Vicenin 2 (BioDeep_00000003730)

 

Secondary id: BioDeep_00000230469, BioDeep_00000403002

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

化学式: C27H30O15 (594.158463)
中文名称: 维采宁-2, 维采宁-2
谱图信息: 最多检出来源 Viridiplantae(plant) 4.89%

分子结构信息

SMILES: c1(c(c(c2c(c1[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O)oc(cc2=O)c1ccc(cc1)O)O)[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)CO)O)O)O)O
InChI: InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2/t12-,13-,17+,18+,21-,22-,23+,24-,26-,27-/m0/s1

描述信息

Constituent of lemons (Citrus limon). Vicenin 2 is found in many foods, some of which are common salsify, fenugreek, sweet orange, and cucumber.
Vicenin 2 is found in citrus. Vicenin 2 is a constituent of lemons (Citrus limon)
Vicenin 2 is an angiotensin-converting enzyme (ACE) inhibitor (IC50=43.83 μM) from the aerial parts of Desmodium styracifolium[1].
Vicenin 2 is an angiotensin-converting enzyme (ACE) inhibitor (IC50=43.83 μM) from the aerial parts of Desmodium styracifolium[1].

同义名列表

18 个代谢物同义名

5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one; 6,8-Di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ci; 6-C-beta-D-xylopyranosyl-8-C-beta-D-glucopyranosyl apigenin; 6-C-Glucopyranosyl-8-C-galactopyranosylapigenin; 5,7,4-Trihydroxyflavone-6,8-di-C-glucoside; 6,8-Di-C-glucosyl-4,5,7-trihydroxyflavone; apigenin-6,8-di-C-glycopyranoside; 6,8-Di-C-glucopyranosylapigenin; Apigenin-6,8-di-C-glycoside; Apigenin 6,8-di-C-glucoside; 6,8-di-c-glucosylapigenin; Apigenin di-C-hexoside; vicenin II; Vicenin-1; Vicenin 2; vicenin-2; Vicenin



数据库引用编号

18 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)

