Punicalagin (BioDeep_00000230745)

 

Secondary id: BioDeep_00000028157

PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


(63R,64R,64aS,616aR)-14,15,16,22,23,27,28,34,35,36,61,68,69,610,611,612,613-heptadecahydroxy-25,210,63,64,64a,66,615,616a-octahydro-61H-5,8-dioxa-6(4,3)-dibenzo[f,h]pyrano[3,4-b][1,4]dioxecina-2(1,6)-chromeno[5,4,3-cde]chromena-1,3(1,2)-dibenzenacyclononaphane-25,210,66,615,4,9-hexaone

化学式: C48H28O30 (1084.0665388)
中文名称: 安石榴甙, 安石榴苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C2C(C3C(C(O2)O)OC(=O)C4=CC(=C(C(=C4C5=C(C(=C(C=C5C(=O)O3)O)O)O)O)O)O)OC(=O)C6=CC(=C(C(=C6C7=C(C(=C8C9=C7C(=O)OC2=C(C(=C(C3=C(C(=C(C=C3C(=O)O1)O)O)O)C(=C92)C(=O)O8)O)O)O)O)O)O)O
InChI: InChI=1S/C48H28O30/c49-10-1-6-17(31(59)27(10)55)19-23-21-22-24(47(70)76-38(21)35(63)33(19)61)20(34(62)36(64)39(22)75-46(23)69)18-9(4-13(52)28(56)32(18)60)43(66)74-37-14(5-72-42(6)65)73-48(71)41-40(37)77-44(67)7-2-11(50)25(53)29(57)15(7)16-8(45(68)78-41)3-12(51)26(54)30(16)58/h1-4,14,37,40-41,48-64,71H,5H2/t14-,37-,40+,41-,48?/m1/s1

描述信息

Punicalagin is a tannin.
(1R,35R,38R,55S)-6,7,8,11,12,23,24,27,28,29,37,43,44,45,48,49,50-heptadecahydroxy-2,14,21,33,36,39,54-heptaoxaundecacyclo[33.20.0.04,9.010,19.013,18.016,25.017,22.026,31.038,55.041,46.047,52]pentapentaconta-4,6,8,10,12,16,18,22,24,26,28,30,41,43,45,47,49,51-octadecaene-3,15,20,32,40,53-hexone is a natural product found in Terminalia chebula, Terminalia citrina, and other organisms with data available.
Punicalagin is a polyphenol ingredient isolated from Pomegranate (Punica granatum L.) or the leaves of Terminalia catappa L.. Punicalagin is a reversible and non-competitive 3CLpro inhibitor and inhibits SARS-CoV-2 replication in vitro. Punicalagin is an anti-hepatitis B virus (HBV) agent and has antioxidant, anti-inflammatory, and anticancer effects. Punicalagin has the potential for the research of COVID-19[1][2][3].
Punicalagin is a polyphenol ingredient isolated from Pomegranate (Punica granatum L.) or the leaves of Terminalia catappa L.. Punicalagin is a reversible and non-competitive 3CLpro inhibitor and inhibits SARS-CoV-2 replication in vitro. Punicalagin is an anti-hepatitis B virus (HBV) agent and has antioxidant, anti-inflammatory, and anticancer effects. Punicalagin has the potential for the research of COVID-19[1][2][3].

同义名列表

7 个代谢物同义名

(63R,64R,64aS,616aR)-14,15,16,22,23,27,28,34,35,36,61,68,69,610,611,612,613-heptadecahydroxy-25,210,63,64,64a,66,615,616a-octahydro-61H-5,8-dioxa-6(4,3)-dibenzo[f,h]pyrano[3,4-b][1,4]dioxecina-2(1,6)-chromeno[5,4,3-cde]chromena-1,3(1,2)-dibenzenacyclononaphane-25,210,66,615,4,9-hexaone; 6,7,8,11,12,23,24,27,28,29,37,43,44,45,48,49,50-heptadecahydroxy-2,14,21,33,36,39,54-heptaoxaundecacyclo[33.20.0.04,9.010,19.013,18.016,25.017,22.026,31.038,55.041,46.047,52]pentapentaconta-4,6,8,10,12,16,18,22,24,26,28,30,41,43,45,47,49,51-octadecaene-3,15,20,32,40,53-hexone; Punicalagin, >=98\\% (HPLC), from pomegranate; Punicalagin, analytical standard; Punicalagin, Technical grade; a pomegranate ellagitannin; Punicalagin



