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Chemical Compound Review:

MCYST-RR (5R,8S,11R,12S,15S,18R,19S,22R )-8,15-bis[3...

Synonyms: microcystin RR, AC1O5PJE, LS-182802, C19995, 111755-37-4, ...

Maizels, M. et al., McElhiney, J. et al., Kubwabo, C. et al., McElhiney, J. et al., Yin, L. et al., et al.

Blom, Robinson, Jüttner, Yin, Huang, Huang, Li, Liu, Kubwabo, Vais, Benoit, Tsuji, Asakawa, Anzai, Sumino, Harada,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of microcystin RR

The cyanobacteria toxins anatoxin-a, microcystin-LR, microcystin-RR, microcystin-YR, and nodularin were separated in less than 30 min on several 1 mm x 15 cm reversed-phase liquid chromatography (LC) columns, and their electrospray mass spectra were measured using injections of 50 ng or less with a benchtop time-of-flight (TOF) mass spectrometer [1].
These structural differences may contribute to the observed differences in toxicity of microcystin-RR and microcystin-LR [2].
The results revealed that microcystin-RR concentrations above 100 microg x L(-1) significantly inhibited the growth of Synechococcus elongatus [3].
It was found to cross react with three other microcystin variants - microcystin-RR, microcystin-LW and microcystin-LF - and detected microcystins in extracts of the cyanobacterium Microcystis aeruginosa, found to contain the toxins by high-performance liquid chromatography (HPLC) [4].
Loach received 75 mg of dry cells/kg body weight mass (equal to 10 microg microcystin-RR/kg body mass), for 28 days under controlled conditions [5].

Psychiatry related information on microcystin RR

The operating parameters such as hydrogen peroxide dosage, pH value, UV light intensity, initial concentration of microcystin-RR and reaction time were evaluated, respectively [6].

High impact information on microcystin RR

Perfusions with either microcystin-LR or microcystin-RR initiated 15-26 min after nuclear envelope breakdown extended the metaphase transit times significantly [7].
Microcystin-RR-induced apoptosis in tobacco BY-2 cells [8].
We assessed changes in activities of both detoxification and antioxidant enzymes as well as lipid peroxidation levels in liver, gill, intestine and brain of Corydoras paleatus exposed to dissolved microcystin-RR (MC-RR) [9].
The activities of superoxide dismutase (SOD) and catalase (CAT) increased significantly after 48 h exposure to 1 and 5mg/L of microcystin-RR, but glutathione S-transferase (GST) activity showed no difference compared with the control [10].
Uptake, tissue distribution and accumulation of microcystin-RR in Corydoras paleatus, Jenynsia multidentata and Odontesthes bonariensis. A field and laboratory study [11].

Biological context of microcystin RR

Results showed that microcystin-RR evoked decline of the cell viability to approximately 80% after treating for 144 h [12].
Microcystin-RR affected seedling growth (IC50 0.8 microg/ml) and microcystin concentrations > or =5.0 microg/ml produced malformed plants [13].
Growth and development detection revealed that V. natans was relatively insensitive to microcystin-RR at concentrations ranging from 0.0001 to 0.01 mg/L [14].
In order to determine the microcystin RR LD50, purified microcystin RR was injected into the peritoneum of the quails [15].

Anatomical context of microcystin RR

In this study, tobacco BY-2 suspension cell line was applied to examine the effects of microcystin-RR on plant cells [12].

Associations of microcystin RR with other chemical compounds

The most sensitive single-chain antibody (scAb) isolated was capable of detecting microcystin-LR at levels below the World Health Organization limit in drinking water (1 microg liter(-1)) and cross-reacted with three other purified microcystin variants (microcystin-RR, -LW, and -LF) and the related cyanotoxin nodularin [16].

Gene context of microcystin RR

Three different commercial standards of microcystin-RR were assessed for purity by the liquid chromatography coupled with electrospray ionization mass spectrometry (LC/ESI/MS) technique [17].
Microcystin-LR (MLR) and microcystin-RR (MRR) were purified from cyanobacterial cell materials by extraction, Sephadex LH-20-, ODS silica gel-, ionic exchange and RP-HPLC-chromatography [18].

Analytical, diagnostic and therapeutic context of microcystin RR

Using high-performance liquid chromatography (HPLC), three hepatotoxins were identified, microcystin RR being the most frequent and present in highest amounts, LR, and YR [19].
Identification of microcystin-RR and [Dha7]microcystin-RR in commercial standards by electrospray ionization mass spectrometry [17].
Microcystin-RR was added to the lake water at regular intervals and the degradation after 24h was observed in the bioreactor over a 72-d period [20].
We also found that microcystin-RR can induce tobacco cell apoptosis in a dose- and time-dependent manner with flow cytometry analysis [8].
The compound was isolated in high purity, and its 24-h acute grazer toxicity was compared with microcystin-LR, microcystin-RR, microcystin-YR, and nodularin using a Thamnocephalus platyurus bioassay [21].

