2-methylisoborneol and beta-cyclocitral

Microcystis aeruginosa and Pseudanabaena are two common cyanobacterial species/genus and they can occur coincidently in many eutrophic lakes globally. These two cyanobacteria could produce Taste & Odor (T&O) compounds, and their production of T&O compounds might be changed when they are present coincidently. The amounts of T&O compounds and their producers may influence the effectiveness of water treatment processes. Therefore, the mutual interactions between Microcystis aeruginosa (FACHB-905, M) and Pseudanabaena sp. (FACHB-1277, P) on T&O compounds in co-cultures were evaluated in this study. Different initial cell concentrations of M and P, with ratios of M:P = 1:1, M:P = 1:2 and M:P = 2:1 were applied in the co-cultures. The growth of M was enhanced under all of the cyanobacterial cell ratios. The growth of P was enhanced under the ratio of M:P = 1:1, while it was inhibited under the ratios of M:P = 1:2 and M: P = 2:1. In addition, the growth of the two cyanobacteria and their production of β-cyclocitral and 2-methylisoborneol (2-MIB) in the filtrate of P were higher than those in the filtrate of M, which may be attributed to their associated secondary metabolites. The cell integrity and photosynthetic capacity of the two studied cyanobacteria are greatly affected by exposure to β-cyclocitral and 2-MIB. The results showed that β-cyclocitral and 2-MIB had the allelopathic effects on the two cyanobacteria species which might influence the composition of co-existing cyanobacteria and their production of T&O compounds.

Topics: Aldehydes; Camphanes; Cyanobacteria; Diterpenes; Ecology; Lakes; Microcystis; Odorants; Photosynthesis; Taste

Organic matter-induced black bloom frequently occurs in a number of large eutrophic shallow lakes; this can result in the release of malodorous compounds and has a negative impact on water quality. In the study, a microcosm system containing Zizania latifolia (Z. latifolia), a common aquatic plant, was established and the release of seven taste and odour compounds, dimethyl sulphide (DMS), dimethyl disulphide (DMDS), dimethyl trisulphide (DMTS), 2-methylisoborneol (MIB), geosmin (GSM), β-cyclocitral, and β-ionone, was investigated. The results showed that these compounds were all detected during Z. latifolia decay, and that volatile organic sulphur compounds (VOSCs), such as DMS, DMDS, and DMTS, were the main factors responsible for the strong foul odour (the maximum reached 5.0 μg L

Topics: Aldehydes; Biodegradation, Environmental; Camphanes; Diterpenes; Ecosystem; Lakes; Naphthols; Norisoprenoids; Odorants; Poaceae; Sulfides; Taste; Volatile Organic Compounds; Water Quality

The odor problem caused by the decay of aquatic plants is widespread in many freshwater lakes. In this study, the spatial distributions of seven taste and odor (T&O) compounds (dimethyl sulfide, dimethyl disulfide, dimethyl trisulfide, 2-methylisoborneol, geosmin, β-cyclocitral, and β-ionone) in the sediments and overlying water of the east of Taihu Lake were investigated. The effects of plant and physico-chemical parameters on the release of T&O compounds were also analyzed. The results showed that high concentrations of T&O compounds were detected in the area where Eichhornia crassipes was flourishing. Volatile organic sulfur compounds were not found in the water source area, which was not covered by aquatic plants. High plant biomass and aquiculture activities might increase the release of the taste and odor compounds. The correlation between the concentrations of odorous compounds and nutrients in the sediment was also analyzed. The production of odorants was positively correlated with the nitrogen, and they may migrate from sediment to overlying water. The result suggested that controlling the plant density and aquaculture activities could reduce the release of odorous compounds.

Topics: Aldehydes; Aquatic Organisms; Camphanes; China; Diterpenes; Geologic Sediments; Lakes; Naphthols; Norisoprenoids; Odorants; Plants; Sulfides; Taste; Volatile Organic Compounds; Water Pollutants, Chemical

Taste and odor (T&O) compounds are widespread in water environments and have attracted considerable public attention. Nowadays, the standard detections of these chemicals rely mainly on off-line methods such as GC-MS or evaluation by trained analysts' senses. In this study, we report a method for the rapid detection of T&O compounds in water by exploiting a newly invented chemi-ionization source, in combination with headspace vapor measurement at room temperature. The calibrated limits of detection (LODs) of 2-methylbutyraldehyde, methyl tert-butyl ether (MTBE), methyl methacrylate (MMA), 2-isobutyl-3-methyoxypyrazine (IBMP), and 2-isopropyl-3-methoxypyrazine (IPMP) are in the range of 3.5-50.2 ng L

Topics: Aldehydes; Camphanes; China; Diterpenes; Limit of Detection; Mass Spectrometry; Naphthols; Odorants; Pyrazines; Reproducibility of Results; Rivers; Taste; Water Pollutants, Chemical

