新古尼异虫草石油醚提取物的成分分析
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摘要
【背景】新古尼异虫草具有多种药理作用,是一种具有开发潜力的新资源。但该虫草仍有很多活性物质值得探寻,目前对该虫草活性物质的研究多集中于大分子或极性物质,对小分子或弱极性物质的研究关注甚少。【目的】研究新古尼异虫草石油醚提取物中非极性/弱极性小分子化合物,以期完善该虫草中活性物质的化学指纹图谱库。【方法】利用石油醚对新古尼异虫草进行索氏提取,借助傅里叶变换红外光谱(Fourier transform infrared spectroscopy,FTIR)和气相色谱-质谱(GC-MS)联用技术鉴定分析石油醚萃取物中的物质组成。【结果】FTIR表明该虫草石油醚萃取物中含有C-H、C=O、C-O和C=C等官能团,经GC-MS进一步分析鉴定出109种化合物,主要包括烷烃、芳烃、烯烃、酸、酯、醇、胺等化合物,且首次检出甾类、芳烃类、烷烃类、酰胺类、烯烃类和酚类非极性/弱极性的小分子化合物,其中亚油酸及其同分异构体的相对含量最高(38.33%)。【结论】从新古尼异虫草中提取得到多种小分子活性成分,补充了该虫草中的物质组成,为其高附加值利用提供数据支撑。
[Background] Metacordyceps neogunnii was a kind of new resource with the potential application value because it possessed multiple pharmacological functions. However, more active compounds were still worthy of exploring. The research of its active compounds mainly focused on macromolecular or polar compounds up to date, few studies were paid to micromolecular or weak-polar compounds. [Objective] The non-polar or weak-polar small molecular compounds of the petroleum ether extracts from M. neogunnii were researched in this study, in order to improve the chemical fingerprint database of the active substances in the M. neogunnii. [Methods] M. neogunnii were extracted with petroleum ether by soxhlet extraction. The substance components were identified and analyzed by fourier transform infrared spectrometry(FTIR) and gas chromatography-mass spectrometry(GC-MS). [Results]According to FTIR, the analyses found that the components of extracts included the functional groups such as C-H, C=O, C-O and C=C; Through GC-MS method, 109 compounds including alkanes, arenes,olefins, acids, esters, alcohols, amines and others were identified. The non-polar or weak-polar small molecular compounds such as steroids, aromatics, alkanes, amides, olefins and phenols were discovered for the first time; And the relative contents of linoleic acid and its isomer were the highest, up to 38.33%.[Conclusion] Many small active components from M. neogunnii were obtained by petroleum ether extraction, which supplemented the chemical composition and provided scientific data for high value-added utilization of M. neogunnii.
[Background] Metacordyceps neogunnii was a kind of new resource with the potential application value because it possessed multiple pharmacological functions. However, more active compounds were still worthy of exploring. The research of its active compounds mainly focused on macromolecular or polar compounds up to date, few studies were paid to micromolecular or weak-polar compounds. [Objective] The non-polar or weak-polar small molecular compounds of the petroleum ether extracts from M. neogunnii were researched in this study, in order to improve the chemical fingerprint database of the active substances in the M. neogunnii. [Methods] M. neogunnii were extracted with petroleum ether by soxhlet extraction. The substance components were identified and analyzed by fourier transform infrared spectrometry(FTIR) and gas chromatography-mass spectrometry(GC-MS). [Results]According to FTIR, the analyses found that the components of extracts included the functional groups such as C-H, C=O, C-O and C=C; Through GC-MS method, 109 compounds including alkanes, arenes,olefins, acids, esters, alcohols, amines and others were identified. The non-polar or weak-polar small molecular compounds such as steroids, aromatics, alkanes, amides, olefins and phenols were discovered for the first time; And the relative contents of linoleic acid and its isomer were the highest, up to 38.33%.[Conclusion] Many small active components from M. neogunnii were obtained by petroleum ether extraction, which supplemented the chemical composition and provided scientific data for high value-added utilization of M. neogunnii.
