人参花蕾的皂苷类化学成分研究
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摘要
对人参花蕾中的人参皂苷类化学成分进行研究。通过大孔吸附树脂Diaion HP-20,反复硅胶柱色谱,MCI gel柱色谱及半制备高效液相色谱等方法对其提取物进行分离和纯化,利用NMR,MS等波谱学技术对分离得到的化合物进行结构鉴定。从人参花蕾醇提物的水萃取部位中分离得到了32个化合物,分别鉴定为人参皂苷Rk_3(1)、人参皂苷Rh_4(2)、人参皂苷Rh_8(3)、假人参皂苷Rc_1(4)、人参皂苷Rc(5)、人参皂苷Rb_2(6)、人参皂苷Rg_6(7)、20(E)-人参皂苷F_4(8)、人参皂苷Rb_1(9)、越南人参皂苷R_(16)(10)、人参皂苷Rh_6(11)、越南人参皂苷R_3(12)、5,6-二脱氢人参皂苷Rd(13)、越南人参皂苷R_4(14)、越南人参皂苷R_8(15)、人参皂苷Rf(16)、三七皂苷E(17)、人参皂苷Ⅲ(18)、3-O-β-D-吡喃葡萄糖基-3β,7β,12β,20S-四羟基-达玛-5(6),24-二烯-20-O-β-D-吡喃葡萄糖苷(19)、20(S)-人参皂苷Rg2(20)、20(R)-人参皂苷Rg_2(21)、三七皂苷R_2(22)、人参皂苷F_2(23)、西洋参皂苷Ⅰ(24)、人参皂苷M_1(25)、西洋参皂苷L_(10)(26)、人参皂苷Rh_5(27)、人参皂苷Rg_5(28)、人参皂苷Rk_1(29)、20(R)-人参皂苷Rg_3(30)、齐墩果酸-3-O-β-D-吡喃葡萄糖基-(1→2)-β-D-(6'-甲酯)-吡喃葡萄糖醛酸苷(31)和人参皂苷MC(32)。化合物10,12,13,15,19,22,24,31及32为首次从人参中分离得到,其中化合物19为首次通过分离鉴定得到的实体化合物,并报道了其NMR数据;化合物1～3,7,8,23,25～30为首次从人参花蕾中分离得到。
This project is to investigate the chemical constituents of ginsenosides from the flower buds of Panax ginseng. The compounds were isolated by using a variety of chromatographic methods including Diaion HP-20,silica gel,MCI gel and semi-preparative HPLC chromatography. Their structures were identified by NMR,and MS data. As a result,32 compounds were isolated from the extract of P. ginseng flower buds,and identified as ginsenoside Rk_3( 1),ginsenoside Rh_4( 2),ginsenoside Rh_8( 3),pseudoginsenoside Rc_1( 4),ginsenoside Rc( 5),ginsenoside Rb_2( 6),ginsenoside Rg_6( 7),20( E)-ginsenoside F_4( 8),ginsenoside Rb_1( 9),vinaginsenoside R_(16)( 10),ginsenoside Rh_6( 11),vinaginsenoside R_3( 12),5,6-didehydro-ginsenoside Rd( 13),vinaginsenoside R_4( 14),vinaginsenoside R_8( 15),ginsenoside Rf( 16),notoginsenoside E( 17),ginsenoside Ⅲ( 18),3-O-β-D-glucopyranosyl-3β,7β,12β,20 S-tetrahydroxydammar-5( 6),24-diene-20-O-β-D-glucopyranoside( 19),20( S)-ginsenoside Rg_2( 20),20( R)-ginsenoside Rg_2( 21),notoginsenoside R_2( 22),ginsenoside F_2( 23),quinquenoside I( 24),ginsenoside M_1( 25),quinquenoside L_(10)( 26),ginsenoside Rh_5( 27),ginsenoside Rg_5( 28),ginsenoside Rk_1( 29),20( R)-ginsenoside Rg_3( 30),oleanolic acid 3-O-β-D-glucopyranosyl-( 1→2)-β-D-( 6'-methyl ester)-glucuronopyranoside( 31) and ginsenoside MC( 32). Among them,compounds 10,12,13,15,19,22,24,31 and 32 were isolated from P. ginseng for the first time,and compound 19 was a genuine ginsenoside firstly obtained by separation and identification,with NMR data that were also reported. Compounds 1-3,7,8,23,25-30 were isolated from P. ginseng flower buds for the first time.
