Furanocoumarins in anticancer therapy – For and against

Amicis, 2015, Bergapten drives autophagy through the up-regulation of PTEN expression in breast cancer cells, Mol. Cancer, 14, 130, 10.1186/s12943-015-0403-4 Asif, 2015, Pharmacologically potentials of different substituted coumarin derivatives, Chem. Int., 1, 1 Bądziul, 2014, Combined treatment with quercetin and imperatorin as a potent strategy for killing HeLa and Hep-2 cells, Mol. Cell. Biochem., 392, 213, 10.1007/s11010-014-2032-4 Bethea, 1999, Psoralen photobiology and photochemotherapy: 50 years of science and medicine, J. Dermatol. Sci., 19, 78, 10.1016/S0923-1811(98)00064-4 Bruni, 2019, Botanical sources, chemistry, analysis, and biological activity of furanocoumarins of pharmaceutical interest, Molecules, 24, 10.3390/molecules24112163 Cheung, 2009, Liver injury associated with the use of Fructus Psoraleae (Bol-gol-zhee or Bu-gu-zhi) and its related propriety medicine, Clin. Toxicol., 47, 683, 10.1080/15563650903059136 Choochuay, 2013, Imperatorin sensitizes anoikis and inhibits anchorage-independent growth of lung cancer cells, J. Nat. Med., 67, 599, 10.1007/s11418-012-0719-y Dowdy, 2016, Melanoma risk from dietary furocoumarins: how much more evidence is required?, J. Clin. Oncol., 34, 636, 10.1200/JCO.2015.63.8643 Edelson, 1987, Treatment of cutaneous T-cell lymphoma by extracorporeal photochemotherapy. Preliminary results, The New Eng J Med, 316, 297, 10.1056/NEJM198702053160603 El-Domyati, 2013, Evaluation of apoptosis regulatory proteins in response to PUVA therapy for psoriasis, Photoderm Photoimmun Photomed, 29, 18, 10.1111/phpp.12012 Escarega, 2007, The transcription nuclear factor-kappa B and cancer, Clinic Oncol (R Coll Radiol), 19, 154, 10.1016/j.clon.2006.11.013 Fang, 2010, Isolation and identification of bergapten in dry root of Glehnia littoralis and preliminary determination of its antitumor activity in vitro, J Plant Res Envir, 19, 95 Fracarolli, 2016, Inactivation of plant-pathogenic fungus Colletotrichum acutatum with natural plant-produced photosensitizers under solar radiation, J. Photochem. Photobiol. B, 162, 402, 10.1016/j.jphotobiol.2016.07.009 Francisco, 2012, Synthesis of novel benzofurocoumarin analogues and their antiproliferative effect on human cancer cell lines, Eur. J. Med. Chem., 47, 370, 10.1016/j.ejmech.2011.11.005 Francisco, 2013, Synthesis of novel psoralen analogues and their in vitro antitumor activity, Bioorg. Med. Chem., 21, 5047, 10.1016/j.bmc.2013.06.049 Fujioka, 1999, Antiproliferative constituents from Umbelliferae plants. V. a new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica, Chem Pharm Bull, 47, 96, 10.1248/cpb.47.96 Gawron, 1987, Cytostatic activity of coumarins in vitro, Planta Med., 53, 526, 10.1055/s-2006-962801 Gorgus, 2010, Limettin and furanocoumarins in beverages conteining citrus juices or extracts, Food Chem. Toxicol., 48, 93, 10.1016/j.fct.2009.09.021 Holtick, 2012, In vitro PUVA treatment preferentially induces apoptosis in alloactivated T cells, Transplantation., 94, e31, 10.1097/TP.0b013e31825f4454 Hsieh, 2014, Psoralen reverses docetaxel-induced multidrug resistance in A549/D16 human lung cancer cells lines, Phytomedicine, 21, 970, 10.1016/j.phymed.2014.03.008 Hu, 2016, Imperatorin acts as a cisplatin sensitizer via downregulating Mcl-1 expression in HCC chemotherapy, Tumor Biol., 37, 331, 10.1007/s13277-015-3591-z Hung, 2017, Chemistry and health effects of furanocoumarins in grapefruit, J. Food Drug