{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,17]],"date-time":"2026-06-17T02:54:41Z","timestamp":1781664881798,"version":"3.54.5"},"reference-count":107,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2021,6,19]],"date-time":"2021-06-19T00:00:00Z","timestamp":1624060800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["nyaspubs.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Annals of the New York Academy of Sciences"],"published-print":{"date-parts":[[2021,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Acankoreagenin (ACK, also known as acankoreanogenin and HLEDA) and impressic acid are two lupane\u2010type triterpenes that can be isolated from various <jats:italic>Acanthopanax<\/jats:italic> and <jats:italic>Schefflera<\/jats:italic> species. They efficiently block activation of the NF\u2010\u03baB signaling pathway and the release of proinflammatory cytokines and\/or the action of inflammation mediators (HMGB1, iNOS, and NO). These effects are the basis for the antiviral and anticancer activities reported with these pentacyclic compounds or their various glycoside derivatives. More than 15 acankoreosides (Ack\u2010A to \u2010O, and \u2010R) and a few other mono\u2010 and bidesmosidic saponins (acantrifoside A and acangraciliside S) derive from the ACK aglycone. Compounds like Ack\u2010A and \u2010B are remarkable anti\u2010inflammatory agents, inhibiting cytokine release from activated macrophages. Despite their effectiveness, ACK and impressic acid are far much less known and studied than the structurally related compounds betulinic acid and 23\u2010hydroxybetulinic acid (anemosapogenin). The structural differences (notably the <jats:italic>R<\/jats:italic>\/<jats:italic>S<\/jats:italic> stereoisomerism of the 3\u2010hydroxyl group) and functional similarities of these compounds are discussed. The complete series of acankoreosides is presented for the first time. These natural products deserve further attention as anti\u2010inflammatory agents, and ACK is recommended as a template for the design of new anticancer and antiviral drugs.<\/jats:p>","DOI":"10.1111\/nyas.14623","type":"journal-article","created":{"date-parts":[[2021,6,19]],"date-time":"2021-06-19T11:49:30Z","timestamp":1624103370000},"page":"14-27","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Acankoreagenin and acankoreosides, a family of lupane triterpenoids with anti\u2010inflammatory properties: an overview"],"prefix":"10.1111","volume":"1502","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2973-9357","authenticated-orcid":false,"given":"Christian","family":"Bailly","sequence":"first","affiliation":[{"name":"OncoWitan Lille (Wasquehal)  Wasquehal France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,6,19]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-020-10495-1"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24193546"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biotechadv.2019.06.008"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.5b06021"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24020355"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.12682"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0043-123472"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11596-018-1891-4"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1111\/nyas.13570"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apsb.2015.05.004"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2017.04.042"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.antiviral.2019.02.014"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1111\/bcpt.13504"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0024-3205(02)02176-8"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1080\/14786419.2011.559639"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1111\/bph.12995"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2010.02.004"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.3109\/13880209.2014.907323"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biopha.2016.10.018"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1080\/13880209.2019.1701500"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2011.03.038"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1002\/med.21353"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1111\/cbdd.12543"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2015.04.057"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2014.11.058"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2019.111659"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.8b00321"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1186\/s13046-016-0457-1"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41392-020-00251-2"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23010087"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1038\/aps.2014.97"},{"key":"e_1_2_6_33_1","first-page":"787","article-title":"[Synthesis