38.8.2.2 Medicinal Chemistry of Stable and Unstable 1,2-Dioxetanes: Origin, Formation, and Biological Activities

Abstract

This chapter describes the formation and transformation of stable and unstable 1,2-dioxetanes in various metabolic pathways. The chapter also describes the modern approaches to the synthesis of compounds with 1,2-dioxetane moiety, including molecules with chemiluminescence properties.

Key words

1,2-dioxetanes - peroxides - hydroperoxides - oxidation - singlet oxygen - cholesterol derivatives - vitamins - unsaturated compounds - oxidative cleavage - chemiluminescence

• 1 Liebman JF, Greer A. The Chemistry of Peroxides. Wiley; Hoboken, NJ 2006: 3

• 2 Tang Y, Dong Y, Vennerstrom JL. Med. Res. Rev. 2004; 24: 425

• 3 Liu D.-Z, Liu J.-K. Nat. Prod. Bioprospect. 2013; 3: 161

• 4 Egawa T, Fukuyama T, Yamamoto S, Kuchitsu K. J. Chem. Phys. 1987; 86: 6018

• 5 Allen FH. Acta Crystallogr., Sect. B 1984; 40: 64

• 6 Fujita S. J. Math. Chem. 2010; 47: 145

• 7 Sergeiko A, Poroikov VV, Hanuš LO, Dembitsky VM. Open Med. Chem. J. 2008; 2: 26

• 8 Namyslo JC, Kaufmann DE. Chem. Rev. 2003; 103: 1485

• 9 Dembitsky VM. Phytomedicine 2014; 12: 1559

• 10 Dembitsky VM. J. Nat. Med. 2008; 62: 1

• 11 Iriondo-Alberdi J, Greaney MF. Eur. J. Org. Chem. 2007; 4801

• 12 Antonsen S, Østby RB, Stenstrøm Y. Stud. Nat. Prod. Chem. 2018; 57: 1

• 13 Honga YJ, Tantillo DJ. Chem. Soc. Rev. 2014; 43: 5042

• 14 Xu Y, Conner ML, Brown MK. Angew. Chem. Int. Ed. 2015; 54: 11 918

• 15 Satomi T, Kusakabe H, Nakamura G, Nishio T, Uramoto M, Isono K. Agric. Biol. Chem. 1982; 46: 2621

• 16 Vil V, Terent’ev AO, Al Quntar AAA, Gloriozova TA, Savidov N, Dembitsky VM. Appl. Microbiol. Biotechnol. 2019; 103: 2449

• 17 This work was supported by the Russian Foundation for Basic Research (Grant No. 19–33–70067).

• 18 Green O, Eilon T, Hananya N, Gutkin S, Bauer CR, Shabat D. ACS Cent. Sci. 2017; 3: 349

• 19 Vacher M, Farahani P, Valentini A, Frutos LM, Karlsson HO, Galván IF, Lindh R. J. Phys. Chem. Lett. 2017; 8: 3790

• 20 Beck S, Köster H. Anal. Chem. 1990; 62: 2258

• 21 Pinto da Silva L, Esteves da Silva JC. ChemPhysChem 2012; 13: 2257

• 22 Xu X, Zhong J, Su Y, Zou Z, He Y, Hou X. Appl. Spectrosc. Rev. 2019; 54: 57

• 23 Nicolas JC, Terouanne B, Boussioux AM, Crastes de Paulet A. Ann. Biol. Clin. (Paris) 1985; 43: 201

• 24 Yan H, Lee S, Zhanga A, Yoon J. Org. Biomol. Chem. 2019; 17: 1389

• 25 Foote CS, Clennan EL, In: Active Oxygen in Chemistry Foote CS, Valentine J, Greenberg A, Liebman JF. Springer Dordrecht, The Netherlands 1995; 105-140

• 26 Barlow RB. Trends Pharmacol. Sci. 1979; 1: 109

• 27 Alabugin IV. Stereoelectronic Effects: A Bridge Between Structure and Reactivity. Wiley; Hoboken, NJ 2016

