{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T02:57:08Z","timestamp":1784257028053,"version":"3.55.0"},"reference-count":20,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2018,11,23]],"date-time":"2018-11-23T00:00:00Z","timestamp":1542931200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Three new thiodiketopiperazines, geospallins A\u2013C (1\u20133), together with nine known analogues (4\u201312), were isolated from the culture of the deep-sea sediment-derived fungus Geosmithia pallida FS140. Among them, geospallins A and B (1 and 2) represent rare examples of thiodiketopiperazines featuring an S-methyl group at C-10 and a tertiary hydroxyl group at C-11. Their structures were determined by high-resolution electrospray mass spectrometry (HRESIMS), spectroscopic analyses, and electronic circular dichroism (ECD) calculations. Their angiotensin-converting enzyme (ACE) inhibitory activity was reported, and geospallins A\u2013C (1\u20133) showed inhibitory activity with IC50 values of 29\u201335 \u00b5M.<\/jats:p>","DOI":"10.3390\/md16120464","type":"journal-article","created":{"date-parts":[[2018,11,23]],"date-time":"2018-11-23T12:20:28Z","timestamp":1542975628000},"page":"464","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Geospallins A\u2013C: New Thiodiketopiperazines with Inhibitory Activity against Angiotensin-Converting Enzyme from a Deep-Sea-Derived Fungus Geosmithia pallida FS140"],"prefix":"10.3390","volume":"16","author":[{"given":"Zhang-Hua","family":"Sun","sequence":"first","affiliation":[{"name":"State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China"},{"name":"Guangdong Provincial Key Laboratory of New Drug, Development and Research of Chinese Medicine, Mathematical Engineering Academy of Chinese Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiangyong","family":"Gu","sequence":"additional","affiliation":[{"name":"The Second Institute of Clinical Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Ye","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liang-Xi","family":"Wen","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qi-Bin","family":"Lin","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sai-Ni","family":"Li","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu-Chan","family":"Chen","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hao-Hua","family":"Li","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8945-9448","authenticated-orcid":false,"given":"Wei-Min","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,11,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3641","DOI":"10.1021\/cr200398y","article-title":"2,5-Diketopiperazines: Synthesis, reactions, medicinal chemistry, and bioactive natural products","volume":"112","author":"Borthwick","year":"2012","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"382","DOI":"10.1039\/C5NP00156K","article-title":"Marine natural products","volume":"36","author":"Blunt","year":"2016","journal-title":"Nat. Prod. Rep."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"196","DOI":"10.1039\/C005001F","article-title":"Marine natural products","volume":"28","author":"Blunt","year":"2011","journal-title":"Nat. Prod. Rep."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2809","DOI":"10.1002\/cbdv.200900211","article-title":"Diketopiperazines from marine organisms","volume":"7","author":"Huang","year":"2010","journal-title":"Chem. Biodivers."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1038\/nrneph.2018.15","article-title":"Angiotensin-converting enzyme in innate and adaptive immunity","volume":"14","author":"Bernstein","year":"2018","journal-title":"Nat. Rev. Nephrol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1179","DOI":"10.1021\/acs.jnatprod.5b00092","article-title":"Top-down targeted metabolomics teveals a sulfur-containing metabolite with inhibitory activity against angiotensin-converting enzyme in Asparagus officinalis","volume":"78","author":"Nakabayashi","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Xu, J.L., Liu, H.X., Chen, Y.C., Tan, H.B., Guo, H., Xu, L.Q., Li, S.N., Huang, Z.L., Li, H.H., Gao, X.X., and Zhang, W.M. (2018). Highly substituted benzophenone aldehydes and eremophilane derivatives from the deep-sea derived fungus Phomopsis lithocarpus FS508. Mar. Drugs, 16.","DOI":"10.3390\/md16090329"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1792","DOI":"10.1039\/C8QO00095F","article-title":"Lithocarpins A\u2013D: Four tenellone-macrolide conjugated [4 + 2] hetero-adducts from the deep-sea derived fungus Phomopsis lithocarpus FS508","volume":"5","author":"Xu","year":"2018","journal-title":"Org. Chem. Front."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Fan, Z., Sun, Z.-H., Liu, Z., Chen, Y.-C., Liu, H.-X., Li, H.-H., and Zhang, W.M. (2016). Dichotocejpins A\u2013C: New diketopiperazines from a deep-sea-derived fungus Dichotomomyces cejpii FS110. Mar. Drugs, 14.","DOI":"10.3390\/md14090164"},{"key":"ref_10","first-page":"119","article-title":"Biosynthesis of bisdethiobis(methylthio)gliotoxin, a new metabolite of Gliocladium deliquescens","volume":"1","author":"Gordon","year":"1980","journal-title":"J. Chem. Soc. Perk. Trans. 1"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"236","DOI":"10.1007\/s10600-005-0122-y","article-title":"Alkaloids from the marine isolate of the fungus Aspergillus fumigatus","volume":"41","author":"Afiyatullov","year":"2005","journal-title":"Chem. Nat. Compd."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"5657","DOI":"10.3390\/md12115657","article-title":"Exploring the chemodiversity and biological activities of the secondary metabolites from the marine fungus Neosartorya pseudofischeri","volume":"12","author":"Liang","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1021\/np200740e","article-title":"Gliotoxin analogues from a marine-derived fungus, Penicillium sp., and their cytotoxic and histone methyltransferase inhibitory activities","volume":"75","author":"Sun","year":"2012","journal-title":"J. Nat. Prod."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"9678","DOI":"10.1021\/ja2029987","article-title":"Identification of cryptic products of the gliotoxin gene cluster using NMR-based comparative metabolomics and a model for gliotoxin biosynthesis","volume":"133","author":"Forseth","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1021\/ol0507266","article-title":"Unique diketopiperazine dimers from the insect pathogenic fungus Verticillium hemipterigenum BCC 1449","volume":"7","author":"Isaka","year":"2005","journal-title":"Org. Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"953","DOI":"10.1080\/14786410902726134","article-title":"Three new dioxopiperazine metabolites from a marine-derived fungus Aspergillus fumigatus Fres","volume":"24","author":"Zhao","year":"2010","journal-title":"Nat. Prod. Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4949","DOI":"10.3390\/md13084949","article-title":"Epipolythiodiketopiperazines from the marine derived fungus Dichotomomyces cejpii with NF-\u03baB inhibitory potential","volume":"13","author":"Harms","year":"2015","journal-title":"Mar. Drugs"},{"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., Mennucci, B., and Petersson, G.A. (2016). Gaussian 16W, Revision A.03. Gaussian, Inc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5323","DOI":"10.1021\/jf060482j","article-title":"Lactoferricin-related peptides with inhibitory effects on ACE-dependent vasoconstriction","volume":"54","author":"Centeno","year":"2006","journal-title":"J. Agric. Food. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1016\/j.phytochem.2010.11.025","article-title":"Bio-assay guided isolation and identification of \u03b1-glucosidase inhibitors from the leaves of Aquilaria sinensis","volume":"72","author":"Feng","year":"2011","journal-title":"Phytochemistry"}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/16\/12\/464\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:31:37Z","timestamp":1760196697000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/16\/12\/464"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,11,23]]},"references-count":20,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2018,12]]}},"alternative-id":["md16120464"],"URL":"https:\/\/doi.org\/10.3390\/md16120464","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,11,23]]}}}