Evaluation of antitumoral and apoptotic potentials of masticadienonic acid and tirucallol from Pistacia vera L. stems

References

• Ahmad N, Keehn CA, Coppola D. 2004. The expression of insulin-like growth factor-I receptor correlates with Fuhrman grading of renal cell carcinomas. Hum Pathol. 35(9):1132–1136. doi: 10.1016/j.humpath.2004.05.012.
   PubMed Web of Science ®Google Scholar
• Assimopoulou AN, Papageorgiou VP. 2005. GC-MS analysis of penta- and tetracyclic triterpenes from resins of Pistacia species. Part I. Pistacia lentiscus var. Chia. Biomed Chromatogr. 19(4):285–311. doi: 10.1002/bmc.454.
   PubMed Web of Science ®Google Scholar
• Balan KV, Prince J, Han Z, Dimas K, Cladaras M, Wyche JH, Sitaras NM, Pantazis P. 2007. Antiproliferative activity and induction of apoptosis in human colon cancer cells treated in vitro with constituents of a product derived from Pistacia lentiscus L. var. Chia. Phytomedicine. 14(4):263–272. doi: 10.1016/j.phymed.2006.03.009.
   PubMed Web of Science ®Google Scholar
• Bozorgi M, Memariani Z, Mobli M, Salehi Surmaghi MH, Shams-Ardekani MR, Rahimi R. 2013. Five Pistacia species (P. vera, P. atlantica, P. terebinthus, P. khinjuk, and P. lentiscus): a review of their traditional uses, phytochemistry, and pharmacology. ScientificWorldJournal. 2013:219815–219833. doi: 10.1155/2013/219815.
   PubMedGoogle Scholar
• Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB. 1987. Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 47(4):936–942. PMID: 3802100.
   PubMed Web of Science ®Google Scholar
• Chamani J, Moosavi-Movahedi AA, Hakimelahi GH. 2005. Structural changes in β-lactoglobulin by conjugation with three different kinds of carboxymethyl cyclodextrins. Thermochim Acta. 432(1):106–111. doi: 10.1016/j.tca.2005.04.014.
   Web of Science ®Google Scholar
• Chávez IO, Apan TR, Martínez-Vázquez M. 2005. Cytotoxic activity and effect on nitric oxide production of tirucallane-type triterpenes. J Pharm Pharmacol. 57(9):1087–1091. doi: 10.1211/jpp.57.9.0003.
   PubMed Web of Science ®Google Scholar
• Chen H, Khemtong C, Yang X, Chang X, Gao J. 2011. Nanonization strategies for poorly water-soluble drugs. Drug Discov Today. 16(7–8):354–360. doi: https://doi.org/10.1016/J.DRUDIS.2010.02.009.
   PubMed Web of Science ®Google Scholar
• Chinnaiyan AM, Dixit VM. 1996. The cell-death machine. Curr Biol. 6(5):555–562. doi: https://doi.org/10.1016/s0960-9822(02)00541-9.
   PubMed Web of Science ®Google Scholar
• Cragg GM, Newman DJ. 2005. Plants as a source of anti-cancer agents. J Ethnopharmacol. 100(1–2):72–79. doi: 10.1016/j.jep.2005.05.011.
   PubMed Web of Science ®Google Scholar
• de Souza LS, Puziol LC, Tosta CL, Bittencourt MLF, Ardisson JS, Kitagawa RR, Filgueiras PR, Kuster RM. 2019. Analytical methods to access the chemical composition of an Euphorbia tirucalli anticancer latex from traditional Brazilian medicine. J Ethnopharmacol. 237:255–265. doi: 10.1016/j.jep.2019.03.041.
   PubMed Web of Science ®Google Scholar
• Dreher ML. 2012. Pistachio nuts: composition and potential health benefits. Nutr Rev. 70(4):234–240. doi: 10.1111/j.1753-4887.2011.00467.x.
   PubMed Web of Science ®Google Scholar
• George MA, Lustberg MB, Orchard TS. 2020. Psychoneurological symptom cluster in breast cancer: the role of inflammation and diet. Breast Cancer Res Treat. 184(1):1–9. doi: 10.1007/s10549-020-05808-x.
