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  • N-Acetylnorloline

    N-Acetylnorloline

    N-Acetylnorloline
    产品编号 CFN00293
    CAS编号 38964-35-1
    分子式 = 分子量 C9H14N2O2 = 182.22
    产品纯度 >=98%
    物理属性 Oil
    化合物类型 Alkaloids
    植物来源 The roots of Neotyphodium uncinatum -infected meadow fescue.
    ChemFaces的产品在影响因子大于5的优秀和顶级科学期刊中被引用
    提供自定义包装
    产品名称 产品编号 CAS编号 包装 QQ客服
    N-Acetylnorloline CFN00293 38964-35-1 1mg QQ客服:2056216494
    N-Acetylnorloline CFN00293 38964-35-1 5mg QQ客服:2056216494
    N-Acetylnorloline CFN00293 38964-35-1 10mg QQ客服:2056216494
    N-Acetylnorloline CFN00293 38964-35-1 20mg QQ客服:2056216494
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    ChemFaces的产品在许多优秀和顶级科学期刊中被引用

    Cell. 2018 Jan 11;172(1-2):249-261.e12.
    doi: 10.1016/j.cell.2017.12.019.
    IF=36.216(2019)

    PMID: 29328914

    Cell Metab. 2020 Mar 3;31(3):534-548.e5.
    doi: 10.1016/j.cmet.2020.01.002.
    IF=22.415(2019)

    PMID: 32004475

    Mol Cell. 2017 Nov 16;68(4):673-685.e6.
    doi: 10.1016/j.molcel.2017.10.022.
    IF=14.548(2019)

    PMID: 29149595

    ACS Nano. 2018 Apr 24;12(4): 3385-3396.
    doi: 10.1021/acsnano.7b08969.
    IF=13.903(2019)

    PMID: 29553709

    Nature Plants. 2016 Dec 22;3: 16206.
    doi: 10.1038/nplants.2016.205.
    IF=13.297(2019)

    PMID: 28005066

    Sci Adv. 2018 Oct 24;4(10): eaat6994.
    doi: 10.1126/sciadv.aat6994.
    IF=12.804(2019)

    PMID: 30417089
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  • Seoul National University (Korea)
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  • 国外学术期刊发表的引用ChemFaces产品的部分文献
  • J Agric Food Chem.2021, 69(11):3496-3510.
  • Asian J Beauty Cosmetol2019, 17(3):287-294
  • Int J Mol Sci.2018, 19(9):E2601
  • Molecules.2016, 21(6)
  • Int Immunopharmacol.2021, 101(Pt A):108181.
  • Pharm Biol.2016, 54(7):1255-62
  • Int J Mol Med.2019, 43(6):2516-2522
  • Cytotechnology.2017, 69(5):765-773
  • BMC Complement Altern Med.2014, 14:352
  • Korean Journal of Pharmacognosy2018, 49(3):270-277
  • Biomed Pharmacother.2021, 139:111585.
  • PLoS One.2017, 12(8):e0181191
  • Molecules.2019, 24(2):E343
  • Sci Rep.2019, 9:19059
  • Front Pharmacol.2021, 12:615157.
  • Korean J. Crop Sci.2018, 63(2):131-139
  • J Ginseng Res.2022, 46(1):104-114.
  • The Japan Society for Analy. Chem.2017, 66(8):613-617
  • PLoS One.2018, 13(11):e0208055
  • Food and Fermentation Industries2018, 44(371)
  • Journal of Functional Foods2022, 91:105019.
  • The Japan Society for Analytical Chemistry2018, 67(4):201-206
  • J Nat Prod.2022, 85(5):1351-1362.
  • ...
  • 生物活性
    Description: High levels of N-acetyl norloline and peramine may be of particular importance for developing 'friendly' endophyte-enhanced turf and pasture grasses that resist challenging lepidopteran pests. N-acetyl norloline, which is produced by the Max P endophyte, may be responsible for a new form of toxicity called equine fescue oedema in horses.
    In vitro:
    PLoS One. 2014 Dec 22;9(12):e115590.
    Enzymes from fungal and plant origin required for chemical diversification of insecticidal loline alkaloids in grass-Epichloë symbiota.[Pubmed: 25531527]
    The lolines are a class of bioprotective alkaloids that are produced by Epichloë species, fungal endophytes of grasses. These alkaloids are saturated 1-aminopyrrolizidines with a C2 to C7 ether bridge, and are structurally differentiated by the various modifications of the 1-amino group: -NH2 (norloline), -NHCH3 (loline), -N(CH3)2 (N-methylloline), -N(CH3)Ac (N-acetylloline), -NHAc (N-acetylnorloline), and -N(CH3)CHO (N-formylloline). Other than the LolP cytochrome P450, which is required for conversion of N-methylloline to N-formylloline, the enzymatic steps for loline diversification have not yet been established.
    METHODS AND RESULTS:
    Through isotopic labeling, we determined that N-acetylnorloline is the first fully cyclized loline alkaloid, implying that deacetylation, methylation, and acetylation steps are all involved in loline alkaloid diversification. Two genes of the loline alkaloid biosynthesis (LOL) gene cluster, lolN and lolM, were predicted to encode an N-acetamidase (deacetylase) and a methyltransferase, respectively. A knockout strain lacking both lolN and lolM stopped the biosynthesis at N-acetylnorloline, and complementation with the two wild-type genes restored production of N-formylloline and N-acetylloline. These results indicated that lolN and lolM are required in the steps from N-acetylnorloline to other lolines. The function of LolM as an N-methyltransferase was confirmed by its heterologous expression in yeast resulting in conversion of norloline to loline, and of loline to N-methylloline. One of the more abundant lolines, N-acetylloline, was observed in some but not all plants with symbiotic Epichloë siegelii, and when provided with exogenous loline, asymbiotic meadow fescue (Lolium pratense) plants produced N-acetylloline, suggesting that a plant acetyltransferase catalyzes N-acetylloline formation.
    CONCLUSIONS:
    We conclude that although most loline alkaloid biosynthesis reactions are catalyzed by fungal enzymes, both fungal and plant enzymes are responsible for the chemical diversification steps in symbio.
    Environ. Entomol., 2011, 40(3):639-47.
    Endophyte-mediated resistance to black cutworm as a function of plant cultivar and endophyte strain in tall fescue.[Pubmed: 22251642]

