{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T10:29:57Z","timestamp":1790418597164,"version":"4.1.0"},"reference-count":39,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2018,7,2]],"date-time":"2018-07-02T00:00:00Z","timestamp":1530489600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"The Fundamental Research Funds for the Central Universities","award":["BLX2013025"],"award-info":[{"award-number":["BLX2013025"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The Rhodiola species have a long history of utilization in traditional medicine and have been considered as a source of adaptation to environmental challenges; salidroside and p-tyrosol are the major responsible compounds. Here we propose a novel UPLC-guided two-step method consisting of a DIAION HP-20 adsorption and silica gel column chromatographies, which can simultaneously prepare high purities of salidroside and p-tyrosol with noticeable yields from the rhizome of Rhodiola crenulata. Results demonstrated that DIAION HP-20 could successfully remove all impurities except crenulatin during a gradient elution with 5\u201320% ethanol, which could achieve an optimal purification of salidroside and p-tyrosol with increasing rates of 29.19% and 33.44%, respectively. Furthermore, chloroform was selected as an ideal solvent for separating p-tyrosol with salidroside, and thus crenulatin was subsequently applied in the silica gel chromatography, and the separation of salidroside with crenulatin could be achieved using silica gel chromatography with a mixture of chloroform and methanol at a volume ratio of 4:1. High purity rates of 94.17% and 97.29% and overall yields of 39.09% and 43.73% for salidroside and p-tyrosol were simultaneously achieved. Our method provides a new way to simultaneously obtain salidroside and p-tyrosol from R. Crenulata, as well as other related plant species.<\/jats:p>","DOI":"10.3390\/molecules23071602","type":"journal-article","created":{"date-parts":[[2018,7,2]],"date-time":"2018-07-02T10:56:52Z","timestamp":1530529012000},"page":"1602","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Simultaneous Preparation of Salidroside and p-Tyrosol from Rhodiola crenulata by DIAION HP-20 Macroporous Resin Chromatography Combined with Silica Gel Chromatography"],"prefix":"10.3390","volume":"23","author":[{"given":"Liwei","family":"Sun","sequence":"first","affiliation":[{"name":"National Engineering Laboratory for Tree Breeding, College of Biological Sciences and Biotechnology, Beijing Forestry University, Beijing 100083, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ran","family":"Zhou","sequence":"additional","affiliation":[{"name":"School of Nature Conservation, Beijing Forestry University, Beijing 100083, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinling","family":"Sui","sequence":"additional","affiliation":[{"name":"School of Nature Conservation, Beijing Forestry University, Beijing 100083, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6588-3359","authenticated-orcid":false,"given":"Yujun","family":"Liu","sequence":"additional","affiliation":[{"name":"National Engineering Laboratory for Tree Breeding, College of Biological Sciences and Biotechnology, Beijing Forestry University, Beijing 100083, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,7,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1016\/j.phymed.2010.02.002","article-title":"Rosenroot (Rhodiola rosea): Traditional use, chemical composition, pharmacology and clinical efficacy","volume":"17","author":"Panossiana","year":"2010","journal-title":"Phytomedicine"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"359","DOI":"10.1016\/j.jfda.2015.04.007","article-title":"Rhodiola plants: Chemistry and biological activity","volume":"23","author":"Chiang","year":"2015","journal-title":"J. Food Drug Anal."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1016\/j.lfs.2012.06.026","article-title":"Salidroside and tyrosol from Rhodiola protect H9c2 cells from ischemia\/reperfusion-induced apoptosis","volume":"91","author":"Sun","year":"2012","journal-title":"Life Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"770","DOI":"10.1016\/j.phymed.2016.02.009","article-title":"Rhodiola rosea L. as a putative botanical antidepressant","volume":"23","author":"Amsterdam","year":"2016","journal-title":"Phytomedicine"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"496","DOI":"10.1016\/j.biopha.2016.12.132","article-title":"Golden root: A wholesome treat of immunity","volume":"87","author":"Khanna","year":"2017","journal-title":"Biomed. Pharm."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"353","DOI":"10.3892\/etm.2015.2882","article-title":"Schisandra chinensis and Rhodiola rosea exert an anti-stress effect on the HPA axis and reduce hypothalamic c-Fos expression in rats subjected to repeated stress","volume":"11","author":"Xia","year":"2016","journal-title":"Exp. Ther. Med."