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Determination of the isolated Rutin And Quercetin Contents In Syrian Ficus Carica L. Leaves Extracts

Year 2020, Volume: 7 Issue: 1, 197 - 206, 15.02.2020
https://doi.org/10.18596/jotcsa.622442

Abstract



The
major flavonoid glycoside in Syrian ficus leaves extracts (rutin) was
identified quantitatively and isolated, then transformed into its aglycone
(quercetin) by acidic hydrolysis of ethanolic and aqueous extracts. The
influence of the hydrolysis process on isoquercitrin content was investigated
too. The determination was carried out by high performance liquid
chromatography, and the isolation done by thin layer chromatography plates,
then identified by mass spectrum. Results showed that the rutin content in the
ethanolic extract 78.79% was higher than the aqueous one 61.90%, by using
ultrasonic extraction procedure, the quercetin content by hydrolysis process
was more satisfaction in the ethanolic extract 81.00% than the aqueous one
72.53%. Acidic hydrolysis process destroyed some of the isoquercitrin in the
extracts, the detection of isoquercitrin was done qualitatively by noticing the
mass spectrum and the photo diode array spectrum.  Rutin and quercetin were successfully
isolated, the relative peak areas for isolated rutin and quercetin were 99.80%,
96.46%, respectively. It was concluded that rutin can be easily converted into
quercetin by acidic hydrolysis, allowing the use of Syrian ficus leaves
extracts as an optimal cheap natural antioxidants source.




Thanks

Mrs ALyamama Alaskar for her help in acquiring MS spectra.

