{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,18]],"date-time":"2026-04-18T00:48:59Z","timestamp":1776473339575,"version":"3.51.2"},"reference-count":39,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2019,11,25]],"date-time":"2019-11-25T00:00:00Z","timestamp":1574640000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Fundamental Research Funds for Central Non-Profit Scientific Institution","award":["1610232017010"],"award-info":[{"award-number":["1610232017010"]}]},{"DOI":"10.13039\/501100012421","name":"Agricultural Science and Technology Innovation Program","doi-asserted-by":"publisher","award":["ASTIP-TRIC05"],"award-info":[{"award-number":["ASTIP-TRIC05"]}],"id":[{"id":"10.13039\/501100012421","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Shandong Provincial Natural Science Foundation, China","award":["ZR2016BQ43, ZR2019BB061"],"award-info":[{"award-number":["ZR2016BQ43, ZR2019BB061"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>Deep eutectic solvents (DESs) were used in combination with macroporous resins to isolate and purify flavonoids and 20-hydroxyecdysone from Chenopodium quinoa Willd by preparative high-performance liquid chromatography (HPLC). The extraction performances of six DESs and the adsorption\/desorption performances of five resins (AB-8, D101, HPD 400, HPD 600, and NKA-9) were investigated using the total flavonoid and 20-hydroxyecdysone extraction yields as the evaluation criteria, and the best-performing DES (choline chloride\/urea, DES-6) and macroporous resin (D101) were further employed for phytochemical extraction and DES removal, respectively. The purified extract was subjected to preparative HPLC, and the five collected fractions were purified in a successive round of preparative HPLC to isolate three flavonoids and 20-hydroxyecdysone, which were identified by spectroscopic techniques. The use of a DES in this study significantly facilitated the preparative-scale isolation and purification of polar phytochemicals from complex plant systems.<\/jats:p>","DOI":"10.3390\/biom9120776","type":"journal-article","created":{"date-parts":[[2019,11,25]],"date-time":"2019-11-25T11:12:21Z","timestamp":1574680341000},"page":"776","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Combined Use of Deep Eutectic Solvents, Macroporous Resins, and Preparative Liquid Chromatography for the Isolation and Purification of Flavonoids and 20-Hydroxyecdysone from Chenopodium quinoa Willd"],"prefix":"10.3390","volume":"9","author":[{"given":"Jia","family":"Zeng","sequence":"first","affiliation":[{"name":"Tobacco Research Institute, Chinese Academy of Agricultural Sciences, Qingdao 266101, China"},{"name":"Graduate School of Chinese Academy of Agricultural Sciences, Beijing 100081, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xianchao","family":"Shang","sequence":"additional","affiliation":[{"name":"Tobacco Research Institute, Chinese Academy of Agricultural Sciences, Qingdao 266101, China"},{"name":"Graduate School of Chinese Academy of Agricultural Sciences, Beijing 100081, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Peng","family":"Zhang","sequence":"additional","affiliation":[{"name":"Tobacco Research Institute, Chinese Academy of Agricultural Sciences, Qingdao 266101, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2139-8439","authenticated-orcid":false,"given":"Hongwei","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory Cultivation Base, Shandong Provincial Key Laboratory of Ophthalmology, Shandong Eye Institute, Shandong First Medical University &amp; Shandong Academy of Medical Sciences, Qingdao 266071, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yanlong","family":"Gu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3802-8426","authenticated-orcid":false,"given":"Jia-Neng","family":"Tan","sequence":"additional","affiliation":[{"name":"Tobacco Research Institute, Chinese Academy of Agricultural Sciences, Qingdao 266101, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,11,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"11060","DOI":"10.1021\/cr300162p","article-title":"Deep eutectic solvents (DESs) and their applications","volume":"114","author":"Smith","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1021\/acs.chemrev.7b00571","article-title":"Green and sustainable solvents in chemical processes","volume":"118","author":"Clarke","year":"2018","journal-title":"Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"8685","DOI":"10.1039\/C8CS00325D","article-title":"The peculiar effect of water on ionic liquids and deep eutectic solvents","volume":"47","author":"Ma","year":"2018","journal-title":"Chem. Soc. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2020","DOI":"10.1039\/C7CS00464H","article-title":"Ionic liquids and derived materials for lithium and sodium batteries","volume":"47","author":"Yang","year":"2018","journal-title":"Chem. Soc. Rev."