The Use of Invasive Algae Species as a Source of Secondary Metabolites and Biological Activities: Spain as Case-Study.

In the recent decades, algae have proven to be a source of different bioactive compounds with biological activities, which has increased the potential application of these organisms in food, cosmetic, pharmaceutical, animal feed, and other industrial sectors. On the other hand, there is a growing interest in developing effective strategies for control and/or eradication of invasive algae since they have a negative impact on marine ecosystems and in the economy of the affected zones. However, the application of control measures is usually time and resource-consuming and not profitable. Considering this context, the valorization of invasive algae species as a source of bioactive compounds for industrial applications could be a suitable strategy to reduce their population, obtaining both environmental and economic benefits. To carry out this practice, it is necessary to evaluate the chemical and the nutritional composition of the algae as well as the most efficient methods of extracting the compounds of interest. In the case of northwest Spain, five algae species are considered invasive: Asparagopsis armata, Codium fragile, Gracilaria vermiculophylla, Sargassum muticum, and Grateulopia turuturu. This review presents a brief description of their main bioactive compounds, biological activities, and extraction systems employed for their recovery. In addition, evidence of their beneficial properties and the possibility of use them as supplement in diets of aquaculture animals was collected to illustrate one of their possible applications.

A study of the chemical diversity of macroalgae from South Eastern Australia.

Macroalgae are a rich source of biologically active chemical diversity for pharmaceutical and agrichemical discovery. However, the ability to understand the complexities of their chemical diversity will dictate whether these natural products have a place in modern discovery paradigms. In this study, we examined the relationship between secondary metabolite production and biological activity for a cohort of 127 macroalgae samples collected from various locations across South Eastern Australia. Approximately 20% of the macroalgae samples showed high levels of chemical diversity and productivity, which also correlated strongly with bioactivity. These "talented" species represent sustainable sources of metabolites that may be readily harvested for large-scale production. At a taxonomic level, significant differences in metabolite production and diversity were observed between Chlorophyta, Rhodophyta and Phaeophyta. For each talented species, the cometabolite pattern was unique to that species, with closely related species within the same genus displaying very different profiles. Despite over 50years of investigation, we estimate that more than two-thirds of the chemical diversity of macroalgae remains unknown to science. By understanding the physicochemical properties and distribution patterns of metabolites, it is possible to make reasoned judgements about sustainable sourcing of macroalgae for biodiscovery.

Edible seaweed as future functional food: Identification of α-glucosidase inhibitors by combined use of high-resolution α-glucosidase inhibition profiling and HPLC-HRMS-SPE-NMR.

Crude chloroform, ethanol and acetone extracts of nineteen seaweed species were screened for their antioxidant and α-glucosidase inhibitory activity. Samples showing more than 60% α-glucosidase inhibitory activity, at a concentration of 1 mg/ml, were furthermore investigated using high-resolution α-glucosidase inhibition profiling combined with high-performance liquid chromatography-high-resolution mass spectrometry-solid-phase extraction-nuclear magnetic resonance spectroscopy (HR-bioassay/HPLC-HRMS-SPE-NMR). The results showed Ascophyllum nodosum and Fucus vesicolosus to be rich in antioxidants, equaling a Trolox equivalent antioxidant capacity of 135 and 108 mM Troloxmg(-1) extract, respectively. HR-bioassay/HPLC-HRMS-SPE-NMR showed the α-glucosidase inhibitory activity of A. nodosum, F. vesoculosus, Laminaria digitata, Laminaria japonica and Undaria pinnatifida to be caused by phlorotannins as well as fatty acids - with oleic acid, linoleic acid and eicosapentaenoic acid being the most potent with IC50 values of 0.069, 0.075 and 0.10 mM, respectively, and showing a mixed-type inhibition mode.

Inhibitory effects of seaweed extracts on the growth of the vaginal bacterium Gardnerella vaginalis.