This project is to investigate the chemical constituents of ginsenosides from the flower buds of Panax ginseng. The compounds were isolated by using a variety of chromatographic methods including Diaion HP-20,silica gel,MCI gel and semi-preparative HPLC chromatography. Their structures were identified by NMR,and MS data. As a result,32 compounds were isolated from the extract of P. ginseng flower buds,and identified as ginsenoside Rk_3( 1),ginsenoside Rh_4( 2),ginsenoside Rh_8( 3),pseudoginsenoside Rc_1( 4),ginsenoside Rc( 5),ginsenoside Rb_2( 6),ginsenoside Rg_6( 7),20( E)-ginsenoside F_4( 8),ginsenoside Rb_1( 9),vinaginsenoside R_(16)( 10),ginsenoside Rh_6( 11),vinaginsenoside R_3( 12),5,6-didehydro-ginsenoside Rd( 13),vinaginsenoside R_4( 14),vinaginsenoside R_8( 15),ginsenoside Rf( 16),notoginsenoside E( 17),ginsenoside Ⅲ( 18),3-O-β-D-glucopyranosyl-3β,7β,12β,20 S-tetrahydroxydammar-5( 6),24-diene-20-O-β-D-glucopyranoside( 19),20( S)-ginsenoside Rg_2( 20),20( R)-ginsenoside Rg_2( 21),notoginsenoside R_2( 22),ginsenoside F_2( 23),quinquenoside I( 24),ginsenoside M_1( 25),quinquenoside L_(10)( 26),ginsenoside Rh_5( 27),ginsenoside Rg_5( 28),ginsenoside Rk_1( 29),20( R)-ginsenoside Rg_3( 30),oleanolic acid 3-O-β-D-glucopyranosyl-( 1→2)-β-D-( 6'-methyl ester)-glucuronopyranoside( 31) and ginsenoside MC( 32). Among them,compounds 10,12,13,15,19,22,24,31 and 32 were isolated from P. ginseng for the first time,and compound 19 was a genuine ginsenoside firstly obtained by separation and identification,with NMR data that were also reported. Compounds 1-3,7,8,23,25-30 were isolated from P. ginseng flower buds for the first time.
引文
[1]杨秀伟,富力.人参中三萜类化学成分的生物学活性和药理学作用[J].中国现代中药,2016,18(1):36.
[2] Shin B,Kwon S W,Park J H. Chemical diversity of ginseng saponins from Panax ginseng[J]. J Ginseng Res,2015,39(4):287.
[3] Li K K,Gong X J. A review on the medicinal potentials of Panax ginseng saponins in diabetes mellitus[J]. RSC Advances,2015,5(59):47353.
[4] Yang X D,Yang Y Y,Ouyang D S,et al. A review of biotransformation and pharmacology of ginsenoside compound K[J]. Fitoterapia,2015,100:208.
[5]李珂珂,杨秀伟.人参茎叶化学成分的研究进展[J].中国现代中药,2012,14(1):47.
[6]杨秀伟.人参中三萜类化学成分的研究[J].中国现代中药,2016,18(1):7.
[7] Attele A S,Wu J A,Yuan C S. Ginseng pharmacology:multiple constituents and multiple actions[J]. Biochem Pharm,1999,58(11):1685.
[8] Li K K,Yao C M,Yang X W. Four new dammarane-type triterpene saponins from the stems and leaves of Panax ginseng and their cytotoxicity on HL-60 cells[J]. Planta Med,2012,78(2):189.
[9] Li K K,Yang X W. Minor triterpene compounds from the stems and leaves of Panax ginseng[J]. Fitoterpia,2012,83(6):1030.
[10]李珂珂,杨秀伟.人参茎叶中1个新三萜类天然产物[J].中草药,2015,46(2):169.
[11]杨秀伟,李珂珂,周琪乐.人参茎叶中1个新皂苷20(S)-人参皂苷Rf2[J].中草药,2015,46(21):3137.
[12] Li K K,Xu F,Gong X J. Isolation,purification and quantification of ginsenoside F5and F3isomeric compounds from crude extracts of flower buds of Panax ginseng[J]. Molecules,2016,21(3):315.
