灰树花化学成分及药理活性研究进展
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摘要
通过查阅近30年的国内外相关研究文献,对灰树花中的化学成分及药理活性研究进展进行了综述。结果表明:截至目前已从灰树花中分离鉴定出主要多糖组分11个,甾类化合物21个,酚类化合物7个,以及醇类、酯类、酮类等其他多种化合物。灰树花主要有抗肿瘤、抗病毒、增强免疫、抑菌等药理作用。本文为灰树花的进一步研究提供了参考资料。
The chemical constituents and pharmacological activities of Grifola frondosa were summarized by reviewing the Chinese and foreign literatures in recent 30 years. The results showed that 11 main polysaccharides,21 steroidal compounds,7 phenols compounds,as well as alcohols,esters,ketones and a variety of other compounds had been isolated and identified. Grifola frondosa has anti-tumor,anti-virus,enhance immunity,antibacterial and other pharmacological effects.This paper provided research data for further study on Grifola frondosa.
The chemical constituents and pharmacological activities of Grifola frondosa were summarized by reviewing the Chinese and foreign literatures in recent 30 years. The results showed that 11 main polysaccharides,21 steroidal compounds,7 phenols compounds,as well as alcohols,esters,ketones and a variety of other compounds had been isolated and identified. Grifola frondosa has anti-tumor,anti-virus,enhance immunity,antibacterial and other pharmacological effects.This paper provided research data for further study on Grifola frondosa.
引文
[1]孙欣怡.灰树花胞外多糖和胞内锌多糖的提取优化及抗氧化研究[D].泰安:山东农业大学,2014.
[2]李小定,荣建华,吴谋成.灰树花多糖药理研究进展[J].天然产物研究与开发,2003,15(4):364-368.
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[4]韩省华,林胜龙,张东平.灰树花在百山祖山区的发生及其规律[J].食药用菌,1994,13(2):36.
[5]Kato K,Inagaki T,Teranishi T.Structural analysis of the alkalisolubleβ-d-glucan from the fruit body of Grifola frondosa[J].Carbohydrate Research,1983,124(2):247-252.
[6]Nanba H,Hishida I,Kuroda H.Antitumor activity exhibited by orally administered extract from fruit body of Grifola frondosa(maitake)[J].Chemical&Pharmaceutical Bulletin,1988,36(5):1819-1827.
[7]Ohno N,Suzuki I,Oikawa S,et al.Antitumor activity and structural characterization of glucans extracted from cultured fruit bodies of Grifola frondosa[J].Chemical&Pharmaceutical Bulletin,1984,32(3):1142-1151.
[8]Ohno N,Ohsawa M,Sato K,et al.Conformation of grifolan in the fruit body of Grifola frondosa assessed by carbon-13 cross polarization-magic angle spinning nuclear magnetic resonance spectroscopy[J].Chemical&Pharmaceutical Bulletin,1987,35(6):2585-2588.
[9]Ohno N,Iino K,Oikawa S,et al.Fractionation of acidic antitumor beta-glucan of Grifola frondosa by anion-exchange chromatography using urea solutions of low and high ionic strengths[J].Chemical&Pharmaceutical Bulletin,1986,34(8):3328-3332.
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[30]庞菲.灰树花化学成分及抗肿瘤细胞增殖作用研究[D].武汉:华东师范大学,2010.
[31]Ishizuka T,Yaoita Y,Kikuchi M.Sterol Constituents from the Fruit Bodies of Grifola frondosa(FR.)S.F.GRAY.[J].Cheminform,2010,29(18):1756-1760.
[32]Marina Della Greca,Antonio Fiorentino,Antonio Molinaro,et al.Steroidal 5,6-Epoxides from Arum italicum[J].Natural Product Letters,1993,2(1):27-32.
[33]Kinjo J,Kishida F,Watanabe K,et al.Five new triterpene glycosides from Russell lupine[J].Chemical&Pharmaceutical Bulletin,1994,42(9):1874-1878.
[34]Chen R,Wang Y,Yu D.Studies on the chemical constituents of the spores from Ganoderma lucidum[J].Acta Botanica Sinica,1991,33(1):65-68.
[35]Notaro G,Piccialli V,Sica D,et al.ChemInform Abstract:studies towards the synthesis of polyoxygenated steroids.Part3.Reaction of 7,9(11)-Diene Steroids with RuO4.[J/OL].Cheminform,1994,25(34)[2018-05-30].http:∥doi.org/10.1002/chin.199434209.