Anal., 25, 71, 10.1016/j.jfda.2016.11.008 Jakubowicz-Gil, 2012, Cell death in HeLa cells upon imperatorin and cisplatin treatment, Folia Histochem. Cytobiol., 50, 381, 10.5603/FHC.2012.0052 Kang, 2005, Effect of isoimperatorin on the proliferation of prostate cancer cell line du145 cells, Biomol. Ther., 13, 185 Kim, 2007, Antiproliferative effect of furanocoumarins from the root of Angelica dahurica on cultured human tumor cell lines, Phytother. Res., 21, 288, 10.1002/ptr.2043 Kirsch, 2016, Natural and synthetic coumarins with effects on inflammation, Molecules, 21, 1322, 10.3390/molecules21101322 Ko, 2018, Pharmacological utilization of bergamottin, derived from grapefruits, in cancer prevention and therapy, Int. J. Mol. Sci., 19, 10.3390/ijms19124048 Koul, 2019, Genus Psoralea: a review of the traditional and modern uses, phytochemistry and pharmacology, J. Ethnopharmacol., 32, 201, 10.1016/j.jep.2018.11.036 Kozioł, 2016, Imperatorin–pharmacological meaning and analytical clues:profound investigation, Phytochem. Rev., 15, 627, 10.1007/s11101-016-9456-2 Kubrak, 2017, Natural and synthetic coumarins and their pharmacological activity, Eur J Clin Exp Med, 15, 169, 10.15584/ejcem.2017.2.12 Lampronti, 2009, Increase in gamma-globin mRNA content in human erythroid cells treated with angelicin analogs, Int. J. Hematol., 90, 318, 10.1007/s12185-009-0422-2 Lee, 1994, In vitro photoinduced cytotoxicity and DNA binding properties of psoralen and coumarin, J. Med. Chem., 37, 1208, 10.1021/jm00034a019 Lee, 2003, Effect of 5-methoxypsoralen (5-MOP) on cell apoptosis and cell cycle in human hepatocellular carcinoma cell line, Toxicol. in Vitro, 17, 279, 10.1016/S0887-2333(03)00014-6 Li, 2019, Acute liver failure associated with Fructus Psoraleae: a case report and literature review, BMC Complement. Altern. Med., 19, 10.1186/s12906-019-2493-9 Li, 2016, Angelicin inhibits human lung carcinoma A549 cell growth and migration through regulating JNK and ERK pathways, Oncol. Rep., 36, 3504, 10.3892/or.2016.5166 Luo, 2011, Anticancer effects of imperatorin isolated from Angelica dahurica: induction of apoptosis in HepG2 cells through both death-receptor- and mitochondria-mediated pathways, Chemotherapy, 57, 449, 10.1159/000331641 Mattarei, 2018, Novel mitochondria-targeted furocoumarin derivatives as possible anti-cancer agents, Front. Oncol., 8, 122, 10.3389/fonc.2018.00122 McKenna, 1997, PUVA, Psoralens and skin Cancer, 416 Melough, 2017, Identification and uantitation of furocoumarins in popularly consumed foods in the u.s. using QuEChERS extraction coupled with UPLC-MS/MS analysis, J. Agric. Food Chem., 65, 5049, 10.1021/acs.jafc.7b01279 Melough, 2017, Furocoumarin kinetics in plasma and urine of healthy adults following consumption of grapefruit (Citrus paradisi Macf.) and grapefruit juice, J. Agric. Food Chem., 65, 3006, 10.1021/acs.jafc.7b00317 Melough, 2018, Dietary furanocoumarins and skin cancer: a review of current biological evidence, Food Chem. Toxicol., 122, 163, 10.1016/j.fct.2018.10.027 Melough, 2018, Furocoumarins: a review of biochemical activities, dietary sources and intake, and potential health risks, Food Chem. Toxicol., 113, 99, 10.1016/j.fct.2018.01.030 Messer, 2011, Major furanocoumarins in grapefruit juice I: levels and urinary metabolite(s), Food Chem. Toxicol., 49, 3224, 10.1016/j.fct.2011.09.005 Munakata, 2016, Molecular evolution of parsnip (Pastinaca sativa) membrane-bound prenyltransferases for linear and/or angular furanocoumarin