The influence of sesquiterpenes from Myrica rubra on the antiproliferative and pro-oxidative effects of doxorubicin and its accumulation in cancer cells

Molecules

Volumn 20, Issue 8, 2015, Pages 15343-15358

  Ambrož, Martin ^a   Boušová, Iva ^a   Skarka, Adam ^a   Hanušová, Veronika ^b   Králová, Věra ^b   Matoušková, Petra ^a   Szotáková, Barbora ^a   Skálová, Lenka ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Antiproliferative effect; Cytotoxicity; Drugs combinations; Myrica rubra; Terpenes

Indexed keywords

ANTINEOPLASTIC AGENT; DOXORUBICIN; SESQUITERPENE;

ANIMAL; CACO 2 CELL LINE; CHEMISTRY; DRUG EFFECTS; HUMAN; LIVER CELL; MYRICA; OXIDATION REDUCTION REACTION; PRIMARY CELL CULTURE; RAT; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CACO-2 CELLS; CELL LINE, TUMOR; DOXORUBICIN; HEPATOCYTES; HUMANS; MYRICA; OXIDATION-REDUCTION; PRIMARY CELL CULTURE; RATS; SESQUITERPENES;

EID: 84941248208     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules200815343     Document Type: Article

References (41)

1. Merfort, I. Perspectives on Sesquiterpene Lactones in Inflammation and Cancer. Curr. Drug Targets 2011, 12, 1560-1573.
2. Salminen, A.; Lehtonen, M.; Suuronen, T.; Kaarniranta, K.; Huuskonen, J. Terpenoids: Natural inhibitors of NF-kappa B signaling with anti-inflammatory and anticancer potential. Cell. Mol. Life Sci. 2008, 65, 2979-2999.
3. Bartikova, H.; Hanusova, V.; Skalova, L.; Ambroz, M.; Bousova, I. Antioxidant, Pro-Oxidant and Other Biological Activities of Sesquiterpenes. Curr. Top. Med. Chem. 2014, 14, 2478-2494.
4. Pajak, B.; Orzechowski, A.; Gajkowska, B. Molecular basis of parthenolide-dependent proapoptotic activity in cancer cells. Folia Histochem. Cytobiol. 2008, 46, 129-135.
5. Bhalla, Y.; Gupta, V.K.; Jaitak, V. Anticancer activity of essential oils: A review. J. Sci. Food Agric. 2013, 93, 3643-3653.
6. Huang, M.; Lu, J.J.; Huang, M.Q.; Bao, J.L.; Chen, X.P.; Wang, Y.T. Terpenoids: Natural products for cancer therapy. Expert Opin. Investig. Drugs 2012, 21, 1801-1818.
7. Legault, J.; Pichette, A. Potentiating effect of β-caryophyllene on anticancer activity of α-humulene, isocaryophyllene and paclitaxel. J. Pharm. Pharmacol. 2007, 59, 1643-1647.
8. Kim, C.; Cho, S.K.; Kim, K.D.; Nam, D.; Chung, W.S.; Jang, H.J.; Lee, S.G.; Shim, B.S.; Sethi, G.; Ahn, K.S. β-Caryophyllene oxide potentiates TNF α-induced apoptosis and inhibits invasion through down-modulation of NF-kappa B-regulated gene products. Apoptosis 2014, 19, 708-718.
9. Abdul, A.B.; Abdelwahab, S.I.; Jalinas, J.B.; Al-Zubairi, A.S.; Taha, M.M.E. Combination of Zerumbone and Cisplatin to Treat Cervical Intraepithelial Neoplasia in Female BALB/c Mice. Int. J. Gynecol. Cancer 2009, 19, 1004-1010.
10. Xu, W.S.; Dang, Y.Y.; Chen, X.P.; Lu, J.J.; Wang, Y.T. Furanodiene Presents Synergistic Anti-proliferative Activity With Paclitaxel via Altering Cell Cycle and Integrin Signaling in 95-D Lung Cancer Cells. Phytother. Res. 2014, 28, 296-299.
11. Zhong, Z.F.; Li, Y.B.; Wang, S.P.; Tan, W.; Chen, X.P.; Chen, M.W.; Wang, Y.T. Furanodiene enhances tamoxifen-induced growth inhibitory activity of ERa-positive breast cancer cells in a PPAR gamma independent manner. J. Cell. Biochem. 2012, 113, 2643-2651.
