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Investigation of Sterol structures and biological activities in Cochineal and Hibiscus sabdariffa extracts

Year 2024, Volume: 11 Issue: 2, 266 - 276

Dilek Bahar Nilgün Kuşçulu Mehmet Çadır

https://doi.org/10.21448/ijsm.1335924

Abstract

In the future, it is necessary to discover natural resources with no or less toxicity and side effects instead of synthetic drugs. Therefore, it is crucial to recognize, isolate, measure, and reveal the biological activities of substances in the structure of natural resources. In this study, the two extracts prepared from the plant (Hibiscus sabdariffa) and the insect (Dactylopius coccus) were examined. Sampling of the released substances was performed using Gas-Chromatography-Mass Spectrometry (GC-MS). In addition, viability, apoptosis, and oxidative stress of the derivatized samples were determined. Due to the biological differences between the samples, the chemical structures observed in the GC-MS analysis were not the same. It was observed that stigmasterol and its derivatives were found in the pomegranate sample, whereas naphthol and its derivatives were more abundant in the Cochineal insect sample. The cell viability increased with increasing concentrations of stigmasterol, which is present in large amounts in the structure of the pomegranate flower. However, the cell viability decreased with the Cochineal insect sample. Apoptosis and oxidative stress test results were also found to be different and contrasted for both samples. Therefore, the present study presents a new, natural, and different source that can be used as an antiviral and anticancer agent.