biosynthesis, New Phytol., 211, 332, 10.1111/nph.13899 Murray, 1982 Nam, 2005, A case of acute cholestatic hepatitis associated with the seeds of Psoralea corylifolia (Boh-Gol-Zhee), Clin. Toxicol., 43, 5890, 10.1081/CLT-200068863 Nijsten, 2003, The increased risk of skin cancer is persistent after discontinuation of psoralen+ultraviolet a: a cohort study, J Invest Dermatol, 121, 252, 10.1046/j.1523-1747.2003.12350.x Oldham, 2016, X-ray psoralen activated cancer therapy (X-PACT), PLoS One, 11, 10.1371/journal.pone.0162078 Oliveira, 2006, Psoralen analogues: synthesis, inhibitory activity of growth of human tumor cell lines and computational studies, Eur. J. Med. Chem., 41, 367, 10.1016/j.ejmech.2005.10.016 Oliveira, 2007, Synthesis and antitumour evaluation of benzopsoralen analogues, Chem. Biodivers., 4, 980, 10.1002/cbdv.200790089 Panno, 2014, Effects of psoralens as anti-tumoral agents in breast cancer cells, World J Clin Oncol, 5, 348, 10.5306/wjco.v5.i3.348 Parrish, 1974, Photochemotherapy of psoriasis with oral methoxsalen and long-wave ultraviolet light, N. Engl. J. Med., 1291, 1207, 10.1056/NEJM197412052912301 Pathak, 1974, Photobiology and photochemistry of furocoumarins (psoralens), 335 Rahman, 2015, Growth inhibition of various human cancer cell lines by imperatorin and limonin from Poncirus trifoliata rafin, Seeds. Anticancer Agents Med Chem, 5, 236, 10.2174/1871520614666140922122358 Rahman, 2012, Angelicin induces apoptosis through intrinsic caspase-dependent pathway in human SH-SY5Y neuroblastoma cells, Mol. Cell. Biochem., 369, 95, 10.1007/s11010-012-1372-1 Sayre, 2008, The increase in melanoma: are dietary furocoumarin responsible?, Med. Hypotheses, 70, 855, 10.1016/j.mehy.2007.07.029 Schmitt, 1995, Psoralen-protein photochemistry - a forgotten field, J. Photochem. Photobiol. B, 27, 101, 10.1016/1011-1344(94)07101-S Selim, 2017, Synthesis and antiproliferative activity of new furocoumarin derivatives, Chem. Heterocycl. Compd., 53, 867, 10.1007/s10593-017-2139-0 Song, 2017, Evaluation of antifungal activities and structure-activity relationships of coumarin derivatives, Pest Manag. Sci., 73, 94, 10.1002/ps.4422 Song, 2019, The mechanism of psoralen and isopsoralen hepatotoxicity as revealed by hepatic gene expression profiling in SD rats, Basic Clin Pharmacol Toxicol, 125, 527, 10.1111/bcpt.13287 Stern, 2012, The risk of squamous cell and basal cell cancer associated with psoralen and ultraviolet a therapy: a 30-year prospective study. PUVA Follow-Up Study, J Am Acad Dermatol, 66, 553, 10.1016/j.jaad.2011.04.004 Stern, 1997, Malignant melanoma in patients treated for psoriasis with methoxsalen (psoralen) and ultraviolet a radiation (PUVA), New England J Med, 336, 1041, 10.1056/NEJM199704103361501 Stern, 2001, The risk of melanoma in association with long-term exposure to PUVA, J. Am. Acad. Dermatol., 44, 755, 10.1067/mjd.2001.114576 Sumiyoshi, 2014, Anti-tumor effects of various furocoumarins isolated from the roots, seeds and fruits of Angelica and Cnidium species under ultraviolet a irradiation, I Nat Med, 68, 83, 10.1007/s11418-013-0774-z Szewczyk, 2012, Analytical methods for isolation, separation and Identification of selected furanocoumarins in plant material, 57 Teschke, 2015, Herbal hepatotoxicity in traditional and modern medicine: actual key issues and new encouraging steps, Front Pharmacol, 10.3389/fphar.2015.00072 Thornes, 1982, Cimetidine and coumarin therapy of melanoma, Lancet, 2, 328, 10.1016/S0140-6736(82)90295-1 