{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,13]],"date-time":"2026-05-13T14:59:48Z","timestamp":1778684388936,"version":"3.51.4"},"reference-count":52,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2013,3,5]],"date-time":"2013-03-05T00:00:00Z","timestamp":1362441600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Fractionation of the chloroform extract of Wikstroemia coriacea led to the isolation of two new compounds, oleodaphnoic acid (1), a guaiane-type sesquiterpenoid, and coriaceol (2), an 1,5-diphenyl-1-pentanone analogue, together with nine known compounds. The structures of 1 and 2 were elucidated by extensive spectroscopic data analysis. The known compounds were oleodaphnal (3), indicanone (4), (5R,8R,8aR)-3,8-dimethyl-4,5,6,7,8,8a-hexahydro-5-(1-methylethenyl)-2(1H)-azulenone, (5), 1,5 diphenyl-1-pentanone (6), (+)-3-hydroxy-1,5-diphenyl-1-pentanone (7), umbelliferone (8), daphnoretin (9), \u03b2-sitostenone (10) and (\u2212)-hinokinin (11).<\/jats:p>","DOI":"10.3390\/molecules18032988","type":"journal-article","created":{"date-parts":[[2013,3,5]],"date-time":"2013-03-05T11:27:47Z","timestamp":1362482867000},"page":"2988-2996","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Oleodaphnoic Acid and Coriaceol, Two New Natural Products from the Stem Bark of Wikstroemia coriacea"],"prefix":"10.3390","volume":"18","author":[{"given":"Nicolas","family":"Ingert","sequence":"first","affiliation":[{"name":"EIMS, UMR 241 Ecosyst\u00e8mes Insulaires Oc\u00e9aniens Universit\u00e9 de la Polyn\u00e9sie Fran\u00e7aise,  Tahiti 98702 FAA'A, French Polynesia"},{"name":"Centre Polyn\u00e9sien de Recherche sur la Biodiversit\u00e9 Insulaire, UMR 7138, IRD, Papeete BP 529-98713, French Polynesia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Isabelle","family":"Bombarda","sequence":"additional","affiliation":[{"name":"EIMS, UMR 241 Ecosyst\u00e8mes Insulaires Oc\u00e9aniens Universit\u00e9 de la Polyn\u00e9sie Fran\u00e7aise,  Tahiti 98702 FAA'A, French Polynesia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3374-2508","authenticated-orcid":false,"given":"Ga\u00ebtan","family":"Herbette","sequence":"additional","affiliation":[{"name":"Spectropole, FR1739, Aix-Marseille Universit\u00e9, Campus de St J\u00e9r\u00f4me - service 511, Marseille 13397, cedex 20, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert","family":"Faure","sequence":"additional","affiliation":[{"name":"SMBSO, UMR 7273, ICR, Aix-Marseille Universit\u00e9, Campus de St J\u00e9r\u00f4me - service 522,  Marseille 13397, cedex 20, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christian","family":"Moretti","sequence":"additional","affiliation":[{"name":"Centre Polyn\u00e9sien de Recherche sur la Biodiversit\u00e9 Insulaire, UMR 7138, IRD, Papeete BP 529-98713, French Polynesia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Phila","family":"Raharivelomanana","sequence":"additional","affiliation":[{"name":"EIMS, UMR 241 Ecosyst\u00e8mes Insulaires Oc\u00e9aniens Universit\u00e9 de la Polyn\u00e9sie Fran\u00e7aise,  Tahiti 98702 FAA'A, French Polynesia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2013,3,5]]},"reference":[{"key":"ref_1","first-page":"215","article-title":"WIKSTROEMIA Endlicher, Prodr. Fl. Norfolk","volume":"Volume 13","author":"Wang","year":"2007","journal-title":"Flora of China"},{"key":"ref_2","unstructured":"Butaud, J.-F., Cartier, C.L., Florence, J., Perlman, S.P., Sachet, M.-H., and Wood, K.R. Available online:http:\/\/www.herbier-tahiti.pf\/Selection_Taxonomie.php?id_tax=10079\/."},{"key":"ref_3","unstructured":"P\u00e9tard, P. (1986). Plantes utiles de la Polyn\u00e9sie-Raau Tahiti, Haere Po No Tahiti."},{"key":"ref_4","unstructured":"Nadeaud, J. (1864). Plantes usuelles des Tahitiens, J. Martel."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"234","DOI":"10.1055\/s-2004-815540","article-title":"New Lignans and Cytotoxic Constituents from Wikstroemia lanceolata","volume":"70","author":"Lin","year":"2004","journal-title":"Planta Med."