{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,19]],"date-time":"2026-02-19T14:47:22Z","timestamp":1771512442435,"version":"3.50.1"},"reference-count":37,"publisher":"Georg Thieme Verlag KG","issue":"15","funder":[{"DOI":"10.13039\/501100005203","name":"OeAD-GmbH","doi-asserted-by":"crossref","award":["PL13\/2015"],"award-info":[{"award-number":["PL13\/2015"]}],"id":[{"id":"10.13039\/501100005203","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Planta Med"],"published-print":{"date-parts":[[2020,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>\n          Sigesbeckia orientalis, more commonly referred to as Herba Sigesbeckiae or Xi Xian Cao in traditional Chinese medicine and hy thi\u00eam in traditional Vietnamese medicine, is used in China and Vietnam to treat inflammatory diseases such as arthritis, rheumatism, and joint pain. In initial investigations, the dichloromethane extract from the aerial parts of S. orientalis showed distinct inhibitory effects on the release of interleukin-8 in human neutrophils. Therefore, the purpose of the present study was the phytochemical investigation of the bioactive dichloromethane extract and the in vitro analysis of the effects of the isolated compounds on interleukin-8, interleukin-1\u03b2, tumor necrosis factor-\u03b1, and monocyte chemoattractant protein 1 release, and surface expression of adhesion molecules (CD11a, CD11b, and CD62L) in lipopolysaccharide-stimulated human neutrophils to identify the active principle(s). The separation of the bioactive\n\t\t\t\t\tdichloromethane extract using various chromatographic techniques led to the isolation of nine compounds. Their chemical structures were elucidated from nuclear magnetic resonance and mass spectrometry data. One diterpene, 17(13\u2009\u2192\u200914)-abeo-ent-3S*,13S*,16-trihydroxystrob-8(15)-ene, was identified as a new natural product. Three germacranolide sesquiterpene lactones inhibited interleukin-8 production with IC50 values between 1.6 and 6.3\u2009\u00b5M, respectively, and tumor necrosis factor-\u03b1 production with IC50 values between 0.9 and 3.3\u2009\u00b5M, respectively. Furthermore, they significantly inhibited interleukin-1\u03b2 and monocyte chemoattractant protein 1 production and diminished the effects of lipopolysaccharide on the surface expression of the adhesion molecules CD11a, CD11b, and CD62L. These findings support the traditional use of S.\u00a0orientalis in the treatment of inflammatory diseases.<\/jats:p>","DOI":"10.1055\/a-1232-6869","type":"journal-article","created":{"date-parts":[[2020,9,21]],"date-time":"2020-09-21T22:58:40Z","timestamp":1600729120000},"page":"1108-1117","source":"Crossref","is-referenced-by-count":10,"title":["A New Diterpene and Anti-inflammatory Sesquiterpene Lactones from Sigesbeckia orientalis"],"prefix":"10.1055","volume":"86","author":[{"given":"Nora S.","family":"Engels","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy\/Pharmacognosy and Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innsbruck, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Barbara","family":"Gierlikowska","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw, Warsaw, Poland"},{"name":"Department of Laboratory Diagnostics and Clinical Immunology of Developmental Age, Medical University of Warsaw, Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2718-4677","authenticated-orcid":false,"given":"Birgit","family":"Waltenberger","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy\/Pharmacognosy and Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innsbruck, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fang-Rong","family":"Chang","sequence":"additional","affiliation":[{"name":"Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan"},{"name":"National Research Institute of Chinese Medicine, Ministry of Health and Welfare, Taipei, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anna