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Useful Strategies for Algal Volatile Analysis
Abstract and Figures
The production of volatile organic compounds (VOC) by plants is well known. However, few scientific groups have studied VOC produced by green, brown and red algae. Headspace collection of volatiles and solid phase microextraction, as well as the traditional extraction by hydrodistillation combined with analytical chromatographic techniques (i.e., GC-MS), have significantly improved the investigation of VOC from plants and algae. The major volatile compounds found in seaweeds are hydrocarbons, terpenes, phenols, alcohols, aldehydes, ketones, esters, fatty acids and halogen or sulfur-containing compounds. This article presents an overview of VOC isolated from and identified in marine macro-algae. Focus is given to non-halogenated and non-sulfur volatile compounds, as well as strategies to analyze and identify algal VOC by GC-MS.
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... Irradiance is one of the main drivers of ice sheet surface melt, and so any volatiles originating from the ice, as a result of melting out of recent and/or past deposition, will likely peak on sampling days with high irradiance. However, microbial contributions to the total VOC emissions from bare ice surfaces are also expected (Gressler et al., 2009;Sun S. M. et al., 2012) Cyanobacterial (Dembitsky et al., 1999) Pentadecane 107 ± 37 82 ± 46 187 ± 29 Algal (Gressler et al., 2009;Yamamoto et al., 2014) Cyanobacterial (Milovanović et al., 2015) Cyclohexane n.d. 256 ± 53 117 ± 33 Algal (Ali, 2004) Fungal (Ezeonu et al., 1994) to peak at high irradiances for several reasons. ...
... Irradiance is one of the main drivers of ice sheet surface melt, and so any volatiles originating from the ice, as a result of melting out of recent and/or past deposition, will likely peak on sampling days with high irradiance. However, microbial contributions to the total VOC emissions from bare ice surfaces are also expected (Gressler et al., 2009;Sun S. M. et al., 2012) Cyanobacterial (Dembitsky et al., 1999) Pentadecane 107 ± 37 82 ± 46 187 ± 29 Algal (Gressler et al., 2009;Yamamoto et al., 2014) Cyanobacterial (Milovanović et al., 2015) Cyclohexane n.d. 256 ± 53 117 ± 33 Algal (Ali, 2004) Fungal (Ezeonu et al., 1994) to peak at high irradiances for several reasons. ...
... Recently, an enzyme belonging to an algae-specific subgroup of the glucose-methanol-choline oxidoreductase family, fatty acid (Matysik et al., 2008) 1-Nonene 94 ± 33 45 ± 25 72 ± 8 Fungal (Matysik et al., 2008) 1-Heptene 66 ± 5 60 ± 18 72 ± 12 Fungal (Matysik et al., 2008) 1-Hexene 38 ± 6 32 ± 8 47 ± 6 1-Tridecene 24 ± 0 14 ± 6 33 ± 4 Algal (Kumar et al., 2011) 1-Dodecene 28 ± 8 n.d. 28 ± 5 Algal (Gressler et al., 2009;Zuo et al., 2012a) 2-Octene 16 ± 2 14 ± 4 17 ± 3 Algal (Zuo et al., 2015) 1-Tetradecene 22 ± 12 n.d. 16 ± 3 Algal (Gressler et al., 2009;Renukadevi et al., 2011) Unknown alkene 1 12 ± 5 6 ± 3 10 ± 1 2,4-Dimethylhept-1-ene 5 ± 2 2 ± 1 3 ± 1 Algal (Gressler et al., 2009) 1,3-Octadiene 5 ± 2 3 ± 1 3 ± 1 Algal (Sun X. et al., 2012) 1,1,3-Trimethylcyclohexane n.d. 3 ± 1 n.d. ...