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1248\/cpb.53.137","article-title":"Anti-inflammatory activity of new guaiane type sesquiterpene from Wikstroemia indica","volume":"53","author":"Wang","year":"2005","journal-title":"Chem. Pharm. Bull."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/0378-8741(88)90138-9","article-title":"Ethnopharmacologic and phytochemical studies of the Thymelaeaceae","volume":"24","author":"Borris","year":"1988","journal-title":"J. Ethnopharmacol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1002\/ptr.2650070220","article-title":"Oligo- and macrocyclic diterpenes in thymelaeaceae and euphorbiaceae occurring and utilized in yunnan (Southwest China) 4. Tigliane type diterpene esters (phorbol-12,13-diesters) from Wikstroemia canescens","volume":"7","author":"Wu","year":"1993","journal-title":"Phytother. Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"833","DOI":"10.1016\/S0031-9422(97)00529-3","article-title":"Minor daphnane-type diterpenoids from Wikstroemia retusa","volume":"47","author":"Abe","year":"1998","journal-title":"Phytochemistry"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1016\/S0031-9422(96)00602-4","article-title":"Daphnane diterpenoids from the bark of Wikstroemia retusa","volume":"44","author":"Abe","year":"1997","journal-title":"Phytochemistry"},{"key":"ref_11","first-page":"28","article-title":"A study on the constituents of Wikstroemia indica","volume":"33","author":"Chen","year":"1981","journal-title":"Taiwan Yao Hsueh Tsa Chih"},{"key":"ref_12","first-page":"192","article-title":"Studies on the coumarin derivatives. VII. Constituents of the bark of Daphne Kiusiana Miquel and others (Thymelaeaceae)","volume":"74","author":"Nakabayashi","year":"1954","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1991","DOI":"10.1016\/0031-9422(77)80110-6","article-title":"Wikstrosin, a tricoumarin from Wikstroemia viridiflora","volume":"16","author":"Tandon","year":"1977","journal-title":"Phytochemistry"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1002\/jps.2600710706","article-title":"Antitumor agents LIII: The effects of daphnoretin on nucleic acid and protein synthesis of ehrlich ascites tumor cells","volume":"71","author":"Hall","year":"1982","journal-title":"J. Pharm. Sci."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"530","DOI":"10.1021\/np50017a003","article-title":"Antitumor Agents. 49. Tricin,Kaempferol-3-O-\u03b2-d-Glucopyranoside and (+)-Nortrachelogenin, Antileukemic Principles From Wikstroemia indica","volume":"44","author":"Lee","year":"1981","journal-title":"J. Nat. Prod."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3631","DOI":"10.1248\/cpb.34.3631","article-title":"Two New C-3\/C-3\"-Biflavanones from Wikstroemia sikokiana","volume":"34","author":"Niwa","year":"1986","journal-title":"Chem. Pharm. Bull."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"879","DOI":"10.1016\/S0031-9422(00)90376-5","article-title":"Three biflavonoids from Wikstroemia sikokiana","volume":"37","author":"Baba","year":"1994","journal-title":"Phytochemistry"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1789","DOI":"10.1016\/S0031-9422(00)97493-4","article-title":"Wikstromol, a new lignan from Wikstroemia viridiflora","volume":"15","author":"Tandon","year":"1976","journal-title":"Phytochemistry"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1002\/jps.2600680545","article-title":"Wikstromol, antitumor lignan from Wikstroemia foetida var. oahuensis gray and Wikstroemia uva-ursi gray (thymelaeaceae)","volume":"68","author":"Torrance","year":"1979","journal-title":"J. Pharm. Sci."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1824","DOI":"10.1016\/S0031-9422(82)85082-6","article-title":"(+)-Arctigenin, a lignan from Wikstroemia indica","volume":"21","author":"Suzuki","year":"1982","journal-title":"Phytochemistry"},{"key":"ref_21","unstructured":"Rahman, A.-U., and Ahmad, V.U. (1992). 13C-NMR of Natural Products, Plenum Publishing."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1525","DOI":"10.1016\/S0031-9422(99)00305-2","article-title":"Terpenoids and aromatic compounds from Daphne oleoides ssp. oleoides","volume":"52","author":"Taninaka","year":"1999","journal-title":"Phytochemistry"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"509","DOI":"10.1021\/np50057a009","article-title":"Isocedrene and Guaiane Derivatives from Pleocarphus revolutus","volume":"51","author":"Zdero","year":"1988","journal-title":"J. Nat. Prod."