Off-flavors are among the most troublesome compounds in the environment worldwide. The lack of a viable theory for studying the sources, distribution, and effect of odors has necessitated the accurate measurement of odors from environmental compartments. A rapid and flexible microwave-assisted purge-and-trap extraction device for simultaneously determining five predominant odors, namely, dimethyltrisulfide, 2-methylisoborneol, geosmin, β-cyclocitral and β-ionone, from the primary sources and sinks is demonstrated. This instrument facilitates the extraction and concentration of odors from quite different matrices simultaneously. This device is a solvent-free automated system that does not require cleaning and is timesaving. The calibration curves of the five odor compounds showed good linearity in the range of 1-500 ng/L, with correlation coefficients above 0.999 (levels=7) and with residuals ranging from approximately 77% to 104%. The limits of detection (S/N=3) were below 0.15 ng/L in algae sample and 0.07 ng/g in sediment and fish tissue samples. The relative standard deviations were between 2.65% and 7.29% (n=6). Thus the proposed design is ready for rapid translation into a standard analytical tool and is useful for multiple applications in the analysis of off-flavors.

Topics: Aldehydes; Animals; Camphanes; Chemical Fractionation; Chlorophyta; Diterpenes; Equipment Design; Fishes; Gas Chromatography-Mass Spectrometry; Geologic Sediments; Limit of Detection; Linear Models; Microwaves; Naphthols; Norisoprenoids; Odorants; Reproducibility of Results

Production and fate of taste and odor (T&O) compounds in natural waters are a pressing environmental issue. Simultaneous determination of these complex compounds (covering a wide range of boiling points) has been difficult. A simple and sensitive method for the determination of eight malodors products of cyanobacterial blooms was developed using automatic purge and trap (P&T) coupled with gas chromatography-mass spectrometry (GC-MS). This extraction and concentration technique is solvent-free. Dimethylsulfide (DMS), dimethyltrisulfide (DMTS), 2-isopropyl-3-methoxypyrazine (IPMP), 2-isobutyl-3-methoxypyrazine (IBMP), 2-methylisoborneol (MIB), β-cyclocitral, geosmin (GSM) and β-ionone were separated within 15.3 min. P&T uses trap #07 and high-purity nitrogen purge gas. The calibration curves of the eight odors show good linearity in the range of 1-500 ng/L with a correlation coefficient above 0.999 (levels=8) and with residuals ranging from approximately 83% to 124%. The limits of detection (LOD) (S/N=3) are all below 1.5 ng/L that of GSM is even lower at 0.08 ng/L. The relative standard deviations (RSD) are between 3.38% and 8.59% (n=5) and recoveries of the analytes from water samples of a eutrophic lake are between 80.54% and 114.91%. This method could be widely employed for monitoring these eight odors in natural waters.

Topics: Adsorption; Aldehydes; Camphanes; Diterpenes; Eutrophication; Fresh Water; Gas Chromatography-Mass Spectrometry; Naphthols; Norisoprenoids; Odorants; Pyrazines; Reproducibility of Results; Sensitivity and Specificity; Sulfides; Temperature

An exploratory study on the management of undesirable cyanobacteria blooms with respect to off-flavor problems using an integrated vertical-flow constructed wetland (CW) was performed at a small commercial-scale channel catfish farm from 2004 to 2007. The results of the three-year experiment indicated that water treatment by the CW could reduce the possibility of dominance by undesirable cyanobacteria species that often cause off-flavor problems. A detailed investigation in 2007, showed that the concentrations of geosmin, MIB (2-methylisoborneol), and β-cyclocitral in the water of the recirculating pond (4.3ngL(-1), U.D. (undetected) and 0.2ngL(-1), respectively) treated by the CW were significantly lower than those in the control pond (152.6ngL(-1), 63.3ngL(-1) and 254.8ngL(-1), respectively). In addition, the relationships among the cyanobacteria species, the off-flavor compounds and ten environmental variables were explored by canonical correspondence analysis (CCA). The results showed that Oscillatoria sp., Oscillatoria kawamurae and Microcystis aeruginosa were the main sources of off-flavor compounds in the catfish ponds. The successful manipulation of undesirable cyanobacteria species potentially resulted in lower concentrations of odorous compounds in the water of the recirculating pond. An investigation of the concentrations of geosmin and MIB in catfish fillets showed that the levels of odorous compounds were below the OTC (odor threshold concentration) values in the recirculating pond but were above the OTC values from July to October in the control pond. Water recycling by the CW could potentially be one of the best management practices to control off-flavor occurrences in aquaculture.