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1016\/j.sjbs.2014.04.001","article-title":"Hepatoprotective effect of Rhodiola imbricata rhizome against paracetamol-induced liver toxicity in rats","volume":"21","author":"Senthilkumar","year":"2014","journal-title":"Saudi J. Biol. Sci."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1016\/S0895-3988(09)60062-3","article-title":"Pretreatment with Rhodiola rosea extract reduces cognitive impairment induced by intracerebroventricular streptozotocin in rats: Implication of anti-oxidative and neuroprotective effects","volume":"22","author":"Qu","year":"2009","journal-title":"Biomed. Environ. Sci."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"586","DOI":"10.1016\/j.jep.2016.10.011","article-title":"Beneficial effect of commercial Rhodiola extract in rats with scopolamine-induced memory impairment on active avoidance","volume":"193","author":"Vasileva","year":"2016","journal-title":"J. Ethnopharmacol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1089\/rej.2007.0560","article-title":"Rhodiola: A promising anti-aging Chinese herb","volume":"10","author":"Jafari","year":"2007","journal-title":"Rejuvenat. Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"807","DOI":"10.1248\/cpb.56.807","article-title":"Identification and Comparative Determination of Rhodionin in Traditional Tibetan Medicinal Plants of Fourteen Rhodiola Species by High-Performance Liquid Chromatography-Photodiode Array Detection and Electrospray Ionization-Mass Spectrometry","volume":"56","author":"Li","year":"2008","journal-title":"Chem. Pharm. Bull."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/j.bbrc.2010.06.033","article-title":"Salidroside induces cell-cycle arrest and apoptosis in human breast cancer cells","volume":"398","author":"Hu","year":"2010","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.jprot.2015.09.028","article-title":"SILAC-based proteomic analysis reveals that salidroside antagonizes cobalt chloride-induced hypoxic effects by restoring the tricarboxylic acid cycle in cardiomyocytes","volume":"130","author":"Xu","year":"2016","journal-title":"J. Proteom."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"723","DOI":"10.1016\/j.mad.2010.10.003","article-title":"Salidroside protects human fibroblast cells from premature senescence induced by H2O2 partly through modulating oxidative status","volume":"131","author":"Mao","year":"2010","journal-title":"Mech. Ageing Dev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1016\/S0895-3988(10)60047-5","article-title":"Protective role of salidroside against aging in a mouse model induced by D-galactose","volume":"23","author":"Mao","year":"2010","journal-title":"Biomed. Environ. Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1002\/ptr.3236","article-title":"Rhodiola-induced inhibition of adipogenesis involves antioxidant enzyme response associated with pentose phosphate pathway","volume":"25","author":"Lee","year":"2011","journal-title":"Phytother. Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"6733","DOI":"10.1021\/jf801473v","article-title":"White wine induced cardioprotection against ischemia-reperfusion injury is mediated by life extendingAkt\/FOXO3a\/NFkappaB survival pathway","volume":"56","author":"Thirunavukkarasu","year":"2008","journal-title":"J. Agric. Food Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2905","DOI":"10.1039\/C7FO00641A","article-title":"Tyrosol and its metabolites as antioxidative and anti-inflammatory molecules in human endothelial cells","volume":"8","author":"Muriana","year":"2017","journal-title":"Food Funct."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1248\/bpb.b16-00756","article-title":"Protective Effects of Tyrosol against LPS-Induced Acute Lung Injury via Inhibiting NF-\u03baB and AP-1 Activation and Activating the HO-1\/Nrf2 Pathways","volume":"40","author":"Wang","year":"2017","journal-title":"Biol. Pharm. Bull."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3758","DOI":"10.3390\/molecules20033758","article-title":"Tyrosol prevent ischemia\/reperfusion-induced cardiac injury in H9c2 cells: Involvement of ROS, Hsp70, JNK and ERK, and apoptosis","volume":"20","author":"Sun","year":"2015","journal-title":"Molecules"},{"key":"ref_21","unstructured":"Chinese Pharmacopoeia Commission (2005). Pharmacopoeia of People\u2019s Republic of China, People\u2019s Medical Publishing House."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1248\/cpb.c15-00558","article-title":"Quantitative Analysis of Salidroside and p-Tyrosol in the Traditional Tibetan Medicine Rhodiola crenulata by Fourier Transform Near-Infrared Spectroscopy","volume":"64","author":"Li","year":"2016","journal-title":"Chem. Pharm. Bull. (Tokyo)"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3143","DOI":"10.1016\/j.procbio.2005.03.043","article-title":"Enzymic synthesis of salidroside: Purification and characterization of salidrosidase from Aspergillas niger","volume":"40","author":"Zhang","year":"2005","journal-title":"Process Biochem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1007\/s11240-013-0325-z","article-title":"Production of salidroside and tyrosol in cell suspension cultures of Rhodiola crenulata","volume":"114","author":"Shi","year":"2013","journal-title":"Plant Cell Tissue Organ Cult."