植物三七中皂苷类化学成分的研究进展
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摘要
三七总皂苷是中药三七[Notoginseng Radixet Rhizoma]的主要活性成分,具有止血与活血、改善心脑血管系统、抗炎、抗肿瘤和提高机体免疫力等药理作用,三七总皂苷的研究得到了广泛关注,成为中药研究中的重要领域,研究十分活跃.本文结合作者的工作基础及国内外相关文献,对三七中的皂苷类化学成分按照结构类型、皂苷来源进行了系统归纳,综述了三七活性成分在止血、活血、抗炎、抗肿瘤、提高免疫力等方面的药理作用,以期为三七中皂苷类成分的进一步研究提供参考.
Saponins as the main effective constituent of Sanqi,are widely used in the treatment of stroke hemiplegia,cerebral infarction,cerebral thrombosis,cerebral hemorrhage sequelae,and retinal vein occlusion etc.The investigation on notoginseng has become an active and hot topic in traditional Chinese drugs.A great deal of effort has been devoted to this field,and many remarkable results were achieved.Herein,combining with authors' researches and referring to the works from literatures,the research progress of chemical constituents of saponins in Panax notoginsengare systematically reviewed in this article based on the structure and source.Their pharmaceutical activities in hemostasis,promoting blood circulation,anti-inflammatory,antitumor,immunity enhancement effects were also presented with the aim of providing new reference for further study of saponins in sanqi in the future.
Saponins as the main effective constituent of Sanqi,are widely used in the treatment of stroke hemiplegia,cerebral infarction,cerebral thrombosis,cerebral hemorrhage sequelae,and retinal vein occlusion etc.The investigation on notoginseng has become an active and hot topic in traditional Chinese drugs.A great deal of effort has been devoted to this field,and many remarkable results were achieved.Herein,combining with authors' researches and referring to the works from literatures,the research progress of chemical constituents of saponins in Panax notoginsengare systematically reviewed in this article based on the structure and source.Their pharmaceutical activities in hemostasis,promoting blood circulation,anti-inflammatory,antitumor,immunity enhancement effects were also presented with the aim of providing new reference for further study of saponins in sanqi in the future.
引文
[1]国家药典委员会.中华人民共和国药典[M].中国医药科技出版社,2015.
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[3]Yang T R,Kasai R,Zhou J,et al.Dammarane saponins of leaves and seeds of Panax notoginseng[J].Phytochemistry,1983,22(6):1473-1478.
[4]Yoshikawa M,Murakami T,Ueno T,et al.Bioactive saponins and glycosides.VIII.Notoginseng(1):new dammarane-type triterpene oligoglycosides,notoginsenosides-A,B,C,and D,from the dried root of Panax notoginseng(Burk.)f.H.Chen[J].Chem Pharm Bull,1997,45(6):1039-1045.
[5]Yoshikawa M,Murakami T,Ueno T,et al.Bioactive saponins and glycosides.IX.Notoginseng(2):structures of five new dammaranetype 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):1056-1062.
[6]Wei G M,Masanori M,Karl E M,et al.Saponins from the root of Panax notoginseng[J].Phytochemistry,1999,52(6):1133-1139.
[7]Yoshikawa M,Morikawa T,Kashima Y,et al.Structures of new dammarane-type triterpene saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal ginseng saponins[J].J Nat Prod,2003,66(7):922-927.
[8]Yoshikawa M,Murakami T,Yashiro K,et al.Bioactive saponins and glycosides.XIX.Notoginseng(3):Immunological adjuvant activity of notoginsenosides andrelated saponins:Structures of notoginsenosides-L,M,and N from the roots of Panax notoginseng(Burk.)F.H.Chen[J].Chem Pharm Bull,2001,49(11):1452-1456.
[9]Chen J T,Li H Z,Wang D,et al.New dammarane monodesmosides from the acidic deglycosylation of notoginseng-leaf saponins[J].Helv Chim Acta,2006,89(7):1442-1448.
