Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/29370
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dc.contributor.authorSadgrove, Nicholas Jen
dc.contributor.authorSenbill, Haythamen
dc.contributor.authorVan Wyk, Ben-Eriken
dc.contributor.authorGreatrex, Ben Wen
dc.date.accessioned2020-09-02T04:16:08Z-
dc.date.available2020-09-02T04:16:08Z-
dc.date.issued2020-04-11-
dc.identifier.citationAntibiotics, 9(4), p. 1-16en
dc.identifier.issn2079-6382en
dc.identifier.urihttps://hdl.handle.net/1959.11/29370-
dc.description.abstractIn spite of the evidence for antimicrobial and acaricidal effects in ethnobotanical reports of <i>Callitris</i> and <i>Widdringtonia</i>, the diterpene acids from <i>Widdringtonia</i> have never been described and no comparison to the Australian clade sister genus <i>Callitris</i> has been made. The critically endangered South African Clanwilliam cedar, <i>Widdringtonia wallichii (syn. W. cedarbergensis)</i>, of the Cederberg Mountains was once prized for its enduring fragrant timbers and an essential oil that gives an aroma comparable to better known Mediterranean cedars, predominantly comprised by widdrol, cedrol, and thujopsene. In South Africa, two other 'cedars' are known, which are called <i>W. nodiflora</i> and <i>W. schwarzii</i>, but, until now, their chemical similarity to <i>W. wallichii</i> has not been investigated. Much like <i>Widdringtonia, Callitris</i> was once prized for its termite resistant timbers and an 'earthy' essential oil, but predominantly guaiol. The current study demonstrates that the essential oils were similar across all three species of <i>Widdringtonia</i> and two known non-volatile diterpene acids were identified in leaves: the pimaradiene sandaracopimaric acid (<b>1</b>) and the labdane Z-communic acid (<b>2</b>) with a lower yield of the <i>E</i>-isomer (<b>3</b>). Additionally, in the leaves of the three species, the structures of five new antimicrobial labdanes were assigned: 12-hydroxy-8<i>R</i>,17-epoxy-isocommunic acid (<b>4</b>), 8<i>S</i>-formyl-isocommunic acid (<b>5</b>), 8<i>R</i>,17-epoxy-isocommunic acid (<b>6</b>), 8<i>R</i>-17R-epoxy-<i>E</i>-communic acid (<b>7</b>), and 8R-17-epoxy-<i>E</i>-communic acid (<b>8</b>). Australian <i>Callitris columellaris (syn. C. glaucophylla)</i> also produced <b>1</b> and its isomer isopimaric acid, pisiferal (<b>9</b>), and pisiferic acid (<b>10</b>) from its leaves. <i>Callitris endlicheri</i> (Parl.) F.M.Bailey yielded isoozic acid (<b>11</b>) as the only major diterpene. Diterpenes <b>4-6</b>, pisiferic acid (<b>10</b>), spathulenol, and guaiol (<b>12</b>) demonstrated antimicrobial and acaricidal activity.en
dc.languageenen
dc.publisherMDPI AGen
dc.relation.ispartofAntibioticsen
dc.rightsAttribution 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.titleNew Labdanes with Antimicrobial and Acaricidal Activity: Terpenes of Callitris and Widdringtonia (Cupressaceae)en
dc.typeJournal Articleen
dc.identifier.doi10.3390/antibiotics9040173en
dc.identifier.pmid32290471en
dcterms.accessRightsUNE Greenen
local.contributor.firstnameNicholas Jen
local.contributor.firstnameHaythamen
local.contributor.firstnameBen-Eriken
local.contributor.firstnameBen Wen
local.subject.for2008060310 Plant Systematics and Taxonomyen
local.subject.for2008030502 Natural Products Chemistryen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.subject.seo2008970106 Expanding Knowledge in the Biological Sciencesen
local.profile.schoolSchool of Rural Medicineen
local.profile.schoolSchool of Rural Medicineen
local.profile.emailnsadgro2@une.edu.auen
local.profile.emailhaytham.senbill@alexu.edu.egen
local.profile.emailbevanwyk@uj.ac.zaen
local.profile.emailbgreatre@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.publisher.placeSwitzerlanden
local.identifier.runningnumber173en
local.format.startpage1en
local.format.endpage16en
local.identifier.scopusid85083570145en
local.peerreviewedYesen
local.identifier.volume9en
local.identifier.issue4en
local.title.subtitleTerpenes of Callitris and Widdringtonia (Cupressaceae)en
local.access.fulltextYesen
local.contributor.lastnameSadgroveen
local.contributor.lastnameSenbillen
local.contributor.lastnameVan Wyken
local.contributor.lastnameGreatrexen
dc.identifier.staffune-id:nsadgro2en
dc.identifier.staffune-id:bgreatreen
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:1959.11/29370en
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitleNew Labdanes with Antimicrobial and Acaricidal Activityen
local.relation.fundingsourcenoteNational Research Foundation of South Africa (grant #8442)en
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorSadgrove, Nicholas Jen
local.search.authorSenbill, Haythamen
local.search.authorVan Wyk, Ben-Eriken
local.search.authorGreatrex, Ben Wen
local.open.fileurlhttps://rune.une.edu.au/web/retrieve/2213e629-74bd-454d-8ed8-58bb3d151608en
local.uneassociationYesen
local.atsiresearchNoen
local.sensitive.culturalNoen
local.identifier.wosid000537218600046en
local.year.published2020en
local.fileurl.openhttps://rune.une.edu.au/web/retrieve/2213e629-74bd-454d-8ed8-58bb3d151608en
local.fileurl.openpublishedhttps://rune.une.edu.au/web/retrieve/2213e629-74bd-454d-8ed8-58bb3d151608en
local.subject.for2020310411 Plant and fungus systematics and taxonomyen
local.subject.seo2020280105 Expanding knowledge in the chemical sciencesen
local.subject.seo2020280102 Expanding knowledge in the biological sciencesen
dc.notification.token7aa1d554-58cf-4277-917c-0cf25e327c24en
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School of Rural Medicine
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