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The antiproliferative potential of isolated emodin and aloe-emodin from Rheum ribes on different cancer cell lines

Year 2020, Volume: 13 Issue: 2, 160 - 168, 15.08.2020

Mehmet Kadir Erdoğan Can Ali Agca İbrahim Halil Geçibesler

https://doi.org/10.46309/biodicon.2020.753046
Cited By: 4

Abstract

Herbal compounds are important resources that used in the treatment of many diseases, and are inspiring in drug design and development. Rheum ribes, a perennial native plant, has potentially diverse medicinal effects, including antioxidant, antibacterial and anti-tumor activity. The key molecules associated with anticancer activity of R. ribes in tumor formation still remains unclear. The present study was aimed to elucidate the antiproliferative effects of two purified compounds, emodin and aloe-emodin, from R. ribes. In our study, chromatographic separation was used to purification of compounds. Experimental 1D and 2D 1H and 13C-NMR spectra helped us to confirm the chemical structures of emodin and aloe-emodin. The viability of human glioblastoma cell line (U373), human breast carcinoma cells (MCF-7), and human colorectal cancer cell line (HT-29) were detected by WST-1 proliferation assay as dose- and time-dependent. The isolated emodin and aloe-emodin from R. ribes, reduced viability of human glioblastoma, breast and colorectal cancer cell lines in dose- and time-dependent manner significantly. These antiproliferative effects may contribute as a possible strategy to the development of new therapeutic approaches in the treatment of cancer.

Keywords

Rheum ribes emodin aloe-emodin cancer glioblastoma

Supporting Institution

This study was supported by The Scientific Research Projects Coordination Unit of Bingol University (Project no: BAP-FEF.2017.00.010).

