Isolation of naturally occurring dactylomelane metabolites as Laurencia constituents

Fernández, José J.; Souto, Marı́a L.; Gil, Laura V.; Norte, Manuel

doi:10.1016/j.tet.2005.07.024

Cited by 28 publications

(34 citation statements)

References 8 publications

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“…The first one is the nonterpenoid group, which contains the acetogenins derived from the metabolism of fatty acids. The other one is the terpenoid group, in which the sesquiterpenes are the most abundant, but also containing diterpenes and triterpenes (Fernández et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

“…The prominent biological activity of marine terpenes is evident in their ecological role in the marine environment and makes them interesting as potential drugs. Many of these natural products are pharmacologically active and marine algae, especially those from tropical and subtropical seas, are able to produce a wide range of compounds, many of which exhibit at least some degree of bioactivity (Fernández et al, 1998(Fernández et al, , 2005da Gama et al, 2002;Cassano et al, 2008;Lhullier et al, 2009;Machado et al, 2011;Santos et al, 2010). In fact, the marine environment represents a treasure trove of useful products awaiting discovery for the treatment of infectious and parasitic diseases (Vairappan et al, 2004;Morales et al, 2006), cancer (Mohammed et al, 2004;Stein et al, 2011), cognitive diseases, inflammatory processes, and viral infections (Sakemi et al, 1986).…”

Section: Introductionmentioning

confidence: 99%

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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.

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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.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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.

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“…Two rare 10,15-cyclophytane-type diterpenes, viridiols A (97) and B (98), were obtained from L. viridis (Canary Islands), which showed remarkable activity against P388, A549, HT-29, and MEL-28 tumor cells with IC 50 values of 1-2.5 lg/mL (Gil-Rodriguez and Haroun 1992; Norte et al 1996). Six dactylomelane diterpenes 99-104 occurred in an unidentified Laurencia species collected from Canary Islands, which were deduced to be formed via a bromonium ion intermediate in biogenesis (Fernández et al 2005). A diterpene hydroperoxide 105 with a novel framework was reported from L. snyderiae (Catalina Island), which was proposed to be derived from the debromination and rearrangement of its brominated precursor (Howard et al 1977).…”

Section: Nonhalogenated Diterpenesmentioning

confidence: 99%

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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“…The fi rst one is the nonterpenoid group, which contains the acetogenins derived from the metabolism of fatty acids. The other one is the terpenoid group, in which the sesquiterpenes are the most abundant, but also containing diterpenes and triterpenes (Pereira & Teixeira, 1999;Fernández et al, 2005;Cen-Pacheco et al, 2011a).…”

Section: Introductionmentioning

confidence: 99%

“…Many marine algae, especially those from tropical and subtropical seas, are able to produce a wide range of compounds, many of which exhibit at least some degree of bioactivity (Fernández et al, 1998(Fernández et al, , 2005Da Gama et al, 2002;Cassano et al, 2008a;Lhullier et al, 2009;Santos et al, 2010;Machado et al, 2011;Stein et al, 2011a, b).…”

Section: Introductionmentioning

confidence: 99%

Comparative analysis of the corps en cerise in several species of Laurencia (Ceramiales, Rhodophyta) from the Atlantic Ocean

Fujii¹,

Cassano

Sentíes³

et al. 2012

Rev. bras. farmacogn.

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Different species of Laurencia have proven to be a rich source of natural products yielding interesting bioactive halogenated secondary metabolites, such as terpenoids and acetogenins. It is shown that such compounds are accumulated in the spherical, reniform to claviform refractive inclusions called corps en cerise (CC), which are intensively osmiophilic and located mainly in the cortical cells of the thalli and also in trichoblast cells. Up to now, it was believed that CC were present only in these two kinds of cells. Recently, however, a species of Laurencia, L. marilzae, with CC in all cells of the thallus, i.e., cortical, medullary, including the pericentral and axial cells, as well as in the trichoblasts, was described from the Canary Islands, and subsequently also reported to Brazil and Mexico. Within the Laurencia complex, only Laurencia species produce CC. Since the species of Laurencia are targets of interest for the prospection of bioactive substances due to their potential antibacterial, antifungal, anticholinesterasic, antileishmanial, cytotoxic, and antioxidant activities, the present paper carries out a comparative analysis of the corps en cerise in several species of Laurencia from the Atlantic Ocean to obtain basic information that can support natural product bioprospection projects. Our results show that the number and size of the CC are constant within a species, independent of the geographical distribution, corroborating their use for taxonomical purposes to differentiate groups of species that present a lower number from those that have a higher number. In this regard, there was a tendency for the number of CC to be higher in some species of Laurencia from the Canary Islands. The presence of CC can also be used to distinguish species in which these organelles are present in all cells of the thallus from those in which CC are restricted to the cortical cells. Among the species analyzed, L. viridis displayed the most varied secondary metabolites composition, such as sesquiterpenes, diterpenes, triterpenes, all of which showed potent antiviral, cytotoxic, and antitumoral activities, including protein phosphatase type 2A (PP2A) inhibitory effects.

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Isolation of naturally occurring dactylomelane metabolites as Laurencia constituents

Cited by 28 publications

References 8 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

Nonhalogenated organic molecules from Laurencia algae

Comparative analysis of the corps en cerise in several species of Laurencia (Ceramiales, Rhodophyta) from the Atlantic Ocean

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