• 28 Alabugin IV, Bresch S, Gomes GP. J. Phys. Org. Chem. 2015; 28: 147

• 29 Kokh DB, Amaral M, Bomke J, Grädler U, Musil D, Buchstaller HP, Dreyer MK, Frech M, Lowinski M, Vallee F, Bianciotto M, Rak A, Wade RC. J. Chem. Theory Comput. 2018; 14: 3859

• 30 Leelananda SP, Lindert S. Beilstein J. Org. Chem. 2016; 12: 2694

• 31 Sliwoski G, Kothiwale S, Meiler J, Lowe Jr EW. Pharmacol. Rev. 2014; 66: 334

• 32 Bezhentsev VM, Druzhilovskiy DS, Ivanov SM, Filimonov DA, Sastry GN, Poroikov VV. Pharm. Chem. J. 2017; 51: 91

• 33 Lagunin AA, Goel RK, Gawande DY, Pahwa P, Gloriozova TA, Dmitriev AV, Ivanov SM, Rudik AV, Konova VI, Pogodin PV, Druzhilovsky DS, Poroikov VV. Nat. Prod. Rep. 2014; 31: 1585

• 34 Filimonov DA, Lagunin AA, Gloriozova TA, Rudik AV, Druzhilovskiy DS, Pogodin PV, Poroikov VV. Chem. Heterocycl. Compd. (Engl. Transl.) 2014; 50: 444

• 35 Filimonov DA, Druzhilovskiy DS, Lagunin AA, Gloriozova TA, Rudik AV, Dmitriev AV, Pogodin PV, Poroikov VV. Biomed. Chem. Res. Method. 2018; 1: e00 004

• 36 Vil VA, Gloriozova TA, Poroikov VV, Terent’ev AO, Savidov N, Dembitsky VM. Appl. Microbiol. Biotechnol. 2018; 102: 7657

• 37 Dembitsky VM, Savidov N, Gloriozova TA. Vietnam J. Chem. 2018; 56: 582

• 38 Dembitsky VM, Gloriozova TA. J. Nat. Prod. Res. 2017; 3: 147

• 39 Dembitsky VM, Gloriozova TA, Poroikov VV. Mini-Rev. Med. Chem. 2007; 7: 571

• 40 Dembitsky VM. Tetrahedron 2003; 59: 4701

• 41 Dembitsky VM. Eur. J. Med. Chem. 2008; 43: 223

• 42 Dembitsky VM. Med. Mycol. 2015; 1: 1

• 43 Dembitsky VM. J. Mol. Genet. Med. 2015; 9: 1

• 44 Krügener S, Schaper C, Krings U, Berger RG. Bioresour. Technol. 2009; 100: 2855

• 45 Cheng SY, Wang SK, Wen ZH, Dai CF, Duh CY. J. Asian Nat. Prod. Res. 2009; 11: 967

• 46 Romo J, Romo de Vivar A. Fortschr. Chem. Org. Naturst. 1967; 25: 90

• 47 Huanga J.-N, Zou Q, Chena J, Xu SH, Luo D, Zhang FG, Lu YY. Phytochem. Lett. 2018; 27: 114

• 48 Tiew P Bioactive Compounds from Mansonia gagei Drumm, PhD Thesis, Chulalongkorn University 2002 Accessed October 17, 2019 at: cuir.car.chula.ac.th/handle/123456789/2863

• 49 Tiew P, Takayama H, Kitajima M, Aimi N, Kokpola U, Chavasiri W. Tetrahedron Lett. 2003; 44: 6759

• 50 Wen R, Lv H, Jiang Y, Tu T. Bioorg. Med. Chem. Lett. 2018; 28: 1050

• 51 Liu Q.-F, Chen W.-L, Tang J, Zhao W.-M. Helv. Chim. Acta 2007; 90: 1745

• 52 Yang M, Zhang Y, Chen L, Chen Y. Nat. Prod. Res. 2018; 32: 1699

• 53 Liu W, Wu TC, Hong DM, Hu Y, Fan T, Guo WJ, Xu Q. Chin. J. Nat. Med. 2018; 16: 907

