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Effect of Solvent Polarity on Extraction Yield of Total Flavonoids with Special Emphasis to Glabridin from Glycyrrhiza glabra Roots

Year 2022, Volume: 1 Issue: 47, 1 - 12, 01.03.2022
https://doi.org/10.55262/fabadeczacilik.1078751

Abstract

Different organic solvents (ethanol, dichloromethane, ethyl acetate and acetone) were studied for their effects on the extraction efficiency of glabridin and total flavonoids (TF) from Glycyrrhiza glabra roots. The extract yield of Glycyrrhiza glabra roots was in the range of 3% to 6% following the extraction efficiency in the order ethanol>acetone>ethyl acetate>dichloromethane. A higher extraction yield of TF and glabridin was obtained with dichloromethane, followed by ethyl acetate, acetone and ethanol, indicating that the non-polar solvents help in optimal extraction of TF and glabridin. We also demonstrate for the first time, that the extraction efficiency of the flavonoids is not significantly affected by the use of the recovered solvents except in case of ethanol which reflects that the moisture absorbing capacity of the solvent dictates the extraction efficiency of such compounds. The glycyrrhizin content in all the extract types was rather low (0.1 % to 1%) except for extract prepared with water, where the glycyrrhizin content was ~10% as expected since glycyrrhizin is a polar compound. Interestingly, we observed that ethyl acetate selectively isolated only glabridin with no traces of glycyrrhizin, which is a finding reported for the first time.

