{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,11,6]],"date-time":"2026-11-06T14:25:11Z","timestamp":1793975111524,"version":"4.8.0"},"reference-count":30,"publisher":"American Chemical Society (ACS)","issue":"9","license":[{"start":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T00:00:00Z","timestamp":1787184000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T00:00:00Z","timestamp":1787184000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T00:00:00Z","timestamp":1787184000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22207132"],"award-info":[{"award-number":["22207132"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82273827"],"award-info":[{"award-number":["82273827"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>N-Acetylglucosamine (GlcNAc)-decorated natural products represent a structurally unique class of metabolites that possess diverse biological activities. Through the genome mining of Coccidioides sp. CMB-TN39F, we identified a GlcNAc transferase-encoding terpene synthase gene cluster brc. Heterologous expression of this cluster in Aspergillus nidulans enabled the characterization of seven GlcNAc-adorned brasilane-type sesquiterpene glycosides, including six previously undocumented compounds, brasilane G\u2212L (1\u22126), and one known compound, brasilane A (7). Functional characterization revealed that the cytochrome P450 BrcC functions as an epoxidase, catalyzing a stereoselective epoxidation of 7 to form 1. Compound 1 can undergo non-enzymatic conversions to generate compounds 2\u22125 under mildly acidic conditions. Pharmacological evaluation demonstrated that compounds 1\u22126 effectively downregulate the expression of pro-inflammatory cytokines (IL-6, IL-1\u03b2, and TNF-\u03b1) in LPS\/IFN-\u03b3-stimulated THP-1-derived macrophages. Notably, 1, which features an epoxide moiety, exhibits superior anti-inflammatory activity compared to its biosynthetic precursor 7, with an IC50 value of 30.4 \u03bcM against IL-6. This study expands the chemical space of GlcNAc-conjugated terpenoids and showcases a biosynthetic logic in which enzymatic tailoring is coupled with nonenzymatic reactions to amplify both structural diversity and biological properties.<\/jats:p>","DOI":"10.1021\/acs.jnatprod.6c00801","type":"journal-article","created":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T15:02:48Z","timestamp":1787238168000},"page":"2682-2693","source":"Crossref","is-referenced-by-count":0,"title":["Discovery and Biosynthesis of Brasilanes G\u2212L:\n                    <i>N<\/i>\n                    -Acetylglucosamine-Decorated Sesquiterpenoids with Anti-Inflammatory Activity"],"prefix":"10.1021","volume":"89","author":[{"given":"Ming-Min","family":"Wu","sequence":"first","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yao-Hui","family":"Shi","sequence":"additional","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu-Wei","family":"Lin","sequence":"additional","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wencong","family":"Yang","sequence":"additional","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]},{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9118-2185","authenticated-orcid":true,"given":"Shuo-Bin","family":"Chen","sequence":"additional","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3367-6659","authenticated-orcid":true,"given":"Hang","family":"Li","sequence":"additional","affiliation":[{"name":"Sun Yat-sen University , , ,","place":["Guangzhou, China, 510006"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,20]]},"reference":[{"key":"2026110608082874000_cit1","doi-asserted-by":"publisher","first-page":"643","DOI":"10.1146\/annurev.biochem.72.121801.161809","article-title":"A genetic approach to mammalian glycan function","volume":"72","author":"Lowe","year":"2003","journal-title":"Annu. 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