Chemical diversity of Panax ginseng, Panax quinquifolium, and Panax notoginseng

Journal of Ginseng Research

Volumn 36, Issue 1, 2012, Pages 1-15

  Kim, Dong Hyun ^a  

^a Kyung Hee University   (South Korea)

Author keywords

Biotransformation; Constituents; Panax ginseng; Panax notoginseng; Panax quinquifolium

Indexed keywords

PANAX; PANAX GINSENG; PANAX NOTOGINSENG; PANAX QUINQUEFOLIUS;

EID: 84862925405     PISSN: 12268453     EISSN: None     Source Type: Journal    
DOI: 10.5142/jgr.2012.36.1.1     Document Type: Article

References (152)

1. Li CP, Li RC. An introductory note to ginseng. Am J Chin Med (Gard City N Y) 1973;1:249-261.
2. Attele AS, Wu JA, Yuan CS. Ginseng pharmacology: multiple constituents and multiple actions. Biochem Pharmacol 1999;58:1685-1693.
3. Kennedy DO, Scholey AB. Ginseng: potential for the enhancement of cognitive performance and mood. Pharmacol Biochem Behav 2003;75:687-700.
4. Singh VK, Agarwal SS, Gupta BM. Immunomodulatory activity of Panax ginseng extract. Planta Med 1984;50:462-465.
5. Scaglione F, Ferrara F, Dugnani S, Falchi M, Santoro G, Fraschini F. Immunomodulatory effects of two extracts of Panax ginseng C.A. Meyer. Drugs Exp Clin Res 1990;16:537-542.
6. Garriques SS. On panaquilon, a new vegetable substance. Ann Chem Pharm 1854;90:231-234.
7. Shibata S, Tanaka O, NagaI M, Ishit T. Studies on the constituents of Japanese and Chinese crude drugs. XII. Panaxadiol, a sapogenin of ginseng roots. Chem Pharm Bull (Tokyo) 1963;11:762-765.
8. Shibata S, Ando T, Tanaka O, Meguro Y, Sôma K, Iida Y. Saponins and sapogenins of Panax ginseng C.A. Meyer and some other Panax spp. Yakugaku Zasshi 1965;85:753-755.
9. Shibata S, Tanaka O, Soma K, Aando T, Iida Y, Nakamura H. Studies on saponins and sapogenins of ginseng. The structure of panaxatriol. Tetrahedron Lett 1965;42:207-213.
10. Lu JM, Yao Q, Chen C. Ginseng compounds: an update on their molecular mechanisms and medical applications. Curr Vasc Pharmacol 2009;7:293-302.
11. Choi KT. Botanical characteristics, pharmacological effects and medicinal components of Korean Panax ginseng C A Meyer. Acta Pharmacol Sin 2008;29:1109-1118.
12. Yuan CS, Wang CZ, Wicks SM, Qi LW. Chemical and pharmacological studies of saponins with a focus on) American ginseng. J Ginseng Res 2010;34:160-167.
13. 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. Chem Pharm Bull (Tokyo) 1963;11:759-761.
14. Kitagawa I, Taniyama T, Shibuya H, Noda T, Yoshikawa M. Chemical studies on crude drug processing. V. On the constituents of ginseng radix rubra (2): comparison of the constituents of white ginseng and red ginseng prepared from the same Panax ginseng root. Yakugaku Zasshi 1987;107:495-505.
15. Kitagawa I, Yoshikawa M, Yoshihara M, Hayashi T, Taniyama T. Chemical studies of crude drugs (1). Constituents of ginseng radix rubra. Yakugaku Zasshi 1983;103:612-622.
16. Haruyo K, Shuichi S, Yoshiteru I, Junzo S. Studies on the saponins of ginseng. IV. On the structure and enzymatic hydrolysis of ginsenoside Ra1. Chem Pharm Bull 1982;30:2393-2398.
17. 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;15:2319-2325.
18. Zhu GY, Li YW, Hau DK, Jiang ZH, Yu ZL, Fong WF. Protopanaxatriol-type ginsenosides from the root of Panax ginseng. J Agric Food Chem 2011;59:200-205.
19. Hiromichi B, Ryoji K, Yuhichiro S, Tohru F. Ginsenoside Ra1 and ginsenoside Ra2, new dammarane-saponins of ginseng roots. Chem Pharm Bull 1982;30:2380-2385.
20. Kasai R, Besso H, Tanaka O, Saruwatani Y, Fuwa T. Saponins of red ginseng. Chem Pharm Bull 1983;31:2120-2125.