12. Adorjan, B.; Buchbauer, G. Biological properties of essential oils: An updated review. Flavour Fragr. J. 2010, 25, 407-426.
13. Bansal, A.; Moriarity, D.M.; Takaku, S.; Setzer, W.N. Chemical composition and cytotoxic activity of the leaf essential oil of Ocotea tonduzii from Monteverde, Costa Rica. Nat. Prod. Commun. 2007, 2, 781-784.
14. Erdogan, A.; Ozkan, A. Effects of Thymus revolutus Celak essential oil and its two major components on Hep G2 cells membrane. Biologia 2013, 68, 105-111.
15. Raut, J.S.; Karuppayil, S.M. A status review on the medicinal properties of essential oils. Ind. Crops Prod. 2014, 62, 250-264.
16. Langhansova, L.; Hanusova, V.; Rezek, J.; Stohanslova, B.; Ambroz, M.; Kralova, V.; Vanek, T.; Lou, J.D.; Yun, Z.L.; Yang, J.; et al. Essential oil from Myrica rubra leaves inhibits cancer cell proliferation and induces apoptosis in several human intestinal lines. Ind. Crops Prod. 2014, 59, 20-26.
17. Kang, W.; Li, Y.; Xu, Y.; Jiang, W.; Tao, Y. Characterization of Aroma Compounds in Chinese Bayberry (Myrica rubra Sieb. et Zucc.) by Gas Chromatography Mass Spectrometry (GC-MS) and Olfactometry (GC-O). J. Food Sci. 2012, 77, C1030-C1035.
18. Hanusova, V.; Bousova, I.; Skalova, L. Possibilities to increase the effectiveness of doxorubicin in cancer cells killing. Drug Metab. Rev. 2011, 43, 540-557.
19. Sun, C.D.; Huang, H.Z.; Xu, C.J.; Li, X.; Chen, K.S. Biological Activities of Extracts from Chinese Bayberry (Myrica rubra Sieb. et Zucc.): A Review. Plant Foods Hum. Nutr. 2013, 68, 97-106.
20. El Hadri, A.; del Rio, M.A.G.; Sanz, J.; Coloma, A.G.; Idaomar, M.; Ozonas, B.R.; Gonzalez, J.B.; Reus, M.I.S. Cytotoxic activity of α-humulene and trans-caryophyllene from Salvia officinalis in animal and human tumor cells. Anal. Real Acad. Nac. Farm. 2010, 76, 343-356.
21. Legault, J.; Dahl, W.; Debiton, E.; Pichette, A.; Madelmont, J.C. Antitumor activity of balsam fir oil: Production of reactive oxygen species induced by α-humulene as possible mechanism of action. Planta Med. 2003, 69, 402-407.
22. Sylvestre, M.; Pichette, A.; Lavoie, S.; Longtin, A.; Legault, J. Composition and cytotoxic activity of the leaf essential oil of Comptonia peregrina (L.) Coulter. Phytother. Res. 2007, 21, 536-540.
23. Liu, K.; Chen, Q.; Liu, Y.; Zhou, X.; Wang, X. Isolation and Biological Activities of Decanal, Linalool, Valencene, and Octanal from Sweet Orange Oil. J. Food Sci. 2012, 77, C1156-C1161.
24. Jun, N.J.; Mosaddik, A.; Moon, J.Y.; Jang, K.C.; Lee, D.S.; Ahn, K.S.; Cho, S.K. Cytotoxic Activity of β-Caryophyllene Oxide Isolated from Jeju Guava (Psidium cattleianum Sabine) Leaf. Rec. Natl. Prod. 2011, 5, 242-246.
25. Park, K.R.; Nam, D.; Yun, H.M.; Lee, S.G.; Jang, H.J.; Sethi, G.; Cho, S.K.; Ahn, K.S. β-Caryophyllene oxide inhibits growth and induces apoptosis through the suppression of PI3K/AKT/mTOR/S6K1 pathways and ROS-mediated MAPKs activation. Cancer Lett. 2011, 312, 178-188.