Volatile organic compounds (VOCs) are emitted by organisms for a range of physiological and ecological reasons. They play an important role in biosphere–atmosphere interactions and contribute to the formation of atmospheric secondary aerosols. The Greenland ice sheet is home to a variety of microbial communities, including highly abundant glacier ice algae, yet nothing is known about the VOCs emitted by glacial communities. For the first time, we present VOC emissions from supraglacial habitats colonized by active microbial communities on the southern Greenland ice sheet during July 2020. Emissions of C5–C30 compounds from bare ice, cryoconite holes, and red snow were collected using a push–pull chamber active sampling system. A total of 92 compounds were detected, yielding mean total VOC emission rates of 3.97 ± 0.70 μg m –2 h –1 from bare ice surfaces ( n = 31), 1.63 ± 0.13 μg m –2 h –1 from cryoconite holes ( n = 4), and 0.92 ± 0.08 μg m –2 h –1 from red snow ( n = 2). No correlations were found between VOC emissions and ice surface algal counts, but a weak positive correlation ( r = 0.43, p = 0.015, n = 31) between VOC emission rates from bare ice surfaces and incoming shortwave radiation was found. We propose that this may be due to the stress that high solar irradiance causes in bare ice microbial communities. Acetophenone, benzaldehyde, and phenylmaleic anhydride, all of which have reported antifungal activity, accounted for 51.1 ± 11.7% of emissions from bare ice surfaces, indicating a potential defense strategy against fungal infections. Greenland ice sheet microbial habitats are, hence, potential sources of VOCs that may play a role in supraglacial microbial interactions, as well as local atmospheric chemistry, and merit future research efforts.
... Essential oils (EOs), as a special chemical group of algal metabolites, play an important role in communication in marine ecosystems, both interspecies and intraspecies, as well as in interactions with the surrounding environment. These compounds are involved in various algal ecological functions: they are defenses against predators and herbivores; they act as pheromones (allelochemicals; take part in the adaptation to abiotic stresses; and are important for the inhibition of bacterial and/or fungal fouling [1,[10][11][12]. The essential oil metabolites present in marine algae species contain a mixture of different chemical classes such as hydrocarbons, fatty acids, esters, alcohols, carboxylic acids, aldehydes, ketones, terpenes, polyphenols, furans, pyrazines, pyridines, halogenated amines, and sulphur compounds [1,2]. ...
... The essential oil metabolites present in marine algae species contain a mixture of different chemical classes such as hydrocarbons, fatty acids, esters, alcohols, carboxylic acids, aldehydes, ketones, terpenes, polyphenols, furans, pyrazines, pyridines, halogenated amines, and sulphur compounds [1,2]. The production of algal EOs is closely related to the physiology of the species [11,12]. Studies on EOs of green and red algae mainly report the presence of monoterpenoids, halogenated compounds, and sulphur compounds that have a low impact on their aroma perception. ...
... However, despite all its disadvantages (duration, high temperatures, low efficiency, potential degradation of compounds, etc.), hydrodistillation is still the most used method. On the other hand, identification of the EO components is usually performed using capillary gas chromatography coupled with mass spectrometry (GC-MS), as this method of characterization covers a wide spectrum of compounds, from non-polar to polar ones [11,13]. ...
Marine macroalgae are well known to release a wide spectrum of volatile organic components, the release of which is affected by environmental factors. This paper aimed to identify the essential oil (EO) compounds of the brown algae Cystoseira compressa collected in the Adriatic Sea monthly, from May until August. EOs were isolated by hydrodistillation using a Clavenger-type apparatus and analyzed by gas chromatography coupled with mass spectrometry (GC–MS). One hundred four compounds were identified in the volatile fraction of C. compressa, accounting for 84.37–89.43% of the total oil. Samples from May, June, and July were characterized by a high share of fatty acids (56, 69, and 34% respectively) with palmitic acid being the dominant one, while in the August sample, a high content of alcohols (mainly phytol and oleyl alcohol) was found. Changes in the other minor components, which could be important for the overall aroma and biological activities of the algal samples, have also been noted during the vegetation periods. The results of this paper contribute to studies of algal EOs and present the first report on C. compressa EOs.
... The insecticidal potential of seaweeds is described (Table 1). Chemical composition analysis of seaweed extracts revealed that halogenated compounds such as triterpenoids and lipophilic compounds such as fatty acids are involved in insecticidal activity (Gressler et al., 2009). Oil-based compounds penetrate insects' bodies through cuticles and respiratory tracts and cause cellular and haemolymph acidosis, which leads to death (Sugiura et al., 2008). ...