Of 44 species of seaweed screened for potential anti-Gardnerella vaginalis activity, 27 (61.4%) showed antimicrobial activity by the agar disk-diffusion method. Among them, the strongest activities against the pathogen were exhibited by Chlorophyta, with Ulva pertusa producing an 11.3-mm zone of inhibition at 5 mg disk⁻¹. The MIC values of U. pertusa extracts against both G. vaginalis KCTC 5096 and KCTC 5097, the main cause of vaginosis, were 312 µg ml⁻¹, while the MIC values against both Candida albicans KCTC 7270 and KCTC 7965, the main cause of candidiasis, were 2.5 mg ml⁻¹. Against Lactobacillus gasseri KCTC 3173 and Lactobacillus jensenii KCTC 5194, members of the normal vaginal microflora, no inhibitory effect was seen even at 10 mg ml⁻¹. To identify the primary active compounds, a U. pertusa powder was successively fractionated according to polarity, and the main active agents against G. vaginalis KCTC 5096 were determined to be nitrogenous compounds (156 µg ml⁻¹ of the MIC value). According to these results, it was suggested that extracts of the seaweed U. pertusa are valuable for the development of natural therapeutic agents for treating women with bacterial vaginosis.

Dominance patterns in macroalgal and phytoplankton biomass under different nutrient loads in subtropical coastal lagoons of the SE Gulf of California.

Nine macroalgal blooms were studied in five coastal lagoons of the SE Gulf of California. The nutrient loads from point and diffuse sources were estimated in the proximity of the macroalgal blooms. Chlorophyll a and macroalgal biomass were measured during the dry, rainy and cold seasons. Shrimp farms were the main point source of nitrogen and phosphorus loads for the lagoons. High biomasses were found during the dry season for phytoplankton at site 6 (791.7±34.6 mg m(-2)) and during the rainy season for macroalgae at site 4 (296.0±82.4 g m(-2)). Depending on the season, the phytoplankton biomass ranged between 40.0 and 791.7 mg m(-2) and the macroalgal biomass between 1 and 296.0 g m(-2). The bulk biomass (phytoplankton+macroalgal) displayed the same tendency as the nutrient loads entering the coastal lagoons. Phytoplankton and macroalgal biomass presented a significant correlation with the atomic N:P ratio.

Desenvolvimento vegetativo e produção de óleo essencial de patchouli (Pogostemon cablin (Blanco) Benth. ) após a aplicação de ácido giberélico e extrato de alga marinha / Development and essential oil production of Pogostemon cablin (Blanco) Benth. patchouli after applying gibberellic acid and seaweed extract

Pogostemon cablin (Blanco) Benth., comumente conhecido como patchouli, é uma espécie aromática utilizada pela indústria de perfumes devido a fragrância amadeirada e propriedade fixadora do óleo essencial. Fatores que afetam o teor dos constituintes do óleo essencial devem ser avaliados visando obter matéria prima de melhor qualidade. O experimento foi conduzido em casa de vegetação com delineamento inteiramente casualizado em esquema fatorial 2x3 e 4 repetições, sendo dois níveis de giberelina (0 e 200 mg L-1) e três níveis de extrato de alga marinha (0, 15 e 30 mg L-1). A aplicação dos reguladores vegetais foi realizada 30 dias após o plantio das mudas, e a avaliação do experimento deu-se 45 dias após a aplicação dos tratamentos. Não houve diferença significativa para a altura das plantas, a concentração de extrato de alga marinha de 15 mg L-1 promoveu aumento no número de folhas em relação à testemunha e a concentração de 30 mg L-1 promoveu decréscimo. Em relação à área foliar e ao número de folhas houve relação inversa para os níveis de extrato de alga marinha, onde o tratamento com maior concentração do regulador resultou em aumento da área foliar e redução do número de folhas. O teor de óleo essencial foi superior após a aplicação de 15 mg L-1 de extrato alga marinha isoladamente ou combinado com GA3. A produtividade do óleo essencial também aumentou com a aplicação 15 mg L-1 de extrato de alga marinha e quando utilizado somente GA3. A utilização de extrato de alga marinha aumentou a concentração de patchoulol no óleo essencial.

