人参真菌菌质的乙酸乙酯部位化学成分研究
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摘要
目的:对生物转化得到的人参真菌菌质的乙酸乙酯部位化学成分进行研究,以期获得活性更好、毒性更低的化合物,为新药研发及人参药材的二次开发利用提供参考。方法:将代号为C-1的真菌种子液加至含有人参的培养基中,生物转化得到人参真菌菌质;称取干燥人参真菌菌质,以70%乙醇溶剂提取浓缩制得稠膏;稠膏加入水混悬,采用乙酸乙酯萃取,获得乙酸乙酯部位。采用薄层色谱、硅胶柱色谱、ODS柱色谱以及半制备液相对上述乙酸乙酯部位进行分离纯化,根据理化性质以及氢谱(~1H-NMR)和碳谱(~(13)C-NMR)数据鉴定化合物结构。结果:从人参真菌菌质的乙酸乙酯部位分离、鉴定得到8个化合物,分别为人参皂苷Rs_7(1)、人参皂苷Rk_3(2)、齐墩果酸-28-O-β-D-吡喃葡萄糖苷(3)、人参皂苷Rs_6(4)、20(R)-人参皂苷Rh_1(5)、人参皂苷F_1(6)、三七皂苷R_2(7)、人参皂苷F_4(8)。结论:上述化合物均在人参真菌菌质中发现,其中化合物3、5、6、7、8为经生物转化后得到的,证明生物转化技术能改变人参的化学成分。
OBJECTIVE:To study the chemical constituents of ethyl acetate fraction of Panax ginseng fungal substance obtained by biotransformation,in order to obtain compounds with better activity and lower toxicity,and to provide reference for new drug R&D and the second development and utilization of P. ginseng. METHODS:Fungus of Code Name C-1 seed solution was added into the culture medium containing P. ginseng,and P. ginseng fungal substance was obtained by biotransformation;the dried P. ginseng fungal substance were weighed,extracting with 70% ethanol solvent and concentrating to obtain thick paste. The thick paste was added with water suspension and extracted with ethyl acetate to obtain ethyl acetate fraction. TLC,silica gel column chromatography,ODS column chromatography and semi-prepared liquid phase were used to isolate and purify above ethyl acetate fraction, and the compound structure was identified according to physicochemical properties, hydrogen spectrum(~1H-NMR)and carbon spectrum(~(13)C-NMR)data. RESULTS:Eight compounds were isolated and identified from the ethyl acetate fraction of P. ginseng fungal substance and identified as ginsenoside Rs_7(1), ginsenoside Rk_3(2), oleanolic acid-28-O-β-D-glucopyranoside(3),ginsenoside Rs_6(4),20(R)-ginsenoside Rh_1(5),ginsenoside F_1(6),notoginsenoside R_2(7)and ginsenoside F_4(8). CONCLUSIONS:All the above compounds were found in P. ginseng fungal substance,which compounds 3,5,6,7 and 8 were obtained after biotransformation,proving that biotransformation technology can change the chemical composition of ginseng.
OBJECTIVE:To study the chemical constituents of ethyl acetate fraction of Panax ginseng fungal substance obtained by biotransformation,in order to obtain compounds with better activity and lower toxicity,and to provide reference for new drug R&D and the second development and utilization of P. ginseng. METHODS:Fungus of Code Name C-1 seed solution was added into the culture medium containing P. ginseng,and P. ginseng fungal substance was obtained by biotransformation;the dried P. ginseng fungal substance were weighed,extracting with 70% ethanol solvent and concentrating to obtain thick paste. The thick paste was added with water suspension and extracted with ethyl acetate to obtain ethyl acetate fraction. TLC,silica gel column chromatography,ODS column chromatography and semi-prepared liquid phase were used to isolate and purify above ethyl acetate fraction, and the compound structure was identified according to physicochemical properties, hydrogen spectrum(~1H-NMR)and carbon spectrum(~(13)C-NMR)data. RESULTS:Eight compounds were isolated and identified from the ethyl acetate fraction of P. ginseng fungal substance and identified as ginsenoside Rs_7(1), ginsenoside Rk_3(2), oleanolic acid-28-O-β-D-glucopyranoside(3),ginsenoside Rs_6(4),20(R)-ginsenoside Rh_1(5),ginsenoside F_1(6),notoginsenoside R_2(7)and ginsenoside F_4(8). CONCLUSIONS:All the above compounds were found in P. ginseng fungal substance,which compounds 3,5,6,7 and 8 were obtained after biotransformation,proving that biotransformation technology can change the chemical composition of ginseng.
引文
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[15]王红燕,裴玉萍,陈英杰.人参花蕾化学成分研究[J].中国药物化学杂志,1992,2(2):31-35.
[16]TEN LN,CHAE SM,YOO SA.Biotransformation of ginsenosides Re and Rg1by the bacterium microbacterium sp.GT35[J].Chemistry of Natural Compounds,2015,51(1):81-86.
[17]马丽媛,杨秀伟.人参茎叶总皂苷碱水解产物中的新人参皂苷20(R)-人参皂苷Rh19[J].中草药,2016,47(1):6-14.
[18]郭娜,付锐,窦德强.加拿大产西洋参的化学成分研究[J].中国药物化学杂志,2006,16(3):172-175.
[19]TENG RW,LI HZ,CHEN JT,et al.Complete assignment of1H and13C NMR data for nine protopanaxatriol glycosides[J].Magn Reson Chem,2002,40(7):483-488.
