{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T21:02:17Z","timestamp":1790542937140,"version":"4.1.0"},"reference-count":33,"publisher":"American Chemical Society (ACS)","issue":"8","license":[{"start":{"date-parts":[[2020,2,20]],"date-time":"2020-02-20T00:00:00Z","timestamp":1582156800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100003725","name":"National Research Foundation of Korea","doi-asserted-by":"publisher","award":["2017M2A2A6A05018541"],"award-info":[{"award-number":["2017M2A2A6A05018541"]}],"id":[{"id":"10.13039\/501100003725","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,3,3]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The scaly bulbs of Lilium longiflorum (Liliaceae) are used as a food ingredient and a traditional medicine in East Asia. A preliminary study revealed that treatment with 100 \u03bcg\/mL of the ethyl acetate fraction of this plant material inhibited dipeptidyl peptidase IV (DPP-IV) to 58.99%. Phytochemical studies were conducted to identify the active ingredient, and five compounds, namely, 1 (2.9 mg, 75.8% purity at 320 nm), 2 (12.2 mg, 97.9% purity at 320 nm), 3 (3.1 mg, 66.5% purity at 320 nm), 4 (6.8 mg, 96.9% purity at 320 nm), and 5 (6.2 mg, 90.2% purity at 320 nm) were purified from 200 mg of the ethyl acetate fraction of L. longiflorum via centrifugal partition chromatography (CPC) with a two-phase solvent system composed of chloroform\/methanol\/isopropanol\/water (5:2:2:4, v\/v\/v\/v) in an ascending mode. Their structures were identified as 1-O-p-coumaroyl-2-O-\u03b2-glucopyranosylglycerol (regaloside D, 1), 3,6\u2032-O-diferuloylsucrose (2), 1-O-p-coumaroyl-2-O-\u03b2-glucopyranosyl-3-O-acetylglycerol (regaloside B, 3), 1-O-p-coumaroylglycerol (4), and 4-O-acetyl-3,6\u2032-O-diferuloylsucrose (5), respectively, by 1H and 13C NMR and MS analysis. Compounds 2 and 5 exhibited DPP-IV inhibitory activities with IC50 values of 46.19 and 63.26 \u03bcM, respectively. Compounds 1, 3, and 4 did not show activities, indicating that biphenylpropanoids linked via the sugar moiety are more effective than phenylpropanoids with glycerol or glyceryl glucoside. This is the first report of simultaneous separation of five phenylpropanoids from L. longiflorum by CPC and evaluation of their DPP-IV inhibitory activities.<\/jats:p>","DOI":"10.1021\/acsomega.9b03649","type":"journal-article","created":{"date-parts":[[2020,2,20]],"date-time":"2020-02-20T11:41:01Z","timestamp":1582198861000},"page":"4050-4057","source":"Crossref","is-referenced-by-count":18,"title":["Purification of Phenylpropanoids from the Scaly Bulbs\nof\n                    <i>Lilium Longiflorum<\/i>\n                    by CPC and Determination of Their DPP-IV Inhibitory\nPotentials"],"prefix":"10.1021","volume":"5","author":[{"given":"Bo-Ram","family":"Kim","sequence":"first","affiliation":[{"name":"Korea Atomic Energy Research Institute , , , ,","place":["Jeongeup-si, Jeollabuk-do, Republic of Korea, 56212"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Punam","family":"Thapa","sequence":"additional","affiliation":[{"name":"Yeungnam University , , , ,","place":["Gyeongsan-si, Gyeongsangbuk-do, Republic of Korea, 38541"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hyun Mi","family":"Kim","sequence":"additional","affiliation":[{"name":"Korea Atomic Energy Research Institute , , , ,","place":["Jeongeup-si, Jeollabuk-do, Republic of Korea, 56212"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chang Hyun","family":"Jin","sequence":"additional","affiliation":[{"name":"Korea Atomic Energy Research Institute , , , ,","place":["Jeongeup-si, Jeollabuk-do, Republic of Korea, 56212"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sang Hoon","family":"Kim","sequence":"additional","affiliation":[{"name":"Korea Atomic Energy Research Institute , , , ,","place":["Jeongeup-si, Jeollabuk-do, Republic of Korea, 56212"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jin-Baek","family":"Kim","sequence":"additional","affiliation":[{"name":"Korea Atomic Energy Research Institute , , , ,","place":["Jeongeup-si, Jeollabuk-do, Republic of Korea, 56212"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7707-4767","authenticated-orcid":true,"given":"Hyukjae","family":"Choi","sequence":"additional","affiliation":[{"name":"Yeungnam University , , , ,","place":["Gyeongsan-si, Gyeongsangbuk-do, Republic of Korea, 38541"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7824-4441","authenticated-orcid":true,"given":"Ah-Reum","family":"Han","sequence":"additional","affiliation":[{"name":"Korea Atomic Energy Research Institute , , , ,","place":["Jeongeup-si, Jeollabuk-do, Republic of Korea, 56212"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joo-Won","family":"Nam","sequence":"additional","affiliation":[{"name":"Yeungnam University , , , ,","place":["Gyeongsan-si, Gyeongsangbuk-do, Republic of Korea, 38541"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,2,20]]},"reference":[{"key":"2026090207422672900_cit1","doi-asserted-by":"publisher","first-page":"454","DOI":"10.1039\/c4np00063c","article-title":"Chemistry and biological activity\nof steroidal glycosides from the Lilium genus","volume":"32","author":"Munafo","year":"2015","journal-title":"Nat. 