数据库引用编号

13 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)

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

  • Muthana M Jghef, Khadija Boukholda, Yassine Chtourou, Bernd L Fiebich, Mohammed Kebieche, Rachid Soulimani, Fatiha Chigr, Hamadi Fetoui. Punicalagin attenuates myocardial oxidative damage, inflammation, and apoptosis in isoproterenol-induced myocardial infarction in rats: Biochemical, immunohistochemical, and in silico molecular docking studies. Chemico-biological interactions. 2023 Oct; 385(?):110745. doi: 10.1016/j.cbi.2023.110745. [PMID: 37806379]
  • Rebeca Quirós-Fernández, Bricia López-Plaza, Laura M Bermejo, Samara Palma Milla, Andrea Zangara, Carmen Gómez Candela. Oral Supplement Containing Hydroxytyrosol and Punicalagin Improves Dyslipidemia in an Adult Population without Co-Adjuvant Treatment: A Randomized, Double-Blind, Controlled and Crossover Trial. Nutrients. 2022 Apr; 14(9):. doi: 10.3390/nu14091879. [PMID: 35565844]
  • Qinglian Hua, Yaling Han, Haifeng Zhao, Haowen Zhang, Bei Yan, Shengjie Pei, Xin He, Yue Li, Xiangyuan Meng, Lei Chen, Feng Zhong, Duo Li. Punicalagin alleviates renal injury via the gut-kidney axis in high-fat diet-induced diabetic mice. Food & function. 2022 Jan; 13(2):867-879. doi: 10.1039/d1fo03343c. [PMID: 34989745]
  • Saleem H Aladaileh, Farhan K Al-Swailmi, Mohammad H Abukhalil, Ahmad F Ahmeda, Ayman M Mahmoud. Punicalagin prevents cisplatin-induced nephrotoxicity by attenuating oxidative stress, inflammatory response, and apoptosis in rats. Life sciences. 2021 Dec; 286(?):120071. doi: 10.1016/j.lfs.2021.120071. [PMID: 34688692]
  • Ruikun Du, Laura Cooper, Zinuo Chen, Hyun Lee, Lijun Rong, Qinghua Cui. Discovery of chebulagic acid and punicalagin as novel allosteric inhibitors of SARS-CoV-2 3CLpro. Antiviral research. 2021 06; 190(?):105075. doi: 10.1016/j.antiviral.2021.105075. [PMID: 33872675]
  • Ping Li, Ruikun Du, Zinuo Chen, Yanyan Wang, Peng Zhan, Xinyong Liu, Dongwei Kang, Zhaoyu Chen, Xiujuan Zhao, Lin Wang, Lijun Rong, Qinghua Cui. Punicalagin is a neuraminidase inhibitor of influenza viruses. Journal of medical virology. 2021 06; 93(6):3465-3472. doi: 10.1002/jmv.26449. [PMID: 32827314]
  • M J Saadh, A M Almaaytah, M Alaraj, M F Dababneh, I Sa'adeh, S M Aldalaen, A M Kharshid, A Alboghdadly, M Hailat, A Khaleel, K D Al-Hamaideh, W Abu Dayyih. Punicalagin and zinc (II) ions inhibit the activity of SARS-CoV-2 3CL-protease in vitro. European review for medical and pharmacological sciences. 2021 05; 25(10):3908-3913. doi: 10.26355/eurrev_202105_25958. [PMID: 34109605]
  • Amir Foroutanfar, Soghra Mehri, Marzyeh Kamyar, Zahra Tandisehpanah, Hossein Hosseinzadeh. Protective effect of punicalagin, the main polyphenol compound of pomegranate, against acrylamide-induced neurotoxicity and hepatotoxicity in rats. Phytotherapy research : PTR. 2020 Dec; 34(12):3262-3272. doi: 10.1002/ptr.6774. [PMID: 32592417]
  • Dan Jin, Baiyu Zhang, Qiaoling Li, Jingjing Tu, Benhong Zhou. Effect of punicalagin on multiple targets in streptozotocin/high-fat diet-induced diabetic mice. Food & function. 2020 Dec; 11(12):10617-10634. doi: 10.1039/d0fo01275k. [PMID: 33210684]
