Phenolic compounds from cultivated Glycyrrhiza uralensis and their PD-1/PD-L1 inhibitory activities

References

• Achenbach H, Stöcker M, A. Constenla M. 1988. Constituents of tropical medicinal plants. Part 31. Flavonoid and other constituents of Bauhinia manca. Phytochemistry. 27(6):1835–1841.
   Web of Science ®Google Scholar
• Bharadwaj DK, Murari R, Seshadri TR, Singh R. 1976. Occurrence of 2-methylisoflavones in Glycyrrhiza glabra. Phytochemistry. 15(2):352–353.
   Web of Science ®Google Scholar
• Cho HJ, Lim SS, Lee YS, Kim J-S, Lee CH, Kwon DY, Park JHY. 2010. Hexane/ethanol extract of Glycyrrhiza uralensis licorice exerts potent anti-inflammatory effects in murine macrophages and in mouse skin. Food Chem. 121(4):959–966.
   Web of Science ®Google Scholar
• Coombs MRP, Harrison ME, Hoskin DW. 2016. Apigenin inhibits the inducible expression of programmed death ligand 1 by human and mouse mammary carcinoma cells. Cancer Letters. 380(2):424–433.
   PubMed Web of Science ®Google Scholar
• Demizu S, Kajiyama K, Takahashi K, Hiraga Y, Yamamoto S, Tamura Y, Okada K, Kinoshita T. 1988. Antioxidant and antimicrobial constituents of licorice: isolation and structure elucidation of a new benzofuran derivative. Chem Pharm Bull. 36(9):3474–3479.
   PubMed Web of Science ®Google Scholar
• Dong H, Gou YL, Cao SG, Chen SX, Sim KY, Goh SH, Kini RM. 1999. Eicosenones and methylated flavonols from Amomumkoenigii. Phytochemistry. 50(5):899–902.
   Web of Science ®Google Scholar
• Fukai T, Marumo A, Kaitou K, Kanda T, Terada S, Nomura T. 2002. Antimicrobial activity of licorice flavonoids against methicillin-resistant Staphylococcus aureus. Fitoterapia. 73(6):536–539.
   PubMed Web of Science ®Google Scholar
• Fukuchi K, Okudaira N, Adachi K, Odai-Ide R, Watanabe S, Ohno H, Yamamoto M, Kanamoto T, Terakubo S, Nakashima H, et al. 2016. Antiviral and antitumor activity of licorice root extracts. In Vivo. 30(6):777–785.
   PubMed Web of Science ®Google Scholar
• Gou SH, Liu J, He M, Qiang Y, Ni JM. 2015. Quantification and bio-assay of α-glucosidase inhibitors from the roots of Glycyrrhiza uralensis Fisch. Nat Prod Res. 30(18):2130.
   PubMed Web of Science ®Google Scholar
• Han Y, Gao Y, He T, Wang D, Guo N, Zhang X, Chen S, Wang H. 2018. PD-1/PD-L1 inhibitor screening of caffeoylquinic acid compounds using surface plasmon resonance spectroscopy. Anal Biochem. 547:52.
   PubMed Web of Science ®Google Scholar
• Harborne JB, Greenham J, Williams CA, Eagles J, Markham KR. 1993. Ten isoprenylated and C-methylated flavonoids from the leaves of three Vellozia species. Phytochemistry. 34(1):219–226.
   Web of Science ®Google Scholar
• Hatano T, Aga Y, Shintani Y, Ito H, Okuda T, Yoshida T. 2000. Minor flavonoids from licorice. Phytochemistry. 55(8):959–963.
   PubMed Web of Science ®Google Scholar
• Hatano T, Fukuda T, Miyase T, Noro T, Okuda T. 1991. Phenolic constituents of licorice. III. Structures of glicoricone and licofuranone, and inhibitory effects of licorice constituents on monoamine oxidase. Chem Pharm Bull. 39(5):1238–1243.
   PubMed Web of Science ®Google Scholar
• Hatano T, Yasuhara T, Fukuda T, Noro T, Okuda T. 1989. Phenolic constituents of licorice. II. Structures of licopyranocoumarin, licoarylcoumarin and glisoflavone, and inhibitory effects of licorice phenolics on xanthine oxidase. Chem Pharm Bull. 37(11):3005.
   PubMed Web of Science ®Google Scholar
• Hong YY, Xuan DT, Quan WW. 2006. Studies on the HPLC Fingerprint of Radix Glycyrrhizae. Chin J Nat Medicines. 4:116–120.
   Google Scholar
• Hou J, Huang XC, Zhang JJ, Yang QH, Cao ZQ. 2008. [Quality Comparison of the Wild and Cultivated Glycyrrhiza of Xinjiang]. Science & Technology Information. 21:21–22.
   Google Scholar
• Hyoung Ja K, Seon Hee S, Byeong-Gon L, Sup LY. 2005. Identification of tyrosinase inhibitors from Glycyrrhiza uralensis. Planta Med. 71:785–787.
   PubMed Web of Science ®Google Scholar
• Lee JW, Ji YJ, Yu MH, Bo MHH, Seo HJ, Lee SP, Lee IS. 2009. Antimicrobial effect and resistant regulation of Glycyrrhiza uralensis on methicillin-resistant Staphylococcus aureus. Nat Prod Res. 23:101–111.
   PubMed Web of Science ®Google Scholar
• Ji S, Li Z, Song W, Wang Y, Liang W, Li K, Tang S, Wang Q, Qiao X, Zhou D, et al. 2016. Bioactive constituents of Glycyrrhiza uralensis (Licorice): Discovery of the effective components of a traditional herbal medicine. J Nat Prod. 79(2):281.