[36]Takaishi Y,Uda M,Ohashi T,et al.Glycosides of ergosterol derivatives from Hericum erinacens[J].Phytochemistry,1991,30(12):4117-4120.
[37]Ohta K,Yaoita Y,Matsuda N,et al.Sterol constituents from the sclerotium of Polyporus umbellatus fries[J].Natural Medicines,1996,50:179-181.
[38]Kawagishi H,Katsumi R,Sazawa T,et al.Cytotoxic steroids from the mushroom Agaricus blazei[J].Phytochemistry,1988,27(27):2777-2779.
[39]Ohta K,Yaoita Y,Kikuchi M.Sterols from Sclerotium of Polyporus umbellatus Fries(Natural Medicine Note)[J].Natural Medicines,1996,50(5):366.
[40]Sheffer M,Fried A,Gottlieb H E,et al.Lipid composition of the plasma-membrane of the halotolerant alga,Dunaliella salina[J].Biochimica et Biophysica Acta(BBA)-Biomembranes,1986,857(2):165-172.
[41]吕旭聪,贾瑞博,李燕,等.灰树花抗氧化活性多酚的提取纯化及其鉴定[J].中国酿造,2016,35(3):74-79.
[42]马迪.灰树花子实体次生代谢产物的分离纯化及生物活性研究[D].上海:华东理工大学,2015.
[43]杨生兵.灰树花子实体和发酵菌丝体成分及多糖比较研究[D].无锡:江南大学,2012.
[44]孟梦.灰树花多糖的分离纯化及其抗肿瘤作用机理的研究[D].天津:天津科技大学,2013.
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[46]Kodama N,Komuta K,Nanba H.Can maitake MD-fraction aid cancer patients?[J].Alternative Medicine Review A Journal of Clinical Therapeutic,2002,7(3):236-239.
[47]赵霏.灰树花多糖联合维生素C诱导肝癌细胞SMMC-7721凋亡与自噬的研究[D].兰州:兰州大学,2016.
[48]Xiao-Lei M A,Meng M,Han L R,et al.Immunomodulatory activity of macromolecular polysaccharide isolated from Grifola frondosa[J].Chinese Journal of Natural Medicines,2015,13(12):906-914.
[49]韩丽荣,程代,王莉蕊,等.灰树花胞外多糖的结构及免疫调节活性[J].生物工程学报,2016,32(5):648-656.
[50]葛健康,张佰鹏,吴梧桐,等.灰树花子实体多糖提取物对2型糖尿病小鼠的治疗作用[J].西北药学杂志,2008,23(6):372-374.
[51]杨庆伟,王芃,孙昊.灰树花菌丝体多糖的降血脂作用[J].天津职业院校联合学报,2014,19(10):76-79.
[52]项哨,朱圣禾,朱永平,等.灰树花多糖在小鼠体内抗病毒作用的研究[J].浙江大学学报:医学版,1995,60(5):203-205.
[53]Zhao C,Gao L,Wang C,et al.Structural characterization and antiviral activity of a novel heteropolysaccharide isolated from Grifola frondosa,against enterovirus 71[J].Carbohydrate Polymers,2015,144:382-389.
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[2]李小定,荣建华,吴谋成.灰树花多糖药理研究进展[J].天然产物研究与开发,2003,15(4):364-368.
[3]韩省华.食药两用真菌---灰树花[J].新农业,2010,40(8):7-8.
[4]韩省华,林胜龙,张东平.灰树花在百山祖山区的发生及其规律[J].食药用菌,1994,13(2):36.
[5]Kato K,Inagaki T,Teranishi T.Structural analysis of the alkalisolubleβ-d-glucan from the fruit body of Grifola frondosa[J].Carbohydrate Research,1983,124(2):247-252.
[6]Nanba H,Hishida I,Kuroda H.Antitumor activity exhibited by orally administered extract from fruit body of Grifola frondosa(maitake)[J].Chemical&Pharmaceutical Bulletin,1988,36(5):1819-1827.
[7]Ohno N,Suzuki I,Oikawa S,et al.Antitumor activity and structural characterization of glucans extracted from cultured fruit bodies of Grifola frondosa[J].Chemical&Pharmaceutical Bulletin,1984,32(3):1142-1151.
[8]Ohno N,Ohsawa M,Sato K,et al.Conformation of grifolan in the fruit body of Grifola frondosa assessed by carbon-13 cross polarization-magic angle spinning nuclear magnetic resonance spectroscopy[J].Chemical&Pharmaceutical Bulletin,1987,35(6):2585-2588.
