Novel Halogenated Metabolites from the Malaysian Laurencia pannosa

Suzuki, Minoru; Daitoh, Motonari; Vairappan, Charles Santhanaraju; Abe, Tsuyoshi; Masuda, Michio

doi:10.1021/np0006317

Cited by 48 publications

(35 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…L. gracilis [103], and isolaurenisol (176), obtained initially from Laurencia distichophylla [264], to avoid confusion due to the rather similar common names given. In addition to monomeric cyclolauranes, three dimeric derivatives (238)(239)(240) have been reported to date from various Laurencia species. Metabolites 241-245 feature a rearranged laurane skeleton arising from a methyl migration from C-1 to C-2, while laurentristich-4-ol (246), isolated from a Chinese Laurencia tristicha [232,315], possesses an irregular isoprenoid carbocycle, proposed biogenetically to result from the rearrangement of cyclolaurane skeleton.…”

Section: Chamigranes and Related Sesquiterpenesmentioning

confidence: 99%

“…The antibacterial and/or antifungal activities of the acetogenins laurenmariallene (741) [74], chinzallene (749) [105], (12E)-lembyne A (759) [62], lembyne A (763) [165], (3Z)-laurenyne (798) [513], (Z)-chondriol (803) [878], ent-854 [152], desepilaurallene (862) [152], and (3Z )-chlorofucin (875) [238] have also been evaluated in a number of studies.…”

Section: Antibacterial and Antifungal Activitymentioning

confidence: 99%

See 1 more Smart Citation

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

View full text Add to dashboard Cite

Nature, the most prolific source of biological and chemical diversity, has provided mankind with treatments for health problems since ancient times and continues to be the most promising reservoir of bioactive chemicals for the development of modern drugs. In addition to the terrestrial organisms that still remain a promising source of new bioactive metabolites, the marine environment, covering approximately 70% of the Earth's surface and containing a largely unexplored biodiversity, offers an enormous resource for the discovery of novel compounds. According to the MarinLit database, more than 27,000 metabolites from marine macro- and microorganisms have been isolated to date providing material and key structures for the development of new products in the pharmaceutical, food, cosmeceutical, chemical, and agrochemical sectors. Algae, which thrive in the euphotic zone, were among the first marine organisms that were investigated as sources of food, nutritional supplements, soil fertilizers, and bioactive metabolites.Red algae of the genus Laurencia are accepted unanimously as one of the richest sources of new secondary metabolites. Their cosmopolitan distribution, along with the chemical variation influenced to a significant degree by environmental and genetic factors, have resulted in an endless parade of metabolites, often featuring multiple halogenation sites.The present contribution, covering the literature until August 2015, offers a comprehensive view of the chemical wealth and the taxonomic problems currently impeding chemical and biological investigations of the genus Laurencia. Since mollusks feeding on Laurencia are, in many cases, bioaccumulating, and utilize algal metabolites as chemical weaponry against natural enemies, metabolites of postulated dietary origin of sea hares that feed on Laurencia species are also included in the present review. Altogether, 1047 secondary metabolites, often featuring new carbocyclic skeletons, have been included.The chapter addresses: (1) the "Laurencia complex", the botanical description and the growth and population dynamics of the genus, as well as its chemical diversity and ecological relations; (2) the secondary metabolites, which are organized according to their chemical structures and are classified into sesquiterpenes, diterpenes, triterpenes, acetogenins, indoles, aromatic compounds, steroids, and miscellaneous compounds, as well as their sources of isolation which are depicted in tabulated form, and (3) the biological activity organized according to the biological target and the ecological functions of Laurencia metabolites.

show abstract

Section: Chamigranes and Related Sesquiterpenesmentioning

confidence: 99%

Section: Antibacterial and Antifungal Activitymentioning

confidence: 99%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products

View full text Add to dashboard Cite

show abstract

“…Vários estudos têm sido realizados com o objetivo de verificar a atividade antibacteriana e antifúngica dos metabólitos secundários de Laurencia (Bansemir, 2004 (Suzuki et al, 2001). O sesquiterpeno alolaurinterol (43) foi isolado com um rendimento de 33,5% a partir do extrato bruto de Laurencia obtusa coletada na ilha caribenha de Dominica.…”

Section: Atividade Antitumoralunclassified

Atividade biológica de metabólitos secundários de algas marinhas do gênero Laurencia

Machado¹,

Kaiser²,

Costa³

et al. 2010

Rev. bras. farmacogn.

View full text Add to dashboard Cite

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.

show abstract

“…L. pannosa from Malaysia was the source of two halogenated chamigranes with unusual rearranged framework named pannosanol (43) and pannosane (44). Both compounds showed antibacterial activities [49]. The rearranged chamigrane Scopariol (45), the β-chamigrene isorigidol (46) and the geometric isomers (+)-3-(Z)-bromomethylidene-10 β -bromo-β -chamigrene and (-)-3-(E)-bromomethylidene-10 β -bromo-β -chamigrene (47, 48) were reported from L. scoparia collected in Brazilian waters.…”

Section: Introductionmentioning

confidence: 99%

“…Compound 46 and ma'ilione (49), previously isolated from L.cartilaginea [50] exhibited moderate in vitro anthelmintic activity against the parasitant stage of Nippostrongylus brasiliensis [17]. From L. scoparia and in a separate report, Suescun et al isolated and established the absolute stereochemistry of isorigidol (46) and ma'ilione (49) by an X-ray crystal as (3R,6S,9S,10S) and (6S,9R,10S) respectively [51]. Ma'iliohydrin (50), a cytotoxic tribrominated chamigrene with dibromohydrin functionality from a Laurencia sp.…”

Section: Introductionmentioning

confidence: 99%

Phytochemical and Biological Properties of Sesquiterpene Constituents From the Marine Red Seaweed Laurencia: A Review

Al-Massarani¹

2014

Nat Prod Chem Res 2014

View full text Add to dashboard Cite

Novel Halogenated Metabolites from the Malaysian Laurencia pannosa

Cited by 48 publications

References 26 publications

The Laurencia Paradox: An Endless Source of Chemodiversity

The Laurencia Paradox: An Endless Source of Chemodiversity

Atividade biológica de metabólitos secundários de algas marinhas do gênero Laurencia

Phytochemical and Biological Properties of Sesquiterpene Constituents From the Marine Red Seaweed Laurencia: A Review

Contact Info

Product

Resources

About