Chemotaxonomic study of the diterpenes from the brown alga Dictyota menstrualis

Teixeira, Valéria Laneuville; Cavalcanti, Diana Negrão; Pereira, Renato Crespo

doi:10.1016/s0305-1978(00)00055-7

Cited by 32 publications

(29 citation statements)

References 14 publications

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“…The group of D. dichotoma metabolites that belong to diterpenes was identified by comparison with characteristic EI mass spectra from the literature, but no exact structures were assigned (Fattorusso et al 1976;Teixeira et al 2001;Barbosa et al 2004;Kim et al 2006). Additional experiments were performed with this alga by using coronalone as a JA analogue (Schüler et al 2004).…”

Section: Discussionmentioning

confidence: 99%

“…In addition, the JA mimic coronalone (Schüler et al 2004) was investigated to exclude artefacts due to metabolization of JA in the medium. Special attention was given to the brown alga Dictyota dichotoma for two reasons: (a) this alga is known to exhibit induced defense (Cronin and Hay, 1996), and (b) it is rich in bioactive terpenoids (Fattorusso et al 1976;Teixeira et al 2001;Barbosa et al 2004;), a compound class often involved in induced defense of higher plants. The chemical profiling was paired with bioassays that used herbivores of algae; these assays were conducted to study the role of JA and MeJA as hormones involved in the production of medium-and nonpolar antiherbivore metabolites of brown algae.…”

Section: Introductionmentioning

confidence: 99%

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No Evidence for the Induction of Brown Algal Chemical Defense by the Phytohormones Jasmonic Acid and Methyl Jasmonate

2008

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Induced chemical defense reactions are widespread in marine brown algae. Despite the evidence that the biosynthesis of defense metabolites can be up-regulated upon herbivory, we do not know how this regulation of biosynthetic pathways to secondary metabolites is achieved in brown algae. In higher plants, the phytohormone jasmonic acid (JA) is crucial for the mediation of induced chemical defenses, and several findings of this metabolite from marine sources have been reported. We tested the hypothesis that JA or related metabolites play a role in induced brown algal defense. Quantification of oxylipins with a detection limit around 20 ng g −1 algal tissue did not reveal the presence of JA in the seven examined brown algal species Dictyota dichotoma, Colpomenia peregrina, Ectocarpus fasciculatus, Fucus vesiculosus, Himanthalia elongata, Saccharina latissima (formerly Laminaria saccharina), and Sargassum muticum. Moreover, treatment with ecologically relevant concentrations of JA and methyl jasmonate did not lead to a significant change in the profile of medium-and non-polar metabolites of the tested algae.Only when high concentrations of ≥500 μg ml −1 medium of the phytohormones were applied that a metabolic response which could be attributed to unspecific stress was observed.Bioassays with D. dichotoma that focused on medium-and non-polar compounds confirmed the lack of a biological role of JA and methyl jasmonate in the induction of algal induced chemical defenses. The phytohormone-treated samples did not exhibit any increased defense potential towards the amphipod Ampithoe longimana and the isopod Paracerceis caudata. JA and related phytohormones, known to be active in higher plants, thus appear to play no role in brown algae for induction of the defense chemicals studied here.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

No Evidence for the Induction of Brown Algal Chemical Defense by the Phytohormones Jasmonic Acid and Methyl Jasmonate

2008

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“…Thus, accurately predicting the local concentrations of volatile metabolites released upon tissue disruption, and the concentrations experienced by the feeding herbivore is a major challenge (Pohnert, 2004). Prediction of the actual concentration of defence metabolites during herbivore feeding is further complicated by differences in secondary metabolite concentrations between algae growing in different habitats as well as algae separated by only a few meters (Hay and Steinberg, 1992;Cronin and Hay, 1996b;Sotka et al, 2003;Teixeira et al, 1990;Teixeira et al, 2001;Taylor et al, 2003;Vallim et al, 2005). In addition, the content of secondary metabolites can also vary within one alga (Cronin and Hay, 1996a;Cronin and Hay, 1996b;Pavia et al, 2002;Taylor et al, 2003) and thus only estimated amounts of defence metabolites can be used in bioassays.…”

Section: Resultsmentioning

confidence: 99%

The potential role of wound-activated volatile release in the chemical defence of the brown alga Dictyota dichotoma: Blend recognition by marine herbivores

2007

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Abstract. The chemical defence potential against herbivores of certain Dictyotalean brown algae increases after tissue disruption. This wound activated defence has been explored in bioassays, but the metabolic pathways behind it are unknown. Here we describe a metabolic profiling approach to identify the activated defence metabolites. Before and after tissue damage of Dictyota dichotoma modified diterpenes, non-volatile medium polar metabolites as well as volatile compounds were profiled. While comparison of extracted intact and mechanically wounded algae revealed no significant differences in structure and distribution of semi-volatile and reversed phase LC/MS detectable metabolites, a strong release of gaseous volatiles was observed. Solid phase micro extraction (SPME) and GC/MS were used for identification and quantification of these biogenic gases. This showed that D. dichotoma released elevated amounts of trimethylamine (TMA) and dimethylsulphide (DMS) after mechanical tissue damage. To study the ecological significance of compounds released post injury and of the biosynthetically connected non-volatile acrylate, choice assays were performed with the amphipod Amphithoe longimana. Behavioural assays on artificial diets did not reveal any repellent role for the single isolated metabolites. In strong contrast, a mixture of TMA, DMS and acrylate significantly reduced the association of the herbivores with the treated food pellets. This shows that mixtures of these biogenic gases and acrylate are recognized by the herbivores and influence food selection.

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“…The male and female gametophytes and the sporophyte are identical in appearance. In our previous studies conducted along the Brazilian littoral, it was observed in the field that different haploid-diploid ratios of the alternating life stages of D. menstrualis can be found at the same time in the field throughout the year (Cavalcanti et al 2006;Ortiz-Ramirez et al 2008;Pereira et al 2000;Teixeira et al 2001).…”

Section: Introductionmentioning

confidence: 93%

Variability of a diterpene with potential anti-HIV activity isolated from the Brazilian brown alga Dictyota menstrualis

et al. 2010

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This study evaluated the variability in the production of an HIV-1 antiviral diterpene in individuals of Dictyota menstrualis throughout reproductive stages. The brown alga Dictyota has an isomorphic biphasic life cycle. The quantification of the active principle by GC-FID indicated a greater production of the diterpene in the female gametophytic phase (42.11 ppm). However, these individuals had the highest variation between individuals (standard deviation of 68.20 ppm in the range from 0.39 to 227 ppm). Sporophytic individuals showed less variability. This variability in the production of the antiviral diterpene is important to the development of future antiviral drugs.

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Chemotaxonomic study of the diterpenes from the brown alga Dictyota menstrualis

Cited by 32 publications

References 14 publications

No Evidence for the Induction of Brown Algal Chemical Defense by the Phytohormones Jasmonic Acid and Methyl Jasmonate

No Evidence for the Induction of Brown Algal Chemical Defense by the Phytohormones Jasmonic Acid and Methyl Jasmonate

The potential role of wound-activated volatile release in the chemical defence of the brown alga Dictyota dichotoma: Blend recognition by marine herbivores

Variability of a diterpene with potential anti-HIV activity isolated from the Brazilian brown alga Dictyota menstrualis

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