{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T15:51:41Z","timestamp":1792165901597,"version":"4.4.0"},"reference-count":28,"publisher":"American Chemical Society (ACS)","license":[{"start":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T00:00:00Z","timestamp":1792108800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["22K05806"],"award-info":[{"award-number":["22K05806"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["23KJ1781"],"award-info":[{"award-number":["23KJ1781"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Four new trinor-guaiane sesquiterpenes, clavuridin C (1), clavuridin D (2), 5-methoxyclavuridin B (3), and 5-epi-clavuridin B (4), together with three known compounds, clavuridin B (6), clavularin A (7), and clavularin B (8), were isolated from the soft coral Clavularia viridis collected from the coast of Cape Kyan, Okinawa Prefecture, Japan. The structures of the newly isolated compounds 1\u20134, including their relative configurations, were elucidated through detailed analysis of spectroscopic data, such as IR, NMR, MS, and density functional theory (DFT)-based DP4 analysis, as well as by comparison with previously reported related compounds. The absolute configurations of 2 and 3 were additionally investigated through electronic circular dichroism (ECD) calculations. The absolute configuration of 4 was determined through benzoylation, followed by application of the allylic benzoate rule. Furthermore, structural differences between 4 and antheliol (4a) were addressed through detailed comparison of experimental and calculated NMR data, including DP4 and CP3 analyses, leading to a revision of the previously proposed structure. These results highlight the importance of integrated spectroscopic and computational approaches for accurate structure determination of closely related sesquiterpenes. In addition, isolated compounds 1\u20134 and 6\u20138 were evaluated for their antibacterial and antifungal activities.<\/jats:p>","DOI":"10.1021\/acsomega.6c08064","type":"journal-article","created":{"date-parts":[[2026,10,16]],"date-time":"2026-10-16T15:02:15Z","timestamp":1792162935000},"source":"Crossref","is-referenced-by-count":0,"title":["Trinor-Guaiane-Type Sesquiterpenes with Unusual Skeletons\nfrom the Okinawan Soft Coral\n                    <i>Clavularia viridis<\/i>"],"prefix":"10.1021","author":[{"given":"Kazuki","family":"Tani","sequence":"first","affiliation":[{"name":"University of the Ryukyus , , 1 Senbaru, Nishihara , ,","place":["Okinawa, Japan, 903-0213"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Misaki","family":"Nagasaka","sequence":"additional","affiliation":[{"name":"University of the Ryukyus , , 1 Senbaru, Nishihara , ,","place":["Okinawa, Japan, 903-0213"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0001-8269-1372","authenticated-orcid":true,"given":"Tomoki","family":"Tsuruta","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi-ku, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ayaka","family":"Fukushige","sequence":"additional","affiliation":[{"name":"University of the Ryukyus , , 1 Senbaru, Nishihara , ,","place":["Okinawa, Japan, 903-0213"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ayari","family":"Hojo","sequence":"additional","affiliation":[{"name":"University of the Ryukyus , , 1 Senbaru, Nishihara , ,","place":["Okinawa, Japan, 903-0213"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Matsumi","family":"Doe","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi-ku, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroyuki","family":"Miyake","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi-ku, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoshiki","family":"Morimoto","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi-ku, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4508-2105","authenticated-orcid":true,"given":"Masaru","family":"Hashimoto","sequence":"additional","affiliation":[{"name":"Hirosaki University , , 3-Bunkyo-cho , ,","place":["Hirosaki, Japan, 036 8561"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shinsuke","family":"Marumoto","sequence":"additional","affiliation":[{"name":"Kindai University , , 3-4-1 Kowakae , , ,","place":["Higashi-Osaka, Osaka, Japan, 577-8502"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michihiro","family":"Ito","sequence":"additional","affiliation":[{"name":"University