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Compd."},{"key":"2026090207422672900_cit4","doi-asserted-by":"publisher","first-page":"1225","DOI":"10.1016\/0031-9422(95)00723-7","article-title":"A pyrroline\nglucoside ester and steroidal saponins from Lilium martagon","volume":"41","author":"Satou","year":"1996","journal-title":"Phytochemistry"},{"key":"2026090207422672900_cit5","doi-asserted-by":"publisher","first-page":"227","DOI":"10.1016\/0031-9422(94)85030-5","article-title":"Steroidal saponins from the bulbs of Lilium longiflorum\nand their antitumour-promoter activity","volume":"37","author":"Mimaki","year":"1994","journal-title":"Phytochemistry"},{"key":"2026090207422672900_cit6","doi-asserted-by":"publisher","first-page":"433","DOI":"10.1016\/j.jep.2013.04.032","article-title":"Steroidal\nglycosides from the bulbs of Easter lily (Lilium longiflorum Thunb.)\npromote dermal fibroblast migration in vitro","volume":"148","author":"Esposito","year":"2013","journal-title":"J. Ethnopharmacol."},{"key":"2026090207422672900_cit7","doi-asserted-by":"publisher","first-page":"8806","DOI":"10.1021\/jf101410d","article-title":"Isolation\nand structural determination of steroidal glycosides from the bulbs\nof Easter lily (Lilium longiflorum Thunb.)","volume":"58","author":"Munafo","year":"2010","journal-title":"J. Agric. Food Chem."},{"key":"2026090207422672900_cit8","doi-asserted-by":"publisher","first-page":"10670","DOI":"10.1021\/acsomega.9b00751","article-title":"Phenylpropanoid\nglycerol glucosides\nattenuate glucose production in hepatocytes","volume":"4","author":"Murray","year":"2019","journal-title":"ACS Omega"},{"key":"2026090207422672900_cit9","doi-asserted-by":"publisher","first-page":"4836","DOI":"10.1021\/acs.jafc.5b00893","article-title":"Quantitative\nanalysis of phenylpropanoid\nglycerol glucosides in different organs of Easter lily (Lilium longiflorum\nThunb.)","volume":"63","author":"Munafo","year":"2015","journal-title":"J. Agric. Food Chem."},{"key":"2026090207422672900_cit10","doi-asserted-by":"publisher","first-page":"527","DOI":"10.1007\/s13765-017-0307-7","article-title":"Phenylpropanoids from Lilium Asiatic\nhybrid flowers\nand their anti-inflammatory activities","volume":"60","author":"Thi","year":"2017","journal-title":"Appl.\nBiol. Chem."},{"key":"2026090207422672900_cit11","doi-asserted-by":"publisher","first-page":"1056","DOI":"10.1016\/j.foodchem.2011.09.112","article-title":"Preparative\nseparation of phenylpropenoid glycerides\nfrom the bulbs of Lilium lancifolium by high-speed counter-current\nchromatography and evaluation of their antioxidant activities","volume":"131","author":"Luo","year":"2012","journal-title":"Food Chem."},{"key":"2026090207422672900_cit12","doi-asserted-by":"publisher","first-page":"139","DOI":"10.1016\/s0021-9673(01)93958-5","article-title":"Chromatography\nof tannins: IV. 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Med."},{"key":"2026090207422672900_cit31","doi-asserted-by":"publisher","first-page":"6147","DOI":"10.1021\/jf500639f","article-title":"Bioactive compounds\nfrom culinary herbs inhibit a molecular target for type 2 diabetes\nmanagement, dipeptidyl peptidase IV","volume":"62","author":"Bower","year":"2014","journal-title":"J. Agric.\nFood Chem."},{"key":"2026090207422672900_cit32","doi-asserted-by":"publisher","first-page":"96","DOI":"10.1016\/j.bmcl.2014.11.001","article-title":"Anti-inflammatory\nand antitumor phenylpropanoid sucrosides from the seeds of Raphanus\nsativus","volume":"25","author":"Kim","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"2026090207422672900_cit33","doi-asserted-by":"publisher","first-page":"900","DOI":"10.1007\/s12272-001-1244-z","article-title":"Constituents of the flowers of Erigeron\nannuus with\ninhibitory activity on the formation of advanced glycation end products\n(AGEs) and aldose reductase","volume":"31","author":"Jang","year":"2008","journal-title":"Arch. Pharmacal\nRes."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.9b03649","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/5\/8\/4050\/67716132\/acsomega.9b03649.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/5\/8\/4050\/67716132\/acsomega.9b03649.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T11:42:35Z","timestamp":1788349355000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/5\/8\/4050\/616226\/Purification-of-Phenylpropanoids-from-the-Scaly"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,2,20]]},"references-count":33,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2020,2,20]]},"published-print":{"date-parts":[[2020,3,3]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.9b03649","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,2,20]]}}}