21. 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;19:335-336.
22. 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;62:86-87.
23. Baek NI, Kim JM, Park JH, Ryu JH, Kim DS, Lee YH, Park JD, Kim SI. Ginsenoside Rs(3), a genuine dammarane-glycoside from Korean red ginseng. Arch Pharm Res 1997;20:280-282.
24. Park JD, Lee YH, Kim SI. Ginsenoside Rf2, a new dammarane glycoside from Korean red ginseng (Panax ginseng). Arch Pharm Res 1998;21:615-617.
25. Shoji Y, Kiyoko K, Osamu T. 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.
26. Shoji Y, Kiyoko M, Ryoji K, Osamu T. Saponins of buds and flowers of Panax ginseng C. A. Meyer. (1). Isolation of ginsenosides-Rd, -Re, and -Rg1. Chem Pharm Bull 1976;24:3212-3213.
27. Zhang S, Takeda T, Zhu T, Chen Y, Yao X, Tanaka O, Ogihara Y. A new minor saponin from the leaves of Panax ginseng. Planta Med 1990;56:298-300.
28. 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 (Tokyo) 2001;49:442-446.
29. Qiu F, Ma ZZ, Xu S, Yao XS, Chen YJ, Che ZT. Studies on dammarane-type saponins in the flower-buds of Panax ginseng C.A. Meyer. J Asian Nat Prod Res 1998;1:119-123.
30. Tung NH, Song GY, Park YJ, Kim YH. Two new dammarane-type saponins from the leaves of Panax ginseng. Chem Pharm Bull 2009;57:1412-1414.
31. Liu GY, Li XW, Wang NB, Zhou HY, Wei W, Gui MY, Yang B, Jin YR. Three new dammarane-type triterpene saponins from the leaves of Panax ginseng C.A. Meyer. J Asian Nat Prod Res 2010;12:865-873.
32. Wu LJ, Wang LB, Gao HY, Wu B, Song XM, Tang ZS. A new compound from the leaves of Panax ginseng. Fitoterapia 2007;78:556-560.
33. Huang J, Tang XH, Ikejima T, Sun XJ, Wang XB, Xi RG, Wu LJ. A new triterpenoid from Panax ginseng exhibits cytotoxicity through p53 and the caspase signaling pathway in the HepG2 cell line. Arch Pharm Res 2008;31:323-329.
34. Tung NH, 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 (Tokyo) 2010;58:1111-1115.
35. Tung NH, Quang TH, Son JH, Koo JE, Hong HJ, Koh YS, Song GY, Kim YH. Inhibitory effect of ginsenosides from steamed ginseng-leaves and flowers on the LPS-stimulated IL-12 production in bone marrow-derived dendritic cells. Arch Pharm Res 2011;34:681-685.
36. Yoshikawa M, Sugimoto S, Nakamura S, Sakumae H, Matsuda H. Medicinal flowers. XVI. New dammaranetype triterpene tetraglycosides and gastroprotective principles from flower buds of Panax ginseng. Chem Pharm Bull (Tokyo) 2007;55:1034-1038.
37. 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 (Tokyo) 2007;55:571-576.
38. 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;20:309-314.
39. Tung NH, 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;58:868-874.
40. Zhao JM, Li N, Zhang H, Wu CF, Piao HR, Zhao YQ. Novel dammarane-type sapogenins from Panax ginseng berry and their biological activities. Bioorg Med Chem Lett 2011;21:1027-1031.
41. 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 (Tokyo) 2009;57:283-287.
42. Konno C, Sugiyama K, Kano M, Takahashi M, Hikino H. Isolation and hypoglycaemic activity of panaxans A, B, C, D and E, glycans of Panax ginseng roots. Planta Med 1984;50:434-436.
43. Konno C, Murakami M, Oshima Y, Hikino H. Isolation and hypoglycemic activity of panaxans Q, R, S, T and U, glycans of Panax ginseng roots. J Ethnopharmacol 1985;14:69-74.
44. Oshima Y, Konno C, Hikino H. Isolation and hypoglycemic activity of panaxans I, J, K and L, glycans of Panax ginseng roots. J Ethnopharmacol 1985;14:255-259.
