Rapid and Efficient Separation of Decursin and Decursinol Angelate from Angelica gigas Nakai using Ionic Liquid, (BMIm)BF4, Combined with Crystallization

Ionic liquids (ILs) have gained much attention as alternative solvents to volatile organic solvents due to their attractive properties. This study aimed to develop an efficient method for the selective separation of decursin (D) and decursinol angelate (DA) from Angelica gigas Nakai (A. gigas) using ILs and crystallization. The IL 1-butyl-3-methylimidazolium tetrafluoroborate ((BMIm)BF4) was the most efficient at extracting D and DA. Parameters including solid-to-liquid ratio, time, and temperature were optimized by response surface methodology (RSM). Under optimal extraction conditions (1 g/6.5 mL solid-to-liquid ratio, 60 °C temperature, and 120 min time), the extraction yields of D and DA were 43.32 mg/g (97.06%) and 17.87 mg/g (97.12%), respectively. Moreover, drowning out crystallization using deionized water (DW) as an anti-solvent offered an excellent ability to recover D and DA from the A. gigas–(BMIm)BF4 extraction solution. The rates of recovery and the total purity of D and DA were found to be greater than 97%. Therefore, a rapid and efficient method of combining ILs with crystallization was effectively achieved for the selective separation of D and DA. This approach is assumed to be beneficial in the pharmaceutical industry for the effective obtention of D- and DA-enriched products.

[1]  Mengxia Wei,et al.  Enrichment and Purification of Aucubin from Eucommia ulmoides Ionic Liquid Extract Using Macroporous Resins , 2018, Materials.

[2]  Liling Wang,et al.  Application of Ionic Liquid-Based Ultrasonic-Assisted Extraction of Flavonoids from Bamboo Leaves , 2018, Molecules.

[3]  Lei Yang,et al.  A novel approach for the simultaneous extraction of dihydroquercetin and arabinogalactan from Larix gmelinii by homogenate-ultrasound-synergistic technique using the ionic liquid , 2018, Journal of Molecular Liquids.

[4]  Yeon-Bok Kim,et al.  Natural Korean Medicine Dang-Gui: Biosynthesis, Effective Extraction and Formulations of Major Active Pyranocoumarins, Their Molecular Action Mechanism in Cancer, and Other Biological Activities , 2017, Molecules.

[5]  Periaswamy Sivagnanam Saravana,et al.  Recovery of carrageenan from Solomon Islands red seaweed using ionic liquid-assisted subcritical water extraction , 2017 .

[6]  Z. Tan,et al.  Extraction, Preconcentration and Isolation of Flavonoids from Apocynum venetum L. Leaves Using Ionic Liquid-Based Ultrasonic-Assisted Extraction Coupled with an Aqueous Biphasic System , 2016, Molecules.

[7]  H. Kim,et al.  Quantitative analysis of marker compounds in Angelica gigas, Angelica sinensis, and Angelica acutiloba by HPLC/DAD. , 2015, Chemical & pharmaceutical bulletin.

[8]  Y. Cho,et al.  Anti-Inflammatory Effect of Angelica gigas via Heme Oxygenase (HO)-1 Expression , 2015, Nutrients.

[9]  J. Lee,et al.  Physiochemical Characteristics of Extruded Angelica gigas Nakai Depending on the Extrusion Processing Parameter , 2014 .

[10]  Arvind Kumar,et al.  Efficient Extraction of Agarose from Red Algae Using Ionic Liquids , 2014 .

[11]  Geert-Jan Witkamp,et al.  Ionic liquids and deep eutectic solvents in natural products research: mixtures of solids as extraction solvents. , 2013, Journal of natural products.

[12]  Meiw Han,et al.  Aqueous ionic liquid based ultrasonic assisted extraction of eight ginsenosides from ginseng root. , 2013, Ultrasonics sonochemistry.

[13]  N. Xu,et al.  Aqueous ionic liquid based ultrasonic assisted extraction of four acetophenones from the Chinese medicinal plant Cynanchum bungei Decne. , 2013, Ultrasonics sonochemistry.