• 54 Lee T.-H, Lu CK, Kuo Y.-H, Lo J.-M, Lee CK. Helv. Chim. Acta 2008; 91: 79

• 55 Li H, Li L, Zheng Q, Kuroda C, Wang Q. Molecules 2012; 17: 5219

• 56 Chen WS, Chen YT, Wan XY, Friedrichs E, Puff H. Liebigs Ann. Chem. 1981; 10: 1880

• 57 Park S, Im SA, Kim KH, Lee CK. Immune Netw. 2011; 11: 412

• 58 Yaremenko IA, Vil VA, Demchuk DV, Terent’ev AO. Beilstein J. Org. Chem. 2016; 12: 1647

• 59 Vacher M, Galván IF, Ding BW, Schramm S, Berraud-Pache R, Naumov P, Ferré N, Liu YJ, Navizet I, Roca-Sanjuán D, Baader WJ, Lindh R. Chem. Rev. 2018; 118: 6927

• 60 Yin H, Xu L, Porter NA. Chem. Rev. 2011; 111: 5944

• 61 Vil’ VA, Yaremenko IA, Ilovaisky AI, Terent’ev AO. Molecules 2017; 22: 1881

• 62 Gelalcha FG. Chem. Rev. 2007; 107: 3338

• 63 Sono M, Roach MP, Coulter ED, Dawson JH. Chem. Rev. 1996; 96: 2841

• 64 Balci M. Chem. Rev. 1981; 81: 91

• 65 Khazem M, Jolly C, Gaslonde T, Massip S, Négrier P. Eur. J. Org. Chem. 2018; 5819

• 66 Rendic S, Guengerich FP. Chem. Res. Toxicol. 2015; 28: 38

• 67 Guengerich FP. Chem. Res. Toxicol. 2001; 14: 611

• 68 Isin EM, Guengerich FP. Biochim. Biophys. Acta 2007; 1770: 314

• 69 Miller WL, Auchus RJ. Endocr. Rev. 2011; 32: 81

• 70 Yoshimoto FK, Gonzalez E, Auchus RJ, Guengerich FP. J. Biol. Chem. 2016; 291: 17 143

• 71 Gonzalez E, Johnson KM, Pallan PS, Phan TTN, Zhang W, Lei L, Wawrzak Z, Yoshimoto FK, Egli M, Guengerich FP. J. Biol. Chem. 2018; 293: 541

• 72 Di Mascio P, Martinez GR, Miyamoto S, Ronsein GE, Medeiros MHG, Cadet J. Chem. Rev. 2019; 119: 2043

• 73 Di Mascio P, Martinez GR, Miyamoto S, Ronsein GE, Medeiros MHG, Cadet J. Arch. Biochem. Biophys. 2016; 595: 161

• 74 Alegria TG, Meireles DA, Cussiol JR, Hugo M, Trujillo M, de Oliveira MA, Miyamoto S, Queiroz RF, Valadares NF, Garratt RC, Radi R, Di Mascio P, Augusto O, Netto LE. Proc. Natl. Acad. Sci. U. S. A. 2017; 114: E132

• 75 Uemi M, Ronsein GE, Miyamoto S, Medeiros MHG, Di Mascio P. Chem. Res. Toxicol. 2009; 22: 875

• 76 Murphy RC, Johnson KM. J. Biol. Chem. 2008; 283: 15 521

• 77 Onyango AN. Oxid. Med. Cell. Longevity 2016; 2 398 573

• 78 Hasegawa H. J. Chromatogr. 1992; 605: 215

• 79 King JM, Min DB. J. Food Sci. 1998; 63: 31

• 80 Li TL, Min DB. J. Food Sci. 1998; 63: 413

• 81 Li T.-L, King JM, Min DB. J. Food Biochem. 2000; 24: 477

• 82 Bell RG, Stark P. Biochem. Biophys. Res. Commun. 1976; 72: 619

• 83 Dowd P, Ham SW, Naganathan S, Hershline R. Annu. Rev. Nutr. 1995; 15: 419

• 84 Daines AM, Payne RJ, Humphries ME, Abell AD. Curr. Org. Chem. 2003; 7: 1

• 85 Presnell SR, Stafford DW. Thromb. Haemostasis 2002; 87: 937

• 86 Pavić V, Jakovljević M, Molnar M, Jokić S. Plants 2019; 8: 16

• 87 Reuter J, Jocher A, Hornstein S, Mönting J, Schempp C. Planta Med. 2007; 73: 1190