References

A LC/MS method for the determination of cyanobacteria toxins in water. Maizels, M., Budde, W.L. Anal. Chem. (2004) [Pubmed]
The solution NMR structure of a blue-green algae hepatotoxin, microcystin-RR--a comparison with the structure of microcystin-LR. Trogen, G.B., Edlund, U., Larsson, G., Sethson, I. Eur. J. Biochem. (1998) [Pubmed]
Physiological and biochemical analyses of microcystin-RR toxicity to the cyanobacterium Synechococcus elongatus. Hu, Z.Q., Liu, Y.D., Li, D.H. Environ. Toxicol. (2004) [Pubmed]
Detection and quantification of microcystins (cyanobacterial hepatotoxins) with recombinant antibody fragments isolated from a naïve human phage display library. McElhiney, J., Lawton, L.A., Porter, A.J. FEMS Microbiol. Lett. (2000) [Pubmed]
Oral exposure to Microcystis increases activity-augmented antioxidant enzymes in the liver of loach (Misgurnus mizolepis) and has no effect on lipid peroxidation. Li, X.Y., Chung, I.K., Kim, J.I., Lee, J.A. Comp. Biochem. Physiol. C Toxicol. Pharmacol. (2005) [Pubmed]
Degradation of microcystin-RR by UV radiation in the presence of hydrogen peroxide. Qiao, R.P., Li, N., Qi, X.H., Wang, Q.S., Zhuang, Y.Y. Toxicon (2005) [Pubmed]
Changes in the metaphase transit times and the pattern of sister chromatid separation in stamen hair cells of Tradescantia after treatment with protein phosphatase inhibitors. Wolniak, S.M., Larsen, P.M. J. Cell. Sci. (1992) [Pubmed]
Microcystin-RR-induced apoptosis in tobacco BY-2 cells. Yin, L., Huang, J., Li, W., Liu, Y. Toxicon (2006) [Pubmed]
Differential detoxification and antioxidant response in diverse organs of Corydoras paleatus experimentally exposed to microcystin-RR. Cazenave, J., Bistoni, M.d.e. .L., Pesce, S.F., Wunderlin, D.A. Aquat. Toxicol. (2006) [Pubmed]
Responses of antioxidant system in Arabidopsis thaliana suspension cells to the toxicity of microcystin-RR. Yin, L., Huang, J., Huang, W., Li, D., Liu, Y. Toxicon (2005) [Pubmed]
Uptake, tissue distribution and accumulation of microcystin-RR in Corydoras paleatus, Jenynsia multidentata and Odontesthes bonariensis. A field and laboratory study. Cazenave, J., Wunderlin, D.A., de Los Angeles Bistoni, M., Amé, M.V., Krause, E., Pflugmacher, S., Wiegand, C. Aquat. Toxicol. (2005) [Pubmed]
Microcystin-RR-induced accumulation of reactive oxygen species and alteration of antioxidant systems in tobacco BY-2 cells. Yin, L., Huang, J., Huang, W., Li, D., Wang, G., Liu, Y. Toxicon (2005) [Pubmed]
Microcystin uptake inhibits growth and protein phosphatase activity in mustard (Sinapis alba L.) seedlings. Kurki-Helasmo, K., Meriluoto, J. Toxicon (1998) [Pubmed]
Microcystin-RR uptake and its effects on the growth of submerged macrophyte Vallisneria natans (lour.) hara. Yin, L., Huang, J., Li, D., Liu, Y. Environ. Toxicol. (2005) [Pubmed]
Quail spleen is enlarged by microcystin RR as a blue-green algal hepatotoxin. Takahashi, S., Kaya, K. Nat. Toxins (1993) [Pubmed]
Rapid isolation of a single-chain antibody against the cyanobacterial toxin microcystin-LR by phage display and its use in the immunoaffinity concentration of microcystins from water. McElhiney, J., Drever, M., Lawton, L.A., Porter, A.J. Appl. Environ. Microbiol. (2002) [Pubmed]
Identification of microcystin-RR and [Dha7]microcystin-RR in commercial standards by electrospray ionization mass spectrometry. Kubwabo, C., Vais, N., Benoit, F.M. Journal of AOAC International. (2004) [Pubmed]
Generation of antibodies directed against the low-immunogenic peptide-toxins microcystin-LR/RR and nodularin. Baier, W., Loleit, M., Fischer, B., Jung, G., Neumann, U., Weiss, M., Weckesser, J., Hoffmann, P., Bessler, W.G., Mittenbühler, K. Int. J. Immunopharmacol. (2000) [Pubmed]
Microcystins in Slovene freshwaters (central Europe)--first report. Sedmak, B., Kosi, G. Nat. Toxins (1997) [Pubmed]
Degradation of microcystins using immobilized microorganism isolated in an eutrophic lake. Tsuji, K., Asakawa, M., Anzai, Y., Sumino, T., Harada, K. Chemosphere (2006) [Pubmed]
High grazer toxicity of [D-Asp(3),(E)-Dhb(7)]microcystin-RR of Planktothrix rubescens as compared to different microcystins. Blom, J.F., Robinson, J.A., Jüttner, F. Toxicon (2001) [Pubmed]

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