[14]  Kyung Ho Row,et al.  Application of ionic liquid for extraction and separation of bioactive compounds from plants. , 2012, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[15]  B. Glennon,et al.  In situ monitoring, control and optimization of a liquid–liquid phase separation crystallization , 2012 .

[16]  T. Zhu,et al.  Ultrasonic Extraction of Phenolic Compounds from Laminaria japonica Aresch Using Ionic Liquid as Extraction Solvent , 2011 .

[17]  S. K. Park,et al.  Decursin and Decursinol from Angelica gigas Inhibit the Lung Metastasis of Murine Colon Carcinoma , 2011, Phytotherapy research : PTR.

[18]  Li Li,et al.  Protective Effects of Decursin and Decursinol Angelate against Amyloid β-Protein-Induced Oxidative Stress in the PC12 Cell Line: The Role of Nrf2 and Antioxidant Enzymes , 2011, Bioscience, biotechnology, and biochemistry.

[19]  J. Rantanen,et al.  Influence of Temperature on Solvent-Mediated Anhydrate-to-Hydrate Transformation Kinetics , 2011, Pharmaceutical Research.

[20]  J. Cha,et al.  Bioactive Materials and Biological Activity in the Extracts of Leaf, Stem Mixture and Root from Angelica gigas Nakai , 2010 .

[21]  Wenyan Ma,et al.  Application of ionic liquids based microwave-assisted extraction of three alkaloids N-nornuciferine, O-nornuciferine, and nuciferine from lotus leaf. , 2010, Talanta.

[22]  백인환,et al.  신약 개발을 위한 참당귀(Angelica gigas Nakai) 추출 Decursin과 Decursinol Angelate의 약리 작용 , 2009 .

[23]  Xiaoji Cao,et al.  Ionic liquid-based ultrasonic-assisted extraction of piperine from white pepper. , 2009, Analytica chimica acta.

[24]  Jing Fan,et al.  Solvent extraction of selected endocrine-disrupting phenols using ionic liquids , 2008 .

[25]  R. Rogers,et al.  Ionic Liquids Then and Now: From Solvents to Materials to Active Pharmaceutical Ingredients , 2007 .

[26]  B. Xiao,et al.  Decursin and decursinol angelate inhibit estrogen-stimulated and estrogen-independent growth and survival of breast cancer cells , 2007, Breast Cancer Research.

[27]  J. Shim,et al.  Optimized conditions for the extraction of secondary volatile metabolites in Angelica roots by accelerated solvent extraction. , 2007, Journal of pharmaceutical and biomedical analysis.

[28]  Alexei A Lapkin,et al.  Comparative assessment of technologies for extraction of artemisinin. , 2006, Journal of natural products.

[29]  Kwang-Soo Kim,et al.  The optimization of microwave‐assisted extraction of decursin from Angelica gigas Nakai root , 2006 .

[30]  R. Sheldon,et al.  Recovery of pure products from ionic liquids using supercritical carbon dioxide as a co-solvent in extractions or as an anti-solvent in precipitations , 2006 .

[31]  J. Bolton,et al.  Serotonergic activity-guided phytochemical investigation of the roots of Angelica sinensis. , 2006, Journal of natural products.

[32]  Hua Zhao,et al.  Use of ionic liquids as ‘green’ solvents for extractions , 2005 .

[33]  Hongwei Zhang,et al.  Free Radical Polymerization of Styrene and Methyl Methacrylate in Various Room Temperature Ionic Liquids , 2005 .

[34]  S. H. Lee,et al.  HPLC analysis and extraction methods of decursin and decursinol angelate in Angelica gigas roots , 2003 .

[35]  Li Xiao,et al.  Significance of Cations in Ionic Liquids Chemistry , 2002 .

[36]  T. Schäfer,et al.  Selective recovery of solutes from ionic liquids by pervaporation--a novel approach for purification and green processing. , 2001, Chemical communications.

[37]  R. Davey,et al.  From Molecules to Crystallizers: An Introduction to Crystallization , 2000 .

[38]  K. Shin,et al.  Isolation of drug metabolism modifiers from roots of Angelica koreana. , 1982, Planta medica.