引文
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[12]Zhu ZY,Liang ZQ,Chang SJ,et al.Bioactive substances from Cordyceps gunnii I.separation,purification and properties of analgesic substance[J].Acta Microbiologica Sinica,2002,42(6):732-736(in Chinese)朱振元,梁宗琦,常胜军,等.古尼虫草的生物活性物质I.含肽镇痛组分的分离及性质[J].微生物学报,2002,42(6):732-736
[13]Lei BX,Gao HB,Shui XB,et al.Determination of mannitol in fermented mycelia of Cordyceps gummii[J].Journal of Fungal Research,2004,2(1):40-44(in Chinese)雷帮星,高海波,税小波,等.人工发酵古尼虫草中甘露醇的测定[J].菌物研究,2004,2(l):40-44
[14]Zhang YM,Zhang Q,Yang Q,et al.Comparison of modern and traditional extraction methods for flavonoids from Cordyceps gunnii[J].Food Research and Development,2007,28(1):136-140(in Chinese)张永明,张倩,杨青,等.现代技术与传统方法萃取古尼虫草总黄酮的比较[J].食品研究与开发,2007,28(1):136-140
[15]Dong HR.Instrumental Analysis[M].Beijing:Chemical Industry Press,2000:177-185(in Chinese)董慧茹.仪器分析[M].北京:化学工业出版社,2000:177-185
[16]Liu ZG.Instrumental Analysis[M].Beijing:Higher Education Press,2007:287-289(in Chinese)刘志广.仪器分析[M].北京:高等教育出版社,2007:287-289
[17]Hu FL,Li ZZ.Secondary metabolites and their bioactivities of Cordyceps and its related fungi[J].Mycosystema,2007,26(4):607-632(in Chinese)胡丰林,李增智.虫草及相关真菌的次生代谢产物及其活性[J].菌物学报,2007,26(4):607-632
[18]Warui DM,Li N,N?rgaard H,et al.Detection of formate,rather than carbon monoxide,as the stoichiometric coproduct in conversion of fatty aldehydes to alkanes by a cyanobacterial aldehyde decarbonylase[J].Journal of the American Chemical Society,2011,133(10):3316-3319
[19]Schirmer A,Rude MA,Li XZ,et al.Microbial biosynthesis of alkanes[J].Science,2010,329(5991):559-562
[20]Zhang HZ,Sheng GY,Wang KF,et al.A preliminary study on biomarker characteristics and thermal simulation experiments of fungi spore-Arternaria[J].Geochimica,1997,26(3):37-44(in Chinese)张惠之,盛国英,王开发,等.真菌孢子烷烃生物标志物特征及其热演化试验的初步研究[J].地球化学,1997,26(3):37-44
[21]Dennis M,Kolattukudy PE.A cobalt-porphyrin enzyme converts a fatty aldehyde to a hydrocarbon and CO[J].Proceedings of the National Academy of Sciences of the United States of America,1992,89(12):5306-5310
[22]Su SJ,Guo HW,Chen HW,et al.Research progress in microbial production of alkanes[J].Industrial Microbiology,2017,47(1):56-64(in Chinese)苏绍洁,郭洪伟,陈宏文,等.微生物法生产烷烃研究进展[J].工业微生物,2017,47(1):56-64
[23]Kalacheva GS,Zhila NO,Volova TG.Lipid and hydrocarbon compositions of a collection strain and a wild sample of the green microalga Botryococcus[J].Aquatic Ecology,2002,36(2):317-331