References

  • 1. Trifunschi S I, Munteanu M F F, Ardelean D G, Orodan M , Osser G M, Gligor R I. Flavonoids and polyphenols content and antioxidant activity of Ficus carica L. extracts from Romania. Zbornik Matice srpske za prirodne nauke.2015; 128: 57-65.‏ 2. Anonymous. The Agricultural Statistics Annual Group,2008. Directorate of Planning and Statistics, Statistics Division,Ministry of Agriculture and Agrarian Reform, Damascus,Syria. 2009.
  • 3. Sirisha N, Sreenivasulu M, Sangeeta K, Chetty C M. Antioxidant Properties of Ficus Spesies – A Review, Int. J. Pharm. Tech. Res. 2010; 2: 2174 - 2182.
  • 4. Solomon A, Golubowicz S, Yablowicz Z, Grossman S, Bergman M, Gottlieb H, et al. Antioxidant Activities and Anthocyanin Content of Fresh Fruits of Common Fig (Ficus carica L.). J. Agric. Food Chem. 2006; 54: 7717 - 7723.
  • 5. Chawla A, Kaur R, Sharma A K. Ficus carica Linn.: A Review on its Pharmacognostic, Phytochemical and Pharmacological Aspects. Int. J. Pharm. Sci Res. 2012; 1: 215 - 232.
  • 6. Rubnov S, Kashman Y, Rabinowitz R, Schlesinger M, Meehoulam R. Suppessors of Cancer Cell Proliferation from Fig (Ficus carica Linn.) Resin: Isolation and Structure Elucidation, J. Natu. Pro. 2001; 64: 993-996.
  • 7. Kruzlicova D, Danihelova M, Veverka M. Quantitative structure-antioxidant activity relationship of quercetin and its new synthetised derivatives. Nova Biotechnologica et Chimica. 2012; 11: 37-44.‏
  • 8. Yashin Ya I, Ryzhnev V Yu, Yashin A Ya, Chernousova N I. Prirodnye antioksidanty. Soderzhanie v pishchevykh produktakh i ikh vliyanie na zdorov’ei starenie cheloveka. 2009.
  • 9. Mauludin R, Müller R H, Keck C M. Development of an oral rutin nanocrystal formulation. Int. J. Pharm Sci Res. 2009; 370: 202-209.
  • 10. Chen H, Zuo Y, Deng Y. Separation and determination of flavonoids and other phenolic compounds in cranberry juice by high-performance liquid chromatography. J. Chrom A. 2001; 913: 387- 395.
  • 11. Wang J, Zhao L L, Sun G X, Liang Y, Wu F A, Chen Z I, et al . A comparison of acidic and enzymatic hydrolysis of rutin. African J. Biotech. 2011; 10: 1460-1466.
  • 12. Seyoum A, Asres K, El-Fiky F K. Structure-radical scavenging activity relationships of flavonoids. Phytochem. 2006; 67: 2058-2070.
  • 13. Vaya J, Mahmood S. Flavonoid content in leaf extracts of the fig (Ficus carica L.), carob (Ceratonia siliqua L.) and pistachio (Pistacia lentiscus L.). Biofactors. 2006;28: 169–175.
  • 14. Takahama U, Tanaka M, Hirota, S, Yamauchi R. Formation of an oxathiolone compound from rutin in acidic mixture of saliva and buckwheat dough: Possibility of its occurrence in the stomach. Food Chem. 2009; 116: 214-219.
  • 15. Kamalakkannan N, Stanely Mainzen P P. Antihyperglycaemic and antioxidant effect of rutin,a polyphenolic flavonoid, in streptozoticin-induced diabetic wistar rats. Basic & Clinical Pharm & Toxi. 2006; 98: 97-103.
  • 16. Je H D, Shin C Y, Park S Y, Yim SH, Kum C, Huh I H, et al. Combination of vitamin C and rutin on neuropathy and lung damage of diabetes mellitus rats. Archives. Pharm. Res. 2002; 25: 184-190.
  • 17. Srinivasan K, Kaul C L, Ramarao P. Partial protective effect of rutin on multiple low dose streptozotocininduced diabetes in mice. Ind. J. Pharm. 2005; 37: 327- 328.
  • 18. Li X, Park N I, Xu H, Woo SH, Park, CH, Park SU. Differential expression of flavonoid biosynthesis genes and accumulation of phenolic compounds in common buckwheat (Fagopyrum esculentum). J. Agri. Food Chem. 2010; 58: 12176- 12181.
  • 19. Scherer RI, Godoy HT. Effects of extraction methods of phenolic compounds from Xanthium strumarium L. and their antioxidant activity. Revista Brasileira de Plantas Medicinais. 2014; 16: 41-46.
  • 20. Zhang Y, Wang D, Yang L, Zhou D, Zhang J. Purification and characterization of flavonoids from the leaves of Zanthoxylum bungeanum and correlation between their structure and antioxidant activity. PLoS One. 2014; 9: e105725.
  • 21. Makino T, Shimizu R, Kanemaru M, Suzuki Y, Moriwaki M, Mizukami H. Enzymatically modified isoquercitrin, α-oligoglucosyl quercetin 3-O-glucoside, is absorbed more easily than other quercetin glycosides or aglycone after oral administration in rats. Bio. Pharm Bull. 2009; 32: 2034-2040.
  • 22. Erlund I. Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability and epidemiology. Nut Res. 2004; 24: 851- 874.
  • 23. Valentova K, Vrba J, Banciřova M, Ulrichova J, Křen V. Isoquercitrin: pharmacology, toxicology, and metabolism. Food. Chem. Toxi. 2014; 68: 267- 282.
  • 24. Yi J, Wu J G, Wu Y B, Peng W. Antioxidant and anti-proliferative activities of flavonoids from Bidens pilosa L var radiate Sch Bip. Tro. J. Pharm. Res.2016; 15: 341-348.
  • 25. Achat S, Tomao V, Madani K, Chibane M, Elmaataoui M, Dangles O, et al. Direct enrichment of olive oil in oleuropein by ultrasound-assisted maceration at laboratory and pilot plant scale. Ultr. Sonochem. 2012; 19: 777-786.‏
  • 26. Chen C, Zhou J, Ji C. Quercetin: A potential drug to reverse multidrug resistance. Life Sci. 2010; 87: 333-338.
  • 27. Cimpoiu C. Analysis of some natural antioxidants by thin-layer chromatography and high performance thin-layer chromatography, J. Liquid Chrom Rel. Tech. 2006; 29: 1125–1142.
  • 28. Şahin S, Şamlı R. Optimization of olive leaf extract obtained by ultrasound-assisted extraction with response surface methodology. Ultr. Sonochem. 2013; 20: 595-602.
Year 2020, Volume: 7 Issue: 1, 197 - 206, 15.02.2020
https://doi.org/10.18596/jotcsa.622442

