Geraniin (BioDeep_00000000054)

   

PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


.beta.-D-Glucopyranose, cyclic 2.fwdarw.7:4.fwdarw.5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-methano-2H-1-benzoxocin-5,7-dicarboxylate)cyclic 3,6-(4,4,5,5,6,6-hexahydroxy[1,1-biphenyl]-2,2-dicarboxylate) 1-(3,4,5-trihydroxybenzoate), stereoisomer

化学式: C41H28O27 (952.0817938)
中文名称: 老鹳草素, 牛儿鞣素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 40%

分子结构信息

SMILES: C1C2C3C(C(C(O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5C7C(=CC(=O)C(C7(O)O)(O6)O)C(=O)O3)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/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-38(58)12-6-19(47)41(61)40(59,60)23(12)22-11(37(57)66-33)5-17(46)27(51)31(22)68-41)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2

描述信息

Geraniin is a tannin.
Geraniin is a natural product found in Euphorbia makinoi, Macaranga tanarius, and other organisms with data available.
Geraniin is a TNF-α releasing inhibitor with numerous activities including anticancer, anti-inflammatory, and anti-hyperglycemic activities, with an IC50 of 43 μM.
Geraniin is a TNF-α releasing inhibitor with numerous activities including anticancer, anti-inflammatory, and anti-hyperglycemic activities, with an IC50 of 43 μM.

同义名列表

7 个代谢物同义名

.beta.-D-Glucopyranose, cyclic 2.fwdarw.7:4.fwdarw.5-(3,6-dihydro-2,9,10,11,11-pentahydroxy-3-oxo-2,6-methano-2H-1-benzoxocin-5,7-dicarboxylate)cyclic 3,6-(4,4,5,5,6,6-hexahydroxy[1,1-biphenyl]-2,2-dicarboxylate) 1-(3,4,5-trihydroxybenzoate), stereoisomer; [undecahydroxy(pentaoxo)[?]yl] 3,4,5-trihydroxybenzoate; N-(4-CARBETHOXYPHENYL)-N-4-(6-BENZOTHIAZOLE)AMINE; JQQBXPCJFAKSPG-SVYIMCMUSA-N; CID 115063; Geraniiin; Geraniin



数据库引用编号

16 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)