Project Number

BAP-FEF.2017.00.010

References

  • [1] Saklani, A., Kutty, S. K. (2008). Plant-derived compounds in clinical trials. Drug discovery today, 13(3-4), 161-171. https://doi.org/10.1016/j.drudis.2007.10.010
  • [2] Zhou, Y., Zheng, J., Li, Y., Xu, D. P., Li, S., Chen, Y. M., Li, H. B. (2016). Natural polyphenols for prevention and treatment of cancer. Nutrients, 8(8), 515. https://doi.org/10.3390/nu8080515
  • [3] Kashiwada, Y., Nonaka, G. I., Nishioka, I., Yamagishi, T. (1988). Galloyl and hydroxycinnamoylglucoses from rhubarb. Phytochemistry, 27(5), 1473-1477. https://doi.org/10.1016/0031-9422(88)80218-8
  • [4] Öztürk, M., Aydoğmuş-Öztürk, F., Duru, M. E., Topçu, G. (2007). Antioxidant activity of stem and root extracts of Rhubarb (Rheum ribes): An edible medicinal plant. Food chemistry, 103(2), 623-630. https://doi.org/10.1016/j.foodchem.2006.09.005
  • [5] Shockravi, A., Agh Nasiri, K. (1997). Synthesis of 1, 2, 3, 4, 5, 6, 7, 8-Octahydro-9-Ethoxy-10-Hydroxy-1-Anthracenone [OEHA]. Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 16(1), 10-14.
  • [6] Cullen, J. (1966). Rheum L. In PH. Davis (Ed.). Flora of Turkey and the East Aegean Islands (Vol. 2, pp. 268–269). Edinburgh: Edinburgh University Press.
  • [7] Baytop, T. (1999). Rheum ribes L. In T. Baytop (Ed.). Therapy with medicinal plants in turkey (Vol. 1, pp. 319–320). Istanbul: Nobel Tıp Publication Press.
  • [8] Tabata, M., Sezik, E., Honda, G., Yeşilada, E., Fukui, H., Goto, K., Ikeshiro, Y. (1994). Traditional medicine in Turkey III. Folk medicine in East Anatolia, Van and Bitlis provinces. Int. J of Pharmacognosy, 32(1), 3-12. https://doi.org/10.3109/13880209409082966
  • [9] Abu-Irmaileh, B. E., Afifi, F. U. (2003). Herbal medicine in Jordan with special emphasis on commonly used herbs. Journal of Ethnopharmacology, 89(2-3), 193-197. https://doi.org/10.1016/S0378-8741(03)00283-6
  • [10] Ozbek, H., Ceylan, E., Kara, M., Ozgokce, F., Koyuncu, M. (2004). Hypoglycemic effect of Rheum ribes roots in alloxan induced diabetic and normal mice. Scandinavian Journal of Laboratory Animal Science, 31(2), 113-115.
  • [11] Bazzaz, B.S.F., Khajehkaramadin, M., Shokooheizadeh, H.R. (2005). In vitro antibacterial activity of Rheum ribes extract obtained from various plant parts against clinical ısolates of gram-negative pathogens. Iran. J. Pharm. Res, 2, 87-91.
  • [12] Bonjar, G. S. (2004). Evaluation of antibacterial properties of Iranian medicinal-plants against Micrococcus luteus, Serratia marcescens, Klebsiella pneumoniae and Bordetella bronchoseptica. Asian J. Plant Sci, 3(1), 82-86.
  • [13] Bonjar, G. S. (2004). Inhibition of three isolates of Staphylococcus aureus mediated by plants used by Iranian native people. J Med Sci, 4(2), 136-141.
  • [14] Hudson, J. B., Lee, M. K., Sener, B., Erdemoglu, N. (2000). Antiviral activities in extracts of Turkish medicinal plants. Pharmaceutical biology, 38(3), 171-175. https://doi.org/10.1076/1388-0209(200007)3831-SFT171
  • [15] Mericli, A. H., Tuzlaci, E. (1990). Constituents of Rheum ribes. Fitoterapia, 61(4).
  • [16] Tuzlacı, E., Meriçli, A. H. (1991, May). Some studies on Isgın (Rheum ribes) and its distribution in Turkey. In Proceeding of the 9th Symposium on Plant Drugs (16-19 May 1991, Eskisehir), Turkey (pp. 336-341).
  • [17] Tosun, F., Kizilay, C. A. (2003). Anthraquinones and flavonoids from Rheum ribes. J Fac Pharm Ankara, 32, 31-5.
  • [18] Erdoğan, M. K., Ağca, C. A., Aşkın, H. (2019). Enhanced antiproliferative and apoptotic effects of 5-fluorouracil by combined with Pistacia eurycarpa Extracts on human colorectal cancer cells. Biological Diversity and Conservation, 12(1), 27-38. https://doi.org/10.5505/biodicon.2019.57441
  • [19] Barros, I. B. D., Daniel, J. F. D. S., Pinto, J. P., Rezende, M. I., Braz Filho, R., Ferreira, D. T. (2011). Phytochemical and antifungal activity of anthraquinones and root and leaf extracts of Coccoloba mollis on phytopathogens. Brazilian Archives of Biology and Technology, 54(3), 535-541. https://doi.org/10.1590/S1516-89132011000300015
