Chemical diversity of ginseng saponins from Panax ginseng

Journal of Ginseng Research

Volumn 39, Issue 4, 2015, Pages 287-298

  Shin, Byong Kyu ^a   Kwon, Sung Won ^a   Park, Jeong Hill ^a  

^a Seoul National University   (South Korea)

Author keywords

Araliaceae; Dammarane; Ginsenoside; Panax ginseng; Triterpene

Indexed keywords

AGLYCONE; DAMMARANE DERIVATIVE; GINSENG SAPONIN; GINSENOSIDE; GLYCOSIDE; OCOTILLOL; PROTOPANAXADIOL; PROTOPANAXATRIOL; TRITERPENE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARALIACEAE; BIOLOGICAL ACTIVITY; BIOTRANSFORMATION; CHEMICAL ANALYSIS; CHEMICAL DIVERSITY; CHEMICAL STRUCTURE; DEHYDRATION; FLOWER; GINSENG; HEART MUSCLE ISCHEMIA; HEART PROTECTION; HYDRATION; METABOLITE; NONHUMAN; PERENNIAL PLANT; PEROXIDATION; PLANT LEAF; PLANT ROOT; PRIORITY JOURNAL; REVIEW;

EID: 84942830473     PISSN: 12268453     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jgr.2014.12.005     Document Type: Review

References (68)