Pogostemon cablin (Blanco) Benth., commonly known as patchouli, is an aromatic species used by the perfume industry due to its woody fragrance and the fixative characteristic of its essential oil. Factors affecting the content of the constituents of essential oils should be evaluated in order to obtain raw materials with better quality. The experiment was carried out in a greenhouse in a completely randomized 2x3 factorial arrangement and four replications, with two levels of gibberellin (0 and 200 mg L-1) and three levels of seaweed extract (0, 15 and 30 mg L-1). Plant regulators were applied thirty days after planting the seedlings; the experiment was evaluated forty-five days after the treatments. There was no significant difference in plant height; the 15 mg L-1 concentration of seaweed extract promoted an increase in the number of leaves in relation to the control; and the 30 mg L-1 concentration promoted a decrease. In relation to leaf area and leaf number, there was an inverse relationship for the seaweed extract levels, in which the treatment with higher a concentration of the regulator resulted in an increased leaf area, reducing the number of leaves. The essential oil content was higher after applying 15 mg L-1 of seaweed extract alone or combined with GA3. The yield of essential oil also increased by applying 15 mg L-1 of seaweed extract and when only GA3 was used. The use of seaweed extract increased the patchoulol concentration in the essential oil.

Antiulcer, wound healing and hepatoprotective activities of the seaweeds Gracilaria crassa, Turbinaria ornata and Laurencia papillosa from the southeast coast of India

Seaweeds have bioactive compounds of interest in the pharmaceutical industry. In India, seaweeds are used exclusively for phycocolloids production and have not yet received consideration as a dietary supplement. So, it has become imperative to explore the biomedical potential of seaweeds and promote their utilization as a functional food. The seaweeds Turbinaria ornata, Gracillaria crassa and Laurencia papillosa, collected from the Tuticorin coast of the Southeast coast of India and selected based on preliminary screening, were extracted with acetone and evaluated for antiulcer, wound healing and hepatoprotective activities. L. papillosa showed the highest level of gastric protection activity (81%) at 200 mg/kg, comparable to the standard drug ranitidine (90%). G. crassa followed with 76%. G. crassa and L. papillosa, showed marked wound-healing activity. G. crassa at 200 mg/kg, showed a marked effect on the serum marker enzymes indicating prominent hepatoprotective activity. The noteworthy wound-healing and hepato-protective properties of G. crassa besides anti-ulcer activity next to L. papillosa were indicative of its potential for further consideration.

Algas marinhas possuem compostos bioativos de interesse para a indústria farmacêutica. Na Índia, as algas marinhas são usadas exclusivamente para a produção de ficocolóides e ainda não receberam a consideração como um suplemento dietético. Assim, tornou-se imperativo explorar o potencial biomédico de algas e promover a sua utilização como alimento funcional. As algas marinhas Turbinaria ornata, Gracillaria crassa e Laurencia papillosa, coletadas de Tuticorin, na costa sudeste da Índia, e selecionadas com base em triagem preliminar, foram extraídas com acetona e avaliadas quanto à atividade antiúlcera, de cicatrização de feridas e de hepatoproteção. L. papillosa mostrou o mais alto nível da atividade de proteção gástrica (81%) na dose de 200 mg/kg, comparável ao fármaco padrão, ranitidina (90%). G. crassa mostrou atividade de 76%. G. crassa e L. papillosa mostrou atividade martcante na cicatrização de feridas. G. Crassa, a 200 mg/kg, mostrou efeito alto sobre o marcador sérico das enzimas, indicando atividade hepatoprotetora proeminente. A notável cura de feridas e as propriedades hepatoprotetoras de G. Crassa, além da atividade antiúlcera, próxima da L. Papillosa, foram indicativos do seu potencial para uma análise mais aprofundada.

Inhibition of oral pathogens and collagenase activity by seaweed extracts.

