesca Pedrelli, Ombeline Danton, Jakob K Reinhardt, Giulio Poli, Tiziano Tuccinardi, Thomas Bürgi, Francesco De Riccardis, Mauro Giacomini, Daniela Calzia, Isabella Panfoli, Gian Carlo Schito, Matthias Hamburger, Nunziatina De Tommasi. Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana. Journal of natural products. 2020 04; 83(4):1027-1042. doi: 10.1021/acs.jnatprod.9b01024. [PMID: 32182064]
  • Melanie Deipenbrock, Andreas Hensel. Polymethoxylated flavones from Orthosiphon stamineus leaves as antiadhesive compounds against uropathogenic E. coli. Fitoterapia. 2019 Nov; 139(?):104387. doi: 10.1016/j.fitote.2019.104387. [PMID: 31678632]
  • Yong-Jian Xiong, Zhao-Bin Deng, Jia-Ni Liu, Juan-Juan Qiu, Li Guo, Pan-Pan Feng, Jing-Ru Sui, Da-Peng Chen, Hui-Shu Guo. Enhancement of epithelial cell autophagy induced by sinensetin alleviates epithelial barrier dysfunction in colitis. Pharmacological research. 2019 10; 148(?):104461. doi: 10.1016/j.phrs.2019.104461. [PMID: 31542404]
  • Yin Xu, Xiaojian Lv, Guliang Yang, Jianfeng Zhan, Ming Li, Tao Long, Chi-Tang Ho, Shiming Li. Simultaneous separation of six pure polymethoxyflavones from sweet orange peel extract by high performance counter current chromatography. Food chemistry. 2019 Sep; 292(?):160-165. doi: 10.1016/j.foodchem.2019.04.031. [PMID: 31054661]
  • Huijuan Zhang, Guifang Tian, Chengying Zhao, Yanhui Han, Christina DiMarco-Crook, Chang Lu, Yuming Bao, Chengxiu Li, Hang Xiao, Jinkai Zheng. Characterization of polymethoxyflavone demethylation during drying processes of citrus peels. Food & function. 2019 Sep; 10(9):5707-5717. doi: 10.1039/c9fo01053j. [PMID: 31436765]
  • Jie Bai, Shengyu Zhao, Xiaoqing Fan, Yonghui Chen, Xiaowen Zou, Minwan Hu, Baolian Wang, Jing Jin, Xiaojian Wang, Jinping Hu, Dan Zhang, Yan Li. Inhibitory effects of flavonoids on P-glycoprotein in vitro and in vivo: Food/herb-drug interactions and structure-activity relationships. Toxicology and applied pharmacology. 2019 04; 369(?):49-59. doi: 10.1016/j.taap.2019.02.010. [PMID: 30790579]
  • Elena Roselló-Soto, Francisco J Martí-Quijal, Antonio Cilla, Paulo E S Munekata, Jose M Lorenzo, Fabienne Remize, Francisco J Barba. Influence of Temperature, Solvent and pH on the Selective Extraction of Phenolic Compounds from Tiger Nuts by-Products: Triple-TOF-LC-MS-MS Characterization. Molecules (Basel, Switzerland). 2019 Feb; 24(4):. doi: 10.3390/molecules24040797. [PMID: 30813299]
  • Vorapong Klungboonkrong, Buddhi P Lamsal, Singhanat Phoungchandang. Changes and degradation kinetics of some bioactive compounds in dried Orthosiphon aristatus (Java tea) leaves during elevated temperature storage. Journal of the science of food and agriculture. 2019 Jan; 99(2):933-940. doi: 10.1002/jsfa.9268. [PMID: 30009388]
  • Mun Fei Yam, Chu Shan Tan, Ruan Shibao. Vasorelaxant effect of sinensetin via the NO/sGC/cGMP pathway and potassium and calcium channels. Hypertension research : official journal of the Japanese Society of Hypertension. 2018 Oct; 41(10):787-797. doi: 10.1038/s41440-018-0083-8. [PMID: 30111856]
  • Stephen S Nyandoro, Joan J E Munissi, Msim Kombo, Clarence A Mgina, Fangfang Pan, Amra Gruhonjic, Paul Fitzpatrick, Yu Lu, Bin Wang, Kari Rissanen, Máté Erdélyi. Flavonoids from Erythrina schliebenii. Journal of natural products. 2017 02; 80(2):377-383. doi: 10.1021/acs.jnatprod.6b00839. [PMID: 28112509]
