{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,20]],"date-time":"2026-05-20T06:59:59Z","timestamp":1779260399331,"version":"3.51.4"},"reference-count":21,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2024,9,27]],"date-time":"2024-09-27T00:00:00Z","timestamp":1727395200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["42276088"],"award-info":[{"award-number":["42276088"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>The chemical investigation of the South China Sea soft coral Sinularia densa has resulted in the isolation of seven new terpenoids, including two new meroterpenoids, namely sinudenoids F\u2013G (1\u20132), and five new cembranes, namely sinudenoids H\u2013L (3\u20137). Their structures and absolute configurations were elucidated based on extensive analyses of spectroscopic data, single-crystal X-ray diffraction, comparison with the literature data, and quantum chemical calculations. Among them, sinudenoid F (1) and sinudenoid G (2) are rare meroterpenoids featuring a methyl benzoate core. Sinudenoid H (3) possesses a rare carbon skeleton of 8, 19-bisnorfuranocembrenolide, which is the second reported compound with this skeleton. In a bioassay, sinudenoid H (3) exhibited better anti-inflammatory activity compared to the positive control indomethacin at 20 \u00b5M in CuSO4-treated transgenic fluorescent zebrafish. Moreover, sinudenoid J (5) and sinudenoid L (7) exhibited moderate anti-thrombotic activity in arachidonic acid (AA)-induced thrombotic zebrafish at 20 \u00b5M.<\/jats:p>","DOI":"10.3390\/md22100442","type":"journal-article","created":{"date-parts":[[2024,9,27]],"date-time":"2024-09-27T07:49:24Z","timestamp":1727423364000},"page":"442","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Terpenoids from the Soft Coral Sinularia densa Collected in the South China Sea"],"prefix":"10.3390","volume":"22","author":[{"given":"Cili","family":"Wang","sequence":"first","affiliation":[{"name":"Key Laboratory of Marine Food Processing & Safety Control, College of Food Science and Engineering, Ocean University of China, Qingdao 266003, China"},{"name":"Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jiarui","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kai","family":"Li","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Junjie","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lei","family":"Li","sequence":"additional","affiliation":[{"name":"Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250103, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sen","family":"Wang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hu","family":"Hou","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Food Processing & Safety Control, College of Food Science and Engineering, Ocean University of China, Qingdao 266003, China"},{"name":"Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4562-9609","authenticated-orcid":false,"given":"Pinglin","family":"Li","sequence":"additional","affiliation":[{"name":"Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China"},{"name":"Laboratory of Marine Drugs and Biological Products, National Laboratory for Marine Science and Technology, Qingdao 266235, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,9,27]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/0040-4020(75)85006-X","article-title":"Chemical studies of marine invertebrates. XI. Sinulariolide, a new cembranolide diterpene from the soft coral Sinularia flexibilis","volume":"31","author":"Tursch","year":"1975","journal-title":"Tetrahedron"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Yan, X., Liu, J., Leng, X., and Ouyang, H. (2021). Chemical Diversity and Biological Activity of Secondary Metabolites from Soft Coral Genus Sinularia since 2013. Mar. Drugs, 19.","DOI":"10.3390\/md19060335"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"10408","DOI":"10.1039\/D3RA01589K","article-title":"Sinulariaone A: A novel diterpenoid with a 13-membered carbocyclic skeleton from an octocoral Sinularia species","volume":"13","author":"Tseng","year":"2023","journal-title":"RSC Adv."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"107512","DOI":"10.1016\/j.cclet.2022.05.026","article-title":"Yonarolide A, an unprecedented furanobutenolide-containing norcembranoid derivative formed by photoinduced intramolecular [2+2] cycloaddition","volume":"34","author":"Du","year":"2023","journal-title":"Chin. Chem. Lett."