{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,8]],"date-time":"2026-01-08T23:18:37Z","timestamp":1767914317417,"version":"3.49.0"},"reference-count":39,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2022,1,25]],"date-time":"2022-01-25T00:00:00Z","timestamp":1643068800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003725","name":"National Research Foundation of Korea","doi-asserted-by":"publisher","award":["2019R1A5A2027340 and 2021R1A2C2007937"],"award-info":[{"award-number":["2019R1A5A2027340 and 2021R1A2C2007937"]}],"id":[{"id":"10.13039\/501100003725","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceuticals"],"abstract":"<jats:p>As part of ongoing systematic research into the discovery of bioactive secondary metabolites with novel structures from Korean wild mushrooms, we investigated secondary metabolites from a poisonous mushroom, Omphalotus japonicus (Kawam.) Kirchm. &amp; O. K. Mill. belonging to the family Marasmiaceae, which causes nausea and vomiting after consumption. The methanolic extract of O. japonicus fruiting bodies was subjected to the fractionation by solvent partition, and the CH2Cl2 fraction was analyzed for the isolation of bioactive compounds, aided by an untargeted liquid chromatography mass spectrometry (LC\u2013MS)-based analysis. Through chemical analysis, five fatty acid derivatives (1\u20135), including two new fatty acid derivatives, omphalotols A and B (1 and 2), were isolated from the CH2Cl2 fraction, and the chemical structures of the new compounds were determined using 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and high resolution electrospray ionization mass spectrometry (HR-ESIMS), as well as fragmentation patterns in MS\/MS data and chemical reactions followed by the application of Snatzke\u2019s method and competing enantioselective acylation (CEA). In the anti-Helicobacter pylori activity test, compound 1 showed moderate antibacterial activity against H. pylori strain 51 with 27.4% inhibition, comparable to that of quercetin as a positive control. Specifically, compound 3 exhibited the most significant antibacterial activity against H. pylori strain 51, with MIC50 and MIC90 values of 9 and 20 \u03bcM, respectively, which is stronger inhibitory activity than that of another positive control, metronidazole (MIC50 = 17 \u03bcM and MIC90 = 46 \u03bcM). These findings suggested the experimental evidence that the compound 3, an \u03b1,\u03b2-unsaturated ketone derivative, could be used as a moiety in the development of novel antibiotics against H. pylori.<\/jats:p>","DOI":"10.3390\/ph15020139","type":"journal-article","created":{"date-parts":[[2022,1,25]],"date-time":"2022-01-25T21:07:11Z","timestamp":1643144831000},"page":"139","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Two New Fatty Acid Derivatives, Omphalotols A and B and Anti-Helicobacter pylori Fatty Acid Derivatives from Poisonous Mushroom Omphalotus japonicus"],"prefix":"10.3390","volume":"15","author":[{"given":"Seulah","family":"Lee","sequence":"first","affiliation":[{"name":"School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea"},{"name":"Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon 21990, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tae Wan","family":"Kim","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yong Hoon","family":"Lee","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3190-792X","authenticated-orcid":false,"given":"Dong-Min","family":"Kang","sequence":"additional","affiliation":[{"name":"College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University, Jinju 52828, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rhim","family":"Ryoo","sequence":"additional","affiliation":[{"name":"Special Forest Products Division, Forest Bioresources Department, National Institute of Forest Science, Suwon 16631, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoon-Joo","family":"Ko","sequence":"additional","affiliation":[{"name":"Laboratory of Nuclear Magnetic Resonance, National Center for Inter-University Research Facilities (NCIRF), Seoul National University, Gwanak-gu, Seoul 08826, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1201-0746","authenticated-orcid":false,"given":"Mi-Jeong","family":"Ahn","sequence":"additional","affiliation":[{"name":"College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University, Jinju 52828, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5285-9138","authenticated-orcid":false,"given":"Ki Hyun","family":"Kim","sequence":"additional","affiliation":[{"name":"School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,1,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s13205-011-0036-2","article-title":"Recent Developments in Mushrooms as Anti-Cancer Therapeutics: A Review","volume":"2","author":"Patel","year":"2012","journal-title":"3 Biotech"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1323","DOI":"10.1007\/s00253-010-3067-4","article-title":"Current Findings, Future Trends, and Unsolved Problems in Studies of Medicinal Mushrooms","volume":"89","author":"Wasser","year":"2011","journal-title":"Appl. Microbiol. Biotech."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"357","DOI":"10.4103\/2319-4170.143502","article-title":"Biomedical Effects of Mushrooms with Emphasis on Pure Compounds","volume":"37","author":"Paterson","year":"2014","journal-title":"Biomed. J."