26. Di Sotto, A.; Maffei, F.; Hrelia, P.; Castelli, F.; Sarpietro, M.G.; Mazzanti, G. Genotoxicity assessment of β-caryophyllene oxide. Regul. Toxicol. Pharmacol. 2013, 66, 264-268.
27. Chang, H.J.; Kim, H.J.; Chun, H.S. Quantitative structure-activity relationship (QSAR) for neuroprotective activity of terpenoids. Life Sci. 2007, 80, 835-841.
28. Krishnaiah, Y.S.R.; Al-Saidan, S.M.; Jayaram, B. Effect of nerodilol, carvone and anethole on the in vitro transdermal delivery of selegiline hydrochloride. Pharmazie 2006, 61, 46-53.
29. Saeedi, M.; Morteza-Semnani, K. Penetration-Enhancing Effect of the Essential Oil and Methanolic Extract of Eryngium bungei on Percutaneous Absorption of Piroxicam through Rat Skin. J. Essent. Oil Bear. Plants 2009, 12, 728-741.
30. Williams, A.C.; Barry, B.W. Penetration enhancers. Adv. Drug Deliv. Rev. 2012, 64, 128-137.
31. Chou, T.C. Drug Combination Studies and Their Synergy Quantification Using the Chou-Talalay Method. Cancer Res. 2010, 70, 440-446.
32. Mahmoud, S.S.; Torchilin, V.P. Hormetic/Cytotoxic Effects of Nigella sativa Seed Alcoholic and Aqueous Extracts on MCF-7 Breast Cancer Cells Alone or in Combination with Doxorubicin. Cell Biochem. Biophys. 2013, 66, 451-460.
33. Riganti, C.; Doublier, S.; Costamagna, C.; Aldieri, E.; Pescarmona, G.; Ghigo, D.; Bosia, A. Activation of nuclear factor-kappa B pathway by Simvastatin and RhoA silencing increases doxorubicin cytotoxicity in human colon cancer HT29 cells. Mol. Pharmacol. 2008, 74, 476-484.
34. Wozniak, M.; Szulawska-Mroczek, A.; Hartman, M.L.; Nejc, D.; Czyz, M. Parthenolide Complements the Cell Death-inducing Activity of Doxorubicin in Melanoma Cells. Anticancer Res. 2013, 33, 3205-3212.
35. Martin-Cordero, C.; Leon-Gonzalez, A.J.; Calderon-Montano, J.M.; Burgos-Moron, E.; Lopez-Lazaro, M. Pro-Oxidant Natural Products as Anticancer Agents. Curr. Drug Targets 2012, 13, 1006-1028.
36. Trachootham, D.; Alexandre, J.; Huang, P. Targeting cancer cells by ROS-mediated mechanisms: A radical therapeutic approach? Nat. Rev. Drug Discov. 2009, 8, 579-591.
37. Li, X.; Fang, P.; Mai, J.; Choi, E.T.; Wang, H.; Yang, X.F. Targeting mitochondrial reactive oxygen species as novel therapy for inflammatory diseases and cancers. J. Hematol. Oncol. 2013, 6, 19, doi:10.1186/1756-8722-6-19.
38. Pacifico, S.; D'Abrosca, B.; Golino, A.; Mastellone, C.; Piccolella, S.; Fiorentino, A.; Monaco, P. Antioxidant evaluation of polyhydroxylated nerolidols from redroot pigweed (Amaranthus retroflexus) leaves. Lwt-Food Sci. Technol. 2008, 41, 1665-1671.
39. Vinholes, J.; Goncalves, P.; Martel, F.; Coimbra, M.A.; Rocha, S.M. Assessment of the antioxidant and antiproliferative effects of sesquiterpenic compounds in in vitro CaCo-2 cell models. Food Chem. 2014, 156, 204-211.
40. Wang, H.; Joseph, J.A. Quantifying cellular oxidative stress by dichlorofluorescein assay using microplate reader. Free Radic. Biol. Med. 1999, 27, 612-616.
41. Skarka, A.; Skarydova, L.; Stambergova, H.; Wsol, V. Anthracyclines and their metabolism in human liver microsomes and the participation of the new microsomal carbonyl reductase. Chem. Biol. Interact. 2011, 191, 66-74.