[24]Bian ZH,Yu RL,Wei SM,et al.Comparative study on the contents of fatty acids in Isaria cicadae,Cordyceps militaris and Cordyceps sinensis[J].China Pharmacy,2017,28(30):4252-4256(in Chinese)卞智慧,于瑞莲,魏思敏,等.蝉花、蛹虫草和冬虫夏草药材中脂肪酸含量的比较研究[J].中国药房,2017,28(30):4252-4256
[25]Wang JY,Zhu SG,Xu CF.Biochemistry.Vol.1[M].2nd ed.Beijing:Higher Education Press,2004:88-89(in Chinese)王镜岩,朱圣庚,徐长法.生物化学·上册[M].2版.北京:高等教育出版社,2004:88-89
[26]Zheng C,Yang M,Zhou Q,et al.Contents of fatty acid and minor component and oxidative stability of high-oleic peanut oil and normal-oleic peanut oil[J].China Oils and Fats,2014,39(11):40-43(in Chinese)郑畅,杨湄,周琦,等.高油酸花生油与普通油酸花生油的脂肪酸、微量成分含量和氧化稳定性[J].中国油脂,2014,39(11):40-43
[27]Zhang Q,Zhao XH.Phytosterols and its anticancer effect[J].China Oils and Fats,2006,31(10):57-60(in Chinese)张强,赵新淮.植物甾醇及其抗癌作用[J].中国油脂,2006,31(10):57-60
[28]Awad AB,Chinnam M,Fink CS,et al.β-Sitosterol activates Fas signaling in human breast cancer cells[J].Phytomedicine,2007,14(11):747-754
[29]Zhou ZY,Lu Q,Liu Y,et al.Research and development progress of stigmasterol[J].China Modern Medicine,2015,22(24):15-17(in Chinese)周志远,卢群,刘洋,等.豆甾醇的研究及开发进展[J].中国当代医药,2015,22(24):15-17
[30]Lee S,Lee YS,Jung SH.Anti-oxidant activities of fucosterol from the marine algae Pelvetia siliquosa[J].Archives of Pharmacal Research,2003,26(9):719-722
[31]Zhang GJ,Yang LL,Yuan C,et al.Research progress on development and application of squalene[J].Cereals&Oils,2017,30(12):7-10(in Chinese)张光杰,杨利玲,袁超,等.角鲨烯开发及应用研究进展[J].粮食与油脂,2017,30(12):7-10
[2]Wen TC,Xiao YP,Han YF,et al.Multigene phylogeny and morphology reveal that the Chinese medicinal mushroom‘Cordyceps gunnii’is Metacordyceps neogunnii sp.nov.[J].Phytotaxa,2017,302(1):27-39
[3]Zhang YM,Zhang Q,Liang ZQ.Research situation and development trends of Cordyceps gunnii[J].Guizhou Agricultural Sciences,2006,34(2):121-123(in Chinese)张永明,张倩,梁宗琦.古尼虫草的研究现状与发展动态[J].贵州农业科学,2006,34(2):121-123
[4]Liang ZQ,Chang SJ,Liu AY.Analgesic substance from the anamorph of Cordyceps gunnii(Berk.)Berk[J].Journal of Huazhong Agricultural,2004,23(1):40-43
[5]Xiao JH,Fang N,Xiao Y,et al.Immunosuppressive activity of exopolysaccharide from Paecilomyces gunnii[J].Journal of Chinese Medicinal Materials,2004,27(3):192-195(in Chinese)肖建辉,方宁,肖瑜,等.古尼拟青霉胞外多糖的免疫抑制活性[J].中药材,2004,27(3):192-195
[6]Meng XX,Zhang ZG,Chen ZH.Protection of the Cordyceps Gunniit to antiultraviolet radiation in Bacilius thuringiensis[J].Journal of Natural Science of Hunan Normal University,2001,24(1):66-68(in Chinese)孟祥贤,张志光,陈作红.古尼虫草对苏云金杆菌抗紫外辐射的保护作用[J].湖南师范大学:自然科学学报,2001,24(1):66-68