References

  • Altemimi, A., Lakhssassi, A., Baharlouei, A., Watson, D.G., Lightfoot, D.A. (2017). Phytochemicals: Extraction, isolation, and identification of bioactive compounds from plant extracts. Plants, 6(4), 1-23. https://doi.org/10.3390/plants6040042
  • Alwan, A.M., Nesrullah, Z., Faraj, E. (2015). Study the effect of ethanolic extract of Glycyrrhiza glabra on pathogenic bacteria. International Journal of Current Microbiology and Applied Sciences, 4(5), 473-484.
  • Ammosov, A.S., Litvinenko, V.I. (2003). Triterpenoids of Plants of Glycyrrhiza L. and Meristotropis Fisch. Et Mey Genuses. Pharmaceutical Chemistry Journal, 37, 83-94. https://doi. org/10.1023/A:1024085610712 .
  • Ao, M., Shi, Y., Cui, Y., Guo, W., Wang, J., Yu L. (2010). Factors influencing Glabridin stability. Natural Products Communications, 5(12), 1907-1912. https://doi.org/10.1177/1934578X1000501214
  • Baptista, C.A.C., Zak, P.W., Bittencourt, A.S. (2013). Upgrading recycled acetone to 100% with molecular sieves. Journal of Plastination, 25(2), 27-32.
  • Bhan, M., Satija, S., Garg, C., Dureja, H., Garg, M. (2017). A novel approach towards green extraction for Glycyrrhitinic acid by ionic liquid-based microwave- assisted extraction and optimization through response surface methodology. Pharmacognosy Journal, 9(6), 866-872. https://doi. org/10.5530/pj.2017.6.136
  • Chandrasekaran, C.V., Deepak, H.B., Thiyagarajan, P., Kathiresan, S., Sangli, G.K, Deepak M.,…Agarwal A. (2011). A Dual inhibitory effect of Glycyrrhiza glabra (GutGardTM) on COX and LOX products. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 18(4), 278–284. https://doi.org/10.1016/j.phymed.2010.08.001
  • Cho, Y., Ryu, J. (2004). Supercritical fluid extraction of glabridin from Glycyrrhiza glabra. Proceedings of the 4th International Conference on Separation Science and Technology, 334 337. https://doi.org/10.1142/9789812702623_0066
  • Damle, M., (2014). Glycyrrhiza glabra (Licorice) - a potent medicinal herb. International Journal of Herbal Medicine, 2(2), 132-136.
  • Hong, J-H., Jung, I-L., Cho, Y-K., Haam, S., Lee, S-Y., Lim, G.,….Ryu, J-H (2019). Preparation of high-quality glabridin extract from Glycyrrhiza glabra. Biotechnology and Bioprocess Engineering, 24, 666–674. https://doi.org/10.1007/s12257-019-0121-7
  • Jalilzadeh-Amin, G., Najarnezhad, V., Anassori, E., Mostafavi, M., Keshipour, H. (2015). Antiulcer properties of Glycyrrhiza glabra L. extract on experimental models of gastric ulcer in mice. Iranian Journal of Pharmaceutical Research, 14(4), 1163-1170.
  • Kaur, R., Kaur, H.P. Dhindsa, A.S. (2013). Glycyrrhiza glabra: a phytopharmacological review. International Journal of Pharmaceutical Sciences and Research, 4(7), 2470-2477.
  • Lee, K.J., Song, Y., Oh, Y.C., Cho, W-K., Ma, J.Y. (2014). Isolation and bioactivity analysis of ethyl acetate extract from Acer tegmentosum using in vitro assay and online screening HPLC-ABTS+ System. Journal of Analytical Methods in Chemistry, 2014, 1-15. https://doi.org/10.1155/2014/150509
  • Li, X., Guo, R., Zhang, X., Li, X. (2012). Extraction of glabridin using imidazolium-based ionic liquids. Separation and Purification Technology, 88, 146–150. https://doi.org/10.1016/j.seppur.2011.12.018
  • Lv, J., Liang, H., Yuan, Q., Xu, Y., Wang, T. (2010). Preparative purification of the major flavonoid glabridin from licorice roots by solid-phase extraction and preparative high-performance liquid chromatography. Separation Science and Technology, 45(8), 1104–1111. https://doi.org/10.1080/01496391003697358
  • Nakagawa, K., Kishida, H., Arai, N., Nishiyama, T., Mae, T. (2004). Licorice flavonoids suppress abdominal fat accumulation and increase in blood glucose level in obese diabetic KK-A(y) mice. Biological and Pharmaceutical Bulletin, 27(11), 1775–1778.
  • Shrikant, K., Shital, P., Atul, S., Shrinivas, B., Sriram, P.(2020). RP-HPLC method development and validation for simultaneous estimation of glabridin, glycyrrhizic Acid and total flavonoids in Glycyrrhiza glabra extract: Stability studies of constituents. Global Journal of Pharmaceutical Sciences, 8(3), 555738. https://doi: 10.19080/GJPPS.2021.08.555738
  • Tan, B., Melius, P.P., Ziegler, P. (1982). A simple gas chromatographic method for the study of organic solvents: Moisture analysis, hygroscopicity, and evaporation. Journal of Chromatographic Science, 1982: 20(5), 213- 217. https://doi.org/10.1093/chromsci/20.5.213
  • Tian, M., Yan, H. (2008). Extraction of glycyrrhizic acid and glabridin from licorice. International Journal of Molecular Sciences, 9(4): 571–577.
  • Vishwanathan, V., Pharande, R., Bannalikar, A.K., Gupta, P., Gupta, U., Mukne, A. (2019). Inhalable liposomes of Glycyrrhiza glabra extract for use in tuberculosis: formulation, in-vitro characterization, in vivo lung deposition, and in vivo pharmacodynamic studies, Drug Development and Industrial Pharmacy, 45, 11-20. https://doi:10.1080/03639045.2018.1513025
  • Wang, L., Yang, R., Yuan, B., Liun, Y., Liu, C. (2015).The antiviral and antimicrobial activities of licorice, a widely used Chinese herb. Acta Pharmaceutica Sinica, B 5(4), 310-315.
  • Wang, Y-C., Yang, Y-S. (2007). Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC. Journal of Chromatography B, 850(1-2), 392–399. https://doi.org/10.1016/j.jchromb.2006.12.032
  • Xu, Y., Yuan, Q., Hou, X., Lin, Y. (2009). Preparative separation of Glabridin from Glycyrrhiza glabra L.Extracts with macroporous resins. Separation Science and Technology, 44(15), 3717–3734. https://doi.org/10.1080/01496390903182933
  • Yewale, S., Farash, Z., Kolhe, S., Sakkan, S., Bhope, S., Ambekar, P.,…Padmanabhan, S. (2020). Benefits of Soleris® over the conventional method for enumeration of microbial load in Salacia herbal extract. Polish Journal of Microbiology, 69(4), 453–462. https://doi.org/10.33073/pjm-2020-048
  • Yip, H.Y., Poh, M.S.W., Chia, Y.Y. (2016). The effects of glycyrrhizic acid and glabridin in the regulation of CXCL5 inflammation gene on acceleration of wound healing. Asian Pacific Journal of Tropical Biomedicine, 6(2), 108–113. https://doi.org/10.1016/j.apjtb.2015.10.009
  • Yokota, T., Nishio, H., Kubota, Y., Mizoguch, M. (1998). The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation. Pigment Cell Research, 11(6), 955-961. https://doi.org/10.1111/j.1600-0749.1998.tb00494.x

