{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T21:01:45Z","timestamp":1788382905720,"version":"build-2803163510"},"reference-count":32,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2022,11,11]],"date-time":"2022-11-11T00:00:00Z","timestamp":1668124800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"The National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["81372404"],"award-info":[{"award-number":["81372404"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"The National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["KJ21125110"],"award-info":[{"award-number":["KJ21125110"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"The Fund of Jiangsu Market Supervision and Administration Bureau in 2021","award":["81372404"],"award-info":[{"award-number":["81372404"]}]},{"name":"The Fund of Jiangsu Market Supervision and Administration Bureau in 2021","award":["KJ21125110"],"award-info":[{"award-number":["KJ21125110"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Ginkgols are active constituents from Ginkgo biloba L. (GB) and have pharmacological activities, such as antibacterial and antioxidant activities. In our previous report, only five ginkgols were separated. However, ginkgol C17:1 had two isomers, for which their separation, identification, and bioactivities have not yet been investigated. Hence, this research reports the successful isolation of six ginkgol homologs with alkyl substituents\u2014C17:1-\u039412, C15:1-\u03948, C13:0, C17:2, C17:1-\u039410, and C15:0\u2014for the first time using HPLC. This was followed by the identification of their chemical structures using Fourier transform infrared (FTIR), ultraviolet (UV), gas chromatography and mass spectrometry (GC-MS), carbon-13 nuclear magnetic resonance (13C-NMR), and proton nuclear magnetic resonance (1H-NMR) analysis. The results showed that two ginkgol isomers, C17:1-\u039412 and C17:1-\u039410, were obtained simultaneously from the ginkgol C17:1 mixture and identified entirely for the first time. That aside, the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) assay showed that the six ginkgol homologs possessed significant antiproliferation effects against HGC and HepG2 cells. Furthermore, the ginkgols with unsaturated side chains (C17:2, C15:1-\u03948, C17:1-\u039412, and C17:1-\u039410) exhibited more potent inhibitory effects than ginkgols with saturated side chains (C13:0, C15:0). In addition, unsaturated ginkgol C15:1-\u03948 showed the most potent cytotoxicity on HepG2 and HGC cells, of which the half-maximal inhibition concentrations (IC50) were 18.84 \u00b1 2.58 and 13.15 \u00b1 2.91 \u03bcM, respectively. The IC50 for HepG2 and HGC cells for the three unsaturated ginkgols (C17:1-\u039410, C17:2 and C17:1-\u039412) were ~59.97, ~60.82, and ~68.97 \u03bcM for HepG2 and ~30.97, ~33.81, and ~34.55 \u03bcM for HGC cells, respectively. Comparing the ginkgols\u2019 structure\u2013activity relations, the findings revealed that the position and number of the double bonds of the ginkgols with 17 side chain carbons in length had no significant difference in anticancer activity.<\/jats:p>","DOI":"10.3390\/molecules27227777","type":"journal-article","created":{"date-parts":[[2022,11,14]],"date-time":"2022-11-14T04:24:10Z","timestamp":1668399850000},"page":"7777","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Extraction, Purification, and Elucidation of Six Ginkgol Homologs from Ginkgo biloba Sarcotesta and Evaluation of Their Anticancer Activities"],"prefix":"10.3390","volume":"27","author":[{"given":"Fengnan","family":"Li","sequence":"first","affiliation":[{"name":"School of Food and Biological Engineering, Jiangsu University, Zhenjiang 212013, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0900-3027","authenticated-orcid":false,"given":"Isaac Duah","family":"Boateng","sequence":"additional","affiliation":[{"name":"Food Science Program, Division of Food, Nutrition and Exercise Sciences, University of Missouri, 1406 E Rollins Street, Columbia, MO 65211, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoming","family":"Yang","sequence":"additional","affiliation":[{"name":"School of Food and Biological Engineering, Jiangsu University, Zhenjiang 212013, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuanyuan","family":"Li","sequence":"additional","affiliation":[{"name":"Zhenjiang Food and Drug Supervision and Inspection Center, Zhenjiang 212004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"9226","DOI":"10.1039\/D2FO01827F","article-title":"A critical review of ginkgolic acids in Ginkgo biloba leaf extract (EGb): Toxicity and technologies to remove ginkgolic acids and their promising bioactivities","volume":"13","author":"Boateng","year":"2022","journal-title":"Food Funct."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"132408","DOI":"10.1016\/j.foodchem.2022.132408","article-title":"A critical review of current technologies used to reduce ginkgotoxin, ginkgotoxin-5\u2032-glucoside, ginkgolic acid, allergic glycoprotein, and cyanide in Ginkgo biloba L. seed","volume":"382","author":"Boateng","year":"2022","journal-title":"Food Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"114281","DOI":"10.1016\/j.indcrop.2021.114281","article-title":"Ginkgo biloba L. seed; A comprehensive review of bioactives, toxicants, and processing effects","volume":"176","author":"Boateng","year":"2022","journal-title":"Ind. 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