  • [20] Zhang, Y. Z., Lu, Y. H., Wei, D. Z., Chou, G. X., Zhu, E. Y. (2007). Preparative isolation and purification of hydroxyanthraquinones from Rheum tanguticum Maxim. on normal phase silica gel: using a Flash Master Personal system. Preparative biochemistry & biotechnology, 37(3), 185-193. https://doi.org/10.1080/10826060701386661
  • [21] Erdoğan, M. K., Geçibesler, İ. H., Behçet, L. (2020). Chemical constituents, antioxidant, antiproliferative and apoptotic effects of a new endemic Boraginaceae species: Paracaryum bingoelianum. Results in Chemistry, 2, 100032. https://doi.org/10.1016/j.rechem.2020.100032
  • [22] Li, W.Y., Chan, S.W., Guo, D.J., Chung, M.K., Leung, T.Y., Yu, P.H.F. (2009). Water extract of Rheum officinale Baill. induces apoptosis in human lung adenocarcinoma A549 and human breast cancer MCF-7 cell lines. J. Ethnopharmacol., 124(2), 251-256. https://doi.org/10.1016/j.jep.2009.04.030
  • [23] Rajkumar, V., Guha, G., Kumar, R. A. (2011). Antioxidant and anti-cancer potentials of Rheum emodi rhizome extracts. Evidence-based Complementary and Alternative Medicine, 2011, 1-9. https://doi.org/10.1093/ecam/neq048
  • [24] Keser, S., Keser, F., Karatepe, M., Kaygili, O., Tekin, S., Turkoglu, I., Demir, E., Yilmaz, O., Kirbag, S., Sandal, S. (2019). Bioactive contents, In vitro antiradical, antimicrobial and cytotoxic properties of rhubarb (Rheum ribes L.) extracts. Natural product research, 1-5. https://doi.org/10.1080/14786419.2018.1560294
  • [25] Sardari, S., Shokrgozar, M. A., Ghavami, G. (2009). Cheminformatics based selection and cytotoxic effects of herbal extracts. Toxicology in vitro, 23(7), 1412-1421. https://doi.org/10.1016/j.tiv.2009.07.011
  • [26] Achakzai, J. K., Anwar Panezai, M., Kakar, M. A., Kakar, A. M., Kakar, S., Khan, J., Tareen, A. K. (2019). In vitro anticancer MCF-7, anti-inflammatory, and brine shrimp lethality assay (BSLA) and GC-MS analysis of whole plant butanol fraction of Rheum ribes (WBFRR). BioMed research international, 2019. https://doi.org/10.1155/2019/3264846
  • [27] Mega, A., Hartmark Nilsen, M., Leiss, L. W., Tobin, N. P., Miletic, H., Sleire, L., Enger, P. Ø. (2020). Astrocytes enhance glioblastoma growth. Glia, 68(2), 316-327. https://doi.org/10.1002/glia.23718
  • [28] Ismail, S., Haris, K., Abdul Ghani, A. R. I., Abdullah, J. M., Johan, M. F., Mohamed Yusoff, A. A. (2013). Enhanced induction of cell cycle arrest and apoptosis via the mitochondrial membrane potential disruption in human U87 malignant glioma cells by aloe emodin. Journal of Asian natural products research, 15(9), 1003-1012. https://doi.org/10.1080/10286020.2013.818982
  • [29] Tang, Y., Fu, F., Gao, H., Shen, L., Chi, I., Bai, Z. (2019). Art therapy for anxiety, depression, and fatigue in females with breast cancer: A systematic review. Journal of psychosocial oncology, 37(1), 79-95. https://doi.org/10.1080/07347332.2018.1506855
  • [30] Kang, S. C., Lee, C. M., Choung, E. S., Bak, J. P., Bae, J. J., Yoo, H. S., Zee, O. P. (2008). Anti-proliferative effects of estrogen receptor-modulating compounds isolated from Rheum palmatum. Archives of Pharmacal Research, 31(6), 722-726. https://doi.org/10.1007/s12272-001-1218-1
  • [31] Huang, P. H., Huang, C. Y., Chen, M. C., Lee, Y. T., Yue, C. H., Wang, H. Y., Lin, H. (2013). Emodin and aloe-emodin suppress breast cancer cell proliferation through ERα inhibition. Evidence-Based Complementary and Alternative Medicine, 2013. https://doi.org/10.1155/2013/376123
  • [32] Bray, F., Ferlay, J., Soerjomataram, I., Siegel, R. L., Torre, L. A., Jemal, A. (2018). Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: a cancer journal for clinicians, 68(6), 394-424. https://doi.org/10.3322/caac.21492
  • [33] Suboj, P., Babykutty, S., Srinivas, P., Gopala, S. (2012). Aloe emodin induces G2 / M cell cycle arrest and apoptosis via activation of caspase-6 in human colon cancer cells. Pharmacology, 89 (1-2), 91-98. https://doi.org/10.1159/000335659