... Oil-based compounds penetrate insects' bodies through cuticles and respiratory tracts and cause cellular and haemolymph acidosis, which leads to death (Sugiura et al., 2008). Fucus spiralis brown algae essential oil has an insecticidal effect against the Mediterranean fruit fly, Ceratitis capitata (Diptera: Tephritidae) (Gressler et al., 2009). Insecticidal efficiency was tested on the pupae and adults using different concentrations of F. spiralis essential oils. ...
Presently, the world is using eco-friendly products to limit pollution in soil, air, water, and marine environments and to mitigate rapid climate change according to the sustainable development goals of the United Nations Development Programme. As a result, most countries attempt to produce environmentally friendly herbicides, fertilizers, and pesticides from plants, algae (e.g., Cladophora glomerata, Laurencia pinnata, Plocamium cartilagineum, Polcamium spp.) or animal manure. Plants, such as Anethum sowa, Thymus vulgaris, Foeniculum vulgare, Syzygium aromaticum, Pinus sylvestris, Citrus spp., Piper spp. and Mentha spicata, are ecofriendly sources of essential oils, containing safe components, which can resist harmful pests. This review evaluates the common plants and algae used for extracting biopesticides, geographical distribution, target pests, mode of action, and commercial viability.
... The insecticidal potential of seaweeds is described (Table 1). Chemical composition analysis of seaweed extracts revealed that halogenated compounds such as triterpenoids and lipophilic compounds such as fatty acids are involved in insecticidal activity (Gressler et al., 2009). Oil-based compounds penetrate insects' bodies through cuticles and respiratory tracts and cause cellular and haemolymph acidosis, which leads to death (Sugiura et al., 2008). ...
... Oil-based compounds penetrate insects' bodies through cuticles and respiratory tracts and cause cellular and haemolymph acidosis, which leads to death (Sugiura et al., 2008). Fucus spiralis brown algae essential oil has an insecticidal effect against the Mediterranean fruit fly, Ceratitis capitata (Diptera: Tephritidae) (Gressler et al., 2009). Insecticidal efficiency was tested on the pupae and adults using different concentrations of F. spiralis essential oils. ...
Presently, the world is using eco-friendly products to limit pollution in soil, air, water, and marine environments and to mitigate rapid climate change according to the sustainable development goals of the United Nations Development Programme. As a result, most countries attempt to produce environmentally friendly herbicides, fertilizers, and pesticides from plants, algae (e.g., Cladophora glomerata, Laurencia pinnata, Plocamium cartilagineum, Polcamium spp.) or animal manure. Plants, such as Anethum sowa, Thymus vulgaris, Foeniculum vul-
gare, Syzygium aromaticum, Pinus sylvestris, Citrus spp., Piper spp. and Mentha spicata, are ecofriendly sources of essential oils, containing safe components, which can resist harmful pests. This review evaluates the common plants and algae used for extracting
biopesticides, geographical distribution, target pests, mode of action, and commercial viability
... Halogenated compounds are quite common in marine algae due to the high concentration of chlorine and bromine ions in seawater [65,66]. In dried G. vermiculophylla, a total of 18 halogenated compounds, mainly haloalkanes, were determined representing less than ca. 1 % of the total GC areas. ...
... Macroalgae are source of fibers, minerals, steroids, antioxidants, vitamins, pigments, lectins, polysaccharides, halogenated compounds, polyketides, polyunsaturated fatty acids (specially omega 3 and 6 families), mycosporine-like amino acids, proteins, and other lipids which make them largely consumed in many countries. (Cardozo et al. 2007;Gressler et al. 2009Gressler et al. , 2011Martins et al, 2016). Furthermore, isolated compounds, extracts and fractionated extracts have been reported to have important biological activities, including anti-inflammatory, neglected diseases such as leishmanicidal, trypanocidal (Torres et al. 2014;Falkenberg et al. 2019;Rangel et al. 2019;Clementino et al. 2020;, schistosomicidal (Stein et al. 2021), antioxidant and UV absorber (Rangel et al. 2020;Tavares et al. 2020a;2020b), anticancer (Vieira et al. 2016;Santos-Pirath et al. 2020, Gambato et al. 2014, biofilms for drug release (Paniz et al. 2020) and microbicidal properties as antifungal (Stein et al. 2011), antivirus (Cirne-Santos et al. 2020, antifouling (Salgado et al. 2008, Carvalho et al. 2017. ...