280 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

  • Aboli Girme, Prajkta Bhoj, Ganesh Saste, Sandeep Pawar, Amit Mirgal, Dipak Raut, Machindra Chavan, Lal Hingorani. Development and Validation of RP-HPLC Method for Vicenin-2, Orientin, Cynaroside, Betulinic Acid, Genistein, and Major Eight Bioactive Constituents with LC-ESI-MS/MS Profiling in Ocimum Genus. Journal of AOAC International. 2021 Dec; 104(6):1634-1651. doi: 10.1093/jaoacint/qsab067. [PMID: 33930142]
  • Yijun Li, Yi Zheng, Huibo Wang. Anticancer activity of Vicenin-2 against 7,12 dimethylbenz[a]anthracene-induced buccal pouch carcinoma in hamsters. Journal of biochemical and molecular toxicology. 2021 Mar; 35(3):e22673. doi: 10.1002/jbt.22673. [PMID: 33314472]
  • Zhengping Zhang, Qinpeng Zhao, Tuanjiang Liu, He Zhao, Ruiguo Wang, Hui Li, Yongyuan Zhang, Lequn Shan, Baorong He, Xiaodong Wang, Linhong Huang, Dingjun Hao, Honghui Sun. Effect of Vicenin-2 on ovariectomy-induced osteoporosis in rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Sep; 129(?):110474. doi: 10.1016/j.biopha.2020.110474. [PMID: 32768959]
  • In-Chul Lee, Jong-Sup Bae. Hepatoprotective effects of vicenin-2 and scolymoside through the modulation of inflammatory pathways. Journal of natural medicines. 2020 Jan; 74(1):90-97. doi: 10.1007/s11418-019-01348-x. [PMID: 31350693]
  • Chunyang Zhang, Yuhui Chen, Ming Zhang, Chunni Xu, Guojin Gong, Vishnu Priya Veeraraghavan, Srinivasa Rao Bolla, Yandong Li. Vicenin-2 Treatment Attenuated the Diethylnitrosamine-Induced Liver Carcinoma and Oxidative Stress through Increased Apoptotic Protein Expression in Experimental Rats. Journal of environmental pathology, toxicology and oncology : official organ of the International Society for Environmental Toxicology and Cancer. 2020; 39(2):113-123. doi: 10.1615/jenvironpatholtoxicoloncol.2020031892. [PMID: 32749121]
  • Yueyuan Chen, Xiaojie Yan, Fenglai Lu, Xiaohua Jiang, J Brent Friesen, Guido F Pauli, Shao-Nong Chen, Dian-Peng Li. Preparation of flavone di-C-glycoside isomers from Jian-Gu injection (Premna fulva Craib.) using recycling counter-current chromatography. Journal of chromatography. A. 2019 Aug; 1599(?):180-186. doi: 10.1016/j.chroma.2019.03.030. [PMID: 30961965]
  • Yuti Yin, Lei Ye, Zhongbao Niu, Wenhui Fang. Anti-inflammatory effects of Vicenin-2 on dextran sulfate sodium-induced colitis in mice. Drug development research. 2019 08; 80(5):546-555. doi: 10.1002/ddr.21529. [PMID: 30972795]
  • Yingyi Luo, Zhiyao Ren, Biaoyan Du, Shangping Xing, Shaowei Huang, Yunrong Li, Zhouxi Lei, Dan Li, Huanhuan Chen, Yuechun Huang, Gang Wei. Structure Identification of ViceninII Extracted from Dendrobium officinale and the Reversal of TGF-β1-Induced Epithelial⁻Mesenchymal Transition in Lung Adenocarcinoma Cells through TGF-β/Smad and PI3K/Akt/mTOR Signaling Pathways. Molecules (Basel, Switzerland). 2019 Jan; 24(1):. doi: 10.3390/molecules24010144. [PMID: 30609689]
  • Xi Duan, Tao Wu, Ting Liu, Hao Yang, Xiaojie Ding, Yan Chen, Yunzhu Mu. Vicenin-2 ameliorates oxidative damage and photoaging via modulation of MAPKs and MMPs signaling in UVB radiation exposed human skin cells. Journal of photochemistry and photobiology. B, Biology. 2019 Jan; 190(?):76-85. doi: 10.1016/j.jphotobiol.2018.11.018. [PMID: 30502588]
  • Andréia C F Salgueiro, Vanderlei Folmer, Felipa E M Bassante, Márcia H S Cardoso, Hemerson S da Rosa, Gustavo O Puntel. Predictive antidiabetic activities of plants used by persons with Diabetes mellitus. Complementary therapies in medicine. 2018 Dec; 41(?):1-9. doi: 10.1016/j.ctim.2018.08.009. [PMID: 30477823]