  • Yearam Jung, Soon Young Shin, Yeonjoong Yong, Hyeryoung Jung, Seunghyun Ahn, Young Han Lee, Yoongho Lim. Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chemical biology & drug design. 2015 May; 85(5):574-85. doi: 10.1111/cbdd.12445. [PMID: 25298094]
  • Seong-Il Kang, Hye-Sun Shin, Se-Jae Kim. Sinensetin enhances adipogenesis and lipolysis by increasing cyclic adenosine monophosphate levels in 3T3-L1 adipocytes. Biological & pharmaceutical bulletin. 2015; 38(4):552-8. doi: 10.1248/bpb.b14-00700. [PMID: 25735898]
  • Yan Pan, Kai Hung Tiong, Badrul Amini Abd-Rashid, Zakiah Ismail, Rusli Ismail, Joon Wah Mak, Chin Eng Ong. In vitro effect of important herbal active constituents on human cytochrome P450 1A2 (CYP1A2) activity. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Oct; 21(12):1645-50. doi: 10.1016/j.phymed.2014.08.003. [PMID: 25442272]
  • Guor-Jien Wei, Jenn-Feng Sheen, Wen-Chien Lu, Lucy Sun Hwang, Chi-Tang Ho, Ching-I Lin. Identification of sinensetin metabolites in rat urine by an isotope-labeling method and ultrahigh-performance liquid chromatography-electrospray ionization mass spectrometry. Journal of agricultural and food chemistry. 2013 May; 61(21):5016-21. doi: 10.1021/jf3046768. [PMID: 23647150]
  • Seong-Il Kang, Hye-Sun Shin, Hee-Chul Ko, Se-Jae Kim. Effects of sinensetin on lipid metabolism in mature 3T3-L1 adipocytes. Phytotherapy research : PTR. 2013 Jan; 27(1):131-4. doi: 10.1002/ptr.4683. [PMID: 22438091]
  • Saem Han, Hye Min Kim, Sanghyun Lee. Simultaneous determination of polymethoxyflavones in Citrus species, Kiyomi tangor and Satsuma mandarin, by high performance liquid chromatography. Food chemistry. 2012 Sep; 134(2):1220-4. doi: 10.1016/j.foodchem.2012.02.187. [PMID: 23107751]
  • Mun Fei Yam, Elsnoussi Ali Hussin Mohamed, Lee Fung Ang, Li Pei, Yusrida Darwis, Roziahanim Mahmud, Mohd Zaini Asmawi, Rusliza Basir, Mariam Ahmad. A simple isocratic HPLC method for the simultaneous determination of sinensetin, eupatorin, and 3'-hydroxy-5,6,7,4'-tetramethoxyflavone in Orthosiphon stamineus extracts. Journal of acupuncture and meridian studies. 2012 Aug; 5(4):176-82. doi: 10.1016/j.jams.2012.05.005. [PMID: 22898066]
  • Mirka Laavola, Riina Nieminen, Mun Fei Yam, Amirin Sadikun, Mohd Zaini Asmawi, Rusliza Basir, Jukka Welling, Heikki Vapaatalo, Riku Korhonen, Eeva Moilanen. Flavonoids eupatorin and sinensetin present in Orthosiphon stamineus leaves inhibit inflammatory gene expression and STAT1 activation. Planta medica. 2012 May; 78(8):779-86. doi: 10.1055/s-0031-1298458. [PMID: 22516932]
  • Yuguang Lin, Mario A Vermeer, Wil Bos, Leo van Buren, Eric Schuurbiers, Silvia Miret-Catalan, Elke A Trautwein. Molecular structures of citrus flavonoids determine their effects on lipid metabolism in HepG2 cells by primarily suppressing apoB secretion. Journal of agricultural and food chemistry. 2011 May; 59(9):4496-503. doi: 10.1021/jf1044475. [PMID: 21425871]
