Algal Metabolites Research Articles

Design of PPAR-γ agonist based on algal metabolites and the endogenous ligand 15-deoxy-Δ12, 14-prostaglandin J2

In a previous study, we synthesized endocyclic enone jasmonate derivatives that function as anti-inflammatory and PPAR-γ-activating entities by using key functional moieties of anti-inflammatory algal metabolites. Herein, we designed additional derivatives containing an exocyclic enone moiety that resembles the key structure of the natural PPAR-γ ligand, 15-deoxy-Δ12, 14-prostaglandin J2 (15 d-PGJ2). The exocyclic enone moiety of 15 d-PGJ2 is essential for covalent bonding with the Cys285 residue in the PPAR-γ ligand-binding domain (LBD). In silico analysis of the designed compounds indicated that they may form hydrogen bonds with key amino acid residues in the PPAR-γ LBD, and thus, secure a position in the bioactive cavity in a similar fashion as does rosiglitazone and 15 d-PGJ2. By a luciferase reporter assay on rat liver Ac2F cells, the synthesized compounds were evaluated for PPAR-γ transcriptional activity. The differential PPAR-γ transcriptional activities of the geometric and enantiomeric isomers of the selected analog were also evaluated; based on our results, the enantiopure compound (+)-(R,E)-6a1 was suggested as a potential PPAR-γ ligand.

Environmental Control on Microbial Turnover of Leaf Carbon in Streams - Ecological Function of Phototrophic-Heterotrophic Interactions.

In aquatic ecosystems, light availability can significantly influence microbial turnover of terrestrial organic matter through associated metabolic interactions between phototrophic and heterotrophic communities. However, particularly in streams, microbial functions vary significantly with the structure of the streambed, that is the distribution and spatial arrangement of sediment grains in the streambed. It is therefore essential to elucidate how environmental factors synergistically define the microbial turnover of terrestrial organic matter in order to better understand the ecological role of photo-heterotrophic interactions in stream ecosystem processes. In outdoor experimental streams, we examined how the structure of streambeds modifies the influence of light availability on microbial turnover of leaf carbon (C). Furthermore, we investigated whether the studied relationships of microbial leaf C turnover to environmental conditions are affected by flow intermittency commonly occurring in streams. We applied leaves enriched with a 13C-stable isotope tracer and combined quantitative and isotope analyses. We thereby elucidated whether treatment induced changes in C turnover were associated with altered use of leaf C within the microbial food web. Moreover, isotope analyses were combined with measurements of microbial community composition to determine whether changes in community function were associated with a change in community composition. In this study, we present evidence, that environmental factors interactively determine how phototrophs and heterotrophs contribute to leaf C turnover. Light availability promoted the utilization of leaf C within the microbial food web, which was likely associated with a promoted availability of highly bioavailable metabolites of phototrophic origin. However, our results additionally confirm that the structure of the streambed modifies light-related changes in microbial C turnover. From our observations, we conclude that the streambed structure influences the strength of photo-heterotrophic interactions by defining the spatial availability of algal metabolites in the streambed and the composition of microbial communities. Collectively, our multifactorial approach provides valuable insights into environmental controls on the functioning of stream ecosystems.

Community-level sensitivity of a calcifying ecosystem to acute in situ CO2 enrichment

The rate of change in ocean carbonate chemistry is a vital determinant in the magnitude of effects observed. Benthic marine ecosystems are facing an increasing risk of acute CO2 exposure that may be natural or anthropogenically derived (e.g. engineering and industrial activities). However, our understanding of how acute CO2 events impact marine life is restricted to individual organisms, with little understanding for how this manifests at the community level. Here, we investigated in situ the effect of acute CO2 enrichment on the coralline algal ecosystem—a globally ubiquitous, ecologically and economically important habitat, but one which is likely to be sensitive to CO2 enrichment due to its highly calcified reef-like structures engineered by coralline algae. Most notably, we observed a rapid community-level shift to favour net dissolution rather than net calcification. Smaller changes from net respiration to net photosynthesis were also observed. There was no effect on the net flux of DMS/DMSP (algal secondary metabolites), nor on the nutrients nitrate and phosphate. Following return to ambient CO2 levels, only a partial recovery was seen within the monitoring timeframe. This study highlights the sensitivity of biogenic carbonate marine communities to acute CO2 enrichment and raises concerns over the capacity for the system to ‘bounce back’ if subjected to repeated acute high-CO2 events.