[9]Ohno N,Iino K,Oikawa S,et al.Fractionation of acidic antitumor beta-glucan of Grifola frondosa by anion-exchange chromatography using urea solutions of low and high ionic strengths[J].Chemical&Pharmaceutical Bulletin,1986,34(8):3328-3332.
[10]Mizuno T,Ohsawa K,Hagiwara N,et al.Studies on the hostmediated antitumor polysaccharides.Part IX.Fractionation and characterization of antitumor polysaccharides from maitake,Grifola frondosa[J].Agricultural&Biological Chemistry,1986,50(7):1679-1688.
[11]Zhuang C,Mizuno T,Ito H,et al.Chemical modification and antitumor activity of polysaccharides from the mycelium of liquid-cultured Grifola frondosa[J].Journal of the Japanese Society for Food Science&Technology,1994,41(1):733-740.
[12]Kubo K,Aoki H,Nanba H.Anti-diabetic activity present in the fruit body of Grifola frondosa(Maitake).I[J].Biological&Pharmaceutical Bulletin,1994,17(8):1106-1110.
[13]冯慧琴,杨庆尧,杨晓彤,等.灰树花子实体多糖和菌丝体多糖的比较分析[J].华东师范大学学报:自然科学版,2001,47(3):91-96.
[14]李小定.灰树花多糖的结构及其生物活性[D].武汉:华中农业大学,2002.
[15]陈向东,刘晓雯,吴梧桐.低分子量灰树花多糖的分离、纯化和抗肿瘤活性[J].Chinese Journal of Natural Medicines,2006,4(1):77-80.
[16]Yang B K,Gu Y A,Jeong Y T,et al.Chemical characteristics and immuno-modulating activities of exo-biopolymers produced by Grifola frondosa,during submerged fermentation process[J].International Journal of Biological Macromolecules,2007,41(3):227-233.
[17]Nie X,Shi B,Ding Y,et al.Preparation of a chemically sulfated polysaccharide derived from Grifola frondosa,and its potential biological activities[J].International Journal of Biological Macromolecules,2006,39(4/5):228-233.
[18]Bi Y,Ye M,Han Y,et al.Biological and physicochemical properties of two polysaccharides from the mycelia of Grifola umbellate[J].Carbohydrate Polymers,2013,95(2):740-745.
[19]Zhou C,Qiao Y,Tang Q,et al.Purification and characterization of a novel small-molecule polysaccharide from the Maitake medicinal mushroom Grifola frondosa(higher Basidiomycetes)[J].International Journal of Medicinal Mushrooms,2013,15(2):145-152.
[20]Cui F,Zan X,Li Y,et al.Purification and partial characterization of a novel anti-tumor glycoprotein from cultured mycelia of Grifola frondosa[J].International Journal of Biological Macromolecules,2013,62(11):684-690.
[21]Ying W,Shen X,Liao W,et al.A heteropolysaccharide,l-fucod-manno-1,6-α-d-galactan extracted from Grifola frondosa,and antiangiogenic activity of its sulfated derivative[J].Carbohydrate Polymers,2014,101(1):631-641.
[22]Mao G H,Ren Y,Feng W W,et al.Antitumor and immunomodulatory activity of a water-soluble polysaccharide from Grifola frondosa[J].Carbohydrate Polymers,2015,134:406-412.
[23]Mao G H,Ren Y,Li Q,et al.Anti-tumor and immunomodulatory activity of selenium(Se)-polysaccharide from Se-enriched Grifola frondosa[J].International Journal of Biological Macromolecules,2016,82:607-613.
[24]Nanba H,Hamaguchi A,Kuroda H.The chemical structure of an antitumor polysaccharide in fruit bodies of Grifola frondosa(maitake)[J].Chemical&Pharmaceutical Bulletin,1987,35(3):1162-1168.
[25]Kubo K,Nanba H.Antitumor substance extracted from grifola:US,US 5854404 A[P].1998.
[26]Masuda Y,Kodama N,Nanba H.Macrophage J774.1 cell is activated by MZ-Fraction(Klasma-MZ)polysaccharide in Grifola frondosa[J].Mycoscience,2006,47(6):360-366.
[27]Zhuang C,Kawagishi H,Preuss H G.Glycoprotein with antidiabetic,antihypertensive,antiobesity and antihyperlipidemic effects from Grifola frondosa,and a method for preparing same:US,US 7214778 B2[P].2007.
[28]Cui F J,Tao W Y,Xu Z H,et al.Structural analysis of antitumor heteropolysaccharide GFPS1b from the cultured mycelia of Grifola frondosa,GF9801[J].Bioresource Technology,2007,98(2):395-401.