[10]Pei Y,Du Q,Liao P Y,et al.Notoginsenoside ST-4inhibits virus penetration of herpes simplex virus in vitro[J].J Asian Nat Prod Res,2011,13(6):498-504.
[11]Li D,Cao J,Bi X.New dammarane-type triterpenoids from the leaves of Panax notoginsengand their protein tyrosine phosphatase 1B inhibitory activity[J].J Gins Res,2014,38(1):28-33.
[12]Hideaki O,Yukio M,Yukio O,et al.The evaluation of ginseng and its congeners by droplet counter-current chromatography(DCC)[J].Planta Med,1977,32(5):9-17.
[13]Liu J H,Wang X,Cai S Q,et al.Analysis of the constituents in the Chinese drug notoginseng by liquid chromatography-electrospray mass spectrometry[J].J Chin Pharm Sci,2004,13(4):225-237.
[14]Wu M Z,et al.Studies on the saponin components of plants in Yunnan.IV.Two saponins of Panax notoginseng[J].Acta Bot Yunnanica,1979,1:119-124
[15]Taniyasu S,Tanaka O,Yang T R,et al.Dammarane saponins of flower buds of Panax notoginseng(Sanchi-Ginseng)[J].Planta Med,1982,44(2):124-125.
[16]Sanada S,Shoji J.Comparative studies on the saponins of ginseng and related crude drugs[J].Shoyakugaku Zasshi,1978,32:96-99.
[17]Liao P Y,Wang D,Zhang Y J,et al.Dammarane-type glycosides from steamed notoginseng[J].J Agric Food Chem,2008,56(5):1751-1756.
[18]李海舟,张颖君,杨崇仁.三七叶化学成分的进一步研究[J].天然产物研究与开发,2006,18(4):549-554.
[19]姜彬慧,王承志,韩颖,等.三七叶中微量活性皂苷的分离与鉴定[J].中药材,2004,27(7):489-491.
[20]Chen Y,Zhan E,Chen H,et al.Saponins with low sugar chain from the leaves of Panax notoginseng(Burk)F.H.Chen[J].J Chin Med Mater,2002,25:176-178.
[21]Matsuura H,Kasai R,Tanaka O,et al.Further studies on dammarane-saponins of Sanchi-Ginseng[J].Chem Pharm Bull,1983,31:2281-2287.
[22]Yang T R,Kasai R,Zhou J,et al.Dammarane saponins of leaves and seeds of Panax notoginseng[J].Phytochemistry,1983,22:1473-1478.
[23]Wei J,Du Y,et al.Study and development of Sanchi(Panax notoginseng(Burk.)F.H.Chen)[J].Nat Prod Res Dev,1992,4:94-100.
[24]李海舟,张颖君,杨崇仁.三七叶化学成分的进一步研究[J].天然产物研究与开发,2006,18(4):549-554.
[25]Zhou J,Wu M Z,Taniyasu S,et al.Dammarane-Saponins of sanqi-ginseng,roots of Panax notoginseng:structures of new saponins,notoginsenosides-R1and-R2,and identification of ginsenoside-Rg2and Rh1[J].Chem Pharm Bull,1981,29:2844-2850.
[26]魏均娴,徐榕雪,王菊芬.三七绒根化学成分研究[J].昆明医学院学报,1988,9(2):6-10.
[27]Li F H,Kaunda J S,Li L L,et al.Saponins from Roots of Panax notoginseng[J].Chinese Herbal Medicines,2014,6(2):159-163.
[28]Teng R W,Li H Z,Wang D Z,et al.Hydrolytic reaction of plant extracts to generate molecular diversity:new dammarane glycosides from the mild acid hydrolysate of root saponins of Panax notoginseng[J].Helv Chim Aacta,2004,87(5):1270-1278.
