{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:16:54Z","timestamp":1791245814136,"version":"4.1.0"},"reference-count":36,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2024,6,16]],"date-time":"2024-06-16T00:00:00Z","timestamp":1718496000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Guangxi Key Laboratory of Beibu Gulf Marine Resources, Environment and Sustainable Development","award":["MRESD-2023-C02"],"award-info":[{"award-number":["MRESD-2023-C02"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["JoF"],"abstract":"<jats:p>Two new polyketide derivatives, penirubenones A and B (1 and 2), and two naturally rare amino-bis-tetrahydrofuran derivatives, penirubenamides A and B (3 and 4), together with nine known compounds (5\u201313) were isolated from the marine-derived fungus Penicillium rubens BTBU20213035. The structures were identified by HRESIMS and 1D and 2D NMR analyses, and their absolute configurations were determined by a comparison of experimental and calculated electronic circular dichroism (ECD) spectroscopy and 13C NMR data. We found that 6 exhibited antibacterial activity against Staphylococcus aureus, with an MIC value of 3.125 \u03bcg\/mL, and 1 and 2 showed synergistic antifungal activity against Candida albicans at 12.5 and 50 \u03bcg\/mL with 0.0625 \u03bcg\/mL rapamycin.<\/jats:p>","DOI":"10.3390\/jof10060424","type":"journal-article","created":{"date-parts":[[2024,6,17]],"date-time":"2024-06-17T08:48:31Z","timestamp":1718614111000},"page":"424","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Secondary Metabolites from Marine-Derived Fungus Penicillium rubens BTBU20213035"],"prefix":"10.3390","volume":"10","author":[{"given":"Xiuli","family":"Xu","sequence":"first","affiliation":[{"name":"Key Laboratory of Marine Mineral Resources and Polar Geology, Ministry of Education, School of Ocean Sciences, China University of Geosciences, Beijing 100083, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yifei","family":"Dong","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health, Ministry of Education of China, School of Light Industry Science and Engineering, Beijing Technology and Business University, Beijing 100048, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinpeng","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Mineral Resources and Polar Geology, Ministry of Education, School of Ocean Sciences, China University of Geosciences, Beijing 100083, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6774-6999","authenticated-orcid":false,"given":"Long","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Linlin","family":"Ma","sequence":"additional","affiliation":[{"name":"Griffith Institute for Drug Discovery, School of Environment and Science, Griffith University, Brisbane 4111, Australia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9162-3355","authenticated-orcid":false,"given":"Fuhang","family":"Song","sequence":"additional","affiliation":[{"name":"Key Laboratory of Geriatric Nutrition and Health, Ministry of Education of China, School of Light Industry Science and Engineering, Beijing Technology and Business University, Beijing 100048, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoli","family":"Ma","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, North Minzu University, Yinchuan 750021, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,6,16]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1128\/CMR.00029-06","article-title":"Epidemiology of invasive candidiasis: A persistent public health problem","volume":"20","author":"Pfaller","year":"2007","journal-title":"Clin. Microbiol. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"S79","DOI":"10.1093\/ofid\/ofy358","article-title":"Twenty years of the SENTRY Antifungal Surveillance Program: Results for Candida species from 1997\u20132016","volume":"6","author":"Pfaller","year":"2019","journal-title":"Open Forum Infect Dis."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1086\/421946","article-title":"Nosocomial bloodstream infections in US hospitals: Analysis of 24,179 cases from a prospective nationwide surveillance study","volume":"39","author":"Wisplinghoff","year":"2004","journal-title":"Clin. Infect. Dis."