Abstract

References

  • 1. Trifunschi S I, Munteanu M F F, Ardelean D G, Orodan M , Osser G M, Gligor R I. Flavonoids and polyphenols content and antioxidant activity of Ficus carica L. extracts from Romania. Zbornik Matice srpske za prirodne nauke.2015; 128: 57-65.‏ 2. Anonymous. The Agricultural Statistics Annual Group,2008. Directorate of Planning and Statistics, Statistics Division,Ministry of Agriculture and Agrarian Reform, Damascus,Syria. 2009.
  • 3. Sirisha N, Sreenivasulu M, Sangeeta K, Chetty C M. Antioxidant Properties of Ficus Spesies – A Review, Int. J. Pharm. Tech. Res. 2010; 2: 2174 - 2182.
  • 4. Solomon A, Golubowicz S, Yablowicz Z, Grossman S, Bergman M, Gottlieb H, et al. Antioxidant Activities and Anthocyanin Content of Fresh Fruits of Common Fig (Ficus carica L.). J. Agric. Food Chem. 2006; 54: 7717 - 7723.
  • 5. Chawla A, Kaur R, Sharma A K. Ficus carica Linn.: A Review on its Pharmacognostic, Phytochemical and Pharmacological Aspects. Int. J. Pharm. Sci Res. 2012; 1: 215 - 232.
  • 6. Rubnov S, Kashman Y, Rabinowitz R, Schlesinger M, Meehoulam R. Suppessors of Cancer Cell Proliferation from Fig (Ficus carica Linn.) Resin: Isolation and Structure Elucidation, J. Natu. Pro. 2001; 64: 993-996.
  • 7. Kruzlicova D, Danihelova M, Veverka M. Quantitative structure-antioxidant activity relationship of quercetin and its new synthetised derivatives. Nova Biotechnologica et Chimica. 2012; 11: 37-44.‏
  • 8. Yashin Ya I, Ryzhnev V Yu, Yashin A Ya, Chernousova N I. Prirodnye antioksidanty. Soderzhanie v pishchevykh produktakh i ikh vliyanie na zdorov’ei starenie cheloveka. 2009.
  • 9. Mauludin R, Müller R H, Keck C M. Development of an oral rutin nanocrystal formulation. Int. J. Pharm Sci Res. 2009; 370: 202-209.
  • 10. Chen H, Zuo Y, Deng Y. Separation and determination of flavonoids and other phenolic compounds in cranberry juice by high-performance liquid chromatography. J. Chrom A. 2001; 913: 387- 395.
  • 11. Wang J, Zhao L L, Sun G X, Liang Y, Wu F A, Chen Z I, et al . A comparison of acidic and enzymatic hydrolysis of rutin. African J. Biotech. 2011; 10: 1460-1466.
  • 12. Seyoum A, Asres K, El-Fiky F K. Structure-radical scavenging activity relationships of flavonoids. Phytochem. 2006; 67: 2058-2070.
  • 13. Vaya J, Mahmood S. Flavonoid content in leaf extracts of the fig (Ficus carica L.), carob (Ceratonia siliqua L.) and pistachio (Pistacia lentiscus L.). Biofactors. 2006;28: 169–175.
  • 14. Takahama U, Tanaka M, Hirota, S, Yamauchi R. Formation of an oxathiolone compound from rutin in acidic mixture of saliva and buckwheat dough: Possibility of its occurrence in the stomach. Food Chem. 2009; 116: 214-219.
  • 15. Kamalakkannan N, Stanely Mainzen P P. Antihyperglycaemic and antioxidant effect of rutin,a polyphenolic flavonoid, in streptozoticin-induced diabetic wistar rats. Basic & Clinical Pharm & Toxi. 2006; 98: 97-103.
  • 16. Je H D, Shin C Y, Park S Y, Yim SH, Kum C, Huh I H, et al. Combination of vitamin C and rutin on neuropathy and lung damage of diabetes mellitus rats. Archives. Pharm. Res. 2002; 25: 184-190.