  • Yan Pan, Badrul Amini Abd-Rashid, Zakiah Ismail, Rusli Ismail, Joon Wah Mak, Peter C K Pook, Hui Meng Er, Chin Eng Ong. In vitro effects of active constituents and extracts of Orthosiphon stamineus on the activities of three major human cDNA-expressed cytochrome P450 enzymes. Chemico-biological interactions. 2011 Mar; 190(1):1-8. doi: 10.1016/j.cbi.2011.01.022. [PMID: 21276781]
  • Yang Dong, Guang Ji, Aili Cao, Jianrong Shi, Hailian Shi, Jianqun Xie, Dazheng Wu. [Effects of sinensetin on proliferation and apoptosis of human gastric cancer AGS cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Mar; 36(6):790-4. doi: . [PMID: 21710752]
  • H Muhammad, M R Gomes-Carneiro, K S Poça, A C A X De-Oliveira, A Afzan, S A Sulaiman, Z Ismail, F J R Paumgartten. Evaluation of the genotoxicity of Orthosiphon stamineus aqueous extract. Journal of ethnopharmacology. 2011 Jan; 133(2):647-53. doi: 10.1016/j.jep.2010.10.055. [PMID: 21044879]
  • 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]
  • Mohammed A Alshawsh, Mahmood Ameen Abdulla, Salmah Ismail, Zahra A Amin. Hepatoprotective Effects of Orthosiphon stamineus Extract on Thioacetamide-Induced Liver Cirrhosis in Rats. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):103039. doi: 10.1155/2011/103039. [PMID: 21647311]
  • Siddig Ibrahim Abdelwahab, Syam Mohan, Manal Mohamed Elhassan, Nabil Al-Mekhlafi, Abdelbasit Adam Mariod, Ahmad Bustamam Abdul, Mahmood Ameen Abdulla, Khalid M Alkharfy. Antiapoptotic and Antioxidant Properties of Orthosiphon stamineus Benth (Cat's Whiskers): Intervention in the Bcl-2-Mediated Apoptotic Pathway. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):156765. doi: 10.1155/2011/156765. [PMID: 21234328]
  • Saem Han, Hye Min Kim, Jeong Min Lee, So-Youn Mok, Sanghyun Lee. Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong. Journal of agricultural and food chemistry. 2010 Sep; 58(17):9488-91. doi: 10.1021/jf102730b. [PMID: 20698540]
  • Hana Kim, Jeong Yong Moon, Ashik Mosaddik, Somi Kim Cho. Induction of apoptosis in human cervical carcinoma HeLa cells by polymethoxylated flavone-rich Citrus grandis Osbeck (Dangyuja) leaf extract. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2010 Aug; 48(8-9):2435-42. doi: 10.1016/j.fct.2010.06.006. [PMID: 20538032]
  • Mun Fei Yam, Vuanghao Lim, Ibrahim Muhammad Salman, Omar Ziad Ameer, Lee Fung Ang, Noersal Rosidah, Muthanna Fawzy Abdulkarim, Ghassan Zuhair Abdullah, Rusliza Basir, Amirin Sadikun, Mohd Zaini Asmawi. HPLC and anti-inflammatory studies of the flavonoid rich chloroform extract fraction of Orthosiphon stamineus leaves. Molecules (Basel, Switzerland). 2010 Jun; 15(6):4452-66. doi: 10.3390/molecules15064452. [PMID: 20657453]
  • Dieter Treutter. Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints. International journal of molecular sciences. 2010 Mar; 11(3):807-57. doi: 10.3390/ijms11030807. [PMID: 20479987]
  • Guo-An Zou, Zhi-Heng Su, Hong-Wu Zhang, Yuan Wang, Jun-Shan Yang, Zhong-Mei Zou. Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook. Molecules (Basel, Switzerland). 2010 Feb; 15(3):1097-102. doi: 10.3390/molecules15031097. [PMID: 20335965]
  • M F Yam, L F Ang, R Basir, I M Salman, O Z Ameer, M Z Asmawi. Evaluation of the anti-pyretic potential of Orthosiphon stamineus Benth standardized extract. Inflammopharmacology. 2009 Feb; 17(1):50-4. doi: 10.1007/s10787-008-8038-3. [PMID: 19127348]
