{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T04:50:56Z","timestamp":1789620656917,"version":"build-2803163510"},"reference-count":42,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2013,11,12]],"date-time":"2013-11-12T00:00:00Z","timestamp":1384214400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>In the course of studies on bioactive metabolites from marine fungi, a new  10-membered lactone, named penicillinolide A (1) was isolated from the organic extract of Penicillium sp. SF-5292 as a potential anti-inflammatory compound. The structure of penicillinolide A (1) was mainly determined by analysis of NMR and MS data and Mosher\u2019s method. Penicillinolide A (1) inhibited the production of NO and PGE2 due to inhibition of the expression of iNOS and COX-2. Penicillinolide A (1) also reduced  TNF-\u03b1, IL-1\u03b2 and IL-6 production, and these anti-inflammatory effects were shown to be correlated with the suppression of the phosphorylation and degradation of I\u03baB-\u03b1, NF-\u03baB nuclear translocation, and NF-\u03baB DNA binding activity. In addition, using inhibitor tin protoporphyrin (SnPP), a competitive inhibitor of HO activity, it was verified that the inhibitory effects of compound 1 on the production of pro-inflammatory mediators and NF-\u03baB DNA binding activity were partially associated with HO-1 expression through Nrf2 nuclear translocation.<\/jats:p>","DOI":"10.3390\/md11114510","type":"journal-article","created":{"date-parts":[[2013,11,12]],"date-time":"2013-11-12T10:43:07Z","timestamp":1384252987000},"page":"4510-4526","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":34,"title":["Penicillinolide A: A New Anti-Inflammatory Metabolite from the Marine Fungus Penicillium sp. SF-5292"],"prefix":"10.3390","volume":"11","author":[{"given":"Dong-Sung","family":"Lee","sequence":"first","affiliation":[{"name":"Department of Pharmacy, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea"},{"name":"Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wonmin","family":"Ko","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea"},{"name":"Standardized Material Bank for New Botanical Drugs, College of Pharmacy,  Wonkwang University, Iksan 570-749, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tran","family":"Quang","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea"},{"name":"Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST),  18 Hoang Quoc Viet, Caugiay, Hanoi 10000, Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kyoung-Su","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea"},{"name":"Standardized Material Bank for New Botanical Drugs, College of Pharmacy,  Wonkwang University, Iksan 570-749, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jae","family":"Sohn","sequence":"additional","affiliation":[{"name":"College of Medical and Life Sciences, Silla University, Busan 617-736, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jae-Hyuk","family":"Jang","sequence":"additional","affiliation":[{"name":"Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), 30 Yeongudanji-ro, Ochang, Cheongwon 363-883, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jong","family":"Ahn","sequence":"additional","affiliation":[{"name":"Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), 30 Yeongudanji-ro, Ochang, Cheongwon 363-883, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Youn-Chul","family":"Kim","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea"},{"name":"Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Korea"},{"name":"Standardized Material Bank for New Botanical Drugs, College of Pharmacy,  Wonkwang University, Iksan 570-749, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hyuncheol","family":"Oh","sequence":"additional","affiliation":[{"name":"Department of Pharmacy, College of Pharmacy, Wonkwang University, Iksan 570-749, Korea"},{"name":"Hanbang Body-Fluid Research Center, Wonkwang University, Iksan 570-749, Korea"},{"name":"Standardized Material Bank for New Botanical Drugs, College of Pharmacy,  Wonkwang University, Iksan 570-749, Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2013,11,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2150","DOI":"10.1073\/pnas.94.6.2150","article-title":"Discovery and analysis of inflammatory disease-related genes using cdna microarrays","volume":"94","author":"Heller","year":"1997","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1124\/pr.107.07104","article-title":"Pharmacological and clinical aspects of heme oxygenase","volume":"60","author":"Abraham","year":"2008","journal-title":"Pharmcol. Rev."},{"key":"ref_3","first-page":"L688","article-title":"Carbon monoxide provides protection against hyperoxic lung injury","volume":"276","author":"Otterbein","year":"1999","journal-title":"Am. J. Physiol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"583","DOI":"10.1152\/physrev.00011.2005","article-title":"Heme oxygenase-1\/carbon monoxide: From basic science to therapeutic applications","volume":"86","author":"Ryter","year":"2006","journal-title":"Physiol. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1038\/74680","article-title":"Carbon monoxide has anti-inflammatory effects involving the mitogen-activated protein kinase pathway","volume":"6","author":"Otterbein","year":"2000","journal-title":"Nat. Med."