New Sesquiterpene Derivatives from the Red Alga Laurencia scoparia. Isolation, Structure Determination, and Anthelmintic Activity

Davyt, Danilo; Fernández, Rafael; Suescun, Leopoldo; Mombrú, Álvaro W.; Saldaña, Jenny; Domínguez, Laura; Coll, J; Fujii, Mutuê T.; Manta, Eduardo

doi:10.1021/np0102307

Cited by 99 publications

(73 citation statements)

References 21 publications

(38 reference statements)

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“…These secondary metabolites provide defense against herbivores (Pereira et al, 2004b;Lima et al, 2008), fouling organisms (Da Gama et al, 2008) and pathogens (Paul & Ritson-Williams, 2008); they also play a role in reproduction (Amsler & Fairhead, 2005), protection from UV radiation (Gomez et al, 1998) and as allelopathic agents (Beach et al, 2003). These compounds have shown some interesting pharmacological activities such as: antitumoral (Barbier et al, 2001), antiparasitic (Davyt et al, 2001), antibacterial (Vairappan, 2003), antiviral (Santos et al, 1999;Pereira et al, 2004a;Soares et al, 2007), antioxidant (Nahas et al, 2007), and antifungal activity (de Oliveira et al, 2008). In particular, antiviral effects of sulfated polysaccharides and terpenes against a variety of enveloped viruses, such as Herpes Simplex Virus type 1 (HSV-1) and 2 (HSV-2), Human Immunodefi ciency Virus (HIV), human cytomegalovirus, dengue viruses, respiratory syncytial and infl uenza viruses have been reported (Laillea et al, 1998;Ghosh et al, 2004;Cirne-Santos et al, 2008;Hidari et al, 2008).…”

Section: Introductionmentioning

confidence: 99%

Antiviral activity of extracts from Brazilian seaweeds against herpes simplex virus

Soares¹,

Robaina²,

Mendes³

et al. 2012

Rev. bras. farmacogn.

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Organic extracts of 36 species of marine algae (sixteen species of Rhodophyta, eight species of Ochrophyta and twelve species of Chlorophyta) from seven locations on the Brazilian coast were evaluated for their anti-HSV-1 and anti-HSV-2 activity resistant to Acyclovir (ACV). Activity tests in crude extracts, followed by the identification of the major compounds present, were performed for all species. The chemical profiles of all crude extracts were obtained by 1 H-NMR and 13 C-NMR spectroscopy. The percentage of extracts with antiviral activity was higher for HSV-1 (86.1%) than for HSV-2 (55.5%). The green algae Ulva fasciata and Codium decorticatum both showed the highest activity (99.9%) against HSV-1, with triacylglycerols and fatty acids as the major components. The red alga Laurencia dendroidea showed good activity against HSV-1 (97.5%) and the halogenated sesquiterpenes obtusol and (-)-elatol were identified as the major components in the extract. Against HSV-2, the green alga Penicillus capitatus (Chlorophyta) and Stypopodium zonale (Ochrophyta) were the most active (96.0 and 95.8%). Atomaric acid, a meroditerpene, was identified as the major secondary metabolite in the S. zonale extract. These results reinforce the role of seaweeds as important sources of compounds with the potential to enter into the pipeline for development of new drugs against herpes simplex.

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Section: Introductionmentioning

confidence: 99%

Antiviral activity of extracts from Brazilian seaweeds against herpes simplex virus

Soares¹,

Robaina²,

Mendes³

et al. 2012

Rev. bras. farmacogn.

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“…A rearranged chamigrane sesquiterpene 20 possessing the brine shrimp toxicity (LC 50 51.1 lg/mL) was obtained from Chinese L. composita, and its relative configuration was confirmed by a combination of NOE correlations and quantum chemical calculations of the energy-minimized conformer (Li et al 2012a). Scopariol (21) with a rearranged chamigrane skeleton was identified from Brazilian L. scoparia, which demonstrated no effect on the parasitant stage of Nippostrongylus brasiliensis (Davyt et al 2001). Based the high degrees (at least five) of unsaturation and the key role of bromonium ion in the assembly of chamigrane backbone (Wang et al 2013 (52), and rearranged laurane (53 and 54) members from ten Laurencia species.…”

Section: Brasilanesmentioning

confidence: 98%

Nonhalogenated organic molecules from Laurencia algae

Wang

2013

Phytochem Rev

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The marine red algae of the genus Laurencia have produced more 700 secondary metabolites and exhibited high molecular diversity and intriguing bioactivity. Since the halogenated structures have been comprehensively reviewed previously, this review, covering up to the end of 2012, mainly focuses on the source, structure elucidation, and bioactivity of nonhalogenated organic molecules from Laurencia spp. as well as the relationship between nonhalogenated and halogenated products. Overall, 173 new or new naturally occurring compounds with 58 skeletons, mainly including sesquiterpenes, diterpenes, triterpenes, and C 15 -acetogenins, are described.

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“…Entretanto, nenhuma das substâncias testadas foi mais potente que o fármaco utilizado como referência, albendazol (Davyt, 2001). Posteriormente, foi relatado o isolamento de um sesquiterpeno do tipo β-bisaboleno 64 a partir da mesma espécie, proveniente do mesmo local de coleta.…”

Section: Atividade Antiparasitáriaunclassified

Atividade biológica de metabólitos secundários de algas marinhas do gênero Laurencia

Machado¹,

Kaiser²,

Costa³

et al. 2010

Rev. bras. farmacogn.

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RESUMO:As algas vermelhas do gênero Laurencia são conhecidas como uma riquíssima fonte de metabólitos secundários. As principais classes químicas já isoladas são terpenos -sesquiterpenos, diterpenos, triterpenos -e acetogeninas. Estudos apontam que estas substâncias apresentam importantes atividades biológicas, principalmente citotóxica e antibacteriana. Existem ainda alguns poucos trabalhos com informações sobre atividade antiparasitária, antiviral e antifúngica dos metabólitos de Laurencia. O forte perfil bioativo observado em alguns estudos sugere que alguns destes metabólitos podem ser futuramente utilizados como fármacos ou como protótipos de novos agentes antitumorais e antibacterianos. Muitos dos metabólitos de Laurencia ainda não foram avaliados sob o ponto de vista farmacológico, o que representa um grande potencial a ser explorado por diversos campos da farmacologia.Unitermos: macroalgas, Ceramiales, Rhodomelaceae, produtos naturais.ABSTRACT: "Biological activity of the secondary metabolite from marine algae of the genus Laurencia." The red alga of the genus Laurencia is known as an endless source of metabolites. The main substances produced are sesquiterpenes, diterpenes, triterpenes and acetogenins. Many studies reveal that these metabolites are active, especially cytotoxic and antibacterial. There are few other studies that describe the antiparasital, antifungal and antiviral actions of the metabolites produced by the alga of the genus Laurencia. The results observed in some studies suggest that these metabolites may be used in the future as drugs or lead compounds as antitumoral and/or antibacterial agents. Many metabolites have not been submitted to pharmacological studies which still represents an area to be explored.

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New Sesquiterpene Derivatives from the Red Alga Laurencia scoparia. Isolation, Structure Determination, and Anthelmintic Activity

Cited by 99 publications

References 21 publications

Antiviral activity of extracts from Brazilian seaweeds against herpes simplex virus

Antiviral activity of extracts from Brazilian seaweeds against herpes simplex virus

Nonhalogenated organic molecules from Laurencia algae

Atividade biológica de metabólitos secundários de algas marinhas do gênero Laurencia

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