One-step isolation of carnosic acid and carnosol from rosemary by centrifugal partition chromatography.

Carnosic acid and carnosol are the main bioactive components responsible for the significant antioxidant activity of Rosmarinus officinalis. Nevertheless, they are known for their instability in solutions. Separation of both compounds from crude rosemary extract was successfully achieved by one-step centrifugal partition chromatography without any degradation. A two-phase solvent system, hexane/ethyl acetate/methanol/water (3:2:3:2 v/v) was run on a preparative scale applying the elution-extrusion technique in descending mode. A 900 mg quantity of the crude extract containing 39.7% carnosic acid and 12.3% carnosol was loaded onto a 500 mL column, rotating at 1800 rpm. Carnosic acid and carnosol were obtained at purities of 96.1 ± 1% and 94.4 ± 0.9%, with recoveries of 94.3 ± 4.4% and 94.8 ± 2.3%, respectively. The compounds were identified by mass spectrometry, tandem mass spectrometry, and comparison with authentic standards.

[1]  K. Faure,et al.  Carnosol purification. Scaling-up centrifugal partition chromatography separations. , 2016, Journal of chromatography. A.

[2]  Hong Xu,et al.  Degradation pathway of carnosic acid in methanol solution through isolation and structural identification of its degradation products , 2013, European Food Research and Technology.

[3]  D. Armstrong,et al.  Degradation study of carnosic acid, carnosol, rosmarinic acid, and rosemary extract (Rosmarinus officinalis L.) assessed using HPLC. , 2012, Journal of agricultural and food chemistry.

[4]  M. Lila,et al.  Isolation and characterization of flavonols from blackcurrant by high-performance counter-current chromatography and electrospray ionization tandem mass spectrometry. , 2012, Journal of separation science.

[5]  Peter J. Smith,et al.  In vitro antiplasmodial activity of indole alkaloids from the stem bark of Geissospermum vellosii. , 2012, Journal of Ethnopharmacology.

[6]  Peter J. Smith,et al.  Isolation and identification of antiplasmodial N-alkylamides from Spilanthes acmella flowers using centrifugal partition chromatography and ESI-IT-TOF-MS. , 2011, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[7]  J. Johnson.  Carnosol: a promising anti-cancer and anti-inflammatory agent. , 2011, Cancer letters.

[8]  C. Peng,et al.  Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from Rosmarinus officinalis leaves. , 2011, Journal of agricultural and food chemistry.

[9]  K. Yoon,et al.  Application of centrifugal partition chromatography coupled with evaporative light scattering detection for the isolation of saikosaponins-a and -c from Bupleurum falcatum roots. , 2009, Journal of Separation Science.

[10]  I. Sutherland,et al.  Rapid linear scale-up of a protein separation by centrifugal partition chromatography. , 2008, Journal of chromatography. A.

[11]  Taichi Inui,et al.  Elution-extrusion countercurrent chromatography: theory and concepts in metabolic analysis. , 2007, Analytical chemistry.

[12]  L. Janaway,et al.  Minimising Solvent Usage in High Speed, High Loading, and High Resolution Isocratic Dynamic Extraction , 2007 .

[13]  A Marston,et al.  Developments in the application of counter-current chromatography to plant analysis. , 2006, Journal of chromatography. A.

[14]  M. Ahn,et al.  A preparative isolation and purification of arctigenin and matairesinol from Forsythia koreana by centrifugal partition chromatography. , 2006, Journal of separation science.

[15]  Selma C. Etter.  Rosmarinus officinalis as an Antioxidant , 2005 .

[16]  Yoichiro Ito,et al.  Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. , 2005, Journal of chromatography. A.

[17]  T. Yokoi,et al.  Carnosic acid, a component of rosemary (Rosmarinus officinalis L.), promotes synthesis of nerve growth factor in T98G human glioblastoma cells. , 2003, Biological & pharmaceutical bulletin.

[18]  Maria Jose Ruiz-Angel,et al.  Elution-extrusion countercurrent chromatography. Use of the liquid nature of the stationary phase to extend the hydrophobicity window. , 2003, Analytical chemistry.

[19]  V. Calabrese,et al.  Biochemical studies of a natural antioxidant isolated from rosemary and its application in cosmetic dermatology. , 2000, International journal of tissue reactions.

[20]  B. Halliwell,et al.  An evaluation of the antioxidant and antiviral action of extracts of rosemary and Provençal herbs. , 1996, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[21]  N. Okamura,et al.  High-performance liquid chromatographic determination of carnosic acid and carnosol in Rosmarinus officinalis and Salvia officinalis , 1994 .

[22]  W. Ternes,et al.  Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis. III. Stability of phenolic diterpenes of rosemary extracts under thermal stress as required for technological processes. , 1992, Zeitschrift fur Lebensmittel-Untersuchung und -Forschung.

[23]  W. O. Lundberg,et al.  THE ANTIOXIDANT PROPERTIES OF NATURAL SPICESa,b , 1952 .