In Vitro Response of Rumen Microbiota to the Antimethanogenic Red Macroalga Asparagopsis taxiformis.

The red macroalga Asparagopsis taxiformis has been shown to significantly decrease methane production by rumen microbial communities. This has been attributed to the bioaccumulation of halogenated methane analogues produced as algal secondary metabolites. The objective of this study was to evaluate the impact of A. taxiformis supplementation on the relative abundance of methanogens and microbial community structure during in vitro batch fermentation. Addition of A. taxiformis (2% organic matter) or the halogenated methane analogue bromoform (5μM) reduced methane production by over 99% compared to a basal substrate-only control. Quantitative PCR confirmed that the decrease in methane production was correlated with a decrease in the relative abundance of methanogens. High-throughput 16S ribosomal RNA gene amplicon sequencing showed that both treatments reduced the abundance of the three main orders of methanogens present in ruminants (Methanobacteriales, Methanomassiliicoccales and Methanomicrobiales). Shifts in bacterial community structure due to the addition of A. taxiformis and 5μM bromoform were similar and concomitant with increases in hydrogen concentration in the headspace of the fermenters. With high potency and broad-spectrum activity against rumen methanogens, A. taxiformis represents a promising natural strategy for reducing enteric methane emissions from ruminant livestock.

Antifouling Compounds from Marine Macroalgae.

Marine macroalgae produce a wide variety of biologically-active metabolites that have been developed into commercial products, such as antibiotics, immunosuppressive, anti-inflammatory, cytotoxic agents, and cosmetic products. Many marine algae remain clean over longer periods of time, suggesting their strong antifouling potential. Isolation of biogenic compounds and the determination of their structure could provide leads for the development of environmentally-friendly antifouling paints. Isolated substances with potent antifouling activity belong to fatty acids, lipopeptides, amides, alkaloids, lactones, steroids, terpenoids, and pyrroles. It is unclear as yet to what extent symbiotic microorganisms are involved in the synthesis of these compounds. Algal secondary metabolites have the potential to be produced commercially using genetic and metabolic engineering techniques. This review provides an overview of publications from 2010 to February 2017 about antifouling activity of green, brown, and red algae. Some researchers were focusing on antifouling compounds of brown macroalgae, while metabolites of green algae received less attention. Several studies tested antifouling activity against bacteria, microalgae and invertebrates, but in only a few studies was the quorum sensing inhibitory activity of marine macroalgae tested. Rarely, antifouling compounds from macroalgae were isolated and tested in an ecologically-relevant way.

Separation and identification of fatty acid esters of algal carotenoid metabolites in the freshwater mussel Dreissena bugensis, by liquid chromatography with ultraviolet/visible wavelength and mass spectrometric detectors in series