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/0022-328X(87)85117-3","article-title":"One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums","volume":"332","author":"Vitale","year":"1987","journal-title":"J. Organomet. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"8988","DOI":"10.1016\/j.tet.2006.07.013","article-title":"Easy \u03b1-alkylation of ketones with alcohols through a hydrogen autotransfer process catalyzed by RuCl2(DMSO)4","volume":"62","author":"Yus","year":"2006","journal-title":"Tetrahedron"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1055\/s-0031-1280263","article-title":"Phenols with Anti-HIV Activity from Daphne acutiloba","volume":"78","author":"Huang","year":"2012","journal-title":"Planta Med."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1007\/BF02968244","article-title":"Chemical constituents of the root of Dystaenia takeshimana and their anti-inflammatory activity","volume":"29","author":"Kim","year":"2006","journal-title":"Arch. Pharm. Res."},{"key":"ref_28","first-page":"193","article-title":"Coumarin derivatives from Loeselia mexicana. Determination of the anxiolytic effect of daphnoretin on elevated plus-maze","volume":"51","author":"Rojas","year":"2007","journal-title":"J. Mex. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1002\/1099-1565(200011\/12)11:6<345::AID-PCA540>3.0.CO;2-T","article-title":"Chemical composition of the light petroleum extract of Hibiscus cannabinus bark and core","volume":"11","author":"Seca","year":"2000","journal-title":"Phytochem. Anal."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"638","DOI":"10.1016\/j.fct.2006.10.012","article-title":"(\u2212)-Hinokinin causes antigenotoxicity but not genotoxicity in peripheral blood of Wistar rats","volume":"45","author":"Medola","year":"2007","journal-title":"Food Chem. Toxicol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"11156","DOI":"10.1016\/j.tet.2005.09.026","article-title":"Synthesis of all 7[alpha]H-guaia-4,11-dien-3-one diastereomers from (+)-dihydrocarvone","volume":"61","author":"Blay","year":"2005","journal-title":"Tetrahedron"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"713","DOI":"10.1016\/0306-3623(95)02112-4","article-title":"Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential","volume":"27","author":"Hoult","year":"1996","journal-title":"Gen. Pharmacol."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"825","DOI":"10.1016\/j.foodchem.2009.11.022","article-title":"Umbelliferone\u2014An antioxidant isolated from Acacia nilotica (L.) Willd.  Ex. Del.","volume":"120","author":"Singh","year":"2010","journal-title":"Food Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"562","DOI":"10.1089\/jmf.2006.9.562","article-title":"Antihyperglycemic effect of Umbelliferone in streptozotocin-diabetic rats","volume":"9","author":"Ramesh","year":"2006","journal-title":"J. Med. Food"},{"key":"ref_35","first-page":"29","article-title":"Pharmaco-kinetics of coumarin and its metabolites. Preliminary results in three healthy volunteers","volume":"22","author":"Sharifi","year":"1992","journal-title":"J. Irish Coll. Phys. Surg."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"S3","DOI":"10.1007\/BF01377114","article-title":"Growth-inhibitory effects of coumarin (1,2-benzopyrone) and 7-hydroxycoumarin on human malignant cell lines in vitro","volume":"120","author":"Marshall","year":"1994","journal-title":"J. Cancer Res. Clin. Oncol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"502","DOI":"10.1007\/BF01191806","article-title":"Antitumour activity of coumarin and 7-hydroxycoumarin against 7, 12-dimethylbenz[a]anthracene-induced rat mammary carcinomas","volume":"120","author":"Maucher","year":"1994","journal-title":"J. Cancer Res. Clin. Oncol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"564","DOI":"10.1055\/s-2000-8601","article-title":"Antifungal, antimitotic and anti-HIV-1 agents from the roots of Wikstroemia indica","volume":"66","author":"Hu","year":"2000","journal-title":"Planta Med."