  • Toshifumi Hirata, Misato Fujii, Kazuhiro Akita, Noriyuki Yanaka, Kaori Ogawa, Masanori Kuroyanagi, Daiki Hongo. Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer. Bioorganic & medicinal chemistry. 2009 Jan; 17(1):25-8. doi: 10.1016/j.bmc.2008.11.039. [PMID: 19054677]
  • Zhenyu Wang, Shiming Li, Stephen Ferguson, Robert Goodnow, Chi-Tang Ho. Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts. Journal of separation science. 2008 Jan; 31(1):30-7. doi: 10.1002/jssc.200700331. [PMID: 18095294]
  • Shiming Li, Min-Hsiung Pan, Ching-Shu Lai, Chih-Yu Lo, Slavik Dushenkov, Chi-Tang Ho. Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines. Bioorganic & medicinal chemistry. 2007 May; 15(10):3381-9. doi: 10.1016/j.bmc.2007.03.021. [PMID: 17391969]
  • Da-Yong Zhou, De-Liang Chen, Qing Xu, Xing-Ya Xue, Fei-Fang Zhang, Xin-Miao Liang. Characterization of polymethoxylated flavones in Fructus aurantii by liquid chromatography with atmospheric pressure chemical ionization combined with tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2007 Apr; 43(5):1692-9. doi: 10.1016/j.jpba.2006.12.032. [PMID: 17291708]
  • Yanhua Lu, Chongwei Zhang, Peter Bucheli, Dongzhi Wei. Citrus flavonoids in fruit and traditional Chinese medicinal food ingredients in China. Plant foods for human nutrition (Dordrecht, Netherlands). 2006 Jun; 61(2):57-65. doi: 10.1007/s11130-006-0014-8. [PMID: 16816988]
  • Berthold Weber, Beate Hartmann, Detlef Stöckigt, Klaus Schreiber, Michael Roloff, Heinz-Jürgen Bertram, Claus O Schmidt. Liquid chromatography/mass spectrometry and liquid chromatography/nuclear magnetic resonance as complementary analytical techniques for unambiguous identification of polymethoxylated flavones in residues from molecular distillation of orange peel oils (Citrus sinensis). Journal of agricultural and food chemistry. 2006 Jan; 54(2):274-8. doi: 10.1021/jf051606f. [PMID: 16417279]
  • Yit Hong Loon, Jia Woei Wong, Siew Ping Yap, Kah Hay Yuen. Determination of flavonoids from Orthosiphon stamineus in plasma using a simple HPLC method with ultraviolet detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Feb; 816(1-2):161-6. doi: 10.1016/j.jchromb.2004.11.021. [PMID: 15664346]
  • Yoichi Nogata, Hideaki Ohta, Takashi Sumida, Keizo Sekiya. Effect of extraction method on the concentrations of selected bioactive compounds in mandarin juice. Journal of agricultural and food chemistry. 2003 Dec; 51(25):7346-51. doi: 10.1021/jf034732x. [PMID: 14640582]
  • A Ortuño, M C Arcas, J M Botía, M D Fuster, J A Del Río. Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels. Journal of agricultural and food chemistry. 2002 May; 50(10):2836-9. doi: 10.1021/jf011382a. [PMID: 11982408]
  • B Delaney, K Phillips, C Vasquez, A Wilson, D Cox, H-B Wang, J Manthey. Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2002 May; 40(5):617-24. doi: 10.1016/s0278-6915(02)00007-8. [PMID: 11955667]
  • B Delaney, K Phillips, D Buswell, B Mowry, D Nickels, D Cox, H B Wang, J Manthey. Immunotoxicity of a standardized citrus polymethoxylated flavone extract. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2001 Nov; 39(11):1087-94. doi: 10.1016/s0278-6915(01)00058-8. [PMID: 11527568]
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