  • Thaísa Cristina Silva, Renato Ivan de Ávila, Ana Laura Sene Amâncio Zara, Andressa Santana Santos, Fábio Ataídes, Vivianny Aparecida Queiroz Freitas, Carolina Rodrigues Costa, Marize Campos Valadares, Maria do Rosário Rodrigues Silva. Punicalagin triggers ergosterol biosynthesis disruption and cell cycle arrest in Cryptococcus gattii and Candida albicans : Action mechanisms of punicalagin against yeasts. Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology]. 2020 Dec; 51(4):1719-1727. doi: 10.1007/s42770-020-00364-4. [PMID: 32856241]
  • Ayumi Saeki, Kohsuke Tsuchiya, Takashi Suda, Takeshi Into, Akira Hasebe, Toshihiko Suzuki, Ken-Ichiro Shibata. Gasdermin D-independent release of interleukin-1β by living macrophages in response to mycoplasmal lipoproteins and lipopeptides. Immunology. 2020 10; 161(2):114-122. doi: 10.1111/imm.13230. [PMID: 32592165]
  • Yohan Seo, Chin Hee Mun, So-Hyeon Park, Dongkyu Jeon, Su Jeong Kim, Taejun Yoon, Eunhee Ko, Sungwoo Jo, Yong-Beom Park, Wan Namkung, Sang-Won Lee. Punicalagin Ameliorates Lupus Nephritis via Inhibition of PAR2. International journal of molecular sciences. 2020 Jul; 21(14):. doi: 10.3390/ijms21144975. [PMID: 32674502]
  • Xin An, Yahui Zhang, Yuan Cao, Jihua Chen, Hong Qin, Lina Yang. Punicalagin Protects Diabetic Nephropathy by Inhibiting Pyroptosis Based on TXNIP/NLRP3 Pathway. Nutrients. 2020 May; 12(5):. doi: 10.3390/nu12051516. [PMID: 32456088]
  • Xinzhe Feng, Qinyuan Yang, Chen Wang, Wenwen Tong, Weidong Xu. Punicalagin Exerts Protective Effects against Ankylosing Spondylitis by Regulating NF-κB-TH17/JAK2/STAT3 Signaling and Oxidative Stress. BioMed research international. 2020; 2020(?):4918239. doi: 10.1155/2020/4918239. [PMID: 33029510]
  • Yahui Zhang, Yuan Cao, Jihua Chen, Hong Qin, Lina Yang. A New Possible Mechanism by Which Punicalagin Protects against Liver Injury Induced by Type 2 Diabetes Mellitus: Upregulation of Autophagy via the Akt/FoxO3a Signaling Pathway. Journal of agricultural and food chemistry. 2019 Dec; 67(50):13948-13959. doi: 10.1021/acs.jafc.9b05910. [PMID: 31698901]
  • Jingfang Luo, Yi Long, Guofeng Ren, Yahui Zhang, Jihua Chen, Ruixue Huang, Lina Yang. Punicalagin Reversed the Hepatic Injury of Tetrachloromethane by Antioxidation and Enhancement of Autophagy. Journal of medicinal food. 2019 Dec; 22(12):1271-1279. doi: 10.1089/jmf.2019.4411. [PMID: 31718395]
  • Nadia M El-Beih, Gamal Ramadan, Enas A El-Husseiny, Aya M Hussein. Effects of pomegranate aril juice and its punicalagin on some key regulators of insulin resistance and oxidative liver injury in streptozotocin-nicotinamide type 2 diabetic rats. Molecular biology reports. 2019 Aug; 46(4):3701-3711. doi: 10.1007/s11033-019-04813-8. [PMID: 31006095]
  • Xuyun Liu, Ke Cao, Weiqiang Lv, Zhihui Feng, Jing Liu, Jing Gao, Hua Li, Weijin Zang, Jiankang Liu. Punicalagin attenuates endothelial dysfunction by activating FoxO1, a pivotal regulating switch of mitochondrial biogenesis. Free radical biology & medicine. 2019 05; 135(?):251-260. doi: 10.1016/j.freeradbiomed.2019.03.011. [PMID: 30878647]
