{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T18:13:49Z","timestamp":1791051229472,"version":"4.1.0"},"reference-count":32,"publisher":"Elsevier BV","issue":"10","license":[{"start":{"date-parts":[[2009,7,1]],"date-time":"2009-07-01T00:00:00Z","timestamp":1246406400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Phytochemistry"],"published-print":{"date-parts":[[2009,7]]},"DOI":"10.1016\/j.phytochem.2009.07.017","type":"journal-article","created":{"date-parts":[[2009,8,20]],"date-time":"2009-08-20T08:16:35Z","timestamp":1250756195000},"page":"1315-1320","source":"Crossref","is-referenced-by-count":26,"title":["An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: Studies by NMR spectroscopic and computational methods"],"prefix":"10.1016","volume":"70","author":[{"given":"Carlos","family":"Areche","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aurelio","family":"San-Mart\u00edn","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juana","family":"Rovirosa","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jorge","family":"Soto-Delgado","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Renato","family":"Contreras","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.phytochem.2009.07.017_bib1","doi-asserted-by":"crossref","first-page":"5100","DOI":"10.1021\/jo980311g","article-title":"An efficient stereoselective synthesis of stypodiol and epistypodiol","volume":"63","author":"Abad","year":"1998","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.phytochem.2009.07.017_bib2","doi-asserted-by":"crossref","first-page":"404","DOI":"10.1002\/(SICI)1096-987X(199803)19:4<404::AID-JCC3>3.0.CO;2-W","article-title":"Geometry optimization of molecular structures in solution by the polarizable continuum model","volume":"19","author":"Barone","year":"1998","journal-title":"J. Comput. Chem."},{"key":"10.1016\/j.phytochem.2009.07.017_bib3","doi-asserted-by":"crossref","first-page":"9555","DOI":"10.1016\/j.tet.2003.10.001","article-title":"Simulation of 2D 1H homo- and 1H\u201313C heteronuclear NMR spectra of organic molecules by DFT calculations of spin\u2013spin coupling constants and 1H and 13C-chemical shifts","volume":"59","author":"Bassarello","year":"2003","journal-title":"Tetrahedron"},{"key":"10.1016\/j.phytochem.2009.07.017_bib4","doi-asserted-by":"crossref","first-page":"728","DOI":"10.1021\/np0705918","article-title":"Structural reassignment of obtusallenes V, VI, and VII by GIAO-based density functional prediction","volume":"71","author":"Braddock","year":"2008","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2009.07.017_bib5","doi-asserted-by":"crossref","first-page":"962","DOI":"10.1002\/mrc.2288","article-title":"DFT\/NMR integrated approach: a valid support to the total synthesis of chiral molecules","volume":"46","author":"Chini","year":"2008","journal-title":"Magn. Reson. Chem."},{"key":"10.1016\/j.phytochem.2009.07.017_bib6","doi-asserted-by":"crossref","first-page":"7763","DOI":"10.1016\/j.tet.2005.05.101","article-title":"Calculated NMR as a tool for structural elucidation of jungianol and mutisianthol","volume":"61","author":"Da-Silva","year":"2005","journal-title":"Tetrahedron"},{"key":"10.1016\/j.phytochem.2009.07.017_bib7","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1023\/A:1006879308861","article-title":"The compound 14-keto-stypodiol diacetate from the algae Stypopodium flabelliforme inhibits microtubules and cell proliferation in DU-145 human prostatic cells","volume":"187","author":"Depix","year":"1998","journal-title":"Mol. Cell. Biochem."},{"key":"10.1016\/j.phytochem.2009.07.017_bib8","unstructured":"Dictionary of Natural Products on CD-ROM, 2007. Chapman and Hall\/CRC, Boca Raton, Florida, USA."},{"key":"10.1016\/j.phytochem.2009.07.017_bib9","doi-asserted-by":"crossref","first-page":"1727","DOI":"10.1021\/np020090g","article-title":"New terpenoids from the brown alga Stypopodium zonale","volume":"65","author":"Dorta","year":"2002","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2009.07.017_bib10","series-title":"Gaussian 03, Revision C.02","author":"Frisch","year":"2004"},{"key":"10.1016\/j.phytochem.2009.07.017_bib11","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1021\/jo00314a005","article-title":"Ichthyotoxic and cytotoxic metabolites of the tropical brown alga Stypopodium zonale (Lamouroux) Papenfuss","volume":"46","author":"Gerwick","year":"1981","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.phytochem.2009.07.017_bib12","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1016\/0031-9422(82)83154-3","article-title":"Phenolic lipids from related marine algae of the order dictyotales","volume":"21","author":"Gerwick","year":"1982","journal-title":"Phytochemistry"},{"key":"10.1016\/j.phytochem.2009.07.017_bib13","doi-asserted-by":"crossref","first-page":"1279","DOI":"10.1016\/S0031-9422(00)81115-2","article-title":"Chemical variation in the tropical seaweed Stypopodium zonale (dictyotaceae)","volume":"24","author":"Gerwick","year":"1985","journal-title":"Phytochemistry"},{"key":"10.1016\/j.phytochem.2009.07.017_bib14","doi-asserted-by":"crossref","first-page":"PL25","DOI":"10.1016\/0024-3205(95)00260-D","article-title":"Inhibition of inflammatory responses by epitaondiol and other marine natural products","volume":"57","author":"Gil","year":"1995","journal-title":"Life Sci."