The antiproliferative potential of isolated emodin and aloe-emodin from Rheum ribes on different cancer cell lines

Year 2020, Volume: 13 Issue: 2, 160 - 168, 15.08.2020

Mehmet Kadir Erdoğan Can Ali Agca İbrahim Halil Geçibesler

https://doi.org/10.46309/biodicon.2020.753046
Cited By: 4

Abstract

Herbal compounds are important resources that used in the treatment of many diseases, and are inspiring in drug design and development. Rheum ribes, a perennial native plant, has potentially diverse medicinal effects, including antioxidant, antibacterial and anti-tumor activity. The key molecules associated with anticancer activity of R. ribes in tumor formation still remains unclear. The present study was aimed to elucidate the antiproliferative effects of two purified compounds, emodin and aloe-emodin, from R. ribes. In our study, chromatographic separation was used to purification of compounds. Experimental 1D and 2D 1H and 13C-NMR spectra helped us to confirm the chemical structures of emodin and aloe-emodin. The viability of human glioblastoma cell line (U373), human breast carcinoma cells (MCF-7), and human colorectal cancer cell line (HT-29) were detected by WST-1 proliferation assay as dose- and time-dependent. The isolated emodin and aloe-emodin from R. ribes, reduced viability of human glioblastoma, breast and colorectal cancer cell lines in dose- and time-dependent manner significantly. These antiproliferative effects may contribute as a possible strategy to the development of new therapeutic approaches in the treatment of cancer.

