Bioactivity and Structure–Activity Relationship of Epigallocatechin and Epigallocatechin-3-Gallate Derivatives

Araldi GL, Hwang YW (2022) Design, synthesis, and biological evaluation of polyphenol derivatives as DYRK1A inhibitors. Bioorg Med Chem Lett 64:128675. https://doi.org/10.1016/j.bmcl.2022.128675

Article  CAS  PubMed  PubMed Central  Google Scholar 

Chen M, Yu S (2017) Lipophilized grape seed proanthocyanidin derivatives as novel antioxidants. J Agr Food Chem 65:1598–1605. https://doi.org/10.1021/acs.jafc.6b05609

Article  CAS  Google Scholar 

Chen D, Pamu S, Cui Q, Chan TH, Dou QP (2012) Novel epigallocatechin gallate (EGCG) analogs activate AMP-activated protein kinase pathway and target cancer stem cells. Bioorg Med Chem 20:3031–3037. https://doi.org/10.1016/j.bmc.2012.03.002

Article  CAS  PubMed  PubMed Central  Google Scholar 

Chen W, Zhou C, Chen J, Wang M, Zhou F, Wang C, Zhang X, Zhou W (2022) Design and synthesis of epigallocatechin (EGC) analogs selective to inhibit α-amylase over α-glucosidases via the incorporation of caffeine acid and its derivatives. Bioorg Chem 119:105515. https://doi.org/10.1016/j.bioorg.2021.105515

Article  CAS  PubMed  Google Scholar 

Crous-Maso J, Palomeras S, Relat J, Camo C, Martinez-Garza U, Planas M, Feliu L, Puig T (2018) (-)-Epigallocatechin-3-gallate synthetic analogues inhibit fatty acid synthase and show anticancer activity in triple negative breast cancer. Molecules 23(:1160. https://doi.org/10.3390/molecules23051160

Dell’Agli M, Bellosta S, Rizzi L, Galli G, Canavesi M, Rota F, Parente R, Bosisio E, Romeo S (2005) A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate. Cell Mol Life Sci 62:2896–2903. https://doi.org/10.1007/s00018-005-5422-7

Article  CAS  PubMed  PubMed Central  Google Scholar 

Dodo K, Minato T, Noguchi-Yachide T, Suganuma M, Hashimoto Y (2008) Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate. Bioorg Med Chem 16:7975–7982. https://doi.org/10.1016/j.bmc.2008.07.063

Article  CAS  PubMed  Google Scholar 

Dodo K, Minato T, Hashimoto Y (2009) Structure-activity relationship of bis-galloyl derivatives related to (-)-epigallocatechin gallate. Chem Pharm Bull 57:190–194. https://doi.org/10.1248/cpb.57.190

Article  CAS  Google Scholar 

Ferrari E, Bettuzzi S, Naponelli V (2022) The potential of epigallocatechin gallate (EGCG) in targeting autophagy for cancer treatment: a narrative review. Int J Mol Sci 23:6075. https://doi.org/10.3390/ijms23116075

Article  CAS  PubMed  PubMed Central  Google Scholar 

Ferreira N, Cardoso I, Domingues MR, Vitorino R, Bastos M, Bai G, Saraiva MJ, Almeida MR (2009) Binding of epigallocatechin-3-gallate to transthyretin modulates its amyloidogenicity. FEBS Lett 583:3569–3576. https://doi.org/10.1016/j.febslet.2009.10.062

Article  CAS  PubMed  Google Scholar 

Ferreira N, Saraiva MJ, Almeida MR (2012) Epigallocatechin-3-gallate as a potential therapeutic drug for ttr-related amyloidosis: “in vivo” evidence from FAP mice models. PLoS ONE 7:e29933. https://doi.org/10.1371/journal.pone.0029933

Article  CAS  PubMed  PubMed Central  Google Scholar 

Furuta T, Hirooka Y, Abe A, Sugata Y, Ueda M, Murakami K, Suzuki T, Tanaka K, Kan T (2007) Concise synthesis of dideoxy-epigallocatechin gallate (DO-EGCG) and evaluation of its anti-influenza virus activity. Bioorg Med Chem Lett 17:3095–3098. https://doi.org/10.1016/j.bmcl.2007.03.041

Article  CAS  PubMed  Google Scholar 

Gonzalez-Alfonso JL, Penalver P, Ballesteros AO, Morales JC, Piou FJ (2019) Effect of alpha-glucosylation on the stability, antioxidant properties, toxicity, and neuroprotective activity of (-)-epigallocatechin gallate. Front Nutr 6:30. https://doi.org/10.3389/fnut.2019.00030

Article  CAS  PubMed  PubMed Central  Google Scholar 

Ha T, Kim MK, Park KS, Jung W, Choo H, Chong Y (2018) Structural modification of (-)-epigallocatechin gallate (EGCG) shows significant enhancement in mitochondrial biogenesis. J Agr Food Chem 66:3850–3859. https://doi.org/10.1021/acs.jafc.8b00364

Article  CAS  Google Scholar 

Huang Y, Cuan X, Yang X, Zhu W, Zhao Y, Jiang L, Zi C, Wang X, Sheng J (2022) Oxidized tea polyphenol (OTP-3) targets EGFR synergistic nimotuzumab at inhibition of non-small cell lung tumor growth. Bioorg Chem 128:106084. https://doi.org/10.1016/j.bioorg.2022.106084