[13] Li S S,Li K K,Xu F,et al. A strategy for simultaneous isolation of less polar ginsenosides,including a pair of new 20-methoxyl isomers,from flower buds of Panax ginseng[J]. Molecules,2017,22(3):442.
[14]徐斐,李珂珂,陈丽荣,等.人参花醇提物中的皂苷类化学成分[J].中国现代中药,2016,18(1):67.
[15]陶丽,李珂珂,李东霞,等.人参果中的皂苷类化学成分研究[J].中国现代中药,2018,20(8):928.
[16] Li K K,Xu F,Li S S,et al. Cytotoxic epimeric ginsenosides from the flower buds of Panax ginseng[J]. Steroids,2019,143:1.
[17] Li K K,Li S S,Xu F,et al. A novel acylated quercetin glycoside and compounds of inhibitory effects onα-glucosidase from Panax ginseng flower buds[J]. Nat Prod Res,doi:10. 1080/14786419. 2018. 1543685.
[18] Li K K,Li S S,Xu F,et al. Six new dammarane-type triterpene saponins from Panax ginseng flower buds and their cytotoxicity[J]. J Ginseng Res,doi:10. 1016/j.jgr.2018. 12. 008.
[19]李珂珂,弓晓杰,陈丽荣,等.3β-乙酰氧基人参皂苷F1及其提取方法和药物用途:中国,CN105330713A[P]. 2016-02-17.
[20]李珂珂,弓晓杰,陈丽荣,等.6'-丙二酸单甲酯酰基人参皂苷F1及其提取方法和药物用途:中国,CN105418718A[P].2016-03-23.
[21] Yoshikawa M,Morikawa T,Ueno T,et al. Bioactive saponins and glycosides.Ⅸ. Notoginseng(2):structures of five new dammarane-type triterpene oligoglycosides,notoginsenosides-E,-G,-H,-I,and-J,and a novel acetylenic fatty acid glycoside,notoginsenic acidβ-sophoroside,from the dried root of Panax notoginseng(Burk.)F. H. Chen[J]. Chem Pharm Bull,1997,45(6):1056.
[22] Yoshikawa M,Murakami T,Yashiro K,et al. Bioactive saponins and glycosides.Ⅺ. Structures of new dammarane-type triterpene oligoglycosides,quinquenosidesⅠ,Ⅱ,Ⅲ,Ⅳ,andⅤ,from American ginseng,the roots of Panax quinquefolium L[J]. Chem Pharm Bull,1998,46(4):647.
[23] Liu Y,Li J,He J,et al. Identification of new trace triterpenoid saponins from the roots of Panax notoginseng by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry[J]. Rapid Commun Mass Spectrom,2009,23(5):667.
[24] Xing Q Q,Liang T,Shen G B,et al. Comprehensive HILIC×RPLC with mass spectrometry detection for the analysis of saponins in Panax notoginseng[J]. Analyst,2012,137(9):2239.
[25] Park I H,Kim N Y,Han S B,et al. Three new dammarane glycosides from heat processed ginseng[J]. Arch Pharm Res,2002,25(4):428.
[26] Baek N I,Kim D S,Lee Y H,et al. Ginsenoside Rh4,a genuine dammarane glycoside from Korean red ginseng[J]. Planta Med,1996,62(1):86.
[27] Dou D Q,Chen Y J,Liang L H,et al. Six new dammarane-type triterpene saponins from the leaves of Panax ginseng[J]. Chem Pharm Bull,2001,49(4):442.
[28] Namba T,Matsushige K,Morita T,et al. Saponins of plants of Panax species collected in central nepal and their chemotaxonomical significance.Ⅰ[J]. Chem Pharm Bull,1986,34(2):730.
[29] Sanada S,Kondo N,Shoji J,et al. Studies on the saponins of ginseng. I. Structures of ginsenoside-Ro,-Rb1,-Rb2,-Rc,and Rd[J]. Chem Pharm Bull,1974,22(2):421.
[30] Ryu J H,Park J H,Eun J H,et al. A dammarane glycoside from Korean red ginseng[J]. Phytochemistry,1997,44(5):931.
[31] Ryu J H,Park J H,Kim T H,et al. A genuine dammarane glycoside,(20E)-ginsenoside F4from Korean red ginseng[J].Arch Pharm Res,1996,19(4):335.
[32] Duc N M,Kasai R,Yamasaki K,et al. New dammarane saponins from Vietnamese ginseng[J]. Stud Plant Sci,1999,6:77.
