Poecillastrosides, Steroidal Saponins from the Mediterranean Deep-Sea Sponge Poecillastra compressa (Bowerbank, 1866).
Mar Drugs
; 15(7)2017 Jun 26.
Article
em En
| MEDLINE
| ID: mdl-28672858
ABSTRACT
The first chemical investigation of the Mediterranean deep-sea sponge Poecillastra compressa (Bowerbank, 1866) led to the identification of seven new steroidal saponins named poecillastrosides A-G (1-7). All saponins feature an oxidized methyl at C-18 into a primary alcohol or a carboxylic acid. While poecillastrosides A-D (1-4) all contain an exo double bond at C-24 of the side-chain and two osidic residues connected at O-2', poecillastrosides E-G (5-7) are characterized by a cyclopropane on the side-chain and a connection at O-3' between both sugar units. The chemical structures were elucidated through extensive spectroscopic analysis (High-Resolution Mass Spectrometry (HRESIMS), 1D and 2D NMR) and the absolute configurations of the sugar residues were assigned after acidic hydrolysis and cysteine derivatization followed by LC-HRMS analyses. Poecillastrosides D and E, bearing a carboxylic acid at C-18, were shown to exhibit antifungal activity against Aspergillus fumigatus.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Poríferos
/
Saponinas
Limite:
Animals
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article