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1042\/bj2950321","article-title":"Daphnoretin, a new protein kinase C activator isolated from Wikstroemia indica C. A. Mey","volume":"295","author":"Ko","year":"1993","journal-title":"Biochem. J."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1016\/0922-4106(95)90047-0","article-title":"Daphnoretin-induced respiratory burst in rat neutrophils is, probably, mainly through protein kinase C activation","volume":"288","author":"Wang","year":"1995","journal-title":"Eur. J. Pharmacol. Mol. Pharmacol. Sect."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1025","DOI":"10.1016\/0006-2952(96)00420-0","article-title":"Identification of a protein kinase C (PKC) activator, daphnoretin, that suppresses hepatitis B virus gene expression in human hepatoma cells","volume":"52","author":"Chen","year":"1996","journal-title":"Biochem. Pharmacol."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"657","DOI":"10.1002\/ptr.2935","article-title":"Antiviral Activity of Daphnoretin Isolated from Wikstroemia indica","volume":"24","author":"Ho","year":"2010","journal-title":"Phytother. Res."},{"key":"ref_43","first-page":"41","article-title":"Effect of the Fractions of the Hexane Bark Extract and Stigmast-4-en-3-one Isolated from Anacardium occidentale on Blood Glucose Tolerance Test in an Animal Model","volume":"3","author":"Morrison","year":"2007","journal-title":"Int. J. Pharmacol."},{"key":"ref_44","unstructured":"Kiyoshi, H., Yukari, N., Masakazu, M., Sansei, N., Katsuyuki, U., Kimiko, S., Tetsuya, K., and Akinobu, S. (2003). Antiarrhythmic agent. (2003\u2013113107), Japan Patent."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"850","DOI":"10.3390\/molecules14020850","article-title":"Bioactive Metabolites from Spilanthes acmella Murr.","volume":"14","author":"Prachayasittikul","year":"2009","journal-title":"Molecules"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/S0944-7113(99)80041-5","article-title":"Anti-emetic principles of Pogostemon cablin (Blanco) Benth","volume":"6","author":"Yang","year":"1999","journal-title":"Phytomedicine"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"761","DOI":"10.1055\/s-2001-18359","article-title":"Cardioactive Diterpenoids from the Roots of Salvia amplexicaulis","volume":"67","author":"Kolak","year":"2001","journal-title":"Planta Med."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"683","DOI":"10.1002\/ptr.1003","article-title":"Antitubercular constituents from the hexane fraction of Morinda citrifolia L. (Rubiaceae)","volume":"16","author":"Saludes","year":"2002","journal-title":"Phytother. Res."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"851","DOI":"10.1016\/j.phymed.2010.02.011","article-title":"Anti-inflammatory principles from Heritiera littoralis bark","volume":"17","author":"Tewtrakul","year":"2010","journal-title":"Phytomedicine"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"779","DOI":"10.1515\/znc-2009-11-1204","article-title":"Antimycobacterial activity of natural and semi-synthetic lignans","volume":"64","author":"Silva","year":"2009","journal-title":"Z. Naturforsch. C"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"7512","DOI":"10.1021\/jo971176v","article-title":"NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities","volume":"62","author":"Gottlieb","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref_52","unstructured":"The Herbarium of French Polynesia. Available online:http:\/\/www.herbier-tahiti.pf."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/18\/3\/2988\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:45:17Z","timestamp":1760219117000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/18\/3\/2988"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,3,5]]},"references-count":52,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2013,3]]}},"alternative-id":["molecules18032988"],"URL":"https:\/\/doi.org\/10.3390\/molecules18032988","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,3,5]]}}}