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Murphy, S.E., and Bicanic, T. (2021). Drug resistance and novel therapeutic approaches in invasive candidiasis. Front. Cell Infect. Microbiol., 11.","DOI":"10.3389\/fcimb.2021.759408"},{"key":"ref_5","first-page":"e01719","article-title":"The future of antifungal drug therapy: Novel compounds and targets","volume":"65","author":"Dasilva","year":"2021","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"165rv113","DOI":"10.1126\/scitranslmed.3004404","article-title":"Hidden killers: Human fungal infections","volume":"4","author":"Brown","year":"2012","journal-title":"Sci. Transl. Med."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"739","DOI":"10.1126\/science.aap7999","article-title":"Worldwide emergence of resistance to antifungal drugs challenges human health and food security","volume":"360","author":"Fisher","year":"2018","journal-title":"Science"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3390","DOI":"10.1021\/acs.chemrev.0c00199","article-title":"Antifungal drug resistance: Molecular mechanisms in and beyond","volume":"121","author":"Lee","year":"2021","journal-title":"Chem. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Bezerra, L.P., Freitas, C.D.T., Silva, A.F.B., Amaral, J.L., Neto, N.A.S., Silva, R.G.G., Parra, A.L.C., Goldman, G.H., Oliveira, J.T.A., and Mesquita, F.P. (2022). Synergistic antifungal activity of synthetic peptides and antifungal drugs against Candida albicans and C. parapsilosis biofilms. Antibiotics, 11.","DOI":"10.3390\/antibiotics11050553"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Maione, A., La Pietra, A., de Alteriis, E., Mileo, A., De Falco, M., Guida, M., and Galdiero, E. (2022). Effect of myrtenol and its synergistic interactions with antimicrobial drugs in the inhibition of single and mixed biofilms of Candida auris and Klebsiella pneumoniae. Microorganisms, 10.","DOI":"10.3390\/microorganisms10091773"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Aldholmi, M., Marchand, P., Ourliac-Garnier, I., Le Pape, P., and Ganesan, A. (2019). A decade of antifungal leads from natural products: 2010\u20132019. Pharmaceuticals, 12.","DOI":"10.3390\/ph12040182"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Cardoso, J., Nakayama, D.G., Sousa, E., and Pinto, E. (2020). Marine-derived compounds and prospects for their antifungal application. Molecules, 25.","DOI":"10.3390\/molecules25245856"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"631","DOI":"10.1016\/j.ejmech.2016.11.022","article-title":"Antifungal potential of marine natural products","volume":"126","author":"Cheng","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1122","DOI":"10.1039\/D1NP00076D","article-title":"Marine natural products","volume":"39","author":"Carroll","year":"2022","journal-title":"Nat. Prod. Rep."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1039\/D2NP00083K","article-title":"Marine natural products","volume":"40","author":"Carroll","year":"2023","journal-title":"Nat. Prod. Rep."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Liu, S., Su, M., Song, S.J., and Jung, J.H. (2017). Marine-derived Penicillium species as producers of cytotoxic metabolites. Mar. Drugs, 15.","DOI":"10.3390\/md15100329"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1080\/10286020.2015.1127230","article-title":"Marine natural products sourced from marine-derived fungi","volume":"18","author":"Ma","year":"2016","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2000","DOI":"10.2174\/1389557521666210217093517","article-title":"Origins, structures, and bioactivities of secondary metabolites from marine-derived Penicillium Fungi","volume":"21","author":"Yang","year":"2021","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Song, F., Dong, Y., Wei, S., Zhang, X., Zhang, K., and Xu, X. (2022). New antibacterial secondary metabolites from a marine-derived Talaromyces sp. Strain BTBU20213036. Antibiotics, 11.","DOI":"10.3390\/antibiotics11020222"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Zhang, K., Zhang, X., Lin, R., Yang, H., Song, F., Xu, X., and Wang, L. (2022). New secondary metabolites from the marine-derived fungus Talaromyces mangshanicus BTBU20211089. Mar. Drugs, 20.","DOI":"10.3390\/md20020079"},{"key":"ref_21","first-page":"958","article-title":"Two New trienoic acid derivatives from marine-derived fungus Penicillium oxalicum BTBU20213011","volume":"17","author":"Liu","year":"2023","journal-title":"Rec. Nat. Prod."