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"214","DOI":"10.1007\/s12272-020-01213-6","article-title":"Trichothecene and Tremulane Sesquiterpenes from a Hallucinogenic Mushroom Gymnopilus junonius and Their Cytotoxicity","volume":"43","author":"Lee","year":"2020","journal-title":"Arch. Pharm. Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"3489","DOI":"10.1021\/acs.jnatprod.9b00782","article-title":"Pantheric Acids a\u2013C from a Poisonous Mushroom, Amanita pantherina, Promote Lipid Accumulation in Adipocytes","volume":"82","author":"Lee","year":"2019","journal-title":"J. Nat. Prod."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2737","DOI":"10.1021\/acs.jnatprod.0c00673","article-title":"Calvatianone, a Sterol Possessing a 6\/5\/6\/5-Fused Ring System with a Contracted Tetrahydrofuran B-Ring, from the Fruiting Bodies of Calvatia nipponica","volume":"83","author":"Lee","year":"2020","journal-title":"J. Nat. Prod."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1364","DOI":"10.1093\/bbb\/zbab063","article-title":"Omphaloprenol A: A New Bioactive Polyisoprenepolyol Isolated from the Mycelium of Poisonous Mushroom Omphalotus japonicus","volume":"85","author":"Aoki","year":"2021","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"789","DOI":"10.2116\/analsci.19P053","article-title":"Application of High-Speed Countercurrent Chromatography for the Purification of High-Purity Illudin S from Omphalotus japonicus","volume":"35","author":"Uto","year":"2019","journal-title":"Anal. Sci."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1016\/0006-2952(94)90113-9","article-title":"Characterization of Illudin S Sensitivity in DNA Repair-Deficient Chinese Hamster Cells: Unusually High Sensitivity of Ercc2 and Ercc3 DNA Helicase-Deficient Mutants in Comparison to Other Chemotherapeutic Agents","volume":"48","author":"Kelner","year":"1994","journal-title":"Biochem. Pharmacol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1007\/s002800050627","article-title":"Characterization of Cellular Accumulation and Toxicity of Illudin S in Sensitive and Nonsensitive Tumor Cells","volume":"40","author":"Kelner","year":"1997","journal-title":"Cancer Chemother. Pharmacol."},{"key":"ref_11","first-page":"1517","article-title":"Irofulven (Mgi Pharma)","volume":"3","author":"Baekelandt","year":"2002","journal-title":"Curr. Opin. Investig. Drugs"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1023\/A:1020649827173","article-title":"Irofulven, a Novel Inhibitor of DNA Synthesis, in Metastatic Renal Cell Cancer","volume":"20","author":"Amato","year":"2002","journal-title":"Investig. New Drugs"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1013","DOI":"10.1039\/b904720d","article-title":"Profiling Patterns of Glutathione Reductase Inhibition by the Natural Product Illudin S and Its Acylfulvene Analogues","volume":"5","author":"Liu","year":"2009","journal-title":"Mol. Biosyst."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1021\/tx300430r","article-title":"Quantification of Acylfulvene\u2013and Illudin S\u2013DNA Adducts in Cells with Variable Bioactivation Capacities","volume":"26","author":"Pietsch","year":"2013","journal-title":"Chem. Res. Toxicol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3965","DOI":"10.1016\/S0040-4039(01)88588-9","article-title":"Dihydroilludin S, a New Constituent from Lampteromyces japonicus","volume":"10","author":"Ichihara","year":"1969","journal-title":"Tetrahedron Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1113","DOI":"10.1246\/cl.1999.1113","article-title":"Neoilludins a and B, New Bioactive Components from Lampteromyces japonicus","volume":"28","author":"Kuramoto","year":"1999","journal-title":"Chem. Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"454","DOI":"10.1016\/0045-2068(89)90046-1","article-title":"Lampteromyces Bioluminescence: 3. Structure of Lampteroflavin, the Light Emitter in the Luminous Mushroom, L. japonicus","volume":"17","author":"Uyakul","year":"1989","journal-title":"Bioorg. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"292","DOI":"10.1038\/197292a0","article-title":"Isolation of Lampterol, an Antitumour Substance from Lampteromyces japonicus","volume":"197","author":"Nakanishi","year":"1963","journal-title":"Nature"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1955","DOI":"10.1248\/cpb.23.1955","article-title":"The Polysaccharide from Lampteromyces japonicus","volume":"23","author":"Fukuda","year":"1975","journal-title":"Chem. Pharm. Bull."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2051","DOI":"10.5012\/bkcs.2010.31.7.2051","article-title":"Anti-Melanogenic Fatty Acid Derivatives from the Tuber-Barks of Colocasia antiquorum var. esculenta","volume":"31","author":"Kim","year":"2010","journal-title":"Bull. Korean Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"13212","DOI":"10.1021\/acs.analchem.8b03385","article-title":"Highly Sensitive, Simple, and Cost-and Time-Effective Method to Determine the Absolute Configuration of a Secondary Alcohol Using Competing Enantioselective Acylation Coupled with LC\/MS","volume":"90","author":"Lee","year":"2018","journal-title":"Anal. