{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,8]],"date-time":"2026-05-08T09:19:01Z","timestamp":1778231941637,"version":"3.51.4"},"reference-count":23,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2015,10,22]],"date-time":"2015-10-22T00:00:00Z","timestamp":1445472000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000001","name":"the National Science Foundation","doi-asserted-by":"publisher","award":["81202890"],"award-info":[{"award-number":["81202890"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"name":"China Postdoctoral Science Foundation funded project","award":["2013M530164\/2014T70374"],"award-info":[{"award-number":["2013M530164\/2014T70374"]}]},{"name":"Heilongjiang Postdoctoral Fund","award":["LBH-Z13195"],"award-info":[{"award-number":["LBH-Z13195"]}]},{"name":"Harbin city youth science and technology innovation talents","award":["2013RFQXJ052"],"award-info":[{"award-number":["2013RFQXJ052"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Among the classes of identified natural products, triterpenoids, one of the largest families, have been studied extensively for their diverse structures and variety of biological activities, including antitumor effects. In the present study, a phytochemical study of the green walnut husks of Juglans mandshurica Maxim led to the isolation of a new dammarane triterpene, 12\u03b2, 20(R), 24(R)-trihydroxydammar-25-en-3-one (6), together with sixteen known compounds, chiefly from chloroform and ethyl acetate extracts. According to their structural characteristics, these compounds were divided into dammarane-type, oleanane- and ursane-type. Dammarane-type triterpenoids were isolated for the first time from the Juglans genus. As part of our continuing search for biologically active compounds from this plant, all of these compounds were also evaluated for their cytotoxic activities against the growth of human cancer cells lines HepG-2 by the MTT assay. The results were shown that 20(S)-protopanaxadiol, 2\u03b1,3\u03b2,23-trihydroxyolean-12-en-28-oic acid and 2\u03b1,3\u03b2,23-trihydroxyurs-12-en-28-oic acid exhibited better cytotoxicity in vitro with IC50 values of 10.32 \u00b1 1.13, 16.13 \u00b1 3.83, 15.97 \u00b1 2.47 \u03bcM, respectively. Preliminary structure-activity relationships for these compounds  were discussed.<\/jats:p>","DOI":"10.3390\/molecules201019252","type":"journal-article","created":{"date-parts":[[2015,10,26]],"date-time":"2015-10-26T04:12:04Z","timestamp":1445832724000},"page":"19252-19262","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":27,"title":["Cytotoxicity of Triterpenes from Green Walnut Husks of Juglans mandshurica Maxim in HepG-2 Cancer Cells"],"prefix":"10.3390","volume":"20","author":[{"given":"Yuanyuan","family":"Zhou","sequence":"first","affiliation":[{"name":"College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bingyou","family":"Yang","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhaoxi","family":"Liu","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yanqiu","family":"Jiang","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yuxin","family":"Liu","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lei","family":"Fu","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiaoli","family":"Wang","sequence":"additional","affiliation":[{"name":"College of Adult Education, Heilongjiang University of Chinese Medicine, Harbin 150040, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Haixue","family":"Kuang","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Heilongjiang University of Chinese Medicine, Harbin 150040, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2015,10,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0163-7258(03)00042-1","article-title":"Natural products for cancer prevention: A global perspective","volume":"99","author":"Reddy","year":"2003","journal-title":"Pharmacol. Ther."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1136","DOI":"10.1016\/j.drudis.2009.09.006","article-title":"Anticancer drug discovery in the future: An evolutionary perspective","volume":"14","author":"Ma","year":"2009","journal-title":"Drug Discov. Today"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1016\/j.fct.2009.10.043","article-title":"Human cancer cell antiproliferative and antioxidant activities of Juglans regia L.","volume":"48","author":"Carvalho","year":"2010","journal-title":"Food Chem. Toxicol."},{"key":"ref_4","first-page":"525","article-title":"Anti-proliferative effects of organic extracts from root bark of Juglans regia L. (RBJR) on MDA-MB-231 human breast cancer cells: Role of Bcl-2\/Bax, caspases and Tp53","volume":"12","author":"Hasan","year":"2011","journal-title":"Asian-Pac. J. Cancer Prev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"754","DOI":"10.1055\/s-2008-1074536","article-title":"Cytotoxic diarylheptanoids from the pericarps of walnuts (Juglans regia)","volume":"74","author":"Liu","year":"2008","journal-title":"Planta Med."