of betulinic acid from betulin and study of its solubilization using liposomes]","volume":"24","author":"Son L.B.","year":"1998","journal-title":"Russian J. Bioorg. Chem"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1023\/A:1023220701797"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/np058016w"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12906-016-1397-1"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23061258"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.3390\/plants9101398"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2005-837818"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2005.10.063"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(82)80147-7"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(91)83647-4"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(91)83042-J"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2015.04.050"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules24162942"},{"key":"e_1_2_6_46_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.58.1596"},{"key":"e_1_2_6_47_1","doi-asserted-by":"publisher","DOI":"10.1002\/jssc.201500223"},{"key":"e_1_2_6_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1674-6384(14)60050-2"},{"key":"e_1_2_6_49_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23040958"},{"key":"e_1_2_6_50_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejphar.2015.10.017"},{"key":"e_1_2_6_51_1","doi-asserted-by":"publisher","DOI":"10.3390\/toxins12120794"},{"key":"e_1_2_6_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.intimp.2011.02.019"},{"key":"e_1_2_6_53_1","doi-asserted-by":"publisher","DOI":"10.3892\/mmr.2017.7767"},{"key":"e_1_2_6_54_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9FO00561G"},{"key":"e_1_2_6_55_1","doi-asserted-by":"publisher","DOI":"10.4062\/biomolther.2016.255"},{"key":"e_1_2_6_56_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11418-018-1262-2"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.semcdb.2018.03.012"},{"key":"e_1_2_6_58_1","doi-asserted-by":"publisher","DOI":"10.1080\/15548627.2020.1826690"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.REV119.008907"},{"key":"e_1_2_6_60_1","first-page":"68","article-title":"Smashing tissue extraction of active triterpenoids of anti\u2010HMGB1 from leaves of Acanthopanax gracilistylus W.W. Smith","volume":"42","author":"Liu X.Q.","year":"2011","journal-title":"J. Central South Univ"},{"key":"e_1_2_6_61_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11771-014-2277-9"},{"key":"e_1_2_6_62_1","article-title":"Acanthopanax trifoliatus, a potential adaptogenic Thai vegetable for health supplement","author":"Sithisarn P.","year":"2011","journal-title":"Phytochemicals"},{"key":"e_1_2_6_63_1","doi-asserted-by":"publisher","DOI":"10.1155\/2020\/7206451"},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcp.30125"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7RA11647K"},{"key":"e_1_2_6_66_1","first-page":"1","article-title":"Synergistic anticancer effect of gemcitabine combined with impressic acid or acankoreanogein in Panc\u20101 cells by inhibiting NF\u2010\u03baB and Stat 3 activation","volume":"15","author":"Jiang S.","year":"2020","journal-title":"Nat. Prod. Commun."},{"key":"e_1_2_6_67_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02980173"},{"key":"e_1_2_6_68_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12272-011-0815-7"},{"key":"e_1_2_6_69_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2017.07.034"},{"key":"e_1_2_6_70_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms20225772"},{"key":"e_1_2_6_71_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-017-05666-6"},{"key":"e_1_2_6_72_1","doi-asserted-by":"publisher","DOI":"10.1007\/s40203-021-00091-0"},{"key":"e_1_2_6_73_1","first-page":"198","article-title":"[Effect of 3\u2010hydroxy\u2010lup\u201020(29)en\u201023\u201028\u2010dioic acid on rat experimental gastric ulcers]","volume":"12","author":"Zhang S.R.","year":"1990","journal-title":"Zhongguo Yi Xue Ke Xue Yuan Xue Bao"},{"key":"e_1_2_6_74_1","doi-asserted-by":"publisher","DOI":"10.1002\/ptr.1962"},{"key":"e_1_2_6_75_1","doi-asserted-by":"publisher","DOI":"10.1080\/09168451.2017.1301803"},{"key":"e_1_2_6_76_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(00)00194-1"},{"key":"e_1_2_6_77_1","doi-asserted-by":"publisher","DOI":"10.1155\/2020\/7502301"},{"key":"e_1_2_6_78_1","doi-asserted-by":"publisher","DOI":"10.1186\/s13020-020-00410-1"},{"key":"e_1_2_6_79_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phymed.2019.152934"},{"key":"e_1_2_6_80_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phrs.2020.105079"},{"key":"e_1_2_6_81_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.intimp.2020.106794"},{"key":"e_1_2_6_82_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.50.1383"},{"key":"e_1_2_6_83_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02977000"},{"key":"e_1_2_6_84_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fitote.2013.10.006"},{"key":"e_1_2_6_85_1","doi-asserted-by":"publisher","DOI":"10.13005\/ojc\/280306"},{"key":"e_1_2_6_86_1","first-page":"340","article-title":"Separation