Keywords

Rheum ribes emodin aloe-emodin kanser glioblastoma

Project Number

BAP-FEF.2017.00.010

References

  • [1] Saklani, A., Kutty, S. K. (2008). Plant-derived compounds in clinical trials. Drug discovery today, 13(3-4), 161-171. https://doi.org/10.1016/j.drudis.2007.10.010
  • [2] Zhou, Y., Zheng, J., Li, Y., Xu, D. P., Li, S., Chen, Y. M., Li, H. B. (2016). Natural polyphenols for prevention and treatment of cancer. Nutrients, 8(8), 515. https://doi.org/10.3390/nu8080515
  • [3] Kashiwada, Y., Nonaka, G. I., Nishioka, I., Yamagishi, T. (1988). Galloyl and hydroxycinnamoylglucoses from rhubarb. Phytochemistry, 27(5), 1473-1477. https://doi.org/10.1016/0031-9422(88)80218-8
  • [4] Öztürk, M., Aydoğmuş-Öztürk, F., Duru, M. E., Topçu, G. (2007). Antioxidant activity of stem and root extracts of Rhubarb (Rheum ribes): An edible medicinal plant. Food chemistry, 103(2), 623-630. https://doi.org/10.1016/j.foodchem.2006.09.005
  • [5] Shockravi, A., Agh Nasiri, K. (1997). Synthesis of 1, 2, 3, 4, 5, 6, 7, 8-Octahydro-9-Ethoxy-10-Hydroxy-1-Anthracenone [OEHA]. Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 16(1), 10-14.
  • [6] Cullen, J. (1966). Rheum L. In PH. Davis (Ed.). Flora of Turkey and the East Aegean Islands (Vol. 2, pp. 268–269). Edinburgh: Edinburgh University Press.
  • [7] Baytop, T. (1999). Rheum ribes L. In T. Baytop (Ed.). Therapy with medicinal plants in turkey (Vol. 1, pp. 319–320). Istanbul: Nobel Tıp Publication Press.
  • [8] Tabata, M., Sezik, E., Honda, G., Yeşilada, E., Fukui, H., Goto, K., Ikeshiro, Y. (1994). Traditional medicine in Turkey III. Folk medicine in East Anatolia, Van and Bitlis provinces. Int. J of Pharmacognosy, 32(1), 3-12. https://doi.org/10.3109/13880209409082966
  • [9] Abu-Irmaileh, B. E., Afifi, F. U. (2003). Herbal medicine in Jordan with special emphasis on commonly used herbs. Journal of Ethnopharmacology, 89(2-3), 193-197. https://doi.org/10.1016/S0378-8741(03)00283-6
  • [10] Ozbek, H., Ceylan, E., Kara, M., Ozgokce, F., Koyuncu, M. (2004). Hypoglycemic effect of Rheum ribes roots in alloxan induced diabetic and normal mice. Scandinavian Journal of Laboratory Animal Science, 31(2), 113-115.
  • [11] Bazzaz, B.S.F., Khajehkaramadin, M., Shokooheizadeh, H.R. (2005). In vitro antibacterial activity of Rheum ribes extract obtained from various plant parts against clinical ısolates of gram-negative pathogens. Iran. J. Pharm. Res, 2, 87-91.
  • [12] Bonjar, G. S. (2004). Evaluation of antibacterial properties of Iranian medicinal-plants against Micrococcus luteus, Serratia marcescens, Klebsiella pneumoniae and Bordetella bronchoseptica. Asian J. Plant Sci, 3(1), 82-86.
  • [13] Bonjar, G. S. (2004). Inhibition of three isolates of Staphylococcus aureus mediated by plants used by Iranian native people. J Med Sci, 4(2), 136-141.
  • [14] Hudson, J. B., Lee, M. K., Sener, B., Erdemoglu, N. (2000). Antiviral activities in extracts of Turkish medicinal plants. Pharmaceutical biology, 38(3), 171-175. https://doi.org/10.1076/1388-0209(200007)3831-SFT171
  • [15] Mericli, A. H., Tuzlaci, E. (1990). Constituents of Rheum ribes. Fitoterapia, 61(4).
  • [16] Tuzlacı, E., Meriçli, A. H. (1991, May). Some studies on Isgın (Rheum ribes) and its distribution in Turkey. In Proceeding of the 9th Symposium on Plant Drugs (16-19 May 1991, Eskisehir), Turkey (pp. 336-341).
  • [17] Tosun, F., Kizilay, C. A. (2003). Anthraquinones and flavonoids from Rheum ribes. J Fac Pharm Ankara, 32, 31-5.
  • [18] Erdoğan, M. K., Ağca, C. A., Aşkın, H. (2019). Enhanced antiproliferative and apoptotic effects of 5-fluorouracil by combined with Pistacia eurycarpa Extracts on human colorectal cancer cells. Biological Diversity and Conservation, 12(1), 27-38. https://doi.org/10.5505/biodicon.2019.57441
  • [19] Barros, I. B. D., Daniel, J. F. D. S., Pinto, J. P., Rezende, M. I., Braz Filho, R., Ferreira, D. T. (2011). Phytochemical and antifungal activity of anthraquinones and root and leaf extracts of Coccoloba mollis on phytopathogens. Brazilian Archives of Biology and Technology, 54(3), 535-541. https://doi.org/10.1590/S1516-89132011000300015
  • [20] Zhang, Y. Z., Lu, Y. H., Wei, D. Z., Chou, G. X., Zhu, E. Y. (2007). Preparative isolation and purification of hydroxyanthraquinones from Rheum tanguticum Maxim. on normal phase silica gel: using a Flash Master Personal system. Preparative biochemistry & biotechnology, 37(3), 185-193. https://doi.org/10.1080/10826060701386661