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1416","DOI":"10.3109\/13880209.2012.682118","article-title":"Cytotoxicity effects of various Juglans regia (walnut) leaf extracts in human cancer cell lines","volume":"50","author":"Salimi","year":"2012","journal-title":"Pharm. Biol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"669","DOI":"10.3109\/13880209.2010.537666","article-title":"Antiproliferative and antioxidant activities of Juglans regia fruit extracts","volume":"49","author":"Negi","year":"2011","journal-title":"Pharm. Biol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1016\/j.phytol.2010.11.001","article-title":"2-Acety-1-(3-glycosyloxyoctadecanoyl) glycerol and dammarane triterpenes in the exudates from glandular trichome-like secretory organs on the stipules and leaves of Cerasus yedoensis","volume":"4","author":"Asai","year":"2011","journal-title":"Phytochem. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1935","DOI":"10.1016\/0040-4020(77)80379-7","article-title":"13C-NMR study of ginseng sapogenins and their related dammarane type triterpenes","volume":"33","author":"Asakawa","year":"1977","journal-title":"Tetrahedron"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1007\/BF00567286","article-title":"A new trirerpene from the leaves of Betula mandschurica","volume":"16","author":"Malinovskaya","year":"1980","journal-title":"Chem. Nat. Compd."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"877","DOI":"10.1016\/j.phytochem.2010.02.013","article-title":"Fatty acid derivatives and dammarane triterpenes from the glandular trichome exudates of Ibicella lutea and Proboscidea louisiana","volume":"71","author":"Asai","year":"2010","journal-title":"Phytochemistry"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"639","DOI":"10.1246\/bcsj.55.639","article-title":"The structure of anuserrutriol, a new C31 damarane-type triterpenoid from the male flowers of Alnus serrulatoides","volume":"55","author":"Hirata","year":"1982","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"614","DOI":"10.1002\/ptr.2661","article-title":"Triterpene acids isolated from Lagerstroemia speciosa leaves as \u03b1-glucosidase inhibitors","volume":"23","author":"Hou","year":"2009","journal-title":"Phytother. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1247","DOI":"10.1016\/0031-9422(80)83100-1","article-title":"3-Epikatonic acid from guar meal, Cyamopsis tetragonoloba","volume":"19","author":"David","year":"1980","journal-title":"Phytochemistry"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1549","DOI":"10.1080\/14786419.2011.566870","article-title":"Isolation, characterisation and cytotoxicity study of arjunolic acid from Terminalia arjuna","volume":"26","author":"Ramesh","year":"2012","journal-title":"Nat. Prod. Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"558","DOI":"10.1002\/ptr.2108","article-title":"Ursolic Acid: A Potent Inhibitor of Superoxides Produced in the Cellular System","volume":"21","author":"Ali","year":"2007","journal-title":"Phytother. Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"577","DOI":"10.1021\/np0496688","article-title":"Constituents of the leaves and twigs of Calyptranthes pallens collected from an experimental plot in southern florida","volume":"68","author":"Su","year":"2005","journal-title":"J. Nat. Prod."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2851","DOI":"10.1016\/S0031-9422(00)98105-6","article-title":"A pentacyclic triterpene acid, with anti-ulcer properties, from Cussonia natalensis","volume":"28","author":"Fourie","year":"1989","journal-title":"Phytochemistry"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/j.molcatb.2012.07.005","article-title":"Substrate specificity for the 2 \u03b1-hydroxylation of ursolic acid by Alternaria alternata and the antitumor activities of those metabolites","volume":"83","author":"Wang","year":"2012","journal-title":"J. Mol. Catal. B Enzym."},{"key":"ref_20","first-page":"19","article-title":"Drug cocktail therapy of traditional Chinese medicine in the Clinical and immunological research of the treatment of liver cancer","volume":"18","author":"Ren","year":"2000","journal-title":"Inform. Tradit. Chin. Med."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"558","DOI":"10.3109\/13880209.2012.749920","article-title":"Olamafar Shepatoprotective effects of juglans regia extract against ccl4-induced oxidative damage in rats","volume":"51","author":"Eidi","year":"2013","journal-title":"Pharm. Biol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4092","DOI":"10.1021\/ja00011a006","article-title":"High-field FT NMR application of Mosher\u2019s method. The absolute configurations of marine terpenoids","volume":"11","author":"Ohtani","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","first-page":"936","article-title":"Evaluation of a tetrazolium-based semiautomated colorimetric assay: Assessment of chemosensitivity testing","volume":"47","author":"Carmichael","year":"1987","journal-title":"Cancer Res."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/10\/19252\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T20:50:41Z","timestamp":1760215841000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/10\/19252"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,10,22]]},"references-count":23,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2015,10]]}},"alternative-id":["molecules201019252"],"URL":"https:\/\/doi.org\/10.3390\/molecules201019252","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,10,22]]}}}