of six lupane\u2010type triterpenoid saponins from leaves of Acanthopanax gracilistylus by HSCCC with preparative\u2010HPLC","volume":"3","author":"Luo J.","year":"2018","journal-title":"SDRP J. Food Sci. Technol"},{"key":"e_1_2_6_87_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.57.986"},{"key":"e_1_2_6_88_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12272-016-0879-5"},{"key":"e_1_2_6_89_1","doi-asserted-by":"publisher","DOI":"10.1186\/s12935-016-0369-3"},{"key":"e_1_2_6_90_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2017.12.060"},{"key":"e_1_2_6_91_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2020.103868"},{"key":"e_1_2_6_92_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02976706"},{"key":"e_1_2_6_93_1","first-page":"104","article-title":"Anti\u2010inflammatory activities of lupane\u2010triterpenoids in vitro and their phytochemical fingerprinting from leaves of Acanthopanax gracilistylus","volume":"21","author":"Li X.J.","year":"2015","journal-title":"Nat. Prod. Sci."},{"key":"e_1_2_6_94_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12272-012-0820-5"},{"key":"e_1_2_6_95_1","first-page":"1777","article-title":"Synthesis and biological evaluation of betulinic acid derivatives as new antitumor agents for leukemia","volume":"17","author":"Waechter F.","year":"2017","journal-title":"Anticancer Agents Med. Chem."},{"key":"e_1_2_6_96_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2017.09.041"},{"key":"e_1_2_6_97_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2018.03.067"},{"key":"e_1_2_6_98_1","doi-asserted-by":"crossref","first-page":"7289","DOI":"10.1021\/acs.jmedchem.8b00854","article-title":"Design, synthesis, and SAR of C\u20103 benzoic acid, C\u201017 triterpenoid derivatives. Identification of the HIV\u20101 maturation inhibitor 4\u2010((1 R,3a S,5a R,5b R,7a R,11a S,11b R,13a R,13b R)\u20103a\u2010((2\u2010(1,1\u2010dioxidothiomorpholino)ethyl)amino)\u20105a,5b,8,8,11a\u2010pentamethyl\u20101\u2010(prop\u20101\u2010en\u20102\u2010yl)\u20102,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b\u2010octadecahydro\u20101 H\u2010cyclopenta[ a]chrysen\u20109\u2010yl)benzoic acid (GSK3532795, BMS\u2010955176)","volume":"61","author":"Regueiro\u2010Ren A.","journal-title":"J. Med. Chem."},{"key":"e_1_2_6_99_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.steroids.2018.10.001"},{"key":"e_1_2_6_100_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2019.102957"},{"key":"e_1_2_6_101_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25040948"},{"key":"e_1_2_6_102_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.46.163"},{"key":"e_1_2_6_103_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(98)00402-6"},{"key":"e_1_2_6_104_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.53.97"},{"key":"e_1_2_6_105_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.56.1613"},{"key":"e_1_2_6_106_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0029-1186026"},{"key":"e_1_2_6_107_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2010.06.044"},{"key":"e_1_2_6_108_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(97)00846-7"}],"container-title":["Annals of the New York Academy of Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/nyas.14623","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1111\/nyas.14623","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/nyaspubs.onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/nyas.14623","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T05:38:48Z","timestamp":1693201128000},"score":1,"resource":{"primary":{"URL":"https:\/\/nyaspubs.onlinelibrary.wiley.com\/doi\/10.1111\/nyas.14623"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,6,19]]},"references-count":107,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2021,10]]}},"alternative-id":["10.1111\/nyas.14623"],"URL":"https:\/\/doi.org\/10.1111\/nyas.14623","archive":["Portico"],"relation":{},"ISSN":["0077-8923","1749-6632"],"issn-type":[{"value":"0077-8923","type":"print"},{"value":"1749-6632","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,6,19]]},"assertion":[{"value":"2021-03-10","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-05-21","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-06-19","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}