[29]Sun H,Yang Z,Ye Y,et al.Structure and biological activity of protopanaxatriol-type saponins from the roots of Panax notoginseng[J].Nt Immunopharmacol,2006,6(1):14-25.
[30]Cui X M,Jiang Z Y,Zeng J,et al.Two new dammarane triterpene glycosides from the rhizomes of Panax notoginseng[J].J Asian Nat Prod Res,2008,10(9):845-849.
[31]赵承嘏,朱任宏.中药三七之两种皂苷[J].中国生理学杂志,1937,12(1):59-66.
[32]周家明,曾江,崔秀明,等.三七根茎的化学成分研究[J].中国中药杂志,2007,32(4):349-350.
[33]刘利民,张晓琦,汪豪,等.三七主根的微量皂苷类成分研究[J].中国药科大学学报,2011,42(2):115-118.
[34]Zhao P,Liu Y,Yang C,et al.Minor constituents from the roots of Panax notoginseng[J].Acta Bot Yunnan,1993(15):409-412.
[35]Zhao P,Liu Y Q,Yang C R,et al.Minor dammarane saponins fromPanax notoginseng[J].Phytochemistry,1996,41(5):1419-1422.
[36]Li H Z,Teng R W,Yang C R,et al.A novel hexanordammarane glycoside from the roots of Panax notoginseng[J].Chin Chem Lett,2001(1):59-62.
[37]Wang X Y,Wang D,Ma X X,et al.Two new dammarane-type bisdesmosides from the fruit pedicels of Panax notoginseng[J].Helv Chim Acta,2008,91(1):60-66.
[38]魏均娴,王良安,杜华,等.三七绒根中皂苷B1和B2的分离和鉴定[J].药学学报,1985,20(4):288-293.
[39]Liu Q,Lv J J,Xu M,et al.Dammarane-type saponins from steamed leaves of Panax Notoginseng[J].Nat Prod Bioprospect,2011,1(3):124.
[40]Cen Y,Xu F X,Huang X J,et al.A novel 12,23-epoxy dammarane saponin from Panax notoginseng[J].Chin J Nat Med,2015,13(4):303-306.
[41]宋建平,曾江,崔秀明,等.三七根茎的化学成分研究(Ⅱ)[J].云南大学学报(自然科学版),2007,29(3):287-290.
[42]Komakine N,Okasaka M,Takaishi Y,et al.New dammarane-type saponin from roots of Panax notoginseng[J].J Nat Med,2006,60(2):135-137.
[43]Wang J R,Yamasaki Y,Tanaka T,et al.Dammarane-type triterpene saponins from the flowers of Panax notoginseng[J].Molecules,2009,14(6):2087-2094.
[44]王珍,杨靖亚,宋书杰,等.三七素对凝血功能的影响及止血机制[J].中国新药杂志,2014,23(3):356-359.
[45]李兰杰.血塞通注射液药中皂苷类效物质基础研究[N].长春:吉林大学,2016.
[46]Gu C G,Lv J J,Zhang Y J,et al.Minor dehydrogenated and cleavaged dammarane-type saponins from the steamed roots of Panax notoginseng[J].Fitoterapia,2015,103:97-105.
[47]Liu X Y,Wang S,Zhang D M,et al.Dammarane-type saponins from the leaves of Panax notoginseng and their neuroprotective effects on damaged SH-SY5Ycells[J].Phytochemistry,2018,145:10-17.
[48]Huang J W,Li C J,Yang J Z,et al.New dammarane-type saponins from the leaves of Panax notoginseng[J].Chinese Chemical Letters,2018,https://doi.org/10.1016/j.cclet.2018.04.015.
[49]Liu J J,Jiang C Y,Wang J B,et al.Notoginsenoside Fc attenuates high glucose-induced vascular endothelial cell injury via upregulation of PPAR-γin diabetic Sprague-Dawley rats[J].Vascular Pharmacology,2018,https://doi.org/10.1016/j.vph.2018.05.009.