• 88 Aruoma OI, Halliwell B, Aeschbach R, Löligers J. Xenobiotica 1992; 22: 257

• 89 Schwarz K, Ternes W. Z. Lebensm.-Unters. Forsch. 1992; 195: 99

• 90 Ninomiya K, Matsuda H, Shimoda H. Bioorg. Med. Chem. Lett. 2004; 14: 1943

• 91 Park JA, Kim S, Lee SY. NeuroReport 2008; 19: 1301

• 92 Petiwala SM, Johnson JJ. Cancer Lett. 2015; 367: 93

• 93 Liu X, Fu J, Yao XJ, Yang J, Liu L. J. Nat. Prod. 2018; 81: 1333

• 94 Manoharan S, Balakrishnan S, Vinothkumar V, Silvan S. Pharmacol. Rep. 2010; 62: 1170

• 95 Loussouarn M, Krieger-Liszkay A, Svilar L, Bily A, Birtić S, Havaux M. Plant Physiol. 2017; 175: 1381

• 96 Masuda T, Inaba Y, Maekawa T, Takeda Y, Tamura H, Yamaguchi H. J. Agric. Food Chem. 2002; 50: 5863

• 97 Gonzalez A, Rodriguez C, Luis J. J. Chem. Res. 1988; 114

• 98 Basnet P, Kadota S, Terashima S, Shimizu M, Namba T. Chem. Pharm. Bull. 1993; 41: 1238

• 99 Lee SH, Choi SY, Kim H, Hwang JS, Lee BG, Gao JJ, Kim SY. Biol. Pharm. Bull. 2002; 25: 1045

• 100 Wang L, Yang Y, Liu C, Chen RY. J. Asian Nat. Prod. Res. 2010; 12: 431

• 101 Celaje JA, Zhang D, Guerrero AM, Selke M. Org. Lett. 2011; 13: 4846

• 102 Prescott AG, John P. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1996; 47: 245

• 103 Bugg TDH. Tetrahedron 2003; 59: 7075

• 104 Bai J, Hou Q, Zhu W, Liu Y. Catal. Sci. Technol. 2019; 9: 444

• 105 Mazzone G, Alberto ME, Russoa N, Sicilia E. Phys. Chem. Chem. Phys. 2014; 16: 12 773

• 106 Imagawa T, Kasai S, Matsui K, Nakamura T. J. Biochem. (Tokyo) 1983; 94: 87

• 107 Imagawa T, Kasai S, Matsui K, Nakamura T. J. Biochem. (Tokyo) 1982; 92: 1109

• 108 Wilcox AL, Marnett L. J. Chem. Res. Toxicol. 1193; 6: 413

• 109 Loidl-Stahlhofen A, Hannemann K, Spiteller G. Biochim. Biophys. Acta 1994; 1213: 140

• 110 Timmins GS, dos Santos RE, Whitwood AC, Catalani LH, Di Mascio P, Gilbert BC, Bechara EJH. Chem. Res. Toxicol. 1997; 10: 1090

• 111 Pratt DA, Tallman KA, Porter NA. Acc. Chem. Res. 2011; 44: 458

• 112 Ghnimi S, Budilarto E, Kamal-Eldin A. Compr. Rev. Food Sci. Food Saf. 2017; 16: 1206

• 113 Valacchi G, Pecorelli A, Cervellati C, Hayek J. Free Radical Biol. Med. 2017; 111: 270

• 114 Wang W, Yang H, Johnson D, Gensler C, Decker E, Zhang G. Prostaglandins Other Lipid Mediators 2017; 132: 84