45. Tomoda M, Takeda K, Shimizu N, Gonda R, Ohara N, Takada K, Hirabayashi K. Characterization of two acidic polysaccharides having immunological activities from the root of Panax ginseng. Biol Pharm Bull 1993;16:22-25.
46. Tomoda M, Hirabayashi K, Shimizu N, Gonda R, Ohara N, Takada K. Characterization of two novel polysaccharides having immunological activities from the root of Panax ginseng. Biol Pharm Bull 1993;16:1087-1090.
47. Matsunaga H, Katano M, Yamamoto H, Mori M, Takata K. Studies on the panaxytriol of Panax ginseng C. A. Meyer. Isolation, determination and antitumor activity. Chem Pharm Bull (Tokyo) 1989;37:1279-1281.
48. Iwabuchi H, Yoshikura M, Ikawa Y, Kamisako W. Studies on the sesquiterpenoids of Panax ginseng C. A. Meyer. Isolation and structure determination of sesquiterpene alcohols, panasinsanols A and B. Chem Pharm Bull (Tokyo) 1987;35:1975-1981.
49. Iwabuchi H, Yoshikura M, Kamisako W. Studies on the sesquiterpenoids of Panax ginseng C. A. Meyer. II. Isolation and structure determination of ginsenol, a novel sesquiterpene alcohol. Chem Pharm Bull (Tokyo) 1988;36:2447-2451.
50. Iwabuchi H, Kato N, Yoshikura M. Studies on the sesquiterpenoids of Panax ginseng C. A. Meyer. IV. Chem Pharm Bull (Tokyo) 1990;38:1405-1407.
51. Chen J, Zhao R, Zeng YM, Meng H, Zuo WJ, Li X, Wang JH. Three new triterpenoid saponins from the leaves and stems of Panax quinquefolium. J Asian Nat Prod Res 2009;11:195-201.
52. Jiang HP, Qiu YK, Cheng DR, Kang TG, Dou DQ. Structure elucidation and complete NMR spectral assignments of two new dammarane-type tetraglycosides from Panax quinquefolium. Magn Reson Chem 2008;46:786-790.
53. Li GY, Zeng YM, Meng H, Li X, Wang JH. A new triterpenoid saponin from the leaves and stems of Panax quinquefolium L. Chin Chem Lett 2009;20:1207-1210.
54. Nakamura S, Sugimoto S, Matsuda H, Yoshikawa M. Medicinal flowers. XVII. New dammarane-type triterpene glycosides from flower buds of American ginseng, Panax quinquefolium L. Chem Pharm Bull (Tokyo) 2007;55:1342-1348.
55. Wang JH, Li W, Sha Y, Tezuka Y, Kadota S, Li X. Triterpenoid saponins from leaves and stems of Panax quinquefolium L. J Asian Nat Prod Res 2001;3:123-130.
56. Yoshikawa M, Murakami T, Yashiro K, Yamahara J, Matsuda H, Saijoh R, Tanaka O. Bioactive saponins and glycosides. XI. Structures of new dammarane-type triterpene oligoglycosides, quinquenosides I, II, III, IV, and V, from American ginseng, the roots of Panax quinquefolium L. Chem Pharm Bull (Tokyo) 1998;46:647-654.
57. Du XW, Wills RB, Stuart DL. Changes in neutral and malonyl ginsenosides in American ginseng (Panax quinquefolium) during drying, storage and ethanolic extraction. Food Chem 2004;86:155-159.
58. Xie G, Plumb R, Su M, Xu Z, Zhao A, Qiu M, Long X, Liu Z, Jia W. Ultra-performance LC/TOF MS analysis of medicinal Panax herbs for metabolomic research. J Sep Sci 2008;31:1015-1026.
59. Ren G, Chen F. Degradation of ginsenosides in American ginseng (Panax quinquefolium) extracts during microwave and conventional heating. J Agric Food Chem 1999;47:1501-1505.
60. Wang CZ, Zhang B, Song WX, Wang A, Ni M, Luo X, Aung HH, Xie JT, Tong R, He TC et al. Steamed American ginseng berry: ginsenoside analyses and anticancer activities. J Agric Food Chem 2006;54:9936-9942.
61. Wang CZ, Aung HH, Ni M, Wu JA, Tong R, Wicks S, He TC, Yuan CS. Red American ginseng: ginsenoside constituents and antiproliferative activities of heat-processed Panax quinquefolius roots. Planta Med 2007;73:669-674.
62. Qiu YK, Dou DQ, Cai LP, Jiang HP, Kang TG, Yang BY, Kuang HX, Li MZ. Dammarane-type saponins from Panax quinquefolium and their inhibition activity on human breast cancer MCF-7 cells. Fitoterapia 2009;80:219-222.
