纵条纹炭角菌子实体的化学成分研究
|
摘要
目的:研究纵条纹炭角菌子实体的化学成分。方法:采用正反相硅胶柱层析、Sephadex LH-20、制备薄层色谱等方法进行化合物分离,并通过核磁共振波谱进行结构鉴定。结果:从纵条纹炭角菌乙醇提取浸膏的乙酸乙酯萃取部位分离并鉴定了18个化合物,分别为:棕榈酸(1)、亚油酸甘油三酯(2)、油酸乙酯(3)、亚油酸乙酯(4)、油酸-α-单甘油酯(5)、麦角甾醇(6)、麦角甾-4,6,8(14),22-四烯-3-酮(7)、大戟二烯醇(8)、β-谷甾醇(9)、3,9-二羟基-3-甲基-6,8-二甲氧基-二氢蒽酮(10)、1-羟基-6,8-二甲氧基-3-甲基蒽醌(11)、5,7-二羟基-2-甲基-4-二氢色原酮(12)、5-羟基-2-甲基-4-二氢色原酮(13)、7-氨基-4-甲基香豆素(14)、过氧麦角甾醇(15)、9,11-去氢过氧麦角甾醇(16)、脑苷酯B(17)和脑苷酯D(18)。结论:所有化合物均为首次从该菌中分离得到。
Objective: To study the chemical compositions from fruiting bodies of Xylaria striata. Methods: Normal and reversed phase liquid chromatography,Sephadex LH-20,preparative TLC were applied for the isolation and purification of the compounds. NMR methods were used to identified the structures of the compositions. Results: Eighteen compounds were isolated from Xylaria striata fruiting bodies,which were identified as palmitic acid( 1),linoleic triglyceride( 2),ethyl oleate( 3),ethyl linoleate( 4),oleic acid-α-monoglyceride( 5),ergosterol( 6),ergosta-4,6,8( 14),22-tetraene-3-sterone( 7),euphadienol( 8),β-sitosterol( 9),3,9-dihydroxyl-3-methyl-6,8-dimethoxy-dihydrogen anthranone( 10),1-hydroxyl-6,8-dimethoxy-3-methylanthraquinone( 11),5,7-dihydroxyl-2-methyl-4-chromanone( 12),5-hydroxyl-2-methyl-4-chromanone( 13),7-amidogen-4-methylcoumarin( 14),peroxy-ergosterol( 15),9,11-dehydroperoxyergosterol( 16),cerebrozydy B( 17) and cerebrozydy D( 18). Conclusion: All the compounds are isolated from Xylaria striata for the first time.
Objective: To study the chemical compositions from fruiting bodies of Xylaria striata. Methods: Normal and reversed phase liquid chromatography,Sephadex LH-20,preparative TLC were applied for the isolation and purification of the compounds. NMR methods were used to identified the structures of the compositions. Results: Eighteen compounds were isolated from Xylaria striata fruiting bodies,which were identified as palmitic acid( 1),linoleic triglyceride( 2),ethyl oleate( 3),ethyl linoleate( 4),oleic acid-α-monoglyceride( 5),ergosterol( 6),ergosta-4,6,8( 14),22-tetraene-3-sterone( 7),euphadienol( 8),β-sitosterol( 9),3,9-dihydroxyl-3-methyl-6,8-dimethoxy-dihydrogen anthranone( 10),1-hydroxyl-6,8-dimethoxy-3-methylanthraquinone( 11),5,7-dihydroxyl-2-methyl-4-chromanone( 12),5-hydroxyl-2-methyl-4-chromanone( 13),7-amidogen-4-methylcoumarin( 14),peroxy-ergosterol( 15),9,11-dehydroperoxyergosterol( 16),cerebrozydy B( 17) and cerebrozydy D( 18). Conclusion: All the compounds are isolated from Xylaria striata for the first time.
引文
[1]高聪,罗俊,刘霞,等.炭角菌属真菌化学成分与生物活性研究进展[J].菌物学报,2016,35(7):767-781.
[2]麻兵继,阮元,刘吉开.长柄炭角菌子实体化学成分研究[J].天然产物研究与开发,2008,20(1):63-65.
[3]马橙,翁榕安,张平.黑柄炭角菌的研究进展[J].菌物研究,2009,7(1):59-62.
[4]贺新生.四川盆地蕈菌图志[M].北京:科学出版社,2011.
[5]马贝贝,霍存录,孙晓玲,等.纵条纹炭角菌子实体培养[J].食品与发酵科技,2013,49(2):44-46.
[6]袁小红,张春杰,郑仁林,等.六种高等真菌醇提物的抗肿瘤活性筛选[J].西南科技大学学报,2013,28(3):95-97.
[7]袁小红,张春杰,刘霞,等.6种高等真菌醇提物对植物病原菌的抗菌活性研究[J].安徽农业科学,2013,41(12):5289-5290.
[8]Yoo BR,Han JS.N,N-diarylammonium pyrosulfate as a highly effective reverse micelle-type catalyst for hydrolysis of esters[J].Organic Letters,2012,14(12):3194-3197.
[9]Mannina L,Luchinat C,Patumi M,et al.Concentration dependence of13C-NMR spectra of triglycerides:implications for the NMR analysis of olive oils[J].Magnetic Resonance in Chemistry,2015,38(10):886-890.
[10]陈淑娟,刘佳佳,龚汉祥,等.红豆杉内生真菌次生代谢物的分离鉴定及其抗菌活性分析[J].生物工程学报,2009,25(3):368-374.
