闽浙马尾杉内生真菌Hypoxylon investiens NX9的次级代谢产物与乙酰胆碱酯酶抑制活性The Secondary Metabolites of Hypoxylon investiens NX9 and Their Anti-acetylcholinesterase Activities
张会;石绵绵;李伟;吴水生;王明兹;郑永标;
摘要(Abstract):
研究闽浙马尾杉内生真菌炭团菌Hypoxylon investiens NX9的次级代谢产物及其对乙酰胆碱酯酶的抑制活性.将菌株H.investiens NX9进行液体发酵20 L,用乙酸乙酯萃取得到4.448 g有机粗提物,采用色谱技术从中分离到6个萘酮衍生物和1个倍半萜类化合物,根据核磁波谱数据分别鉴定为(S)-regiolone (1)、3,4-dihydro-3,6,8-trihydroxy-3-methyl-naphthalenone (2)、xylarenone (3)、(3S,4R)-3,4-dihydro-3,4,5-trihydroxynaphthalen-1(2H)-one (4)、4,5-dihydroxy--tetralone (5)、3,4-dihydro-3,4,8-trihydr-oxy-1-naphthalenone (6)和xylaranol B (7).乙酰胆碱酯酶抑制实验显示化合物3具有一定的活性,ρ_(IC50)为5.23 mg·mL~(-1).研究表明以药用植物的内生菌为资源,是发现活性药物的一条有效途径.
关键词(KeyWords): 马尾杉;炭团菌;乙酰胆碱酯酶
基金项目(Foundation): 福建省自然科学基金资助项目(2016J01353);; 福建省科技厅社会发展引导性(重点)项目(2016Y0030);; 福建师范大学化学免疫学创新团队项目(IRT1703)
作者(Author): 张会;石绵绵;李伟;吴水生;王明兹;郑永标;
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参考文献(References):
- [1]LIU J S,ZHU Y L,YU C M,et al.The structures of Huperzine A and B,two new alkaloids exhibiting marked anticholinesterase activity [J].Canadian Journal of Chemistry,1986,64(4):837-839.
- [2]FERREIRA A,RODRIGUES M,FORTUNA A,et al.Huperzine A from Huperzia serrata:a review of its sources,chemistry,pharmacology and toxicology [J].Phytochemistry Reviews,2016,15(1):51-85.
- [3]GARCíA M V,VON POSER G L,APEL M,et al.Anticholinesterase activity and identification of Huperzine a in three Mexican lycopods:Huperzia cuernavacensis,Huperzia dichotoma and Huperzia linifolia (Lycopodiaceae) [J].Pakistan Journal of Pharmaceutical Sciences,2017,30(S):235-239.
- [4]MA X Q,JIANG S H,ZHU D Y.Alkaloid patterns in Huperzia and some related genera of Lycopodiaceae sensu lato occurring in China and their contribution to classification [J].Biochemical Systematics & Ecology,1998,26(7):723-728.
- [5]张丽兵,孔宪需.中国马尾杉属拟石杉组(新组)的分类研究及马尾杉属的属下分类 [J].植物分类学报,1999,37(1):40-53.
- [6]CHUONG N N,HUONG N T T,HUNG T M,et al.Anti-cholinesterase activity of Lycopodium alkaloids from Vietnamese Huperzia squarrosa (Forst.) Trevis [J].Molecules,2014,19(11):19172-19179.
- [7]STIERLE A,STROBEL G,STIERLE D.Taxol and taxane production by Taxomyces andreanae,an endophytic fungus of Pacific yew [J].Science,1993,260(5105):214-216.
- [8]张方方,王明兹,刘海元,等.闽浙马尾杉内生真菌炭团菌NX9产石杉碱甲的发酵条件优化 [J].中国医药工业杂志,2015,46(8):827-832.
- [9]ZHOU Y,YANG B,JIANG Y,et al.Studies on cytotoxic activity against HepG-2 cells of naphthoquinones from green walnut husks of Juglans mandshurica Maxim [J].Molecules,2015,20(9):15572-15588.
- [10]NICOLET B,TABACCHI R.Secondary metabolites produced by Stagonospora sp.,a potential biocontrol agent against bindweeds [C]//Lyr H,Russell PE and Sisler HD (eds).12th International Reinhardsbrunn Symposium-Modern Fungicides and Antifungal Compounds Ⅱ .Andover:Intercept Limited,United Kingdom,1999:469-476.
- [11]RUKACHAISIRIKUL V,SOMMART U,PHONGPAICHIT S,et al.Metabolites from the xylariaceous fungus PSU-A80 [J].Chemical and Pharmaceutical Bulletin,2007,55(9):1316-1318.
- [12]YAN S,LI S,WU W,et al.Terpenoid and phenolic metabolites from the fungus Xylaria sp.associated with termite nests [J].Chemistry & Biodiversity,2011,8(9):1689-1700.
- [13]LIU J X,DI D L,WEI X N,et al.Cytotoxic diarylheptanoids from the pericarps of walnuts (Juglans regia) [J].Planta Medica,2008,74(7):754-759.
- [14]IWASAKI S,MURO H,NOZOE S,et al.Isolation of 3,4-dihydro-3,4,8-trihydroxy-1 (2H)-naphthalenone and tenuazonic acid from Pyricularia oryzae cavara [J].Tetrahedron Letters,1972,13(1):13-16.
- [15]YAMAGUCHI Y,MASUMA R,KIM Y-P,et al.Taxonomy and secondary metabolites of Pseudobotrytis sp.FKA-25 [J].Mycoscience,2004,45(1):9-16.
- [16]LI Y Y,HU Z Y,LU C H,et al.Four new terpenoids from Xylaria sp.101 [J].Helvetica Chimica Acta,2010,93(4):796-802.
- [17]DINGOVA D,LEROY J,CHECK A,et al.Optimal detection of cholinesterase activity in biological samples:modifications to the standard Ellman’s assay [J].Analytical Biochemistry,2014,462:67-75.
- [18]张静爽,王蓉.阿尔茨海默病发生机制的研究进展 [J].首都医科大学学报,2014,35(6):721-724.
- [19]ASSOCIATION A S.2017 Alzheimer’s disease facts and figures [J].Alzheimer’s & Dementia,2017,13(4):325-373.
- [20]CHEN Y G.Research progress in the pathogenesis of Alzheimer’s disease [J].Chinese Medical Journal,2018,131(13):1618-1624.
- [21]DAVIS K L,POWCHICK P.Tacrine [J].The Lancet,1995,345(8950):625-630.
- [22]BRYSON H M,BENFIELD P.Donepezil [J].Drugs & Aging,1997,10(3):234-239.
- [23]EMRE M,AARSLAND D,ALBANESE A,et al.Rivastigmine for dementia associated with Parkinson’s disease [J].New England Journal of Medicine,2004,351(24):2509-2518.
- [24]OLIN J,SCHNEIDER L.Galantamine for dementia due to Alzheimer’s disease [J].The Cochrane Database of Systematic Reviews,2002(3):1-67.