Potential Multifunctional Bioactive Compounds from Dysosma versipellis Explored by Bioaffinity Ultrafiltration-HPLC/MS with Topo I, Topo II, COX-2 and ACE2

References

• Liu CX, Zhang CN, He T, et al. Study on potential toxic material base and mechanisms of hepatotoxicity induced by Dysosma versipellis based on toxicological evidence chain (TEC) concept. Ecotoxicol Environ Saf. 2020;190:110073. doi:10.1016/j.ecoenv.2019.110073
   PubMed Web of Science ®Google Scholar
• Man SL, Gao WY, Wei CL, et al. Anticancer drugs from traditional toxic Chinese medicines. Phytother Res. 2012;26(10):1449–1465. doi:10.1002/ptr.4609
   PubMed Web of Science ®Google Scholar
• Tan XM, Zhou YQ, Zhou XL, et al. Diversity and bioactive potential of culturable fungal endophytes of Dysosma versipellis; a rare medicinal plant endemic to China. Sci Rep. 2018;8(1):5929. doi:10.1038/s41598-018-24313-2
   PubMed Web of Science ®Google Scholar
• Jiang RW, Zhou JR, Hon PM, et al. Lignans from Dysosma versipellis with inhibitory effects on prostate cancer cell lines. J Nat Prod. 2007;70(2):283–286. doi:10.1021/np060430o
   PubMed Web of Science ®Google Scholar
• Tang YJ, Zhao W, Li HM. Novel tandem biotransformation process for the biosynthesis of a novel compound, 4-(2,3,5,6-tetramethylpyrazine-1)-4’-demethylepipodophyllotoxin. Appl Environ Microbiol. 2011;77(9):3023–3034. doi:10.1128/AEM.03047-10
   PubMed Web of Science ®Google Scholar
• Yuan Y, Wang YZ, Xu R, et al. Application of ionic liquids in the microwave-assisted extraction of podophyllotoxin from Chinese herbal medicine. Analyst. 2011;136(11):2294–2305. doi:10.1039/c0an00864h
   PubMed Web of Science ®Google Scholar
• Zhou JT, Jiang XY, He SY, et al. Rational design of multitarget-directed ligands: strategies and emerging paradigms. J Med Chem. 2019;62(20):8881–8914. doi:10.1021/acs.jmedchem.9b00017
   PubMed Web of Science ®Google Scholar
• Zhang WL, Pei JF, Lai LH. Computational multitarget drug design. J Chem Inf Model. 2017;57(3):403–412. doi:10.1021/acs.jcim.6b00491
   PubMed Web of Science ®Google Scholar
• Korcsmáros T, Szalay MS, Böde C, et al. How to design multi-target drugs. Expert Opin Drug Discov. 2007;2(6):799–808.
