“…Ring opened MCs are designated with the prefix [seco-a/b], where a and b are the residue numbers between which the amide bond has been hydrolysed. For example, [seco-4/5]MC-LR indicates MC-LR hydrolysed between the Arg 4 -and Adda 5 -residues. A MC name-generator is included in version 16 of the MC mass calculator tab of a publicly available toxin mass list [53].…”
Section: Nomenclature and General Chemical Structure Of Microcystinsmentioning
confidence: 99%
“…Isomerization of the C-6 double bond in the Adda 5 group is rarely reported and is thought to be due to ultraviolet (UV) irradiation rather than arising through biosynthesis [190][191][192]. In early studies, Harada et al [115] and Namikoshi et al [76] isolated geometrical isomers at C-6 of [(6Z)-Adda 5 ]MC-LR and -RR, as minor components with along with the corresponding normal (6E)-Adda 5 MCs (MC-LR and -RR) from Microcystis spp. The DMAdda derivative at the Adda unit could be also an artefact produced during extraction of cyanobacterial samples dominated by ADMAdda derivatives.…”
Section: Chemical and Biochemical Transformations Of Microcystinsmentioning
confidence: 99%
“…There are an increasing number of warnings about toxic cyanobacterial blooms observed worldwide and global warming is thought to stimulate their development in eutrophic waters [1][2][3][4][5]. These blooms are often accompanied by production of a variety of cyanotoxins generally classified according to the target organs: hepatotoxins (liver), neurotoxins (nervous system), and dermatotoxins (skin).…”
Hepatotoxic microcystins (MCs) are the most widespread class of cyanotoxins and the one that has most often been implicated in cyanobacterial toxicosis. One of the main challenges in studying and monitoring MCs is the great structural diversity within the class. The full chemical structure of the first MC was elucidated in the early 1980s and since then, the number of reported structural analogues has grown steadily and continues to do so, thanks largely to advances in analytical methodology. The structures of some of these analogues have been definitively elucidated after chemical isolation using a combination of techniques including nuclear magnetic resonance, amino acid analysis, and tandem mass spectrometry (MS/MS). Others have only been tentatively identified using liquid chromatography-MS/MS without chemical isolation. An understanding of the structural diversity of MCs, the genetic and environmental controls for this diversity and the impact of structure on toxicity are all essential to the ongoing study of MCs across several scientific disciplines. However, because of the diversity of MCs and the range of approaches that have been taken for characterizing them, comprehensive information on the state of knowledge in each of these areas can be challenging to gather. We have conducted an in-depth review of the literature surrounding the identification and toxicity of known MCs and present here a concise review of these topics. At present, at least 279 MCs have been reported and are tabulated here. Among these, about 20% (55 of 279) appear to be the result of chemical or biochemical transformations of MCs that can occur in the environment or during sample handling and extraction of cyanobacteria, including oxidation products, methyl esters, or post-biosynthetic metabolites. The toxicity of many MCs has also been studied using a range of different approaches and a great deal of variability can be observed between reported toxicities, even for the same congener. This review will help clarify the current state of knowledge on the structural diversity of MCs as a class and the impacts of structure on toxicity, as well as to identify gaps in knowledge that should be addressed in future research.
“…Ring opened MCs are designated with the prefix [seco-a/b], where a and b are the residue numbers between which the amide bond has been hydrolysed. For example, [seco-4/5]MC-LR indicates MC-LR hydrolysed between the Arg 4 -and Adda 5 -residues. A MC name-generator is included in version 16 of the MC mass calculator tab of a publicly available toxin mass list [53].…”
Section: Nomenclature and General Chemical Structure Of Microcystinsmentioning
confidence: 99%
“…Isomerization of the C-6 double bond in the Adda 5 group is rarely reported and is thought to be due to ultraviolet (UV) irradiation rather than arising through biosynthesis [190][191][192]. In early studies, Harada et al [115] and Namikoshi et al [76] isolated geometrical isomers at C-6 of [(6Z)-Adda 5 ]MC-LR and -RR, as minor components with along with the corresponding normal (6E)-Adda 5 MCs (MC-LR and -RR) from Microcystis spp. The DMAdda derivative at the Adda unit could be also an artefact produced during extraction of cyanobacterial samples dominated by ADMAdda derivatives.…”
Section: Chemical and Biochemical Transformations Of Microcystinsmentioning
confidence: 99%
“…There are an increasing number of warnings about toxic cyanobacterial blooms observed worldwide and global warming is thought to stimulate their development in eutrophic waters [1][2][3][4][5]. These blooms are often accompanied by production of a variety of cyanotoxins generally classified according to the target organs: hepatotoxins (liver), neurotoxins (nervous system), and dermatotoxins (skin).…”
Hepatotoxic microcystins (MCs) are the most widespread class of cyanotoxins and the one that has most often been implicated in cyanobacterial toxicosis. One of the main challenges in studying and monitoring MCs is the great structural diversity within the class. The full chemical structure of the first MC was elucidated in the early 1980s and since then, the number of reported structural analogues has grown steadily and continues to do so, thanks largely to advances in analytical methodology. The structures of some of these analogues have been definitively elucidated after chemical isolation using a combination of techniques including nuclear magnetic resonance, amino acid analysis, and tandem mass spectrometry (MS/MS). Others have only been tentatively identified using liquid chromatography-MS/MS without chemical isolation. An understanding of the structural diversity of MCs, the genetic and environmental controls for this diversity and the impact of structure on toxicity are all essential to the ongoing study of MCs across several scientific disciplines. However, because of the diversity of MCs and the range of approaches that have been taken for characterizing them, comprehensive information on the state of knowledge in each of these areas can be challenging to gather. We have conducted an in-depth review of the literature surrounding the identification and toxicity of known MCs and present here a concise review of these topics. At present, at least 279 MCs have been reported and are tabulated here. Among these, about 20% (55 of 279) appear to be the result of chemical or biochemical transformations of MCs that can occur in the environment or during sample handling and extraction of cyanobacteria, including oxidation products, methyl esters, or post-biosynthetic metabolites. The toxicity of many MCs has also been studied using a range of different approaches and a great deal of variability can be observed between reported toxicities, even for the same congener. This review will help clarify the current state of knowledge on the structural diversity of MCs as a class and the impacts of structure on toxicity, as well as to identify gaps in knowledge that should be addressed in future research.