LC with photodiode array and APCI-ion trap mass spectrometry has made it possible to tentatively identify 76 carotenyl fatty acid esters (cFAEs) in solvent extracts from Dreissena bugensis, collected from Lake Erie: 16 mono- and 33 diFAEs of fucoxanthinol (FOH), and 27 diFAEs of mactraxanthin (MX). FOH and MX, previously identified in cFAE hydrolysates, were confirmed as parent carotenoids of the cFAEs, and as primary metabolites of fucoxanthin and violaxanthin, respectively, derived from diatoms and chlorophytes in the dreissenids’ diet. The most abundant fatty acid substituents of cFAEs were 16:0 and 16:1; abundant fatty acid biomarkers were 16:1 and 20:5, from diatoms, and 17:0, from bacteria. Cleanup of solvent extracts by solid phase extraction (Florisil) was necessary to reduce neutral background lipids, which interfered with detection of MX-diFAEs by APCI(+), and detection of FOH-diFAEs by APCI(+/−). The FOH-monoFAEs, MX-diFAEs and FOH-diFAEs were found to elute in a well-defined chromatographic order, by two regression models for retention times increasing as a function of: i) increasing number of carbons but decreasing number of double bonds in the fatty acid and decreasing number of non-esterified OH-groups on the parent carotenoids; ii) increasing dispersive but decreasing polar and hydrogen-bonding interactions, described by solubility parameters calculated for each cFAE. The best separations of the dreissenid cFAEs, with free OH-groups decreasing from four to one, were achieved between 20 and 68min, using a C18-column and moderately polar mobile phase (acetone, water), to obtain a reverse-phase gradient with a 56% decrease in hydrogen-bonding interactions.

Uncovering Potential Applications of Cyanobacteria and Algal Metabolites in Biology, Agriculture and Medicine: Current Status and Future Prospects.

Cyanobacteria and algae having complex photosynthetic systems can channelize absorbed solar energy into other forms of energy for production of food and metabolites. In addition, they are promising biocatalysts and can be used in the field of “white biotechnology” for enhancing the sustainable production of food, metabolites, and green energy sources such as biodiesel. In this review, an endeavor has been made to uncover the significance of various metabolites like phenolics, phytoene/terpenoids, phytols, sterols, free fatty acids, photoprotective compounds (MAAs, scytonemin, carotenoids, polysaccharides, halogenated compounds, etc.), phytohormones, cyanotoxins, biocides (algaecides, herbicides, and insecticides) etc. Apart from this, the importance of these metabolites as antibiotics, immunosuppressant, anticancer, antiviral, anti-inflammatory agent has also been discussed. Metabolites obtained from cyanobacteria and algae have several biotechnological, industrial, pharmaceutical, and cosmetic uses which have also been discussed in this review along with the emerging technology of their harvesting for enhancing the production of compounds like bioethanol, biofuel etc. at commercial level. In later sections, we have discussed genetically modified organisms and metabolite production from them. We have also briefly discussed the concept of bioprocessing highlighting the functioning of companies engaged in metabolites production as well as their cost effectiveness and challenges that are being addressed by these companies.

Liquid chromatography-high resolution mass spectrometric methods for the surveillance monitoring of cyanotoxins in freshwaters

A comprehensive risk management on human exposure to cyanotoxins, whose production is actually unpredictable, is limited by reliable analytical tools for monitoring as many toxic algal metabolites as possible. Two analytical approaches based on a LC-QTOF system for target analysis and suspect screening of cyanotoxins in freshwater were presented. A database with 369 compounds belonging to cyanobacterial metabolites was developed and used for a retrospective data analysis based on high resolution mass spectrometry (HRMS). HRMS fragmentation of the suspect cyanotoxin precursor ions was subsequently performed for correctly identifying the specific variants. Alternatively, an automatic tandem HRMS analysis tailored for cyanotoxins was performed in a single chromatographic run, using the developed database as a preferred precursor ions list. Twenty-five extracts of surface and drinking waters contaminated by cyanobacteria were processed. The identification of seven uncommon microcystins (M(O)R, MC-FR, MSer7-YR, D-Asp3MSer7-LR, MSer7-LR, dmAdda-LR and dmAdda-YR) and 6 anabaenopeptins (A, B, F, MM850, MM864, oscyllamide Y) was reported. Several isobaric variants, fully separated by chromatography, were pointed out. The developed methods are proposed to be used by environmental and health agencies for strengthening the surveillance monitoring of cyanotoxins in water.