   Google Scholar
• Malik V, Dhanjal JK, Kumari A, et al. Function and structure-based screening of compounds, peptides and proteins to identify drug candidates. Methods. 2017;131:10–21. doi:10.1016/j.ymeth.2017.08.010
   PubMed Web of Science ®Google Scholar
• Mulabagal V, Calderón AI. Development of an ultrafiltration-liquid chromatography/mass spectrometry (UF-LC/MS) based ligand-binding assay and an LC/MS based functional assay for Mycobacterium tuberculosis shikimate kinase. Anal Chem. 2010;82(9):3616–3621. doi:10.1021/ac902849g
   PubMed Web of Science ®Google Scholar
• Liang XX, Wu Q, Luan SX, et al. A comprehensive review of topoisomerase inhibitors as anticancer agents in the past decade. Eur J Med Chem. 2019;171:129–168. doi:10.1016/j.ejmech.2019.03.034
   PubMed Web of Science ®Google Scholar
• Sinha BK. Topoisomerase inhibitors. A review of their therapeutic potential in cancer. Drugs. 1995;49(1):11–19. doi:10.2165/00003495-199549010-00002
   PubMed Web of Science ®Google Scholar
• Delgado JL, Hsieh CM, Chan NL, et al. Topoisomerases as anticancer targets. Biochem J. 2018;475(2):373–398. doi:10.1042/BCJ20160583
   PubMed Web of Science ®Google Scholar
• Goradel NH, Najafi M, Salehi E, et al. Cyclooxygenase-2 in cancer: a review. J Cell Physiol. 2019;234(5):5683–5699. doi:10.1002/jcp.27411
   PubMed Web of Science ®Google Scholar
• Xu W, Huang YP, Zhang T, et al. Cyclooxygenase-2 gene polymorphisms and susceptibility to hepatocellular carcinoma: a meta-analysis based on 10 case-control studies. J Cancer Res Ther. 2018;14(8):S105–S113. doi:10.4103/0973-1482.172110
   PubMed Web of Science ®Google Scholar
• Mahboubi Rabbani SMI, Zarghi A. Selective COX-2 inhibitors as anticancer agents: a patent review (2014–2018). Expert Opin Ther Pat. 2019;29(6):407–427. doi:10.1080/13543776.2019.1623880
   PubMed Web of Science ®Google Scholar
• Gheblawi M, Wang K, Viveiros A, et al. Angiotensin-converting enzyme 2: SARS-CoV-2 receptor and regulator of the renin-angiotensin system: celebrating the 20th anniversary of the discovery of ACE2. Circ Res. 2020;126(10):1456–1474. doi:10.1161/CIRCRESAHA.120.317015
   PubMed Web of Science ®Google Scholar
• Hamming I, Cooper ME, Haagmans BL, et al. The emerging role of ACE2 in physiology and disease. J Pathol. 2007;212(1):1–11. doi:10.1002/path.2162
   PubMed Web of Science ®Google Scholar
• Luo LX, Qiu Q, Huang FF, et al. Drug repurposing against coronavirus disease 2019 (COVID-19): a review. J Pharm Anal. 2021;11(6):683–690. doi:10.1016/j.jpha.2021.09.001
   PubMed Web of Science ®Google Scholar
• Li YW, Zhou W, Yang L, et al. Physiological and pathological regulation of ACE2, the SARS-CoV-2 receptor. Pharmacol Res. 2020;157:104833. doi:10.1016/j.phrs.2020.104833
   PubMed Web of Science ®Google Scholar
• Kuba K, Imai Y, Ohto-Nakanishi T, et al. Trilogy of ACE2: a peptidase in the renin-angiotensin system, a SARS receptor, and a partner for amino acid transporters. Pharmacol Ther. 2010;128(1):119–128. doi:10.1016/j.pharmthera.2010.06.003
   PubMed Web of Science ®Google Scholar
• Xie L, Lee DY, Shang Y, et al. Characterization of spirostanol glycosides and furostanol glycosides from anemarrhenae rhizoma as dual targeted inhibitors of 5-lipoxygenase and cyclooxygenase-2 by employing a combination of affinity ultrafiltration and HPLC/MS. Phytomedicine. 2020;77:153284. doi:10.1016/j.phymed.2020.153284
   PubMed Web of Science ®Google Scholar