“…A recent review has summarized the extent of the literature investigating the fate in soils, and agricultural crops [103]. It seems quite clear that toxins can accumulate in plants, including food crops and under some conditions can also inhibit plant growth [102,103,[106][107][108]. Though there are many gaps, and only a handful of studies have investigated this route for exposure.…”
In the race to enhance agricultural productivity, irrigation will become more dependent on poorly characterized and virtually unmonitored sources of water. Increased use of irrigation water has led to impaired water and soil quality in many areas. Historically, soil salinization and reduced crop productivity have been the primary focus of irrigation water quality. Recently, there is increasing evidence for the occurrence of geogenic contaminants in water. The appearance of trace elements and an increase in the use of wastewater has highlighted the vulnerability and complexities of the composition of irrigation water and its role in ensuring proper crop growth, and long-term food quality. Analytical capabilities of measuring vanishingly small concentrations of biologically-active organic contaminants, including steroid hormones, plasticizers, pharmaceuticals, and personal care products, in a variety of irrigation water sources provide the means to evaluate uptake and occurrence in crops but do not resolve questions related to food safety or human health effects. Natural and synthetic nanoparticles are now known to occur in many water sources, potentially altering plant growth and food standard. The rapidly changing quality of irrigation water urgently needs closer attention to understand and predict long-term effects on soils and food crops in an increasingly fresh-water stressed world.
“…Importantly, these changes can alter the structure and functional processes of boreal ecosystems, which range from forest and freshwater productivity, water quantity and quality, range shifts of species, and stability of ice and permafrost (defined as soil or rock remaining at or below 0°C for at least 2 years) to the regimes of natural disturbances, including wildfires, insect and disease outbreaks, and windthrow (e.g., Schindler 1998;Price et al 2013;Scheffers et al 2016). In conjunc-tion with anthropogenic changes in the transport and deposition of hazardous air pollutants, atmospheric change can affect the status and productivity of boreal ecosystems, therefore mediating a range of goods and services, human health and socio-economic conditions in the boreal (see Anielski and Wilson 2009;Chen et al 2016;Miller and Russell 2017).…”
Section: Why Is Atmospheric Change An Important Driver Of the Boreal?mentioning
Global anthropogenic emissions of greenhouse gases and hazardous air pollutants have produced broad yet regionally disparate changes in climatic conditions and pollutant deposition in the Canadian boreal zone (the boreal). Adapting boreal resource management to atmospheric change requires a holistic understanding and awareness of the ongoing and future responses of terrestrial and freshwater ecosystems in this vast, heterogeneous landscape. To integrate existing knowledge of and generate new insights from the broad-scale impacts of atmospheric change, we first describe historical and present trends (∼1980–2015) in temperature, precipitation, deposition of hazardous air pollutants, and atmospheric-mediated natural disturbance regimes in this region. We then examine their associations with ecosystem condition and productivity, biological diversity, soil and water, and the carbon budget. These associations vary considerably among ecozones and likely undergo further changes under the emerging risks of atmospheric change. We highlight the urgent need to establish long-term, boreal-wide monitoring for many key components of freshwater ecosystems to better understand and project the influences of atmospheric change on boreal water resources. We also formulate three divergent future scenarios of boreal ecosystems in 2050. Our scenario analysis reveals multiple undesirable changes in boreal ecosystem structure and functioning with more variable atmospheric conditions and frequent land disturbances, while continuing business-as-usual management of natural resources. It is possible, though challenging, to reduce unwanted consequences to ecosystems through management regimes focussed on socio-ecological sustainability and developing resilient infrastructure and adaptive resource-management strategies. We emphasize the need for proactive actions and improved foresight for all sectors of society to collaborate, innovate, and invest in anticipation of impending global atmospheric change, without which the boreal zone will face a dim future.
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