{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,13]],"date-time":"2026-03-13T04:50:22Z","timestamp":1773377422890,"version":"3.50.1"},"reference-count":15,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2024,10,18]],"date-time":"2024-10-18T00:00:00Z","timestamp":1729209600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["82273848"],"award-info":[{"award-number":["82273848"]}]},{"name":"National Natural Science Foundation of China","award":["2022YFC2804500"],"award-info":[{"award-number":["2022YFC2804500"]}]},{"name":"National Natural Science Foundation of China","award":["22-3-3-hygg-25-hy"],"award-info":[{"award-number":["22-3-3-hygg-25-hy"]}]},{"name":"National Key R&amp;D Program for Young Scientists of China","award":["82273848"],"award-info":[{"award-number":["82273848"]}]},{"name":"National Key R&amp;D Program for Young Scientists of China","award":["2022YFC2804500"],"award-info":[{"award-number":["2022YFC2804500"]}]},{"name":"National Key R&amp;D Program for Young Scientists of China","award":["22-3-3-hygg-25-hy"],"award-info":[{"award-number":["22-3-3-hygg-25-hy"]}]},{"name":"key technology tackling and industrialization demonstration projects in Qingdao","award":["82273848"],"award-info":[{"award-number":["82273848"]}]},{"name":"key technology tackling and industrialization demonstration projects in Qingdao","award":["2022YFC2804500"],"award-info":[{"award-number":["2022YFC2804500"]}]},{"name":"key technology tackling and industrialization demonstration projects in Qingdao","award":["22-3-3-hygg-25-hy"],"award-info":[{"award-number":["22-3-3-hygg-25-hy"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Pyrrole\u2013imidazole alkaloids (PIAs) are a class of marine sponge derived natural products which have complex carbon frameworks and broad bioactivities. In this study, four new alkaloids, stylimassalins A\u2013B (1\u20132), 3, and 5, together with two known compounds (4 and 6), were isolated from Stylissa massa. Compounds 2, 4, and 6 are the C-2 brominated analogues of 1, 3, and 5, respectively. Their structures display three different scaffolds, of which scaffold 1 (compounds 1,2) is new. A new biosynthetic pathway from oroidin, through spongiacidin, to latonduine and scaffold 1 was proposed by our group, in which the C12-N13-cleavaged compounds of spongiacidin (scaffold 2), dubbed seco-spongiacidins (3 and 4), are recognized as a key bridged scaffold, to afford PIA analogues (1,2 and 5,6). An anti-inflammatory evaluation in a zebrafish inflammation model induced by copper sulphate (CuSO4) demonstrated that stylimassalins A and B (1 and 2) could serve as a promising lead scaffold for treating inflammation.<\/jats:p>","DOI":"10.3390\/md22100477","type":"journal-article","created":{"date-parts":[[2024,10,21]],"date-time":"2024-10-21T09:58:24Z","timestamp":1729504704000},"page":"477","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Discovery of Anti-Inflammatory Alkaloids from Sponge Stylissa massa Suggests New Biosynthetic Pathways for Pyrrole\u2013Imidazole Alkaloids"],"prefix":"10.3390","volume":"22","author":[{"given":"Xiaojing","family":"Liu","sequence":"first","affiliation":[{"name":"Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4591-2129","authenticated-orcid":false,"given":"Qi","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yun","family":"Zhang","sequence":"additional","affiliation":[{"name":"Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250103, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hanting","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Natural Medicinal Chemistry and Pharmacognosy, School of Pharmacy, Qingdao University, Qingdao 266021, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,10,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1268","DOI":"10.1039\/C6NP00067C","article-title":"Muscarine, Imidazole, oxazole and thiazole alkaloids","volume":"33","author":"Jin","year":"2016","journal-title":"Nat. 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