Chemical diversity and antileishmanial activity of crude extracts of Laurencia complex (Ceramiales, Rhodophyta) from Brazil

Machado, Fernanda Lacerda da Silva; Lima, Wallace Pacienza; Duarte, Heitor Monteiro; Rossi-Bergmann, Bartira; Gestinari, Lísia Mônica de Souza; Fujii, Mutuê T.; Kaiser, Carlos R.; Soares, Angélica Ribeiro

doi:10.1016/j.bjp.2014.10.009

Cited by 7 publications

(3 citation statements)

References 35 publications

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“…The distinct larvicidal activities observed suggest the existence of qualitative and/or quantitative differences in metabolite content between locations [ 46 , 47 , 48 ]. Further GC-MS analysis revealed that both extracts displayed the same major compounds.…”

Section: Resultsmentioning

confidence: 99%

Larvicidal Potential of the Halogenated Sesquiterpene (+)-Obtusol, Isolated from the Alga Laurencia dendroidea J. Agardh (Ceramiales: Rhodomelaceae), against the Dengue Vector Mosquito Aedes aegypti (Linnaeus) (Diptera: Culicidae)

et al. 2016

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Dengue is considered a serious public health problem in many tropical regions of the world including Brazil. At the moment, there is no viable alternative to reduce dengue infections other than controlling the insect vector, Aedes aegypti Linnaeus. In the continuing search for new sources of chemicals targeted at vector control, natural products are a promising alternative to synthetic pesticides. In our work, we investigated the toxicity of a bioactive compound extracted from the red alga Laurencia dendroidea J. Agardh. The initial results demonstrated that crude extracts, at a concentration of 5 ppm, caused pronounced mortality of second instar A. aegypti larvae. Two molecules, identified as (−)-elatol and (+)-obtusol were subsequently isolated from crude extract and further evaluated. Assays with (−)-elatol showed moderate larvicidal activity, whereas (+)-obtusol presented higher toxic activity than (−)-elatol, with a LC50 value of 3.5 ppm. Histological analysis of the larvae exposed to (+)-obtusol revealed damage to the intestinal epithelium. Moreover, (+)-obtusol-treated larvae incubated with 2 µM CM-H2DCFDA showed the presence of reactive oxygen species, leading us to suggest that epithelial damage might be related to redox imbalance. These results demonstrate the potential of (+)-obtusol as a larvicide for use against A. aegypti and the possible mode of action of this compound.

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Section: Resultsmentioning

confidence: 99%

Larvicidal Potential of the Halogenated Sesquiterpene (+)-Obtusol, Isolated from the Alga Laurencia dendroidea J. Agardh (Ceramiales: Rhodomelaceae), against the Dengue Vector Mosquito Aedes aegypti (Linnaeus) (Diptera: Culicidae)

et al. 2016

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“…Among all marine macroalgae, the red algae of the genus Laurencia are accepted unanimously as a prolific producer of secondary metabolites, highlighting the sesquiterpenes, diterpenes, triterpenes and C15 acetogenins [22,23]. Many compounds of Laurencia exhibit important antiparasitic properties against several parasites [24][25][26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

“…highlighting the sesquiterpenes, diterpenes, triterpenes and C15 acetogenins [ Many compounds of Laurencia exhibit important antiparasitic properties against s parasites [24][25][26][27][28][29] The sesquiterpenes isolated from the genus Laurencia currently constitute mor 575 structures reported. Among them, the chamigrane-type sesquiterpenes are the frequently occurring class, accounting for approximately 30% of all isolated sesq penes.…”

Section: Introductionmentioning

confidence: 99%

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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Geographic Distribution of Natural Products Produced by the Red Alga Laurencia dendroidea J. Agardh

Machado

Duarte

Gestinari

et al. 2016

Chemistry & Biodiversity

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In order to evaluate the chemical diversity of Laurencia dendroidea J. Agardh, a widely distributed seaweed in Brazilian coast, a phytochemical study was carried out with algae collected from six different locations along the Southeast Brazilian coast. Purified compounds were identified by MS and NMR techniques. The chemical profiles of lipophilic extracts were obtained by GC/MS for each population. In total, 15 compounds were described. The sesquiterpene composition accounted for 49 - 63% of the GC/MS chromatogram area. The discrimination of three chemotypes was done by the use of HCA on GC/MS chromatograms. They were also analyzed by the PCA and, together with peak area analysis, it was possible to discriminate all populations by the main variation of elatol, obtusol, rogiolol, and triquinane. The results revealed the high diversity of sesquiterpene composition among populations of L. dendroidea. Curiously, the within and among population variation of elatol and obtusol suggested a biochemical interplay on the content of these compounds. More studies are necessary to understand the patterns of chemical diversity and compound variation within and among populations of L. dendroidea.

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Chemical diversity and antileishmanial activity of crude extracts of Laurencia complex (Ceramiales, Rhodophyta) from Brazil

Cited by 7 publications

References 35 publications

Larvicidal Potential of the Halogenated Sesquiterpene (+)-Obtusol, Isolated from the Alga Laurencia dendroidea J. Agardh (Ceramiales: Rhodomelaceae), against the Dengue Vector Mosquito Aedes aegypti (Linnaeus) (Diptera: Culicidae)

Larvicidal Potential of the Halogenated Sesquiterpene (+)-Obtusol, Isolated from the Alga Laurencia dendroidea J. Agardh (Ceramiales: Rhodomelaceae), against the Dengue Vector Mosquito Aedes aegypti (Linnaeus) (Diptera: Culicidae)

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

Geographic Distribution of Natural Products Produced by the Red Alga Laurencia dendroidea J. Agardh

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