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4819","DOI":"10.1021\/jo010136v","article-title":"Determination of Absolute Configuration of Acyclic 1, 2-Diols with Mo2(Oac)4.1. Snatzke\u2019s Method Revisited","volume":"66","author":"Pescitelli","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"394","DOI":"10.1021\/np3007588","article-title":"Bioactive Flavaglines and Other Constituents Isolated from Aglaia perviridis","volume":"76","author":"Pan","year":"2013","journal-title":"J. Nat. Prod."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"7227","DOI":"10.1021\/jo00103a012","article-title":"Structure and Stereochemistry of Constanolactones Ag, Lactonized Cyclopropyl Oxylipins from the Red Marine Alga Constantinea simplex","volume":"59","author":"Nagle","year":"1994","journal-title":"J. Org. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1577","DOI":"10.6023\/cjoc201701016","article-title":"Four New 2, 5-Disubstituted Furan Vicinal Diols from the Fungus Ceriporia alachuana","volume":"37","author":"Liangyan","year":"2017","journal-title":"Chin. J. Org. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1021\/np50050a036","article-title":"Plant Anticancer Agents, Xliii.(E, E)-7, 12-Dioxo-Octadeca-8, 10-Dien-1-Oic Acid (Ostopanic Acid), a Cytotoxic Fatty Acid from Ostodes paniculata","volume":"50","author":"Hamburger","year":"1987","journal-title":"J. Nat. Prod."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"7624","DOI":"10.1016\/j.tet.2007.05.047","article-title":"Enantioselective Syntheses of (\u2212)-Pinellic Acid, A-and \u0392-Dimorphecolic Acid","volume":"63","author":"Naidu","year":"2007","journal-title":"Tetrahedron"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3364","DOI":"10.1016\/j.tet.2009.02.063","article-title":"A Concise Synthesis of Pinellic Acid Using a Cross-Metathesis Approach","volume":"65","author":"Miura","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2897","DOI":"10.1128\/AAC.00016-11","article-title":"Cholesterol Enhances Helicobacter Pylori Resistance to Antibiotics and Ll-37","volume":"55","author":"McGee","year":"2011","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1808","DOI":"10.1111\/j.1572-0241.2007.01393.x","article-title":"Practice Parameters Committee of the American College of Gastroenterology. American College of Gastroenterology Guideline on the Management of Helicobacter Pylori Infection","volume":"102","author":"Chey","year":"2007","journal-title":"Off. J. Am. Coll. Gastroenterol.|ACG"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"528","DOI":"10.1016\/S0369-8114(01)00209-7","article-title":"Clarithromycin resistance of Helicobacter pylori has a major impact on the efficacy of the omeprazole-amoxicillin-clarithromycin therapy","volume":"49","author":"Tankovic","year":"2001","journal-title":"Pathol. Biol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"704721","DOI":"10.1093\/ecam\/nep147","article-title":"In vitro activity of 2-methoxy-1,4-naphthoquinone and stigmasta-7,22-diene-3b-ol from Impatiens balsamina L. against multiple antibiotic-resistant Helicobacter pylori","volume":"2011","author":"Wang","year":"2011","journal-title":"Evid. Based. Complement. Altern. Med."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"415","DOI":"10.3343\/alm.2013.33.6.415","article-title":"Antibiotic resistance in Helicobacter pylori strains and its effect on H. pylori eradication rates in a single center in Korea","volume":"33","author":"An","year":"2013","journal-title":"Ann. Lab. Med."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2373","DOI":"10.1007\/s10620-016-4091-8","article-title":"Helicobacter pylori clarithromycin resistance and treatment failure are common in the USA","volume":"61","author":"Park","year":"2016","journal-title":"Dig. Dis. Sci."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2985","DOI":"10.1016\/S0024-3205(03)00708-2","article-title":"Urease inhibitory activity of simple \u03b1,\u03b2-unsaturated ketones","volume":"73","author":"Tanaka","year":"2003","journal-title":"Life Sci."},{"key":"ref_36","unstructured":"Gelfand, D.H., Sninsky, J.J., and White, T.J. (1990).  Isolation of DNA from fungal mycelia and single spores. PCR Protocols: A Guide to Methods and Applications, Academic Press."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1111\/j.1365-294X.1993.tb00005.x","article-title":"Its Primers with Enhanced Specificity for Basidiomycetes-Application to the Identification of Mycorrhizae and Rusts","volume":"2","author":"Gardes","year":"1993","journal-title":"Molec. Ecol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"505","DOI":"10.1007\/s12272-019-01160-x","article-title":"A new anti-Helicobacter pylori juglone from Reynoutria japonica","volume":"42","author":"Khalil","year":"2019","journal-title":"Arch. Pharmacal Res."},{"key":"ref_39","unstructured":"Wayne, P. (2008). Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts, Clinical and Laboratory Standards Institute. approved standard; CLSI document M27-A3."}],"container-title":["Pharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8247\/15\/2\/139\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T22:07:32Z","timestamp":1760134052000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8247\/15\/2\/139"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,1,25]]},"references-count":39,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2022,2]]}},"alternative-id":["ph15020139"],"URL":"https:\/\/doi.org\/10.3390\/ph15020139","relation":{},"ISSN":["1424-8247"],"issn-type":[{"value":"1424-8247","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,1,25]]}}}