Sesquiterpenes from the essential oil of Laurencia dendroidea (Ceramiales, Rhodophyta): isolation, biological activities and distribution among seaweeds

Gressler, Vanessa; Stein, Erika Mattos; Dörr, Fabiane; Fujii, Mutuê T.; Colepicolo, Pio; Pinto, Ernani

doi:10.1590/s0102-695x2011005000059

Cited by 41 publications

(27 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although the presence of sesquiterpenes was not expected in this group, triquinane alcohols (compounds 47 and 26) were found in P. perforata by using a high sensitivity extraction method (HS-SPME) (Gressler et al, 2011). These compounds were not active against bacterial strains or the yeast Candida albicans, but showed some antioxidant activity.…”

Section: Resultsmentioning

confidence: 84%

Overview of the taxonomy and of the major secondary metabolites and their biological activities related to human health of the Laurencia complex (Ceramiales, Rhodophyta) from Brazil

Fujii¹,

Cassano²,

Stein³

et al. 2011

Rev. bras. farmacogn.

Self Cite

View full text Add to dashboard Cite

Abstract:In Brazil, the Laurencia complex is represented by twenty taxa: Laurencia s.s. with twelve species, Palisada with four species (including Chondrophycus furcatus now that the proposal of its transference to Palisada is in process), and Osmundea and Yuzurua with two species each. The majority of the Brazilian species of the Laurencia complex have been phylogenetically analyzed by 54 rbcL sequences, including five other Rhodomelacean species as outgroups. The analysis showed that the Laurencia complex is monophyletic with high posterior probability value. The complex was separated into five clades, corresponding to the genera: Chondrophycus, Laurencia, Osmundea, Palisada, and Yuzurua. A bibliographical survey of the terpenoids produced by Brazilian species showed that only six species of Laurencia and five of Palisada (including C. furcatcus) have been submitted to chemical analysis with 48 terpenoids (47 sesquiterpenes and one triterpene) isolated. No diterpenes were found. Of the total, 23 sesquiterpenes belong to the bisabolane class and eighteen to the chamigrene type, whose biochemical precursor is bisabolane, two are derived from lauranes and four are triquinols. Despite the considerable number of known terpenes and their ecological and pharmacological importance, few experimental biological studies have been performed. In this review, only bioactivities related to human health were considered.

show abstract

Section: Resultsmentioning

confidence: 84%

Overview of the taxonomy and of the major secondary metabolites and their biological activities related to human health of the Laurencia complex (Ceramiales, Rhodophyta) from Brazil

Fujii¹,

Cassano²,

Stein³

et al. 2011

Rev. bras. farmacogn.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Aplysin (195) has shown a protective effect on hepatic injury induced by ethanol in rats [893]. The triquinanes 490 and 492 exhibited weak antioxidant activity when evaluated in the DPPH radical-scavenging assay [458]. The diterpenes parguerol (514) and isoparguerol (540) induced neurite outgrowth in rat pheochromocytoma (PC-12) cells at concentrations of 25 and 50 μM, respectively, while deoxyparguerol 7,16-acetate (651) was proven inactive even at a 100 μM concentration [478].…”

Section: Miscellaneous Biological Activitiesmentioning

confidence: 99%

The Laurencia Paradox: An Endless Source of Chemodiversity

Harizani

Iοannou

Roussis

2016

Progress in the Chemistry of Organic Natural Products 102

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

“…As previous reported by Gressler et al (2011), the sesquiterpenes 7-epi-silphiperfolan-6β-ol and silphiperfolan-7β-ol have the same retention time and the identifications were done by the comparison of the mass spectral overlap obtained with laboratory standards of both compounds and by the individual KI. Table 1 shows the composition of L. dendroidea in more details.…”

Section: Analysis Of the Volatile Compoundsmentioning

confidence: 99%

“…The antioxidant profile of both extracts by the two methods is shown in Figure 1. The antimicrobial and antioxidant activities of the essential oil of L. dendroidea have already been published (Gressler et al, 2011).…”

Section: Antimicrobial and Antioxidant Activitiesmentioning

confidence: 99%

Characterization of volatile composition of Laurencia dendroidea by gas chromatography-mass spectrometry

Gressler

Fujii

Colepicolo

et al. 2012

Rev. bras. farmacogn.

Self Cite

View full text Add to dashboard Cite

Abstract:In this study we report the characterization of the volatile compounds of Laurencia dendroidea. Solvent extracts (dichloromethane and methanol), hydrodistillation extracts and headspace solid-phase microextraction samples were obtained and analyzed by GC-MS. Forty-six volatile components were identifi ed in L. dendroidea, among them hydrocarbons, alcohols, phenols, aldehydes, ketones, acids, esters and terpenes.

show abstract

Sesquiterpenes from the essential oil of Laurencia dendroidea (Ceramiales, Rhodophyta): isolation, biological activities and distribution among seaweeds

Cited by 41 publications

References 17 publications

Overview of the taxonomy and of the major secondary metabolites and their biological activities related to human health of the Laurencia complex (Ceramiales, Rhodophyta) from Brazil

Overview of the taxonomy and of the major secondary metabolites and their biological activities related to human health of the Laurencia complex (Ceramiales, Rhodophyta) from Brazil

The Laurencia Paradox: An Endless Source of Chemodiversity

Characterization of volatile composition of Laurencia dendroidea by gas chromatography-mass spectrometry

Contact Info

Product

Resources

About