64 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

  • Xiaoyi Zhou, Minyan Qin, Leran He, Ying Zhang, Aijun Liu, Dongfeng Chen, Hao Pan. Geraniin restricts inflammasome activation and macrophage pyroptosis by preventing the interaction between ASC and NLRP3 to exert anti-inflammatory effects. International immunopharmacology. 2024 Mar; 129(?):111656. doi: 10.1016/j.intimp.2024.111656. [PMID: 38340422]
  • Ji Li, Xuedong Wang, Xiangyu Meng, Xin Zhou, Han Huang, Yi Feng, Yujie Fu, Xinxin Liu, Bo Yu. Geraniin targeting CaMKK2 inhibits lipid accumulation in 3T3-L1 adipocytes by suppressing lipogenesis. Chemico-biological interactions. 2023 Feb; 372(?):110364. doi: 10.1016/j.cbi.2023.110364. [PMID: 36706894]
  • Kenji Kubo, Hikaru Watanabe, Hiroyuki Kumeta, Tomoyasu Aizawa, Chigusa Seki, Hiroto Nakano, Kiyotaka Tokuraku, Koji Uwai. Chemical analysis of amyloid β aggregation inhibitors derived from Geranium thunbergii. Bioorganic & medicinal chemistry. 2022 08; 68(?):116840. doi: 10.1016/j.bmc.2022.116840. [PMID: 35661848]
  • Kaiyang Lin, Xuedong Wang, Ji Li, Peng Zhao, Xiangwen Xi, Yi Feng, Li Yin, Jinwei Tian, Hulun Li, Xinxin Liu, Bo Yu. Anti-atherosclerotic effects of geraniin through the gut microbiota-dependent trimethylamine N-oxide (TMAO) pathway in mice. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jul; 101(?):154104. doi: 10.1016/j.phymed.2022.154104. [PMID: 35461005]
  • Wenping Zhang, Jishan Lin, Jianguo Li, Shaoquan Zheng, Xingtan Zhang, Shuai Chen, Xiaokai Ma, Fei Dong, Haifeng Jia, Xiuming Xu, Ziqin Yang, Panpan Ma, Fang Deng, Ban Deng, Yongji Huang, Zhanjie Li, Xiaozhou Lv, Yaying Ma, Zhenyang Liao, Zhicong Lin, Jing Lin, Shengcheng Zhang, Tracie Matsumoto, Rui Xia, Jisen Zhang, Ray Ming. Rambutan genome revealed gene networks for spine formation and aril development. The Plant journal : for cell and molecular biology. 2021 11; 108(4):1037-1052. doi: 10.1111/tpj.15491. [PMID: 34519122]
  • Young Soo Kim, Hwan-Suck Chung, Sang Gyun Noh, Bonggi Lee, Hae Young Chung, Jang-Gi Choi. Geraniin Inhibits the Entry of SARS-CoV-2 by Blocking the Interaction between Spike Protein RBD and Human ACE2 Receptor. International journal of molecular sciences. 2021 Aug; 22(16):. doi: 10.3390/ijms22168604. [PMID: 34445310]
  • Xiuhui Wang, Minghui Wang, Xu Cui, Zhuokai Li, Shengyang Guo, Feng Gao, Ming Ma, Zhe Wang. Antiosteoporosis effect of geraniin on ovariectomy-induced osteoporosis in experimental rats. Journal of biochemical and molecular toxicology. 2021 Jun; 35(6):1-8. doi: 10.1002/jbt.22774. [PMID: 33755276]
  • Deming Looi, Boon H Goh, Shafi U Khan, Nafees Ahemad, Uma D Palanisamy. Metabolites of the ellagitannin, geraniin inhibit human ACE; in vitro and in silico evidence. International journal of food sciences and nutrition. 2021 Jun; 72(4):470-477. doi: 10.1080/09637486.2020.1830263. [PMID: 33032478]
  • Asiri Perera, So Ha Ton, Mohanambal Moorthy, Uma Devi Palanisamy. The insulin-sensitising properties of the ellagitannin geraniin and its metabolites from Nephelium lappaceum rind in 3T3-L1 cells. International journal of food sciences and nutrition. 2020 Dec; 71(8):940-953. doi: 10.1080/09637486.2020.1754348. [PMID: 32319838]
  • Hong Sheng Cheng, Boon Hee Goh, Sonia Chew Wen Phang, Muhammad Mubarak Amanullah, So Ha Ton, Uma Devi Palanisamy, Khalid Abdul Kadir, Joash Ban Lee Tan. Pleiotropic ameliorative effects of ellagitannin geraniin against metabolic syndrome induced by high-fat diet in rats. Nutrition (Burbank, Los Angeles County, Calif.). 2020 Nov; 79-80(?):110973. doi: 10.1016/j.nut.2020.110973. [PMID: 32916379]