[50]Wong Z W,Thanikachalam P V,Ramamurthy S,et al.Molecular understanding of the protective role of natural products on isoproterenol-induced myocardial infarction:A review[J].Biomedicine&Pharmacotherapy,2017,94:1145-1166.
[51]Yang B Y,Yuen S C,Lee Y,et al.Identification of certain Panax species to be potential substitutes for Panax notoginseng in hemostatic treatments[J].Pharmacological Research,2018,134:1-15.
[52]Zhou X,Chen B B,Chen Y C,et al.Chemosynthesis pathway and bioactivities comparison of saponins in radix and flower of Panax notoginseng(Burk.)F.H.Chen[J].Journal of Ethnopharmacology,2017,201:56-72.
[53]Wu Q,Deng J J,Wang S S,et al.Ginsenoside Rh4induces apoptosis and autophagic cell death through activation of the ROS/JNK/p53pathway in colorectal cancer cells[J].Biochemical Pharmacology,2018,148:64-74.
[2]Matsuura H,Kasai R,Tanaka O,et al.Further studies on dammarane saponins of Sanchi Ginseng[J].Chem Pharm Bull,1983,31(7):2281-2287.
[3]Yang T R,Kasai R,Zhou J,et al.Dammarane saponins of leaves and seeds of Panax notoginseng[J].Phytochemistry,1983,22(6):1473-1478.
[4]Yoshikawa M,Murakami T,Ueno T,et al.Bioactive saponins and glycosides.VIII.Notoginseng(1):new dammarane-type triterpene oligoglycosides,notoginsenosides-A,B,C,and D,from the dried root of Panax notoginseng(Burk.)f.H.Chen[J].Chem Pharm Bull,1997,45(6):1039-1045.
[5]Yoshikawa M,Murakami T,Ueno T,et al.Bioactive saponins and glycosides.IX.Notoginseng(2):structures of five new dammaranetype 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):1056-1062.
[6]Wei G M,Masanori M,Karl E M,et al.Saponins from the root of Panax notoginseng[J].Phytochemistry,1999,52(6):1133-1139.
[7]Yoshikawa M,Morikawa T,Kashima Y,et al.Structures of new dammarane-type triterpene saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal ginseng saponins[J].J Nat Prod,2003,66(7):922-927.
[8]Yoshikawa M,Murakami T,Yashiro K,et al.Bioactive saponins and glycosides.XIX.Notoginseng(3):Immunological adjuvant activity of notoginsenosides andrelated saponins:Structures of notoginsenosides-L,M,and N from the roots of Panax notoginseng(Burk.)F.H.Chen[J].Chem Pharm Bull,2001,49(11):1452-1456.
[9]Chen J T,Li H Z,Wang D,et al.New dammarane monodesmosides from the acidic deglycosylation of notoginseng-leaf saponins[J].Helv Chim Acta,2006,89(7):1442-1448.
[10]Pei Y,Du Q,Liao P Y,et al.Notoginsenoside ST-4inhibits virus penetration of herpes simplex virus in vitro[J].J Asian Nat Prod Res,2011,13(6):498-504.
[11]Li D,Cao J,Bi X.New dammarane-type triterpenoids from the leaves of Panax notoginsengand their protein tyrosine phosphatase 1B inhibitory activity[J].J Gins Res,2014,38(1):28-33.
[12]Hideaki O,Yukio M,Yukio O,et al.The evaluation of ginseng and its congeners by droplet counter-current chromatography(DCC)[J].Planta Med,1977,32(5):9-17.
[13]Liu J H,Wang X,Cai S Q,et al.Analysis of the constituents in the Chinese drug notoginseng by liquid chromatography-electrospray mass spectrometry[J].J Chin Pharm Sci,2004,13(4):225-237.