},{"key":"ref_5","first-page":"1007","article-title":"Glycerol based solvents: synthesis, properties and applications","volume":"16","author":"Pires","year":"2013","journal-title":"Green Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2969","DOI":"10.1039\/c2gc36005e","article-title":"Low melting mixtures in organic synthesis \u2013 an alternative to ionic liquids?","volume":"14","author":"Carolin","year":"2012","journal-title":"Green Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2746","DOI":"10.1021\/acssuschemeng.5b00619","article-title":"Biocompatible deep eutectic solvents based on choline chloride: Characterization and application to the extraction of rutin from sophora japonica","volume":"3","author":"Zhao","year":"2015","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2061","DOI":"10.1039\/C8GC04000A","article-title":"Utilization of bio-based glycolaldehyde aqueous solution in organic synthesis: application to the synthesis of 2,3-dihydrofurans","volume":"21","author":"Xu","year":"2019","journal-title":"Green Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2169","DOI":"10.1021\/acssuschemeng.8b04877","article-title":"Natural Deep Eutectic Solvent-Catalyzed Selenocyanation of Activated Alkynes via an Intermolecular H-Bonding Activation Process","volume":"7","author":"Wu","year":"2019","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"8798","DOI":"10.1021\/acssuschemeng.9b00708","article-title":"Practical Approach for Clean Preparation of Z-\u03b2-Thiocyanate Alkenyl Esters","volume":"7","author":"Wu","year":"2019","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1237","DOI":"10.1016\/j.cclet.2019.04.033","article-title":"Sustainable routes for quantitative green selenocyanation of activated alkynes","volume":"30","author":"Lu","year":"2019","journal-title":"Chin. Chem. Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4169","DOI":"10.1039\/C8GC01120F","article-title":"Ionic liquids for the preparation of biopolymer materials for drug\/gene delivery: a review","volume":"20","author":"Chen","year":"2018","journal-title":"Green Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1002\/adma.200900603","article-title":"Preparation of inorganic materials using ionic liquids","volume":"22","author":"Ma","year":"2010","journal-title":"Adv. Mater."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1016\/j.trac.2018.05.001","article-title":"Extraction techniques with deep eutectic solvents","volume":"105","author":"Cunha","year":"2018","journal-title":"Trends Anal. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2405","DOI":"10.1021\/acssuschemeng.6b00091","article-title":"Comprehensive evaluation of deep eutectic solvents in extraction of bioactive natural products","volume":"4","author":"Duan","year":"2016","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"50","DOI":"10.1016\/j.chroma.2016.01.037","article-title":"Application of natural deep eutectic solvents to the extraction of anthocyanins from Catharanthus roseus with high extractability and stability replacing conventional organic solvents","volume":"1434","author":"Dai","year":"2016","journal-title":"J. Chromatogr. A"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2933","DOI":"10.1021\/acssuschemeng.8b03520","article-title":"A Search for natural hydrophobic deep eutectic solvents based on natural components","volume":"7","author":"Dietz","year":"2019","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1718","DOI":"10.1039\/C4GC01556H","article-title":"Enhanced extraction of bioactive natural products using tailor-made deep eutectic solvents: application to flavonoid extraction from Flos sophorae","volume":"17","author":"Nam","year":"2015","journal-title":"Green Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"679","DOI":"10.1021\/acs.jnatprod.7b00945","article-title":"Natural deep eutectic solvents: properties, applications, and perspectives","volume":"81","author":"Liu","year":"2018","journal-title":"J. Nat. Prod."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1016\/j.foodchem.2018.12.068","article-title":"Chemical and nutritional characterization of Chenopodium quinoa Willd. (quinoa) grains: A good alternative to nutritious food","volume":"280","author":"Pereira","year":"2019","journal-title":"Food Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"592","DOI":"10.1016\/j.foodchem.2019.02.016","article-title":"Metabolic fingerprinting unveils quinoa oil as a source of bioactive phytochemicals","volume":"286","author":"Chen","year":"2019","journal-title":"Food Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1016\/0308-8146(93)90048-K","article-title":"Saponins, phytic acid, tannins and protease inhibitors in quinoa (Chenopodium quinoa Willd.) seeds","volume":"48","author":"Ruales","year":"1993","journal-title":"Food Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1919","DOI":"10.1016\/j.phytochem.2008.03.001","article-title":"Triterpene saponins from Chenopodium quinoa Willd","volume":"69","author":"Kuljanabhagavad","year":"2008","journal-title":"Phytochemistry"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"865","DOI":"10.1021\/jf011002l","article-title":"Triterpene saponins