• 115 Pryor WA, Porter NA. Free Radical Biol. Med. 1990; 8: 541

• 116 Hu C, Wang M, Han X. Redox Biol. 2017; 12: 946

• 117 Sottero B, Rossin D, Poli G, Biasi F. Curr. Med. Chem. 2018; 25: 1311

• 118 Xiao M, Zhong H, Xia L, Tao Y, Yin H. Free Radical Biol. Med. 2017; 111: 316

• 119 Barrera G, Pizzimenti S, Ciamporcero ES, Daga M, Ullio C, Arcaro A, Cetrangolo GP, Ferretti C, Lepore A, Gentile F. Antioxid. Redox Signaling 2015; 22: 1681

• 120 Esterbauer H, Schaur RJ, Zollner H. Free Radical Biol. Med. 1991; 11: 81

• 121 Esterbauer H, Zollner H, Schaur RJ, In: Membrane Lipid Oxidation Vigo-Pelfrey C. CRC Press Boca Raton, FL 1989; 1

• 122 Kaur K, Salomon RG, O’Neil J, Hoff HF. Chem. Res. Toxicol. 1997; 10: 1387

• 123 Mueller MJ. Chem. Biol. 1998; 5: R323

• 124 Tallima H, Rashika ER. J. Adv. Res. 2018; 11: 33

• 125 Li B, Gao G, Zhang W, Li B, Yang C, Jiang X, Tian Y, Liang H. Mol. Med. Rep. 2018; 17: 6261

• 126 Sana MM, Shana RM, Hafez AS. J. Adv. Res. 2018; 11: 3

• 127 Dembitsky VM, Rozentsvet OA. Phytochemistry 1990; 29: 3149

• 128 Dembitsky VM, Srebnik M. Biochemistry (Moscow) 2002; 67: 1068

• 129 Dembitsky VM, Rozentsvet OA, Pechenkina EE. Phytochemistry 1990; 29: 3417

• 130 Dembitsky VM, Pechenkina-Shubina EE, Rozentsvet OA. Phytochemistry 1991; 30: 2279

• 131 Dembitsky VM. Lipids 2006; 41: 309

• 132 Wells ML, Potin P, Craigie JS, Raven JA, Merchant SS, Helliwell KE, Smith AG, Camire ME, Brawley SH. J. Appl. Phycol. 2017; 29: 949

• 133 Khotimchenko SV, Vaskovsky VE, Titlyanova T. Bot. Mar. 2002; 45: 17

• 134 Dembitsky VM, Rozentsvet OA. Phytochemistry 1989; 28: 3341

• 135 Dembitsky VM, Shkrob I, Rozentsvet OA. Phytochemistry 2000; 54: 965

• 136 Pereira H, Barreira L, Figueiredo F, Custódio L, Vizetto-Duarte C, Polo C, Rešek E, Engelen A, Varela J. Mar. Drugs 2012; 10: 1920

• 137 Monroig O, Tocher DR, Navarro JC. Mar. Drugs 2013; 11: 3998

• 138 Hanuš LO, Levitsky DO, Shkrob I, Dembitsky VM. Food Chem. 2009; 116: 491

• 139 Dembitsky VM, Řezanka T, Spížek J, Hanuš LO. Phytochemistry 2005; 66: 747

• 140 Tocher DR. Aquacult. Res. 2010; 41: 717

• 141 Huang TH, Wang PW, Yang SC, Chou WL, Fang JY. Mar. Drugs 2018; 16: E256

• 142 Lien EL, Richard C, Hoffman DR. Prostaglandins, Leukotrienes Essent. Fatty Acids 2018; 128: 26

• 143 Peebles Jr RS. Pharmacol. Ther. 2019; 193: 1

• 144 Das UN. J. Adv. Res. 2018; 11: 57

• 145 Wang L, Luo G, Zhang LF, Geng HX. Prostaglandins Other Lipid Mediators 2018; 138: 9

• 146 Roberts II LJ, Milne GL. J. Lipid Res. 2009; 50: S219

• 147 Kuehl Jr FA, Humes JL, Beveridge GC, Van Arman CG, Egan RW. Inflammation 1977; 2: 285