1. Yun TK. Brief introduction of Panax ginseng C. A. Meyer. J Korean Med Sci 2001;16:S3-5.
2. Hu SY. The genus Panax (Ginseng) in Chinese medicine. Econ Bot 1976;30:11-28.
3. Roskov Y, Kunze T, Orrell T, Abucay L, Paglinawan L, Culham A, Bailly N, Kirk P, Bourgoin T, Baillargeon G, et al., editors. Species 2000 & ITIS catalogue of life; 2014. 2014 Annual Checklist. Digital resource at,www.catalogueoflife.org/ annual-checklist/2014. Species 2000: Naturalis, Leiden, the Netherlands.
4. Hu SY. A contribution to our knowledge of ginseng. Am J Chin Med 1977;5:1-23.
5. Petkov W. Pharmacological studies of the drug P. ginseng C. A. Meyer. Arzneim Forsch 1959;9:305-11.
6. Kim SK, Park JH. Trends in ginseng research in 2010. J Ginseng Res 2011;35: 389-98.
7. 157 phosphorylation on thrombin-induced platelet aggregation. J Ginseng Res 2013;37:176-86.
8. Siddiqi MH, Siddiqi MZ, Ahn SG, Kang S, Kim YJ, Sathishkumar N, Yang DU, Yang DC. Ginseng saponins and the treatment of osteoporosis: mini literature review. J Ginseng Res 2013;37:261-8.
9. Kang KS, Ham JY, Kim YJ, Park JH, Cho EJ, Yamabe N. Heat-processed Panax ginseng and diabetic renal damage: active components and action mechanism. J Ginseng Res 2013;37:379-88.
10. Lee S, Kim MG, Ko SK, Kim HK, Leem KH, Kim YJ. Protective effect of ginsenoside Re on acute gastric mucosal lesion induced by compound 48/80. J Ginseng Res 2014;38:89-96.
11. Lee CH, Kim JH. A review on the medicinal potentials of ginseng and ginsenosides on cardiovascular diseases. J Ginseng Res 2014;38:161-6.
12. Elyakov GB, Strigina LI, Uvarova NI, Vaskovsky VE, Dzizenko AK, Kochetkov NK. Glycosides from ginseng roots. Tetrahedron Lett 1964;5: 3591-7.
13. Tansakul P, Shibuya M, Kushiro T, Ebizuka Y. Dammarenediol-II synthase, the first dedicated enzyme for ginsenoside biosynthesis, in Panax ginseng. FEBS Lett 2006;580:5143-9.
14. Shibata S, Tanaka O, Sado M, Tsushima S. On genuine sapogenin of ginseng. Tetrahedron Lett 1963;4:795-800.
15. Shibata S, Tanaka O, Ando T, Sado M, Tsushima S, Ohsawa T. Chemical studies on oriental plant drugs. XIV. Protopanaxadiol, a genuine sapogenin of ginseng saponins. Chem Pharm Bull 1966;14:595-600.
16. Yahara S, Tanaka O, Komori T. Saponins of the leaves of Panax ginseng C. A. Meyer. Chem Pharm Bull 1976;24:2204-8.
17. Besso H, Kasai R, Saruwatari Y, Fuwa T, Tanaka O. Ginsenoside-Ra1 and ginsenoside-Ra2, new dammarane-saponins of ginseng roots. Chem Pharm Bull 1982;30:2380-5.
18. Matsuura H, Kasai R, Tanaka O, Saruwatari Y, Kunihiro K, Fuwa T. Further studies on dammarane-saponins of ginseng roots. Chem Pharm Bull 1984;32: 1188-92.
19. Sanada S, Kondo N, Shoji J, Tanaka O, Shibata S. Studies on the saponins of ginseng. I. Structures of ginsenoside-Ro, -Rb1, -Rb2, -Rc and -Rd. Chem Pharm Bull 1974;22:421-8.
20. Kasai R, Besso H, Tanaka O, Saruwatari Y, Fuwa T. Saponins of red ginseng. Chem Pharm Bull 1983;31:2120-5.
21. Yahara S, Kaji K, Tanaka O. Further study on dammarane-type saponins of roots, leaves, flower-buds, and fruits of Panax ginseng C. A. Meyer. Chem Pharm Bull 1979;27:88-92.
22. Kondo N, Shoji J, Tanaka O. Studies on the constituents of Himalayan ginseng, Panax pseudoginseng. I. The structures of the saponins. (1). Chem Pharm Bull 1973;21:2705-11.
23. Sanada S, Shoji J. Studies on the saponins of ginseng. III. Structures of ginsenoside-Rb3 and 20-glucoginsenoside-Rf. Chem Pharm Bull 1978;26: 1694-7.
24. Yahara S, Matsuura K, Kasai R, Tanaka O. Saponins of buds and flowers of Panax ginseng C. A. Meyer. (1). Isolation of ginsenosides-Rd, -Re, and -Rg1. Chem Pharm Bull 1976;24:3212-3.
25. Kitagawa I, Yoshikawa M, Yoshihara M, Hayashi T, Taniyama T. Chemical studies on crude drug precession. I. On the constituents of Ginseng Radix rubra (1). Yakugaku Zasshi 1983;103:612-22.