[7]Li SF,Bao SJ,Sun GC.Experimental study on antiaging effect of Penicillium guricillium[J].Guizhou Medical Journal,1996,20(1):25-26(in Chinese)李淑芳,鲍淑娟,孙光春.古尼拟青霉抗衰老作用的实验研究[J].贵州医药,1996,20(1):25-26
[8]Zhang Q,Zhang YM,Lu WQ,et al.Study of polysacchrides of Cordyceps Gunnii Berks on learning and memory ability of mice[J].Acta Nutrimenta Sinica,2007,29(4):393-395,400(in Chinese)张倩,张永明,陆卫群,等.古尼虫草多糖改善小鼠学习记忆作用的研究[J].营养学报,2007,29(4):393-395,400
[9]Xiong ZM,Li SF,Bao SJ,et al.Protective effects of paecilomyces gunnii on acute cerebral ischemia injury in rats and its mechanisms[J].Chinese Pharmaceutical Journal,2001,36(4):248-251(in Chinese)熊正梅,李淑芳,鲍淑娟,等.古尼拟青霉对大鼠急性缺血性脑损伤的保护作用及机制研究[J].中国药学杂志,2001,36(4):248-251
[10]Chen ZH,Tian XR,Meng XX,et al.Determination of nucleosides in Cordyceps gunnii by HPLC[J].Mycosystema,2003,22(3):489-493(in Chinese)陈作红,田向荣,孟祥贤,等.古尼虫草核苷类成分的高效液相色谱分析[J].菌物系统,2003,22(3):489-493
[11]Zhu ZY,Dong HY,Wang TY.Degradation of Cordyceps gunnii polysaccharide and antioxidation of its degraded products[J].Food Research and Development,2017,38(10):1-5(in Chinese)朱振元,董海燕,王腾月.古尼虫草菌丝体多糖降解及体外抗氧化活性研究[J].食品研究与开发,2017,38(10):1-5
[12]Zhu ZY,Liang ZQ,Chang SJ,et al.Bioactive substances from Cordyceps gunnii I.separation,purification and properties of analgesic substance[J].Acta Microbiologica Sinica,2002,42(6):732-736(in Chinese)朱振元,梁宗琦,常胜军,等.古尼虫草的生物活性物质I.含肽镇痛组分的分离及性质[J].微生物学报,2002,42(6):732-736
[13]Lei BX,Gao HB,Shui XB,et al.Determination of mannitol in fermented mycelia of Cordyceps gummii[J].Journal of Fungal Research,2004,2(1):40-44(in Chinese)雷帮星,高海波,税小波,等.人工发酵古尼虫草中甘露醇的测定[J].菌物研究,2004,2(l):40-44
[14]Zhang YM,Zhang Q,Yang Q,et al.Comparison of modern and traditional extraction methods for flavonoids from Cordyceps gunnii[J].Food Research and Development,2007,28(1):136-140(in Chinese)张永明,张倩,杨青,等.现代技术与传统方法萃取古尼虫草总黄酮的比较[J].食品研究与开发,2007,28(1):136-140
[15]Dong HR.Instrumental Analysis[M].Beijing:Chemical Industry Press,2000:177-185(in Chinese)董慧茹.仪器分析[M].北京:化学工业出版社,2000:177-185
[16]Liu ZG.Instrumental Analysis[M].Beijing:Higher Education Press,2007:287-289(in Chinese)刘志广.仪器分析[M].北京:高等教育出版社,2007:287-289
[17]Hu FL,Li ZZ.Secondary metabolites and their bioactivities of Cordyceps and its related fungi[J].Mycosystema,2007,26(4):607-632(in Chinese)胡丰林,李增智.虫草及相关真菌的次生代谢产物及其活性[J].菌物学报,2007,26(4):607-632
[18]Warui DM,Li N,N?rgaard H,et al.Detection of formate,rather than carbon monoxide,as the stoichiometric coproduct in conversion of fatty aldehydes to alkanes by a cyanobacterial aldehyde decarbonylase[J].Journal of the American Chemical Society,2011,133(10):3316-3319