Çözücü Polaritesinin Özellikle Glabridin Olmak Üzere Glycyrrhiza glabra Köklerindeki Toplam Flavonoitlerin Ekstraksiyonunun Verimine Etkisi

Year 2022, Volume: 1 Issue: 47, 1 - 12, 01.03.2022
https://doi.org/10.55262/fabadeczacilik.1078751

Abstract

Farklı organik çözücülerin (etanol, diklorometan, etil asetat ve aseton) Glycyrrhiza glabra köklerinden glabridin ve toplam flavonoit (TF) ekstraksiyon verimliliğine etkileri çalışılmıştır.
Glycyrrhiza glabra köklerinden ekstre verimi % 3 ile % 6 aralığında, ekstraksiyon etkinliği etanol> aseton> etil asetat> diklorometan sırası ile bulunmuştur. Diklorometan, ardından etil asetat, aseton ve etanol ile daha yüksek bir TF ve glabridin ektraksiyon verimi elde edilmiştir, bu da TF ve glabridinin en uygun şekilde ekstraksiyonunda polar olmayan çözücülerin etkili olduğunu göstermektedir. Ayrıca flavonoitlerin ektraksiyon verimliliğinin, çözücünün nem absorplama kapasitesinin bu tür bileşiklerin ekstre edilmesinde rol oynadığını yansıtan etanol haricinde, geri kazanılan çözücülerin kullanımından büyük ölçüde etkilenmediği de ilk kez gösterilmiştir. Su ile hazırlanan ekstre haricinde tüm ekstre türlerinde glisirizin içeriği düşük olup % 0,1 ile % 1 aralığındadır, bileşik polar bir bileşik olduğu için su ekstresinde içerik beklendiği gibi ~% 10’dur. İlginç bir şekilde, etil asetatın glisirizin izleri olmadan sadece glabridini seçici olarak izole ettiği ilk kez bildirilen bir bulgu olarak gözlenmiştir.

