Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity

Xanthakis, E; Magkouta, S; Loutrari, H; Stamatis, H; Roussos, C; Kolisis, FN

dc.contributor.author	Xanthakis, E	en
dc.contributor.author	Magkouta, S	en
dc.contributor.author	Loutrari, H	en
dc.contributor.author	Stamatis, H	en
dc.contributor.author	Roussos, C	en
dc.contributor.author	Kolisis, FN	en
dc.date.accessioned	2014-03-01T01:30:21Z
dc.date.available	2014-03-01T01:30:21Z
dc.date.issued	2009	en
dc.identifier.issn	1024-2422	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/19565
dc.subject	Antitumor growth activity	en
dc.subject	Enzymatic glucosylation/acylation	en
dc.subject	Glucosidase	en
dc.subject	Lipase B	en
dc.subject	Perillyl alcohol	en
dc.subject.classification	Biochemistry & Molecular Biology	en
dc.subject.classification	Biotechnology & Applied Microbiology	en
dc.subject.other	Anti-angiogenic activity	en
dc.subject.other	Anti-tumor	en
dc.subject.other	Antiproliferative activities	en
dc.subject.other	Antitumor growth activity	en
dc.subject.other	Biosynthetic pathway	en
dc.subject.other	Chemopreventive	en
dc.subject.other	Conversion yield	en
dc.subject.other	Enzymatic glucosylation/acylation	en
dc.subject.other	Enzymatic reaction	en
dc.subject.other	Enzymatic synthesis	en
dc.subject.other	Fatty esters	en
dc.subject.other	Glucosidase	en
dc.subject.other	Glucosylation	en
dc.subject.other	Hydroxyl groups	en
dc.subject.other	Laurate	en
dc.subject.other	Lewis lung carcinomata	en
dc.subject.other	Lipase B from Candida antarctica	en
dc.subject.other	Low-water systems	en
dc.subject.other	Monoterpene	en
dc.subject.other	Perillyl alcohol	en
dc.subject.other	Physicochemical property	en
dc.subject.other	Phytochemicals	en
dc.subject.other	Proliferation activity	en
dc.subject.other	Terpenoid	en
dc.subject.other	Cell membranes	en
dc.subject.other	Cell proliferation	en
dc.subject.other	Esterification	en
dc.subject.other	Glucose	en
dc.subject.other	Esters	en
dc.subject.other	antineoplastic agent	en
dc.subject.other	beta glucosidase	en
dc.subject.other	glucose	en
dc.subject.other	lauric acid derivative	en
dc.subject.other	lipase B	en
dc.subject.other	perillyl alcohol	en
dc.subject.other	perillyl glucoside	en
dc.subject.other	perillyl glucoside lauric ester	en
dc.subject.other	terpene	en
dc.subject.other	unclassified drug	en
dc.subject.other	almond	en
dc.subject.other	animal cell	en
dc.subject.other	antineoplastic activity	en
dc.subject.other	article	en
dc.subject.other	biocatalyst	en
dc.subject.other	biotransformation	en
dc.subject.other	Candida antarctica	en
dc.subject.other	concentration response	en
dc.subject.other	controlled study	en
dc.subject.other	drug structure	en
dc.subject.other	drug synthesis	en
dc.subject.other	enzyme kinetics	en
dc.subject.other	esterification	en
dc.subject.other	glycosylation	en
dc.subject.other	growth inhibition	en
dc.subject.other	Lewis carcinoma	en
dc.subject.other	mouse	en
dc.subject.other	nonhuman	en
dc.subject.other	process optimization	en
dc.subject.other	Candida antarctica	en
dc.subject.other	Prunus dulcis	en
dc.title	Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity	en
heal.type	journalArticle	en
heal.identifier.primary	10.1080/10242420902811089	en
heal.identifier.secondary	http://dx.doi.org/10.1080/10242420902811089	en
heal.language	English	en
heal.publicationDate	2009	en
heal.abstract	The 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.publisher	TAYLOR & FRANCIS LTD	en
heal.journalName	Biocatalysis and Biotransformation	en
dc.identifier.doi	10.1080/10242420902811089	en
dc.identifier.isi	ISI:000268032500002	en
dc.identifier.volume	27	en
dc.identifier.issue	3	en
dc.identifier.spage	170	en
dc.identifier.epage	178	en