    METHODS AND RESULTS:
    To improve Neotyphodium endophyte-mediated resistance to black cutworm Agrotis ipsilon (Hufnagel) (BCW), a series of experiments was conducted by using several different cultivars of tall fescue, Schedonorus arundinaceus (Schreb.) Dumort. in combination with several different haplotypes of the endophyte Neotyphodium coenophialum (Morgan-Jones & Gams) (plant cultivar × endophyte haplotype = plant line), each producing unique alkaloid profiles. BCW settling response, survival at 5 and 10 d, and larval biomass varied significantly among plant lines. In general, greater variation BCW performance was observed within a single plant cultivar infected with different endophyte haplotypes than among different plant cultivars infected with the same endophyte haplotype, but comparisons among the former were far more numerous. Although five endophyte-mediated alkaloids representing three alkaloid classes were quantified in the plants, the pyrrolizidine alkaloid N-acetyl norloline was consistently the single best predictor of BCW performance. BCW settling response, 5-d survival, and 10-d survival decreased as levels of the alkaloid N-acetyl norloline increased. The same three response variables also decreased with increasing levels of peramine, but increased with increasing levels of ergovaline. Minor variation in endophyte infection levels occurring among infected plant lines had no significant influence on BCW performance.
    CONCLUSIONS:
    Results indicate a potentially important role for N-acetyl norloline and peramine in providing resistance to black cutworm whereas ergovaline appears to be much less important. Therefore, endophyte haplotypes expressing high levels of N-acetyl norloline and peramine may be of particular importance for developing 'friendly' endophyte-enhanced turf and pasture grasses that resist challenging lepidopteran pests, although remaining safe for wildlife and grazing mammals.
    制备储备液(仅供参考)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 5.4879 mL 27.4394 mL 54.8787 mL 109.7574 mL 137.1968 mL
    5 mM 1.0976 mL 5.4879 mL 10.9757 mL 21.9515 mL 27.4394 mL
    10 mM 0.5488 mL 2.7439 mL 5.4879 mL 10.9757 mL 13.7197 mL
    50 mM 0.1098 mL 0.5488 mL 1.0976 mL 2.1951 mL 2.7439 mL
    100 mM 0.0549 mL 0.2744 mL 0.5488 mL 1.0976 mL 1.372 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    部分图片展示
    产品名称 产品编号 CAS编号 分子式 = 分子量 位单 联系QQ
    黑麦草碱; Loline CFN00291 25161-91-5 C8H14N2O = 154.21 5mg QQ客服:1457312923
    N-Demethylloine; N-Demethylloine CFN00292 4839-19-4 C7H12N2O = 140.18 5mg QQ客服:2159513211
    N-Acetylnorloline; N-Acetylnorloline CFN00293 38964-35-1 C9H14N2O2 = 182.22 5mg QQ客服:1457312923
    脱皮腺荚豆碱; Decorticasine CFN00294 1380-03-6 C10H16N2O2 = 196.25 5mg QQ客服:3257982914
    N-Acetyl-5,6-dehydrololine; N-Acetyl-5,6-dehydrololine CFN00295 194205-01-1 C10H14N2O2 = 194.23 5mg QQ客服:3257982914

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