Download PDF
Planta Med 2014; 80(17): 1657-1664
DOI: 10.1055/s-0034-1383145
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Recovery of Polyphenols from Rose Oil Distillation Wastewater Using Adsorption Resins – A Pilot Study

Krasimir Rusanov
1   AgroBioInstitute, Agriculture Academy, Sofia, Bulgaria
,
Eliane Garo
2   Institute of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Basel, Switzerland
,
Mila Rusanova
1   AgroBioInstitute, Agriculture Academy, Sofia, Bulgaria
,
Orlando Fertig
2   Institute of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Basel, Switzerland
,
Matthias Hamburger
2   Institute of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Basel, Switzerland
,
Ivan Atanassov
1   AgroBioInstitute, Agriculture Academy, Sofia, Bulgaria
,
Veronika Butterweck
3   Institute for Pharma Technology, School of Life Sciences, University of Applied Sciences Northwestern Switzerland, Muttenz, Switzerland
› Author Affiliations
Further Information

Publication History

received 11 July 2014
revised 08 September 2014

accepted 12 September 2014

Publication Date:
08 October 2014 (online)

    Permissions and Reprints

Abstract

The production of rose oil from rose flowers by water steam distillation leaves a water fraction of the distillate as main part of the waste. Therefore, the rose oil distillation wastewater represents a serious environmental problem due to the high content of polyphenols which are difficult to decompose and have to be considered as biopollutants when discarded into the drainage system and rivers. On the other hand, natural polyphenols are valuable compounds with useful properties as bioactive substances. Until now there is no established practice for processing of rose oil distillation wastewater and utilization of contained substances. Thus, it was the aim of this study to develop a strategy to separate this wastewater into a polyphenol depleted water fraction and a polyphenol enriched fraction which could be developed into innovative value-added products. In a first step, the phytochemical profile of rose oil distillation wastewater was determined. Its HPLC-PDA-MS analysis revealed the presence of flavan-3-ols, flavanones, flavonols and flavones. In a second step, the development of a stepwise concentration of rose oil distillation wastewater was performed. The concentration process includes a filtration process to eliminate suspended solids in the wastewater, followed by adsorption of the contained phenolic compounds onto adsorption resins (XAD and SP). Finally, desorption of the polyphenol fraction from the resin matrix was achieved using ethanol and/or aqueous ethanol. The result of the process was a wastewater low in soluble organic compounds and an enriched polyphenol fraction (RF20 SP-207). The profile of this fraction was similar to that of rose oil distillation wastewater and showed the presence of flavonols such as quercetin and kaempferol glycosides as major metabolites. These compounds were isolated from the enriched polyphenol fraction and their structures confirmed by NMR. In summary, a pilot medium scale system was developed using adsorption resins for the recovery of polyphenols from rose oil distillation wastewater suggesting an industrial scalability of the process.

Key words

Rosa damascena - Rosaceae - rose oil distillation - wastewater management - adsorption resin - polyphenols

Supporting Information

 

