Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from <i>Ventilago denticulata</i> Roots

Chromatographic separation of the crude extracts from the roots of <i>Ventilago denticulata</i> led to the isolation of four new anthraquinones, ventilanones L–O (<b>1</b>–<b>4</b>), together with eight known anthraquinones (<b>5</b>–<b>12</b&...

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Main Authors: Nattika Hangsamai, Kanokwan Photai, Thidathep Mahaamnart, Somdej Kanokmedhakul, Kwanjai Kanokmedhakul, Thanaset Senawong, Siripit Pitchuanchom, Mongkol Nontakitticharoen
Format: Article
Language:English
Published: MDPI AG 2022-02-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/27/3/1088
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author Nattika Hangsamai
Kanokwan Photai
Thidathep Mahaamnart
Somdej Kanokmedhakul
Kwanjai Kanokmedhakul
Thanaset Senawong
Siripit Pitchuanchom
Mongkol Nontakitticharoen
author_facet Nattika Hangsamai
Kanokwan Photai
Thidathep Mahaamnart
Somdej Kanokmedhakul
Kwanjai Kanokmedhakul
Thanaset Senawong
Siripit Pitchuanchom
Mongkol Nontakitticharoen
author_sort Nattika Hangsamai
collection DOAJ
description Chromatographic separation of the crude extracts from the roots of <i>Ventilago denticulata</i> led to the isolation of four new anthraquinones, ventilanones L–O (<b>1</b>–<b>4</b>), together with eight known anthraquinones (<b>5</b>–<b>12</b>). Their structures were elucidated by spectroscopic methods (UV, IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and 2D NMR) and mass spectrometry (MS), as well as comparison of their spectroscopic data with those reported in the literature. HDACs inhibitory activity evaluation resulted that compound <b>2</b> exhibited moderate antiproliferative activity against HeLa and A549 cell lines but nontoxic to normal cell. Molecular docking indicated the phenolic functionality of <b>2</b> plays crucial interactions with class II HDAC4 enzyme.
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spelling doaj.art-c1e9da8556874ed39c1cec3d67bc27102023-11-23T17:17:27ZengMDPI AGMolecules1420-30492022-02-01273108810.3390/molecules27031088Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from <i>Ventilago denticulata</i> RootsNattika Hangsamai0Kanokwan Photai1Thidathep Mahaamnart2Somdej Kanokmedhakul3Kwanjai Kanokmedhakul4Thanaset Senawong5Siripit Pitchuanchom6Mongkol Nontakitticharoen7Natural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, ThailandNatural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, ThailandNatural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, ThailandNatural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, ThailandNatural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, ThailandNatural Products Research Unit, Department of Biochemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, ThailandDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Mahasarakham University, Maha Sarakham 44150, ThailandNatural Products Research Unit, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, ThailandChromatographic separation of the crude extracts from the roots of <i>Ventilago denticulata</i> led to the isolation of four new anthraquinones, ventilanones L–O (<b>1</b>–<b>4</b>), together with eight known anthraquinones (<b>5</b>–<b>12</b>). Their structures were elucidated by spectroscopic methods (UV, IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and 2D NMR) and mass spectrometry (MS), as well as comparison of their spectroscopic data with those reported in the literature. HDACs inhibitory activity evaluation resulted that compound <b>2</b> exhibited moderate antiproliferative activity against HeLa and A549 cell lines but nontoxic to normal cell. Molecular docking indicated the phenolic functionality of <b>2</b> plays crucial interactions with class II HDAC4 enzyme.https://www.mdpi.com/1420-3049/27/3/1088<i>Ventilago denticulata</i>anthraquinoneHDAC inhibitorcytotoxicity
spellingShingle Nattika Hangsamai
Kanokwan Photai
Thidathep Mahaamnart
Somdej Kanokmedhakul
Kwanjai Kanokmedhakul
Thanaset Senawong
Siripit Pitchuanchom
Mongkol Nontakitticharoen
Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from <i>Ventilago denticulata</i> Roots
Molecules
<i>Ventilago denticulata</i>
anthraquinone
HDAC inhibitor
cytotoxicity
title Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from <i>Ventilago denticulata</i> Roots
title_full Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from <i>Ventilago denticulata</i> Roots
title_fullStr Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from <i>Ventilago denticulata</i> Roots
title_full_unstemmed Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from <i>Ventilago denticulata</i> Roots
title_short Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from <i>Ventilago denticulata</i> Roots
title_sort four new anthraquinones with histone deacetylase inhibitory activity from i ventilago denticulata i roots
topic <i>Ventilago denticulata</i>
anthraquinone
HDAC inhibitor
cytotoxicity
url https://www.mdpi.com/1420-3049/27/3/1088
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