Chromane Derivatives from Underground Parts of Iris tenuifolia and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation

Phytochemical investigation of the ethanol extract of underground parts of Iris tenuifolia Pall. afforded five new compounds; an unusual macrolide termed moniristenulide (1), 5-methoxy-6,7-methylenedioxy-4-O-2′-cycloflavan (2...

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Autores principales:	Oldokh Otgon, Suvd Nadmid, Christian Paetz, Hans-Martin Dahse, Kerstin Voigt, Stefan Bartram, Wilhelm Boland, Enkhmaa Dagvadorj
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Iris tenuifolia</i> Iridaceae chromane macrolide flavonoids antimicrobial Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/5f963fba475a43be9690e2f1b0afc2cb
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spelling	oai:doaj.org-article:5f963fba475a43be9690e2f1b0afc2cb2021-11-11T18:39:10ZChromane Derivatives from Underground Parts of <i>Iris tenuifolia</i> and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation10.3390/molecules262167051420-3049https://doaj.org/article/5f963fba475a43be9690e2f1b0afc2cb2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6705https://doaj.org/toc/1420-3049Phytochemical investigation of the ethanol extract of underground parts of <i>Iris tenuifolia</i> Pall. afforded five new compounds; an unusual macrolide termed moniristenulide (<b>1</b>), 5-methoxy-6,7-methylenedioxy-4-<i>O</i>-2′-cycloflavan (<b>2</b>), 5,7,2′,3′-tetrahydroxyflavanone (<b>3</b>), 5-hydroxy-6,7-dimethoxyisoflavone-2′-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>9</b>), 5,2′,3′-dihydroxy-6,7-dimethoxyisoflavone (<b>10</b>), along with seven known compounds (<b>4</b>–<b>8</b>, <b>11</b>–<b>12</b>). The structures of all purified compounds were established by analysis of 1D and 2D NMR spectroscopy and HR-ESI-MS. The antimicrobial activity of the compounds <b>1</b>–<b>3</b>, <b>5</b>, <b>9</b>, and <b>10</b> was investigated using the agar diffusion method against fungi, Gram-positive and Gram-negative bacteria. In consequence, new compound <b>3</b> was found to possess the highest antibacterial activity against <i>Enterococcus faecalis</i> VRE and <i>Mycobacterium vaccae</i>. Cell proliferation and cytotoxicity tests were also applied on all isolated compounds and plant crude extract in vitro with the result of potent inhibitory effect against leukemia cells. In particular, the newly discovered isoflavone <b>10</b> was active against both of the leukemia cells K-562 and THP-1 while <b>4</b>–<b>6</b> of the flavanone type compounds were active against only THP-1.Oldokh OtgonSuvd NadmidChristian PaetzHans-Martin DahseKerstin VoigtStefan BartramWilhelm BolandEnkhmaa DagvadorjMDPI AGarticle<i>Iris tenuifolia</i>IridaceaechromanemacrolideflavonoidsantimicrobialOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6705, p 6705 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Iris tenuifolia</i> Iridaceae chromane macrolide flavonoids antimicrobial Organic chemistry QD241-441
spellingShingle	<i>Iris tenuifolia</i> Iridaceae chromane macrolide flavonoids antimicrobial Organic chemistry QD241-441 Oldokh Otgon Suvd Nadmid Christian Paetz Hans-Martin Dahse Kerstin Voigt Stefan Bartram Wilhelm Boland Enkhmaa Dagvadorj Chromane Derivatives from Underground Parts of <i>Iris tenuifolia</i> and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation
description	Phytochemical investigation of the ethanol extract of underground parts of <i>Iris tenuifolia</i> Pall. afforded five new compounds; an unusual macrolide termed moniristenulide (<b>1</b>), 5-methoxy-6,7-methylenedioxy-4-<i>O</i>-2′-cycloflavan (<b>2</b>), 5,7,2′,3′-tetrahydroxyflavanone (<b>3</b>), 5-hydroxy-6,7-dimethoxyisoflavone-2′-<i>O</i>-<i>β</i>-<span style="font-variant: small-caps;">d</span>-glucopyranoside (<b>9</b>), 5,2′,3′-dihydroxy-6,7-dimethoxyisoflavone (<b>10</b>), along with seven known compounds (<b>4</b>–<b>8</b>, <b>11</b>–<b>12</b>). The structures of all purified compounds were established by analysis of 1D and 2D NMR spectroscopy and HR-ESI-MS. The antimicrobial activity of the compounds <b>1</b>–<b>3</b>, <b>5</b>, <b>9</b>, and <b>10</b> was investigated using the agar diffusion method against fungi, Gram-positive and Gram-negative bacteria. In consequence, new compound <b>3</b> was found to possess the highest antibacterial activity against <i>Enterococcus faecalis</i> VRE and <i>Mycobacterium vaccae</i>. Cell proliferation and cytotoxicity tests were also applied on all isolated compounds and plant crude extract in vitro with the result of potent inhibitory effect against leukemia cells. In particular, the newly discovered isoflavone <b>10</b> was active against both of the leukemia cells K-562 and THP-1 while <b>4</b>–<b>6</b> of the flavanone type compounds were active against only THP-1.
format	article
author	Oldokh Otgon Suvd Nadmid Christian Paetz Hans-Martin Dahse Kerstin Voigt Stefan Bartram Wilhelm Boland Enkhmaa Dagvadorj
author_facet	Oldokh Otgon Suvd Nadmid Christian Paetz Hans-Martin Dahse Kerstin Voigt Stefan Bartram Wilhelm Boland Enkhmaa Dagvadorj
author_sort	Oldokh Otgon
title	Chromane Derivatives from Underground Parts of <i>Iris tenuifolia</i> and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation
title_short	Chromane Derivatives from Underground Parts of <i>Iris tenuifolia</i> and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation
title_full	Chromane Derivatives from Underground Parts of <i>Iris tenuifolia</i> and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation
title_fullStr	Chromane Derivatives from Underground Parts of <i>Iris tenuifolia</i> and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation
title_full_unstemmed	Chromane Derivatives from Underground Parts of <i>Iris tenuifolia</i> and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation
title_sort	chromane derivatives from underground parts of <i>iris tenuifolia</i> and their in vitro antimicrobial, cytotoxicity and antiproliferative evaluation
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/5f963fba475a43be9690e2f1b0afc2cb
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Chromane Derivatives from Underground Parts of <i>Iris tenuifolia</i> and Their In Vitro Antimicrobial, Cytotoxicity and Antiproliferative Evaluation

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