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Pham, G.N., Kang, D.Y., Kim, M.J., Han, S.J., Lee, J.H., and Na, M.K. (2021). Isolation of Sesquiterpenoids and Steroids from the Soft Coral Sinularia brassica and Determination of Their Absolute Configuration. Mar. Drugs, 19.","DOI":"10.3390\/md19090523"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"131175","DOI":"10.1016\/j.molstruc.2021.131175","article-title":"Sterol constituents from a cultured octocoral Sinularia sandensis (Verseveldt 1977)","volume":"1246","author":"Phan","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1831","DOI":"10.1021\/acs.jnatprod.1c00367","article-title":"Sinularamides A-G, Terpenoid-Derived Spermidine and Spermine Conjugates with Casitas B-Lineage Lymphoma Proto-Oncogene B (Cbl-b) Inhibitory Activities from a Sinularia sp. Soft Coral","volume":"84","author":"Jiang","year":"2021","journal-title":"J. Nat. Prod."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5316","DOI":"10.3390\/md12105316","article-title":"Sinulolides A-H, new cyclopentenone and butenolide derivatives from soft coral Sinularia sp.","volume":"12","author":"Yang","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"5921","DOI":"10.1039\/D2QO01265K","article-title":"Discovery and photosynthesis of sinuaustones A and B, diterpenoids with a novel carbon scaffold isolated from soft coral Sinularia australiensis from Hainan","volume":"9","author":"Wu","year":"2022","journal-title":"Org. Chem. Front."},{"key":"ref_10","first-page":"17","article-title":"Cytotoxic and Antifungal Terpenoids from Bornean Soft Coral, Sinularia flexibilis","volume":"13","author":"Kamada","year":"2018","journal-title":"Nat. Prod. Commun."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"85","DOI":"10.1080\/10286020.2022.2046562","article-title":"Antifouling activity of terpenoids from the corals Sinularia flexibilis and Muricella sp. against the bryozoan Bugula neritina","volume":"25","author":"Wu","year":"2023","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"113960","DOI":"10.1016\/j.phytochem.2023.113960","article-title":"Four uncommon cycloamphilectane-type diterpenoids with antibacterial activity from the South China Sea soft coral Sinularia brassica","volume":"219","author":"Xia","year":"2024","journal-title":"Phytochemistry"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Huang, C., Jin, Y., Sun, R.N., Hu, K.Y., Yao, L.G., Guo, Y.W., Yuan, Z.H., and Li, X.W. (2024). Anti-HBV Activities of Cembranoids from the South China Sea Soft Coral Sinularia pedunculata and Their Structure Activity Relationship. Chem. Biodivers., 21.","DOI":"10.1002\/cbdv.202401146"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"9007","DOI":"10.1021\/acs.orglett.2c03631","article-title":"Sinudenoids A-E, C19-Norcembranoid Diterpenes with Unusual Scaffolds from the Soft Coral Sinularia densa","volume":"24","author":"Wang","year":"2022","journal-title":"Org. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"8820","DOI":"10.1021\/jo701635f","article-title":"Synthesis of substituted furoates from acrylates and aldehydes by Pd(oAc)2\/HPMoV\/CeCl3\/O2 system","volume":"72","author":"Tamaso","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"641","DOI":"10.1016\/j.tet.2009.11.078","article-title":"Two unprecedented cembrene-type terpenes from an indonesian soft coral sarcophyton sp.","volume":"66","author":"Kapojos","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1581","DOI":"10.1248\/cpb.c12-00756","article-title":"Diterpenoids from the Soft Coral Sinularia maxima and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Production of Pro-inflammatory Cytokines in Bone Marrow-Derived Dendritic Cells","volume":"60","author":"Thao","year":"2012","journal-title":"Chem. Pharm. Bull."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3379","DOI":"10.1016\/j.bmc.2010.04.012","article-title":"Bioactive norditerpenoids from the soft coral Sinularia gyrosa","volume":"18","author":"Cheng","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Ahmed, A.F., Tsai, C.R., Huang, C.Y., Wang, S.Y., and Sheu, J.H. (2017). Klyflaccicembranols A-I, New Cembranoids from the Soft Coral Klyxum flaccidum. Mar. Drugs, 15.","DOI":"10.3390\/md15010023"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2127","DOI":"10.1021\/jo00405a009","article-title":"Cembranoid diterpenes from a South Pacific soft coral","volume":"43","author":"Ravi","year":"1978","journal-title":"J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1628","DOI":"10.1021\/es4042836","article-title":"Resolving Biodegradation Patterns of Persistent Saturated Hydrocarbons in Weathered Oil Samples from the Deepwater Horizon Disaster","volume":"48","author":"Gros","year":"2014","journal-title":"Environ. Sci. Technol."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/22\/10\/442\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:05:01Z","timestamp":1760112301000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/22\/10\/442"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,9,27]]},"references-count":21,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2024,10]]}},"alternative-id":["md22100442"],"URL":"https:\/\/doi.org\/10.3390\/md22100442","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,9,27]]}}}