灵芝子实体中三萜类物质抗肿瘤活性的谱效关系
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摘要
通过HPLC指纹图谱结合多元线性回归分析对不同产地灵芝子实体的功效性特征进行评价,为寻找灵芝中活性三萜提供理论依据。利用高效液相分析方法,结合样品对肿瘤细胞L1210的增殖抑制率,运用"中药色谱指纹图谱相似度评价系统2004A版"软件和多元线性回归分析11批不同品种灵芝子实体中的三萜活性成分。样品与标准指纹图谱的相似度均在0.9以上,共标定了12个共有物质峰,其中与抗L1210肿瘤细胞活性关系密切的三萜物质有灵芝酸C2、灵芝酸G、灵芝烯酸B、灵芝烯酸A、灵芝酸K、灵芝酸A、灵芝酸F和灵芝醛A。
HPLC fingerprint and principal component multiple linear regression analysis were used to evaluate the functional characteristics of Ganoderma lingzhi fruiting bodies from different producing areas for the purposes of providing a theoretical basis for searching active triterpenoids in Ganoderma lingzhi. Based on HPLC fingerprint in combination with the inhibition rate of L1210 tumor cell proliferation. The triterpene active components in 11 batches of Ganoderma lingzhi fruit body samples were analysed by using the software "similarity evaluation system of Chinese medicine chromatogram fingerprint" and multiple linear regression analysis. The result showed that the similarity between the sample and the standard fingerprint was all over 0.9. A total of 12 common substance peaks were identified, of which the triterpenoids with anti-L1210 tumor cell activity included ganoderic acid C2, ganoderic acid G, ganoderenic acid B, ganoderenic acid A, ganoderic acid K, ganoderic acid A, ganoderic acid F and ganoderal A.
HPLC fingerprint and principal component multiple linear regression analysis were used to evaluate the functional characteristics of Ganoderma lingzhi fruiting bodies from different producing areas for the purposes of providing a theoretical basis for searching active triterpenoids in Ganoderma lingzhi. Based on HPLC fingerprint in combination with the inhibition rate of L1210 tumor cell proliferation. The triterpene active components in 11 batches of Ganoderma lingzhi fruit body samples were analysed by using the software "similarity evaluation system of Chinese medicine chromatogram fingerprint" and multiple linear regression analysis. The result showed that the similarity between the sample and the standard fingerprint was all over 0.9. A total of 12 common substance peaks were identified, of which the triterpenoids with anti-L1210 tumor cell activity included ganoderic acid C2, ganoderic acid G, ganoderenic acid B, ganoderenic acid A, ganoderic acid K, ganoderic acid A, ganoderic acid F and ganoderal A.
引文
Anon.,2000.Pharmacopoeia of the People’s Republic of China.Chemical Industry Press,Beijing.147(in Chinese)
Boh B,Berovic M,Zhang J,Lin ZB,2007.Ganoderma lucidum and its pharmaceutically active compounds.Biotechnology Annual Review,13(7):265-301
Cao Y,Wu SH,Dai YC,2012.Species clarification of the prize medicinal Ganoderma mushroom“Lingzhi”.Fungal Diversity,56(1):49-62
Da J,Cheng CR,Yao S,Long HL,Wang YH,2015.Areproducible analytical system based on the multi-component analysis of triterpene acids in Ganoderma lucidum.Phytochemistry,6(114):146-154
Dai YC,Cao Y,Zhou LW,Wu SH,2013.Notes on the nomenclature of the most widely cultivated Ganoderma species in China.Mycosystema,32(6):947-952(in Chinese)
Dai YC,Yang ZL,2008.Revision of Chinese medicinal fungi list and some names.Mycosystema,27(6):801-824(in Chinese)