Keywords

Cochineal Naphthol Sterol structure Cell culture Cell viability

References

  • Adeyemi, D.O., Ukwenya, V.O., Obuotor, E. M., & Adewole, S.O. (2014). Anti-hepatotoxic activities of Hibiscus sabdariffa L. in animal model of streptozotocin diabetes-induced liver damage. BMC Complementary and Alternative Medicine, 14, 1 11. https://doi.org/10.1186/1472-6882-14-277
  • Baaka, N. (2022). Sustainable dyeing of wool fabric using Kermes Oak (Quercus Coccifera L) as source of natural colorant. Journal of Natural Fibers, 19(1), 37 45. https://doi.org/10.1080/15440478.2020.1726250
  • Belay K, & Sisay M. (2014) Phytochemical constituents and physicochemical properties of medicinal plant (Moringa Oleifera) around Bule Hora. Chemistry and Materials Research. 6(7).
  • Borges, M.E., Tejera, R.L., Díaz, L., Esparza, P., & Ibáñez, E. (2012). Natural dyes extraction from cochineal (Dactylopius coccus). New extraction methods. Food Chemistry, 132(4), 1855-1860. https://doi.org/10.1016/j.foodchem.2011.12.018
  • Chun-Guang, W., Jun-Qing, Y., Bei-Zhong, L., Dan-Ting, J., Chong, W., Liang, Z., & Yan, W. (2010). Anti-tumor activity of emodin against human chronic myelocytic leukemia K562 cell lines in vitro and in vivo. European Journal of Pharmacology, 627(1-3), 33-41. https://pubmed.ncbi.nlm.nih.gov/19857484/
  • Czerwonka, A., Kawka, K., Cykier, K., Lemieszek, M.K., & Rzeski, W. (2017). Evaluation of anticancer activity of water and juice extracts of young Hordeum vulgare in human cancer cell lines HT-29 and A549. Annals of Agricultural and Environmental Medicine, 24(2). https://doi.org/10.26444/aaem/74714
  • Dapson, R.W. (2007). The history, chemistry and modes of action of carmine and related dyes. Biotechnic & Histochemistry, 82(4 5), 173 187. https://doi.org/10.1080/10520290701704188.
  • Deveoglu, O. (2020). A review on cochineal (Dactylopius Coccus Costa) dye. Research Journal of Recent Sciences, 2277, 2502.
  • Esmeeta, A., Adhikary, S., Dharshnaa, V., Swarnamughi, P., Maqsummiya, Z.U., Banerjee, A., Pathak, S., & Duttaroy, A.K. (2022). Plant-derived bioactive compounds in colon cancer treatment: An updated review. Biomedicine & Pharmacotherapy, 153, 13384. https://doi.org/10.1016/j.biopha.2022.113384
  • Gabrielli, L., Origgi, D., Zampella, G., Bertini, L., Bonetti, S., Vaccaro, G., Cipolla, L. (2018). Towards hydrophobic carminic acid derivatives and their incorporation in polyacrylates. Royal Society Open Science, 5(7), 172399. https://doi.org/10.1098/rsos.172399
  • Geetha, B, & Judia Harriet, S.V. (2013) Extraction of natural dyes from plants. International Journal of Chemistry and Pharmaceutical Sciences 1(8): 502-509.
  • González, M., Méndez, J., Carnero, A., Lobo, M.G., & Afonso, A. (2002). Optimizing conditions for the extraction of pigments in cochineals (Dactylopius coccus Costa) using response surface methodology. Journal of Agricultural and Food Chemistry, 50(24), 6968-6974. https://doi.org/10.1021/jf025756r
  • González, E.A., García, E.M., & Nazareno, M.A. (2010). Free radical scavenging capacity and antioxidant activity of cochineal (Dactylopius coccus C.) extracts. Food Chemistry, 119(1), 358-362. https://doi.org/10.1016/j.foodchem.2009.06.030
  • Guo, Y.H., Ma, L.Y., Zheng, H., Zhang, H., Gan, J., Li, K. (2010). Free radical scavenging capacity of carminic acid. Food Science, 31, 73-76.
  • Hsu, H.J., Huang, R.F., Kao, T.H., Inbaraj, B.S., & Chen, B.H. (2017). Preparation of carotenoid extracts and nanoemulsions from Lycium barbarum L. and their effects on growth of HT 29 colon cancer cells. Nanotechnology, 28(13), 135103. https://doi.org/10.1088/1361-6528/aa5e86
  • Kim, E.J., Lee, Y.J., Shin, H.K., & Park, J.H.Y. (2005). Induction of apoptosis by the aqueous extract of Rubus coreanum in HT-29 human colon cancer cells. Nutrition, 21(11-12), 1141-1148. https://doi.org/10.1016/j.nut.2005.02.012
  • Kumar, D., Kumar, S., & Shekhar, C. (2020). Nutritional components in green leafy vegetables: A review. Journal of Pharmacognosy and Phytochemistry, 9(5), 2498-2502.
  • Li, C., & Wang, M.H. (2013). Aristolochia debilis Sieb. et Zucc. induces apoptosis and reactive oxygen species in the HT-29 human colon cancer cell line. Cancer Biotherapy and Radiopharmaceuticals, 28(10), 717-724. https://doi.org/10.1089/cbr.2013.1486