  • Juliano G Haddad, Dovilė Grauzdytė, Andrea Cristine Koishi, Wildriss Viranaicken, Petras Rimantas Venskutonis, Claudia Nunes Duarte Dos Santos, Philippe Desprès, Nicolas Diotel, Chaker El Kalamouni. The Geraniin-Rich Extract from Reunion Island Endemic Medicinal Plant Phyllanthus phillyreifolius Inhibits Zika and Dengue Virus Infection at Non-Toxic Effect Doses in Zebrafish. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102316. [PMID: 32429073]
  • Dovilė Grauzdytė, Audrius Pukalskas, Chaker El Kalamouni, Petras Rimantas Venskutonis. Antioxidant potential and phytochemical composition of extracts obtained from Phyllanthus phillyreifolius by different extraction methods. Natural product research. 2020 Mar; 34(5):706-709. doi: 10.1080/14786419.2018.1493586. [PMID: 30445845]
  • Manami Era, Yosuke Matsuo, Yoshinori Saito, Takashi Tanaka. Production of Ellagitannin Hexahydroxydiphenoyl Ester by Spontaneous Reduction of Dehydrohexa-hydroxydiphenoyl Ester. Molecules (Basel, Switzerland). 2020 Feb; 25(5):. doi: 10.3390/molecules25051051. [PMID: 32110993]
  • Sonia Chew Wen Phang, Uma Devi Palanisamy, Khalid Abdul Kadir. Effects of geraniin (rambutan rind extract) on blood pressure and metabolic parameters in rats fed high-fat diet. Journal of integrative medicine. 2019 Mar; 17(2):100-106. doi: 10.1016/j.joim.2019.01.008. [PMID: 30738774]
  • Siti Aisyah Abdul Ahmad, Uma D Palanisamy, Joon Joon Khoo, Amreeta Dhanoa, Sharifah Syed Hassan. Efficacy of geraniin on dengue virus type-2 infected BALB/c mice. Virology journal. 2019 02; 16(1):26. doi: 10.1186/s12985-019-1127-7. [PMID: 30813954]
  • Yujing Li, Zhaojie Li, Hu Hou, Yongliang Zhuang, Liping Sun. Metal Chelating, Inhibitory DNA Damage, and Anti-Inflammatory Activities of Phenolics from Rambutan (Nephelium lappaceum) Peel and the Quantifications of Geraniin and Corilagin. Molecules (Basel, Switzerland). 2018 Sep; 23(9):. doi: 10.3390/molecules23092263. [PMID: 30189625]
  • Eric Boakye-Gyasi, Ella Anle Kasanga, Elvis Ofori Ameyaw, Wonder Kofi Mensah Abotsi, Robert Peter Biney, Christian Agyare, Eric Woode. An isobolographic analysis of the anti-nociceptive effect of geraniin in combination with morphine or diclofenac. Journal of basic and clinical physiology and pharmacology. 2018 Mar; 29(2):201-209. doi: 10.1515/jbcpp-2017-0031. [PMID: 28988222]
  • Erika Moreno, Juan A Gayosso, José R Montejano, Georgina Almaguer, Norma Vázquez, Cristino Cruz, Adriana Mercado, Norma A Bobadilla, Gerardo Gamba, Alfredo Sierra, Victoria Ramírez. Geraniin is a diuretic by inhibiting the Na+-K+-2Cl- cotransporter NKCC2. American journal of physiology. Renal physiology. 2018 02; 314(2):F240-F250. doi: 10.1152/ajprenal.00221.2017. [PMID: 29046296]
  • Dovilė Grauzdytė, Audrius Pukalskas, Wildriss Viranaicken, Chaker El Kalamouni, Petras Rimantas Venskutonis. Protective effects of Phyllanthus phillyreifolius extracts against hydrogen peroxide induced oxidative stress in HEK293 cells. PloS one. 2018; 13(11):e0207672. doi: 10.1371/journal.pone.0207672. [PMID: 30444889]
  • Hoda Aayadi, Smriti P K Mittal, Anjali Deshpande, Makarand Gore, Saroj S Ghaskadbi. Cytoprotective effect exerted by geraniin in HepG2 cells is through microRNA mediated regulation of BACH-1 and HO-1. BMB reports. 2017 Nov; 50(11):560-565. doi: 10.5483/bmbrep.2017.50.11.060. [PMID: 28602161]
  • Hoda Aayadi, Smriti P K Mittal, Anjali Deshpande, Makarand Gore, Saroj S Ghaskadbi. Protective effect of geraniin against carbon tetrachloride induced acute hepatotoxicity in Swiss albino mice. Biochemical and biophysical research communications. 2017 05; 487(1):62-67. doi: 10.1016/j.bbrc.2017.04.013. [PMID: 28396147]