References

  • Altemimi, A., Lakhssassi, A., Baharlouei, A., Watson, D.G., Lightfoot, D.A. (2017). Phytochemicals: Extraction, isolation, and identification of bioactive compounds from plant extracts. Plants, 6(4), 1-23. https://doi.org/10.3390/plants6040042
  • Alwan, A.M., Nesrullah, Z., Faraj, E. (2015). Study the effect of ethanolic extract of Glycyrrhiza glabra on pathogenic bacteria. International Journal of Current Microbiology and Applied Sciences, 4(5), 473-484.
  • Ammosov, A.S., Litvinenko, V.I. (2003). Triterpenoids of Plants of Glycyrrhiza L. and Meristotropis Fisch. Et Mey Genuses. Pharmaceutical Chemistry Journal, 37, 83-94. https://doi. org/10.1023/A:1024085610712 .
  • Ao, M., Shi, Y., Cui, Y., Guo, W., Wang, J., Yu L. (2010). Factors influencing Glabridin stability. Natural Products Communications, 5(12), 1907-1912. https://doi.org/10.1177/1934578X1000501214
  • Baptista, C.A.C., Zak, P.W., Bittencourt, A.S. (2013). Upgrading recycled acetone to 100% with molecular sieves. Journal of Plastination, 25(2), 27-32.
  • Bhan, M., Satija, S., Garg, C., Dureja, H., Garg, M. (2017). A novel approach towards green extraction for Glycyrrhitinic acid by ionic liquid-based microwave- assisted extraction and optimization through response surface methodology. Pharmacognosy Journal, 9(6), 866-872. https://doi. org/10.5530/pj.2017.6.136
  • Chandrasekaran, C.V., Deepak, H.B., Thiyagarajan, P., Kathiresan, S., Sangli, G.K, Deepak M.,…Agarwal A. (2011). A Dual inhibitory effect of Glycyrrhiza glabra (GutGardTM) on COX and LOX products. Phytomedicine: International Journal of Phytotherapy and Phytopharmacology, 18(4), 278–284. https://doi.org/10.1016/j.phymed.2010.08.001
  • Cho, Y., Ryu, J. (2004). Supercritical fluid extraction of glabridin from Glycyrrhiza glabra. Proceedings of the 4th International Conference on Separation Science and Technology, 334 337. https://doi.org/10.1142/9789812702623_0066
  • Damle, M., (2014). Glycyrrhiza glabra (Licorice) - a potent medicinal herb. International Journal of Herbal Medicine, 2(2), 132-136.
  • Hong, J-H., Jung, I-L., Cho, Y-K., Haam, S., Lee, S-Y., Lim, G.,….Ryu, J-H (2019). Preparation of high-quality glabridin extract from Glycyrrhiza glabra. Biotechnology and Bioprocess Engineering, 24, 666–674. https://doi.org/10.1007/s12257-019-0121-7
  • Jalilzadeh-Amin, G., Najarnezhad, V., Anassori, E., Mostafavi, M., Keshipour, H. (2015). Antiulcer properties of Glycyrrhiza glabra L. extract on experimental models of gastric ulcer in mice. Iranian Journal of Pharmaceutical Research, 14(4), 1163-1170.
  • Kaur, R., Kaur, H.P. Dhindsa, A.S. (2013). Glycyrrhiza glabra: a phytopharmacological review. International Journal of Pharmaceutical Sciences and Research, 4(7), 2470-2477.
  • Lee, K.J., Song, Y., Oh, Y.C., Cho, W-K., Ma, J.Y. (2014). Isolation and bioactivity analysis of ethyl acetate extract from Acer tegmentosum using in vitro assay and online screening HPLC-ABTS+ System. Journal of Analytical Methods in Chemistry, 2014, 1-15. https://doi.org/10.1155/2014/150509
  • Li, X., Guo, R., Zhang, X., Li, X. (2012). Extraction of glabridin using imidazolium-based ionic liquids. Separation and Purification Technology, 88, 146–150. https://doi.org/10.1016/j.seppur.2011.12.018
  • Lv, J., Liang, H., Yuan, Q., Xu, Y., Wang, T. (2010). Preparative purification of the major flavonoid glabridin from licorice roots by solid-phase extraction and preparative high-performance liquid chromatography. Separation Science and Technology, 45(8), 1104–1111. https://doi.org/10.1080/01496391003697358
