New Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity

<i>Maesa membranacea</i> A. DC. (Primulaceae) is a plant species that has been frequently used by practitioners of the traditional ethnobotany knowledge from northern and central Vietnam. However, the chemical constituents of the plant remained unknown until recently. Chromatographic sep...

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Autores principales:	Klaudia Michalska, Agnieszka Galanty, Thanh Nguyen Le, Janusz Malarz, Nguyen Quoc Vuong, Van Cuong Pham, Anna Stojakowska
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	cytotoxicity <i>Maesa membranacea</i> Maesaceae Primulaceae prostate cancer triterpenoids Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/ad4234118d4b495cb10fb812680c7580
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spelling	oai:doaj.org-article:ad4234118d4b495cb10fb812680c75802021-11-25T18:29:11ZNew Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity10.3390/molecules262270131420-3049https://doaj.org/article/ad4234118d4b495cb10fb812680c75802021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/7013https://doaj.org/toc/1420-3049<i>Maesa membranacea</i> A. DC. (Primulaceae) is a plant species that has been frequently used by practitioners of the traditional ethnobotany knowledge from northern and central Vietnam. However, the chemical constituents of the plant remained unknown until recently. Chromatographic separation of a chloroform-soluble fraction of extract from leaves of <i>M. membranacea</i> led to the isolation of two new polyesterified ursane triterpenes (<b>1</b>–<b>2</b>) and two known apocarotenoids: (+)-dehydrovomifoliol (<b>3</b>) and (+)-vomifoliol (<b>4</b>). The chemical structures of the undescribed triterpenoids were elucidated using 1D and 2D MNR and HRESIMS spectral data as 2<i>α</i>,6<i>β</i>,22<i>α</i>-triacetoxy-11<i>α</i>-(2-methylbutyryloxy)-urs-12-ene-3<i>α</i>,20<i>β</i>-diol (<b>1</b>) and 2<i>α</i>,6<i>β</i>,22<i>α</i>-triacetoxy-urs-12-ene-3<i>α</i>,11<i>α</i>,20<i>β</i>-triol (<b>2</b>). The newly isolated triterpenoids were tested for their cytotoxic activity in vitro against two melanoma cell lines (HTB140 and A375), normal skin keratinocytes (HaCaT), two colon cancer cell lines (HT29 and Caco-2), two prostate cancer cell lines (DU145 and PC3) and normal prostate epithelial cells (PNT-2). Doxorubicin was used as a reference cytostatic drug. The 2<i>α</i>,6<i>β</i>,22<i>α</i>-triacetoxy-11<i>α</i>-(2-methylbutyryloxy)-urs-12-ene-3<i>α</i>,20<i>β</i>-diol demonstrated cytotoxic activity against prostate cancer cell lines (Du145—IC<sub>50</sub> = 35.8 µg/mL, PC3—IC<sub>50</sub> = 41.6 µg/mL), and at a concentration of 100 µg/mL reduced viability of normal prostate epithelium (PNT-2) cells by 41%.Klaudia MichalskaAgnieszka GalantyThanh Nguyen LeJanusz MalarzNguyen Quoc VuongVan Cuong PhamAnna StojakowskaMDPI AGarticlecytotoxicity<i>Maesa membranacea</i>MaesaceaePrimulaceaeprostate cancertriterpenoidsOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 7013, p 7013 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	cytotoxicity <i>Maesa membranacea</i> Maesaceae Primulaceae prostate cancer triterpenoids Organic chemistry QD241-441
spellingShingle	cytotoxicity <i>Maesa membranacea</i> Maesaceae Primulaceae prostate cancer triterpenoids Organic chemistry QD241-441 Klaudia Michalska Agnieszka Galanty Thanh Nguyen Le Janusz Malarz Nguyen Quoc Vuong Van Cuong Pham Anna Stojakowska New Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity
description	<i>Maesa membranacea</i> A. DC. (Primulaceae) is a plant species that has been frequently used by practitioners of the traditional ethnobotany knowledge from northern and central Vietnam. However, the chemical constituents of the plant remained unknown until recently. Chromatographic separation of a chloroform-soluble fraction of extract from leaves of <i>M. membranacea</i> led to the isolation of two new polyesterified ursane triterpenes (<b>1</b>–<b>2</b>) and two known apocarotenoids: (+)-dehydrovomifoliol (<b>3</b>) and (+)-vomifoliol (<b>4</b>). The chemical structures of the undescribed triterpenoids were elucidated using 1D and 2D MNR and HRESIMS spectral data as 2<i>α</i>,6<i>β</i>,22<i>α</i>-triacetoxy-11<i>α</i>-(2-methylbutyryloxy)-urs-12-ene-3<i>α</i>,20<i>β</i>-diol (<b>1</b>) and 2<i>α</i>,6<i>β</i>,22<i>α</i>-triacetoxy-urs-12-ene-3<i>α</i>,11<i>α</i>,20<i>β</i>-triol (<b>2</b>). The newly isolated triterpenoids were tested for their cytotoxic activity in vitro against two melanoma cell lines (HTB140 and A375), normal skin keratinocytes (HaCaT), two colon cancer cell lines (HT29 and Caco-2), two prostate cancer cell lines (DU145 and PC3) and normal prostate epithelial cells (PNT-2). Doxorubicin was used as a reference cytostatic drug. The 2<i>α</i>,6<i>β</i>,22<i>α</i>-triacetoxy-11<i>α</i>-(2-methylbutyryloxy)-urs-12-ene-3<i>α</i>,20<i>β</i>-diol demonstrated cytotoxic activity against prostate cancer cell lines (Du145—IC<sub>50</sub> = 35.8 µg/mL, PC3—IC<sub>50</sub> = 41.6 µg/mL), and at a concentration of 100 µg/mL reduced viability of normal prostate epithelium (PNT-2) cells by 41%.
format	article
author	Klaudia Michalska Agnieszka Galanty Thanh Nguyen Le Janusz Malarz Nguyen Quoc Vuong Van Cuong Pham Anna Stojakowska
author_facet	Klaudia Michalska Agnieszka Galanty Thanh Nguyen Le Janusz Malarz Nguyen Quoc Vuong Van Cuong Pham Anna Stojakowska
author_sort	Klaudia Michalska
title	New Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity
title_short	New Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity
title_full	New Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity
title_fullStr	New Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity
title_full_unstemmed	New Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity
title_sort	new polyesterified ursane derivatives from leaves of <i>maesa membranacea</i> and their cytotoxic activity
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/ad4234118d4b495cb10fb812680c7580
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New Polyesterified Ursane Derivatives from Leaves of <i>Maesa membranacea</i> and Their Cytotoxic Activity

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