  • 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]
  • Lei Jiang, Yong Liu, Pengcheng He, Jiyan Chen, Shuangxin Liu, Ning Tan. Geraniin ameliorates cisplatin-induced nephrotoxicity in mice. Free radical research. 2016 Aug; 50(8):813-9. doi: 10.3109/10715762.2016.1173206. [PMID: 27043748]
  • Yaw Duah Boakye, Christian Agyare, Wonder Kofi Mensah Abotsi, Patrick George Ayande, Paul Poku Sampene Ossei. Anti-inflammatory activity of aqueous leaf extract of Phyllanthus muellerianus (Kuntze) Exell. and its major constituent, geraniin. Journal of ethnopharmacology. 2016 Jul; 187(?):17-27. doi: 10.1016/j.jep.2016.04.020. [PMID: 27103113]
  • Peng Wang, Qi Qiao, Ji Li, Wei Wang, Li-Ping Yao, Yu-Jie Fu. Inhibitory effects of geraniin on LPS-induced inflammation via regulating NF-κB and Nrf2 pathways in RAW 264.7 cells. Chemico-biological interactions. 2016 Jun; 253(?):134-42. doi: 10.1016/j.cbi.2016.05.014. [PMID: 27181634]
  • Jia-Wen Zhai, Chang Gao, Wei-Dong Ma, Wei Wang, Li-Ping Yao, Xin-Xin Xia, Meng Luo, Yuan-Gang Zu, Yu-Jie Fu. Geraniin induces apoptosis of human breast cancer cells MCF-7 via ROS-mediated stimulation of p38 MAPK. Toxicology mechanisms and methods. 2016 Jun; 26(5):311-8. doi: 10.3109/15376516.2016.1139025. [PMID: 27097871]
  • Yoonjung Lee, Hee Sun Byun, Jeong Ho Seok, Kyeong Ah Park, Minho Won, Wonhyoung Seo, So-Ra Lee, Kidong Kang, Kyung-Cheol Sohn, Ill Young Lee, Hyeong-Geug Kim, Chang Gue Son, Han-Ming Shen, Gang Min Hur. Terminalia Chebula provides protection against dual modes of necroptotic and apoptotic cell death upon death receptor ligation. Scientific reports. 2016 04; 6(?):25094. doi: 10.1038/srep25094. [PMID: 27117478]
  • Peng Wang, Xiao Peng, Zuo-Fu Wei, Fu-Yao Wei, Wei Wang, Wei-Dong Ma, Li-Ping Yao, Yu-Jie Fu, Yuan-Gang Zu. Geraniin exerts cytoprotective effect against cellular oxidative stress by upregulation of Nrf2-mediated antioxidant enzyme expression via PI3K/AKT and ERK1/2 pathway. Biochimica et biophysica acta. 2015 Sep; 1850(9):1751-61. doi: 10.1016/j.bbagen.2015.04.010. [PMID: 25917210]
  • Yiqin Lu, Bo He, Xiaochao Zhang, Renhua Yang, Shude Li, Bo Song, Yue Zhang, Yu Yun, Hongli Yan, Peng Chen, Zhiqiang Shen. Osteoprotective effect of geraniin against ovariectomy-induced bone loss in rats. Bioorganic & medicinal chemistry letters. 2015 Feb; 25(3):673-9. doi: 10.1016/j.bmcl.2014.11.081. [PMID: 25532904]
  • Chinedu P Anokwuru, Annamaria Sinisi, Amidou Samie, Orazio Taglialatela-Scafati. Antibacterial and antioxidant constituents of Acalypha wilkesiana. Natural product research. 2015; 29(12):1180-3. doi: 10.1080/14786419.2014.983105. [PMID: 25426700]
  • Sumita Elendran, Lee Wang Wang, Richard Prankerd, Uma D Palanisamy. The physicochemical properties of geraniin, a potential antihyperglycemic agent. Pharmaceutical biology. 2015; 53(12):1719-26. doi: 10.3109/13880209.2014.1003356. [PMID: 25853977]
  • Claudia Velázquez-González, Raquel Cariño-Cortés, Juan A Gayosso de Lucio, Mario I Ortiz, Minarda De la O Arciniega, Diana A Altamirano-Báez, Luis Jiménez- Ángeles, Mirandeli Bautista-Ávila. Antinociceptive and anti-inflammatory activities of Geranium bellum and its isolated compounds. BMC complementary and alternative medicine. 2014 Dec; 14(?):506. doi: 10.1186/1472-6882-14-506. [PMID: 25518981]
  • Anu Tuominen, Eija Toivonen, Pia Mutikainen, Juha-Pekka Salminen. Defensive strategies in Geranium sylvaticum. Part 1: organ-specific distribution of water-soluble tannins, flavonoids and phenolic acids. Phytochemistry. 2013 Nov; 95(?):394-407. doi: 10.1016/j.phytochem.2013.05.013. [PMID: 23790750]