  • Nakagawa, K., Kishida, H., Arai, N., Nishiyama, T., Mae, T. (2004). Licorice flavonoids suppress abdominal fat accumulation and increase in blood glucose level in obese diabetic KK-A(y) mice. Biological and Pharmaceutical Bulletin, 27(11), 1775–1778.
  • Shrikant, K., Shital, P., Atul, S., Shrinivas, B., Sriram, P.(2020). RP-HPLC method development and validation for simultaneous estimation of glabridin, glycyrrhizic Acid and total flavonoids in Glycyrrhiza glabra extract: Stability studies of constituents. Global Journal of Pharmaceutical Sciences, 8(3), 555738. https://doi: 10.19080/GJPPS.2021.08.555738
  • Tan, B., Melius, P.P., Ziegler, P. (1982). A simple gas chromatographic method for the study of organic solvents: Moisture analysis, hygroscopicity, and evaporation. Journal of Chromatographic Science, 1982: 20(5), 213- 217. https://doi.org/10.1093/chromsci/20.5.213
  • Tian, M., Yan, H. (2008). Extraction of glycyrrhizic acid and glabridin from licorice. International Journal of Molecular Sciences, 9(4): 571–577.
  • Vishwanathan, V., Pharande, R., Bannalikar, A.K., Gupta, P., Gupta, U., Mukne, A. (2019). Inhalable liposomes of Glycyrrhiza glabra extract for use in tuberculosis: formulation, in-vitro characterization, in vivo lung deposition, and in vivo pharmacodynamic studies, Drug Development and Industrial Pharmacy, 45, 11-20. https://doi:10.1080/03639045.2018.1513025
  • Wang, L., Yang, R., Yuan, B., Liun, Y., Liu, C. (2015).The antiviral and antimicrobial activities of licorice, a widely used Chinese herb. Acta Pharmaceutica Sinica, B 5(4), 310-315.
  • Wang, Y-C., Yang, Y-S. (2007). Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC. Journal of Chromatography B, 850(1-2), 392–399. https://doi.org/10.1016/j.jchromb.2006.12.032
  • Xu, Y., Yuan, Q., Hou, X., Lin, Y. (2009). Preparative separation of Glabridin from Glycyrrhiza glabra L.Extracts with macroporous resins. Separation Science and Technology, 44(15), 3717–3734. https://doi.org/10.1080/01496390903182933
  • Yewale, S., Farash, Z., Kolhe, S., Sakkan, S., Bhope, S., Ambekar, P.,…Padmanabhan, S. (2020). Benefits of Soleris® over the conventional method for enumeration of microbial load in Salacia herbal extract. Polish Journal of Microbiology, 69(4), 453–462. https://doi.org/10.33073/pjm-2020-048
  • Yip, H.Y., Poh, M.S.W., Chia, Y.Y. (2016). The effects of glycyrrhizic acid and glabridin in the regulation of CXCL5 inflammation gene on acceleration of wound healing. Asian Pacific Journal of Tropical Biomedicine, 6(2), 108–113. https://doi.org/10.1016/j.apjtb.2015.10.009
  • Yokota, T., Nishio, H., Kubota, Y., Mizoguch, M. (1998). The inhibitory effect of glabridin from licorice extracts on melanogenesis and inflammation. Pigment Cell Research, 11(6), 955-961. https://doi.org/10.1111/j.1600-0749.1998.tb00494.x
There are 26 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Research Articles
Authors

Sadanand Yewale This is me

Zeba Farash This is me

Shrikant Kulkarnı This is me

Shital Palghadmal This is me

Neelam Athawale This is me

Laxman Sawant This is me

Shrinivas Bhope This is me

Sriram Padmanabhan This is me

Publication Date March 1, 2022
Submission Date February 10, 2021
Published in Issue Year 2022 Volume: 1 Issue: 47

Cite

APA Yewale, S., Farash, Z., Kulkarnı, S., Palghadmal, S., et al. (2022). Effect of Solvent Polarity on Extraction Yield of Total Flavonoids with Special Emphasis to Glabridin from Glycyrrhiza glabra Roots. Fabad Journal of Pharmaceutical Sciences, 1(47), 1-12. https://doi.org/10.55262/fabadeczacilik.1078751