   PubMed Web of Science ®Google Scholar
• Göbel A, Dell’Endice S, Jaschke N, Pählig S, Shahid A, Hofbauer LC, Rachner TD. 2021. The role of inflammation in breast and prostate cancer metastasis to bone. Int J Mol Sci. 22(10):5078. doi: 10.3390/ijms22105078.
   PubMed Web of Science ®Google Scholar
• He ML, Li A, Xu CS, Wang SL, Zhang MJ, Gu H, Yang YQ, Tao HH. 2007. Mechanism of antiprostate cancer by gum mastic: NF kappa B signal as target. Acta Pharmacol Sin. 28(3):446–452. doi: 10.1111/j.1745-7254.2007.00536.x.
   PubMed Web of Science ®Google Scholar
• Hosseinzadeh M, Nikjoo S, Zare N, Delavar D, Beigoli S, Chamani J. 2019. Characterization of the structural changes of human serum albumin upon interaction with singlewalled and multiwalled carbon nanotubes: spectroscopic and molecular modeling approaches. Res Chem Intermed. 45(2):401–423. doi: 10.1007/s11164-018-3608-5.
   Web of Science ®Google Scholar
• Janicke RU, Sprengart ML, Wati MR, Porter AG. 1998. Caspase-3 is required for DNA fragmentation and morphological changes associated with apoptosis. J Biol Chem. 273(16):9357–9360. doi: 10.1074/jbc.273.16.9357.
   PubMed Web of Science ®Google Scholar
• Jiang L, Li L, He X, Yi Q, He B, Cao J, Pan W, Gu Z. 2015. Overcoming drug-resistant lung cancer by paclitaxel loaded dual-functional liposomes with mitochondria targeting and pH-response. Biomaterials. 52:126–139. doi: 10.1016/j.biomaterials.2015.02.004.
   PubMed Web of Science ®Google Scholar
• Karagoz ID, Cakir A, Ozaslan M, Halil Kili I, Tepe B, Akdogan E, Kazaz C. 2022. Anticancer agents from Xanthium strumarium fruits against C6 glioma cells. Int J Pharmacol. 18(3):437–454. doi: 10.3923/ijp.2022.437.454.
   Google Scholar
• Kawabata Y, Wada K, Nakatani M, Yamada S, Onoue S. 2011. Formulation design for poorly water-soluble drugs based on biopharmaceutics classification system: basic approaches and practical applications. Int J Pharm. 420(1):1–10. doi: 10.1016/J.IJPHARM.2011.08.032.
   PubMed Web of Science ®Google Scholar
• Khashkhashi-Moghadam S, Ezazi-Toroghi S, Kamkar-Vatanparast M, Jouyaeian P, Mokaberi P, Yazdyani H, Amiri-Tehranizadeh Z, Saberi MR, Chamani J. 2022. Novel perspective into the interaction behavior study of the cyanidin with human serum albumin-holo transferrin complex: spectroscopic, calorimetric and molecular modeling approaches. J Mol Liq. 356:119042. doi: 10.1016/j.molliq.2022.119042.
   Web of Science ®Google Scholar
• Li F, Srinivasan A, Wang Y, Armstrong RC, Tomaselli KJ, Fritz LC. 1997. Cell-specific induction of apoptosis by microinjection of cytochrome c. Bcl-xL has activity independent of cytochrome c release. J Biol Chem. 272(48):30299–30305. doi: 10.1074/jbc.272.48.30299.
   PubMed Web of Science ®Google Scholar
• Li G, Xu Q, Han K, Yan W, Huang C. 2020. Experimental evidence and network pharmacology-based analysis reveal the molecular mechanism of Tongxinluo capsule administered in coronary heart diseases. Biosci Rep. 40(10). doi: 10.1042/BSR20201349.
   Google Scholar
• Loizou S, Paraschos S, Mitakou S, Chrousos GP, Lekakis I, Moutsatsou P. 2009. Chios mastic gum extract and isolated phytosterol tirucallol exhibit anti-inflammatory activity in human aortic endothelial cells. Exp Biol Med. 234(5):553–561. doi: 10.3181/0811-RM-338.