• 148 Rokach J, Khanapure SP, Hwang SW, Adiyama M, Lawson JA, FitzGerald GA. Prostaglandins 1997; 54: 823

• 149 Funk CD. Science (Washington, D. C.) 2000; 294: 1871

• 150 Sun X, Li Q. Int. J. Mol. Med. 2018; 42: 1203

• 151 Yin H, Havrilla CM, Gao L, Morrow JD, Porter NA. J. Biol. Chem. 2003; 278: 16 720

• 152 Cheng Y, Austin SC, Rocca B, Koller J, Coffman TM, Grosser T, Lawson JA, FitzGerald GA. Science (Washington, D. C.) 2000; 296: 539

• 153 Porter NA, In: Free Radicals in Biology Pryor WA. Academic New York 1980; IV. 261

• 154 Roberts II LJ, Brame CJ, Chen Y, Morrow JD. Methods Mol. Biol. 1999; 120: 257

• 155 Davì G, Santilli F, Vazzana N. Handb. Exp. Pharmacol. 2012; 210: 261

• 156 Morrow JD, Harris TM, Roberts II LJ. Anal. Biochem. 1990; 184: 1

• 157 Morrow JD, Hill KE, Burk RF, Nammour TM, Badr KF, Roberts II LJ. Proc. Natl. Acad. Sci. U. S. A. 1990; 87: 9383

• 158 Yin H, Havrilla CM, Morrow JD, Porter NA. J. Am. Chem. Soc. 2002; 124: 7745

• 159 Morrow JD, Roberts II LJ. Methods Enzymol. 1999; 300: 3

• 160 Fam SS, Morrow JD. Curr. Med. Chem. 2003; 10: 1723

• 161 Lawson JA, Rokach J, FitzGerald GA. J. Biol. Chem. 1999; 274: 24 441

• 162 Carotenoids Handbook. Britton G, Liaaen-Jensen S, Pfander H. Birkhäuser; Basel 2004

• 163 Kiokias S, Proestos C, Varzakas T. Curr. Res. Nutr. Food Sci. 2016; 4: 25

• 164 Dembitsky VM, Maoka T. Prog. Lipid Res. 2007; 46: 328

• 165 Vishal B, Kumar PP. Front. Plant Sci. (New Haven, CT, U. S.). 2018; 9: 838

• 166 Tarkowská D, Strnad M. Planta 2018; 247: 1051

• 167 Shu K, Luo X, Meng Y, Yang W. Plant Cell Physiol. 2018; 59: 215

• 168 Clark KB, Howard JA, Oyler AJ. J. Am. Chem. Soc. 1997; 119: 9560

• 169 Oyler AJ, Motto MG, Naldi RE, Facchine KL, Hamburg PF, Burinsky DJ, Dunphy R, Cotter ML. Tetrahedron 1989; 45: 7679

• 170 Napoli JL, In: Encyclopedia of Biological Chemistry Lennarz WJ, Lane MD. Elsevier Oxford 2004; 4. 354

• 171 Tsujimoto K, Hozoji H, Ohashi M, Watanabe M, Hattori H. Chem. Lett. 1984; 13: 1673

• 172 Baron MH, Coulange MJ, Coupry C, Baron D, Favrot J, Abo-Aly MM. Photochem. Photobiol. 1989; 49: 736

• 173 Crank G, Pardijanto MS. J. Photochem. Photobiol., A 1995; 8: 93

• 174 Mousseron-Canet M. Methods Enzymol. 1971; 18: 591

• 175 Ponce MA, Ramirez JA, Galagovsky LR, Gros EG, Erra-Balsells R. Photochem. Photobiol. Sci. 2002; 1: 749

• 176 Hu X, White KM, Jacobsen NE, Mangelsdorf DJ, Canfield LM. J. Nutr. Biochem. 1998; 9: 567

