New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata

• Published in: Marine drugs Vol. 17; no. 3; p. 167
• Main Authors: Campos, Pierre-Eric, Pichon, Emmanuel, Moriou, Céline, Clerc, Patricia, Trépos, Rozenn, Frederich, Michel, De Voogd, Nicole, Hellio, Claire, Gauvin-Bialecki, Anne, Al-Mourabit, Ali
• Format: Journal Article Web Resource
• Language: English
• Published: Switzerland MDPI AG 15.03.2019; MDPI; NLM (Medline)
• Subjects: Analytical chemistry; Antiinfectives and antibacterials; antimalarial activity; Antimalarial agents; antimicrobial activity; Antimicrobial agents; Antiprotozoal agents; Bacteria; Biodiversity and Ecology; Biofilms; Carbon; Chemical Sciences; Dichloromethane; Disease resistance; Environmental Sciences; Fascaplysinopsis; Fascaplysinopsis reticulata; Human health sciences; Marine chemistry; Marine invertebrates; marine sponge; Medicinal Chemistry; Metabolites; Minimum inhibitory concentration; NMR; Nuclear magnetic resonance; Organic chemistry; Pharmacie, pharmacologie & toxicologie; Pharmacy, pharmacology & toxicology; Sciences de la santé humaine; Tryptamine; tryptamine alkaloids; Tryptamines; Tryptophan; Fiji; marine sponge; tryptamine alkaloids; antimicrobial activity; antimalarial activity; Fascaplysinopsis reticulata; ACL
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md17030167

Chemical study of the CH₂Cl₂-MeOH (1:1) extract of the sponge collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6'-bis-(debromo)-gelliusine F ( ), 6-bromo-8,1'-dihydro-isoplysin A ( ) and 5,6-dibromo-8,1'-dihydro-isoplysin A ( ), along with the synthetically known 8-oxo-tryptamine ( ) and the three known molecules from the same family, tryptamine ( ), ( )-6-bromo-2'-demethyl-3'- -methylaplysinopsin ( ) and ( )-6-bromo-2'-demethyl-3'- -methylaplysinopsin ( ). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are ( ) and ( ), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards , and ( ), with MIC values of 1 µg/mL towards . In addition the known 8-oxo-tryptamine ( ) and the mixture of the ( )-6-bromo-2'-demethyl-3'- -methylaplysinopsin ( ) and ( )-6-bromo-2'-demethyl-3'- -methylaplysinopsin ( ) showed moderate antiplasmodial activity against with IC values of 8.8 and 8.0 µg/mL, respectively.