  • Xianduo Sun, Xiaomin Tang, Quan Yang. An effective quantitative fingerprint method for evaluating the quality consistency of Desmodium styracifolium. Die Pharmazie. 2018 10; 73(10):579-584. doi: 10.1691/ph.2018.8590. [PMID: 30223921]
  • Magdalena Karamać, Hakime H Orak, Ryszard Amarowicz, Adnan Orak, Wojciech Piekoszewski. Phenolic contents and antioxidant capacities of wild and cultivated white lupin (Lupinus albus L.) seeds. Food chemistry. 2018 Aug; 258(?):1-7. doi: 10.1016/j.foodchem.2018.03.041. [PMID: 29655709]
  • Nurudeen Hassan, Ahmed Ali, Cathryn Withycombe, Maninder Ahluwalia, Raya Hamdan Al-Nasseri, Alex Tonks, Keith Morris. TET-2 up-regulation is associated with the anti-inflammatory action of Vicenin-2. Cytokine. 2018 08; 108(?):37-42. doi: 10.1016/j.cyto.2018.03.016. [PMID: 29567563]
  • Dong Yang, Xiling Zhang, Wencun Zhang, Thamaraiselvan Rengarajan. Vicenin-2 inhibits Wnt/β-catenin signaling and induces apoptosis in HT-29 human colon cancer cell line. Drug design, development and therapy. 2018; 12(?):1303-1310. doi: 10.2147/dddt.s149307. [PMID: 29849451]
  • Livia Marques Casanova, Wenqian Gu, Sônia Soares Costa, Per Bendix Jeppesen. Phenolic Substances from Ocimum Species Enhance Glucose-Stimulated Insulin Secretion and Modulate the Expression of Key Insulin Regulatory Genes in Mice Pancreatic Islets. Journal of natural products. 2017 12; 80(12):3267-3275. doi: 10.1021/acs.jnatprod.7b00699. [PMID: 29192771]
  • Kyung Min Jeong, Misuk Yang, Yan Jin, Eun Mi Kim, Jaeyoung Ko, Jeongmi Lee. Identification of Major Flavone C-Glycosides and Their Optimized Extraction from Cymbidium kanran Using Deep Eutectic Solvents. Molecules (Basel, Switzerland). 2017 Nov; 22(11):. doi: 10.3390/molecules22112006. [PMID: 29156555]
  • Amit D Kandhare, Subhash L Bodhankar, Vishwaraman Mohan, Prasad A Thakurdesai. Development and validation of HPLC method for vicenin-1 isolated from fenugreek seeds in rat plasma: application to pharmacokinetic, tissue distribution and excretion studies. Pharmaceutical biology. 2016 Nov; 54(11):2575-2583. doi: 10.3109/13880209.2016.1172245. [PMID: 27181500]
  • Amit D Kandhare, Subhash L Bodhankar, V Mohan, Prasad A Thakurdesai. Acute and repeated doses (28 days) oral toxicity study of Vicenin-1, a flavonoid glycoside isolated from fenugreek seeds in laboratory mice. Regulatory toxicology and pharmacology : RTP. 2016 Nov; 81(?):522-531. doi: 10.1016/j.yrtph.2016.10.013. [PMID: 27773753]
  • In-Chul Lee, Jong-Sup Bae. Anti-inflammatory effects of vicenin-2 and scolymoside on polyphosphate-mediated vascular inflammatory responses. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2016 Mar; 65(3):203-12. doi: 10.1007/s00011-015-0906-x. [PMID: 26621502]
  • Abubakar Amali Muhammad, Palanisamy Arulselvan, Pike See Cheah, Farida Abas, Sharida Fakurazi. Evaluation of wound healing properties of bioactive aqueous fraction from Moringa oleifera Lam on experimentally induced diabetic animal model. Drug design, development and therapy. 2016; 10(?):1715-30. doi: 10.2147/dddt.s96968. [PMID: 27307703]
  • Wonhwa Lee, Sae-Kwang Ku, Jong-Sup Bae. Ameliorative Effect of Vicenin-2 and Scolymoside on TGFBIp-Induced Septic Responses. Inflammation. 2015 Dec; 38(6):2166-77. doi: 10.1007/s10753-015-0199-9. [PMID: 26084452]
  • Wonhwa Lee, Jong-Sup Bae. Antithrombotic and antiplatelet activities of vicenin-2. Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis. 2015 Sep; 26(6):628-34. doi: 10.1097/mbc.0000000000000320. [PMID: 26126169]