Fifty-seven species of common seaweed from the Coast of Korea were screened for antimicrobial (i.e. inhibition of Prevotella intermedia and Porphyromonas gingivalis growth) activity. As a source of bioactive compounds, seaweeds can produce many secondary metabolites with a variety of activities. Using the agar diffusion method, only 17 species (29.8%) showed inhibitory activity. Of these, methanol extracts of Enteromorpha linza, Sargassum sagamianum, and Ulva pertusa showed strong inhibitory effects against both P. intermedia and P. gingivalis. The MIC values of E. linza, S. sagamianum, and U. pertusa extracts against P. intermedia were 625, 78 and 625 microg ml(-1) and those against P. gingivalis were 312, 156 and 625 microg ml(-1), respectively. When these three species' extracts were separated into five fractions according to their polarity, the main active agents were determined to be phenolic compounds. We then compared the antimicrobial activities of these phenolic compounds against various periodontal pathogens using a MIC test. Phenolic compound containing extracts at concentrations of 10 to 100 microg ml(-1) showed a moderate to significant inhibitory effect on collagenase 1,2 and 3 activity.

Inhibition of LDL-oxidation and antioxidant properties related to polyphenol content of hydrophilic fractions from seaweed Halimeda Incrassata (Ellis) Lamouroux

LDL oxidation and oxidative stress are closely related to atherosclerosis. Therefore, natural antioxidants have been studied as promising candidates. In the present study, the LDL oxidation inhibition activity of bioactive compounds from Halimeda incrassata seaweed. associated to antioxidant capacity, was evaluated in vitro. Experimental work was conducted with lyophilized aqueous extract and phenolic-rich fractions of the seaweed and their effect on LDL oxidation was evaluated using heparin-precipitated LDL (hep-LDL) with exposure to Cu2+ ions and AAPH as the free radical generator. H. incrassata had a protective effect for hep-LDL in both systems and the presence of phenolic compounds contributed to the activity where phenolic-rich fractions showed significant capacity for inhibition of oxidation mediated by Cu2+ ions. The observed effect could be related to the antioxidant potential of polar fractions evidenced by reducing activity and DPPH• radical scavenging. The results obtained in vitro further support the antioxidant and LDL oxidation inhibition properties of H. incrassata and further knowledge toward future phytotherapeutic application of the seaweed.

A oxidação da LDL e o estresse oxidativo estão intimamente relacionados com a aterosclerose. Por isso, os antioxidantes naturais têm sido estudados como candidatos promissores. No presente trabalho foi avaliada in vitro a capacidade de inibição da oxidação da LDL pelos compostos bioativos da alga Halimeda incrassata em associação à capacidade antioxidante. O trabalho experimental foi conduzido com extratos polares (extrato aquoso liofilizado e frações ricas em fenólicos) e seu efeito na oxidação da LDL foi avaliado usando LDL precipitada com heparina (hep-LDL), oxidada com íons de Cu2+ e AAPH, como geradores de radicais livres. A H. incrassata apresentou efeito protetor para hep-LDL em ambos sistemas e a presença de compostos fenólicos contribuiu para a atividade em que as frações ricas em fenólicos demonstram capacidade significativa em inibir a oxidação mediada pelos íons de Cu2+. O efeito observado deve estar relacionado com o potencial antioxidante das frações polares medido pela atividade redutora e varredura do radical DPPH. Os resultados obtidos demonstram as propriedades antioxidantes e de inibição da oxidação da LDL da H. incrassata e podem contribuir para as evidências de futuras aplicações fitoterapêuticas desta alga.

Fatty acids as chemotaxonomic markers of marine macrophytes from Rio de Janeiro state, Brazil.

The distribution of fatty acids in 13 species of macroalgae (Chlorophyta, Ochrophyta and Rhodophyta) and 1 seagrass (Spartina sp), collected on the Rio de Janeiro state coast was determined. The results were evaluated in search of correlations between the taxonomic and phylogenetic position of these macrophytes. Statistical analyses showed the effectiveness as taxonomic and phylogenetic markers of the distribution of the methyl fatty acid esters in these macrophytes.

Effects of nutrient enrichment on macroalgal coralligenous assemblages.