K.","family":"Kiss","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw, Warsaw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hermann","family":"Stuppner","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy\/Pharmacognosy and Center for Molecular Biosciences Innsbruck (CMBI), University of Innsbruck, Innsbruck, Austria"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"194","published-online":{"date-parts":[[2020,9,21]]},"reference":[{"key":"ref1","doi-asserted-by":"crossref","DOI":"10.1201\/b16504","volume-title":"CRC World Dictionary of medicinal and poisonous Plants: common Names, scientific Names, Eponyms, Synonyms, and Etymology","author":"U Quattrocchi","year":"2012"},{"key":"ref2","first-page":"1526","article-title":"Spectrophotometric estimation of antioxidant activity of Siegesbeckia orientalis plant extracts by hydrogen peroxide scavenging method","volume":"6","author":"V Manjusha","year":"2017","journal-title":"World J Pharm Pharm Sci"},{"key":"ref3","first-page":"199","article-title":"Screening for antioxidative activity of crude drugs","volume":"50","author":"J D Su","year":"1986","journal-title":"Agric Biol Chem"},{"key":"ref4","doi-asserted-by":"crossref","first-page":"754","DOI":"10.1002\/cbdv.200690077","article-title":"Immunosuppressive activity of the ethanol extract of Siegesbeckia orientalis on the immune responses to ovalbumin in mice","volume":"3","author":"H X Sun","year":"2006","journal-title":"Chem Biodivers"},{"key":"ref5","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1186\/s12906-017-1698-z","article-title":"Anti-hyperuricemic, anti-inflammatory and analgesic effects of Siegesbeckia orientalis L. resulting from the fraction with high phenolic content","volume":"17","author":"T D Nguyen","year":"2017","journal-title":"BMC Complement Altern Med"},{"key":"ref6","first-page":"329712","article-title":"Anti-inflammatory effects of Siegesbeckia orientalis ethanol extract in in vitro and in vivo models","volume":"2014","author":"Y H Hong","year":"2014","journal-title":"Biomed Res Int"},{"key":"ref7","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1186\/s12906-018-2205-x","article-title":"Comparison of the chemical profiles and inflammatory mediator-inhibitory effects of three Siegesbeckia herbs used as Herba Siegesbeckiae (Xixiancao)","volume":"18","author":"H Guo","year":"2018","journal-title":"BMC Complement Altern Med"},{"key":"ref8","doi-asserted-by":"crossref","first-page":"2185","DOI":"10.3390\/molecules23092185","article-title":"Comparative analysis of chemical composition, anti-inflammatory activity and antitumor activity in essential oils from Siegesbeckia orientalis, S. glabrescens and S. pubescens with an ITS sequence analysis","volume":"23","author":"X Gao","year":"2018","journal-title":"Molecules"},{"key":"ref9","doi-asserted-by":"crossref","first-page":"882","DOI":"10.1016\/j.phymed.2012.04.010","article-title":"Kirenol exerts a potent anti-arthritic effect in collagen-induced arthritis by modifying the T cells balance","volume":"19","author":"Y Lu","year":"2012","journal-title":"Phytomedicine"},{"key":"ref10","doi-asserted-by":"crossref","first-page":"1089","DOI":"10.1016\/j.jep.2011.07.016","article-title":"Topical anti-inflammatory and analgesic activity of kirenol isolated from Siegesbeckia orientalis","volume":"137","author":"J P Wang","year":"2011","journal-title":"J Ethnopharmacol"},{"key":"ref11","first-page":"67","article-title":"Purified plant extracts. Demonstrating the cosmetic activity of darutoside, esculoside and ursolic acid","volume":"113","author":"K Lintner","year":"1998","journal-title":"Cosm Toil"},{"key":"ref12","doi-asserted-by":"crossref","first-page":"400","DOI":"10.1016\/j.phytochem.2015.07.005","article-title":"Diterpenoids from aerial parts of Flickingeria fimbriata and their nuclear factor-kappaB inhibitory activities","volume":"117","author":"H