26. Baek NI, Kim JM, Park JH, Ryu JH, Kim DS, Lee YH, Park JD, Kim SI. Ginsenoside Rs3, a genuine dammarane-glycoside from Korean red ginseng. Arch Pharm Res 1997;20:280-2.
27. Ruan CC, Liu Z, Li X, Liu X, Wang LJ, Pan HY, Zheng YN, Sun GZ, Zhang YS, Zhang LX. Isolation and characterization of a new ginsenoside from the fresh root of Panax ginseng. Molecules 2010;15:2319-25.
28. Kitagawa I, Taniyama T, Hayashi T, Yoshikawa M. Malonyl-ginesnosides Rb1, Rb2, Rc, and Rd, four new malonylated dammarane-type triterpene oligoglycosides from Ginseng Radix. Chem Pharm Bull 1983;31:3353-6.
29. Sun GZ, Li XG, Liu Z, Wang JY, Zheng YN, Yang XW. Isolation and structure characterization of malonyl-notoginsenoside-R4 from the root of Panax ginseng. Chem J Chin Univ 2007;28:1316-8.
30. Shibata S, Tanaka O, Sôma K, Iida Y, Ando T, Nakamura H. Studies on saponins and sapogenins of ginseng: the structure of panaxatriol. Tetrahedron Lett 1965;6:207-13.
31. Yoshikawa M, Sugimoto S, Nakamura S, Sakumae H, Matsuda H. Medicinal flowers. XVI. New dammarane-type triterpene tetraglycosides and gastroprotective principles from flower buds of Panax ginseng. Chem Pharm Bull 2007;55:1034-8.
32. Sanada S, Kondo N, Shoji J, Tanaka O, Shibata S. Studies on the saponins of ginseng. II. Structures of ginsenoside-Re, -Rf and -Rg2. Chem Pharm Bull 1974;22:2407-12.
33. Iida Y, Tanaka O, Shibata S. Studies on saponins of ginseng: the structure of ginsenoside-Rg1. Tetrahedron Lett 1968;9:5449-53.
34. Zhou JUN, Wu M, Taniyasu S, Besso H, Tanaka O, Saruwatari Y, Fuwa T. Dammarane-saponins of sanchi-ginseng, roots of Panax notoginseng (BURK.) F. H. Chen (Araliaceae): structures of new saponins, notoginsenosides-R1 and -R2, and identification of ginsenosides-Rg2 and -Rh1. Chem Pharm Bull 1981;29:2844-50.
35. 1. Chem Pharm Bull 1976;24:253-61.
36. Nakamura S, Sugimoto S, Matsuda H, Yoshikawa M. Structures of dammaranetype triterpene triglycosides from the flower buds of Panax ginseng. Heterocycles 2007;71:577-88.
37. Nguyen HT, Song GY, Kim JA, Hyun JH, Kang HK, Kim YH. Dammarane-type saponins from the flower buds of Panax ginseng and their effects on human leukemia cells. Bioorg Med Chem Lett 2010;20:309-14.
38. Qiu F, Ma ZZ, Xu SX, Yao XS, Che CT, Chen YJ. A pair of 24-hydroperoxyl epimeric dammarane saponins from flower-buds of Panax ginseng. J Asian Nat Prod Res 2001;3:235-40.
39. Yoshikawa M, Sugimoto S, Nakamura S, Matsuda H. Medicinal flowers. XI. Structures of new dammarane-type triterpene diglycosides with hydroperoxide group from flower buds of Panax ginseng. Chem Pharm Bull 2007;55:571-6.
40. Nguyen HT, Song GY, Nhiem NX, Ding Y, Tai BH, Jin LG, Lim CM, Hyun JW, Park CJ, Kang HK, et al. Dammarane-type saponins from the flower buds of Panax ginseng and their intracellular radical scavenging capacity. J Agric Food Chem 2010;58:868-74.
41. Nguyen HT, Song GY, Minh CV, Kiem PV, Jin LG, Boo HJ, Kang HK, Kim YH. Steamed ginseng-leaf components enhance cytotoxic effects on human leukemia HL-60 cells. Chem Pharm Bull 2010;58:1111-5.
42. Dou DQ, Chen YJ, Liang LH, Pang FG, Shimizu N, Takeda T. Six new dammarane-type triterpene saponins from the leaves of Panax ginseng. Chem Pharm Bull 2001;49:442-6.
43. Nguyen HT, Song GY, Kang HK, Kim YH. New dammarane saponins from the steamed ginseng leaves. Bull Korean Chem Soc 2010;31:2094-6.
44. Nguyen HT, Song GY, Park YJ, Kim YH. Two new dammarane-type saponins from the leaves of Panax ginseng. Chem Pharm Bull 2009;57:1412-4.
45. Wang W, Zhao Y, Rayburn ER, Hill DL, Wang H, Zhang R. In vitro anti-cancer activity and structureeactivity relationships of natural products isolated from fruits of Panax ginseng. Cancer Chemother Pharmacol 2007;59:589-601.
46. Park IH, Han SB, Kim JM, Piao LZ, Kwon SW, Kim NY, Kang TL, Park MK, Park JH. Four new acetylated ginsenosides from processed ginseng (sun ginseng). Arch Pharm Res 2002;25:837-41.