Effects of eutrophication on marine ecosystems have been widely studied, even if both the effects on deep subtidal rocky assemblages and response of different successional stages to nutrients impact are still not clear. In this context, the study aimed to evaluate the effects of nutrient enrichment on Mediterranean macroalgal assemblages associated with coralligenous habitat. A manipulative field experiment was carried out by supplying both mature and early successional stages of assemblages with nutrients. A total of 62 macroalgal species were identified. Multivariate and univariate analyses showed that the structure of both mature and early successional macroalgal assemblages of coralligenous significantly varied between areas treated with nutrients and not treated areas. Moreover, differences were stronger when macroalgal assemblages were in the early successional stage than in the mature one. Results highlighted the role played by nutrients in determining the structure of macroalgal coralligenous assemblages, furthermore suggesting possible synergetic effects with other kinds of disturbances.

Inhibitory effect of Jeju endemic seaweeds on the production of pro-inflammatory mediators in mouse macrophage cell line RAW 264.7.

Seaweed has been used in traditional cosmetics and as a herbal medicine in treatments for cough, boils, goiters, stomach ailments, and urinary diseases, and for reducing the incidence of tumors, ulcers, and headaches. Despite the fact that seaweeds are frequently used in the practice of human health, little is known about the role of seaweed in the context of inflammation. This study aimed to investigate the influence of Jeju endemic seaweed on a mouse macrophage cell line (RAW 264.7) under the stimulation of lipopolysaccharide (LPS). Ethyl acetate extracts obtained from 14 different kinds of Jeju seaweeds were screened for inhibitory effects on pro-inflammatory mediators. Our results revealed that extracts from five seaweeds, Laurencia okamurae, Grateloupia elliptica, Sargassum thunbergii, Gloiopeltis furcata, and Hizikia fusiformis, were potent inhibitors of the production of pro-inflammatory mediators such as nitric oxide (NO), prostaglandin E(2) (PGE(2)), interleukin-6 (IL-6), and tumor necrosis factor-alpha (TNF-alpha). Based on these results, the anti-inflammatory effects and low cell toxicity of these seaweed extracts suggest potential therapeutic applications in the regulation of the inflammatory response.

Composição química e potencial biológico das algas vermelhas marinhas Laurencia filiformis, Laurencia intricata, Plocamium brasiliense e Ochtodes secundiramea da costa brasileira / Chemical composition and biological potency of the marine red algae Laurencia filiformis, Laurencia intricata, Plocamium brasiliense and Ochtodes secundiramea of the Brazilian coast

O oceano apresenta uma vasta diversidade de espécies, entre elas as algas marinhas, as quais são usadas principalmente como fonte de alimentos, de produtos industriais e para uso medicinal. Considerando a biodiversidade encontrada, são poucos os estudos que verificam a composição química e atividade biológica de algas. Desta forma, o presente trabalho descreve especialmente compostos do metabolismo primário (lipídios, proteínas e aminoácidos), composição química volátil, e potencial antioxidante e antimicrobiano de quatro espécies de algas vermelhas da costa brasileira (Laurencia filiformis, Laurencia intricata, Plocamium brasiliense e Ochtodes secundiramea). As análises de lipídeos revelaram que estas algas são ricas em ácidos graxos poliinsaturados ω3 e ω6, mas que apresentam o ácido palmítico como majoritário. O teor de proteínas encontrado é considerável e aproximadamente 50% da composição de aminoácidos é de aminoácidos essenciais. Para extrair os compostos voláteis das algas selecionadas para o estudo, três métodos foram utilizados: arraste a vapor, extração por solvente e HS-SPME. A caracterização química dos compostos voláteis deu-se principalmente pela utilização de cromatografia gasosa acoplada à espectrometria de massas (CG-EM). Ainda foram isolados e identificados dois compostos majoritários do óleo essencial de L. filiformis, o (-)-7-epi-silfiperfolan-6β-ol e o (-)-silfiperfolan-7β-ol, e quatro compostos do extrato acetona/água de P. brasiliense, o 3,4-eritro-7-diclorometil-3-metil-3,4,8-tricloro-1,5(E),7(E)-octatrieno; o 3,4-eritro-7-diclorometil-3-metil-3,4,8-tricloro-1,5(E),7(Z)-octatrieno; o 3,4-eritro-1-bromo-7-diclorometil-3-metil-3,4,8-tricloro-1(E),5(E),7(E)-octatrieno e o 3,4-eritro-1-bromo-7-diclorometil-3-metil-3,4,8-tricloro-1(E),5(E),7(Z)-octatrieno, utilizando diferentes técnicas cromatográficas, como CCDP e CLAE, para isolamento, e técnicas espectroscópicas (RMN uni e bidimensionais) e espectrométricas (HRMS e EIMS) para análise...