  • Li, Q., Xu, Q., Tan, J., Hu, L., Ge, C., Xu, M. (2021). Carminic acid supplementation protects against fructose-induced kidney injury mainly through suppressing inflammation and oxidative stress via improving Nrf-2 signaling. Aging (Albany NY), 13(7), 10326. https://doi.org/10.18632/aging.202794
  • Mármol, I., Sánchez-de-Diego, C., Pradilla Dieste, A., Cerrada, E., & Rodriguez Yoldi, M.J. (2017). Colorectal carcinoma: a general overview and future perspectives in colorectal cancer. International Journal of Molecular Sciences, 18(1), 197. https://doi.org/10.3390/ijms18010197
  • Mata, R., Nakkala, J.R., & Sadras, S.R. (2016). Polyphenol stabilized colloidal gold nanoparticles from Abutilon indicum leaf extract induce apoptosis in HT-29 colon cancer cells. Colloids and Surfaces B: Biointerfaces, 143, 499 510. https://doi.org/10.1016/j.colsurfb.2016.03.069
  • Nallar, M., Tenaglia, N., Morose, G., & Wong, H.W. (2021). Safer solvent blends for food, dye, and environmental analyses using reversed-phase high performance liquid chromatography. Chromatographia, 84(8), 769-780. https://doi.org/10.1007/s10337-021-04061-8
  • Nemeikaitė-Čėnienė, A., Sergedienė, E., Nivinskas, H., & Čėnas, N. (2002). Cytotoxicity of natural hydroxyanthraquinones: Role of oxidative stress. Zeitschrift für Naturforschung C, 57(9-10), 822-827. https://doi.org/10.1515/znc-2002-9-1012
  • Nguyen, C., Baskaran, K., Pupulin, A., Ruvinov, I., Zaitoon, O., Grewal, S., & Pandey, S. (2019). Hibiscus flower extract selectively induces apoptosis in breast cancer cells and positively interacts with common chemotherapeutics. BMC Complementary and Alternative Medicine, 19(1), 1-14. https://doi.org/10.1186/s12906-019-2505-9
  • Obeng, E. (2020). Apoptosis (programmed cell death) and its signals-A review. Brazilian Journal of Biology, 81, 1133-1143. https://doi.org/10.1590/1519-6984.228437
  • Ogunyemi, O.M., Gyebi, G.A., Elfiky, A.A., Afolabi, S.O., Ogunro, O.B., Adegunloye, A.P., & Ibrahim, I.M. (2020). Alkaloids and flavonoids from African phytochemicals as potential inhibitors of SARS-Cov-2 RNA-dependent RNA polymerase: an in silico perspective. Antiviral Chemistry and Chemotherapy, 28. https://doi.org/10.1177/2040206620984076
  • Rouhollahi, E., Zorofchian Moghadamtousi, S., Paydar, M., Fadaeinasab, M., Zahedifard, M., Hajrezaie, M., Mohamed, Z. (2015). Inhibitory effect of Curcuma purpurascens BI. rhizome on HT-29 colon cancer cells through mitochondrial-dependent apoptosis pathway. BMC Complementary and Alternative Medicine, 15(1), 1-12. https://doi.org/10.1186/s12906-015-0534-6
  • Saxena, S., Raja, A.S.M. (2014). Natural dyes: sources, chemistry, application and sustainability issues. Muthu, S. S. (Ed), Roadmap to sustainable textiles and clothing: eco-friendly raw materials, technologies, and processing methods (pp. 37-80). Singapore: Springer Singapore.
  • Serrano, A., Sousa, M.M., Hallett, J., Lopes, J.A., Oliveira, M.C. (2011). Analysis of natural red dyes (cochineal) in textiles of historical importance using HPLC and multivariate data analysis. Analytical and Bioanalytical Chemistry, 401, 735 743. https://pubmed.ncbi.nlm.nih.gov/21626194/
  • Singh R. (2017) Sources of natural nye - A critical review. International Journal of Engineering, Science and Mathematics, 6(5), 180-185.
  • Srinivas, G., Anto, R.J., Srinivas, P., Vidhyalakshmi, S., Senan, V.P., & Karunagaran, D. (2003). Emodin induces apoptosis of human cervical cancer cells through poly (ADP-ribose) polymerase cleavage and activation of caspase-9. European Journal of Pharmacology, 473(2-3), 117-125. https://doi.org/10.1016/s0014-2999(03)01976-9
  • Sunkara, R., Shackelford, L., Walker, L., & Verghese, M. (2015). Inhibition of chemically-induced colon cancer by dietary treatment of Hibiscus sabdariffa L. Dried Calyx in rats. Food and Nutrition Sciences, 6(12), 1174. https://doi.org/ 10.4236/fns.2015.612123
  • Telford, W.G., King, L.E., & Fraker, P.J. (1992). Comparative evaluation of several DNA binding dyes in the detection of apoptosis‐associated chromatin degradation by flow cytometry. Cytometry: The Journal of the International Society for Analytical Cytology, 13(2), 137-143. https://doi.org/10.1002/cyto.990130205
  • Yousaf, M.M., Majeed, M., Hussain, M., Shah, M.J., Ahmad, B., Ghazali, H.M.Z.U., & Muhammad, R.W. (2018). Calcium alginate entrapment of Aspergillus nidulans IMPP-0785 laccase for enhanced enzyme catalytic ability, thermost ability and dye-decolorization. Bangladesh Journal of Botany, 47(4), 903-909. https://doi.org/10.3329/bjb.v47i4.47380

