{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,28]],"date-time":"2026-04-28T19:13:24Z","timestamp":1777403604589,"version":"3.51.4"},"reference-count":41,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2025,7,30]],"date-time":"2025-07-30T00:00:00Z","timestamp":1753833600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002631","name":"Gachon University","doi-asserted-by":"publisher","award":["2021(GCU- 202109950001)"],"award-info":[{"award-number":["2021(GCU- 202109950001)"]}],"id":[{"id":"10.13039\/501100002631","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002631","name":"Gachon University","doi-asserted-by":"publisher","award":["KHU-20241075"],"award-info":[{"award-number":["KHU-20241075"]}],"id":[{"id":"10.13039\/501100002631","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Kyung Hee University","award":["2021(GCU- 202109950001)"],"award-info":[{"award-number":["2021(GCU- 202109950001)"]}]},{"name":"Kyung Hee University","award":["KHU-20241075"],"award-info":[{"award-number":["KHU-20241075"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Streptomyces sp. AWH31-250, isolated from a tidal mudflat in the Nakdong River estuary in Busan, Republic of Korea, was found to produce two novel p-aminoacetophenone derivatives, mohangic acid H (1) and mohangiol (2). Their planar structures were established by comprehensive 1D and 2D NMR spectroscopy, mass spectrometry, and UV analysis, possessing a shorter carbon-chain with a diene moiety, whereas known mohangic acids A\u2013F bear a longer carbon-chain with a triene moiety. The absolute configurations of the key stereogenic centers were determined via computational DP4+ calculations and bioinformatic analysis of the ketoreductase domain sequence from the biosynthetic gene cluster. Based on the careful gene analysis along with whole-genome sequencing, the first plausible biosynthetic pathway of mohangic acids A\u2013G and mohangiol was proposed. Mohangic acid H (1) and mohangiol (2) displayed moderate inhibitory activity against Candida albicans isocitrate lyase with IC50 values of 21.37 and 21.12 \u00b5g\/mL, respectively.<\/jats:p>","DOI":"10.3390\/md23080307","type":"journal-article","created":{"date-parts":[[2025,7,30]],"date-time":"2025-07-30T07:37:23Z","timestamp":1753861043000},"page":"307","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Mohangic Acid H and Mohangiol: New p-Aminoacetophenone Derivatives from a Mudflat-Derived Streptomyces sp."],"prefix":"10.3390","volume":"23","author":[{"given":"Juwan","family":"Son","sequence":"first","affiliation":[{"name":"College of Pharmacy, Gachon University, Incheon 21936, Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ju Heon","family":"Lee","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Gachon University, Incheon 21936, Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yong-Joon","family":"Cho","sequence":"additional","affiliation":[{"name":"Department of Molecular Bioscience, Kangwon National University, Chuncheon 24341, Republic of Korea"},{"name":"Multidimensional Genomics Research Center, Kangwon National University, Chuncheon 24341, Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1287-3514","authenticated-orcid":false,"given":"Kyuho","family":"Moon","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Kyung Hee University, Seoul 02447, Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7771-7320","authenticated-orcid":false,"given":"Munhyung","family":"Bae","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Gachon University, Incheon 21936, Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Jose, P.A., and Jha, B. (2017). Intertidal Marine Sediment Harbours Actinobacteria with Promising Bioactive and Biosynthetic Potential. Sci. Rep., 7.","DOI":"10.1038\/s41598-017-09672-6"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Ryu, D., Hillman, P.F., Akinniyi, G., Nam, S.-J., and Yang, I. (2023). Marine Mudflat Actinomycetes as a Novel Natural Products Source. Front. Mar. Sci., 10.","DOI":"10.3389\/fmars.2023.1297446"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"418","DOI":"10.3390\/microbiolres13030031","article-title":"Streptomyces: Still the Biggest Producer of New Natural Secondary Metabolites, a Current Perspective","volume":"13","author":"Donald","year":"2022","journal-title":"Microbiol. Res."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1362","DOI":"10.1039\/b817069j","article-title":"Genomic Basis for Natural Product Biosynthetic Diversity in the Actinomycetes","volume":"26","author":"Nett","year":"2009","journal-title":"Nat. Prod. Rep."