of the Ryukyus , , 1 Senbaru, Nishihara , ,","place":["Okinawa, Japan, 903-0213"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5631-3167","authenticated-orcid":true,"given":"Momochika","family":"Kumagai","sequence":"additional","affiliation":[{"name":"Kagoshima University , , 4-50-20 Shimoarata , ,","place":["Kagoshima, Japan, 890-0056"]},{"name":"Kagoshima University , , 1-21-24 Korimoto , ,","place":["Kagoshima, Japan, 890-0065"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3170-8023","authenticated-orcid":true,"given":"Keisuke","family":"Nishikawa","sequence":"additional","affiliation":[{"name":"Osaka Metropolitan University , , 3-3-138 Sugimoto , Sumiyoshi-ku, ,","place":["Osaka, Japan, 558-8585"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takahiro","family":"Ishii","sequence":"additional","affiliation":[{"name":"University of the Ryukyus , , 1 Senbaru, Nishihara , ,","place":["Okinawa, Japan, 903-0213"]},{"name":"Kagoshima University , , 1-21-24 Korimoto , ,","place":["Kagoshima, Japan, 890-0065"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,16]]},"reference":[{"key":"2026101611015005300_cit1","unstructured":"World Register of Marine\nSpecies. 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Chem.\nSoc."},{"key":"2026101611015005300_cit6","doi-asserted-by":"publisher","first-page":"1331","DOI":"10.1021\/acs.jnatprod.9b00100","article-title":"Clavukoellians\nA\u2013F, Highly Rearranged Nardosinane Sesquiterpenoids\nwith Antiangiogenic Activity from Clavularia koellikeri","volume":"82","author":"Wang","year":"2019","journal-title":"J. Nat. Prod."},{"key":"2026101611015005300_cit7","doi-asserted-by":"publisher","first-page":"3052","DOI":"10.1021\/acsomega.1c06156","article-title":"Dolabellane Diterpenoids from the\nXisha Soft Coral Clavularia viridis","volume":"7","author":"Gao","year":"2022","journal-title":"ACS Omega"},{"key":"2026101611015005300_cit8","doi-asserted-by":"publisher","first-page":"695","DOI":"10.3762\/bjoc.15.64","article-title":"New Sesquiterpenoids\nfrom the South\nChina Sea Soft Corals Clavularia viridis and Lemnalia flava","volume":"15","author":"Wu","year":"2019","journal-title":"Beilstein J. 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Lett."},{"key":"2026101611015005300_cit21","doi-asserted-by":"publisher","first-page":"37","DOI":"10.1002\/9781118120392","article-title":"Some Inherently\nChiral Chromophores\u2500Empirical Rules and Quantum Chemical Calculations","volume-title":"Comprehensive Chiroptical Spectroscopy: Applications\nin Stereochemical Analysis of Synthetic Compounds, Natural Products,\nand Biomolecules","author":"Kwit","year":"2012"},{"key":"2026101611015005300_cit22","doi-asserted-by":"publisher","first-page":"257","DOI":"10.1021\/ar50056a001","article-title":"Exciton Chirality\nMethod and Its Application to Configurational\nand Conformational Studies of Natural Products","volume":"5","author":"Harada","year":"1972","journal-title":"Acc. Chem. 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Res."},{"key":"2026101611015005300_cit25","doi-asserted-by":"publisher","first-page":"IS25071","DOI":"10.1071\/IS25071","article-title":"Redescription of\nthe Type Material of Clavularia de Blainville, 1830\n(Anthozoa: Octocorallia), with Descriptions of New Taxa and a New\nFamily","volume":"40","author":"Borghi","year":"2026","journal-title":"Invertebr. Syst."},{"key":"2026101611015005300_cit26","doi-asserted-by":"publisher","first-page":"4597","DOI":"10.1021\/jo900408d","article-title":"Assigning the Stereochemistry of Pairs of Diastereoisomers\nUsing GIAO NMR Shift Calculation","volume":"74","author":"Smith","year":"2009","journal-title":"J. Org. Chem."},{"key":"2026101611015005300_cit27","doi-asserted-by":"publisher","first-page":"12946","DOI":"10.1021\/ja105035r","article-title":"Assigning Stereochemistry\nto Single Diastereoisomers\nby GIAO NMR Calculation: The DP4 Probability","volume":"132","author":"Smith","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"2026101611015005300_cit28","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1007\/s10126-018-9853-1","article-title":"Ruegeria sp. Strains Isolated from\nthe Reef-Building Coral Galaxea fascicularis Inhibit\nGrowth of the Temperature-Dependent Pathogen Vibrio coralliilyticus","volume":"21","author":"Miura","year":"2019","journal-title":"Mar. 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