[14]Wu M Z,et al.Studies on the saponin components of plants in Yunnan.IV.Two saponins of Panax notoginseng[J].Acta Bot Yunnanica,1979,1:119-124
[15]Taniyasu S,Tanaka O,Yang T R,et al.Dammarane saponins of flower buds of Panax notoginseng(Sanchi-Ginseng)[J].Planta Med,1982,44(2):124-125.
[16]Sanada S,Shoji J.Comparative studies on the saponins of ginseng and related crude drugs[J].Shoyakugaku Zasshi,1978,32:96-99.
[17]Liao P Y,Wang D,Zhang Y J,et al.Dammarane-type glycosides from steamed notoginseng[J].J Agric Food Chem,2008,56(5):1751-1756.
[18]李海舟,张颖君,杨崇仁.三七叶化学成分的进一步研究[J].天然产物研究与开发,2006,18(4):549-554.
[19]姜彬慧,王承志,韩颖,等.三七叶中微量活性皂苷的分离与鉴定[J].中药材,2004,27(7):489-491.
[20]Chen Y,Zhan E,Chen H,et al.Saponins with low sugar chain from the leaves of Panax notoginseng(Burk)F.H.Chen[J].J Chin Med Mater,2002,25:176-178.
[21]Matsuura H,Kasai R,Tanaka O,et al.Further studies on dammarane-saponins of Sanchi-Ginseng[J].Chem Pharm Bull,1983,31:2281-2287.
[22]Yang T R,Kasai R,Zhou J,et al.Dammarane saponins of leaves and seeds of Panax notoginseng[J].Phytochemistry,1983,22:1473-1478.
[23]Wei J,Du Y,et al.Study and development of Sanchi(Panax notoginseng(Burk.)F.H.Chen)[J].Nat Prod Res Dev,1992,4:94-100.
[24]李海舟,张颖君,杨崇仁.三七叶化学成分的进一步研究[J].天然产物研究与开发,2006,18(4):549-554.
[25]Zhou J,Wu M Z,Taniyasu S,et al.Dammarane-Saponins of sanqi-ginseng,roots of Panax notoginseng:structures of new saponins,notoginsenosides-R1and-R2,and identification of ginsenoside-Rg2and Rh1[J].Chem Pharm Bull,1981,29:2844-2850.
[26]魏均娴,徐榕雪,王菊芬.三七绒根化学成分研究[J].昆明医学院学报,1988,9(2):6-10.
[27]Li F H,Kaunda J S,Li L L,et al.Saponins from Roots of Panax notoginseng[J].Chinese Herbal Medicines,2014,6(2):159-163.
[28]Teng R W,Li H Z,Wang D Z,et al.Hydrolytic reaction of plant extracts to generate molecular diversity:new dammarane glycosides from the mild acid hydrolysate of root saponins of Panax notoginseng[J].Helv Chim Aacta,2004,87(5):1270-1278.
[29]Sun H,Yang Z,Ye Y,et al.Structure and biological activity of protopanaxatriol-type saponins from the roots of Panax notoginseng[J].Nt Immunopharmacol,2006,6(1):14-25.
[30]Cui X M,Jiang Z Y,Zeng J,et al.Two new dammarane triterpene glycosides from the rhizomes of Panax notoginseng[J].J Asian Nat Prod Res,2008,10(9):845-849.
[31]赵承嘏,朱任宏.中药三七之两种皂苷[J].中国生理学杂志,1937,12(1):59-66.
[32]周家明,曾江,崔秀明,等.三七根茎的化学成分研究[J].中国中药杂志,2007,32(4):349-350.
[33]刘利民,张晓琦,汪豪,等.三七主根的微量皂苷类成分研究[J].中国药科大学学报,2011,42(2):115-118.
[34]Zhao P,Liu Y,Yang C,et al.Minor constituents from the roots of Panax notoginseng[J].Acta Bot Yunnan,1993(15):409-412.
