Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity

Abstract The synthesis of phytol-derived γ-butyrolactones as well as their evaluation for deterrent activity towards peach-potato aphid Myzus persicae and antiproliferative activity against four selected cancer cell lines are reported. Products were obtained in good yields (19–96%) and their structu...

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Autores principales:	Anna Gliszczyńska, Katarzyna Dancewicz, Beata Gabryś, Marta Świtalska, Joanna Wietrzyk, Gabriela Maciejewska
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2021
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/b2086acf110746249048b11b9fde3c9a
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spelling	oai:doaj.org-article:b2086acf110746249048b11b9fde3c9a2021-12-02T14:21:43ZSynthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity10.1038/s41598-021-83736-62045-2322https://doaj.org/article/b2086acf110746249048b11b9fde3c9a2021-02-01T00:00:00Zhttps://doi.org/10.1038/s41598-021-83736-6https://doaj.org/toc/2045-2322Abstract The synthesis of phytol-derived γ-butyrolactones as well as their evaluation for deterrent activity towards peach-potato aphid Myzus persicae and antiproliferative activity against four selected cancer cell lines are reported. Products were obtained in good yields (19–96%) and their structures were fully characterized by spectroscopic data (NMR, HRMS). Four synthesized δ-halo-γ-lactones (4–7) are new and have not been previously described in the literature. In the choice test phytol (1) appeared deterrent to M. persicae, whereas modifications of its structure did not cause the avoidance of the treated leaves by the aphids. In contrast, aphids were attracted to the leaves treated with the new trans-δ-chloro-γ-lactone (6). Electrical Penetration Graph (EPG) technique applied to explore the aphid probing and feeding activity revealed that neither phytol nor lactone 6 affected aphid probing and the consumption of phloem sap, which means that both phytol and the lactone 6 might have acted as postingestive modifiers of aphid behavior. The results of in vitro antitumor assays showed that obtained phytol derivatives exhibit cytotoxic activity against studied cancer cell lines (leukemia, lung and colon carcinoma and its doxorubicin resistant subline). Halolactones 4–6 were identified as the compounds, which arrest cell cycle of leukemia cells mainly in G2/M and S phases.Anna GliszczyńskaKatarzyna DancewiczBeata GabryśMarta ŚwitalskaJoanna WietrzykGabriela MaciejewskaNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 11, Iss 1, Pp 1-14 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Anna Gliszczyńska Katarzyna Dancewicz Beata Gabryś Marta Świtalska Joanna Wietrzyk Gabriela Maciejewska Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity
description	Abstract The synthesis of phytol-derived γ-butyrolactones as well as their evaluation for deterrent activity towards peach-potato aphid Myzus persicae and antiproliferative activity against four selected cancer cell lines are reported. Products were obtained in good yields (19–96%) and their structures were fully characterized by spectroscopic data (NMR, HRMS). Four synthesized δ-halo-γ-lactones (4–7) are new and have not been previously described in the literature. In the choice test phytol (1) appeared deterrent to M. persicae, whereas modifications of its structure did not cause the avoidance of the treated leaves by the aphids. In contrast, aphids were attracted to the leaves treated with the new trans-δ-chloro-γ-lactone (6). Electrical Penetration Graph (EPG) technique applied to explore the aphid probing and feeding activity revealed that neither phytol nor lactone 6 affected aphid probing and the consumption of phloem sap, which means that both phytol and the lactone 6 might have acted as postingestive modifiers of aphid behavior. The results of in vitro antitumor assays showed that obtained phytol derivatives exhibit cytotoxic activity against studied cancer cell lines (leukemia, lung and colon carcinoma and its doxorubicin resistant subline). Halolactones 4–6 were identified as the compounds, which arrest cell cycle of leukemia cells mainly in G2/M and S phases.
format	article
author	Anna Gliszczyńska Katarzyna Dancewicz Beata Gabryś Marta Świtalska Joanna Wietrzyk Gabriela Maciejewska
author_facet	Anna Gliszczyńska Katarzyna Dancewicz Beata Gabryś Marta Świtalska Joanna Wietrzyk Gabriela Maciejewska
author_sort	Anna Gliszczyńska
title	Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity
title_short	Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity
title_full	Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity
title_fullStr	Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity
title_full_unstemmed	Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity
title_sort	synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity
publisher	Nature Portfolio
publishDate	2021
url	https://doaj.org/article/b2086acf110746249048b11b9fde3c9a
work_keys_str_mv	AT annagliszczynska synthesisofnovelphytolderivedgbutyrolactonesandevaluationoftheirbiologicalactivity AT katarzynadancewicz synthesisofnovelphytolderivedgbutyrolactonesandevaluationoftheirbiologicalactivity AT beatagabrys synthesisofnovelphytolderivedgbutyrolactonesandevaluationoftheirbiologicalactivity AT martaswitalska synthesisofnovelphytolderivedgbutyrolactonesandevaluationoftheirbiologicalactivity AT joannawietrzyk synthesisofnovelphytolderivedgbutyrolactonesandevaluationoftheirbiologicalactivity AT gabrielamaciejewska synthesisofnovelphytolderivedgbutyrolactonesandevaluationoftheirbiologicalactivity
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Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity

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