[33] Duc N M,Kasai R,Ohtani K,et al. Saponins from Vietnamese ginseng,Panax vietnamensis Ha et Grushv. collected in central Vietnam.Ⅱ[J]. Chem Pharm Bull,1994,42(1):115.
[34] Wan J B,Zhang Q W,Hong S J,et al. 5,6-Didehydroginsenosides from the roots of Panax notoginseng[J]. Molecules,2010,15(11):8169.
[35] Sanada S,Kondo N,Shoji J,et al. Studies on the saponins of Ginseng.Ⅱ. Structures of ginsenoside-Re,-Rf and-Rg2[J].Chem Pharm Bull,1974,22(10):2407.
[36] Qiu F,Ma Z Z,Xu S X. et al. Studies on dammaranetype saponins in the flower-buds of Panax ginseng C. A. Meyer[J]. J Asian Nat Prod Res,1998,1(2):119.
[37]杨秀伟. 20(R)和20(S)-人参皂苷-Rg2碳氢NMR信号全指定[J].波谱学杂志,2000,17(1):9.
[38] Zhou J,Wu M Z,Taniyasu S,et al. Dammarane-saponins of Sanchi-ginseng,roots of Panax notoginseng(Burk)F. H. Chen(Araliaceae):structures of new saponins notoginsenoside R1and notoginsenoside R2,and identification of ginsenosides Rg2and ginsenoside Rh1[J]. Chem Pharm Bull,1981,29(10):2844.
[39]窦德强,文晔,裴玉萍,等.人参叶中微量成分的研究[J].中国中药杂志,1997,22(1):35.
[40] Li W F,Li Z N,Chen L R,et al. Synthesis and structure analysis of mono-dodecanoic acid esters of ginsenoside M1[J]. Chin J Nat Med,2011,9(3):199.
[41] Chen J,Zhao R,Zeng Y M,et al. Three new triterpenoid saponins from the leaves and stems of Panax quinquefolium[J]. J Asian Nat Prod Res,2009,11(3):195.
[42] Tran Q L,Adnyana I K,Tezuka Y,et al. Triterpene saponins from Vietnamese ginseng(Panax vietnamensis)and their hepatocytoprotective activity[J]. J Nat Prod,2001,64(4):456.
[43] Kim S I,Park J H,Ryu J H,et al. Ginsenoside Rg5,a genuine dammarane glycoside from Korean red ginseng[J]. Arch Pharm Res,1996,19(5):551.
[44] Zhou M,Xu M,Wang D,et al. New dammarane-type saponins from the Rhizomes of Panax japonicas[J]. Helv Chim Acta,2011,94(11):2010.
[45] Hasegawa H,Sung J H,Matsumiya S,et al. Main ginseng saponin metabolites formed by intestinal bacteria[J]. Planta Med,1996,62(5):453.
[46] Yang W Z,Hu Y,Wu W Y,et al. Saponins in the genus Panax L.(Araliaceae):a systematic review of their chemical diversity[J]. Phytochemistry,2014,106(10):7.
[47] Kim S J,Shin J Y,Ko S K. Changes in the contents of prosapogenin in Red ginseng(Panax ginseng)depending on the extracting conditions[J]. J Ginseng Res,2016,40(1):86.
[48]郑茜,王朝晖,祁增,等.24-羟基-人参二醇的抗癌作用及基于分子对接的机制[J].中国实验方剂学杂志,2019,25(6):81.
[2] Shin B,Kwon S W,Park J H. Chemical diversity of ginseng saponins from Panax ginseng[J]. J Ginseng Res,2015,39(4):287.
[3] Li K K,Gong X J. A review on the medicinal potentials of Panax ginseng saponins in diabetes mellitus[J]. RSC Advances,2015,5(59):47353.
[4] Yang X D,Yang Y Y,Ouyang D S,et al. A review of biotransformation and pharmacology of ginsenoside compound K[J]. Fitoterapia,2015,100:208.
[5]李珂珂,杨秀伟.人参茎叶化学成分的研究进展[J].中国现代中药,2012,14(1):47.
[6]杨秀伟.人参中三萜类化学成分的研究[J].中国现代中药,2016,18(1):7.
[7] Attele A S,Wu J A,Yuan C S. Ginseng pharmacology:multiple constituents and multiple actions[J]. Biochem Pharm,1999,58(11):1685.