from debittered quinoa","volume":"50","author":"Zhu","year":"2002","journal-title":"J. Agric. Food Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1016\/j.foodchem.2017.04.187","article-title":"Characterization of betalains, saponins and antioxidant power in differently colored quinoa (Chenopodium quinoa) varieties","volume":"234","author":"Escribano","year":"2017","journal-title":"Food Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"4620","DOI":"10.1021\/jf3002125","article-title":"Phenolic compounds and saponins in quinoa samples (Chenopodium quinoa Willd.) grown under different saline and nonsaline irrigation regimens","volume":"60","author":"Iafelice","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"502","DOI":"10.1016\/j.foodchem.2014.11.040","article-title":"Characterisation of fatty acid, carotenoid, tocopherol\/tocotrienol compositions and antioxidant activities in seeds of three Chenopodium quinoa Willd. genotypes","volume":"174","author":"Tang","year":"2015","journal-title":"Food Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1002\/jsfa.7134","article-title":"Phytoecdysteroids and flavonoid glycosides among Chilean and commercial sources of Chenopodium quinoa: variation and correlation to physico-chemical characteristics","volume":"96","author":"Graf","year":"2016","journal-title":"J. Sci. Food Agric."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1016\/S0308-8146(03)00185-7","article-title":"Phenolic constituents of Kancolla seeds","volume":"84","author":"Dini","year":"2004","journal-title":"Food Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1226","DOI":"10.1016\/j.foodchem.2010.10.039","article-title":"Ecdysteroids from Chenopodium quinoa Willd., an ancient Andean crop of high nutritional value","volume":"125","author":"Kumpun","year":"2011","journal-title":"Food Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.foodchem.2014.11.043","article-title":"Protein content and amino acids profile of pseudocereals","volume":"193","author":"Mota","year":"2016","journal-title":"Food Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1016\/j.foodchem.2014.04.088","article-title":"Quinoa seeds leach phytoecdysteroids and other compounds with anti-diabetic properties","volume":"163","author":"Graf","year":"2014","journal-title":"Food Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/j.foodchem.2019.02.061","article-title":"Quinoa intake reduces plasma and liver cholesterol, lessens obesity-associated inflammation, and helps to prevent hepatic steatosis in obese db\/db mouse","volume":"287","author":"Noratto","year":"2019","journal-title":"Food Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1944","DOI":"10.1039\/C7FO01792H","article-title":"Effects of superfoods on risk factors of metabolic syndrome: a systematic review of human intervention trials","volume":"9","author":"Plat","year":"2018","journal-title":"Food Funct."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1016\/j.indcrop.2018.12.041","article-title":"Phytochemical and biological activities of Silene viridiflora extractives. Development and validation of a HPTLC method for quantification of 20-hydroxyecdysone","volume":"129","author":"Mamadalieva","year":"2019","journal-title":"Ind. Crop. Prod."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"386","DOI":"10.3109\/13880209.2014.922589","article-title":"Coffee silverskin: a possible valuable cosmetic ingredient","volume":"53","author":"Rodrigues","year":"2015","journal-title":"Pharm. Biol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.chroma.2018.11.019","article-title":"Porous organic cage incorporated monoliths for solid-phase extraction coupled with liquid chromatography-mass spectrometry for identification of ecdysteroids from Chenopodium quinoa Willd","volume":"1583","author":"Wang","year":"2019","journal-title":"J. Chromatogr. A"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1016\/S0308-8146(97)00037-X","article-title":"Survey of enzyme activities in desaponified quinoa Chenopodium quinoa Willd","volume":"60","author":"Caussette","year":"1997","journal-title":"Food Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"447","DOI":"10.1016\/j.lwt.2009.09.010","article-title":"Antioxidant compound contents and antioxidant activity before and after cooking in sweet and bitter Chenopodium quinoa seeds","volume":"43","author":"Dini","year":"2010","journal-title":"LWT-Food Sci. Technol."}],"container-title":["Biomolecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2218-273X\/9\/12\/776\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:37:25Z","timestamp":1760189845000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2218-273X\/9\/12\/776"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,11,25]]},"references-count":39,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2019,12]]}},"alternative-id":["biom9120776"],"URL":"https:\/\/doi.org\/10.3390\/biom9120776","relation":{},"ISSN":["2218-273X"],"issn-type":[{"value":"2218-273X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,11,25]]}}}