[11]Jayaraman M,Ansell SM,Mui BL,et al.Maximizing the potency of siRNA lipid nanoparticles for hepatic gene silencing in vivo[J].Angew Chem Int Ed Engl,2012,124(34):8529-8533.
[12]朱娟娟,张超,王英姿,等.千金子石油醚部位化学成分的研究[J].山东中医药大学学报,2014,38(4):381-382.
[13]杨小龙,刘吉开,罗都强,等.黑柄炭角菌的化学成分[J].天然产物研究与开发,2011,23(5):846-849.
[14]Jong VYM,Ee GCL,Sukari MA,et al.Cycloartane triterpenoids acid from Garcinia eugenifolia[J].Asian Journal of Chemistry,2013,25(3):1199-1202.
[15]王兴娜,黄午阳,刘吉开,等.大炭角菌子实体化学成分的研究[J].中草药,2012,43(12):2327-2332.
[16]龚庆芳,张玉梅,谭宁华,等.黑柄炭角菌发酵菌丝体的化学成分研究[J].中国中药杂志,2008,33(11):1269-1272.
[17]Liu X,Dong M,Chen X,et al.Antimicrobial activity of an endophytic Xylaria sp YX-28 and identification of its antimicrobial compound 7-amino-4-methylcoumarin[J].Applied Microbiology and Biotechnology,2008,78(2):241-247.
[18]Chen YK,Kuo YH,Chiang BH,et al.Cytotoxic activities of 9,11-dehydroergosterol peroxide and ergosterol peroxide from the fermentation mycelia of Ganoderma lucidum cultivated in the medium containing leguminous plants on Hep 3B Cells[J].Journal of Agricultural and Food Chemistry,2009,57(13):5713-5719.
[19]Kawai G,Ikeda Y.Structure of biologically active and inactive cerebrosides prepared from Schizophyllum commune[J].Lipid Res,1985,26(3):338-343.
[2]麻兵继,阮元,刘吉开.长柄炭角菌子实体化学成分研究[J].天然产物研究与开发,2008,20(1):63-65.
[3]马橙,翁榕安,张平.黑柄炭角菌的研究进展[J].菌物研究,2009,7(1):59-62.
[4]贺新生.四川盆地蕈菌图志[M].北京:科学出版社,2011.
[5]马贝贝,霍存录,孙晓玲,等.纵条纹炭角菌子实体培养[J].食品与发酵科技,2013,49(2):44-46.
[6]袁小红,张春杰,郑仁林,等.六种高等真菌醇提物的抗肿瘤活性筛选[J].西南科技大学学报,2013,28(3):95-97.
[7]袁小红,张春杰,刘霞,等.6种高等真菌醇提物对植物病原菌的抗菌活性研究[J].安徽农业科学,2013,41(12):5289-5290.
[8]Yoo BR,Han JS.N,N-diarylammonium pyrosulfate as a highly effective reverse micelle-type catalyst for hydrolysis of esters[J].Organic Letters,2012,14(12):3194-3197.
[9]Mannina L,Luchinat C,Patumi M,et al.Concentration dependence of13C-NMR spectra of triglycerides:implications for the NMR analysis of olive oils[J].Magnetic Resonance in Chemistry,2015,38(10):886-890.
[10]陈淑娟,刘佳佳,龚汉祥,等.红豆杉内生真菌次生代谢物的分离鉴定及其抗菌活性分析[J].生物工程学报,2009,25(3):368-374.
[11]Jayaraman M,Ansell SM,Mui BL,et al.Maximizing the potency of siRNA lipid nanoparticles for hepatic gene silencing in vivo[J].Angew Chem Int Ed Engl,2012,124(34):8529-8533.
[12]朱娟娟,张超,王英姿,等.千金子石油醚部位化学成分的研究[J].山东中医药大学学报,2014,38(4):381-382.
[13]杨小龙,刘吉开,罗都强,等.黑柄炭角菌的化学成分[J].天然产物研究与开发,2011,23(5):846-849.
[14]Jong VYM,Ee GCL,Sukari MA,et al.Cycloartane triterpenoids acid from Garcinia eugenifolia[J].Asian Journal of Chemistry,2013,25(3):1199-1202.
[15]王兴娜,黄午阳,刘吉开,等.大炭角菌子实体化学成分的研究[J].中草药,2012,43(12):2327-2332.
[16]龚庆芳,张玉梅,谭宁华,等.黑柄炭角菌发酵菌丝体的化学成分研究[J].中国中药杂志,2008,33(11):1269-1272.
[17]Liu X,Dong M,Chen X,et al.Antimicrobial activity of an endophytic Xylaria sp YX-28 and identification of its antimicrobial compound 7-amino-4-methylcoumarin[J].Applied Microbiology and Biotechnology,2008,78(2):241-247.
[18]Chen YK,Kuo YH,Chiang BH,et al.Cytotoxic activities of 9,11-dehydroergosterol peroxide and ergosterol peroxide from the fermentation mycelia of Ganoderma lucidum cultivated in the medium containing leguminous plants on Hep 3B Cells[J].Journal of Agricultural and Food Chemistry,2009,57(13):5713-5719.
[19]Kawai G,Ikeda Y.Structure of biologically active and inactive cerebrosides prepared from Schizophyllum commune[J].Lipid Res,1985,26(3):338-343.