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2947","DOI":"10.1093\/bioinformatics\/btm404","article-title":"Clustal W and clustal X version 2.0","volume":"23","author":"Larkin","year":"2007","journal-title":"Bioinformatics"},{"key":"ref_23","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 A.03, Gaussian, Inc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"8251","DOI":"10.1021\/ja00179a005","article-title":"Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations","volume":"112","author":"Wolinski","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"4805","DOI":"10.1002\/ejoc.201402372","article-title":"Structure determination of pentacyclic pyridoacridine alkaloids from the Australian marine organisms Ancorina geodides and Cnemidocarpa stolonifera","volume":"2014","author":"Tran","year":"2014","journal-title":"Eur. J. Org. Chem."},{"key":"ref_26","unstructured":"CLSI (2008). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, Clinical and Laboratory Standards Institute. [7th ed.]. approved standard."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Han, J., Wang, H., Zhang, R., Dai, H., Chen, B., Wang, T., Sun, J., Wang, W., Song, F., and Li, E. (2022). Cyclic tetrapeptides with synergistic antifungal activity from the fungus Aspergillus westerdijkiae using LC-MS\/MS-based molecular networking. Antibiotics, 11.","DOI":"10.3390\/antibiotics11020166"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1021\/np800733y","article-title":"Ambuic acid and torreyanic acid derivatives from the endolichenic Fungus Pestalotiopsis sp.","volume":"72","author":"Ding","year":"2009","journal-title":"J. Nat. Prod."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3457","DOI":"10.1039\/c2cc18172j","article-title":"Enantioselective synthesis of (-)-paeonilide","volume":"48","author":"Harrar","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Ren, J., Huo, R., Liu, G., and Liu, L. (2021). New andrastin-Type meroterpenoids from the marine-derived fungus Penicillium sp.. Mar. Drugs, 19.","DOI":"10.3390\/md19040189"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2630","DOI":"10.1021\/acs.jnatprod.1c00264","article-title":"Insights into ergochromes of the plant pathogen Claviceps purpurea","volume":"84","author":"Lunne","year":"2021","journal-title":"J. Nat. Prod."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"296","DOI":"10.1021\/acs.orglett.5b03465","article-title":"Cytochrome P450 for citreohybridonol synthesis: Oxidative derivatization of the andrastin scaffold","volume":"18","author":"Matsuda","year":"2016","journal-title":"Org. Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.fitote.2018.12.022","article-title":"Two new meroterpenoids and two new monoterpenoids from the deep sea-derived fungus Penicillium sp. YPGA11","volume":"133","author":"Cheng","year":"2019","journal-title":"Fitoterapia"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"840","DOI":"10.1080\/14786419.2017.1311893","article-title":"Isolation and X-ray structure analysis of citreohybridonol from marine-derived Penicillium atrovenetum","volume":"32","author":"Ebrahim","year":"2018","journal-title":"Nat. Prod. Res."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2699","DOI":"10.1021\/acs.jnatprod.5b00655","article-title":"Penicyclones A-E, antibacterial polyketides from the deep-sea-derived fungus Penicillium sp. F23-2","volume":"78","author":"Guo","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1080\/14786419.2015.1034712","article-title":"A new polyoxygenated farnesylcyclohexenone from fungus Penicillium sp.","volume":"30","author":"Yang","year":"2016","journal-title":"Nat. Prod. Res."}],"container-title":["Journal of Fungi"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2309-608X\/10\/6\/424\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:59:35Z","timestamp":1760108375000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2309-608X\/10\/6\/424"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,6,16]]},"references-count":36,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2024,6]]}},"alternative-id":["jof10060424"],"URL":"https:\/\/doi.org\/10.3390\/jof10060424","relation":{},"ISSN":["2309-608X"],"issn-type":[{"value":"2309-608X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,6,16]]}}}