  • Mohammed A El-Missiry, Magda A ElKomy, Azza I Othman, Ali M AbouEl-Ezz. Punicalagin ameliorates the elevation of plasma homocysteine, amyloid-β, TNF-α and apoptosis by advocating antioxidants and modulating apoptotic mediator proteins in brain. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Jun; 102(?):472-480. doi: 10.1016/j.biopha.2018.03.096. [PMID: 29579708]
  • Dana Atrahimovich, Abraham O Samson, Ali Khattib, Jacob Vaya, Soliman Khatib. Punicalagin Decreases Serum Glucose Levels and Increases PON1 Activity and HDL Anti-Inflammatory Values in Balb/c Mice Fed a High-Fat Diet. Oxidative medicine and cellular longevity. 2018; 2018(?):2673076. doi: 10.1155/2018/2673076. [PMID: 30151068]
  • Oluwatosin Adaramoye, Bettina Erguen, Bianca Nitzsche, Michael Höpfner, Klaus Jung, Anja Rabien. Punicalagin, a polyphenol from pomegranate fruit, induces growth inhibition and apoptosis in human PC-3 and LNCaP cells. Chemico-biological interactions. 2017 Aug; 274(?):100-106. doi: 10.1016/j.cbi.2017.07.009. [PMID: 28709945]
  • Julie Rodriguez, Olivier Caille, Daneel Ferreira, Marc Francaux. Pomegranate extract prevents skeletal muscle of mice against wasting induced by acute TNF-α injection. Molecular nutrition & food research. 2017 04; 61(4):. doi: 10.1002/mnfr.201600169. [PMID: 27804206]
  • Amr A Fouad, Hatem O Qutub, Walid N Al-Melhim. Nephroprotection of punicalagin in rat model of endotoxemic acute kidney injury. Toxicology mechanisms and methods. 2016 Sep; 26(7):538-543. doi: 10.1080/15376516.2016.1211207. [PMID: 27464552]
  • Amr A Fouad, Hatem O Qutub, Walid N Al-Melhim. Punicalagin alleviates hepatotoxicity in rats challenged with cyclophosphamide. Environmental toxicology and pharmacology. 2016 Jul; 45(?):158-62. doi: 10.1016/j.etap.2016.05.031. [PMID: 27310207]
  • Dana Atrahimovich, Soliman Khatib, Shifra Sela, Jacob Vaya, Abraham O Samson. Punicalagin Induces Serum Low-Density Lipoprotein Influx to Macrophages. Oxidative medicine and cellular longevity. 2016; 2016(?):7124251. doi: 10.1155/2016/7124251. [PMID: 27516832]
  • Guanghui Li, Yuqing Feng, Yunfeng Xu, Qian Wu, Qi'an Han, Xiujun Liang, Baowei Yang, Xin Wang, Xiaodong Xia. The anti-infective activity of punicalagin against Salmonella enterica subsp. enterica serovar typhimurium in mice. Food & function. 2015 Jul; 6(7):2357-64. doi: 10.1039/c5fo00053j. [PMID: 26084785]
  • María A Nuñez-Sánchez, Rocío García-Villalba, Tamara Monedero-Saiz, Noelia V García-Talavera, María B Gómez-Sánchez, Carmen Sánchez-Álvarez, Ana M García-Albert, Francisco J Rodríguez-Gil, Miguel Ruiz-Marín, Francisco A Pastor-Quirante, Francisco Martínez-Díaz, María J Yáñez-Gascón, Antonio González-Sarrías, Francisco A Tomás-Barberán, Juan C Espín. Targeted metabolic profiling of pomegranate polyphenols and urolithins in plasma, urine and colon tissues from colorectal cancer patients. Molecular nutrition & food research. 2014 Jun; 58(6):1199-211. doi: 10.1002/mnfr.201300931. [PMID: 24532260]