},{"key":"10.1016\/j.phytochem.2009.07.017_bib15","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1016\/0040-4020(82)80215-9","article-title":"Diterpenoids of mixed biogenesis in phaeophyta biogenetic-type interconversions","volume":"38","author":"Gonzalez","year":"1982","journal-title":"Tetrahedron"},{"key":"10.1016\/j.phytochem.2009.07.017_bib16","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/S0022-0981(96)02659-7","article-title":"Marine chemical ecology: what is known and what is next?","volume":"200","author":"Hay","year":"1996","journal-title":"J. Exp. Mar. Biol. Ecol."},{"key":"10.1016\/j.phytochem.2009.07.017_bib17","series-title":"Ab Initio Molecular Orbital Theory","author":"Hehre","year":"1986"},{"key":"10.1016\/j.phytochem.2009.07.017_bib18","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1007\/BF02784281","article-title":"New trends in marine chemical ecology","volume":"29","author":"Ianora","year":"2006","journal-title":"Estuaries and Coasts"},{"key":"10.1016\/j.phytochem.2009.07.017_bib19","doi-asserted-by":"crossref","first-page":"2097","DOI":"10.1039\/P19740002097","article-title":"Selective synthesis of monomethyltocols via n-allylnickel complexes","volume":"I","author":"Inoue","year":"1974","journal-title":"JCS Perkin"},{"key":"10.1016\/j.phytochem.2009.07.017_bib20","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle\u2013Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"10.1016\/j.phytochem.2009.07.017_bib21","doi-asserted-by":"crossref","first-page":"1159","DOI":"10.1248\/cpb.53.1159","article-title":"New plastoquinones isolated from the brown alga, Sargassum micracanthun","volume":"53","author":"Mori","year":"2005","journal-title":"Chem. Pharm. Bull."},{"key":"10.1016\/j.phytochem.2009.07.017_bib22","doi-asserted-by":"crossref","first-page":"1209","DOI":"10.1016\/0031-9422(92)80262-D","article-title":"A cytotoxic principle of the brown alga Sargassum tortile and structures of chromenes","volume":"31","author":"Numata","year":"1992","journal-title":"Phytochemistry"},{"key":"10.1016\/j.phytochem.2009.07.017_bib23","doi-asserted-by":"crossref","first-page":"2679","DOI":"10.1016\/0031-9422(92)83610-B","article-title":"Isoepitaondiol, a diterpenoid of Stypopodium flabelliforme and the insecticidal activity of stypotriol, epitaondiol and derivatives","volume":"31","author":"Rovirosa","year":"1992","journal-title":"Phytochemistry"},{"key":"10.1016\/j.phytochem.2009.07.017_bib24","first-page":"219","article-title":"A new diterpenoid from the alga Stypopodium flabelliforme","volume":"39","author":"Rovirosa","year":"1994","journal-title":"Bol. Soc. Chil. Quim."},{"key":"10.1016\/j.phytochem.2009.07.017_bib25","doi-asserted-by":"crossref","first-page":"1022","DOI":"10.1021\/np050051f","article-title":"Neurotoxic meroditerpenoids from the tropical marine brown alga Stypopodium flabelliforme","volume":"68","author":"Sabry","year":"2005","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2009.07.017_bib26","doi-asserted-by":"crossref","first-page":"1475","DOI":"10.1021\/jo00110a062","article-title":"Epitaondiol: the first polycyclic meroditerpenoid containing two fused six-membered rings forced into the twist-boat conformation","volume":"60","author":"Sanchez-Ferrando","year":"1995","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.phytochem.2009.07.017_bib27","doi-asserted-by":"crossref","first-page":"1730","DOI":"10.1248\/cpb.54.1730","article-title":"Isolation of tetraprenyltoluquinols from the brown alga Sargassum thunbergii","volume":"54","author":"Seo","year":"2006","journal-title":"Chem. Pharm. Bull."},{"key":"10.1016\/j.phytochem.2009.07.017_bib28","doi-asserted-by":"crossref","first-page":"1347","DOI":"10.1016\/S0305-1978(03)00116-9","article-title":"Variation on diterpene production by the brazilian alga Stypopodium zonale (Dictyotales, Phaeophyta)","volume":"31","author":"Soares","year":"2003","journal-title":"Biochem. Syst. Ecol."},{"key":"10.1016\/j.phytochem.2009.07.017_bib29","doi-asserted-by":"crossref","first-page":"2027","DOI":"10.1021\/cr00031a013","article-title":"Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent","volume":"94","author":"Tomasi","year":"1994","journal-title":"Chem. Rev."},{"key":"10.1016\/j.phytochem.2009.07.017_bib30","doi-asserted-by":"crossref","first-page":"901","DOI":"10.1002\/cbdv.200590066","article-title":"Marine polyprenylated hydroquinones, quinones, and chromenols with inhibitory effects on leukotriene formation","volume":"2","author":"Tziveleka","year":"2005","journal-title":"Chem. Biodivers."},{"key":"10.1016\/j.phytochem.2009.07.017_bib31","doi-asserted-by":"crossref","first-page":"927","DOI":"10.1021\/np990010h","article-title":"A new tyrosine kinase inhibitor from the marine brown alga Stypopodium zonale","volume":"62","author":"Wessels","year":"1999","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2009.07.017_bib32","doi-asserted-by":"crossref","first-page":"8251","DOI":"10.1021\/ja00179a005","article-title":"Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations","volume":"112","author":"Wolinski","year":"1990","journal-title":"J. Am. Chem. Soc."}],"container-title":["Phytochemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0031942209002921?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0031942209002921?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2018,12,17]],"date-time":"2018-12-17T18:52:58Z","timestamp":1545072778000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0031942209002921"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,7]]},"references-count":32,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2009,7]]}},"alternative-id":["S0031942209002921"],"URL":"https:\/\/doi.org\/10.1016\/j.phytochem.2009.07.017","relation":{},"ISSN":["0031-9422"],"issn-type":[{"value":"0031-9422","type":"print"}],"subject":[],"published":{"date-parts":[[2009,7]]}}}