Li","year":"2015","journal-title":"Phytochemistry"},{"issue":"S 02","key":"ref13","doi-asserted-by":"crossref","first-page":"e12943","DOI":"10.1111\/eci.12943","article-title":"Neutrophil phenotypes in health and disease","volume":"48","author":"P Hellebrekers","year":"2018","journal-title":"Eur J Clin Invest"},{"key":"ref14","doi-asserted-by":"crossref","first-page":"195","DOI":"10.1034\/j.1600-065X.2000.17706.x","article-title":"The neutrophil as a cellular source of chemokines","volume":"177","author":"P Scapini","year":"2000","journal-title":"Immunol Rev"},{"key":"ref15","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1016\/0014-5793(92)80909-Z","article-title":"Interleukin-8, a chemotactic and inflammatory cytokine","volume":"307","author":"M Baggiolini","year":"1992","journal-title":"FEBS Lett"},{"key":"ref16","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1021\/acs.jnatprod.6b00150","article-title":"ent-Strobane and ent-pimarane diterpenoids from Siegesbeckia pubescens","volume":"80","author":"J Wang","year":"2017","journal-title":"J Nat Prod"},{"key":"ref17","doi-asserted-by":"crossref","first-page":"1323","DOI":"10.1002\/ptr.3420","article-title":"In vitro antiinflammatory activity of a new sesquiterpene lactone isolated from Siegesbeckia glabrescens","volume":"25","author":"H Li","year":"2011","journal-title":"Phytother Res"},{"key":"ref18","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1016\/S0031-9422(00)81985-8","article-title":"New melampolides and darutigenol from Sigesbeckia orientalis","volume":"19","author":"R N Barua","year":"1980","journal-title":"Phytochemistry"},{"key":"ref19","doi-asserted-by":"crossref","first-page":"1929","DOI":"10.1016\/0031-9422(91)85042-X","article-title":"Melampolides and other constituents from Furinea leptoloba","volume":"30","author":"A Rustaiyan","year":"1991","journal-title":"Phytochemistry"},{"key":"ref20","doi-asserted-by":"crossref","first-page":"991","DOI":"10.1016\/S0031-9422(00)91462-6","article-title":"A new melampolide from Sigesbeckia orientalis","volume":"18","author":"R N Baruah","year":"1979","journal-title":"Phytochemistry"},{"key":"ref21","doi-asserted-by":"crossref","first-page":"537","DOI":"10.1246\/cl.1975.537","article-title":"O-Acetyl-N-(N\u02bc-benzoyl-L-phenylalanyl)-L-phenylalaninol. Isolation from Euphorbia fischeriana Steudel","volume":"4","author":"D Uemura","year":"1975","journal-title":"Chem Lett"},{"key":"ref22","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1248\/cpb.53.232","article-title":"ent-Pimarane-type diterpenoids from Siegesbeckia orientalis L","volume":"53","author":"P M Giang","year":"2005","journal-title":"Chem Pharm Bull"},{"key":"ref23","doi-asserted-by":"crossref","first-page":"2545","DOI":"10.1016\/0040-4020(76)88024-6","article-title":"Lactones sesquiterpeniques du Vernonia pectoralis Baker (composees). Stereochimie du pectorolide, et structure des vernopectolides-A et B","volume":"32","author":"B Mompon","year":"1976","journal-title":"Tetrahedron"},{"key":"ref24","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1021\/np1003017","article-title":"Quercetin reduces neutrophil recruitment induced by CXCL8, LTB4, and fMLP: inhibition of actin polymerization","volume":"74","author":"F O Souto","year":"2011","journal-title":"J Nat Prod"},{"key":"ref25","doi-asserted-by":"crossref","first-page":"500","DOI":"10.1007\/s00011-005-1385-2","article-title":"Quercetin inhibits LPS-induced delay in spontaneous apoptosis and activation of neutrophils","volume":"54","author":"J J Liu","year":"2005","journal-title":"Inflamm Res"},{"key":"ref26","doi-asserted-by":"crossref","first-page":"401","DOI":"10.3389\/fphar.2018.00401","article-title":"Lignans from Forsythia x intermedia leaves and flowers attenuate the pro-inflammatory function of leukocytes and their interaction with endothelial cells","volume":"9","author":"B Michalak","year":"2018","journal-title":"Front