47. Park IH, Kim NY, Han SB, Kim JM, Kwon SW, Kim HJ, Park MK, Park JH. Three new dammarane glycosides from heat processed ginseng. Arch Pharm Res 2002;25:428-32.
48. Kim SI, Park JH, Ryu JH, Park JD, Lee YH, Park JH, Kim TH, Kim JM, Baek NI. Ginsenoside Rg5, a genuine dammarane glycoside from Korean red ginseng. Arch Pharm Res 1996;19:551-3.
49. Kim DS, Baek NI, Lee YH, Park JD, Kim SI. Preparation and structure determination of a new glycoside, (20E)-ginsenoside Rh3, and its isomer from dioltype ginseng saponins. Yakhak Hoeji 1996;39:86-93.
50. Ryu JH, Park JH, Kim TH, Sohn DH, Kim JM, Park JH. A genuine dammarane glycoside, (20E)-ginsenoside F4 from Korean red ginseng. Arch Pharm Res 1996;19:335-6.
51. Baek NI, Kim DS, Lee YH, Park JD, Lee CB, Kim SI. Ginsenoside Rh4, a genuine dammarane glycoside from Korean red ginseng. Planta Med 1996;62:86-7.
52. Lee SM, Shon HJ, Choi CS, Hung TM, Min BS, Bae KH. Ginsenosides from heat processed ginseng. Chem Pharm Bull 2009;57:92-4.
53. Ryu JH, Park JH, Eun JH, Jung JH, Sohn DH. A dammarane glycoside from Korean red ginseng. Phytochemistry 1997;44:931-3.
54. Shibata S, Fujita M, Itokawa H, Tanaka O, Ishii T. Studies on the constituents of Japanese and Chinese crude drugs. XI. Panaxadiol, a sapogenin of ginseng roots. (1). Chem Pharm Bull 1963;11:759-61.
55. Shibata S, Tanaka O, Nagai M, Ishii T. Studies on the constituents of Japanese and Chinese crude drugs. XII. Panaxadiol, a sapogenin of ginseng roots. (2). Chem Pharm Bull 1963;11:762-5.
56. Wang LB, Wu ZH, Gao HY, Huang J, Sun BH, Wu LJ. A new compound with cytotoxic activities from the leaves of Panax ginseng C.A. Meyer. Chin Chem Lett 2008;19:837-40.
57. Sugimoto S, Nakamura S, Matsuda H, Kitagawa N, Yoshikawa M. Chemical constituents from seeds of Panax ginseng: structure of new dammarane-type triterpene ketone, panaxadione, and HPLC comparisons of seeds and flesh. Chem Pharm Bull 2009;57:283-7.
58. Kondo N, Marumoto Y, Shoji J. Studies on the constituents of Panacis Japonici Rhizoma. IV. The structure of chikusetsusaponin V. Chem Pharm Bull 1971;19: 1103-7.
59. Wu LJ, Wang LB, Gao HY, Wu B, Song XM, Tang ZS. A new compound from the leaves of Panax ginseng. Fitoterapia 2007;78:556-60.
60. Tao LN, Meng Q, Yin JY, Xing R, Guo HR. A new panaxadiol from the acid hydrolysate of Panax ginseng. Chin Chem Lett 2009;20:687-9.
61. Lei J, Li X, Gong XJ, Zheng YN. Isolation, synthesis and structures of cytotoxic ginsenoside derivatives. Molecules 2007;12:2140-50.
62. Ko SR, Suzuki Y, Kim YH, Choi KJ. Enzymatic synthesis of two ginsenoside Reb-xylosides. Biosci Biotechnol Biochem 2001;65:1223-6.
63. Han M, Hou JG, Dong CM, Li W, Yu HL, Zheng YN, Chen L. Isolation, synthesis and structures of ginsenoside derivatives and their anti-tumor bioactivity. Molecules 2010;15:399-406.
64. Yi B, W. Tian, Qingguo M, Jiangfen Z, Liang W, Qiang L, Fenglan Z, Haijun S. Synthesis and myocardial ischemia protective effect of ocotillol-type derivatives. Rec Nat Prod 2012;6:242-54.
65. Kumar A, Kumar M, Panwar M, Samarth RM, Park TY, Park MH, Kimura H. Evaluation of chemopreventive action of ginsenoside Rp1. BioFactors 2006;26:29-43.
66. Hasegawa H. Proof of the mysterious efficacy of ginseng: basic and clinical trials: metabolic activation of ginsenoside: deglycosylation by intestinal bacteria and esterification with fatty acid. J Pharmacol Sci 2004;95:153-7.
67. Wieser ME, Holden N, Coplen TB, Böhlke JK, Berglund M, Brand WA, Bièvre PD, Gröning M, Loss RD, Meija J, et al. Atomic weights of the elements 2011 (IUPAC Technical Report). Pure Appl Chem 2013;85:1047-78.
68. Niki E, Yoshida Y, Saito Y, Noguchi N. Lipid peroxidation: mechanisms, inhibition, and biological effects. Biochem Biophys Res Commun 2005;338:668-76.