Marine Natural Products with Bioactivity Against Neglected Tropical Diseases

Kokkaliari, Sofia; Avalon, Nicole E.; Herrera, Kristin; Young, Ryan M.; Welsch, Joshua; Yang, Bingjie; Dietrick, Sarah G.; Baker, Bill J.

doi:10.1007/7081_2021_56

Cited by 1 publication

(2 citation statements)

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“…These metabolites showed identical NMR and mass spectrometry (MS) experim data (see Supplementary Material). However, they exhibit opposite optical rotation equal magnitude: [α] 20 D +80 (c 0.20, CHCl3) and [α] 20 D −80 (c 0.20, CHCl3) for compou and 2, respectively. These data confirm that it is the enantiomers dextrorotatory or ( levorotatory or (-) of elatol (2).…”

Section: Chamigrane-type Sesquiterpenes From Laurencia Dendroideamentioning

confidence: 99%

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Chamigrane-Type Sesquiterpenes from Laurencia dendroidea as Lead Compounds against Naegleria fowleri

et al. 2023

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Naegleria fowleri is an opportunistic protozoon that can be found in warm water bodies. It is the causative agent of the primary amoebic meningoencephalitis. Focused on our interest to develop promising lead structures for the development of antiparasitic agents, this study was aimed at identifying new anti-Naegleria marine natural products from a collection of chamigrane-type sesquiterpenes with structural variety in the levels of saturation, halogenation and oxygenation isolated from Laurencia dendroidea. (+)-Elatol (1) was the most active compound against Naegleria fowleri trophozoites with IC50 values of 1.08 μM against the ATCC 30808™ strain and 1.14 μM against the ATCC 30215™ strain. Furthermore, the activity of (+)-elatol (1) against the resistant stage of N. fowleri was also assessed, showing great cysticidal properties with a very similar IC50 value (1.14 µM) to the one obtained for the trophozoite stage. Moreover, at low concentrations (+)-elatol (1) showed no toxic effect towards murine macrophages and could induce the appearance of different cellular events related to the programmed cell death, such as an increase of the plasma membrane permeability, reactive oxygen species overproduction, mitochondrial malfunction or chromatin condensation. Its enantiomer (−)-elatol (2) was shown to be 34-fold less potent with an IC50 of 36.77 μM and 38.03 μM. An analysis of the structure–activity relationship suggests that dehalogenation leads to a significant decrease of activity. The lipophilic character of these compounds is an essential property to cross the blood-brain barrier, therefore they represent interesting chemical scaffolds to develop new drugs.

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Section: Chamigrane-type Sesquiterpenes From Laurencia Dendroideamentioning

confidence: 99%

“…The natural and marine environments are a potential source of structurally diverse and biologically active secondary metabolites that offer the opportunity to design antiprotozoal drugs [18][19][20]. Particularly, the marine macroalgae are considered as a promising source of novel biochemically active compounds against protozoa.…”

Section: Introductionmentioning

confidence: 99%