Extracts of seaweeds as potential inhibitors of quorum sensing and bacterial growth

Macroalgae are an important source of antimicrobial compounds. However, it is unclear if these compounds are produced by the algae themselves, by their associated bacteria, or by both. The main aim of this study was to investigate the potential of macroalgae and their associated microorganisms to inhibit bacterial quorum sensing (QS) and growth. Before extraction, half of the algal specimens were treated with 30% ethanol to remove surface associated bacteria. Canistrocarpus cervicornis extracts were able to inhibit QS of the reporter Chromobacterium violaceum CV017, where extracts with associated bacteria were more efficient than those without bacteria. However, not all algal extracts that inhibited QS of CV017 were able to inhibit bacterial attachment of Pseudomonas aeruginosas PA01, showing specific activity of algal metabolites. Only 58% of the extracts showed antibacterial activity against eight marine fouling and pathogenic bacterial strains tested. Our data suggests that algae and their associated microbiota are important sources of antimicrobial compounds which potentially can be used in future biotechnological applications.

Antidiabetic studies of Chaetomorpha antennina extract using experimental models

Chaetomorpha antennina is a marine green alga found abundantly on the southern coast of India. This study explores the efficacy of C. antennina extracts in the management of diabetes using in vitro and in vivo models. The algal metabolites were extracted using various solvents and evaluated for inhibitory effect against key metabolic enzymes involved in blood sugar management and antioxidant property. Among the various extracts, methanolic extract of C. antennina (MECA) was found to be effective in all the inhibitory assays including, α-amylase (IC50 525.8 μg mL−1), α-glucosidase (IC50 121.3 μg mL−1), DPP-IV (IC50 24.92 μg mL−1) and antioxidant activity using DPPH (38 %) under in vitro conditions. In toxicity assays, MECA was nontoxic against mouse macrophage cells (J774) and red blood cells. Further, in vivo studies of MECA (250 mg kg−1 B.wt) on streptozotocin (STZ)-induced diabetic rats for a period of 28 days reduced the fasting blood glucose level to 39.97 % and that of positive control glibenclamide (0.25 mg kg−1 B.wt) was 73.05 % respectively. Serum cholesterol, triglycerides, ALT and AST were significantly decreased after 28 days of MECA treatment. GC-MS analysis of MECA showed the presence of ascorbic acid, octadecadienoate and fucosterol which were already identified for antidiabetic action. Overall, this study shows that the MECA exhibits antidiabetic activity in STZ-induced diabetic rats. Therefore, MECA can be considered for further studies to evaluate its mechanism for the effective management of diabetes.

Linking microbial diversity and functionality of arctic glacial surface habitats.

Distinct microbial habitats on glacial surfaces are dominated by snow and ice algae, which are the critical players and the dominant primary colonisers and net producers during the melt season. Here for the first time we have evaluated the role of these algae in association with the full microbial community composition (i.e., algae, bacteria, archaea) in distinct surface habitats and on 12 glaciers and permanent snow fields in Svalbard and Arctic Sweden. We cross-correlated these data with the analyses of specific metabolites such as fatty acids and pigments, and a full suite of potential critical physico-chemical parameters including major and minor nutrients, and trace metals. It has been shown that correlations between single algal species, metabolites, and specific geochemical parameters can be used to unravel mixed metabolic signals in complex communities, further assign them to single species and infer their functionality. The data also clearly show that the production of metabolites in snow and ice algae is driven mainly by nitrogen and less so by phosphorus limitation. This is especially important for the synthesis of secondary carotenoids, which cause a darkening of glacial surfaces leading to a decrease in surface albedo and eventually higher melting rates.

Understanding the invasion success of Sargassum muticum: herbivore preferences for native and invasive Sargassum spp