Dao LL,Ying JL,Dong HY,2015.Ganoderma lucidum derived ganoderenic acid B reverses ABCB1-mediated multidrug resistance in HepG2/ADM cells.International Journal of Oncology,46(5):2029-2038
Fatmawati S,Shimizu K,Kondo R,2010.Inhibition of aldose reductase in vitro by constituents of Ganoderma lucidum.Planta Medica,76(15):1691-1693
Feng N,Zhang JS,Tang QJ,Hao RX,Liu YF,Yang Y,Jia W,Zhou S,Tang CH,Zhong JJ,2010.Steroids from fruiting bodies of Coprinus comatus and their inhibition to tumor cell proliferation.Mycosystema,29(2):249-253(in Chinese)
Guo XY,Shen X,Long J,Han J,Che QM,2013.Structural identification of the metabolites of ganoderic acid Bfrom Ganoderma lucidum in rats based on liquid chromatography coupled with electrospray ionization hybrid ion trap and time-of-flight mass spectrometry.Biomedical chromatography:BMC,27(9):1177-1187
Hao YY,2016.Antitumor activity of G 3+CD8+T cells induced by SEA dependent ganoderic acid.Chinese Journal of Prescription Drugs,14(11):16-17(in Chinese)
Jia HY,Wang YT,Zhang ZH,Feng N,Liu YF,Zhou S,Zhang Z,Zhang JS,Tang QJ,2017.Determination of triterpenoids in Ganoderma lucidum from different habitats and varieties by HPLC.Acta Microbiologica Sinica,44(1):238-244(in Chinese)
Jiang J,Grieb B,Thyagarajan A,2008.Ganoderic acids suppress growth and invasive behavior of breast cancer cells by modulating AP-1 and NF-κB signaling.International Journal of Molecular Medicine,21(5):577-584
Kim SD,2010.Isolation and structure determination of a cholesterol esterase inhibitor from Ganoderma lucidum.Journal of Microbiology and Biotechnology,20(11):1521-1523
Lin ZB,Zhang HN,2004.Antitumor and immunoregulatory activities of Ganoderma lucidum and its possible mechanisms.Acta Pharmacologica Sinica,25(11):1387-1395
Liu DL,Li YJ,Yang DH,Wang CR,Xu J,Yao N,Zhang XQ,Chen ZS,Ye WC,Zhang DM,2015.Ganoderma lucidum derived ganoderenic acid b reverses abcb1-mediated multidrug resistance in hepg2/adm cells.International Journal of Oncology,46(5):2029-2038
Liu GQ,Zhang KC,2005.Mechanisms of the anticancer action of Ganoderma lucidum(Leyss.ex Fr.)Karst:a new understanding.Journal of Integrative Plant Biology,47(2):129-135
Ma BJ,Zhou Y,Ruan Y,Ma JC,Ren W,Wen CN,2012.Lanostane-type triterpenes from the sporoderm-broken spores of Ganoderma lucidum.Journal of Antibiotics,65(1):165-167
Qing X,Hua ZZ,Xue FS,Hai JZ,Ling FW,Dan Z,Guan GY,Yan YS,Xiao XZ,Xin M,Lan ZZ,Gai MS,2014.Acomprehensive review of the structure elucidation and biological activity of triterpenoids from Ganoderma spp.Molecules,19(11):17478-17535
State DA,2000.Technical requirements for fingerprint analysis of TCM injection(tentative).Chinese Traditional Patent Medicine,22(10):671-675(in Chinese)
Tang CH,Su CL,Zhang JS,Yang Y,Tang QJ,Jia W,Feng N,Liu YF,Wu D,2012.Analysis of the genetic relationship of Ganoderma strain based on partial sequence of rDNA ITSand beta-tubulin gene.Acta Edulis Fungi,19(3):37-41(in Chinese)
Temitope OL,Sheila MW,Gail BM,2006.Ganoderma lucidum(Ling-zhi):the impact of chemistry on biological activity in cancer.Current Bioactive Compounds,13(1):28-40
Wei MR,David G,Popovich,2012.Ganoderma lucidum triterpenoid extract induces apoptosis in human colon carcinoma cells(Caco-2).Biomedicine and Preventive Nutrition,2(3):203-209