• Qin SS, Ren YR, Fu X, et al. Multiple ligand detection and affinity measurement by ultrafiltration and mass spectrometry analysis applied to fragment mixture screening. Anal Chim Acta. 2015;886:98–106. doi:10.1016/j.aca.2015.06.017
   PubMed Web of Science ®Google Scholar
• Choi Y, Jermihov K, Nam SJ, et al. Screening natural products for inhibitors of quinone reductase-2 using ultrafiltration LC-MS. Anal Chem. 2011;83(3):1048–1052. doi:10.1021/ac1028424
   PubMed Web of Science ®Google Scholar
• Chen GL, Xu YB, Wu JL, et al. Hypoglycemic and hypolipidemic effects of Moringa oleifera leaves and their functional chemical constituents. Food Chem. 2020;333:127478. doi:10.1016/j.foodchem.2020.127478
   PubMed Web of Science ®Google Scholar
• Xu YB, Chen GL, Guo MQ. Potential anti-aging components from Moringa oleifera leaves explored by affinity ultrafiltration with multiple drug targets. Front Nutr. 2022;9:854882. doi:10.3389/fnut.2022.854882
   PubMed Web of Science ®Google Scholar
• Vichai V, Kirtikara K. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat Protoc. 2006;1(3):1112–1116. doi:10.1038/nprot.2006.179
   PubMed Web of Science ®Google Scholar
• Feng HX, Chen GL, Zhang YL, et al. Potential multiple bioactive components from Sinopodophyllum hexandrum explored by affinity ultrafiltration with four drug targets. Phytomed Plus. 2021;2:100219. doi:10.1016/j.phyplu.2022.100219
   Google Scholar
• Shen MR, He Y, Shi SM. Development of chromatographic technologies for the quality control of traditional Chinese medicine in the Chinese pharmacopoeia. J Pharm Anal. 2021;11(2):155–162. doi:10.1016/j.jpha.2020.11.008
   PubMed Web of Science ®Google Scholar
• Liu YQ, He GH, Li HL, et al. Plasma pharmacokinetics and tissue distribution study of roemerine in rats by liquid chromatography with tandem mass spectrometry (LC-MS/MS). J Chromatogr B Analyt Technol Biomed Life Sci. 2014;969:249–255. doi:10.1016/j.jchromb.2014.08.031
   PubMed Web of Science ®Google Scholar
• Ghani NA, Ismail NH, Asakawa Y. Constituents of fermented male flowers of Alnus sieboldiana (Betulaceae). Nat Prod Commun. 2017;12(1):57–58.
   PubMed Web of Science ®Google Scholar
• Yang Y, Chen Y, Zhong ZY, et al. Validated LC-MS/MS assay for quantitative determination of deoxypodophyllotoxin in rat plasma and its application in pharmacokinetic study. J Pharm Biomed Anal. 2014;88:410–415. doi:10.1016/j.jpba.2013.09.027
   PubMed Web of Science ®Google Scholar
• Yang Z, Wu YQ, Wu SH. A combination strategy for extraction and isolation of multi-component natural products by systematic two-phase solvent extraction-(13) C nuclear magnetic resonance pattern recognition and following conical counter-current chromatography separation: podophyllotoxins and flavonoids from Dysosma versipellis (Hance) as examples. J Chromatogr A. 2016;1431:184–196. doi:10.1016/j.chroma.2015.12.074
   PubMed Web of Science ®Google Scholar
• Yao CX, Na N, Huang LY, et al. High-throughput detection of drugs binding to proteins using desorption electrospray ionization mass spectrometry. Anal Chim Acta. 2013;794:60–66. doi:10.1016/j.aca.2013.07.016
   PubMed Web of Science ®Google Scholar
• Xie LW, Fu QC, Shi SY, et al. Rapid and comprehensive profiling of α-glucosidase inhibitors in Buddleja Flos by ultrafiltration HPLC-QTOF-MS/MS with diagnostic ions filtering strategy. Food Chem. 2021;344:128651. doi:10.1016/j.foodchem.2020.128651
   PubMed Web of Science ®Google Scholar
