Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber <i>Holothuria atra</i>

The saponin composition of a specimen of black sea cucumber, <i>Holothuria atra</i> collected in the Persian Gulf was studied by a combined approach including LC-MS/MS, Molecular Networking, pure compound isolation, and NMR spectroscopy. The saponin composition of <i>Holothuria atr...

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Main Authors: Laura Grauso, Afsaneh Yegdaneh, Mohsen Sharifi, Alfonso Mangoni, Behzad Zolfaghari, Virginia Lanzotti
Format: Article
Language:English
Published: MDPI AG 2019-02-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/17/2/86
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spelling doaj-7418b61502184e76bcdf0e76a65736e42020-11-24T21:46:32ZengMDPI AGMarine Drugs1660-33972019-02-011728610.3390/md17020086md17020086Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber <i>Holothuria atra</i>Laura Grauso0Afsaneh Yegdaneh1Mohsen Sharifi2Alfonso Mangoni3Behzad Zolfaghari4Virginia Lanzotti5Dipartimento di Agraria, Università di Napoli Federico II, Via Università 100, 80055 Portici (NA), ItalyDepartment of Pharmacognosy, School of Pharmacy, Isfahan University of Medical Sciences, Hezar-Jerib Ave., 81746 73461 Isfahan, IranDepartment of Pharmacognosy, School of Pharmacy, Isfahan University of Medical Sciences, Hezar-Jerib Ave., 81746 73461 Isfahan, IranDipartimento di Farmacia, Università di Napoli Federico II, Via Domenico Montesano 49, 80131 Napoli, ItalyDepartment of Pharmacognosy, School of Pharmacy, Isfahan University of Medical Sciences, Hezar-Jerib Ave., 81746 73461 Isfahan, IranDipartimento di Agraria, Università di Napoli Federico II, Via Università 100, 80055 Portici (NA), ItalyThe saponin composition of a specimen of black sea cucumber, <i>Holothuria atra</i> collected in the Persian Gulf was studied by a combined approach including LC-MS/MS, Molecular Networking, pure compound isolation, and NMR spectroscopy. The saponin composition of <i>Holothuria atra</i> turned out to be more complex than previously reported. The most abundant saponins in the extract (<b>1</b>&#8315;<b>4</b>) were isolated and characterized by 1D- and 2D-NMR experiments. Compound <b>1</b> was identified as a new triterpene glycoside saponin, holothurin A5. The side chain of the new saponin <b>1</b>, unprecedented among triterpene glycosides, is characterized by an electrophilic enone function, which can undergo slow water or methanol addition under neutral conditions. The cytotoxic activity of compounds <b>1</b>&#8315;<b>4</b>, evaluated on the human cervix carcinoma HeLa cell line, was remarkable, with IC<sub>50</sub> values ranging from 1.2 to 2.5 &#181;g/mL.https://www.mdpi.com/1660-3397/17/2/86sea cucumbersholothurianssaponinstriterpene glycosidesLC-MS/MSmolecular networkingcytotoxic activity
collection DOAJ
language English
format Article
sources DOAJ
author Laura Grauso
Afsaneh Yegdaneh
Mohsen Sharifi
Alfonso Mangoni
Behzad Zolfaghari
Virginia Lanzotti
spellingShingle Laura Grauso
Afsaneh Yegdaneh
Mohsen Sharifi
Alfonso Mangoni
Behzad Zolfaghari
Virginia Lanzotti
Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber <i>Holothuria atra</i>
Marine Drugs
sea cucumbers
holothurians
saponins
triterpene glycosides
LC-MS/MS
molecular networking
cytotoxic activity
author_facet Laura Grauso
Afsaneh Yegdaneh
Mohsen Sharifi
Alfonso Mangoni
Behzad Zolfaghari
Virginia Lanzotti
author_sort Laura Grauso
title Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber <i>Holothuria atra</i>
title_short Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber <i>Holothuria atra</i>
title_full Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber <i>Holothuria atra</i>
title_fullStr Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber <i>Holothuria atra</i>
title_full_unstemmed Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber <i>Holothuria atra</i>
title_sort molecular networking-based analysis of cytotoxic saponins from sea cucumber <i>holothuria atra</i>
publisher MDPI AG
series Marine Drugs
issn 1660-3397
publishDate 2019-02-01
description The saponin composition of a specimen of black sea cucumber, <i>Holothuria atra</i> collected in the Persian Gulf was studied by a combined approach including LC-MS/MS, Molecular Networking, pure compound isolation, and NMR spectroscopy. The saponin composition of <i>Holothuria atra</i> turned out to be more complex than previously reported. The most abundant saponins in the extract (<b>1</b>&#8315;<b>4</b>) were isolated and characterized by 1D- and 2D-NMR experiments. Compound <b>1</b> was identified as a new triterpene glycoside saponin, holothurin A5. The side chain of the new saponin <b>1</b>, unprecedented among triterpene glycosides, is characterized by an electrophilic enone function, which can undergo slow water or methanol addition under neutral conditions. The cytotoxic activity of compounds <b>1</b>&#8315;<b>4</b>, evaluated on the human cervix carcinoma HeLa cell line, was remarkable, with IC<sub>50</sub> values ranging from 1.2 to 2.5 &#181;g/mL.
topic sea cucumbers
holothurians
saponins
triterpene glycosides
LC-MS/MS
molecular networking
cytotoxic activity
url https://www.mdpi.com/1660-3397/17/2/86
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