Pharmacol"},{"key":"ref27","doi-asserted-by":"crossref","first-page":"998","DOI":"10.1016\/j.biocel.2008.07.018","article-title":"Monocyte chemoattractant protein-1: a key mediator in inflammatory processes","volume":"41","author":"E Melgarejo","year":"2009","journal-title":"Int J Biochem Cell Biol"},{"key":"ref28","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1203\/00006450-199602000-00001","article-title":"Adhesion molecules \u2013 their role in health and disease","volume":"39","author":"A Etzioni","year":"1996","journal-title":"Pediatr Res"},{"key":"ref29","doi-asserted-by":"crossref","first-page":"713","DOI":"10.1016\/S1074-7613(03)00295-4","article-title":"Leukocyte migration is regulated by L-selectin endoproteolytic release","volume":"19","author":"G M Venturi","year":"2003","journal-title":"Immunity"},{"key":"ref30","first-page":"908468","article-title":"Recent advances in underlying pathologies provide insight into interleukin-8 expression-mediated inflammation and angiogenesis","volume":"2011","author":"B S Qazi","year":"2011","journal-title":"Int J Inflam"},{"key":"ref31","doi-asserted-by":"crossref","first-page":"751","DOI":"10.1194\/jlr.R600021-JLR200","article-title":"The role of TNF-alpha in chronic inflammatory conditions, intermediary metabolism, and cardiovascular risk","volume":"48","author":"C Popa","year":"2007","journal-title":"J Lipid Res"},{"key":"ref32","doi-asserted-by":"crossref","first-page":"3720","DOI":"10.1182\/blood-2010-07-273417","article-title":"Interleukin-1 in the pathogenesis and treatment of inflammatory diseases","volume":"117","author":"C A Dinarello","year":"2011","journal-title":"Blood"},{"key":"ref33","doi-asserted-by":"crossref","first-page":"759","DOI":"10.1016\/S1074-5521(01)00049-7","article-title":"The anti-inflammatory natural product parthenolide from the medicinal herb feverfew directly binds to and inhibits IkappaB kinase","volume":"8","author":"B H Kwok","year":"2001","journal-title":"Chem Biol"},{"key":"ref34","doi-asserted-by":"crossref","first-page":"951","DOI":"10.1515\/bchm.1997.378.9.951","article-title":"Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB","volume":"378","author":"G Lyss","year":"1997","journal-title":"Biol Chem"},{"key":"ref35","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1080\/08923973.2016.1267744","article-title":"Artemisinin inhibits inflammatory response via regulating NF-kappaB and MAPK signaling pathways","volume":"39","author":"K S Wang","year":"2017","journal-title":"Immunopharmacol Immunotoxicol"},{"key":"ref36","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1006\/cyto.1999.0526","article-title":"Sesquiterpene lactones are potent inhibitors of interleukin 8 gene expression in cultured human respiratory epithelium","volume":"12","author":"R L Mazor","year":"2000","journal-title":"Cytokine"},{"key":"ref37","doi-asserted-by":"crossref","first-page":"6042","DOI":"10.1021\/jm049937r","article-title":"Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-kappaB","volume":"47","author":"B Siedle","year":"2004","journal-title":"J Med Chem"}],"container-title":["Planta Medica"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.thieme-connect.de\/products\/ejournals\/pdf\/10.1055\/a-1232-6869.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2020,10,13]],"date-time":"2020-10-13T22:43:06Z","timestamp":1602628986000},"score":1,"resource":{"primary":{"URL":"http:\/\/www.thieme-connect.de\/DOI\/DOI?10.1055\/a-1232-6869"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,9,21]]},"references-count":37,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2020,10,13]]},"published-print":{"date-parts":[[2020,10]]}},"URL":"https:\/\/doi.org\/10.1055\/a-1232-6869","relation":{},"ISSN":["0032-0943","1439-0221"],"issn-type":[{"value":"0032-0943","type":"print"},{"value":"1439-0221","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,9,21]]}}}