[20]李国红,沈月毛,王启方,等.发酵三七中的皂苷成分研究[J].中草药,2005,36(4):499-500.
[21]RYU JH,PARK JH,EUN JH,et al.A dammarane glycoside from Korean red ginseng[J].Phytochemistry,1997,44(5):931-933.
[22]ZHANG SL,TAKEDA T,ZHU T,et al.A new minor saponin from the leaves of panax ginseng[J].Planta Med,1990,56(3):298-300.
[23]张彩,史磊.人参化学成分和药理作用研究进展[J].食品与药品,2016,18(4):300-304.
[24]曾露露,丁传波,刘文丛,等.人参稀有皂苷药理活性的研究进展[J].时珍国医国药,2018,29(3):680-682.
[25]方进波,刘焱文,张彦文,等.空心莲子草抗病毒活性成分研究[J].中草药,2007,38(7):976-979.
[26]张福康,陆再华,杨妍华.三七总皂苷对细胞免疫炎症因子作用的研究进展[J].中国药师,2011,14(9):1349-1350.
[27]吕青远.三七叶苷的化学成分及药理作用[J].时珍国医国药,2006,17(10):2065-2066.
[2]刚婉娇,王明蛟,关升远,等.人参药性菌质乙酸乙酯部位化学成分[J].中国实验方剂学杂志,2014,20(17):114-116.
[3]张春枝,安利佳,金凤燮.人参皂苷生理活性的研究进展[J].食品与发酵工业,2002,28(4):70-74.
[4]于荣敏.天然药物活性成分的生物合成与生物转化[J].中草药,2006,37(9):1281-1288.
[5]丁彩凤,王明蛟,邱智东,等.三七药性菌质乙酸乙酯部分化学成分[J].中国实验方剂学杂志,2015,21(7):43-46.
[6]XU W,DING CF,WANG XW,et al.Two new triterpenoid saponins from notoginseng medicinal fungal substance[J].Chinese Chem Lett,2015.DOI:10.1016/j.cclet.2015.07.014.
[7]XU W,DING CF,LIU XL,et al.Chemical constituents of the notoginseng medicinal fungal substance[J].Chemistry of Natural Compounds,2017,53(3):483-485.
[8]朱凯,贾艾玲,徐瑶,等.人参药性菌质对小鼠Lewis肺癌的作用[J].中国老年学杂志,2013,33(23):5882-5883.
[9]朱莹莹,刘鑫,贾艾玲,等.HPLC同时测定人参药性菌质中8种皂苷含量[J].中国实验方剂学杂志,2016,22(7):96-99.
[10]贾继明,王宗权.西洋参总皂苷乙酸水解产物的化学成分研究:Ⅰ[J].中草药,2009,40(8):1204-1207.
[11]潘小玲,李振麟,钱士辉,等.中国人参花化学成分研究[J].中国野生植物资源,2014,33(2):13-15.
[12]徐金中,王贤亲,黄可新,等.中华雪胆中的三萜皂苷类化学成分研究[J].中国药学杂志,2008,43(23):1770-1773.
[13]NIE RL,MORITA T,KASAI R,et al.Saponins from Chinese medicinal plants(Ⅰ)isolation and structures of hemslosides[J].Planta Med,1984,50(4):322-327.
[14]PARK IH,HAN SB,KIM JM,et al.Four new acetylated ginsenosides from processed ginseng(sun ginseng)[J].Arch Pharm Res,2002,25(6):837-841.
[15]王红燕,裴玉萍,陈英杰.人参花蕾化学成分研究[J].中国药物化学杂志,1992,2(2):31-35.
[16]TEN LN,CHAE SM,YOO SA.Biotransformation of ginsenosides Re and Rg1by the bacterium microbacterium sp.GT35[J].Chemistry of Natural Compounds,2015,51(1):81-86.
[17]马丽媛,杨秀伟.人参茎叶总皂苷碱水解产物中的新人参皂苷20(R)-人参皂苷Rh19[J].中草药,2016,47(1):6-14.
[18]郭娜,付锐,窦德强.加拿大产西洋参的化学成分研究[J].中国药物化学杂志,2006,16(3):172-175.
[19]TENG RW,LI HZ,CHEN JT,et al.Complete assignment of1H and13C NMR data for nine protopanaxatriol glycosides[J].Magn Reson Chem,2002,40(7):483-488.
[20]李国红,沈月毛,王启方,等.发酵三七中的皂苷成分研究[J].中草药,2005,36(4):499-500.
[21]RYU JH,PARK JH,EUN JH,et al.A dammarane glycoside from Korean red ginseng[J].Phytochemistry,1997,44(5):931-933.
[22]ZHANG SL,TAKEDA T,ZHU T,et al.A new minor saponin from the leaves of panax ginseng[J].Planta Med,1990,56(3):298-300.
[23]张彩,史磊.人参化学成分和药理作用研究进展[J].食品与药品,2016,18(4):300-304.
[24]曾露露,丁传波,刘文丛,等.人参稀有皂苷药理活性的研究进展[J].时珍国医国药,2018,29(3):680-682.
[25]方进波,刘焱文,张彦文,等.空心莲子草抗病毒活性成分研究[J].中草药,2007,38(7):976-979.
[26]张福康,陆再华,杨妍华.三七总皂苷对细胞免疫炎症因子作用的研究进展[J].中国药师,2011,14(9):1349-1350.
[27]吕青远.三七叶苷的化学成分及药理作用[J].时珍国医国药,2006,17(10):2065-2066.
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