[8] Li K K,Yao C M,Yang X W. Four new dammarane-type triterpene saponins from the stems and leaves of Panax ginseng and their cytotoxicity on HL-60 cells[J]. Planta Med,2012,78(2):189.
[9] Li K K,Yang X W. Minor triterpene compounds from the stems and leaves of Panax ginseng[J]. Fitoterpia,2012,83(6):1030.
[10]李珂珂,杨秀伟.人参茎叶中1个新三萜类天然产物[J].中草药,2015,46(2):169.
[11]杨秀伟,李珂珂,周琪乐.人参茎叶中1个新皂苷20(S)-人参皂苷Rf2[J].中草药,2015,46(21):3137.
[12] Li K K,Xu F,Gong X J. Isolation,purification and quantification of ginsenoside F5and F3isomeric compounds from crude extracts of flower buds of Panax ginseng[J]. Molecules,2016,21(3):315.
[13] Li S S,Li K K,Xu F,et al. A strategy for simultaneous isolation of less polar ginsenosides,including a pair of new 20-methoxyl isomers,from flower buds of Panax ginseng[J]. Molecules,2017,22(3):442.
[14]徐斐,李珂珂,陈丽荣,等.人参花醇提物中的皂苷类化学成分[J].中国现代中药,2016,18(1):67.
[15]陶丽,李珂珂,李东霞,等.人参果中的皂苷类化学成分研究[J].中国现代中药,2018,20(8):928.
[16] Li K K,Xu F,Li S S,et al. Cytotoxic epimeric ginsenosides from the flower buds of Panax ginseng[J]. Steroids,2019,143:1.
[17] Li K K,Li S S,Xu F,et al. A novel acylated quercetin glycoside and compounds of inhibitory effects onα-glucosidase from Panax ginseng flower buds[J]. Nat Prod Res,doi:10. 1080/14786419. 2018. 1543685.
[18] Li K K,Li S S,Xu F,et al. Six new dammarane-type triterpene saponins from Panax ginseng flower buds and their cytotoxicity[J]. J Ginseng Res,doi:10. 1016/j.jgr.2018. 12. 008.
[19]李珂珂,弓晓杰,陈丽荣,等.3β-乙酰氧基人参皂苷F1及其提取方法和药物用途:中国,CN105330713A[P]. 2016-02-17.
[20]李珂珂,弓晓杰,陈丽荣,等.6'-丙二酸单甲酯酰基人参皂苷F1及其提取方法和药物用途:中国,CN105418718A[P].2016-03-23.
[21] Yoshikawa M,Morikawa T,Ueno T,et al. Bioactive saponins and glycosides.Ⅸ. Notoginseng(2):structures of five new dammarane-type triterpene oligoglycosides,notoginsenosides-E,-G,-H,-I,and-J,and a novel acetylenic fatty acid glycoside,notoginsenic acidβ-sophoroside,from the dried root of Panax notoginseng(Burk.)F. H. Chen[J]. Chem Pharm Bull,1997,45(6):1056.
[22] Yoshikawa M,Murakami T,Yashiro K,et al. Bioactive saponins and glycosides.Ⅺ. Structures of new dammarane-type triterpene oligoglycosides,quinquenosidesⅠ,Ⅱ,Ⅲ,Ⅳ,andⅤ,from American ginseng,the roots of Panax quinquefolium L[J]. Chem Pharm Bull,1998,46(4):647.
[23] Liu Y,Li J,He J,et al. Identification of new trace triterpenoid saponins from the roots of Panax notoginseng by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry[J]. Rapid Commun Mass Spectrom,2009,23(5):667.
[24] Xing Q Q,Liang T,Shen G B,et al. Comprehensive HILIC×RPLC with mass spectrometry detection for the analysis of saponins in Panax notoginseng[J]. Analyst,2012,137(9):2239.
[25] Park I H,Kim N Y,Han S B,et al. Three new dammarane glycosides from heat processed ginseng[J]. Arch Pharm Res,2002,25(4):428.
[26] Baek N I,Kim D S,Lee Y H,et al. Ginsenoside Rh4,a genuine dammarane glycoside from Korean red ginseng[J]. Planta Med,1996,62(1):86.