63. Wang M, Guilbert LJ, Li J, Wu Y, Pang P, Basu TK, Shan JJ. A proprietary extract from North American ginseng (Panax quinquefolium) enhances IL-2 and IFN-gamma productions in murine spleen cells induced by Con-A. Int Immunopharmacol 2004;4:311-315.
64. Oshima Y, Sato K, Hikino H. Isolation and hypoglycemic activity of quinquefolans A, B, and C, glycans of Panax quinquefolium roots. J Nat Prod 1987;50:188-190.
65. Christensen LP, Jensen M, Kidmose U. Simultaneous determination of ginsenosides and polyacetylenes in American ginseng root (Panax quinquefolium L.) by highperformance liquid chromatography. J Agric Food Chem 2006;54:8995-9003.
66. Baranska M, Schulz H, Christensen LP. Structural changes of polyacetylenes in American ginseng root can be observed in situ by using Raman spectroscopy. J Agric Food Chem 2006;54:3629-3635.
67. Washida D, Kitanaka S. Determination of polyacetylenes and ginsenosides in Panax species using high performance liquid chromatography. Chem Pharm Bull (Tokyo) 2003;51:1314-1317.
68. Wang CZ, McEntee E, Wicks S, Wu JA, Yaun CS. Phytochemical and analytical studies of Panax notoginseng (Burk.) F.H. Chen. J Nat Med 2006;60:97-106.
69. Zhu S, Zou K, Fushimi H, Cai S, Komatsu K. Comparative study on triterpene saponins of ginseng drugs. Planta Med 2004;70:666-677.
70. Yoshikawa M, Morikawa T, Yashiro K, Murakami T, Matsuda H. Bioactive saponins and glycosides. XIX. Notoginseng (3): immunological adjuvant activity of notoginsenosides and related saponins: structures of notoginsenosides-L, -M, and -N from the roots of Panax notoginseng (Burk.) F. H. Chen. Chem Pharm Bull (Tokyo) 2001;49:1452-1456.
71. Yoshikawa M, Murakami T, Ueno T, Yashiro K, Hirokawa N, Murakami N, Yamahara J, Matsuda H, Saijoh R, Tanaka O. 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. Chem Pharm Bull (Tokyo) 1997;45:1039-1045.
72. Chen Y, Sorensen LK. Determination of marker constituents in radix Glycyrrhizae and radix Notoginseng by near infrared spectroscopy. Fresenius J Anal Chem 2000;367:491-496.
73. Wei JX, Wang LA, Du H, Li R. Isolation and identification of sanchinoside B1 and B2 from rootlets of Panax notoginseng (Burk.) F. H. Chen. Yao Xue Xue Bao 1985;20:288-293.
74. Wei JX, Wang JF, Chang LY, Du YC. Chemical studies of san-chi Panax notoginseng (Burk.) F. H. Chen. I. Studies on the constituents of San-Chi root hairs. Yao Xue Xue Bao 1980;15:359-364.
75. Wei JX, Liangyu C, Jufen W, Friedrichs E, Jores M, Puff H, Breitmaier E. Two new dammaran sapogenins from leaves of Panax notoginseng. Planta Med 1982;45:167-171.
76. Cui XM, Jiang ZY, Zeng J, Zhou JM, Chen JJ, Zhang XM, Xu LS, Wang Q. Two new dammarane triterpene glycosides from the rhizomes of Panax notoginseng. J Asian Nat Prod Res 2008;10:845-849.
77. Wan JB, Zhang QW, Hong SJ, Guan J, Ye WC, Li SP, Lee MY, Wang YT. 5,6-Didehydroginsenosides from the roots of Panax notoginseng. Molecules 2010;15:8169-8176.
78. Liu Y, Li J, He J, Abliz Z, Qu J, Yu S, Ma S, Liu J, Du D. Identification of new trace triterpenoid saponins from the roots of Panax notoginseng by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 2009;23:667-679.
79. Wang W, Rayburn ER, Hang J, Zhao Y, Wang H, Zhang R. Anti-lung cancer effects of novel ginsenoside 25-OCH(3)-PPD. Lung Cancer 2009;65:306-311.
80. Zhao Y, Wang W, Han L, Rayburn ER, Hill DL, Wang H, Zhang R. Isolation, structural determination, and evaluation of the biological activity of 20(S)-25-methoxyldammarane-3beta, 12beta, 20-triol [20(S)-25-OCH3PPD], a novel natural product from Panax notoginseng. Med Chem 2007;3:51-60.