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Chen, J., Zhang, P., Ye, X., Wei, B., Emam, M., Zhang, H., and Wang, H. (2020). The Structural Diversity of Marine Microbial Secondary Metabolites Based on Co-Culture Strategy: 2009\u20132019. Mar. Drugs, 18.","DOI":"10.3390\/md18090449"},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Srinivasan, R., Kannappan, A., Shi, C., and Lin, X. (2021). Marine Bacterial Secondary Metabolites: A Treasure House for Structurally Unique and Effective Antimicrobial Compounds. Mar. Drugs, 19.","DOI":"10.3390\/md19100530"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Jeong, H., Jo, S.J., Bae, M., Kim, Y.R., and Moon, K. (2022). Actinoflavosides B-D, Flavonoid Type Glycosides from Tidal Mudflat-Derived Actinomyces. Mar. Drugs, 20.","DOI":"10.3390\/md20090565"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5187","DOI":"10.3390\/md13085187","article-title":"Hormaomycins B and C: New Antibiotic Cyclic Depsipeptides from a Marine Mudflat-Derived Streptomyces sp.","volume":"13","author":"Bae","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"712","DOI":"10.1021\/ol5037248","article-title":"Mohangamides A and B, New Dilactone-Tethered Pseudo-Dimeric Peptides Inhibiting Candida albicans Isocitrate Lyase","volume":"17","author":"Bae","year":"2015","journal-title":"Org. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1999","DOI":"10.1021\/acs.orglett.8b00546","article-title":"WS9326H, an Antiangiogenic Pyrazolone-Bearing Peptide from an Intertidal Mudflat Actinomycete","volume":"20","author":"Bae","year":"2018","journal-title":"Org. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"332","DOI":"10.1021\/acs.jnatprod.5b00956","article-title":"Mohangic Acids A\u2013E, p-Aminoacetophenonic Acids from a Marine-Mudflat-Derived Streptomyces Sp.","volume":"79","author":"Bae","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"206","DOI":"10.1080\/14786419.2022.2112578","article-title":"Two New Mohangic Acid Derivatives from the Deep-Sea Bacteria Alcanivorax dieselolei BC-5","volume":"38","author":"Zhao","year":"2024","journal-title":"Nat. Prod. Res."},{"key":"ref_13","first-page":"219","article-title":"Candicidin and Other Polyenic Antifungal Antibiotics","volume":"33","author":"Waksman","year":"1965","journal-title":"Bull. World Health Organ."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"8544","DOI":"10.1021\/acs.joc.1c00987","article-title":"Sensitivity Analysis of DP4+ with the Probability Distribution Terms: Development of a Universal and Customizable Method","volume":"86","author":"Zanardi","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"W32","DOI":"10.1093\/nar\/gkaf334","article-title":"antiSMASH 8.0: Extended Gene Cluster Detection Capabilities and Analyses of Chemistry, Enzymology, and Regulation","volume":"53","author":"Blin","year":"2025","journal-title":"Nucleic Acids Res."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1007\/s00253-002-1163-9","article-title":"Candicidin Biosynthesis in Streptomyces griseus","volume":"60","author":"Gil","year":"2003","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1099\/00221287-148-1-51","article-title":"The candicidin gene cluster from Streptomyces griseus IMRU 3570","volume":"148","author":"Campelo","year":"2002","journal-title":"Microbiology"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1065","DOI":"10.1016\/j.chembiol.2003.10.007","article-title":"Organizational and Mutational Analysis of a Complete FR-008\/Candicidin Gene Cluster Encoding a Structurally Related Polyene Complex","volume":"10","author":"Chen","year":"2003","journal-title":"Chem. Biol."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"422","DOI":"10.1039\/c2mb25464f","article-title":"In Vivo Investigation of the Substrate Recognition Capability and Activity Affecting Amino Acid Residues of Glycosyltransferase FscMI in the Biosynthesis of Candicidin","volume":"9","author":"Lei","year":"2013","journal-title":"Mol. Biosyst."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/0378-1119(90)90139-I","article-title":"Phosphate Control of pabS Gene Transcription during Candicidin Biosynthesis","volume":"93","author":"Asturias","year":"1990","journal-title":"Gene"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1778","DOI":"10.1128\/AEM.00859-08","article-title":"Tailoring the P450 Monooxygenase Gene for FR-008\/Candicidin Biosynthesis","volume":"75","author":"Chen","year":"2009","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3895","DOI":"10.1007\/s00018-008-8588-y","article-title":"Medium- and Short-Chain Dehydrogenase\/Reductase Gene and Protein Families","volume":"65","author":"Kavanagh","year":"2008","journal-title":"Cell. Mol. Life Sci."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jmb.2004.04.049","article-title":"Crystal Structure of the Schiff Base Intermediate Prior to Decarboxylation in the Catalytic Cycle of Aspartate \u03b1-Decarboxylase","volume":"340","author":"Lee","year":"2004","journal-title":"J. Mol. Biol."