Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata

Simple item page
dc.contributor.authorWhite, Andrew M.en
dc.contributor.authorPierens, Gregory K.en
dc.contributor.authorSkinner-Adams, Tinaen
dc.contributor.authorAndrews, Katherine T.en
dc.contributor.authorBernhardt, Paul V.en
dc.contributor.authorKrenske, Elizabeth H.en
dc.contributor.authorMollo, Ernestoen
dc.contributor.authorGarson, Mary J.en
dc.date.accessioned2025-12-16T19:40:51Z
dc.date.available2025-12-16T19:40:51Z
dc.date.issued2015-06-26en
dc.description.abstractFive new isocyano/isothiocyanato sesquiterpenes (1-5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26-0.30 μM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 μM.en
dc.description.statusPeer-revieweden
dc.format.extent6en
dc.identifier.issn0163-3864en
dc.identifier.otherPubMed:26056748en
dc.identifier.otherORCID:/0000-0002-9481-1079/work/167652631en
dc.identifier.scopus84933055130en
dc.identifier.urihttps://hdl.handle.net/1885/733795547
dc.language.isoenen
dc.rightsPublisher Copyright: © 2015 The American Chemical Society and American Society of Pharmacognosy.en
dc.sourceJournal of Natural Productsen
dc.titleAntimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellataen
dc.typeJournal articleen
dspace.entity.typePublicationen
local.bibliographicCitation.lastpage1427en
local.bibliographicCitation.startpage1422en
local.contributor.affiliationWhite, Andrew M.; School of Chemistry and Molecular Biosciencesen
local.contributor.affiliationPierens, Gregory K.; Griffith University Queenslanden
local.contributor.affiliationSkinner-Adams, Tina; National Research Council of Italyen
local.contributor.affiliationAndrews, Katherine T.; National Research Council of Italyen
local.contributor.affiliationBernhardt, Paul V.; University of Queenslanden
local.contributor.affiliationKrenske, Elizabeth H.; School of Chemistry and Molecular Biosciencesen
local.contributor.affiliationMollo, Ernesto; National Research Council of Italyen
local.contributor.affiliationGarson, Mary J.; University of Queenslanden
local.identifier.citationvolume78en
local.identifier.doi10.1021/acs.jnatprod.5b00354en
local.identifier.pure4aef4301-21ed-4bb7-be13-daf76279b6feen
local.identifier.urlhttps://www.scopus.com/pages/publications/84933055130en
local.type.statusPublisheden

Downloads

Collections

ANU Research Publications

DSpace software copyright © 2002-2026 LYRASIS