{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,10]],"date-time":"2026-01-10T22:59:24Z","timestamp":1768085964126,"version":"3.49.0"},"reference-count":26,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2023,2,6]],"date-time":"2023-02-06T00:00:00Z","timestamp":1675641600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["22277147"],"award-info":[{"award-number":["22277147"]}]},{"name":"National Natural Science Foundation of China","award":["21961142008"],"award-info":[{"award-number":["21961142008"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Two unusual polyketide\u2013sesquiterpene metabolites, craterodoratins T (1) and U (2), along with the known compound craterellin A (3), were isolated from the higher fungus Craterellus odoratus. The structures of isolated compounds were characterized based on nuclear magnetic resonance (NMR) and mass spectrum (MS) spectroscopic analysis, while the absolute configuration of the compounds was determined by theoretical NMR and electronic circular dichroism (ECD) calculations. Compound 1 possessed a rare structure with two aromatic groups. Compounds 1 and 3 showed immunosuppressive activity with IC50 values ranging from 5.516 to 19.953 \u03bcM.<\/jats:p>","DOI":"10.3390\/molecules28041564","type":"journal-article","created":{"date-parts":[[2023,2,7]],"date-time":"2023-02-07T01:35:17Z","timestamp":1675733717000},"page":"1564","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Meroterpenoids with Immunosuppressive Activity from Edible Fungus Craterellus odoratus"],"prefix":"10.3390","volume":"28","author":[{"given":"Quan","family":"Dai","sequence":"first","affiliation":[{"name":"School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Li-Ting","family":"Pang","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0208-8232","authenticated-orcid":false,"given":"Fa-Lei","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gang-Qiang","family":"Wang","sequence":"additional","affiliation":[{"name":"Hubei Key Laboratory of Radiation Chemistry and Functional Materials, Non-Power Nuclear Technology Collaborative Innovation Center, School of Nuclear Technology and Chemistry and Biology, Hubei University of Science and Technology, Xianning 437100, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xue-Mei","family":"Li","sequence":"additional","affiliation":[{"name":"Plant Protection and Quarantine Station of Dehong, Dehong 678400, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ji-Kai","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1977-9857","authenticated-orcid":false,"given":"Tao","family":"Feng","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1063","DOI":"10.1039\/b820413f","article-title":"Meroterpenoids produced by fungi","volume":"26","author":"Geris","year":"2009","journal-title":"Nat. Prod. Rep."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Surti, M., Patel, M., Redhwan, A., Al-Keridis, L.A., Adnan, M., Alshammari, N., and Reddy, M.N. (2022). Ilimaquinone (marine sponge metabolite) induces apoptosis in HCT-116 human colorectal carcinoma cells via mitochondrial-mediated apoptosis pathway. Mar. Drugs, 20.","DOI":"10.3390\/md20090582"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Stanojkovic, T.P., Filimonova, M., Grozdanic, N., Petovic, S., Shitova, A., Soldatova, O., Filimonov, A., Vladic, J., Shegay, P., and Kaprin, A. (2022). Evaluation of in vitro cytotoxic potential of avarol towards human cancer cell lines and in vivo antitumor activity in solid tumor models. Molecules, 27.","DOI":"10.3390\/molecules27249048"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"33511","DOI":"10.1021\/acsomega.2c04471","article-title":"Evaluation of derivatives of (+)-puupehenone against Clostridioides difficile and other gram-positive bacteria","volume":"7","author":"Johnstone","year":"2022","journal-title":"ACS Omega"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5014","DOI":"10.1021\/ol901996g","article-title":"Epoxyphomalin A and B, prenylated polyketides with potent cytotoxicity from the marine-derived fungus Phoma sp.","volume":"11","author":"Mohamed","year":"2009","journal-title":"Org. Lett."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"157","DOI":"10.11646\/phytotaxa.346.2.3","article-title":"Two new species of Craterellus (Cantharellaceae) from tropical India","volume":"346","author":"Bijeesh","year":"2018","journal-title":"Phytotaxa"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"35","DOI":"10.11646\/phytotaxa.360.1.3","article-title":"A new yellow species of Craterellus (Cantharellales, Hydnaceae) from China","volume":"360","author":"Zhong","year":"2018","journal-title":"Phytotaxa"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1017\/S0953756299001380","article-title":"Molecular systematics of Craterellus: Cladistic analysis of nuclear LSU rDNA sequence data","volume":"104","author":"Dahlman","year":"2000","journal-title":"Mycol. Res."