  • Wonhwa Lee, Eun-Kyung Yoon, Kyung-Min Kim, Dong Ho Park, Jong-Sup Bae. Antiseptic effect of vicenin-2 and scolymoside from Cyclopia subternata (honeybush) in response to HMGB1 as a late sepsis mediator in vitro and in vivo. Canadian journal of physiology and pharmacology. 2015 Aug; 93(8):709-20. doi: 10.1139/cjpp-2015-0021. [PMID: 26243020]
  • Amel Boudjelal, Laura Siracusa, Cherifa Henchiri, Madani Sarri, Benkhaled Abderrahim, Faiza Baali, Giuseppe Ruberto. Antidiabetic Effects of Aqueous Infusions of Artemisia herba-alba and Ajuga iva in Alloxan-Induced Diabetic Rats. Planta medica. 2015 Jun; 81(9):696-704. doi: 10.1055/s-0035-1546006. [PMID: 26018915]
  • Fei Xiong, Hao Wang, Zhenzhou Jiang, Meirong Huo, Caiyun Yan, Chunli Zheng, Ning Gu. Integrated pharmacokinetics and biodistribution of multiple flavonoid C-glycosides components in rat after oral administration of Abrus mollis extract and correlations with bio-effects. Journal of ethnopharmacology. 2015 Apr; 163(?):290-6. doi: 10.1016/j.jep.2014.12.067. [PMID: 25614108]
  • Sônia Soares Costa, Maria Fernanda Paresqui Corrêa, Livia Marques Casanova. A new triglycosyl flavonoid isolated from leaf juice of Kalanchoe gastonis-bonnieri (Crassulaceae). Natural product communications. 2015 Mar; 10(3):433-6. doi: . [PMID: 25924522]
  • Md Nurul Islam, Ishrat Jahan Ishita, Hyun Ah Jung, Jae Sue Choi. Vicenin 2 isolated from Artemisia capillaris exhibited potent anti-glycation properties. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Jul; 69(?):55-62. doi: 10.1016/j.fct.2014.03.042. [PMID: 24713265]
  • Denise Brentan Silva, Izabel Cristina Casanova Turatti, Dayana Rubio Gouveia, Madeleine Ernst, Simone Pádua Teixeira, Norberto Peporine Lopes. Mass spectrometry of flavonoid vicenin-2, based sunlight barriers in Lychnophora species. Scientific reports. 2014 Mar; 4(?):4309. doi: 10.1038/srep04309. [PMID: 24603617]
  • Eugen J Verspohl, Hajime Fujii, Kohei Homma, Sybille Buchwald-Werner. Testing of Perilla frutescens extract and Vicenin 2 for their antispasmodic effect. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2013 Mar; 20(5):427-31. doi: 10.1016/j.phymed.2012.12.018. [PMID: 23357362]
  • Abubakar Amali Muhammad, Nur Aimi Syarina Pauzi, Palanisamy Arulselvan, Faridah Abas, Sharida Fakurazi. In vitro wound healing potential and identification of bioactive compounds from Moringa oleifera Lam. BioMed research international. 2013; 2013(?):974580. doi: 10.1155/2013/974580. [PMID: 24490175]
  • Dayana Rubio Gouvea, Fernando Meloni, Arthur de Barros Bello Ribeiro, João Luis Callegari Lopes, Norberto Peporine Lopes. A new HPLC-DAD-MS/MS method for the simultaneous determination of major compounds in the crude extract of Lychnophora salicifolia Mart. (Brazilian arnicão) leaves: application to chemical variability evaluation. Analytica chimica acta. 2012 Oct; 748(?):28-36. doi: 10.1016/j.aca.2012.08.027. [PMID: 23021804]
  • Fumio Matsuda, Yozo Okazaki, Akira Oikawa, Miyako Kusano, Ryo Nakabayashi, Jun Kikuchi, Jun-Ichi Yonemaru, Kaworu Ebana, Masahiro Yano, Kazuki Saito. Dissection of genotype-phenotype associations in rice grains using metabolome quantitative trait loci analysis. The Plant journal : for cell and molecular biology. 2012 May; 70(4):624-36. doi: 10.1111/j.1365-313x.2012.04903.x. [PMID: 22229385]
  • Lokesh Dalasanur Nagaprashantha, Rit Vatsyayan, Jyotsana Singhal, Spence Fast, Rhonda Roby, Sanjay Awasthi, Sharad S Singhal. Anti-cancer effects of novel flavonoid vicenin-2 as a single agent and in synergistic combination with docetaxel in prostate cancer. Biochemical pharmacology. 2011 Nov; 82(9):1100-9. doi: 10.1016/j.bcp.2011.07.078. [PMID: 21803027]