Zhang Y,2017.Ganoderma lucidum(Reishi)suppresses proliferation and migration of breast cancer cells via inhibiting Wnt/β-catenin signaling.Biochemical and Biophysical Research Communications,488(4):679-684
Zhao J,Zhang XQ,Li SP,Yang FQ,Wang YT,Ye W,2006.Quality evaluation of Ganoderma through simultaneous determination of nine triterpenes and sterols using pressurized liquid extraction and high-performance liquid chromatography.Journal of Separation Science,29(17):9-15
Zhou LW,Cao Y,Wu SH,Vlasák J,Li DW,Li MJ,Dai YC,2015.Global diversity of the Ganoderma lucidum complex(Ganodermataceae,Polyporales)inferred from morphology and multilocus phylogeny.Phytochemistry,114:7-15
Zhu X,2015.The role of 14-3-3 proteins in gynecological tumors.Frontiers in Bioscience,20(6):934-945
戴玉成,曹云,周丽伟,吴声华,2013.中国灵芝学名之管见.菌物学报,32(6):947-952
戴玉成,杨祝良,2008.中国药用真菌名录及部分名称的修订.菌物学报,27(6):801-824
冯娜,张劲松,唐庆九,郝瑞霞,刘艳芳,杨焱,贾薇,周帅,唐传红,钟建江,2010.毛头鬼伞子实体中甾类化合物的结构鉴定及其抑制肿瘤细胞增殖活性的研究.菌物学报,29(2):249-253
国家药典委员会,2000,中华人民共和国药典一部.北京:化学工业出版社.147
国家药品监督管理局,2000.中药注射剂指纹图谱研究的技术要求(暂行).中成药,22(10):671-675
郝跃跃,2016.SEA依赖的灵芝酸G诱导Vβ3+CD8+T细胞抗肿瘤活性的研究.中国处方药,14(11):16-17
贾红岩,王亚涛,张芝华,冯娜,刘艳芳,周帅,张忠,张劲松,唐庆九,2017.高效液相色谱法测定不同产地及品种灵芝三萜类成分的含量.微生物学通报,44(1):238-244
唐传红,苏春丽,张劲松,杨焱,唐庆九,贾薇,冯娜,刘艳芳,吴迪,2012.基于rDNA ITS和beta-tubulin gene部分序列分析灵芝属菌株的遗传关系.食用菌学报,19(3):37-41
Boh B,Berovic M,Zhang J,Lin ZB,2007.Ganoderma lucidum and its pharmaceutically active compounds.Biotechnology Annual Review,13(7):265-301
Cao Y,Wu SH,Dai YC,2012.Species clarification of the prize medicinal Ganoderma mushroom“Lingzhi”.Fungal Diversity,56(1):49-62
Da J,Cheng CR,Yao S,Long HL,Wang YH,2015.Areproducible analytical system based on the multi-component analysis of triterpene acids in Ganoderma lucidum.Phytochemistry,6(114):146-154
Dai YC,Cao Y,Zhou LW,Wu SH,2013.Notes on the nomenclature of the most widely cultivated Ganoderma species in China.Mycosystema,32(6):947-952(in Chinese)
Dai YC,Yang ZL,2008.Revision of Chinese medicinal fungi list and some names.Mycosystema,27(6):801-824(in Chinese)
Dao LL,Ying JL,Dong HY,2015.Ganoderma lucidum derived ganoderenic acid B reverses ABCB1-mediated multidrug resistance in HepG2/ADM cells.International Journal of Oncology,46(5):2029-2038
Fatmawati S,Shimizu K,Kondo R,2010.Inhibition of aldose reductase in vitro by constituents of Ganoderma lucidum.Planta Medica,76(15):1691-1693
Feng N,Zhang JS,Tang QJ,Hao RX,Liu YF,Yang Y,Jia W,Zhou S,Tang CH,Zhong JJ,2010.Steroids from fruiting bodies of Coprinus comatus and their inhibition to tumor cell proliferation.Mycosystema,29(2):249-253(in Chinese)
Guo XY,Shen X,Long J,Han J,Che QM,2013.Structural identification of the metabolites of ganoderic acid Bfrom Ganoderma lucidum in rats based on liquid chromatography coupled with electrospray ionization hybrid ion trap and time-of-flight mass spectrometry.Biomedical chromatography:BMC,27(9):1177-1187
Hao YY,2016.Antitumor activity of G 3+CD8+T cells induced by SEA dependent ganoderic acid.Chinese Journal of Prescription Drugs,14(11):16-17(in Chinese)
Jia HY,Wang YT,Zhang ZH,Feng N,Liu YF,Zhou S,Zhang Z,Zhang JS,Tang QJ,2017.Determination of triterpenoids in Ganoderma lucidum from different habitats and varieties by HPLC.Acta Microbiologica Sinica,44(1):238-244(in Chinese)
