{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T15:05:52Z","timestamp":1789743952563,"version":"4.0.1"},"reference-count":21,"publisher":"American Chemical Society (ACS)","issue":"37","license":[{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100005273","name":"Natural Science Foundation of Yunnan Province","doi-asserted-by":"publisher","award":["202401BC070016"],"award-info":[{"award-number":["202401BC070016"]}],"id":[{"id":"10.13039\/501100005273","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100005273","name":"Natural Science Foundation of Yunnan Province","doi-asserted-by":"publisher","award":["202504BW050004"],"award-info":[{"award-number":["202504BW050004"]}],"id":[{"id":"10.13039\/501100005273","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["U23A20510"],"award-info":[{"award-number":["U23A20510"]}],"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":["U24A20806"],"award-info":[{"award-number":["U24A20806"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002367","name":"Chinese Academy of Sciences","doi-asserted-by":"publisher","award":["XDB1230000"],"award-info":[{"award-number":["XDB1230000"]}],"id":[{"id":"10.13039\/501100002367","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Lingang Laboratory","award":["LGL-2612-26"],"award-info":[{"award-number":["LGL-2612-26"]}]},{"name":"Yunnan Fundamental Research Projects","award":["202601AT070223"],"award-info":[{"award-number":["202601AT070223"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,18]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Sesterterpenoids with monocarbocyclic skeletons are key biosynthetic intermediates but are rarely isolated in plants. Herein, we report the discovery of 31 plant-derived monocarbocyclic sesterterpenoids, precolquhounoids, from the Lamiaceae shrub Colquhounia coccinea var. mollis. These isolates exhibit remarkable structural diversity, encompassing \u03b1-ketol regioisomers, spirolactone-containing stereoisomers, and highly oxidized frameworks featuring a uniquely fused 1,3-dioxolane core. The unambiguous stereochemical assignment of these highly flexible molecules employed an integrated structural elucidation strategy combining extensive NMR spectroscopic analysis, single-crystal X-ray diffraction, the modified Mosher\u2019s method, and TDDFT ECD calculations. Biogenetically, these diverse monocarbocyclic isolates serve as pivotal missing links, providing crucial insights into the divergent biosynthetic cascades that generate the complex 5\/6\/5-fused tricyclic architecture of colquhounoids. Furthermore, biological evaluations revealed that several of these novel precolquhounoids exhibit promising immunosuppressive (compound 6, IC50 = 9.81 \u00b1 1.86 \u03bcM) and antiadipogenic activities.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01390","type":"journal-article","created":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T16:10:41Z","timestamp":1788451841000},"page":"12607-12619","source":"Crossref","is-referenced-by-count":0,"title":["Structurally Diverse\nMonocarbocyclic Sesterterpenoid\nBiosynthetic Intermediates from\n                    <i>Colquhounia coccinea<\/i>\n                    var.\n                    <i>mollis<\/i>\n                    with Immunosuppressive and Antiadipogenic\nActivity"],"prefix":"10.1021","volume":"91","author":[{"given":"Ran","family":"Fu","sequence":"first","affiliation":[{"name":"Chinese Academy of Sciences , , ,","place":["Kunming, PR China, 650201"]},{"name":"University of Chinese Academy of Sciences , ,","place":["Beijing, PR China, 100049"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shu-Xi","family":"Jing","sequence":"additional","affiliation":[{"name":"Chinese Academy of Sciences , , ,","place":["Kunming, PR China, 650201"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ting-Ting","family":"Zhou","sequence":"additional","affiliation":[{"name":"Chinese Academy of Sciences , , ,","place":["Kunming, PR China, 650201"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chun-Huan","family":"Li","sequence":"additional","affiliation":[{"name":"Chinese Academy of Sciences , , ,","place":["Kunming, PR China, 650201"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4375-5457","authenticated-orcid":true,"given":"Yu","family":"Zheng","sequence":"additional","affiliation":[{"name":"Chinese Academy of Sciences , , ,","place":["Kunming, PR China, 650201"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ran","family":"Xu","sequence":"additional","affiliation":[{"name":"Chinese Academy of Sciences , , ,","place":["Kunming, PR China, 650201"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yan","family":"Liu","sequence":"additional","affiliation":[{"name":"Chengdu University of Traditional Chinese Medicine , , ,","place":["Chengdu, PR China, 611137"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5404-893X","authenticated-orcid":true,"given":"Sheng-Hong","family":"Li","sequence":"additional","affiliation":[{"name":"Chinese Academy of Sciences , , ,","place":["Kunming, PR China, 650201"]},{"name":"Chengdu University of Traditional Chinese Medicine , , ,","place":["Chengdu, PR China, 611137"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,2]]},"reference":[{"key":"2026091808090397500_cit1","doi-asserted-by":"publisher","first-page":"476","DOI":"10.1039\/C8NP00053K","article-title":"Challenges\nin the Configuration Assignment of Natural\nProducts. A Case-selective Perspective","volume":"36","author":"Menna","year":"2019","journal-title":"Nat.\nProd. Rep."},{"key":"2026091808090397500_cit2","doi-asserted-by":"publisher","first-page":"1005","DOI":"10.1039\/C9NP00018F","article-title":"Computational\nPrediction of Chiroptical Properties in Structure Elucidation of Natural\nProducts","volume":"36","author":"Grauso","year":"2019","journal-title":"Nat. Prod. Rep."},{"key":"2026091808090397500_cit3","doi-asserted-by":"publisher","first-page":"2293","DOI":"10.1039\/D1NP00021G","article-title":"The Untapped\nPotential of Plant Sesterterpenoids: Chemistry,\nBiological Activities and Biosynthesis","volume":"38","author":"Guo","year":"2021","journal-title":"Nat.\nProd. Rep."},{"key":"2026091808090397500_cit4","doi-asserted-by":"publisher","first-page":"443","DOI":"10.1039\/D4NP00041B","article-title":"Sesterterpenoids: Sources,\nStructural\nDiversity, Biological Activity, and Data Management","volume":"42","author":"Iobbi","year":"2025","journal-title":"Nat. Prod. Rep."},{"key":"2026091808090397500_cit5","doi-asserted-by":"publisher","first-page":"3147","DOI":"10.1016\/S0040-4039(01)81849-9","article-title":"Three New Sesterterpenoid Antibiotics\nfrom the Marine Sponge Luffariella variabilis","volume":"22","author":"De Silva","year":"1981","journal-title":"Tetrahedron Lett."},{"key":"2026091808090397500_cit6","doi-asserted-by":"publisher","first-page":"2079","DOI":"10.1016\/0006-2952(87)90134-1","article-title":"Inactivation of Bee Venom Phospholipase\nA2 by Manoalide. A Model Based on the Reactivity of Manoalide\nwith\nAmino Acids and Peptide Sequences","volume":"36","author":"Glaser","year":"1987","journal-title":"Biochem.\nPharmacol."},{"key":"2026091808090397500_cit7","doi-asserted-by":"publisher","first-page":"3639","DOI":"10.1016\/0006-2952(88)90396-6","article-title":"Inactivation of Phospholipase A2 by Manoalide: Localization of the Manoalide Binding Site\non Bee Venom Phospholipase A2","volume":"37","author":"Glaser","year":"1988","journal-title":"Biochem.\nPharmacol."},{"key":"2026091808090397500_cit8","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202421497","article-title":"Discovery\nand Total Synthesis of a New Class of Minor Immunosuppressive Plant\nSesterterpenoids","volume":"64","author":"Zheng","year":"2025","journal-title":"Angew. Chem., Int. 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