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"19325","DOI":"10.1074\/jbc.M300498200","article-title":"Induction of heme oxygenase-1 expression in murine macrophages is essential for the anti-inflammatory effect of low dose 15-deoxy-delta 12,14-prostaglandin J2","volume":"278","author":"Lee","year":"2003","journal-title":"J. Biol. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"24840","DOI":"10.1074\/jbc.M000835200","article-title":"Thioredoxin facilitates the induction of heme oxygenase-1 in response to inflammatory mediators","volume":"275","author":"Wiesel","year":"2000","journal-title":"J. Biol. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"36993","DOI":"10.1074\/jbc.M302942200","article-title":"Suppression of inflammatory cytokine production by carbon monoxide involves the JNK pathway and AP-1","volume":"278","author":"Morse","year":"2003","journal-title":"J. Biol. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"220","DOI":"10.1165\/rcmb.2005-0154OC","article-title":"CCAAT\/enhancer-binding protein mediates carbon monoxide-induced suppression of cyclooxygenase-2","volume":"35","author":"Suh","year":"2006","journal-title":"Am. J. Respir. Cell Mol. Biol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1016\/j.freeradbiomed.2006.03.021","article-title":"Hydrogen sulfide inhibits nitric oxide production and nuclear factor kappa B via heme oxygenase-1 expression in RAW264.7 macrophages stimulated with lipopolysaccharide","volume":"41","author":"Oh","year":"2006","journal-title":"Free Radic. Biol. Med."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1156","DOI":"10.1016\/j.bbrc.2004.06.061","article-title":"3-Hydroxyanthranilic acid, one of metabolites of tryptophan via indoleamine 2,3-dioxygenase pathway, suppresses inducible nitric oxide synthase expression by enhancing heme oxygenase-1 expression","volume":"320","author":"Oh","year":"2004","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4210","DOI":"10.2174\/138161211798764799","article-title":"Gene therapy targeting inflammation in atherosclerosis","volume":"17","author":"Huygelen","year":"2011","journal-title":"Curr. Pharm. Des."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"850","DOI":"10.1016\/j.intimp.2010.04.019","article-title":"Anti-inflammatory effects of sulfuretin from Rhus verniciflua stokes via the induction of heme oxygenase-1 expression in murine macrophages","volume":"10","author":"Lee","year":"2010","journal-title":"Int. Immunopharmacol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1131","DOI":"10.1016\/S0192-0561(00)00064-3","article-title":"Resolution of inflammation","volume":"22","author":"Willoughby","year":"2000","journal-title":"Int. J. Immunopharmacol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1192","DOI":"10.2353\/ajpath.2007.060782","article-title":"Statins attenuate ischemia-reperfusion injury by inducing heme oxygenase-1 in infiltrating macrophages","volume":"170","author":"Gueler","year":"2007","journal-title":"Am. J. Pathol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1742","DOI":"10.1038\/sj.ki.5001893","article-title":"The role of heme oxygenase 1 in rapamycin-induced renal dysfunction after ischemia and reperfusion injury","volume":"70","author":"Cenedeze","year":"2006","journal-title":"Kidney Int."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"33422","DOI":"10.1074\/jbc.M602074200","article-title":"Heme oxygenase-1 protects gastric mucosal cells against nonsteroidal anti-inflammatory drugs","volume":"281","author":"Aburaya","year":"2006","journal-title":"J. Biol. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1007\/s00204-011-0674-5","article-title":"The cytoprotective role of the Keap1\u2013Nrf2 pathway","volume":"85","author":"Baird","year":"2011","journal-title":"Arch. Toxicol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1016\/S0891-5849(00)00306-3","article-title":"Regulation of genes encoding NAD(P)H: Quinine oxidoreductases","volume":"29","author":"Jaiswal","year":"2000","journal-title":"Free Radic. Biol. Med."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"887","DOI":"10.1042\/bj20021619","article-title":"Curcumin activates the haem oxygenase-1 gene via regulation of NRF2 and he antioxidant-responsive element","volume":"371","author":"Balogun","year":"2003","journal-title":"Biochem. J."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1254\/jphs.10219FP","article-title":"Asperlin from the marine-derived fungus Aspergillus sp. SF-5044 exerts anti-inflammatory effects through heme oxygenase-1 expression in murine macrophages","volume":"116","author":"Lee","year":"2011","journal-title":"J. Pharmacol. Sci."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1409","DOI":"10.3390\/md11041409","article-title":"PTP1B inhibitory and anti-inflammatory effects of secondary metabolites isolated from the marine-derived fungus Penicillium sp. JF-55","volume":"11","author":"Lee","year":"2013","journal-title":"Mar. Drugs"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"666","DOI":"10.1038\/nchembio841","article-title":"Developing a new resource for drug discovery: Marine actinomycete bacteria","volume":"2","author":"Fenical","year":"2006","journal-title":"Nat. Chem. Biol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1039\/b301926h","article-title":"Marine-derived fungi: A chemically and biologically diverse group of microorganisms","volume":"21","author":"Bugni","year":"2004","journal-title":"Nat. Prod. Rep."