Jiang J,Grieb B,Thyagarajan A,2008.Ganoderic acids suppress growth and invasive behavior of breast cancer cells by modulating AP-1 and NF-κB signaling.International Journal of Molecular Medicine,21(5):577-584
Kim SD,2010.Isolation and structure determination of a cholesterol esterase inhibitor from Ganoderma lucidum.Journal of Microbiology and Biotechnology,20(11):1521-1523
Lin ZB,Zhang HN,2004.Antitumor and immunoregulatory activities of Ganoderma lucidum and its possible mechanisms.Acta Pharmacologica Sinica,25(11):1387-1395
Liu DL,Li YJ,Yang DH,Wang CR,Xu J,Yao N,Zhang XQ,Chen ZS,Ye WC,Zhang DM,2015.Ganoderma lucidum derived ganoderenic acid b reverses abcb1-mediated multidrug resistance in hepg2/adm cells.International Journal of Oncology,46(5):2029-2038
Liu GQ,Zhang KC,2005.Mechanisms of the anticancer action of Ganoderma lucidum(Leyss.ex Fr.)Karst:a new understanding.Journal of Integrative Plant Biology,47(2):129-135
Ma BJ,Zhou Y,Ruan Y,Ma JC,Ren W,Wen CN,2012.Lanostane-type triterpenes from the sporoderm-broken spores of Ganoderma lucidum.Journal of Antibiotics,65(1):165-167
Qing X,Hua ZZ,Xue FS,Hai JZ,Ling FW,Dan Z,Guan GY,Yan YS,Xiao XZ,Xin M,Lan ZZ,Gai MS,2014.Acomprehensive review of the structure elucidation and biological activity of triterpenoids from Ganoderma spp.Molecules,19(11):17478-17535
State DA,2000.Technical requirements for fingerprint analysis of TCM injection(tentative).Chinese Traditional Patent Medicine,22(10):671-675(in Chinese)
Tang CH,Su CL,Zhang JS,Yang Y,Tang QJ,Jia W,Feng N,Liu YF,Wu D,2012.Analysis of the genetic relationship of Ganoderma strain based on partial sequence of rDNA ITSand beta-tubulin gene.Acta Edulis Fungi,19(3):37-41(in Chinese)
Temitope OL,Sheila MW,Gail BM,2006.Ganoderma lucidum(Ling-zhi):the impact of chemistry on biological activity in cancer.Current Bioactive Compounds,13(1):28-40
Wei MR,David G,Popovich,2012.Ganoderma lucidum triterpenoid extract induces apoptosis in human colon carcinoma cells(Caco-2).Biomedicine and Preventive Nutrition,2(3):203-209
Zhang Y,2017.Ganoderma lucidum(Reishi)suppresses proliferation and migration of breast cancer cells via inhibiting Wnt/β-catenin signaling.Biochemical and Biophysical Research Communications,488(4):679-684
Zhao J,Zhang XQ,Li SP,Yang FQ,Wang YT,Ye W,2006.Quality evaluation of Ganoderma through simultaneous determination of nine triterpenes and sterols using pressurized liquid extraction and high-performance liquid chromatography.Journal of Separation Science,29(17):9-15
Zhou LW,Cao Y,Wu SH,Vlasák J,Li DW,Li MJ,Dai YC,2015.Global diversity of the Ganoderma lucidum complex(Ganodermataceae,Polyporales)inferred from morphology and multilocus phylogeny.Phytochemistry,114:7-15
Zhu X,2015.The role of 14-3-3 proteins in gynecological tumors.Frontiers in Bioscience,20(6):934-945
戴玉成,曹云,周丽伟,吴声华,2013.中国灵芝学名之管见.菌物学报,32(6):947-952
戴玉成,杨祝良,2008.中国药用真菌名录及部分名称的修订.菌物学报,27(6):801-824
冯娜,张劲松,唐庆九,郝瑞霞,刘艳芳,杨焱,贾薇,周帅,唐传红,钟建江,2010.毛头鬼伞子实体中甾类化合物的结构鉴定及其抑制肿瘤细胞增殖活性的研究.菌物学报,29(2):249-253
国家药典委员会,2000,中华人民共和国药典一部.北京:化学工业出版社.147
国家药品监督管理局,2000.中药注射剂指纹图谱研究的技术要求(暂行).中成药,22(10):671-675
郝跃跃,2016.SEA依赖的灵芝酸G诱导Vβ3+CD8+T细胞抗肿瘤活性的研究.中国处方药,14(11):16-17
贾红岩,王亚涛,张芝华,冯娜,刘艳芳,周帅,张忠,张劲松,唐庆九,2017.高效液相色谱法测定不同产地及品种灵芝三萜类成分的含量.微生物学通报,44(1):238-244
唐传红,苏春丽,张劲松,杨焱,唐庆九,贾薇,冯娜,刘艳芳,吴迪,2012.基于rDNA ITS和beta-tubulin gene部分序列分析灵芝属菌株的遗传关系.食用菌学报,19(3):37-41