Investigation of Sterol structures and biological activities in Cochineal and Hibiscus sabdariffa extracts

Year 2024, Volume: 11 Issue: 2, 266 - 276

Dilek Bahar Nilgün Kuşçulu Mehmet Çadır

https://doi.org/10.21448/ijsm.1335924

Abstract

In the future, it is necessary to discover natural resources with no or less toxicity and side effects instead of synthetic drugs. Therefore, it is crucial to recognize, isolate, measure, and reveal the biological activities of substances in the structure of natural resources. In this study, the two extracts prepared from the plant (Hibiscus sabdariffa) and the insect (Dactylopius coccus) were examined. Sampling of the released substances was performed using Gas-Chromatography-Mass Spectrometry (GC-MS). In addition, viability, apoptosis, and oxidative stress of the derivatized samples were determined. Due to the biological differences between the samples, the chemical structures observed in the GC-MS analysis were not the same. It was observed that stigmasterol and its derivatives were found in the pomegranate sample, whereas naphthol and its derivatives were more abundant in the Cochineal insect sample. The cell viability increased with increasing concentrations of stigmasterol, which is present in large amounts in the structure of the pomegranate flower. However, the cell viability decreased with the Cochineal insect sample. Apoptosis and oxidative stress test results were also found to be different and contrasted for both samples. Therefore, the present study presents a new, natural, and different source that can be used as an antiviral and anticancer agent.