• Chen GL, Guo MQ. Screening for natural inhibitors of topoisomerases I from Rhamnus davurica by affinity ultrafiltration and high-performance liquid chromatography-mass spectrometry. Front Plant Sci. 2017;8:1521. doi:10.3389/fpls.2017.01521
   PubMed Web of Science ®Google Scholar
• Chen GL, Wu JL, Li N, et al. Screening for anti-proliferative and anti-inflammatory components from Rhamnus davurica Pall. using bio-affinity ultrafiltration with multiple drug targets. Anal Bioanal Chem. 2018;410(15):3587–3595. doi:10.1007/s00216-018-0953-6
   PubMed Web of Science ®Google Scholar
• Xiao JQ, Gao MX, Sun Z, et al. Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: an update (2010–2020). Eur J Med Chem. 2020;208:112830. doi:10.1016/j.ejmech.2020.112830
   PubMed Web of Science ®Google Scholar
• Tabassum S, Zaki M, Afzal M, et al. New modulated design and synthesis of quercetin-CuII/ZnII-Sn2IV scaffold as anticancer agents: in vitro DNA binding profile, DNA cleavage pathway and Topo-I activity. Dalton Trans. 2013;42(27):10029–10041. doi:10.1039/c3dt50646k
   PubMed Web of Science ®Google Scholar
• Tang Q, Ji FL, Wang JY, et al. Quercetin exerts synergetic anti-cancer activity with 10-hydroxy camptothecin. Eur J Pharm Sci. 2017;109:223–232. doi:10.1016/j.ejps.2017.08.013
   PubMed Web of Science ®Google Scholar
• Zhang ZH, Chen S, Mei H, et al. Ginkgo biloba leaf extract induces DNA damage by inhibiting topoisomerase II activity in human hepatic cells. Sci Rep. 2015;5(1):14633. doi:10.1038/srep14633
   PubMed Web of Science ®Google Scholar
• Gowrishankar S, Muthumanickam S, Kamaladevi A, et al. Promising phytochemicals of traditional Indian herbal steam inhalation therapy to combat COVID-19 - an in silico study. Food Chem Toxicol. 2021;148:111966. doi:10.1016/j.fct.2020.111966
   PubMed Web of Science ®Google Scholar
• Guler HI, Tatar G, Yildiz O, et al. Investigation of potential inhibitor properties of ethanolic propolis extracts against ACE-II receptors for COVID-19 treatment by molecular docking study. Arch Microbiol. 2021;203(6):3557–3564. doi:10.1007/s00203-021-02351-1
   PubMed Web of Science ®Google Scholar
• Colunga Biancatelli RML, Berrill M, Catravas JD, et al. Quercetin and vitamin C: an experimental, synergistic therapy for the prevention and treatment of SARS-CoV-2 related disease (COVID-19). Front Immunol. 2020;11:1451. doi:10.3389/fimmu.2020.01451
   PubMed Web of Science ®Google Scholar
• Derosa G, Maffioli P, D’Angelo A, et al. A role for quercetin in coronavirus disease 2019 (COVID-19). Phytother Res. 2021;35(3):1230–1236. doi:10.1002/ptr.6887
   PubMed Web of Science ®Google Scholar
• Chen XQ, Wang ZX, Yang ZY, et al. Houttuynia cordata blocks HSV infection through inhibition of NF-κB activation. Antiviral Res. 2011;92(2):341–345. doi:10.1016/j.antiviral.2011.09.005
   PubMed Web of Science ®Google Scholar
• Cheng SC, Huang WC, Pang JHS, et al. Quercetin inhibits the production of IL-1β-induced inflammatory cytokines and chemokines in ARPE-19 cells via the MAPK and NF-κB signaling pathways. Int J Mol Sci. 2019;20(12):2957. doi:10.3390/ijms20122957
   PubMed Web of Science ®Google Scholar
• Fanunza E, Iampietro M, Distinto S, et al. Quercetin blocks Ebola virus infection by counteracting the VP24 interferon-inhibitory function. Antimicrob Agents Chemother. 2020;64(7):e00530–20. doi:10.1128/AAC.00530-20
   PubMed Web of Science ®Google Scholar
• Russo M, Moccia S, Spagnuolo C, et al. Roles of flavonoids against coronavirus infection. Chem Biol Interact. 2020;328:109211. doi:10.1016/j.cbi.2020.109211
   PubMed Web of Science ®Google Scholar