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ENHANCEMENT OF THE SOLUBILITY OF HERBAL POLYPHENOLIC COMPOUNDS IN THE PRESENCE OF LACTIC ACID BUTYLETHER PEG (200)

Yıl 2019, Cilt: 37 Sayı: 4, 1223 - 1233, 01.12.2019

Öz

Polyphenolic compounds found in some plants are very important for human health because of their antioxidant and some disease healing properties. However polyphenolic compounds have a disadvantage that their bioavailability is low due to their low solubility in water. In this study, a new PEG derivative, lactic acid ester of butylether PEG 200 (PEG-ester) has been synthesized and then it has been interacted with curcumin and morin to improve poor water solubility of these polyphenolic compounds. PEG ester, was found to be miscible with water and significantly improved the water solubility of curcumin and morin. The characterization of emulsion systems formed with PEG-ester in the presence of curcumin and morin were investigated. The amount of curcumin and morin in emulsion systems was carried out by UV/VIS spectrophotometric measurements. Interactions were characterized by FTIR measurements. Solubility and stability studies were performed.

Kaynakça

  • [1] Handique J.G., Baruah J.B. (2002) Polyphenolic compounds: an overview. React. Funct. Polym. 52, 163–188.
  • [2] Zhang J., Li J., Ju Y., Fu Y., Gong T., Zhang Z. (2015) Mechanism of enhanced oral absorption of morin by phospholipid complex based self-nanoemulsifying drug delivery system. Mol. Pharm. 12, 504-513.
  • [3] Prasad S., Tyagi A.K., Aggarwal B.B. (2014) Recent Developments in Delivery, Bioavailability, Absorption and Metabolism of Curcumin: the Golden Pigment from Golden Spice, Cancer Res. Treat. 46, 2-18.
  • [4] Luthra P.M., Singh R., Chandra R. (2001) Therapeutic uses of Curcuma longa (turmeric) Indian J. Clin. Biochem. 16, 153-160.
  • [5] Tian W.X. (2006) Inhibition of Fatty Acid Synthase by Polyphenols. Curr. Med. Chem. 13, 967–977.
  • [6] Cole G.M., Teter B., Frautschy S.A. (2007) Neuroprotectıve effects of curcumın. In: Aggarwal BB, Surh YJ, Shishodia S (eds) The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. Advances in Experimental Medicine and Biology, vol 595. Springer, Boston, MA
  • [7] Rao C.V., Rivenson A., Simi B., Reddy B.S. (1995) Chemoprevention of Colon Carcinogenesis by Dietary Curcumin, a Naturally Occurring Plant Phenolic Compound. Cancer Res. 55, 259-266.
  • [8] Kawamori T., Lubet R., Steele V.E. Kelloff G.J., Kaskey R.B., Rao C.V., Reddy B.S. (1999) Chemopreventive Effect of Curcumin, a Naturally Occurring Anti-Inflammatory Agent, during the Promotion/Progression Stages of Colon Cancer. Cancer Res. 59, 597-601.
  • [9] Cheng A.L., Hsu C.H., Lin J.K. et al (2001) Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. 21, 2895-900.
  • [10] Aggarwal B.B., Kumar A., Bharti A.C. (2003) Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res. 23, 363-398.
  • [11] Kim J., Jeong S.W., Quan H., Jeong C. W., Choi J. I., Bae H. B. (2016) Effect of curcumin (Curcuma longa extract) on LPS-induced acute lung injury is mediated by the activation of AMPK J. Anesth. 30, 100 -108.