Keywords

Cochineal Naphthol Sterol structure Cell culture Cell viability

References

  • Adeyemi, D.O., Ukwenya, V.O., Obuotor, E. M., & Adewole, S.O. (2014). Anti-hepatotoxic activities of Hibiscus sabdariffa L. in animal model of streptozotocin diabetes-induced liver damage. BMC Complementary and Alternative Medicine, 14, 1 11. https://doi.org/10.1186/1472-6882-14-277
  • Baaka, N. (2022). Sustainable dyeing of wool fabric using Kermes Oak (Quercus Coccifera L) as source of natural colorant. Journal of Natural Fibers, 19(1), 37 45. https://doi.org/10.1080/15440478.2020.1726250
  • Belay K, & Sisay M. (2014) Phytochemical constituents and physicochemical properties of medicinal plant (Moringa Oleifera) around Bule Hora. Chemistry and Materials Research. 6(7).
  • Borges, M.E., Tejera, R.L., Díaz, L., Esparza, P., & Ibáñez, E. (2012). Natural dyes extraction from cochineal (Dactylopius coccus). New extraction methods. Food Chemistry, 132(4), 1855-1860. https://doi.org/10.1016/j.foodchem.2011.12.018
  • Chun-Guang, W., Jun-Qing, Y., Bei-Zhong, L., Dan-Ting, J., Chong, W., Liang, Z., & Yan, W. (2010). Anti-tumor activity of emodin against human chronic myelocytic leukemia K562 cell lines in vitro and in vivo. European Journal of Pharmacology, 627(1-3), 33-41. https://pubmed.ncbi.nlm.nih.gov/19857484/
  • Czerwonka, A., Kawka, K., Cykier, K., Lemieszek, M.K., & Rzeski, W. (2017). Evaluation of anticancer activity of water and juice extracts of young Hordeum vulgare in human cancer cell lines HT-29 and A549. Annals of Agricultural and Environmental Medicine, 24(2). https://doi.org/10.26444/aaem/74714
  • Dapson, R.W. (2007). The history, chemistry and modes of action of carmine and related dyes. Biotechnic & Histochemistry, 82(4 5), 173 187. https://doi.org/10.1080/10520290701704188.
  • Deveoglu, O. (2020). A review on cochineal (Dactylopius Coccus Costa) dye. Research Journal of Recent Sciences, 2277, 2502.
  • Esmeeta, A., Adhikary, S., Dharshnaa, V., Swarnamughi, P., Maqsummiya, Z.U., Banerjee, A., Pathak, S., & Duttaroy, A.K. (2022). Plant-derived bioactive compounds in colon cancer treatment: An updated review. Biomedicine & Pharmacotherapy, 153, 13384. https://doi.org/10.1016/j.biopha.2022.113384
  • Gabrielli, L., Origgi, D., Zampella, G., Bertini, L., Bonetti, S., Vaccaro, G., Cipolla, L. (2018). Towards hydrophobic carminic acid derivatives and their incorporation in polyacrylates. Royal Society Open Science, 5(7), 172399. https://doi.org/10.1098/rsos.172399
  • Geetha, B, & Judia Harriet, S.V. (2013) Extraction of natural dyes from plants. International Journal of Chemistry and Pharmaceutical Sciences 1(8): 502-509.
  • González, M., Méndez, J., Carnero, A., Lobo, M.G., & Afonso, A. (2002). Optimizing conditions for the extraction of pigments in cochineals (Dactylopius coccus Costa) using response surface methodology. Journal of Agricultural and Food Chemistry, 50(24), 6968-6974. https://doi.org/10.1021/jf025756r
  • González, E.A., García, E.M., & Nazareno, M.A. (2010). Free radical scavenging capacity and antioxidant activity of cochineal (Dactylopius coccus C.) extracts. Food Chemistry, 119(1), 358-362. https://doi.org/10.1016/j.foodchem.2009.06.030
  • Guo, Y.H., Ma, L.Y., Zheng, H., Zhang, H., Gan, J., Li, K. (2010). Free radical scavenging capacity of carminic acid. Food Science, 31, 73-76.
  • Hsu, H.J., Huang, R.F., Kao, T.H., Inbaraj, B.S., & Chen, B.H. (2017). Preparation of carotenoid extracts and nanoemulsions from Lycium barbarum L. and their effects on growth of HT 29 colon cancer cells. Nanotechnology, 28(13), 135103. https://doi.org/10.1088/1361-6528/aa5e86
  • Kim, E.J., Lee, Y.J., Shin, H.K., & Park, J.H.Y. (2005). Induction of apoptosis by the aqueous extract of Rubus coreanum in HT-29 human colon cancer cells. Nutrition, 21(11-12), 1141-1148. https://doi.org/10.1016/j.nut.2005.02.012
  • Kumar, D., Kumar, S., & Shekhar, C. (2020). Nutritional components in green leafy vegetables: A review. Journal of Pharmacognosy and Phytochemistry, 9(5), 2498-2502.
  • Li, C., & Wang, M.H. (2013). Aristolochia debilis Sieb. et Zucc. induces apoptosis and reactive oxygen species in the HT-29 human colon cancer cell line. Cancer Biotherapy and Radiopharmaceuticals, 28(10), 717-724. https://doi.org/10.1089/cbr.2013.1486
  • Li, Q., Xu, Q., Tan, J., Hu, L., Ge, C., Xu, M. (2021). Carminic acid supplementation protects against fructose-induced kidney injury mainly through suppressing inflammation and oxidative stress via improving Nrf-2 signaling. Aging (Albany NY), 13(7), 10326. https://doi.org/10.18632/aging.202794
  • Mármol, I., Sánchez-de-Diego, C., Pradilla Dieste, A., Cerrada, E., & Rodriguez Yoldi, M.J. (2017). Colorectal carcinoma: a general overview and future perspectives in colorectal cancer. International Journal of Molecular Sciences, 18(1), 197. https://doi.org/10.3390/ijms18010197