  • References

  • 1 Rusanov K, Kovacheva N, Atanassov A, Atanassov I. Rosa damascena Mill., the oil-bearing Damask rose: genetic resources, diversity and perspectives for molecular breeding. Floriculture Ornamental Biotech 2009; 3: 14-20
    PubMedGoogle Scholar
  • 2 Rusanov K, Kovacheva N, Rusanova M, Atanassov I. Traditional Rosa damascena flower harvesting practices evaluated through GC/MS metabolite profiling of flower volatiles. Food Chem 2011; 129: 1851-1859
    CrossrefPubMedGoogle Scholar
  • 3 Kovacheva N, Rusanov K, Atanassov I. Industrial cultivation of oil bearing rose and rose oil production in Bulgaria during 21st century, directions and challenges. Biotechnol Biotech Eq 2010; 24: 1793-1798
    PubMedGoogle Scholar
  • 4 Schieber A, Mihalev K, Berardini N, Mollov P, Carle R. Flavonol glycosides from distilled petals of Rosa damascena Mill. Z Naturforsch 2005; 60: 379-384
    PubMedGoogle Scholar
  • 5 Rusanov KE, Kovacheva NM, Atanassov I. Comparative Gc/Ms analysis of rose flower and distilled oil volatiles of the oil bearing rose Rosa damascena . Biotechnol Biotechnol Eq 2011; 25: 2210-2216
    CrossrefPubMedGoogle Scholar
  • 6 Scalbert A, Johnson IT, Saltmarsh M. Polyphenols: antioxidants and beyond. Am J Clin Nutr 2005; 81 (Suppl. 01) S215-S217
    PubMedGoogle Scholar
  • 7 Daglia M. Polyphenols as antimicrobial agents. Curr Opin Biotech 2012; 23: 174-181
    CrossrefPubMedGoogle Scholar
  • 8 Pan MH, Ho CT. Chemopreventive effects of natural dietary compounds on cancer development. Chem Soc Rev 2008; 37: 2558-2574
    CrossrefPubMedGoogle Scholar
  • 9 Agalias A, Magiatis P, Skaltsounis AL, Mikros E, Tsarbopoulos A, Gikas E, Spanos I, Manios T. A new process for the management of olive oil mill waste water and recovery of natural antioxidants. J Agric Food Chem 2007; 55: 2671-2676
    CrossrefPubMedGoogle Scholar
  • 10 Bertin L, Ferri F, Scoma A, Marchetti L, Fava F. Recovery of high added value natural polyphenols from actual olive mill wastewater through solid phase extraction. Chem Eng J 2011; 171: 1287-1293
    CrossrefPubMedGoogle Scholar
  • 11 Kumar N, Bhandari P, Singh B, Gupta AP, Kaul VK. Reversed phase-HPLC for rapid determination of polyphenols in flowers of rose species. J Sep Sci 2008; 31: 262-267
    CrossrefPubMedGoogle Scholar
  • 12 Mabry TJ, Markham KR, Thomas MB. The systematic identification of flavonoids. Berlin, New York: Springer-Publisher; 1970: 354
    CrossrefGoogle Scholar
  • 13 Velioglu YS, Mazza G. Characterization of flavonoids in petals of Rosa damascena by HPLC and spectral-analysis. J Agric Food Chem 1991; 39: 463-467
    CrossrefPubMedGoogle Scholar
  • 14 Markham KR, Geiger H, Jaggy H. Kaempferol-3-O-glucosyl(1–2)rhamnoside from Ginkgo biloba and a reappraisal of other gluco(1–2, 1–3 and 1–4)rhamnoside structures. Phytochem 1992; 31: 1009-1011
    CrossrefPubMedGoogle Scholar
  • 15 Markham KR, Ternai B. C-13 NMR of flavonoids. 2. Flavonoids other then flavone and flavonol aglycones. Tetrahedron 1976; 32: 2607-2612
    CrossrefPubMedGoogle Scholar
  • 16 Markham KR, Ternai B, Stanley R, Geiger H, Mabry TJ. C-13 NMR-Studies of flavonoids 3. Naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron 1978; 34: 1389-1397
    CrossrefPubMedGoogle Scholar
  • 17 Nasr C, Lobstein-Guth A, Haag-Berrurier M, Anton R. Quercetin coumaroyl glucorhamnoside from Ginkgo biloba . Phytochem 1987; 26: 2869-2870
    CrossrefPubMedGoogle Scholar
  • 18 Pauli GF, Matthiesen U, Fronczek FR. Sulfates as novel steroid metabolites in higher plants. Phytochem 1999; 52: 1075-1084
    CrossrefPubMedGoogle Scholar
  • 19 Sikorska M, Matlawska I. Kaempferol, isorhamnetin and their glycosides in the flowers of Asclepias syriaca L. Acta Pol Pharm 2001; 58: 269-272
    PubMedGoogle Scholar
  • 20 Yoshinari K, Shimazaki N, Sashida Y, Mimaki Y. Flavanone xyloside and lignans from Prunus jamasakura Bark. Phytochem 1990; 29: 1675-1678
    CrossrefPubMedGoogle Scholar
  • 21 Kumar N, Bhandari P, Singh B, Bari SS. Antioxidant activity and ultra-performance LC-electrospray ionization-quadrupole time-of-flight mass spectrometry for phenolics-based fingerprinting of rose species: Rosa damascena, Rosa bourboniana and Rosa brunonii . Food Chem Toxicol 2009; 47: 361-367
    CrossrefPubMedGoogle Scholar
  • 22 Nowak R, Gawlik-Dziki U. Polyphenols of Rosa leaves extracts and their radical scavenging activity. Z Naturforsch C 2007; 62: 32-38
    PubMedGoogle Scholar
  • 23 Nowak R, Olech M, Pecio L, Oleszek W, Los R, Malm A, Rzymowska J. Cytotoxic, antioxidant, antimicrobial properties and chemical composition of rose petals. J Sci Food Agr 2014; 94: 560-567
    CrossrefPubMedGoogle Scholar
  • 24 Sepulveda L, Ascacio A, Rodriguez-Herrera R, Aguilera-Carbo A, Aguilar CN. Ellagic acid: Biological properties and biotechnological development for production processes. Afr J Biotechnol 2011; 10: 4518-4523
    PubMedGoogle Scholar
  • 25 Vattem DA, Shetty K. Biological functionality of ellagic acid: A review. J Food Biochem 2005; 29: 234-266
    CrossrefPubMedGoogle Scholar
  • 26 Mishra S, Vinayak M. Ellagic acid inhibits PKC signaling by improving antioxidant defense system in murine T cell lymphoma. Mol Biol Rep 2014; 41: 4187-4197
    CrossrefPubMedGoogle Scholar
  • 27 Mishra S, Vinayak M. Ellagic acid induces novel and atypical PKC isoforms and promotes caspase-3 dependent apoptosis by blocking energy metabolism. Nutr Cancer 2014; 66: 675-681
    CrossrefPubMedGoogle Scholar
  • 28 Umesalma S, Nagendraprabhu P, Sudhandiran G. Antiproliferative and apoptotic-inducing potential of ellagic acid against 1,2-dimethyl hydrazine-induced colon tumorigenesis in Wistar rats. Mol Cell Biochem 2014; 388: 157-172
    CrossrefPubMedGoogle Scholar
  • 29 Vanella L, Di Giacomo C, Acquaviva R, Barbagallo I, Li Volti G, Cardile V, Abraham NG, Sorrenti V. Effects of ellagic acid on angiogenic factors in prostate cancer cells. Cancers 2013; 5: 726-738
    CrossrefPubMedGoogle Scholar
  • 30 Singleton VL, Orthofer R, Lamuela-Raventos RM. Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteu reagent. Methods Enzymol 1999; 299: 152-178
    PubMedGoogle Scholar
  • 31 Brandwilliams W, Cuvelier ME, Berset C. Use of a free-radical method to evaluate antioxidant activity. Food Sci Technol-Leb 1995; 28: 25-30
    PubMedGoogle Scholar
  • 32 Scott TA, Melvin EH. Determination of dextran with anthrone. Anal Chem 1953; 25: 1656-1661
    CrossrefPubMedGoogle Scholar