  • [12] Menon V.P., Sudheer A.R. (2007) Antıoxidant and anti-inflammatory properties of curcumin. In: Aggarwal B.B., Surh Y.J., Shishodia S. (eds) The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. Advances in Experimental Medicine and Biology, vol. 595. Springer, Boston, MA
  • [13] Piper J.T., Singhal S.S., Salameh M.S., Torman R.T., Awasthi Y.C., Awasthi S. (1998) Mechanisms of anticarcinogenic properties of curcumin: the effect of curcumin on glutathione linked detoxification enzymes in rat liver. Int. J. Biochem. Cell Biol. 30, 445-456.
  • [14] Duvoix A., Blasius R., Delhalle S., Schnekenburger M., Morceau F., Henry E., Dicato M., Diederich M. (2005) Chemopreventive and therapeutic effects of curcumin. Cancer Lett. 223, 181-190.
  • [15] Ghorbani Z., Hekmatdoost A., Mirmiran P. (2014) Anti-hyperglycemic and insulin sensitizer effects of turmeric and its principle constituent curcumin. Int. J. Endocrinol. Metab. 12 (4), e18081.
  • [16] Baum L., Ng A. (2004) Curcumin interaction with copper and iron suggests one possible mechanism of action in Alzheimer's disease animal models. J. Alzheimers Dis. 6, 367-377.
  • [17] Zhang H.Y. (2005) One-compound-multiple-targets strategy to combat Alzheimer's disease. FEBS Letters 579 (24), 5260-5264.
  • [18] Del Prado-Audelo M.L., Caballero-Floran I.H., Meza-Toledo J.A., Mendoza-Munoz N., Gonzalez-Torres M., Floran B., Cortes H, Leyva-Gomez G. (2019) Formulations of Curcumin Nanoparticles for Brain Diseases. Biomolecules 9 (2), 56
  • [19] Heger M., van Golen R.F., Broekgaarden M., Michel M.C .(2014) The molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancer. Pharmacol. Rev. 66 (1), 222-307.
  • [20] Noor H., Cao P., Raleigh D.P. (2012) Morin hydrate inhibits amyloid formation by islet amyloid polypeptide and disaggregates amyloid fibers. Protein Science 21, 373–82.
  • [21] Ghoh P., Bag S., Roy A.S., Subramani E., Chaudhury K., Dasgupta S. (2016) Solubility enhancement of morin and epicatechin through encapsulation in an albumin based nanoparticulate system and their anticancer activity against the MDA-MB-468 breast cancer cell line. RSC Adv 6, 101415-101429.
  • [22] Jangid A.K., Pooja D., Kulhari H. (2018) Determination of solubility, stability and degradation kinetcs of morin hydrate in physiological solutions. RSC Adv. 8, 28836-28842.
  • [23] Saberi-Karimian M., Parizadeh S.M., Ghayour-Mobarhan M., Salahshooh M. M., Dizaji B.F., Safarian H., Javandoost A., Ferns G.A., Sahebkar A., Ahmadinejad M. (2018) Evaluation of the effects of curcumin in patients with metabolic syndrome. Comp. Clin. Pathol. 27, 555-563.
  • [24] Yildiz G., Aydogmus Z., Senkal F., Turan G. (2019) Investigation of curcumin water solubility trough emulsifying with biocompatible polyethylene glycol-based polymers. Food Anal. Methods 12 (10), 2129-2138. [25] Tadros T. (2013) Emulsion Systems. In: Tadros T. (eds) Encyclopedia of Colloid and Interface Science. Springer, Berlin, Heidelberg
  • [26] McClements D.J. (2016) Food emulsions: principles, practices, and techniques. CRC press.
  • [27] Duffus L.J., Norton J.E., Smith P. Norton I. T., Spyropoulos F., (2016) A comparative study on the capacity of a range of food-grade particles to form stable O/W and W/O Pickering emulsions. J Colloid Interface Sci. 473, 9-21.
Yıl 2019, Cilt: 37 Sayı: 4, 1223 - 1233, 01.12.2019