• 177 Nishino A, Maoka T, Yasui H. Tetrahedron Lett. 2016; 57: 1967

• 178 Doering W, Sarma K. J. Am. Chem. Soc. 1992; 114: 6037

• 179 Mordi RC. Biochem. J. 1993; 292: 310

• 180 Terao J, Minami Y, Bando N. J. Clin. Biochem. Nutr. 2011; 48: 57

• 181 Kim YS, Oh DK. Appl. Microbiol. Biotechnol. 2010; 88: 807

• 182 Devery J, Milborrow BV. Br. J. Nutr. 1994; 72: 397

• 183 Kim YS, Kim NH, Kim HJ, Lee JK, Kim SW, Oh DK. Appl. Microbiol. Biotechnol. 2007; 76: 1339

• 184 During A, Harrison EH. Arch. Biochem. Biophys. 2004; 430: 77

• 185 Lascano S, Lopez M, Arimondo PB. Chem. Rec. 2018; 18: 1854

• 186 Fischer N, Seo EJ, Efferth T. Phytomedicine 2018; 47: 192

• 187 Rauf A, Imran M, Khan IA, Ur-Rehman M, Gilani SA, Mehmood Z, Mubarak MS. Phytother. Res. 2018; 32: 2109

• 188 Dall’Acqua F, In: Trends in Photobiology Hélène C, Charlier M, Montenay-Garestier T, Laustriat G. Springer Boston, MA 1982;

• 189 CRC Handbook of Photochemistry and Photobiology. Horspool WH, Lenci F. CRC Press; Boca Raton, FL 2003

• 190 Viola G, Vedaldi D, Dall’Acqua F, Lampronti I, Bianchi N, Zuccato C, Borgatti M, Gambari R. J. Photochem. Photobiol., B 2008; 92: 24

• 191 Abu-Hashem AA. Am. J. Org. Chem. 2015; 5: 14

• 192 Maslov SA, Blyumberg EA. Russ. Chem. Rev. (Engl. Transl.) 1976; 45: 155

• 193 Zhuravel NN, Belichenko IV, Kyagova AA, Lysenko EP, Khalilov EM, Potapenko AY. Biochemistry (Moscow) Suppl. Ser. A: Membr. Cell Biol. 1996; 10: 381

• 194 Marley KA, Larson RA. Photochem. Photobiol. 1994; 59: 503

• 195 Brito AF, Ribeiro M, Abrantes AM, Pires AS, Teixo RJ, Tralhao JG, Botelho MF. Curr. Med. Chem. 2015; 22: 3025

• 196 Osman A, Makris DP, Kefalas P. Process Biochem. 2008; 43: 861

• 197 Sokolová R, Ramešová Š, Degano I, Hromadová M, Gála M, Žabka J. Chem. Commun. (Cambridge) 2012; 48: 3433

• 198 Zenkevich IG, Eshchenko AY, Makarova SV, Vitenberg AG, Dobryakov YG, Utsal VA. Molecules 2007; 12: 654

• 199 Fiorucci S, Golebiowski J, Cabrol-Bass D, Antonczak S. ChemPhysChem 2004; 5: 1726

• 200 Kano K, Mabuchi T, Uno B, Esaka Y, Tanaka T, Linuma M. J. Chem. Soc., Chem. Commun. 1994; 593

• 201 Tournaire C, Croux S, Maurette MT, Beck I, Hocquaux M, Braun AM, Oliveros E. J. Photochem. Photobiol., B 1993; 19: 205

• 202 Ralston L, Subramanian S, Matsuno M, Yu O. Plant Physiol. 2005; 137: 1375

• 203 Falcone Ferreyra ML, Rius SP, Casati P. Front. Plant Sci. (New Haven, CT, U. S.) 2012; 3: 222

• 204 Wong E. Phytochemistry 1987; 26: 1544

• 205 Wong E, Wilson JM. Phytochemistry 1976; 15: 1325

• 206 Bell C, Hawthorne S. J. Pharm. Pharmacol. 2008; 60: 139

• 207 García-Niño WR, Zazueta C. Pharmacol. Res. 2015; 97: 84

• 208 Derosa G, Maffioli P, Sahebkar A. Adv. Exp. Med. Biol. 2016; 928: 473

• 209 Zeb A. Mol. Cell. Biochem. 2018; 448: 27

• 210 Daniel EM, Krupnick AS, Heur Y.-H, Blinzler JA, Nims RW, Stoner GD. J. Food Compos. Anal. 1989; 2: 338

