Extraction of High Value Triterpenic Acids from Eucalyptus globulus Biomass Using Hydrophobic Deep Eutectic Solvents

被引:49
作者
Silva, Nuno H. C. S. [1 ]
Morais, Eduarda S. [1 ]
Freire, Carmen S. R. [1 ]
Freire, Mara G. [1 ]
Silvestre, Armando J. D. [1 ]
机构
[1] Univ Aveiro, Chem Dept, CICECO Aveiro Inst Mat, Campus Univ Santiago, P-3810193 Aveiro, Portugal
来源
MOLECULES | 2020年 / 25卷 / 01期
关键词
triterpenic acids; ursolic acid; Eucalyptus globulus outer bark; hydrophobic deep eutectic solvents; menthol; thymol; SUPERCRITICAL-FLUID EXTRACTION; CHOLINE CHLORIDE; URSOLIC ACID; BIOECONOMY; SELECTIVITY; ANTITUMOR; FOREST;
D O I
10.3390/molecules25010210
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Triterpenic acids (TTAs), known for their promising biological properties, can be found in different biomass sources and related by-products, such as Eucalyptus globulus bark, and have been extracted using organic volatile solvents such as dichloromethane. Recently, deep eutectic solvents (DES) have been identified as promising alternatives for the extraction of value-added compounds from biomass. In the present work, several hydrophobic DES were tested for the extraction of TTAs from E. globulus bark. Initial solubility studies revealed that DES based on menthol and thymol as the most promising solvents for these compounds given the highest solubilities obtained for ursolic acid (UA) at temperatures ranging from room temperature up to 90 degrees C. Accordingly, an eutectic mixture of menthol:thymol (1:2) was confirmed as the best candidate for the TTAs extraction from E. globulus outer bark, leading to extraction yields (weight of TTA per weight of biomass) at room temperature of 1.8 wt% for ursolic acid, 0.84 wt% for oleanolic acid and 0.30 wt% for betulinic acid. These values are significantly higher than those obtained with conventional organic solvents under similar conditions. The results obtained using these DES are promising for the recovery of TTAs for nutraceutical and pharmacological applications, while reinforcing the potential of DES as promising solvents to be applied in biorefinery processes.
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页数:11
相关论文
共 47 条
[1]   Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids [J].
Abbott, AP ;
Boothby, D ;
Capper, G ;
Davies, DL ;
Rasheed, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :9142-9147
[2]   Phenolic hydrogen bond donors in the formation of non-ionic deep eutectic solvents: the quest for type V DES [J].
Abranches, Dinis O. ;
Martins, Monia A. R. ;
Silva, Liliana P. ;
Schaeffer, Nicolas ;
Pinho, Simao P. ;
Coutinho, Joao A. P. .
CHEMICAL COMMUNICATIONS, 2019, 55 (69) :10253-10256
[3]  
Antikainen Riina., 2017, Renewal of forest based manufacturing towards a sustainable circular bioeconomy
[4]   A Review of Natural and Modified Betulinic, Ursolic and Echinocystic Acid Derivatives as Potential Antitumor and Anti-HIV Agents [J].
Baglin, I. ;
Mitaine-Offer, A. -C. ;
Nour, M. ;
Tan, K. ;
Cave, C. ;
Lacaille-Dubois, M. -A. .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2003, 3 (06) :525-539
[5]   Phytochemical Analysis of Podospermum and Scorzonera n-Hexane Extracts and the HPLC Quantitation of Triterpenes [J].
Bahadir-Acikara, Ozlem ;
Ozbilgin, Serkan ;
Saltan-Iscan, Gulcin ;
Dall'Acqua, Stefano ;
Rjaskova, Veronika ;
Ozgokce, Fevzi ;
Suchy, Vaclav ;
Smejkal, Karel .
MOLECULES, 2018, 23 (07)
[6]   Assessing the extent and the environmental drivers of Eucalyptus globulus wildling establishment in Portugal: results from a countrywide survey [J].
Catry, F. X. ;
Moreira, F. ;
Deus, E. ;
Silva, J. S. ;
Aguas, A. .
BIOLOGICAL INVASIONS, 2015, 17 (11) :3163-3181
[7]   Application of deep eutectic solvents in biomass pretreatment and conversion [J].
Chen, Yu ;
Mu, Tiancheng .
GREEN ENERGY & ENVIRONMENT, 2019, 4 (02) :95-115
[8]   Deep Eutectic Solvents as Efficient Media for the Extraction and Recovery of Cynaropicrin from Cynara cardunculus L. Leaves [J].
de Faria, Emanuelle L. P. ;
do Carmo, Rafael S. ;
Claudio, Ana Filipa M. ;
Freire, Carmen S. R. ;
Freire, Mara G. ;
Silvestre, Armando J. D. .
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2017, 18 (11)
[9]   Aqueous Solutions of Surface-Active Ionic Liquids: Remarkable Alternative Solvents To Improve the Solubility of Triterpenic Acids and Their Extraction from Biomass [J].
de Faria, Emanuelle L. P. ;
Shabudin, Selesa V. ;
Claudio, Ana Filipa M. ;
Valega, Monica ;
Domingues, Fernando M. J. ;
Freire, Carmen S. R. ;
Silvestre, Armando J. D. ;
Freire, Mara G. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (08) :7344-7351
[10]   Scale-up studies of the supercritical fluid extraction of triterpenic acids from Eucalyptus globulus bark [J].
de Melo, M. M. R. ;
Domingues, R. M. A. ;
Sova, M. ;
Lack, E. ;
Seidlitz, H. ;
Lang, F., Jr. ;
Silvestre, A. J. D. ;
Silva, C. M. .
JOURNAL OF SUPERCRITICAL FLUIDS, 2014, 95 :44-50