[29]Rui T,Adachi Y,Ishibashi K I,et al.An unambiguous structural elucidation of a 1,3-β-d-glucan obtained from liquid-cultured Grifola frondosa,by solution NMR experiments[J].Carbohydrate Research,2009,344(3):400-404.
[30]庞菲.灰树花化学成分及抗肿瘤细胞增殖作用研究[D].武汉:华东师范大学,2010.
[31]Ishizuka T,Yaoita Y,Kikuchi M.Sterol Constituents from the Fruit Bodies of Grifola frondosa(FR.)S.F.GRAY.[J].Cheminform,2010,29(18):1756-1760.
[32]Marina Della Greca,Antonio Fiorentino,Antonio Molinaro,et al.Steroidal 5,6-Epoxides from Arum italicum[J].Natural Product Letters,1993,2(1):27-32.
[33]Kinjo J,Kishida F,Watanabe K,et al.Five new triterpene glycosides from Russell lupine[J].Chemical&Pharmaceutical Bulletin,1994,42(9):1874-1878.
[34]Chen R,Wang Y,Yu D.Studies on the chemical constituents of the spores from Ganoderma lucidum[J].Acta Botanica Sinica,1991,33(1):65-68.
[35]Notaro G,Piccialli V,Sica D,et al.ChemInform Abstract:studies towards the synthesis of polyoxygenated steroids.Part3.Reaction of 7,9(11)-Diene Steroids with RuO4.[J/OL].Cheminform,1994,25(34)[2018-05-30].http:∥doi.org/10.1002/chin.199434209.
[36]Takaishi Y,Uda M,Ohashi T,et al.Glycosides of ergosterol derivatives from Hericum erinacens[J].Phytochemistry,1991,30(12):4117-4120.
[37]Ohta K,Yaoita Y,Matsuda N,et al.Sterol constituents from the sclerotium of Polyporus umbellatus fries[J].Natural Medicines,1996,50:179-181.
[38]Kawagishi H,Katsumi R,Sazawa T,et al.Cytotoxic steroids from the mushroom Agaricus blazei[J].Phytochemistry,1988,27(27):2777-2779.
[39]Ohta K,Yaoita Y,Kikuchi M.Sterols from Sclerotium of Polyporus umbellatus Fries(Natural Medicine Note)[J].Natural Medicines,1996,50(5):366.
[40]Sheffer M,Fried A,Gottlieb H E,et al.Lipid composition of the plasma-membrane of the halotolerant alga,Dunaliella salina[J].Biochimica et Biophysica Acta(BBA)-Biomembranes,1986,857(2):165-172.
[41]吕旭聪,贾瑞博,李燕,等.灰树花抗氧化活性多酚的提取纯化及其鉴定[J].中国酿造,2016,35(3):74-79.
[42]马迪.灰树花子实体次生代谢产物的分离纯化及生物活性研究[D].上海:华东理工大学,2015.
[43]杨生兵.灰树花子实体和发酵菌丝体成分及多糖比较研究[D].无锡:江南大学,2012.
[44]孟梦.灰树花多糖的分离纯化及其抗肿瘤作用机理的研究[D].天津:天津科技大学,2013.
[45]Ohno N,Suzuki I,Sato K,et al.Purification and structural characterization of an antitumorβ-1,3-glucan isolated from hot water extract of the fruit body of cultured Grifola frondosa[J].Chemical&Pharmaceutical Bulletin,1985,33(10):4522-4527.
[46]Kodama N,Komuta K,Nanba H.Can maitake MD-fraction aid cancer patients?[J].Alternative Medicine Review A Journal of Clinical Therapeutic,2002,7(3):236-239.
[47]赵霏.灰树花多糖联合维生素C诱导肝癌细胞SMMC-7721凋亡与自噬的研究[D].兰州:兰州大学,2016.
[48]Xiao-Lei M A,Meng M,Han L R,et al.Immunomodulatory activity of macromolecular polysaccharide isolated from Grifola frondosa[J].Chinese Journal of Natural Medicines,2015,13(12):906-914.
[49]韩丽荣,程代,王莉蕊,等.灰树花胞外多糖的结构及免疫调节活性[J].生物工程学报,2016,32(5):648-656.
[50]葛健康,张佰鹏,吴梧桐,等.灰树花子实体多糖提取物对2型糖尿病小鼠的治疗作用[J].西北药学杂志,2008,23(6):372-374.
[51]杨庆伟,王芃,孙昊.灰树花菌丝体多糖的降血脂作用[J].天津职业院校联合学报,2014,19(10):76-79.
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