Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity
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 activitie...
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ftnkunivathens:oai:lib.uoa.gr:uoadl:2981763 2024-02-11T09:57:24+01:00 Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity Xanthakis, E. Magkouta, S. Loutrari, H. Stamatis, H. Roussos, C. Kolisis, F.N. 2009-01-01 https://pergamos.lib.uoa.gr/uoa/dl/object/uoadl:2981763 Αγγλικά English eng uoadl:2981763 https://pergamos.lib.uoa.gr/uoa/dl/object/uoadl:2981763 scientific_publication_article Επιστημονική δημοσίευση - Άρθρο Περιοδικού Scientific publication - Journal Article 2009 ftnkunivathens 2024-01-18T18:14:38Z 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 β-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. Article in Journal/Newspaper Antarc* Antarctica Pergamos - Library and Information Center of National and Kapodistrian University of Athens Almond ENVELOPE(163.617,163.617,-78.383,-78.383) |
institution |
Open Polar |
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Pergamos - Library and Information Center of National and Kapodistrian University of Athens |
op_collection_id |
ftnkunivathens |
language |
English |
description |
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 β-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. |
format |
Article in Journal/Newspaper |
author |
Xanthakis, E. Magkouta, S. Loutrari, H. Stamatis, H. Roussos, C. Kolisis, F.N. |
spellingShingle |
Xanthakis, E. Magkouta, S. Loutrari, H. Stamatis, H. Roussos, C. Kolisis, F.N. Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity |
author_facet |
Xanthakis, E. Magkouta, S. Loutrari, H. Stamatis, H. Roussos, C. Kolisis, F.N. |
author_sort |
Xanthakis, E. |
title |
Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity |
title_short |
Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity |
title_full |
Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity |
title_fullStr |
Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity |
title_full_unstemmed |
Enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity |
title_sort |
enzymatic synthesis of perillyl alcohol derivatives and investigation of their antiproliferative activity |
publishDate |
2009 |
url |
https://pergamos.lib.uoa.gr/uoa/dl/object/uoadl:2981763 |
long_lat |
ENVELOPE(163.617,163.617,-78.383,-78.383) |
geographic |
Almond |
geographic_facet |
Almond |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
uoadl:2981763 https://pergamos.lib.uoa.gr/uoa/dl/object/uoadl:2981763 |
_version_ |
1790609702467403776 |