Anti- Acanthamoeba Activity of Brominated Sesquiterpenes from Laurencia johnstonii

• Published in: Marine drugs Vol. 16; no. 11; p. 443
• Main Authors: García-Davis, Sara, Sifaoui, Ines, Reyes-Batlle, María, Viveros-Valdez, Ezequiel, Piñero, José E, Lorenzo-Morales, Jacob, Fernández, José J, Díaz-Marrero, Ana R
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 11.11.2018; MDPI
• Subjects: 3-bromojohnstane; Acanthamoeba; Acanthamoeba castellanii - drug effects; anti-amoeboid activity; Antiparasitic Agents - chemistry; Antiparasitic Agents - isolation & purification; Antiparasitic Agents - pharmacology; Aquatic Organisms - chemistry; Bio-assays; Bioassays; Biological activity; Biological Assay - methods; brominated sesquiterpene; Bromination; Carbon; Cysts; Diastereoisomers; Fractionation; Halogenation; Inhibitory Concentration 50; johnstane; Laurencia; Laurencia - chemistry; Laurencia johnstonii; marine natural products; Mass spectrometry; Metabolites; Mexico; Molecular Structure; Natural products; Parasites; Scientific imaging; Sesquiterpenes; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; Stereoisomerism; Structure-Activity Relationship; Mexico; brominated sesquiterpene; Laurencia johnstonii; 3-bromojohnstane; Acanthamoeba; anti-amoeboid activity; marine natural products; johnstane
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md16110443

Focused on our interest to develop novel antiparasistic agents, the present study was aimed to evaluate the biological activity of an extract of collected in Baja California Sur, Mexico, against an Neff strain. Bioassay-guided fractionation allowed us to identify the amoebicidal diastereoisomers α-bromocuparane ( ) and α-isobromocuparane ( ). Furthermore, bromination of the inactive laurinterol ( ) and isolaurinterol ( ) yielded four halogenated derivatives, ( )⁻( ), which improved the activity of the natural sesquiterpenes. Among them, the most active compound was 3α-bromojohnstane ( ), a sesquiterpene derivative which possesses a novel carbon skeleton johnstane.