Several ecological models explain the success of introduced seaweeds by herbivore–prey interactions. The ‘enemy release hypothesis’ states that invaders benefit from a lack of natural enemies compared to the recipient community. The ‘novel weapons hypothesis,’ however, highlights the importance of chemical defense compounds of introduced species that are more effective in invaded regions than native counterparts. In order to explain the tremendous invasion success of the brown alga Sargassum muticum, we compared the palatability and nutritional value of S. muticum individuals from their native and invaded habitat (Japan and North Sea, respectively) with noninvasive congeneric species from Japan (S. fusiforme, S. horneri), and a native competitor from the North Sea (Fucus vesiculosus). Different feeding assays using artificial food with either freeze-dried algae or algal extracts and three dominant North Sea mesograzers were performed to detect feeding preferences. All herbivores preferred the local brown alga F. vesiculosus, followed by North Sea S. muticum, while Sargassum spp. from Japan were the least preferred. Since nutritional value did not correlate with feeding preference and algal extracts had the same effect as algal powder, we could demonstrate a deterrent activity of algal secondary metabolites. The preference of herbivores for the sympatric S. muticum population compared to the allopatric Japanese population could indicate a resource allocation from chemical defense to reproduction and growth. Due to the low palatability of Sargassum spp. from Japan, it might be reasonable to include additional Sargassum species in North Sea monitoring to prevent their establishment in European waters.

Surface metabolites of the brown alga Taonia atomaria have the ability to regulate epibiosis

This study aimed to improve understanding of the strategies developed by the Mediterranean seaweed Taonia atomaria to chemically control bacterial epibiosis. An experimental protocol was optimized to specifically extract algal surface-associated metabolites by a technique involving dipping in organic solvents whilst the integrity of algal cell membranes was assessed by fluorescent microscopy. This methodology was validated using mass spectrometry-based profiles of algal extracts and analysis of their principal components, which led to the selection of methanol as the extraction solvent with a maximum exposure time of 15 s. Six compounds (A–F) were identified in the resulting surface extracts. Two of these surface-associated compounds (B and C) showed selective anti-adhesion properties against reference bacterial strains isolated from artificial surfaces while remaining inactive against epibiotic bacteria of T. atomaria. Such specificity was not observed for commercial antifouling biocides and other molecules identified in the surface or whole-cell extracts of T. atomaria.

Metabolites from invasive pests inhibit mitochondrial complex II: A potential strategy for the treatment of human ovarian carcinoma?

The red pigment caulerpin, a secondary metabolite from the marine invasive green algae Caulerpa cylindracea can be accumulated and transferred along the trophic chain, with detrimental consequences on biodiversity and ecosystem functioning. Despite increasing research efforts to understand how caulerpin modifies fish physiology, little is known on the effects of algal metabolites on mammalian cells.Here we report for the first time the mitochondrial targeting activity of both caulerpin, and its closely related derivative caulerpinic acid, by using as experimental model rat liver mitochondria, a system in which bioenergetics mechanisms are not altered. Mitochondrial function was tested by polarographic and spectrophotometric methods.Both compounds were found to selectively inhibit respiratory complex II activity, while complexes I, III, and IV remained functional. These results led us to hypothesize that both algal metabolites could be used as antitumor agents in cell lines with defects in mitochondrial complex I. Ovarian cancer cisplatin-resistant cells are a good example of cell lines with a defective complex I function on which these molecules seem to have a toxic effect on proliferation. This provided novel insight toward the potential use of metabolites from invasive Caulerpa species for the treatment of human ovarian carcinoma cisplatin-resistant cells.

Investigation of the Genetics and Biochemistry of Roseobacticide Production in the Roseobacter Clade Bacterium Phaeobacter inhibens.

ABSTRACTRoseobacter clade bacteria are abundant in surface waters and are among the most metabolically diverse and ecologically significant species. This group includes opportunistic symbionts that associate with micro- and macroalgae. We have proposed that one representative member, Phaeobacter inhibens, engages in a dynamic symbiosis with the microalga Emiliania huxleyi. In one phase, mutualistically beneficial molecules are exchanged, including the Roseobacter-produced antibiotic tropodithietic acid (TDA), which is thought to protect the symbiotic interaction. In an alternative parasitic phase, triggered by algal senescence, the bacteria produce potent algaecides, the roseobacticides, which kill the algal host. Here, we employed genetic and biochemical screens to identify the roseobacticide biosynthetic gene cluster. By using a transposon mutagenesis approach, we found that genes required for TDA synthesis—the tda operon and paa catabolon—are also necessary for roseobacticide production. Thus, in contrast to the one-cluster–one-compound paradigm, the tda gene cluster can generate two sets of molecules with distinct structures and bioactivities. We further show that roseobacticide production is quorum sensing regulated via an N-acyl homoserine lactone signal (3-OH–C10-HSL). To ensure tight regulation of algaecide production, and thus of a lifestyle switch from mutualism to parasitism, roseobacticide biosynthesis necessitates the presence of both an algal senescence molecule and a quorum sensing signal.