   PubMed Web of Science ®Google Scholar
• Lopes CM, Dourado A, Oliveira R. 2017. Phytotherapy and nutritional supplements on breast cancer. Biomed Res Int. 2017:7207983. doi: 10.1155/2017/7207983.
   PubMed Web of Science ®Google Scholar
• Loutrari H, Magkouta S, Pyriochou A, Koika V, Kolisis FN, Papapetropoulos A, Roussos C. 2006. Mastic oil from Pistacia lentiscus var. Chia inhibits growth and survival of human K562 leukemia cells and attenuates angiogenesis. Nutr Cancer. 55(1):86–93. doi: 10.1207/s15327914nc5501_11.
   PubMed Web of Science ®Google Scholar
• Maamri S, Benarous K, Yousfi M. 2021. Identification of 3-methoxycarpachromene and masticadienonic acid as new target inhibitors against trypanothione reductase from Leishmania infantum using molecular docking and ADMET prediction. Molecules. 26(11):3335. doi: 10.3390/molecules26113335.
   PubMed Web of Science ®Google Scholar
• Majtnerová P, Roušar T. 2018. An overview of apoptosis assays detecting DNA fragmentation. Mol Biol Rep. 45(5):1469–1478. doi: 10.1007/s11033-018-4258-9.
   PubMed Web of Science ®Google Scholar
• Malek-Esfandiari Z, Rezvani-Noghani A, Sohrabi T, Mokaberi P, Amiri-Tehranizadeh Z, Chamani J. 2023. Molecular dynamics and multi-spectroscopic of the interaction behavior between bladder cancer cells and calf thymus DNA with Rebeccamycin: apoptosis through the down regulation of PI3K/AKT signalling pathway. J Fluoresc. 33(4):1537–1557. doi: 10.1007/s10895-023-03169-4.
   PubMed Web of Science ®Google Scholar
• Merisko-Liversidge E, Liversidge GG, Cooper ER. 2003. Nanosizing: a formulation approach for poorly water-soluble compounds. Eur J Pharm Sci. 18(2):113–120. doi: 10.1016/s0928-0987(02)00251-8.
   PubMed Web of Science ®Google Scholar
• Momenimovahed Z, Salehiniya H. 2019. Epidemiological characteristics of and risk factors for breast cancer in the world. Breast Cancer. 11:151–164. doi: 10.2147/BCTT.S176070.
   PubMed Web of Science ®Google Scholar
• Nagata S. 1997. Apoptosis by death factor. Cell. 88(3):355–365. doi: 10.1016/s0092-8674(00)81874-7.
   PubMed Web of Science ®Google Scholar
• Nicholson DW. 1999. Caspase structure, proteolytic substrates, and function during apoptotic cell death. Cell Death Differ. 6(11):1028–1042. doi: 10.1038/sj.cdd.4400598.
   PubMed Web of Science ®Google Scholar
• Piñón-Zárate G, Reyes-Riquelme F, Sánchez-Monroy MB, Velasco-Torrez M, Martínez-Vázquez M, Cárdenas-Monroy CA, Hernandez-Téllez B, Jarquín-Yáñez K, Herrera-Enríquez MA, Castell-Rodríguez AE. 2022. Immunomodulatory properties of masticadienonic acid and 3α-hydroxy masticadienoic acid in dendritic cells. Molecules. 27(4):1451. doi: 10.3390/molecules27041451.
   PubMed Web of Science ®Google Scholar
• Ramírez-León A, Barajas-Martinez H, Flores-Torales E, Orozco-Barocio A. 2012. Immunostimulating effect of aqueous extract of Amphypterygium adstringens on immune cellular response in immunosuppressed mice. Afr J Tradit Complement Altern Med. 10:35–39. doi: 10.4314/ajtcam.v10i1.6.
   PubMedGoogle Scholar
• Roos WP, Kaina B. 2006. DNA damage-induced cell death by apoptosis. Trends Mol Med. 12(9):440–450. doi: 10.1016/j.molmed.2006.07.007.
