Vescalagin (BioDeep_00000020951)

   

human metabolite


代谢物信息卡片


7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone

化学式: C41H26O26 (934.0712296)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O1)O)O)O)O)O)O
InChI: InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2

描述信息

Castalagin is found in european chestnut. Castalagin is isolated from sweet chestnut.Castalagin is a ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Anogeissus leiocarpus and Terminalia avicennoides. Castalagin is the (33beta)-isomer of vescalagin. (Wikipedia).
Isolated from sweet chestnut

同义名列表

6 个代谢物同义名

7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.1³⁸,⁴².0²,²⁰.0⁵,¹⁰.0¹¹,¹⁶.0²³,²⁸.0³³,⁴⁵.0³⁴,³⁹]hexatetraconta-5(10),6,8,11(16),12,14,23(28),24,26,29,31,33(45),34(39),35,37-pentadecaene-4,17,22,40,44-pentone; Vescalagin, (33beta)-isomer; vescalagin; Castalagin; Vescalene; Vescalin



数据库引用编号

10 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)

13 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

  • Karl Kempf, Yoan Capello, Rana Melhem, Claire Lescoat, Oxana Kempf, Anaëlle Cornu, Isabelle Fremaux, Stéphane Chaignepain, Alexis Groppi, Macha Nikolski, Denis Deffieux, Elisabeth Génot, Stéphane Quideau. Systemic Convergent Multitarget Interactions of Plant Polyphenols Revealed by Affinity-Based Protein Profiling of Bone Cells Using C-Glucosidic Vescal(ag)in-Bearing Chemoproteomic Probes. ACS chemical biology. 2023 Dec; 18(12):2495-2505. doi: 10.1021/acschembio.3c00440. [PMID: 37948120]
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  • Mohamed A A Orabi, Hiroshi Sakagami, Naoki Umemura, Hamad S Alyami, Tsutomu Hatano. Two new C-glycosidic ellagitannins and accompanying tannins from Lawsonia inermis leaves and their cytotoxic effects. Fitoterapia. 2021 Sep; 153(?):104925. doi: 10.1016/j.fitote.2021.104925. [PMID: 33984438]
  • Marina Fidelis, Jânio Sousa Santos, Graziela Bragueto Escher, Ramon Silva Rocha, Adriano Gomes Cruz, Thiago Mendanha Cruz, Mariza Boscacci Marques, Juliana Barbosa Nunes, Mariana Araújo Vieira do Carmo, Leonardo Augusto de Almeida, Tai Kaneshima, Luciana Azevedo, Daniel Granato. Polyphenols of jabuticaba [Myrciaria jaboticaba (Vell.) O.Berg] seeds incorporated in a yogurt model exert antioxidant activity and modulate gut microbiota of 1,2-dimethylhydrazine-induced colon cancer in rats. Food chemistry. 2021 Jan; 334(?):127565. doi: 10.1016/j.foodchem.2020.127565. [PMID: 32717686]
  • Sara Štumpf, Gregor Hostnik, Mateja Primožič, Maja Leitgeb, Juha-Pekka Salminen, Urban Bren. The Effect of Growth Medium Strength on Minimum Inhibitory Concentrations of Tannins and Tannin Extracts against E. coli. Molecules (Basel, Switzerland). 2020 Jun; 25(12):. doi: 10.3390/molecules25122947. [PMID: 32604845]
  • Marina Fidelis, Mariana Araújo Vieira do Carmo, Thiago Mendanha da Cruz, Luciana Azevedo, Takao Myoda, Marianna Miranda Furtado, Mariza Boscacci Marques, Anderson S Sant'Ana, Maria Inês Genovese, Won Young Oh, Mingchun Wen, Fereidoon Shahidi, Liang Zhang, Marcelo Franchin, Severino Matias de Alencar, Pedro Luiz Rosalen, Daniel Granato. Camu-camu seed (Myrciaria dubia) - From side stream to anantioxidant, antihyperglycemic, antiproliferative, antimicrobial, antihemolytic, anti-inflammatory, and antihypertensive ingredient. Food chemistry. 2020 Apr; 310(?):125909. doi: 10.1016/j.foodchem.2019.125909. [PMID: 31816536]
  • Marina Fidelis, Stephanie Maiara de Oliveira, Jânio Sousa Santos, Graziela Bragueto Escher, Ramon Silva Rocha, Adriano Gomes Cruz, Mariana Araújo Vieira do Carmo, Luciana Azevedo, Tai Kaneshima, Won Young Oh, Fereidoon Shahidi, Daniel Granato. From byproduct to a functional ingredient: Camu-camu (Myrciaria dubia) seed extract as an antioxidant agent in a yogurt model. Journal of dairy science. 2020 Feb; 103(2):1131-1140. doi: 10.3168/jds.2019-17173. [PMID: 31759605]