Unique Polybrominated Hydrocarbons from the Australian Endemic Red Alga Ptilonia australasica.

The red alga Ptilonia australasica is endemic to Australian temperate waters. Chemical investigation of P. australasica led to the identification of four new polybrominated compounds, ptilones A-C (1-3) and australasol A (4). Their planar structures were established by extensive NMR and MS analyses. The low H/C ratio and the presence of a large number of heteroatoms made the structure elucidation challenging. The absolute configurations of 1, 2, and 4 were determined by quantum chemical ECD calculations employing time-dependent density functional theory. Ptilones A-C (1-3) show unique 4-ethyl-5-methylenecyclopent-2-enone (1 and 2) and 2-methyl-6-vinyl-4H-pyran-4-one (3) skeletons not previously reported in algal metabolites. Ptilone A displayed the most potent cytotoxicity against the human prostate cancer PC3 cells with an IC50 value of 0.44 μM and induced the PC3 cell cycle arrest in the G0/G1 phase.

Algal toxin profiles in Nigerian coastal waters (Gulf of Guinea) using passive sampling and liquid chromatography coupled to mass spectrometry

Algal toxins may accumulate in fish and shellfish and thus cause poisoning in consumers of seafood. Such toxins and the algae producing them are regularly surveyed in many countries, including Europe, North America, Japan and others. However, very little is known regards the occurrence of such algae and their toxins in most African countries. This paper reports on a survey of phytoplankton and algal toxins in Nigerian coastal waters.Seawater samples were obtained from four sites for phytoplankton identification, on three occasions between the middle of October 2014 and the end of February 2015 (Bar Beach and Lekki in Lagos State, Port Harcourt in Rivers State and Uyo in Akwa Ibom State). The phytoplankton community was generally dominated by diatoms and cyanobacteria; however several species of dinoflagellates were also identified: Dinophysis caudata, Lingulodinium polyedrum and two benthic species of Prorocentrum.Passive samplers (containing Diaion® HP-20 resin) were deployed for several 1-week periods on the same four sites to obtain profiles of algal toxins present in the seawater. Quantifiable amounts of okadaic acid (OA) and pectenotoxin 2 (PTX2), as well as traces of dinophysistoxin 1 (DTX1) were detected at several sites. Highest concentrations (60 ng OA g−1 HP-20 resin) were found at Lekki and Bar Beach stations, which also had the highest salinities. Non-targeted analysis using full-scan high resolution mass spectrometry showed that algal metabolites differed from site to site and for different sampling occasions. Screening against a marine natural products database indicated the potential presence of cyanobacterial compounds in the water column, which was also consistent with phytoplankton analysis.During this study, the occurrence of the marine dinoflagellate toxins OA and PTX2 has been demonstrated in coastal waters of Nigeria, despite unfavourable environmental conditions, with regards to the low salinities measured. Hence shellfish samples should be monitored in future to assess the risk for public health through accumulation of such toxins in seafood.

The Laurencia Paradox: An Endless Source of Chemodiversity.