  • Sau Har Lee, Yin Quan Tang, Anusyah Rathkrishnan, Seok Mui Wang, Kien Chai Ong, Rishya Manikam, Bobby Joe Payne, Indu Bala Jaganath, Shamala Devi Sekaran. Effects of cocktail of four local Malaysian medicinal plants (Phyllanthus spp.) against dengue virus 2. BMC complementary and alternative medicine. 2013 Jul; 13(?):192. doi: 10.1186/1472-6882-13-192. [PMID: 23889893]
  • So Jin Bing, Danbee Ha, Min Ju Kim, Eunjin Park, Ginnae Ahn, Dae Seung Kim, Ryeo Kyeong Ko, Jae Woo Park, Nam Ho Lee, Youngheun Jee. Geraniin down regulates gamma radiation-induced apoptosis by suppressing DNA damage. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Jul; 57(?):147-53. doi: 10.1016/j.fct.2013.03.022. [PMID: 23541438]
  • Antonio Vassallo, Maria Carmela Vaccaro, Nunziatina De Tommasi, Fabrizio Dal Piaz, Antonella Leone. Identification of the plant compound geraniin as a novel Hsp90 inhibitor. PloS one. 2013; 8(9):e74266. doi: 10.1371/journal.pone.0074266. [PMID: 24066128]
  • Jayant S Londhe, Thomas P A Devasagayam, L Yeap Foo, Padma Shastry, Saroj S Ghaskadbi. Geraniin and amariin, ellagitannins from Phyllanthus amarus, protect liver cells against ethanol induced cytotoxicity. Fitoterapia. 2012 Dec; 83(8):1562-8. doi: 10.1016/j.fitote.2012.09.003. [PMID: 22982332]
  • Dieudonné Ndjonka, Bärbel Bergmann, Christian Agyare, Flávia M Zimbres, Kai Lüersen, Andreas Hensel, Carsten Wrenger, Eva Liebau. In vitro activity of extracts and isolated polyphenols from West African medicinal plants against Plasmodium falciparum. Parasitology research. 2012 Aug; 111(2):827-34. doi: 10.1007/s00436-012-2905-y. [PMID: 22476602]
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  • Hidekazu Ishimoto, Mari Shibata, Yuki Myojin, Hideyuki Ito, Yukio Sugimoto, Akihiro Tai, Tsutomu Hatano. In vivo anti-inflammatory and antioxidant properties of ellagitannin metabolite urolithin A. Bioorganic & medicinal chemistry letters. 2011 Oct; 21(19):5901-4. doi: 10.1016/j.bmcl.2011.07.086. [PMID: 21843938]
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  • Cristiane Pimentel Victório, Marcos Vinicius Leal-Costa, Eliana Schwartz Tavares, Ricardo Machado Kuster, Celso Luiz Salgueiro Lage. Effects of supplemental UV-A on the development, anatomy and metabolite production of Phyllanthus tenellus cultured in vitro. Photochemistry and photobiology. 2011 May; 87(3):685-9. doi: 10.1111/j.1751-1097.2011.00905.x. [PMID: 21275997]
  • Kyoung Ah Kang, In Kyung Lee, Rui Zhang, Mei Jing Piao, Ki Cheon Kim, Sang Young Kim, Taekyun Shin, Bum Joon Kim, Nam Ho Lee, Jin Won Hyun. Radioprotective effect of geraniin via the inhibition of apoptosis triggered by γ-radiation-induced oxidative stress. Cell biology and toxicology. 2011 Apr; 27(2):83-94. doi: 10.1007/s10565-010-9172-4. [PMID: 20680428]
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  • Hideyuki Ito, Ayumu Iguchi, Tsutomu Hatano. Identification of urinary and intestinal bacterial metabolites of ellagitannin geraniin in rats. Journal of agricultural and food chemistry. 2008 Jan; 56(2):393-400. doi: 10.1021/jf0726942. [PMID: 18163562]
  • Chien-Min Yang, Hua-Yew Cheng, Ta-Chen Lin, Lien-Chai Chiang, Chun-Ching Lin. The in vitro activity of geraniin and 1,3,4,6-tetra-O-galloyl-beta-D-glucose isolated from Phyllanthus urinaria against herpes simplex virus type 1 and type 2 infection. Journal of ethnopharmacology. 2007 Apr; 110(3):555-8. doi: 10.1016/j.jep.2006.09.039. [PMID: 17113739]
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