  • Yasuhiro Kamada, Hibiki Yakabu, Toshio Ichiba, Ayumi Tamanaha, Maria Shimoji, Megumi Kato, Chie Norimoto, Risa Yamashiro, Ikuko Miyagi, Akikazu Sakudo, Yasuharu Tanaka. Castalagin and vescalagin purified from leaves of Syzygium samarangense (Blume) Merrill & L.M. Perry: Dual inhibitory activity against PARP1 and DNA topoisomerase II. Fitoterapia. 2018 Sep; 129(?):94-101. doi: 10.1016/j.fitote.2018.06.015. [PMID: 29928967]
  • Yosuke Matsuo. Study of the Stereochemistry and Oxidation Mechanism of Plant Polyphenols, Assisted by Computational Chemistry. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2017; 137(3):347-354. doi: 10.1248/yakushi.16-00207. [PMID: 28250332]
  • Jakub P Piwowarski, Sebastian Granica, Joanna Stefańska, Anna K Kiss. Differences in Metabolism of Ellagitannins by Human Gut Microbiota ex Vivo Cultures. Journal of natural products. 2016 Dec; 79(12):3022-3030. doi: 10.1021/acs.jnatprod.6b00602. [PMID: 28006907]
  • V C Graça, Lillian Barros, Ricardo C Calhelha, Maria Inês Dias, Ana Maria Carvalho, Celestino Santos-Buelga, P F Santos, Isabel C F R Ferreira. Chemical characterization and bioactive properties of aqueous and organic extracts of Geranium robertianum L. Food & function. 2016 Sep; 7(9):3807-14. doi: 10.1039/c6fo01075j. [PMID: 27603422]
  • Da-Wei Huang, Wen-Chang Chang, James Swi-Bea Wu, Rui-Wen Shih, Szu-Chuan Shen. Vescalagin from Pink Wax Apple [Syzygium samarangense (Blume) Merrill and Perry] Alleviates Hepatic Insulin Resistance and Ameliorates Glycemic Metabolism Abnormality in Rats Fed a High-Fructose Diet. Journal of agricultural and food chemistry. 2016 Feb; 64(5):1122-9. doi: 10.1021/acs.jafc.5b05558. [PMID: 26800576]
  • Mayumi Iwatake, Kuniaki Okamoto, Takashi Tanaka, Takayuki Tsukuba. Castalagin Exerts Inhibitory Effects on Osteoclastogenesis Through Blocking a Broad Range of Signaling Pathways with Low Cytotoxicity. Phytotherapy research : PTR. 2015 Jun; 29(6):917-24. doi: 10.1002/ptr.5333. [PMID: 25809147]
  • Jakub P Piwowarski, Anna K Kiss. Contribution of C-glucosidic ellagitannins to Lythrum salicaria L. influence on pro-inflammatory functions of human neutrophils. Journal of natural medicines. 2015 Jan; 69(1):100-10. doi: 10.1007/s11418-014-0873-5. [PMID: 25349049]
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  • Jakub P Piwowarski, Anna K Kiss. C-glucosidic ellagitannins from Lythri herba (European Pharmacopoeia): chromatographic profile and structure determination. Phytochemical analysis : PCA. 2013 Jul; 24(4):336-48. doi: 10.1002/pca.2415. [PMID: 23280650]
  • Wen-Chang Chang, Szu-Chuan Shen. Effect of water extracts from edible Myrtaceae plants on uptake of 2-(n-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose in TNF-α-treated FL83B mouse hepatocytes. Phytotherapy research : PTR. 2013 Feb; 27(2):236-43. doi: 10.1002/ptr.4681. [PMID: 22532499]
  • Szu-Chuan Shen, Wen-Chang Chang. Hypotriglyceridemic and hypoglycemic effects of vescalagin from Pink wax apple [Syzygium samarangense (Blume) Merrill and Perry cv. Pink] in high-fructose diet-induced diabetic rats. Food chemistry. 2013 Jan; 136(2):858-63. doi: 10.1016/j.foodchem.2012.08.037. [PMID: 23122137]
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  • Diana M Castañeda, Luis Miguel Pombo, Claudia Patricia Urueña, John Fredy Hernandez, Susana Fiorentino. A gallotannin-rich fraction from Caesalpinia spinosa (Molina) Kuntze displays cytotoxic activity and raises sensitivity to doxorubicin in a leukemia cell line. BMC complementary and alternative medicine. 2012 Apr; 12(?):38. doi: 10.1186/1472-6882-12-38. [PMID: 22490328]
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  • M N Shuaibu, K Pandey, P A Wuyep, T Yanagi, K Hirayama, A Ichinose, T Tanaka, I Kouno. Castalagin from Anogeissus leiocarpus mediates the killing of Leishmania in vitro. Parasitology research. 2008 Nov; 103(6):1333-8. doi: 10.1007/s00436-008-1137-7. [PMID: 18690475]
  • Mohamed S A Marzouk, Fatma A Moharram, Mona A Mohamed, Amira M Gamal-Eldeen, Elsayed A Aboutabl. Anticancer and antioxidant tannins from Pimenta dioica leaves. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2007 Jul; 62(7-8):526-36. doi: 10.1515/znc-2007-7-811. [PMID: 17913067]
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