Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity (Journal article)

Xanthakis, E./ Magkouta, S./ Loutrari, H./ Stamatis, H./ Roussos, C./ Kolisis, F. N.

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dc.contributor.authorXanthakis, E.en
dc.contributor.authorMagkouta, S.en
dc.contributor.authorLoutrari, H.en
dc.contributor.authorStamatis, H.en
dc.contributor.authorRoussos, C.en
dc.contributor.authorKolisis, F. N.en
dc.date.accessioned2015-11-24T16:34:19Z-
dc.date.available2015-11-24T16:34:19Z-
dc.identifier.issn1024-2422-
dc.identifier.urihttps://olympias.lib.uoi.gr/jspui/handle/123456789/7791-
dc.rightsDefault Licence-
dc.subjectperillyl alcoholen
dc.subjectenzymatic glucosylation/acylationen
dc.subjectglucosidaseen
dc.subjectlipase ben
dc.subjectantitumor growth activityen
dc.subjectorganic mediaen
dc.subjectcandida-antarcticaen
dc.subjectcanceren
dc.subjectsolventsen
dc.subjectlipaseen
dc.subjectchemopreventionen
dc.subjectspecificityen
dc.subjectstabilityen
dc.subjectacylationen
dc.subjectenzymesen
dc.titleEnzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activityen
heal.typejournalArticle-
heal.type.enJournal articleen
heal.type.elΆρθρο Περιοδικούel
heal.identifier.primaryDoi 10.1080/10242420902811089-
heal.identifier.secondary<Go to ISI>://000268032500002-
heal.identifier.secondaryhttp://informahealthcare.com/doi/abs/10.1080/10242420902811089-
heal.languageen-
heal.accesscampus-
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Επιστημών και Τεχνολογιών. Τμήμα Βιολογικών Εφαρμογών και Τεχνολογιώνel
heal.publicationDate2009-
heal.abstractThe monoterpene perillyl alcohol (POH), an intermediate in the plant terpenoid biosynthetic pathway, has well-established tumor chemopreventive and chemotherapeutic potential. We have previously shown that the primary hydroxyl group of POH is essential for its antitumor and anti-angiogenic activities. In the current study we present the enzymatic synthesis of two POH derivatives with different polar and hydrophobic characteristics, namely perillyl glucoside and perillyl glucoside fatty ester, through a two-step modification. Initial glucosylation of POH on its active hydroxyl group with D-(+)-glucose and subsequent esterification of the perillyl glucoside product with vinyl laurate were carried out using almond beta-glucosidase and lipase B from Candida antarctica, respectively, in a low-water system. Optimization of enzymatic reactions was performed to achieve the highest possible conversion yields. The antitumor cell proliferation activity against mouse Lewis lung carcinoma cells was retained in both derivatives, although the perillyl glucoside ester showed greater inhibition than perillyl glucoside. Our results underline the feasibility of enzymatically producing novel bioactive analogs of phytochemicals displaying useful physicochemical properties.en
heal.journalNameBiocatalysis and Biotransformationen
heal.journalTypepeer reviewed-
heal.fullTextAvailabilityTRUE-
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