81. Wang JR, Yamasaki Y, Tanaka T, Kouno I, Jiang ZH. Dammarane-type triterpene saponins from the flowers of Panax notoginseng. Molecules 2009;14:2087-2094.
82. Sun S, Wang CZ, Tone R, Li XL, Fishbein A, Wang Q, He TC, Du W, Yuan CS. Effects of steaming the root of Panax notoginseng on chemical composition and anticancer activities. Food Chem 2010;118:307-314.
83. Teng RW, Li HZ, Wang DZ, Yang CR. Hydrolytic reaction of plant extracts to generate molecular diversity: new dammarane glycosides from the mild acid hydrolysate of root saponins of Panax notoginseng. Helv Chim Acta 2004;87:1270-1278.
84. Ohtani K, Mizutani K, Hatono S, Kasai R, Sumino R, Shiota T, Ushijima M, Zhou J, Fuwa T, Tanaka O. Sanchinan-A, a reticuloendothelial system activating arabinogalactan from sanchi-ginseng (roots of Panax notoginseng). Planta Med 1987;53:166-169.
85. Choi RC, Zhu JT, Leung KW, Chu GK, Xie HQ, Chen VP, Zheng KY, Lau DT, Dong TT, Chow PC et al. A flavonol glycoside, isolated from roots of Panax notoginseng, reduces amyloid-beta-induced neurotoxicity in cultured neurons: signaling transduction and drug development for Alzheimer's disease. J Alzheimers Dis 2010;19:795-811.
86. Liu JH, Lee CS, Leung KM, Yan ZK, Shen BH, Zhao ZZ, Jiang ZH. Quantification of two polyacetylenes in Radix Ginseng and roots of related Panax species using a gas chromatography-mass spectrometric method. J Agric Food Chem 2007;55:8830-8835.
87. Chan P, Thomas GN, Tomlinson B. Protective effects of trilinolein extracted from Panax notoginseng against cardiovascular disease. Acta Pharmacol Sin 2002;23:1157-1162.
88. Kobashi K, Akao T. Relation of intestinal bacteria to pharmacological effects of glycosides. Bioscience Microflora 1997;16:1-7.
89. Kim DH. Herbal medicines are activated by intestinal microflora. Nat Prod Sci 2002;8:35-43.
90. Tawab MA, Bahr U, Karas M, Wurglics M, Schubert-Zsilavecz M. Degradation of ginsenosides in humans after oral administration. Drug Metab Dispos 2003;31:1065-1071.
91. Karikura M, Miyase T, Tanizawa H, Taniyama T, Takino Y. Studies on absorption, distribution, excretion and metabolism of ginseng saponins. VII. Comparison of the decomposition modes of ginsenoside-Rb1 and -Rb2 in the digestive tract of rats. Chem Pharm Bull (Tokyo) 1991;39:2357-2361.
92. Lee HU, Bae EA, Han MJ, Kim NJ, Kim DH. Hepatoprotective effect of ginsenoside Rb1 and compound K on tert-butyl hydroperoxide-induced liver injury. Liver Int 2005;25:1069-1073.
93. Akao T, Kida H, Kanaoka M, Hattori M, Kobashi K. Intestinal bacterial hydrolysis is required for the appearance of compound K in rat plasma after oral administration of ginsenoside Rb1 from Panax ginseng. J Pharm Pharmacol 1998;50:1155-1160.
94. Akao T, Kanaoka M, Kobashi K. Appearance of compound K, a major metabolite of ginsenoside Rb1 by intestinal bacteria, in rat plasma after oral administration: measurement of compound K by enzyme immunoassay. Biol Pharm Bull 1998;21:245-249.
95. Liu H, Yang J, Du F, Gao X, Ma X, Huang Y, Xu F, Niu W, Wang F, Mao Y et al. Absorption and disposition of ginsenosides after oral administration of Panax notoginseng extract to rats. Drug Metab Dispos 2009;37:2290-2298.
96. Shibata S. Chemistry and cancer preventing activities of ginseng saponins and some related triterpenoid compounds. J Korean Med Sci 2001;16 Suppl:S28-S37.