},{"key":"ref_9","first-page":"A1","article-title":"Nutritional and biochemical analysis of Craterellus odoratus: Rare chanterelle basidiomycetes from similipal biosphere reserve of odisha","volume":"2","author":"Tripathy","year":"2015","journal-title":"Ann. Appl. BioSci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1016\/j.phytochem.2009.09.020","article-title":"Rare merosesquiterpenoids from basidiomycete Craterellus odoratus and their inhibition of 11\u03b2-hydroxysteroid dehydrogenases","volume":"71","author":"Zhang","year":"2010","journal-title":"Phytochemistry"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1080\/10286020.2016.1204298","article-title":"Two new 4,6-dimethyl-3,4-dihydrochromen-2-one derivatives from Craterellus odoratus","volume":"19","author":"Zhang","year":"2017","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1007\/s13659-012-0057-5","article-title":"Five new polyketides from the basidiomycete Craterellus odoratus","volume":"2","author":"Guo","year":"2012","journal-title":"Nat. Prod. Bioprospect."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"950","DOI":"10.1080\/10286020.2012.729508","article-title":"Four new compounds from the basidiomycete Craterellus odoratus","volume":"14","author":"Guo","year":"2012","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Dai, Q., Zhang, F.L., Li, Z.H., He, J., and Feng, T. (2021). Immunosuppressive sesquiterpenoids from the edible mushroom Craterellus odoratus. J. Fungi, 7.","DOI":"10.3390\/jof7121052"},{"key":"ref_15","first-page":"1641","article-title":"Antimycobacterial natural products from endophytes of the medicinal plant Aralia nudicaulis","volume":"10","author":"Li","year":"2015","journal-title":"Nat. Prod. Commun."},{"key":"ref_16","unstructured":"Hehre, W.J. (2003). A Guide to Molecular Mechanics and Quantum Chemical Calculations, Wavefunction, Inc."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3172","DOI":"10.1039\/B517914A","article-title":"Advances in methods and algorithms in a modern quantum chemistry program package","volume":"8","author":"Shao","year":"2006","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_18","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 16, Revision B.01, Gaussian, Inc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"12526","DOI":"10.1021\/acs.joc.5b02396","article-title":"Beyond DP4: An improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts","volume":"80","author":"Grimblat","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1002\/chir.22138","article-title":"SpecDis: Quantifying the comparison of calculated and experimental electronic circular dichroism spectra","volume":"25","author":"Bruhn","year":"2013","journal-title":"Chirality"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Methods"},{"key":"ref_22","first-page":"493","article-title":"A simple method of estimating fifty percent endpoints","volume":"27","author":"Reed","year":"1938","journal-title":"Am. J. Hygiene"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2335","DOI":"10.1021\/acs.orglett.6b00685","article-title":"Meroterpenoids with antiproliferative activity from a Hawaiian-plant associated fungus Peyronellaea coffeae-arabicae FT238","volume":"18","author":"Li","year":"2016","journal-title":"Org. Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1002\/cbdv.201400331","article-title":"Merosesquiterpenoids and ten-membered macrolides from a soft coral-derived Lophiostoma sp. fungus","volume":"12","author":"Zheng","year":"2015","journal-title":"Chem. Biodivers."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"6252","DOI":"10.1016\/j.tetlet.2014.09.075","article-title":"Total synthesis of bioactive drimane\u2013epoxyquinol hybrid natural products: Macrophorin A, 4\u2032-oxomacrophorin A, and 1\u2032-epi-craterellin A","volume":"55","author":"Garai","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_26","unstructured":"Liu, H.W., and Begley, T.P. (2020). Comprehensive Natural Products III, Elsevier."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/4\/1564\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:25:53Z","timestamp":1760120753000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/4\/1564"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,6]]},"references-count":26,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["molecules28041564"],"URL":"https:\/\/doi.org\/10.3390\/molecules28041564","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,6]]}}}