   PubMed Web of Science ®Google Scholar
• Kao TC, Wu CH, Yen GC. 2014. Bioactivity and potential health benefits of licorice. J Agric Food Chem. 62(3):542–553.
   PubMed Web of Science ®Google Scholar
• Khedri M, Abnous K, Rafatpanah H, Ramezani M. 2018. An optimized protocol for the in vitro generation and functional analysis of human PD1/PD-L1 signal. J Recept Signal Transduction. 38(1):31–36.
   PubMed Web of Science ®Google Scholar
• Kiuchi F, Chen X, Tsuda Y. 1990. Four new phenolic constituents from licorice (root of Glycyrrhiza sp.). Heterocycles. 31:629–636.
   Web of Science ®Google Scholar
• Li Q, Yin Y, Guo X, Chen M, Ren N, Liu C. 2014. Quality evaluation of traditional Chinese medicine Glycyrrhiza uralensis Fisch. in market. Zhonghua Zhongyiyao Xuekan. 32:587–590.
   Google Scholar
• Lien L-M, Lin K-H, Huang L-T, Tseng M-F, Chiu H-C, Chen R-J, Lu W-J. 2017. Licochalcone a prevents platelet activation and thrombus formation through the inhibition of PLCγ2-PKC, Akt, and MAPK pathways. Int J Mol Sci. 18(7):1500.
   Google Scholar
• Ma T-T, Gong M-X, He R, Wu S, Li J, Li Z-X, Lu Y, Xu Y-S, Ma T-T, Gong M-X. 2017. Study on correlation between color and effective components contents of Glycyrrhiza uralensis. Zhongguo Zhong Yao Za Zhi. 42:3776–3785.
   PubMedGoogle Scholar
• AsI MN, Hosseinzadeh H. 2008. Review of pharmacological effects of Glycyrrhiza sp. and its bioactive compounds. Phytotherapy Res. 22:709–724.
   PubMed Web of Science ®Google Scholar
• Eerdunbayaer, Orabi MAA, Hiroe A, Teruo K, Tsutomu H. 2014. Structures of new phenolics isolated from licorice, and the effectiveness of licorice phenolics on vancomycin-resistant Enterococci. Molecules. 19:13027–13041.
   PubMed Web of Science ®Google Scholar
• Saitoh T, Noguchi H, Shibata S. 1978. Chemical studies on the Oriental plant drugs. XLIV. A new isoflavone and the corresponding isoflavanone of licorice root. Chem Pharm Bull. 26(1):144–147.
   Web of Science ®Google Scholar
• Saitoh T, Shibata S. 1969. Chemical studies on the oriental plant drugs. XXII. Some new constituents of licorice root. (2). Glycyrol, 5-O-methylglycyrol and isoglycyrol . Chem Pharm Bull. 17(4):729–734.
   PubMed Web of Science ®Google Scholar
• Shan L, Yang N, Zhao Y, Sheng X, Yang S, Li Y. 2018. A rapid classification and identification method applied to the analysis of glycosides in Bupleuri radix and liquorice by ultra high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. J Sep Sci. 41(19):3791–3805.
   PubMed Web of Science ®Google Scholar
• Shiozawa T, Urata S, Kinoshita T, Saitoh T. 1989. Revised structures of glycyrol and isoglycyrol, constituents of the root of Glycyrrhiza uralensis. Chem Pharm Bull. 37(8):2239–2240.
   Web of Science ®Google Scholar
• Shults EE, Shakirov MM, Pokrovsky MA, Petrova TN, Pokrovsky AG, Gorovoy PG. 2016. Phenolic compounds from Glycyrrhiza pallidiflora Maxim. and their cytotoxic activity. Nat Prod Res. 31(4):445–452.
   PubMed Web of Science ®Google Scholar
• Won TH, Song IH, Kim KH, Yang WY, Lee SK, Oh DC, Oh KB, Shin J. 2015. Bioactive Metabolites from the Fruits of Psoralea corylifolia. J Nat Prod. 78(4):666–673.
   PubMed Web of Science ®Google Scholar
• Wang Q, Miao W-J, Xiang C, Guo D-A, Ye M. 2012. Chemical constituents from Glycyrrhiza uralensis. Zhongcaoyao. 43:1886–1890.
   Google Scholar
• Wang W, Zhao Y-Y, Liang H, Jia Q, Chen H-B. 2006. Coumestans from Hedysarum multijugum. J Nat Prod. 69(6):876–880.
   PubMed Web of Science ®Google Scholar
• Wittschier N, Faller G, Hensel A. 2009. Aqueous extracts and polysaccharides from Liquorice roots (Glycyrrhiza glabra L.) inhibit adhesion of Helicobacter pylori to human gastric mucosa. J Ethnopharmacol. 125(2):218–223.
   PubMed Web of Science ®Google Scholar
• Yin Y, Chen R, Zhang D, Qiao L, Li J, Wang R, Liu X, Yang L, Xie D, Zou J, et al. 2013. Regio-selective prenylation of flavonoids by plant cell suspension cultures of Cudrania tricuspidata and Morus alba. J Mol Catal B Enzym. 89:28–34.
   Google Scholar
• Zeng L, Fukai T, Nomura T, Zhang RY, Lou ZC. 1992. Phenolic constituents of Glycyrrhiza species. 8. Four new prenylated flavonoids, glyasperins A, B, C, and D from the roots of Glycyrrhiza aspera. Heterocycles. 34:575–587.
   Web of Science ®Google Scholar
• Zuo L, Li JB, Xu J, Yang JZ, Zhang DM, Tong YL. 2002. [Studies on chemical constituents in root of Isatis indigotica]. Chinese Traditional & Herbal Drugs. 32:688–691.
   Google Scholar