[27] Dou D Q,Chen Y J,Liang L H,et al. Six new dammarane-type triterpene saponins from the leaves of Panax ginseng[J]. Chem Pharm Bull,2001,49(4):442.
[28] Namba T,Matsushige K,Morita T,et al. Saponins of plants of Panax species collected in central nepal and their chemotaxonomical significance.Ⅰ[J]. Chem Pharm Bull,1986,34(2):730.
[29] Sanada S,Kondo N,Shoji J,et al. Studies on the saponins of ginseng. I. Structures of ginsenoside-Ro,-Rb1,-Rb2,-Rc,and Rd[J]. Chem Pharm Bull,1974,22(2):421.
[30] Ryu J H,Park J H,Eun J H,et al. A dammarane glycoside from Korean red ginseng[J]. Phytochemistry,1997,44(5):931.
[31] Ryu J H,Park J H,Kim T H,et al. A genuine dammarane glycoside,(20E)-ginsenoside F4from Korean red ginseng[J].Arch Pharm Res,1996,19(4):335.
[32] Duc N M,Kasai R,Yamasaki K,et al. New dammarane saponins from Vietnamese ginseng[J]. Stud Plant Sci,1999,6:77.
[33] Duc N M,Kasai R,Ohtani K,et al. Saponins from Vietnamese ginseng,Panax vietnamensis Ha et Grushv. collected in central Vietnam.Ⅱ[J]. Chem Pharm Bull,1994,42(1):115.
[34] Wan J B,Zhang Q W,Hong S J,et al. 5,6-Didehydroginsenosides from the roots of Panax notoginseng[J]. Molecules,2010,15(11):8169.
[35] Sanada S,Kondo N,Shoji J,et al. Studies on the saponins of Ginseng.Ⅱ. Structures of ginsenoside-Re,-Rf and-Rg2[J].Chem Pharm Bull,1974,22(10):2407.
[36] Qiu F,Ma Z Z,Xu S X. et al. Studies on dammaranetype saponins in the flower-buds of Panax ginseng C. A. Meyer[J]. J Asian Nat Prod Res,1998,1(2):119.
[37]杨秀伟. 20(R)和20(S)-人参皂苷-Rg2碳氢NMR信号全指定[J].波谱学杂志,2000,17(1):9.
[38] Zhou J,Wu M Z,Taniyasu S,et al. Dammarane-saponins of Sanchi-ginseng,roots of Panax notoginseng(Burk)F. H. Chen(Araliaceae):structures of new saponins notoginsenoside R1and notoginsenoside R2,and identification of ginsenosides Rg2and ginsenoside Rh1[J]. Chem Pharm Bull,1981,29(10):2844.
[39]窦德强,文晔,裴玉萍,等.人参叶中微量成分的研究[J].中国中药杂志,1997,22(1):35.
[40] Li W F,Li Z N,Chen L R,et al. Synthesis and structure analysis of mono-dodecanoic acid esters of ginsenoside M1[J]. Chin J Nat Med,2011,9(3):199.
[41] Chen J,Zhao R,Zeng Y M,et al. Three new triterpenoid saponins from the leaves and stems of Panax quinquefolium[J]. J Asian Nat Prod Res,2009,11(3):195.
[42] Tran Q L,Adnyana I K,Tezuka Y,et al. Triterpene saponins from Vietnamese ginseng(Panax vietnamensis)and their hepatocytoprotective activity[J]. J Nat Prod,2001,64(4):456.
[43] Kim S I,Park J H,Ryu J H,et al. Ginsenoside Rg5,a genuine dammarane glycoside from Korean red ginseng[J]. Arch Pharm Res,1996,19(5):551.
[44] Zhou M,Xu M,Wang D,et al. New dammarane-type saponins from the Rhizomes of Panax japonicas[J]. Helv Chim Acta,2011,94(11):2010.
[45] Hasegawa H,Sung J H,Matsumiya S,et al. Main ginseng saponin metabolites formed by intestinal bacteria[J]. Planta Med,1996,62(5):453.
[46] Yang W Z,Hu Y,Wu W Y,et al. Saponins in the genus Panax L.(Araliaceae):a systematic review of their chemical diversity[J]. Phytochemistry,2014,106(10):7.
[47] Kim S J,Shin J Y,Ko S K. Changes in the contents of prosapogenin in Red ginseng(Panax ginseng)depending on the extracting conditions[J]. J Ginseng Res,2016,40(1):86.
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