  • [21] Erdoğan, M. K., Geçibesler, İ. H., Behçet, L. (2020). Chemical constituents, antioxidant, antiproliferative and apoptotic effects of a new endemic Boraginaceae species: Paracaryum bingoelianum. Results in Chemistry, 2, 100032. https://doi.org/10.1016/j.rechem.2020.100032
  • [22] Li, W.Y., Chan, S.W., Guo, D.J., Chung, M.K., Leung, T.Y., Yu, P.H.F. (2009). Water extract of Rheum officinale Baill. induces apoptosis in human lung adenocarcinoma A549 and human breast cancer MCF-7 cell lines. J. Ethnopharmacol., 124(2), 251-256. https://doi.org/10.1016/j.jep.2009.04.030
  • [23] Rajkumar, V., Guha, G., Kumar, R. A. (2011). Antioxidant and anti-cancer potentials of Rheum emodi rhizome extracts. Evidence-based Complementary and Alternative Medicine, 2011, 1-9. https://doi.org/10.1093/ecam/neq048
  • [24] Keser, S., Keser, F., Karatepe, M., Kaygili, O., Tekin, S., Turkoglu, I., Demir, E., Yilmaz, O., Kirbag, S., Sandal, S. (2019). Bioactive contents, In vitro antiradical, antimicrobial and cytotoxic properties of rhubarb (Rheum ribes L.) extracts. Natural product research, 1-5. https://doi.org/10.1080/14786419.2018.1560294
  • [25] Sardari, S., Shokrgozar, M. A., Ghavami, G. (2009). Cheminformatics based selection and cytotoxic effects of herbal extracts. Toxicology in vitro, 23(7), 1412-1421. https://doi.org/10.1016/j.tiv.2009.07.011
  • [26] Achakzai, J. K., Anwar Panezai, M., Kakar, M. A., Kakar, A. M., Kakar, S., Khan, J., Tareen, A. K. (2019). In vitro anticancer MCF-7, anti-inflammatory, and brine shrimp lethality assay (BSLA) and GC-MS analysis of whole plant butanol fraction of Rheum ribes (WBFRR). BioMed research international, 2019. https://doi.org/10.1155/2019/3264846
  • [27] Mega, A., Hartmark Nilsen, M., Leiss, L. W., Tobin, N. P., Miletic, H., Sleire, L., Enger, P. Ø. (2020). Astrocytes enhance glioblastoma growth. Glia, 68(2), 316-327. https://doi.org/10.1002/glia.23718
  • [28] Ismail, S., Haris, K., Abdul Ghani, A. R. I., Abdullah, J. M., Johan, M. F., Mohamed Yusoff, A. A. (2013). Enhanced induction of cell cycle arrest and apoptosis via the mitochondrial membrane potential disruption in human U87 malignant glioma cells by aloe emodin. Journal of Asian natural products research, 15(9), 1003-1012. https://doi.org/10.1080/10286020.2013.818982
  • [29] Tang, Y., Fu, F., Gao, H., Shen, L., Chi, I., Bai, Z. (2019). Art therapy for anxiety, depression, and fatigue in females with breast cancer: A systematic review. Journal of psychosocial oncology, 37(1), 79-95. https://doi.org/10.1080/07347332.2018.1506855
  • [30] Kang, S. C., Lee, C. M., Choung, E. S., Bak, J. P., Bae, J. J., Yoo, H. S., Zee, O. P. (2008). Anti-proliferative effects of estrogen receptor-modulating compounds isolated from Rheum palmatum. Archives of Pharmacal Research, 31(6), 722-726. https://doi.org/10.1007/s12272-001-1218-1
  • [31] Huang, P. H., Huang, C. Y., Chen, M. C., Lee, Y. T., Yue, C. H., Wang, H. Y., Lin, H. (2013). Emodin and aloe-emodin suppress breast cancer cell proliferation through ERα inhibition. Evidence-Based Complementary and Alternative Medicine, 2013. https://doi.org/10.1155/2013/376123
  • [32] Bray, F., Ferlay, J., Soerjomataram, I., Siegel, R. L., Torre, L. A., Jemal, A. (2018). Global cancer statistics 2018: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: a cancer journal for clinicians, 68(6), 394-424. https://doi.org/10.3322/caac.21492
  • [33] Suboj, P., Babykutty, S., Srinivas, P., Gopala, S. (2012). Aloe emodin induces G2 / M cell cycle arrest and apoptosis via activation of caspase-6 in human colon cancer cells. Pharmacology, 89 (1-2), 91-98. https://doi.org/10.1159/000335659
There are 33 citations in total.

Details

Primary Language English
Subjects Biochemistry and Cell Biology (Other)
Journal Section Research Articles
Authors

Mehmet Kadir Erdoğan 0000-0002-1579-5737

Can Ali Agca 0000-0002-0244-3767

İbrahim Halil Geçibesler 0000-0002-4473-2671

Project Number BAP-FEF.2017.00.010
Publication Date August 15, 2020
Submission Date April 15, 2020
Acceptance Date June 30, 2020
Published in Issue Year 2020 Volume: 13 Issue: 2

Cite

APA Erdoğan, M. K., Agca, C. A., & Geçibesler, İ. H. (2020). The antiproliferative potential of isolated emodin and aloe-emodin from Rheum ribes on different cancer cell lines. Biological Diversity and Conservation, 13(2), 160-168. https://doi.org/10.46309/biodicon.2020.753046

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