• 211 Ríos JL, Giner RM, Marín M, Recio MC. Planta Med. 2018; 84: 1068

• 212 Häkkinen S, Heinonen M, Kärenlampi S, Mykkänen H, Ruuskanen J, Törrönen R. Food Res. Int. 1999; 32: 345

• 213 Vattem DA, Shetty K. J. Food Biochem. 2005; 29: 234

• 214 Tokutomi H, Takeda T, Hoshino N, Akutagawa T. ACS Omega 2018; 3: 11 179

• 215 Silva AF, Oliveira Jr VX, Silva LS, Pinheiro AAS, Ciscato LFML. Bioorg. Med. Chem. Lett. 2016; 26: 5007

• 216 Chen Y, Spiering AJH, Karthikeyan S, Peters GWM, Meijer EW, Sijbesma RP. Nat. Chem. 2012; 4: 559

• 217 Andronico LA, Quintavalla A, Lombardo M, Mirasoli M, Guardigli M, Trombini C, Roda A. Chem.–Eur. J. 2016; 22: 18 156

• 218 Sun J, Hu Z, Wang R, Zhang S, Zhang X. Anal. Chem. 2019; 91: 1384

• 219 Cao J, An W, Reeves AG, Lippert AR. Chem. Sci. 2018; 9: 2552

• 220 An W, Mason RP, Lippert AR. Org. Biomol. Chem. 2018; 16: 4176

• 221 Hisamatsu S, Suzuki S, Kohmoto S, Kishikawa K, Yamamoto Y, Motokawa R, Yaita T. Tetrahedron 2017; 73: 3993

• 222 Turan IS, Yilmaz O, Karatas B, Akkaya EU. RSC Adv. 2015; 5: 34 535

• 223 Watanabe N, Hiragaki K, Tsurumi K, Ijuin HK, Matsumoto M. Tetrahedron 2017; 73: 1845

• 224 Watanabe N, Kikuchi M, Maniwa Y, Ijuin HK, Matsumoto M. J. Org. Chem. 2010; 75: 879

• 225 Gnaim S, Shabat D. J. Am. Chem. Soc. 2017; 139: 10 002

• 226 Roth-Konforti ME, Bauer CR, Shabat D. Angew. Chem. Int. Ed. 2016; 55: 1445

• 227 Hananya N, Boock AE, Bauer CR, Satchi-Fainaro R, Shabat D. J. Am. Chem. Soc. 2016; 138: 13 438

• 228 Seven O, Sozmen F, Turan IS. Sens. Actuators, B 2017; 239: 1318

• 229 Turan IS, Sozmen F. Sens. Actuators, B 2014; 201: 13

• 230 Cao J, Lopez R, Thacker JM, Moon JY, Jiang C, Morris SNS, Bauer JH, Tao P, Mason RP, Lippert AR. Chem. Sci. 2015; 6: 1979

• 231 Green O, Gnaim S, Blau R, Eldar-Boock A, Satchi-Fainaro R, Shabat D. J. Am. Chem. Soc. 2017; 139: 13 243

• 232 Ciscato LFML, Weiss D, Beckert R, Baader WJ. J. Photochem. Photobiol., A 2011; 218: 41

• 233 Yu L, Ren L, Yi R, Guo R. Synth. Commun. 2011; 41: 2530

• 234 Bastos EL, Farahani P, Bechara EJH, Baader WJ. J. Phys. Org. Chem. 2017; 30: e3725

• 235 Bartoloni FH, de Oliveira MA, Augusto FA, Ciscato LFML, Bastos EL, Baader WJ. J. Braz. Chem. Soc. 2012; 23: 2093

• 236 Kindt S, Jasch H, Heinrich MR. Chem.–Eur. J. 2014; 20: 6251