[35]Zhao P,Liu Y Q,Yang C R,et al.Minor dammarane saponins fromPanax notoginseng[J].Phytochemistry,1996,41(5):1419-1422.
[36]Li H Z,Teng R W,Yang C R,et al.A novel hexanordammarane glycoside from the roots of Panax notoginseng[J].Chin Chem Lett,2001(1):59-62.
[37]Wang X Y,Wang D,Ma X X,et al.Two new dammarane-type bisdesmosides from the fruit pedicels of Panax notoginseng[J].Helv Chim Acta,2008,91(1):60-66.
[38]魏均娴,王良安,杜华,等.三七绒根中皂苷B1和B2的分离和鉴定[J].药学学报,1985,20(4):288-293.
[39]Liu Q,Lv J J,Xu M,et al.Dammarane-type saponins from steamed leaves of Panax Notoginseng[J].Nat Prod Bioprospect,2011,1(3):124.
[40]Cen Y,Xu F X,Huang X J,et al.A novel 12,23-epoxy dammarane saponin from Panax notoginseng[J].Chin J Nat Med,2015,13(4):303-306.
[41]宋建平,曾江,崔秀明,等.三七根茎的化学成分研究(Ⅱ)[J].云南大学学报(自然科学版),2007,29(3):287-290.
[42]Komakine N,Okasaka M,Takaishi Y,et al.New dammarane-type saponin from roots of Panax notoginseng[J].J Nat Med,2006,60(2):135-137.
[43]Wang J R,Yamasaki Y,Tanaka T,et al.Dammarane-type triterpene saponins from the flowers of Panax notoginseng[J].Molecules,2009,14(6):2087-2094.
[44]王珍,杨靖亚,宋书杰,等.三七素对凝血功能的影响及止血机制[J].中国新药杂志,2014,23(3):356-359.
[45]李兰杰.血塞通注射液药中皂苷类效物质基础研究[N].长春:吉林大学,2016.
[46]Gu C G,Lv J J,Zhang Y J,et al.Minor dehydrogenated and cleavaged dammarane-type saponins from the steamed roots of Panax notoginseng[J].Fitoterapia,2015,103:97-105.
[47]Liu X Y,Wang S,Zhang D M,et al.Dammarane-type saponins from the leaves of Panax notoginseng and their neuroprotective effects on damaged SH-SY5Ycells[J].Phytochemistry,2018,145:10-17.
[48]Huang J W,Li C J,Yang J Z,et al.New dammarane-type saponins from the leaves of Panax notoginseng[J].Chinese Chemical Letters,2018,https://doi.org/10.1016/j.cclet.2018.04.015.
[49]Liu J J,Jiang C Y,Wang J B,et al.Notoginsenoside Fc attenuates high glucose-induced vascular endothelial cell injury via upregulation of PPAR-γin diabetic Sprague-Dawley rats[J].Vascular Pharmacology,2018,https://doi.org/10.1016/j.vph.2018.05.009.
[50]Wong Z W,Thanikachalam P V,Ramamurthy S,et al.Molecular understanding of the protective role of natural products on isoproterenol-induced myocardial infarction:A review[J].Biomedicine&Pharmacotherapy,2017,94:1145-1166.
[51]Yang B Y,Yuen S C,Lee Y,et al.Identification of certain Panax species to be potential substitutes for Panax notoginseng in hemostatic treatments[J].Pharmacological Research,2018,134:1-15.
[52]Zhou X,Chen B B,Chen Y C,et al.Chemosynthesis pathway and bioactivities comparison of saponins in radix and flower of Panax notoginseng(Burk.)F.H.Chen[J].Journal of Ethnopharmacology,2017,201:56-72.
[53]Wu Q,Deng J J,Wang S S,et al.Ginsenoside Rh4induces apoptosis and autophagic cell death through activation of the ROS/JNK/p53pathway in colorectal cancer cells[J].Biochemical Pharmacology,2018,148:64-74.