  • Farrukh Aqil, Manicka V Vadhanam, Ramesh C Gupta. Enhanced activity of punicalagin delivered via polymeric implants against benzo[a]pyrene-induced DNA adducts. Mutation research. 2012 Mar; 743(1-2):59-66. doi: 10.1016/j.mrgentox.2011.12.022. [PMID: 22234049]
  • Mira Rosenblat, Nina Volkova, John Ward, Michael Aviram. Paraoxonase 1 (PON1) inhibits monocyte-to-macrophage differentiation. Atherosclerosis. 2011 Nov; 219(1):49-56. doi: 10.1016/j.atherosclerosis.2011.06.054. [PMID: 21798540]
  • Eliana Harue Endo, Diógenes Aparício Garcia Cortez, Tânia Ueda-Nakamura, Celso Vataru Nakamura, Benedito Prado Dias Filho. Potent antifungal activity of extracts and pure compound isolated from pomegranate peels and synergism with fluconazole against Candida albicans. Research in microbiology. 2010 Sep; 161(7):534-40. doi: 10.1016/j.resmic.2010.05.002. [PMID: 20541606]
  • Jasmin Khateeb, Anna Gantman, Adam J Kreitenberg, Michael Aviram, Bianca Fuhrman. Paraoxonase 1 (PON1) expression in hepatocytes is upregulated by pomegranate polyphenols: a role for PPAR-gamma pathway. Atherosclerosis. 2010 Jan; 208(1):119-25. doi: 10.1016/j.atherosclerosis.2009.08.051. [PMID: 19783251]
  • Anand P Kulkarni, H S Mahal, S Kapoor, S M Aradhya. In vitro studies on the binding, antioxidant, and cytotoxic actions of punicalagin. Journal of agricultural and food chemistry. 2007 Feb; 55(4):1491-500. doi: 10.1021/jf0626720. [PMID: 17243704]
  • Susanne U Mertens-Talcott, Petra Jilma-Stohlawetz, Jolian Rios, Lal Hingorani, Hartmut Derendorf. Absorption, metabolism, and antioxidant effects of pomegranate (Punica granatum l.) polyphenols after ingestion of a standardized extract in healthy human volunteers. Journal of agricultural and food chemistry. 2006 Nov; 54(23):8956-61. doi: 10.1021/jf061674h. [PMID: 17090147]
  • Begoña Cerdá, Juan Carlos Espín, Soledad Parra, Pedro Martínez, Francisco A Tomás-Barberán. The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans. European journal of nutrition. 2004 Aug; 43(4):205-20. doi: 10.1007/s00394-004-0461-7. [PMID: 15309440]
  • Begoña Cerdá, José J Cerón, Francisco A Tomás-Barberán, Juan Carlos Espín. Repeated oral administration of high doses of the pomegranate ellagitannin punicalagin to rats for 37 days is not toxic. Journal of agricultural and food chemistry. 2003 May; 51(11):3493-501. doi: 10.1021/jf020842c. [PMID: 12744688]
  • Begoña Cerdá, Rafael Llorach, José J Cerón, Juan Carlos Espín, Francisco A Tomás-Barberán. Evaluation of the bioavailability and metabolism in the rat of punicalagin, an antioxidant polyphenol from pomegranate juice. European journal of nutrition. 2003 Jan; 42(1):18-28. doi: 10.1007/s00394-003-0396-4. [PMID: 12594538]
  • C C Lin, Y F Hsu, T C Lin, H Y Hsu. Antioxidant and hepatoprotective effects of punicalagin and punicalin on acetaminophen-induced liver damage in rats. Phytotherapy research : PTR. 2001 May; 15(3):206-12. doi: 10.1002/ptr.816. [PMID: 11351354]
  • C C Lin, Y F Hsu, T C Lin, F L Hsu, H Y Hsu. Antioxidant and hepatoprotective activity of punicalagin and punicalin on carbon tetrachloride-induced liver damage in rats. The Journal of pharmacy and pharmacology. 1998 Jul; 50(7):789-94. doi: 10.1111/j.2042-7158.1998.tb07141.x. [PMID: 9720629]