  • Mata, R., Nakkala, J.R., & Sadras, S.R. (2016). Polyphenol stabilized colloidal gold nanoparticles from Abutilon indicum leaf extract induce apoptosis in HT-29 colon cancer cells. Colloids and Surfaces B: Biointerfaces, 143, 499 510. https://doi.org/10.1016/j.colsurfb.2016.03.069
  • Nallar, M., Tenaglia, N., Morose, G., & Wong, H.W. (2021). Safer solvent blends for food, dye, and environmental analyses using reversed-phase high performance liquid chromatography. Chromatographia, 84(8), 769-780. https://doi.org/10.1007/s10337-021-04061-8
  • Nemeikaitė-Čėnienė, A., Sergedienė, E., Nivinskas, H., & Čėnas, N. (2002). Cytotoxicity of natural hydroxyanthraquinones: Role of oxidative stress. Zeitschrift für Naturforschung C, 57(9-10), 822-827. https://doi.org/10.1515/znc-2002-9-1012
  • Nguyen, C., Baskaran, K., Pupulin, A., Ruvinov, I., Zaitoon, O., Grewal, S., & Pandey, S. (2019). Hibiscus flower extract selectively induces apoptosis in breast cancer cells and positively interacts with common chemotherapeutics. BMC Complementary and Alternative Medicine, 19(1), 1-14. https://doi.org/10.1186/s12906-019-2505-9
  • Obeng, E. (2020). Apoptosis (programmed cell death) and its signals-A review. Brazilian Journal of Biology, 81, 1133-1143. https://doi.org/10.1590/1519-6984.228437
  • Ogunyemi, O.M., Gyebi, G.A., Elfiky, A.A., Afolabi, S.O., Ogunro, O.B., Adegunloye, A.P., & Ibrahim, I.M. (2020). Alkaloids and flavonoids from African phytochemicals as potential inhibitors of SARS-Cov-2 RNA-dependent RNA polymerase: an in silico perspective. Antiviral Chemistry and Chemotherapy, 28. https://doi.org/10.1177/2040206620984076
  • Rouhollahi, E., Zorofchian Moghadamtousi, S., Paydar, M., Fadaeinasab, M., Zahedifard, M., Hajrezaie, M., Mohamed, Z. (2015). Inhibitory effect of Curcuma purpurascens BI. rhizome on HT-29 colon cancer cells through mitochondrial-dependent apoptosis pathway. BMC Complementary and Alternative Medicine, 15(1), 1-12. https://doi.org/10.1186/s12906-015-0534-6
  • Saxena, S., Raja, A.S.M. (2014). Natural dyes: sources, chemistry, application and sustainability issues. Muthu, S. S. (Ed), Roadmap to sustainable textiles and clothing: eco-friendly raw materials, technologies, and processing methods (pp. 37-80). Singapore: Springer Singapore.
  • Serrano, A., Sousa, M.M., Hallett, J., Lopes, J.A., Oliveira, M.C. (2011). Analysis of natural red dyes (cochineal) in textiles of historical importance using HPLC and multivariate data analysis. Analytical and Bioanalytical Chemistry, 401, 735 743. https://pubmed.ncbi.nlm.nih.gov/21626194/
  • Singh R. (2017) Sources of natural nye - A critical review. International Journal of Engineering, Science and Mathematics, 6(5), 180-185.
  • Srinivas, G., Anto, R.J., Srinivas, P., Vidhyalakshmi, S., Senan, V.P., & Karunagaran, D. (2003). Emodin induces apoptosis of human cervical cancer cells through poly (ADP-ribose) polymerase cleavage and activation of caspase-9. European Journal of Pharmacology, 473(2-3), 117-125. https://doi.org/10.1016/s0014-2999(03)01976-9
  • Sunkara, R., Shackelford, L., Walker, L., & Verghese, M. (2015). Inhibition of chemically-induced colon cancer by dietary treatment of Hibiscus sabdariffa L. Dried Calyx in rats. Food and Nutrition Sciences, 6(12), 1174. https://doi.org/ 10.4236/fns.2015.612123
  • Telford, W.G., King, L.E., & Fraker, P.J. (1992). Comparative evaluation of several DNA binding dyes in the detection of apoptosis‐associated chromatin degradation by flow cytometry. Cytometry: The Journal of the International Society for Analytical Cytology, 13(2), 137-143. https://doi.org/10.1002/cyto.990130205
  • Yousaf, M.M., Majeed, M., Hussain, M., Shah, M.J., Ahmad, B., Ghazali, H.M.Z.U., & Muhammad, R.W. (2018). Calcium alginate entrapment of Aspergillus nidulans IMPP-0785 laccase for enhanced enzyme catalytic ability, thermost ability and dye-decolorization. Bangladesh Journal of Botany, 47(4), 903-909. https://doi.org/10.3329/bjb.v47i4.47380
There are 34 citations in total.

Details

Primary Language English
Subjects Plant Biochemistry, Pharmaceutical Botany
Journal Section Articles
Authors

Dilek Bahar 0000-0002-4916-5071

Nilgün Kuşçulu 0000-0003-3022-4876

Mehmet Çadır This is me 0000-0001-7641-3328

Early Pub Date April 22, 2024
Publication Date
Submission Date August 1, 2023
Published in Issue Year 2024 Volume: 11 Issue: 2

Cite

APA Bahar, D., Kuşçulu, N., & Çadır, M. (2024). Investigation of Sterol structures and biological activities in Cochineal and Hibiscus sabdariffa extracts. International Journal of Secondary Metabolite, 11(2), 266-276. https://doi.org/10.21448/ijsm.1335924
International Journal of Secondary Metabolite

e-ISSN: 2148-6905