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Liang, C., Nie, Y., Mu, X., and Xu, Y. (2018). Gene Mining-Based Identification of Aldo\u2013Keto Reductases for Highly Stereoselective Reduction of Bulky Ketones. Bioresour. Bioprocess., 5.","DOI":"10.1186\/s40643-018-0220-x"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1151","DOI":"10.1111\/mmi.12156","article-title":"The Transcriptional Regulator TamR from Streptomyces coelicolor Controls a Key Step in Central Metabolism during Oxidative Stress","volume":"87","author":"Huang","year":"2013","journal-title":"Mol. Microbiol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"e00090-19","DOI":"10.1128\/MMBR.00090-19","article-title":"Small-Molecule Acetylation by GCN5-Related N-Acetyltransferases in Bacteria","volume":"84","author":"Burckhardt","year":"2020","journal-title":"Microbiol. Mol. Biol. Rev."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"654","DOI":"10.1002\/cbic.200300581","article-title":"Conserved Amino Acid Residues Correlating With Ketoreductase Stereospecificity in Modular Polyketide Synthases","volume":"4","author":"Caffrey","year":"2003","journal-title":"ChemBioChem"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"898","DOI":"10.1016\/j.chembiol.2007.07.009","article-title":"A Tylosin Ketoreductase Reveals How Chirality Is Determined in Polyketides","volume":"14","year":"2007","journal-title":"Chem. Biol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1476","DOI":"10.3762\/bjoc.20.131","article-title":"Bioinformatic Prediction of the Stereoselectivity of Modular Polyketide Synthase: An Update of the Sequence Motifs in Ketoreductase Domain","volume":"20","author":"Xiang","year":"2024","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3416","DOI":"10.1021\/acs.orglett.2c01285","article-title":"Synthesis of the Proposed Structure of Mohangic Acid C","volume":"24","author":"Takahashi","year":"2022","journal-title":"Org. Lett."},{"key":"ref_31","first-page":"701","article-title":"Apparent Isocitrate Lyase Activity in Leishmania amazonensis","volume":"62","author":"Maimone","year":"2017","journal-title":"Acta. Parasitol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"453","DOI":"10.5530\/ijper.20255143","article-title":"Deciphering Molecular Insights into Isocitrate Lyase and Their Inhibitors: A Detailed Display through Medicinal Chemistry Window","volume":"59","author":"Khanojia","year":"2025","journal-title":"Indian J. Pharm. Educ. Res."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"488","DOI":"10.1107\/S0907444997002680","article-title":"Isocitrate Lyase from Aspergillus nidulans: Crystallization and X-Ray Analysis of a Glyoxylate Cycle Enzyme","volume":"53","author":"Langridge","year":"1997","journal-title":"Acta Crystallogr. D"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1008","DOI":"10.1016\/j.drudis.2017.04.012","article-title":"Targeting Isocitrate Lyase for the Treatment of Latent Tuberculosis","volume":"22","author":"Bhusal","year":"2017","journal-title":"Drug Discov. Today"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"Pdb.prot107852","DOI":"10.1101\/pdb.prot107852","article-title":"Preparing Plasmid DNA from Bacteria","volume":"2022","author":"Bossi","year":"2022","journal-title":"Cold Spring Harb. Protoc."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Wick, R.R., Judd, L.M., Gorrie, C.L., and Holt, K.E. (2017). Unicycler: Resolving Bacterial Genome Assemblies from Short and Long Sequencing Reads. PLoS Comput. Biol., 13.","DOI":"10.1371\/journal.pcbi.1005595"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2068","DOI":"10.1093\/bioinformatics\/btu153","article-title":"Prokka: Rapid Prokaryotic Genome Annotation","volume":"30","author":"Seemann","year":"2014","journal-title":"Bioinformatics"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"D678","DOI":"10.1093\/nar\/gkae1115","article-title":"MIBiG 4.0: Advancing Biosynthetic Gene Cluster Curation through Global Collaboration","volume":"53","author":"Zdouc","year":"2025","journal-title":"Nucleic Acids Res."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Kumar, S., Stecher, G., Suleski, M., Sanderford, M., Sharma, S., and Tamura, K. (2024). MEGA12: Molecular Evolutionary Genetic Analysis Version 12 for Adaptive and Green Computing. Mol. Biol. Evol., 41.","DOI":"10.1093\/molbev\/msae263"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Edgar, R.C. (2004). MUSCLE: A Multiple Sequence Alignment Method with Reduced Time and Space Complexity. BMC Bioinform., 5.","DOI":"10.1186\/1471-2105-5-113"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1188","DOI":"10.1101\/gr.849004","article-title":"WebLogo: A Sequence Logo Generator","volume":"14","author":"Crooks","year":"2004","journal-title":"Genome Res."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/23\/8\/307\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T18:18:36Z","timestamp":1760033916000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/23\/8\/307"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,30]]},"references-count":41,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2025,8]]}},"alternative-id":["md23080307"],"URL":"https:\/\/doi.org\/10.3390\/md23080307","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,30]]}}}