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1016\/S0021-9673(02)01041-5","article-title":"Separation of salidroside from Rhodiola crenulata by high-speed counter-current chromatography","volume":"971","author":"Han","year":"2002","journal-title":"J. Chromatogr. A"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.seppur.2007.07.046","article-title":"Adsorption and desorption properties of macroreticular resins for salidroside from Rhodiola sachalinensis A. Bor","volume":"61","author":"Fan","year":"2008","journal-title":"Sep. Purif. Technol."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1002\/jssc.200800438","article-title":"Preparative purification of salidroside from Rhodiola rosea by two-step adsorption chromatography on resins","volume":"32","author":"Ma","year":"2009","journal-title":"J. Sep. Sci."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1002\/pca.1262","article-title":"Metabolic Profiling of Rhodiola rosea Rhizomes by H-1 NMR Spectroscopy","volume":"22","author":"Ioset","year":"2010","journal-title":"Phytochem. Anal."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"900","DOI":"10.1016\/j.foodchem.2015.08.070","article-title":"Adsorption and desorption characteristics of adlay bran free phenolics on macroporous resins","volume":"194","author":"Yang","year":"2016","journal-title":"Food Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1016\/j.fbp.2013.12.006","article-title":"Adsorption and desorption properties of macroporous resins for flavonoids from the extract of Chinese wolfberry (Lycium barbarum L.)","volume":"93","author":"Wu","year":"2015","journal-title":"Food Bioprod. Process."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1016\/j.jchromb.2016.11.023","article-title":"Adsorption characteristics of adsorbent resins and antioxidant capacity for enrichment of phenolics from two-phase olive waste","volume":"1040","author":"Wang","year":"2017","journal-title":"J. Chromatogr. B. Anal. Technol. Biomed. Life Sci."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2003","DOI":"10.1016\/S0045-6535(98)00413-5","article-title":"Adsorption of naphthalene derivatives on hypercrosslinked polymeric adsorbents","volume":"38","author":"Xu","year":"1999","journal-title":"Chemosphere"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"6998","DOI":"10.1021\/jf034496q","article-title":"Adsorption of flavonoids on resins: Hesperidin","volume":"51","author":"Scordino","year":"2003","journal-title":"J. Agric. Food Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"338","DOI":"10.1016\/j.foodchem.2015.05.105","article-title":"Macroporous resin purification of peptides with umami taste from soy sauce","volume":"190","author":"Zhuang","year":"2016","journal-title":"Food Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1002\/jms.3764","article-title":"Characterization of chemical constituents in Rhodiola crenulata by high-performance liquid chromatography coupled with Fourier-transform ion cyclotron resonance mass spectrometer (HPLC-FT-ICR MS)","volume":"51","author":"Han","year":"2016","journal-title":"J. Mass Spectrom."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1016\/S0021-9673(04)01409-8","article-title":"Extraction and analysis of phenolics in food","volume":"1054","author":"Naczk","year":"2004","journal-title":"J. Chromatogr. A"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1523","DOI":"10.1016\/j.jpba.2006.04.002","article-title":"Phenolics in cereals, fruits and vegetables: Occurrence, extraction and analysis","volume":"41","author":"Naczk","year":"2006","journal-title":"J. Pharm. Biomed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1016\/j.jaap.2017.01.004","article-title":"Separation of chemical groups from bio-oil water-extract via sequential organic solvent extraction","volume":"123","author":"Ren","year":"2017","journal-title":"J. Anal. Appl. Pyrolysis"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1016\/S0021-9673(01)01232-8","article-title":"Preparative isolation and purification of salidroside from the Chinese medicinal plant Rhodiola sachalinensis by high-speed counter-current chromatography","volume":"932","author":"Li","year":"2001","journal-title":"J. Chromatogr. A"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/7\/1602\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:10:59Z","timestamp":1760195459000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/7\/1602"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,7,2]]},"references-count":39,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2018,7]]}},"alternative-id":["molecules23071602"],"URL":"https:\/\/doi.org\/10.3390\/molecules23071602","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,7,2]]}}}