Mar. Drugs 2019, 17(2), 86; https://doi.org/10.3390/md17020086
Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber Holothuria atra
Laura Grauso 1
, Afsaneh Yegdaneh 2, Mohsen Sharifi 2, Alfonso Mangoni 3, Behzad Zolfaghari 2 and Virginia Lanzotti 1,*
, Afsaneh Yegdaneh 2, Mohsen Sharifi 2, Alfonso Mangoni 3, Behzad Zolfaghari 2 and Virginia Lanzotti 1,*
1
Dipartimento di Agraria, Università di Napoli Federico II, Via Università 100, 80055 Portici (NA), Italy
2
Department of Pharmacognosy, School of Pharmacy, Isfahan University of Medical Sciences, Hezar-Jerib Ave., 81746 73461 Isfahan, Iran
3
Dipartimento di Farmacia, Università di Napoli Federico II, Via Domenico Montesano 49, 80131 Napoli, Italy
*
Author to whom correspondence should be addressed.
Received: 24 December 2018 / Revised: 15 January 2019 / Accepted: 24 January 2019 / Published: 1 February 2019
(This article belongs to the Special Issue Selected Papers from the 4th Sino–Italian Symposium on Bioactive Natural Products)
Abstract
The saponin composition of a specimen of black sea cucumber, Holothuria atra 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 Holothuria atra turned out to be more complex than previously reported. The most abundant saponins in the extract (1–4) were isolated and characterized by 1D- and 2D-NMR experiments. Compound 1 was identified as a new triterpene glycoside saponin, holothurin A5. The side chain of the new saponin 1, 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 1–4, evaluated on the human cervix carcinoma HeLa cell line, was remarkable, with IC50 values ranging from 1.2 to 2.5 µg/mL. View Full-TextKeywords:
sea cucumbers; holothurians; saponins; triterpene glycosides; LC-MS/MS; molecular networking; cytotoxic activity
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Grauso, L.; Yegdaneh, A.; Sharifi, M.; Mangoni, A.; Zolfaghari, B.; Lanzotti, V. Molecular Networking-Based Analysis of Cytotoxic Saponins from Sea Cucumber Holothuria atra. Mar. Drugs 2019, 17, 86.
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