  • 17. Srinivasan K, Kaul C L, Ramarao P. Partial protective effect of rutin on multiple low dose streptozotocininduced diabetes in mice. Ind. J. Pharm. 2005; 37: 327- 328.
  • 18. Li X, Park N I, Xu H, Woo SH, Park, CH, Park SU. Differential expression of flavonoid biosynthesis genes and accumulation of phenolic compounds in common buckwheat (Fagopyrum esculentum). J. Agri. Food Chem. 2010; 58: 12176- 12181.
  • 19. Scherer RI, Godoy HT. Effects of extraction methods of phenolic compounds from Xanthium strumarium L. and their antioxidant activity. Revista Brasileira de Plantas Medicinais. 2014; 16: 41-46.
  • 20. Zhang Y, Wang D, Yang L, Zhou D, Zhang J. Purification and characterization of flavonoids from the leaves of Zanthoxylum bungeanum and correlation between their structure and antioxidant activity. PLoS One. 2014; 9: e105725.
  • 21. Makino T, Shimizu R, Kanemaru M, Suzuki Y, Moriwaki M, Mizukami H. Enzymatically modified isoquercitrin, α-oligoglucosyl quercetin 3-O-glucoside, is absorbed more easily than other quercetin glycosides or aglycone after oral administration in rats. Bio. Pharm Bull. 2009; 32: 2034-2040.
  • 22. Erlund I. Review of the flavonoids quercetin, hesperetin, and naringenin. Dietary sources, bioactivities, bioavailability and epidemiology. Nut Res. 2004; 24: 851- 874.
  • 23. Valentova K, Vrba J, Banciřova M, Ulrichova J, Křen V. Isoquercitrin: pharmacology, toxicology, and metabolism. Food. Chem. Toxi. 2014; 68: 267- 282.
  • 24. Yi J, Wu J G, Wu Y B, Peng W. Antioxidant and anti-proliferative activities of flavonoids from Bidens pilosa L var radiate Sch Bip. Tro. J. Pharm. Res.2016; 15: 341-348.
  • 25. Achat S, Tomao V, Madani K, Chibane M, Elmaataoui M, Dangles O, et al. Direct enrichment of olive oil in oleuropein by ultrasound-assisted maceration at laboratory and pilot plant scale. Ultr. Sonochem. 2012; 19: 777-786.‏
  • 26. Chen C, Zhou J, Ji C. Quercetin: A potential drug to reverse multidrug resistance. Life Sci. 2010; 87: 333-338.
  • 27. Cimpoiu C. Analysis of some natural antioxidants by thin-layer chromatography and high performance thin-layer chromatography, J. Liquid Chrom Rel. Tech. 2006; 29: 1125–1142.
  • 28. Şahin S, Şamlı R. Optimization of olive leaf extract obtained by ultrasound-assisted extraction with response surface methodology. Ultr. Sonochem. 2013; 20: 595-602.
There are 27 citations in total.

Details

Primary Language English
Subjects Analytical Chemistry
Journal Section Articles
Authors

Shaza Alshaal 0000-0001-9350-2912

Manal Daghestani This is me 0000-0003-0344-2982

Francois Karabet This is me 0000-0001-5518-0158

Publication Date February 15, 2020
Submission Date September 20, 2019
Acceptance Date November 27, 2019
Published in Issue Year 2020 Volume: 7 Issue: 1

Cite

Vancouver Alshaal S, Daghestani M, Karabet F. Determination of the isolated Rutin And Quercetin Contents In Syrian Ficus Carica L. Leaves Extracts. JOTCSA. 2020;7(1):197-206.