Tong, 2017, Isoimperatorin induces apoptosis of the SGC-7901 human gastric cancer cell line via the mitochondria-mediated pathway, Oncol. Lett., 13, 518, 10.3892/ol.2016.5387 Traven, 2004, New synthetic routes to furanocoumarins and their analogs: a review, Molecules, 9, 50, 10.3390/90300050 Van Aelst, 2016, Psoralen and ultraviolet a light treatment directly affects phosphatidylinositol 3-kinase signal transduction by altering plasma membrane packing, J. Biol. Chem., 291, 24364, 10.1074/jbc.M116.735126 Velasco-Velázquez, 2003, 4-Hydroxycoumarin disorganizes the actin cytoskeleton in B16-F10 melanoma cells but not in B82 fibroblasts, decreasing their adhesion to extracellular matrix proteins and motility, Cancer Lett., 198, 179, 10.1016/S0304-3835(03)00333-1 Venugopala, 2013, Review on natural coumarin lead compounds for their pharmacological activity, BioMed Res Int, 963248 Via, 1999, New tetracyclic analogues of photochemotherapeutic drugs 5-MOP and 8-MOP: synthesis, DNA interaction, and antiproliferative activity, J. Med. Chem., 42, 4405, 10.1021/jm9910829 Via, 2009, A new psoralen derivative with enlarged antiproliferative properties, Med Chem Lett, 19, 2874, 10.1016/j.bmcl.2009.03.073 Viola, 2009, Differentiation and apoptosis in UVA-irradiated cells treated with furocoumarin derivatives, Ann. N. Y. Acad. Sci., 1171, 334, 10.1111/j.1749-6632.2009.04894.x Viola, 2007, Induction of apoptosis in Jurkat cells by photoexcited psoralen derivatives: implication of mitochondrial dysfunctions and caspases activation, Toxicol. in Vitro, 21, 211, 10.1016/j.tiv.2006.09.016 Wang, 2015, Antiproliferative and apoptotic effects of angelicin in highly invasive prostate cancer cells, Trop. J. Pharm. Res., 14, 1405, 10.4314/tjpr.v14i8.12 Wang, 2012, Furanocoumarins affect hepatic cytochrome P450 and renal organic ion transporters in mice, Toxicol. Lett., 209, 67, 10.1016/j.toxlet.2011.11.030 Wang, 2016, Effects of psoralen as an anti-tumor agent in human breast cancer MCF-7/ADR cells, Biol. Pharm. Bull., 39, 815, 10.1248/bpb.b15-00957 Wang, 2016, Exosomes play an important role in the process of psoralen reverse multidrug resistance of breast cancer, J. Exp. Clin. Cancer Res., 35, 10.1186/s13046-016-0468-y Wang, 2011, Screening antitumor compounds psoralen and isopsoralen from Psoralea corylifolia L. seeds, Evid. Based Complement. Alternat. Med., 10.1093/ecam/nen087 Widelski, 2017, Rare coumarins induce apoptosis, G1 cell block and reduce RNA content in HL60 cells, Open Chem, 15, 1, 10.1515/chem-2017-0001 Wu, 2015, Citrus consumption and risk of basal cell carcinoma and squamous cell carcinoma of the skin, Carcinogenesis, 36, 1162, 10.1093/carcin/bgv109 Wu, 2015, Citrus consumption and risk of cutaneous malignant melanoma, J. Clin. Oncol., 33, 2500, 10.1200/JCO.2014.57.4111 Xia, 2014, Photo-activated psoralen binds the ErbB2 catalytic kinase domain, blocking ErbB2 signaling and triggering tumor cell apoptosis, PLoS One, 9, 10.1371/journal.pone.0088983 Xu, 2015, The study on biological and pharmacological activity of coumarins, AP3ER, 2015, 135 Yang, 2015, 8-Methoxypsoralen induces intrinsic apoptosis in HepG2 cells: involvement of reactive oxygen species generation and ERK1/2 pathway inhibition, Cell. Physiol. Biochem., 37, 361, 10.1159/000430360 Yang, 2002 Zhang, 2018, A study of NMR-based hepatic and serum metabolomics in a liver injury Spraque-Dawley rat model induced by psoralen, Chem. Res. Toxicol., 31, 852, 10.1021/acs.chemrestox.8b00082