Topics: Aldehydes; Animals; Aquaculture; Camphanes; Cyanobacteria; Diterpenes; Environmental Monitoring; Eutrophication; Feeding Behavior; Ictaluridae; Naphthols; Odorants; Phytoplankton; Ponds; Seasons; Survival Analysis; Waste Disposal, Fluid; Water Movements; Water Pollutants, Chemical; Water Quality; Wetlands

A systematic study was conducted on seasonal and spatial patterns of taste and odor (T&O) compounds with relation to biotic and abiotic parameters at fifteen sites in Gonghu Bay of Lake Taihu in 2008. We developed a sensitive and automated method to simultaneously analyze eight T&O compounds (boiling points ranging from 38°C to 239°C) by using Purge-and-Trap (P&T) coupled with GC/MS. Maximum particulate dimethyl trisulfide (DMTS, 69.6 ng/L) exceeded its odor threshold concentrations (OTC, 10 ng/L) and maximum dissolved DMTS was 6.1 ng/L, but still far below concentration in the drinking water pollution incident of Wuxi City in 2007 when DMTS reached 1768-11,399 ng/L. Geosmin (GEO), 2-methylisoborneol (MIB), β-cyclocitral, β-ionone and 2-isobutyl-3-methoxypyrazine (IBMP) occasionally or frequently exceeded their OTCs, whereas 2-isopropyl-3-methoxypyrazine (IPMP) and dimethyl sulfide (DMS) did not. We found for the first time significant correlations between particulate β-cyclocitral and β-ionon concentrations and intracellular and extracellular microcystin concentrations. Spatially, Nanquan Waterworks faced more risk by T&O contamination than Xidong Waterworks. High concentrations of NO(3)-N, TDN and TN could be risky signs of taste and odor events by DMS, DMTS, IPMP, IBMP and GEO.

Topics: Aldehydes; Camphanes; China; Diterpenes; Environmental Monitoring; Fresh Water; Microcystins; Naphthols; Norisoprenoids; Odorants; Phytoplankton; Pyrazines; Seasons; Sulfides; Taste; Water Pollutants, Chemical; Water Supply

One of bacteria collected from Lake Sagami, Japan, Brevibacillus sp., was found to have a lytic activity of cyanobacteria, but did not produce active compounds. Instead, the co-culturing of Microcystis with the Brevibacillus sp. enhanced the production of two volatile compounds, beta-cyclocitral and 3-methyl-1-butanol, and the former had a characteristic lytic activity. It was confirmed that these volatile compounds were derived from the cyanobacteria themselves. beta-Ionone, geosmin and 2-methylisoborneol derived from cyanobacteria and similar volatile compounds, terpenoids, produced by plants also had a lytic activity. The minimum inhibitory concentration values of the cyanobacterial metabolites were estimated to be higher than those of compounds from plants except for a few compounds. Among them, beta-cyclocitral only produced a characteristic color change of culture broth from green to blue. This color change is similar to the phenomenon observed when a sudden decline in growth of cyanobacteria begins in a natural environment.

Topics: Aldehydes; Bacteriolysis; Camphanes; Cyanobacteria; Diterpenes; Japan; Molecular Structure; Naphthols; Norisoprenoids; Organic Chemicals; Pentanols; Terpenes; Volatilization

Lake Dianchi is the sixth largest freshwater lake in China. The pilot experimental area (6 km2) in Lake Dianchi is one of the most severely polluted areas in the lake with heavy cyanobacteria blooms. During June 2002 to May 2003, the algal composition and number, and odorous compounds were identified monthly and monitored in the area. Meanwhile, physicochemical parameters such as total phosphorus (TP), total nitrogen (TN), 5-day biochemical oxygen demand (BOD5), chemical oxygen demand (COD(Mn)), dissolved oxygen (DO), pH, transparency, temperature and chlorophyll a (chla) were determined. Four odorous compounds: 2-methylisoborneol (MIB), geosmin, beta-cyclocitral and beta-ionone were found in the lake water. Both the concentration of particulate beta-cyclocitral and that of beta-ionone correlated significantly with the annual variation of Chla, biomass of total phytoplankton, cyanobacteria and Microcystis. The concentration of particulate MIB correlated significantly with the biomass of Oscillatoria, while the concentration of particulate geosmin correlated significantly with the biomass of Anabaena. Off-flavour in the pilot area was found to be caused by a combination of beta-cyclocitral- and beta-ionone-producing Microcystis, MIB-producing Oscillatoria and geosmin-producing Anabaena. beta-ionone, MIB and geosmin contributed collectively to the odour intensity in the lake water.

Topics: Aldehydes; Camphanes; China; Chlorophyll; Chlorophyll A; Diterpenes; Environmental Monitoring; Eutrophication; Fresh Water; Naphthols; Nitrogen; Norisoprenoids; Oxygen; Phosphorus; Phytoplankton; Water Pollutants, Chemical; Water Purification