The present review aims the discussion of the impact of the bioprospection initiative developed by the projects associated to BIOprospecTA, a subprogram of the program BIOTA, supported by FAPESP. This review brings a summary of the main results produced by the projects investigating natural products (NPs) from non-plants organisms, as examples of the success of this initiative, focusing on the progresses achieved by the projects related to NPs from macroalgae, marine invertebrates, arthropods and associated microorganisms. Macroalgae are one of the most studied groups in Brazil with the isolation of many bioactive compounds including lipids, carotenoids, phycocolloids, lectins, mycosporine-like amino acids and halogenated compounds. Marine invertebrates and associated microorganisms have been more systematically studied in the last thirty years, revealing unique compounds, with potent biological activities. The venoms of Hymenopteran insects were also extensively studied, resulting in the identification of hundreds of peptides, which were used to create a chemical library that contributed for the identification of leader models for the development of antifungal, antiparasitic, and anticancer compounds. The built knowledge of Hymenopteran venoms permitted the development of an equine hyperimmune serum anti honeybee venom. Amongst the microorganisms associated with insects the bioprospecting strategy was to understand the molecular basis of intra- and interspecies interactions (Chemical Ecology), translating this knowledge to possible biotechnological applications. The results discussed here reinforce the importance of BIOprospecTA program on the development of research with highly innovative potential in Brazil.
Kappaphycus alvarezii is one of the most essential edible seaweeds in the global trade of marine products. The product quality will directly influence the flavor, odor, and impact on the human health of this edible seaweed. These functions are associated with volatile organic compound (VOCs) content and are controlled by seaweed cultivation sites. This study investigated VOCs using HS-SPME combined with GC–MS and multivariate analysis to determine the VOCs to be used as key markers for the quality of seaweeds from different cultivation sites. The HS-SPME factors, such as the amount of sample, extraction temperature, and extraction time, were optimized based on Box–Behnken design (BBD) and response surface methodology (RSM) for multi-response optimization (MRO). The precision of the approach varied from 1.17% (alkanes) to 6.30% (carboxylic acids) for repeatability and 3.93% (furans) to 16.64% (sesquiterpenoids) for intermediate precision. This method was applied to samples collected from nine different geographical regions in Indonesia. Principal Component Analysis (PCA) was used to determine data distribution from 48 compounds in K. alvarezii from those different cultivation sites. Based on PCA, four key marker VOCs, including heptadecane, 3-methylbutanoic acid, 2-pentyl furan, and 2-heptanone, were successfully established.
The potential of algae, plants, fungi, and bacteria to produce a wide spectrum
of volatile organic compounds (VOCs) including terpenes, alkanes, alkenes,
alcohols, ketones, aldehydes, benzenoids, esters, and sulfo compounds is
remarkable. Thus, the antifungal activity of volatiles emitted from D. tharense, C.
vulgaris, and N. arenaria was evaluated against M. phaseolina and F.
oxysporum under living conditions through a system that allows the exchange of
VOCs between algae and phytopathogenic fungi without physical contact
between them. Volatiles released from C. vulgaris and D. tharense cultures cause
a significant growth reduction for F. oxysporum and M. phaseolina, and the
highest activity was recorded by C. vulgaris. Volatiles of C. vulgaris which
exhibited the highest antifungal activity were collected under natural living
conditions by the headspace method and analyzed by GC/MS. GC/MS analysis
of C. vulgaris volatiles proved that a complex mixture of bioactive and inactive
natural compounds was produced by this alga. The identified compounds
produced by C. vulgaris cells were belonging to different chemical classes, such
as alkanes, cyclic alkanes, phenols, halogenated compounds, amides, acids,
alcohols, ketones, lactones, fatty esters, fatty acid methyl esters, phthalic acid
derivatives, and alcohols. The antifungal activity of C. vulgaris is attributed to the
synergetic effect of all potent antifungal compounds produced by the alga cells.
