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 ug/mL.

Molecular networking-based analysis of cytotoxic saponins from sea cucumber holothuria atra / Grauso, Laura; Yegdaneh, Afsaneh; Sharifi, Mohsen; Mangoni, Alfonso; Zolfaghari, Behzad; Lanzotti, Virginia. - In: MARINE DRUGS. - ISSN 1660-3397. - 17:2(2019), p. 86. [10.3390/md17020086]

Molecular networking-based analysis of cytotoxic saponins from sea cucumber holothuria atra

Grauso, Laura
Primo
;
Mangoni, Alfonso;Lanzotti, Virginia
Ultimo
2019

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 ug/mL.
2019
Molecular networking-based analysis of cytotoxic saponins from sea cucumber holothuria atra / Grauso, Laura; Yegdaneh, Afsaneh; Sharifi, Mohsen; Mangoni, Alfonso; Zolfaghari, Behzad; Lanzotti, Virginia. - In: MARINE DRUGS. - ISSN 1660-3397. - 17:2(2019), p. 86. [10.3390/md17020086]
File in questo prodotto:
File Dimensione Formato  
MarineDrugs2019_Holo.pdf

accesso aperto

Descrizione: Articolo principale
Licenza: Creative commons
Dimensione 2.18 MB
Formato Adobe PDF
2.18 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/739809
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 32
  • ???jsp.display-item.citation.isi??? 23
social impact