  • Michel David dos Santos, Guanjie Chen, Maria Camila Almeida, Denis Melo Soares, Glória Emília Petto de Souza, Norberto Peporine Lopes, R Clark Lantz. Effects of caffeoylquinic acid derivatives and C-flavonoid from Lychnophora ericoides on in vitro inflammatory mediator production. Natural product communications. 2010 May; 5(5):733-40. doi: . [PMID: 20521538]
  • Valquiria A Polisel Jabor, Denis Melo Soares, Andrea Diniz, Glória Emilia Petto de Souza, Norberto Peporine Lopes. LC-MS-MS identification and determination of the flavone-C-glucoside vicenin-2 in rat plasma samples following intraperitoneal administration of Lychnophora extract. Natural product communications. 2010 May; 5(5):741-5. doi: . [PMID: 20521539]
  • Li-Wen Tian, Ying Pei, Ying-Jun Zhang, Yi-Fei Wang, Chong-Ren Yang. 7-O-methylkaempferol and -quercetin glycosides from the whole plant of Nervilia fordii. Journal of natural products. 2009 Jun; 72(6):1057-60. doi: 10.1021/np800760p. [PMID: 19422205]
  • Leosvaldo S M Velozo, Marcelo J P Ferreira, Maria Isabel S Santos, Davyson L Moreira, Elsie F Guimarães, Vicente P Emerenciano, Maria Auxiliadora C Kaplan. C-glycosyl flavones from Peperomia blanda. Fitoterapia. 2009 Mar; 80(2):119-22. doi: 10.1016/j.fitote.2008.11.005. [PMID: 19100817]
  • Qiu-Ping Wu, Zhu-Ju Wang, Li-Ying Tang, Mei-Hong Fu, Yan He, Jing Fang, Qian-Feng Gong. [Determination of five primary chemical constituents in Cassia angustifolia by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Feb; 33(4):363-5. doi: ". [PMID: 18533485]
  • Solange Leite de Moraes, José Carlos Tomaz, Norberto Peporine Lopes. Liquid chromatography-tandem mass spectrometric method for determination of the anti-inflammatory compound vicenin-2 in the leaves of L. ericoides Mart. Biomedical chromatography : BMC. 2007 Sep; 21(9):925-30. doi: 10.1002/bmc.828. [PMID: 17428019]
  • Bin Zhu, Gui-Chang Bai, Shou-Jun Jiang, Feng Wei, Rui-Chao Lin. [Studies on chemical constituent and quantitative determination of Mallotus apelta]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 May; 32(10):932-4. doi: ". [PMID: 17655150]
  • Daniela M Biondi, Concetta Rocco, Giuseppe Ruberto. Dihydrostilbene derivatives from Glycyrrhiza glabra leaves. Journal of natural products. 2005 Jul; 68(7):1099-102. doi: 10.1021/np050034q. [PMID: 16038558]
  • V Nayak, P Uma Devi. Protection of mouse bone marrow against radiation-induced chromosome damage and stem cell death by the ocimum flavonoids orientin and vicenin. Radiation research. 2005 Feb; 163(2):165-71. doi: 10.1667/rr3263. [PMID: 15658892]
  • Leonardo Gobbo-Neto, Michel D Santos, Alexandre Kanashiro, Maria C Almeida, Yara M Lucisano-Valim, João L Lopes, Glória E Souza, Norberto P Lopes. Evaluation of the anti-inflammatory and antioxidant activities of di-C-glucoflavones from Lychnophora ericoides (Asteraceae). Planta medica. 2005 Jan; 71(1):3-6. doi: 10.1055/s-2005-837742. [PMID: 15678365]
  • P Uma Devi, A Ganasoundari, B Vrinda, K K Srinivasan, M K Unnikrishnan. Radiation protection by the ocimum flavonoids orientin and vicenin: mechanisms of action. Radiation research. 2000 Oct; 154(4):455-60. doi: 10.1667/0033-7587(2000)154[0455:rpbtof]2.0.co;2. [PMID: 11023610]
  • P Uma Devi, A Ganasoundari, B S Rao, K K Srinivasan. In vivo radioprotection by ocimum flavonoids: survival of mice. Radiation research. 1999 Jan; 151(1):74-8. doi: . [PMID: 9973087]
  • R Fänge, M L Johansson-Sjöbeck. The effect of splenectomy on the hematology and on the activity of delta-aminolevulinic acid dehydratase (ALA-D) in hemopoietic tissues of the dogfish, Scyliorhinus canicula (Elasmobranchii). Comparative biochemistry and physiology. A, Comparative physiology. 1975 Dec; 52(4):577-80. doi: 10.1016/s0300-9629(75)80002-8. [PMID: 1175]