During the biological evolution, marine macroalgae have developed biochemicals tools in order to utilize components of seawater such as sulfates and halogens, to produce a variety of chemicals (secondary metabolites). This review shows and discuss the occurrence of sulfated and/or halogenated phenolic compounds in seaweeds.
The compounds (III) and (VI) - (VIII) are isolated from marine brown algae, together with seven known derivatives.
A technique for water sample analysis is presented which uses chemically modified fused silica optical fibers as micro solid phase extractors. The small size of the fibers (100 μm o.d.) allows for direct introduction into the on column injector port of a high resolution gas chromatograph (GC), where the analytes are thermally desorbed. This eliminates the need for solvents and syringes which are used in liquid-liquid or solid phase extraction techniques. Thus, this method lowers cost and analysis time per sample, as well as eliminates possible sources of error. Results show that the efficiency and selectivity of this technique are dependent upon the thickness and polarity of the stationary phase. Initial results indicate that the limit of detection for 2-naphthol and FID detection is approximately 5 ng/g with a linear response range of 5 orders of magnitude.
Laboratory-scale equipment was developed making the Pulsed Electric Field (PEF)-treatment possible during solid-liquid extraction. Preliminary experiments were performed for testing the effect of pulsed electric energy input on mass transfer kinetics. As example the kinetics of extraction of water-soluble polysaccharides fraction from linseeds (Linum usitatissimum L.) has been studied. Samples were submitted to PEF treatment at varying field strengths (0.5 to 5 kV cm -1) applying a pulse numbers up to 900 with a pulse duration of 900 µs. Additional effect of moisture content of dried or wetted samples were also studied. The results indicated that recognizable increase in mass transfer rate started to occur at 0.5 kV cm -1 moderate field strength at short times of PEF treatment in the range of 2 min.
Terpene profiles in cheese can be considered a ‘terroir’ fingerprint as the information contained in it should enable the pastures on which the animals were fed to be recognised. Yet a certain elasticity of the signature must be taken into account when determining authentication strategies, since products acknowledged as containing a common signature may have undergone certain procedures, such as cheese making and milk pasteurisation, that could have potentially altered their terpene profiles. In this study, Cantal and Saint‐Nectaire‐type cheeses were made from both raw and pasteurised milk from the same herd of dairy cows that had been grazed on natural grassland. Cheeses from raw and pasteurised milk were made from the same milking on the same days. Cantal and Saint‐Nectaire‐type cheeses were made on 4 different days, alternatively over four weeks. The terpenes in the cheese fat were analysed by dynamic headspace/gas chromatography/mass spectrometry. A great diversity of monoterpenes, sesquiterpenes and oxygen‐containing derivatives were identified. The major terpenes identified in most cheeses were ‐caryophyllene, α‐ and ‐pinene and limonene. Milk pasteurisation did not induce changes in the terpene profile of the cheese. Significant differences (p p p‐cymene and α‐terpinene in Saint‐Nectaire cheese. Copyright © 2005 Society of Chemical Industry
Two new odoriferous compounds, dictyoprolene and neodictyoprolene have been isolated from the brown alga Dictyopteris prolifera and their structures determined by chemical and spectral means. Synthesis of optically active and racemic has been made. Dictyoprolene and neodictyoprolene have been shown to be the acetates of the 1-undecen-3-ols, the postulated biosynthetic precursors of various C11 hydrocarbons and the related compounds obtained from brown algae, Dictyopteris, Ectocarpus, and Cutleria.
The major hydrocarbon component of the brown seaweed Dictyopteris zonarioides, zonarene, has been isolated and identified as the first C15H24 conjugated diene sesquiterpene of the cadanane type.
Dictyopterenes A, C′ and D′ found in sexually mature thalli of Scytosiphon lomentaria were not detected in the secretion from the female gametes of S. lomentaria and Colpomenia bullosa. Dictyopterene B [(−)-hormosirene] was secreted at a rate of 2.8 × 10−20 mol cell−1 sec−1 as a sex pheromone from the settled female gametes of both species. Dictyopterenes B and D′ were detected from female gametes of Analipus japonicus. The absolute configurations of dictyopterene B in secretions from the female gametes were found to be (1R,2R) with 66–94% e.e., respectively.