Nature, the most prolific source of biological and chemical diversity, has provided mankind with treatments for health problems since ancient times and continues to be the most promising reservoir of bioactive chemicals for the development of modern drugs. In addition to the terrestrial organisms that still remain a promising source of new bioactive metabolites, the marine environment, covering approximately 70% of the Earth's surface and containing a largely unexplored biodiversity, offers an enormous resource for the discovery of novel compounds. According to the MarinLit database, more than 27,000 metabolites from marine macro- and microorganisms have been isolated to date providing material and key structures for the development of new products in the pharmaceutical, food, cosmeceutical, chemical, and agrochemical sectors. Algae, which thrive in the euphotic zone, were among the first marine organisms that were investigated as sources of food, nutritional supplements, soil fertilizers, and bioactive metabolites.Red algae of the genus Laurencia are accepted unanimously as one of the richest sources of new secondary metabolites. Their cosmopolitan distribution, along with the chemical variation influenced to a significant degree by environmental and genetic factors, have resulted in an endless parade of metabolites, often featuring multiple halogenation sites.The present contribution, covering the literature until August 2015, offers a comprehensive view of the chemical wealth and the taxonomic problems currently impeding chemical and biological investigations of the genus Laurencia. Since mollusks feeding on Laurencia are, in many cases, bioaccumulating, and utilize algal metabolites as chemical weaponry against natural enemies, metabolites of postulated dietary origin of sea hares that feed on Laurencia species are also included in the present review. Altogether, 1047 secondary metabolites, often featuring new carbocyclic skeletons, have been included.The chapter addresses: (1) the "Laurencia complex", the botanical description and the growth and population dynamics of the genus, as well as its chemical diversity and ecological relations; (2) the secondary metabolites, which are organized according to their chemical structures and are classified into sesquiterpenes, diterpenes, triterpenes, acetogenins, indoles, aromatic compounds, steroids, and miscellaneous compounds, as well as their sources of isolation which are depicted in tabulated form, and (3) the biological activity organized according to the biological target and the ecological functions of Laurencia metabolites.

MIB and 2,4‐D Removal by Biofilters During Episodic Loading

Episodic occurrences of trace organic contaminants may affect their removal by biofilters. Removal of the naturally occurring algal metabolite 2‐methylisoborneol (MIB) and the herbicide 2,4‐dichlorphenoxyacetic acid (2,4‐D) by seven biofilters with an average empty bed contact time (EBCT) of 8.7 min is presented under a range of intermittent exposure conditions with continuous presence of dissolved organic matter. An average 70% removal of both MIB and 2,4‐D was found under constant exposure conditions over seven months. With the use of a pseudo‐first‐order model, much of the variability in removal during this time could be explained by EBCT changes. Microorganisms in the biofilters retained the capacity to biodegrade MIB and 2,4‐D after non‐exposure periods of up to five months. However, after nine months of non‐exposure, the MIB and 2,4‐D removals were lower than with the control biofilter, although the biofilter began to quickly reacclimate to these contaminants.

Treatment technologies and mechanisms for three odorants at trace level: IPMP, IBMP, and TCA

Odour episodes caused by algal metabolites are gaining more and more attention in recent years. Besides geosmin and 2-methylisoborneol (MIB), 2-isopropyl-3-methoxypyrazine (IPMP), 2-isobutyl-3-methoxypyrazine (IBMP), and 2,4,6-trichloroanisole (TCA) have emerged to be important off-flavour sources. Their low odour threshold concentrations (several ng ·L−1), which are even lower than those of MIB and geosmin, pose challenges for treatment strategies. Hence, a practical and efficient mitigation technology is needed. The possible practical technologies, including powdered activated carbon (PAC) adsorption and oxidation by chlorine and potassium permanganate, were investigated. The results indicated that chlorine and potassium permanganate oxidation of the three odorants were unfeasible while PAC adsorption was effective. As for adsorption, TCA, followed by IBMP and IPMP, was most easily removed by PAC. The Freundlich model could well describe the adsorption isotherm data. The adsorption capacities for IPMP, IBMP, and TCA were described as follows: , , and . For five earthy/musty odorants including geosmin and MIB, octanol/water partition coefficient, molecular weight, and polarizability all promoted adsorption while aqueous solubility showed a negative influence. The hydrophobic interaction was believed to be the dominant force in the adsorption mechanism while the π-electron interaction enhanced adsorption when a benzene ring was present. This result could be used to predict the adsorption performance of emerging odorants.