Article  CAS  PubMed  Google Scholar 

Huo C, Yang H, Cui QC, Dou QP, Chan TH (2010) Proteasome inhibition in human breast cancer cells with high catechol-O-methyltransferase activity by green tea polyphenol EGCG analogs. Bioorg Med Chem 18:1252–1258. https://doi.org/10.1016/j.bmc.2009.12.034

Article  CAS  PubMed  Google Scholar 

Jeong GH, Cho JH, Jo C, Park S, Kim SB, Kim TH (2020) Novel hybrid molecules based on (-)-epigallocatechin gallate as potent anti-adipogenic agents. Chem Pharm Bull 68:1155–1162. https://doi.org/10.1248/cpb.c20-00229

Article  CAS  Google Scholar 

Jiang C, Wang L, Huang X, Zhu S, Ma C, Wang H (2021) Identification and antioxidant abilities of enzymatic-transesterification (-)-epigallocatechin-3-O-gallate stearyl derivatives in non-aqueous systems. Antioxidants 10:1282. https://doi.org/10.3390/antiox10081282

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kazi A, Wang ZG, Kumar N, Falsetti SC, Chan TH, Dou QP (2004) Structure-activity relationships of synthetic analogs of (-)-epigallocatechin-3-gallate as proteasome inhibitors. Anticancer Res 24:943–954

CAS  PubMed  Google Scholar 

Khandelwal A, Hall JA, Blagg BSJ (2013) Synthesis and structure-activity relationships of EGCG analogues, a recently identified Hsp90 inhibitor. J Org Chem 78:7859–7884. https://doi.org/10.1021/jo401027r

Article  CAS  PubMed  PubMed Central  Google Scholar 

Kim J, Hanh NTT, Kim NM, Moon YH, Ha JM, Park N, Lee DG, Hwang KH, Park JS, Kim D (2016) Functional properties of novel epigallocatechin gallate glucosides synthesized by using dextransucrase from Leuconostoc mesenteroides B-1299CB4. J Agr Food Chem 64:9203–9213. https://doi.org/10.1021/acs.jafc.6b04236

Article  CAS  Google Scholar 

Ko CH, Siu WS, Wong HL, Shum WT, Fung KP, Lau CBS, Leung PC (2011) Pro-bone and antifat effects of green tea and its polyphenol, epigallocatechin, in rat mesenchymal stem cells in vitro. J Agr Food Chem 59:9870–9876. https://doi.org/10.1021/jf202015t

Article  CAS  Google Scholar 

Kok SHL, Wong RSM, Gambari R, Cheung F, Lam WS, Lau FY, Cheng GTM, Cheng CH, Lam KM, Chan SH, Tang JCO, Chu CH, Ho KP (2008) In vitro cytotoxicity of (-)-EGCG octaacetate on MDAMB-231 and SKHep-1 human carcinoma cells. Int J Mol Med 22:841–845. https://doi.org/10.3892/ijmm_00000093

Article  CAS  PubMed  Google Scholar 

Kothari M, Kannan K, Sahadevan R, Sadhukhan S (2024) Novel molecular hybrids of EGCG and quinoxaline: potent multi-targeting antidiabetic agents that inhibit α-glucosidase, α-amylase, and oxidative stress. Int J Biol Macromol 263:130175. https://doi.org/10.1016/j.ijbiomac.2024.130175

Article  CAS  PubMed  Google Scholar 

Lam WH, Kazi A, Kuhn DJ, Chow LMC, Chan ASC, Dou QP, Chan TH (2004) A potential prodrug for a green tea polyphenol proteasome inhibitor: evaluation of the peracetate ester of (-)-epigallocatechin gallate. Bioorg Med Chem 12:5587–5593. https://doi.org/10.1016/j.bmc.2004.08.002

Article  CAS  PubMed  Google Scholar 

Laudadio E, Mangano L, Minnelli C (2024) Chemical scaffolds for the clinical development of mutant-selective and reversible fourth-generation EGFR-TKIs in NSCLC. ACS Chem Biol 19:839–854. https://doi.org/10.1021/acschembio.4c00028

Article  CAS  PubMed  Google Scholar 

Lee F, Lim J, Reithofer MR, Lee SS, Chung JE, Hauser CAE, Kurisawa M (2015) Synthesis and bioactivity of a conjugate composed of green tea catechins and hyaluronic acid. Polym Chem 6:4462–4472. https://doi.org/10.1039/C5PY00495K

Article  CAS  Google Scholar 

Lin SF, Lin YH, Lin M, Kao YF, Wang RW, Teng LW, Chuang SH, Chang JM, Yuan TT, Fu KC, Huang KP, Lee YS, Chiang CC, Yang SC, Lai CL, Liao CB, Chen P, Lin YS, Lai KT, Huang HJ, Yang JY, Liu CW, Wei WY, Chen CK, Hiipakka RA, Liao S, Huang JJ (2010) Synthesis and structure-activity relationship of 3-O-acylated (-)-epigallocatechins as 5α-reductase inhibitors. Eur J Med Chem 45:6068–6076. https://doi.org/10.1016/j.ejmech.2010.10.011

Article  CAS 

Comments (0)

No login
gif