   PubMed Web of Science ®Google Scholar
• Roos WP, Kaina B. 2012. DNA damage-induced apoptosis: from specific DNA lesions to the DNA damage response and apoptosis. Cancer Lett. 8. doi: 10.1016/j.canlet.2012.01.007.
   Google Scholar
• Sakagami H, Kishino K, Kobayashi M, Hashimoto K, Iida S, Shimetani A, Nakamura Y, Takahashi K, Ikarashi T, Fukamachi H, et al. 2009. Selective antibacterial and apoptosis-modulating activities of mastic. In Vivo. 23(2):215–223. PMID: 19414406.
   PubMed Web of Science ®Google Scholar
• Sánchez-Monroy M, Jacobo-Herrera NJ, Zentella-Dehesa A, Hernández-Téllez B, Martínez-Vázquez M. 2017. Masticadienonic and 3α-OH masticadienoic acids induce apoptosis and inhibit cell proliferation and tumor growth in prostate cancer xenografts in vivo. Molecules. 22(9):1479. doi: 10.3390/molecules22091479.
   PubMed Web of Science ®Google Scholar
• Scaffidi C, Fulda S, Srinivasan A, Friesen C, Li F, Tomaselli KJ, Debatin KM, Krammer PH, Peter ME. 1998. Two CD95 (APO-1/Fas) signalling pathways. Embo J. 17(6):1675–1687. doi: 10.1093/emboj/17.6.1675.
   PubMed Web of Science ®Google Scholar
• Seifaddinipour M, Farghadani R, Namvar F, Bin Mohamad J, Muhamad NA. 2020. In vitro and in vivo anticancer activity of the most cytotoxic fraction of pistachio hull extract in breast cancer. Molecules. 25(8):1776. doi: 10.3390/molecules25081776.
   PubMed Web of Science ®Google Scholar
• Seifzadeh N, Sahari MA, Barzegar M, Gavlighi HA, Calani L, Del Rio D, Galaverna G. 2019. Evaluation of polyphenolic compounds in membrane concentrated pistachio hull extract. Food Chem. 277:398–406. doi: 10.1016/j.foodchem.2018.10.001.
   PubMed Web of Science ®Google Scholar
• Sharifi-Rad A, Mehrzad J, Darroudi M, Saberi MR, Chamani J. 2021. Oil-in-water nanoemulsions comprising Berberine in olive oil: biological activities, binding mechanisms to human serum albumin or holo-transferrin and QMMD simulations. J Biomol Struct Dyn. 39(3):1029–1043. doi: 10.1080/07391102.2020.1724568.
   PubMed Web of Science ®Google Scholar
• Siegel RL, Miller KD, Jemal A. 2020. Cancer statistics, 2020. CA Cancer J Clin. 70(1):7–30. doi: 10.3322/caac.21590.
   PubMed Web of Science ®Google Scholar
• Siegel RL, Miller KD, Fuchs HE, Jemal A. 2021. Cancer statistics, 2021. CA Cancer J Clin. 71(1):7–33. doi: 10.3322/caac.21654.
   PubMed Web of Science ®Google Scholar
• Sonmezdag AS, Kelebek H, Selli S. 2019a. Effect of hulling methods and roasting treatment on phenolic compounds and physicochemical properties of cultivars ‘Ohadi’ and ‘Uzun’ pistachios (Pistacia vera L.). Food Chem. 272:418–426. doi: 10.1016/j.foodchem.2018.08.065.
   PubMed Web of Science ®Google Scholar
• Sonmezdag AS, Kelebek H, Selli S. 2019b. Elucidation of hulling-induced changes in the aroma and aroma-active compounds of cv. Uzun pistachio (Pistacia vera L.). J Sci Food Agric. 99(10):4702–4711. doi: 10.1002/jsfa.9711.
   PubMed Web of Science ®Google Scholar
• Subramani R, Lakshmanaswamy R. 2017. Complementary and alternative medicine and breast cancer. Prog Mol Biol Transl Sci. 151:231–274. doi: 10.1016/bs.pmbts.2017.07.008.