Öz

Kaynakça

  • [1] Handique J.G., Baruah J.B. (2002) Polyphenolic compounds: an overview. React. Funct. Polym. 52, 163–188.
  • [2] Zhang J., Li J., Ju Y., Fu Y., Gong T., Zhang Z. (2015) Mechanism of enhanced oral absorption of morin by phospholipid complex based self-nanoemulsifying drug delivery system. Mol. Pharm. 12, 504-513.
  • [3] Prasad S., Tyagi A.K., Aggarwal B.B. (2014) Recent Developments in Delivery, Bioavailability, Absorption and Metabolism of Curcumin: the Golden Pigment from Golden Spice, Cancer Res. Treat. 46, 2-18.
  • [4] Luthra P.M., Singh R., Chandra R. (2001) Therapeutic uses of Curcuma longa (turmeric) Indian J. Clin. Biochem. 16, 153-160.
  • [5] Tian W.X. (2006) Inhibition of Fatty Acid Synthase by Polyphenols. Curr. Med. Chem. 13, 967–977.
  • [6] Cole G.M., Teter B., Frautschy S.A. (2007) Neuroprotectıve effects of curcumın. In: Aggarwal BB, Surh YJ, Shishodia S (eds) The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. Advances in Experimental Medicine and Biology, vol 595. Springer, Boston, MA
  • [7] Rao C.V., Rivenson A., Simi B., Reddy B.S. (1995) Chemoprevention of Colon Carcinogenesis by Dietary Curcumin, a Naturally Occurring Plant Phenolic Compound. Cancer Res. 55, 259-266.
  • [8] Kawamori T., Lubet R., Steele V.E. Kelloff G.J., Kaskey R.B., Rao C.V., Reddy B.S. (1999) Chemopreventive Effect of Curcumin, a Naturally Occurring Anti-Inflammatory Agent, during the Promotion/Progression Stages of Colon Cancer. Cancer Res. 59, 597-601.
  • [9] Cheng A.L., Hsu C.H., Lin J.K. et al (2001) Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. 21, 2895-900.
  • [10] Aggarwal B.B., Kumar A., Bharti A.C. (2003) Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res. 23, 363-398.
  • [11] Kim J., Jeong S.W., Quan H., Jeong C. W., Choi J. I., Bae H. B. (2016) Effect of curcumin (Curcuma longa extract) on LPS-induced acute lung injury is mediated by the activation of AMPK J. Anesth. 30, 100 -108.
  • [12] Menon V.P., Sudheer A.R. (2007) Antıoxidant and anti-inflammatory properties of curcumin. In: Aggarwal B.B., Surh Y.J., Shishodia S. (eds) The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. Advances in Experimental Medicine and Biology, vol. 595. Springer, Boston, MA
  • [13] Piper J.T., Singhal S.S., Salameh M.S., Torman R.T., Awasthi Y.C., Awasthi S. (1998) Mechanisms of anticarcinogenic properties of curcumin: the effect of curcumin on glutathione linked detoxification enzymes in rat liver. Int. J. Biochem. Cell Biol. 30, 445-456.
  • [14] Duvoix A., Blasius R., Delhalle S., Schnekenburger M., Morceau F., Henry E., Dicato M., Diederich M. (2005) Chemopreventive and therapeutic effects of curcumin. Cancer Lett. 223, 181-190.
  • [15] Ghorbani Z., Hekmatdoost A., Mirmiran P. (2014) Anti-hyperglycemic and insulin sensitizer effects of turmeric and its principle constituent curcumin. Int. J. Endocrinol. Metab. 12 (4), e18081.
  • [16] Baum L., Ng A. (2004) Curcumin interaction with copper and iron suggests one possible mechanism of action in Alzheimer's disease animal models. J. Alzheimers Dis. 6, 367-377.
  • [17] Zhang H.Y. (2005) One-compound-multiple-targets strategy to combat Alzheimer's disease. FEBS Letters 579 (24), 5260-5264.
  • [18] Del Prado-Audelo M.L., Caballero-Floran I.H., Meza-Toledo J.A., Mendoza-Munoz N., Gonzalez-Torres M., Floran B., Cortes H, Leyva-Gomez G. (2019) Formulations of Curcumin Nanoparticles for Brain Diseases. Biomolecules 9 (2), 56
  • [19] Heger M., van Golen R.F., Broekgaarden M., Michel M.C .(2014) The molecular basis for the pharmacokinetics and pharmacodynamics of curcumin and its metabolites in relation to cancer. Pharmacol. Rev. 66 (1), 222-307.
  • [20] Noor H., Cao P., Raleigh D.P. (2012) Morin hydrate inhibits amyloid formation by islet amyloid polypeptide and disaggregates amyloid fibers. Protein Science 21, 373–82.
  • [21] Ghoh P., Bag S., Roy A.S., Subramani E., Chaudhury K., Dasgupta S. (2016) Solubility enhancement of morin and epicatechin through encapsulation in an albumin based nanoparticulate system and their anticancer activity against the MDA-MB-468 breast cancer cell line. RSC Adv 6, 101415-101429.
  • [22] Jangid A.K., Pooja D., Kulhari H. (2018) Determination of solubility, stability and degradation kinetcs of morin hydrate in physiological solutions. RSC Adv. 8, 28836-28842.
  • [23] Saberi-Karimian M., Parizadeh S.M., Ghayour-Mobarhan M., Salahshooh M. M., Dizaji B.F., Safarian H., Javandoost A., Ferns G.A., Sahebkar A., Ahmadinejad M. (2018) Evaluation of the effects of curcumin in patients with metabolic syndrome. Comp. Clin. Pathol. 27, 555-563.
  • [24] Yildiz G., Aydogmus Z., Senkal F., Turan G. (2019) Investigation of curcumin water solubility trough emulsifying with biocompatible polyethylene glycol-based polymers. Food Anal. Methods 12 (10), 2129-2138. [25] Tadros T. (2013) Emulsion Systems. In: Tadros T. (eds) Encyclopedia of Colloid and Interface Science. Springer, Berlin, Heidelberg
  • [26] McClements D.J. (2016) Food emulsions: principles, practices, and techniques. CRC press.
  • [27] Duffus L.J., Norton J.E., Smith P. Norton I. T., Spyropoulos F., (2016) A comparative study on the capacity of a range of food-grade particles to form stable O/W and W/O Pickering emulsions. J Colloid Interface Sci. 473, 9-21.
Toplam 26 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Research Articles
Yazarlar

Gulcemal Yıldız Bu kişi benim 0000-0002-6076-7452

Bahire Filiz Senkal Bu kişi benim 0000-0002-1616-6828

Ebru Teknecı Bu kişi benim 0000-0002-7764-1880

Yayımlanma Tarihi 1 Aralık 2019
Gönderilme Tarihi 20 Eylül 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 37 Sayı: 4

Kaynak Göster

Vancouver Yıldız G, Senkal BF, Teknecı E. ENHANCEMENT OF THE SOLUBILITY OF HERBAL POLYPHENOLIC COMPOUNDS IN THE PRESENCE OF LACTIC ACID BUTYLETHER PEG (200). SIGMA. 2019;37(4):1223-3.

IMPORTANT NOTE: JOURNAL SUBMISSION LINK https://eds.yildiz.edu.tr/sigma/