[19]Schirmer A,Rude MA,Li XZ,et al.Microbial biosynthesis of alkanes[J].Science,2010,329(5991):559-562
[20]Zhang HZ,Sheng GY,Wang KF,et al.A preliminary study on biomarker characteristics and thermal simulation experiments of fungi spore-Arternaria[J].Geochimica,1997,26(3):37-44(in Chinese)张惠之,盛国英,王开发,等.真菌孢子烷烃生物标志物特征及其热演化试验的初步研究[J].地球化学,1997,26(3):37-44
[21]Dennis M,Kolattukudy PE.A cobalt-porphyrin enzyme converts a fatty aldehyde to a hydrocarbon and CO[J].Proceedings of the National Academy of Sciences of the United States of America,1992,89(12):5306-5310
[22]Su SJ,Guo HW,Chen HW,et al.Research progress in microbial production of alkanes[J].Industrial Microbiology,2017,47(1):56-64(in Chinese)苏绍洁,郭洪伟,陈宏文,等.微生物法生产烷烃研究进展[J].工业微生物,2017,47(1):56-64
[23]Kalacheva GS,Zhila NO,Volova TG.Lipid and hydrocarbon compositions of a collection strain and a wild sample of the green microalga Botryococcus[J].Aquatic Ecology,2002,36(2):317-331
[24]Bian ZH,Yu RL,Wei SM,et al.Comparative study on the contents of fatty acids in Isaria cicadae,Cordyceps militaris and Cordyceps sinensis[J].China Pharmacy,2017,28(30):4252-4256(in Chinese)卞智慧,于瑞莲,魏思敏,等.蝉花、蛹虫草和冬虫夏草药材中脂肪酸含量的比较研究[J].中国药房,2017,28(30):4252-4256
[25]Wang JY,Zhu SG,Xu CF.Biochemistry.Vol.1[M].2nd ed.Beijing:Higher Education Press,2004:88-89(in Chinese)王镜岩,朱圣庚,徐长法.生物化学·上册[M].2版.北京:高等教育出版社,2004:88-89
[26]Zheng C,Yang M,Zhou Q,et al.Contents of fatty acid and minor component and oxidative stability of high-oleic peanut oil and normal-oleic peanut oil[J].China Oils and Fats,2014,39(11):40-43(in Chinese)郑畅,杨湄,周琦,等.高油酸花生油与普通油酸花生油的脂肪酸、微量成分含量和氧化稳定性[J].中国油脂,2014,39(11):40-43
[27]Zhang Q,Zhao XH.Phytosterols and its anticancer effect[J].China Oils and Fats,2006,31(10):57-60(in Chinese)张强,赵新淮.植物甾醇及其抗癌作用[J].中国油脂,2006,31(10):57-60
[28]Awad AB,Chinnam M,Fink CS,et al.β-Sitosterol activates Fas signaling in human breast cancer cells[J].Phytomedicine,2007,14(11):747-754
[29]Zhou ZY,Lu Q,Liu Y,et al.Research and development progress of stigmasterol[J].China Modern Medicine,2015,22(24):15-17(in Chinese)周志远,卢群,刘洋,等.豆甾醇的研究及开发进展[J].中国当代医药,2015,22(24):15-17
[30]Lee S,Lee YS,Jung SH.Anti-oxidant activities of fucosterol from the marine algae Pelvetia siliquosa[J].Archives of Pharmacal Research,2003,26(9):719-722
[31]Zhang GJ,Yang LL,Yuan C,et al.Research progress on development and application of squalene[J].Cereals&Oils,2017,30(12):7-10(in Chinese)张光杰,杨利玲,袁超,等.角鲨烯开发及应用研究进展[J].粮食与油脂,2017,30(12):7-10