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1142","DOI":"10.1039\/b607254m","article-title":"Marine natural products of fungal origin","volume":"24","author":"Saleem","year":"2007","journal-title":"Nat. Prod. Rep."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1284","DOI":"10.1021\/np100880b","article-title":"Protuboxepins A and B and protubonines A and B from the marine-derived fungus Aspergillus sp. SF-5044","volume":"74","author":"Lee","year":"2011","journal-title":"J. Nat. Prod."},{"key":"ref_27","first-page":"77","article-title":"Alternaramide, a cyclic depsipeptide from the marine-derived fungus Alternaria sp. SF-5016","volume":"72","author":"Kim","year":"2005","journal-title":"J. Nat. Prod."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1038\/333664a0","article-title":"Vascular endothelial cells synthesize nitric oxide from l-Arginine","volume":"333","author":"Palmer","year":"1988","journal-title":"Nature"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.pneurobio.2005.06.004","article-title":"Microglia and inflammation-mediated neurodegeneration: Multiple triggers with a common mechanism","volume":"76","author":"Block","year":"2005","journal-title":"Prog. Neurobiol."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1016\/S0027-5107(01)00183-X","article-title":"Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: Down-regulation of COX-2 and iNOS through suppression of NF-kappa B activation","volume":"480\u2013481","author":"Surh","year":"2001","journal-title":"Mutat. Res."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2723","DOI":"10.1101\/gad.9.22.2723","article-title":"Rel\/NF-kappaB\/I kappaB family: Intimate tales of association and dissociation","volume":"9","author":"Verma","year":"1995","journal-title":"Genes Dev."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1895","DOI":"10.1016\/j.bcp.2010.07.014","article-title":"Signaling to heme oxygenase-1 and its anti-inflammatory therapeutic potential","volume":"80","author":"Paine","year":"2010","journal-title":"Biochem. Pharmacol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.tox.2007.10.029","article-title":"The Nrf2-Keap1 defence pathway: Role in protection against drug-induced toxicity","volume":"246","author":"Copple","year":"2008","journal-title":"Toxicology"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1485","DOI":"10.1016\/j.bcp.2008.07.017","article-title":"Activation of Nrf2-antioxidant signaling attenuates NFkappaB-inflammatory response and elicits apoptosis","volume":"76","author":"Li","year":"2008","journal-title":"Biochem. Pharmacol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"7036","DOI":"10.1016\/S0021-9258(19)39255-5","article-title":"Interferon gamma and interleukin 2 synergize to induce selective monokine expression in murine peritoneal macrophages","volume":"265","author":"Narumi","year":"1990","journal-title":"J. Biol. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"474","DOI":"10.1006\/abbi.1993.1311","article-title":"Characterization of the cellular reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT): Subcellular localization, substrate dependence, and involvement of mitochondrial electron transport in MTT reduction","volume":"303","author":"Berridge","year":"1993","journal-title":"Arch. Biochem. Biophys."},{"key":"ref_37","first-page":"83","article-title":"The Enzymatic Measurement of Nitrate and Nitrite","volume":"101","author":"Titheradge","year":"1998","journal-title":"Meth. Mol. Biol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"800","DOI":"10.1038\/sj.bjp.0706241","article-title":"Carbon monoxide-releasing molecules (CO-RMs) attenuate the inflammatory response elicited by lipopolysaccharide in RAW264.7 murine macrophages","volume":"145","author":"Sawle","year":"2005","journal-title":"Br. J. Pharmacol."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3417","DOI":"10.2174\/092986712801215874","article-title":"Nonanolides of natural origin: Structure, synthesis, and biological activity","volume":"19","author":"Sun","year":"2012","journal-title":"Curr. Med. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2279","DOI":"10.1016\/j.tet.2007.11.034","article-title":"Fifteen years of biological and synthetic studies of decarestrictine family","volume":"64","author":"Riatto","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"941","DOI":"10.1016\/S0031-9422(97)00879-0","article-title":"Putaminoxins D and E from Phoma putaminum","volume":"48","author":"Evidente","year":"1998","journal-title":"Phytochemistry"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1080\/21501203.2010.529583","article-title":"Secondary metabolites from Phomopsis sp. A123","volume":"1","author":"Li","year":"2010","journal-title":"Mycology"}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/11\/11\/4510\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:50:34Z","timestamp":1760219434000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/11\/11\/4510"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,11,12]]},"references-count":42,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2013,11]]}},"alternative-id":["md11114510"],"URL":"https:\/\/doi.org\/10.3390\/md11114510","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,11,12]]}}}