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New antimalarial and antimicrobial tryptamine derivatives from the marine sponge Fascaplysinopsis reticulata
Campos, P.-E.; Pichon, E.; Moriou, C.; Clerc, P.; Trépos, R.; Frederich, M.; De Voogd, N.; Hellio, C.; Gauvin-Bialecki, A.; Al-Mourabit, A. (2019). New antimalarial and antimicrobial tryptamine derivatives from the marine sponge Fascaplysinopsis reticulata. Mar. Drugs 17(3): 167. https://dx.doi.org/10.3390/md17030167
In: Marine Drugs. Molecular Diversity Preservation International (MDPI): Basel. ISSN 1660-3397; e-ISSN 1660-3397, more
Peer reviewed article  
Available in  Authors 
Keywords
    Fascaplysinopsis reticulata (Hentschel, 1912) [WoRMS]; Porifera [WoRMS]
    Marine/Coastal
Author keywords
    Fascaplysinopsis reticulata; marine sponge; tryptamine alkaloids;antimalarial activity; antimicrobial activity
Authors  Top 
  • Campos, P.-E.
  • Pichon, E.
  • Moriou, C.
  • Clerc, P.
  • Trépos, R.
  • Frederich, M., more
  • De Voogd, N., more
  • Hellio, C.
  • Gauvin-Bialecki, A.
  • Al-Mourabit, A.
Abstract
    Chemical study of the CH2Cl2-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6′-bis-(debromo)-gelliusine F (1), 6-bromo-8,1′-dihydro-isoplysin A (2) and 5,6-dibromo-8,1′-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7). 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 (2) and (3), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 µg/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (6) and (Z)-6-bromo-2′-demethyl-3′-N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 µg/mL, respectively.
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