{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,14]],"date-time":"2026-11-14T07:45:58Z","timestamp":1794642358296,"version":"4.9.1"},"reference-count":0,"publisher":"Walter de Gruyter GmbH","issue":"5-6","license":[{"start":{"date-parts":[[2009,6,1]],"date-time":"2009-06-01T00:00:00Z","timestamp":1243814400000},"content-version":"unspecified","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2009,6,1]]},"abstract":"I<\/jats:title>\n From osthole [7-methoxy-8-(3-methyl-but-2-enyl)-chromen-2-one] (), obtained by selective extraction of Peucedanum ostruthium (L.) W. Koch roots, ostholic acid (II<\/jats:bold>) was synthetized as a result of its oxidation with chromium trioxide. From ostholic acid, through its chloride, four amides were obtained: the morpholide 1<\/jats:bold>, the p-chloro-benzylamide 2<\/jats:bold>, the piperidine 3 <\/jats:bold>and the N-methyl-piperazide 4<\/jats:bold>. Except for 1<\/jats:bold>, other compounds have not been described before. The amides 1 <\/jats:bold>- 4 <\/jats:bold>and their precursor osthole (I<\/jats:bold>) were tested for their potential activities in selected immunological assays. The compounds showed moderate inhibitory activity in the humoral immune response to sheep erythrocytes in mice in vitro, and 4 <\/jats:bold>was the most suppressive. The effects of 1 <\/jats:bold>and 3 <\/jats:bold>on concanavalin A- and pokeweed mitogen-induced mouse splenocyte proliferation were inhibitory and those of 4 <\/jats:bold>stimulatory. The compounds were also tested for their activity on tumour necrosis factor \u03b1 and interleukin 6 production, induced by lipopolysaccharide, in cultures of rat peritoneal cells and human peripheral blood mononuclear cells. Compounds 1<\/jats:bold>, 3 <\/jats:bold>and 4 <\/jats:bold>inhibited tumour necrosis factor \u03b1 (rat cells), whereas compound 2 <\/jats:bold>stimulated the production of both cytokines. Compounds 1<\/jats:bold>, 2 <\/jats:bold>and 3 <\/jats:bold>were also strongly inhibitory on tumour necrosis factor \u03b1 production in human blood cells (73, 78 and 80% inhibition at 10 \u03bcg\/ml, respectively). On the other hand, 2 <\/jats:bold>and 4 <\/jats:bold>stimulated the interleukin 6 production (2- to 3-fold stimulation). In addition, 2 <\/jats:bold>and 4 <\/jats:bold>suppressed the carrageenan-induced inflammation in mice (56.5% and 68.3% inhibition, respectively). In summary, the compounds predominantly displayed suppressive and anti inflammatory activities in the investigated models<\/jats:p>","DOI":"10.1515\/znc-2009-5-610","type":"journal-article","created":{"date-parts":[[2015,1,30]],"date-time":"2015-01-30T12:36:04Z","timestamp":1422621364000},"page":"361-368","source":"Crossref","is-referenced-by-count":44,"title":["Immunomodulatory and Anti-Inflammatory Activity of Selected Osthole Derivatives"],"prefix":"10.1515","volume":"64","author":[{"given":"Micha\u0142","family":"Zimecki","sequence":"first","affiliation":[{"name":"Department of Experimental Therapy, Institute of Immunology and Experimental Therapy, R. Weigla str. 12, 53 \u2013 114, Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jolanta","family":"Artym","sequence":"additional","affiliation":[{"name":"Department of Experimental Therapy, Institute of Immunology and Experimental Therapy, R. Weigla str. 12, 53 \u2013 114, Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wojciech","family":"Cisowski","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Wroclaw Medical University, Nankiera sq. 1, 50 \u2013 140 Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irena","family":"Ma\u017col","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Wroclaw Medical University, Nankiera sq. 1, 50 \u2013 140 Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maciej","family":"W\u0142odarczyk","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Wroclaw Medical University, Nankiera sq. 1, 50 \u2013 140 Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Micha\u0142","family":"Glen\u015bk","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Wroclaw Medical University, Nankiera sq. 1, 50 \u2013 140 Wroclaw, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"374","published-online":{"date-parts":[[2014,6,2]]},"container-title":["Zeitschrift f\u00fcr Naturforschung C"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.degruyter.com\/view\/journals\/znc\/64\/5-6\/article-p361.xml","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/znc-2009-5-610\/xml","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/znc-2009-5-610\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,6,22]],"date-time":"2021-06-22T06:17:29Z","timestamp":1624342649000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.degruyter.com\/document\/doi\/10.1515\/znc-2009-5-610\/html"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,6,1]]},"references-count":0,"journal-issue":{"issue":"5-6","published-online":{"date-parts":[[2014,6,2]]},"published-print":{"date-parts":[[2009,6,1]]}},"alternative-id":["10.1515\/znc-2009-5-610"],"URL":"https:\/\/doi.org\/10.1515\/znc-2009-5-610","relation":{},"ISSN":["1865-7125","0939-5075"],"issn-type":[{"value":"1865-7125","type":"electronic"},{"value":"0939-5075","type":"print"}],"subject":[],"published":{"date-parts":[[2009,6,1]]}}}