   PubMed Web of Science ®Google Scholar
• Sun XM, MacFarlane M, Zhuang J, Wolf BB, Green DR, Cohen GM. 1999. Distinct caspase cascades are initiated in receptor-mediated and chemical-induced apoptosis. J Biol Chem. 274(8):5053–5060. doi: 10.1074/jbc.274.8.5053.
   PubMed Web of Science ®Google Scholar
• Sung H, Ferlay J, Siegel RL, Laversanne M, Soerjomataram I, Jemal A, Bray F. 2021. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA Cancer J Clin. 71(3):209–249. doi: 10.3322/caac.21660.
   PubMed Web of Science ®Google Scholar
• Taheri R, Hamzkanlu N, Rezvani Y, Niroumand S, Samandar F, Amiri-Tehranizadeh Z, Saberi MR, Chamani J. 2022. Exploring the HSA/DNA/lung cancer cells binding behavior of p-Synephrine, a naturally occurring phenyl ethanol amine with anti-adipogenic activity: multi spectroscopic, molecular dynamic and cellular approaches. J Mol Liq. 368:120826. doi: 10.1016/j.molliq.2022.120826.
   Web of Science ®Google Scholar
• Tamaki T, Kamatsuka K, Sato T, Morooka S, Otsuka K, Hattori M, Sugiyama T. 2017. A novel transmembrane protein defines the endoplasmic reticulum stress-induced cell death pathway. Biochem Biophys Res Commun. 486(1):149–155. doi: 10.1016/j.bbrc.2017.03.017.
   PubMed Web of Science ®Google Scholar
• Thompson CB. 1995. Apoptosis in the pathogenesis and treatment of disease. Science. 267(5203):1456–1462. doi: 10.1126/science.7878464.
   PubMed Web of Science ®Google Scholar
• Torre LA, Siegel RL, Ward EM, Jemal A. 2016. Global cancer incidence and mortality rates and trends—an update. Cancer Epidemiol Biomarkers Prev. 25(1):16–27. doi: 10.1158/1055-9965.EPI-15-0578.
   PubMed Web of Science ®Google Scholar
• Waks AG, Winer EP. 2019. Breast cancer treatment: a review. JAMA. 321(3):288–300. doi: 10.1001/jama.2018.19323.
   PubMed Web of Science ®Google Scholar
• Wang JJ, Lei KF, Han F. 2018. Tumor microenvironment: recent advances in various cancer treatments. Eur Rev Med Pharmacol Sci. 22(12):3855–3864. doi: 10.26355/eurrev_201806_15270.
   PubMed Web of Science ®Google Scholar
• Yabo-Dambagi L, Akyuz M, Aydın T, Cakir A. 2020. Antidiabetic and anticholinesterase properties of extracts and pure metabolites of fruit stems of Pistachio (Pistacia vera L.). Current Org Chem. 24(7):785–797. doi: 10.2174/1385272824666200401111036.
   Web of Science ®Google Scholar
• Yeo SK, Guan JL. 2017. Breast cancer: multiple subtypes within a tumor? Trends Cancer. 3(11):753–760. doi: 10.1016/j.trecan.2017.09.001.
   PubMed Web of Science ®Google Scholar
• Zaidi Z, Dib HA. 2019. The worldwide female breast cancer incidence and survival, 2018. AACR Cancer Res. 79(13_Supplement):4191–4191. doi: 10.1158/1538-7445.AM2019-4191.
   Web of Science ®Google Scholar
• Zare-Feizabadi N, Amiri-Tehranizadeh Z, Sharifi-Rad A, Mokaberi P, Nosrati N, Hashemzadeh F, Rahimi HR, Saberi MR, Chamani J. 2021. Determining the interaction behavior of calf thymus DNA with anastrozole in the presence of histone H1: spectroscopies and cell viability of MCF-7 cell line investigations. DNA Cell Biol. 40(8):1039–1051. doi: 10.1089/dna.2021.0052.
   PubMed Web of Science ®Google Scholar