The ocean provides large diversity of species, among them the seaweeds, which are mainly used as food, industrial products and as medicine. Considering the biodiversity, there are only few studies which analize the algae volatile compounds and their biological activity. So that, this work describes specially compounds from the primary metabolism (lipids, proteins and amino acids), chemical volatile composition, and antioxidant and antimicrobial potencies of four red algae of the Brazilian coast (Laurencia filiformis, Laurencia intricata, Plicamium brasiliense and Ochtodes secundiramea). The lipid analysis showed that these algae have ω3 and ω6 polyunsaturated fatty acids, but the palmitic acid is the most abundant. The protein content observed is considerable and approximately 50% of the amino acid composition is of essential amino acids. To extract the volatile organic compounds from the algae selected for this study, three methods were used: hydrodestilation, solvent extraction and HS-SPME. For chemical characterization of the volatile compounds, the technique used was gas chromatography coupled with mass spectrometry (GC-MS). In addition, the two most abundant compounds from the essential oil of L. filiformis, the (-)-7-epi-silphiperfolan-6β-ol and the (-)-silphiperfolan-7β-ol, and four compounds of the aceton/water extract of P. brasiliense the 3,4-erythro-7-dichloromethyl-3-methyl-3,4,8-trichloro-1,5(E),7(E)-octatriene; the 3,4-erythro-7-dichloromethyl-3-methyl-3,4,8-trichloro-1,5(E),7(Z)-octatriene; the 3,4-erythro-1-bromo-7-dichloromethyl-3-methyl-3,4,8-trichloro-1(E),5(E),7(E)-octatriene and the 3,4-erythro-1-bromo-7-dichloromethyl-3-methyl-3,4,8-trichloro-1(E),5(E),7(Z)-octatriene, were isolated and identified using different chromatographic techniques like preparative TLC and HPLC for isolation and spectroscopic (NMR uni and bidimensional) and spectrometric techniques (HRMS and EIMS) for analysis. The antioxidant activity of the essential oils, of...

Anti-inflammatory activities of methanol extracts from various seaweed species.

Thirty-seven species of common seaweeds from the coast of Korea were screened for anti-inflammatory activity Methanol extracts of the seaweeds were tested against mouse ear edema and erythema induced by phorbol myristate acetate. At 40 mg ml(-1) of extract, edema was strongly suppressed by the seaweeds Undaria pinnatifida and Ulva linza, with relative inhibition of 85 and 84%, respectively These two seaweeds also showed the greatest suppression of erythema, with inhibition of 78 and 70%, respectively IC50 values of U. pinnatifida were 10, 15, and 18 mg ml(-1) when inflammation symptoms of edema, erythema, and blood flow, respectively were measured. The IC50 of U. linza was 20, 26, and 31 mg ml(-1) when edema, erythema, and blood flow, respectively, were measured. A linear correlation among inhibition rates of edema, erythema, and blood flow was observed with high confidence.

Anti-tumorigenic components of a sea weed, Eeteromorpha clathrata.

Anti-tumorigenic action of compounds in some seaweed was evaluated by using selective cytotoxicity against a transformed mouse 3T3 cell (SV-T2) and its normal counter part. The extracts of seaweeds (Wakame, Konbu, Mirin, Aosa, and Sujiaonori) were added to the cells in 96 well microplate. The viability of the cell was measured at 24 hr after sample addition. Of the five weeds, the ethanol extracts from Sujiaonori exhibited the selective cytotoxicity. The ethanol extracts from Sujiaonori was applied to gel permeation chromatography on Sephadex G-50. The anti-cancer activity was detected in two fractions with high molecular weight near void volume and with small molecular weight. The high molecular weight fractions had absorbance at 280 nm, suggesting that they contained proteineous substances. The small molecular weight fractions were estimated to be around 500 Dalton.