97. Shin JE, Park EK, Kim EJ, Hong YH, Lee KT, Kim DH. Cytotoxicity of compound K (IH-901) and ginsenoside Rh2, main biotransformants of ginseng saponins by bifidobacteria, against some tumor cells. J Ginseng Res 2003;27:129-134.
98. Choo MK, Sakurai H, Kim DH, Saiki I. A ginseng saponin metabolite suppresses tumor necrosis factor-alphapromoted metastasis by suppressing nuclear factorkappaB signaling in murine colon cancer cells. Oncol Rep 2008;19:595-600.
99. Nakata H, Kikuchi Y, Tode T, Hirata J, Kita T, Ishii K, Kudoh K, Nagata I, Shinomiya N. Inhibitory effects of ginsenoside Rh2 on tumor growth in nude mice bearing human ovarian cancer cells. Jpn J Cancer Res 1998;89:733-740.
100. Bae EA, Park SY, Kim DH. Constitutive beta-glucosidases hydrolyzing ginsenoside Rb1 and Rb2 from human intestinal bacteria. Biol Pharm Bull 2000;23:1481-1485.
101. Bae EA, Han MJ, Kim EJ, Kim DH. Transformation of ginseng saponins to ginsenoside Rh2 by acids and human intestinal bacteria and biological activities of their transformants. Arch Pharm Res 2004;27:61-67.
102. Lee SJ, Sung JH, Lee SJ, Moon CK, Lee BH. Antitumor activity of a novel ginseng saponin metabolite in human pulmonary adenocarcinoma cells resistant to cisplatin. Cancer Lett 1999;144:39-43.
103. Park EK, Shin YW, Lee HU, Kim SS, Lee YC, Lee BY, Kim DH. Inhibitory effect of ginsenoside Rb1 and compound K on NO and prostaglandin E2 biosyntheses of RAW264.7 cells induced by lipopolysaccharide. Biol Pharm Bull 2005;28:652-656.
104. Shin YW, Kim DH. Antipruritic effect of ginsenoside rb1 and compound k in scratching behavior mouse models. J Pharmacol Sci 2005;99:83-88.
105. Choo MK, Park EK, Han MJ, Kim DH. Antiallergic activity of ginseng and its ginsenosides. Planta Med 2003;69:518-522.
106. Han GC, Ko SK, Sung JH, Chung SH. Compound K enhances insulin secretion with beneficial metabolic effects in db/db mice. J Agric Food Chem 2007;55:10641-10648.
107. Kim DH, Jung JS, Moon YS, Sung JH, Suh HW, Kim YH, Song DK. Inhibition of intracerebroventricular injection stress-induced plasma corticosterone levels by intracerebroventricularly administered compound K, a ginseng saponin metabolite, in mice. Biol Pharm Bull 2003;26:1035-1038.
108. Bae EA, Kim EJ, Park JS, Kim HS, Ryu JH, Kim DH. Ginsenosides Rg3 and Rh2 inhibit the activation of AP-1 and protein kinase A pathway in lipopolysaccharide/interferon-gamma-stimulated BV-2 microglial cells. Planta Med 2006;72:627-633.
109. Park EK, Choo MK, Kim EJ, Han MJ, Kim DH. Antiallergic activity of ginsenoside Rh2. Biol Pharm Bull 2003;26:1581-1584.
110. Lee HU, Bae EA, Han MJ, Kim DH. Hepatoprotective effect of 20(S)-ginsenosides Rg3 and its metabolite 20(S) ginsenoside Rh2 on tert-butyl hydroperoxide-induced liver injury. Biol Pharm Bull 2005;28:1992-1994.
111. Trinh HT, Han SJ, Kim SW, Lee YC, Kim DH. Bifidus fermentation increases hypolipidemic and hypoglycemic effects of red ginseng. J Microbiol Biotechnol 2007;17:1127-1133.
112. Hwang JT, Kim SH, Lee MS, Kim SH, Yang HJ, Kim MJ, Kim HS, Ha J, Kim MS, Kwon DY. Anti-obesity effects of ginsenoside Rh2 are associated with the activation of AMPK signaling pathway in 3T3-L1 adipocyte. Biochem Biophys Res Commun 2007;364:1002-1008.
113. Lee WK, Kao ST, Liu IM, Cheng JT. Increase of insulin secretion by ginsenoside Rh2 to lower plasma glucose in Wistar rats. Clin Exp Pharmacol Physiol 2006;33:27-32.
114. Park EK, Choo MK, Oh JK, Ryu JH, Kim DH. Ginsenoside Rh2 reduces ischemic brain injury in rats. Biol Pharm Bull 2004;27:433-436.
115. Jung JS, Shin JA, Park EM, Lee JE, Kang YS, Min SW, Kim DH, Hyun JW, Shin CY, Kim HS. Anti-inflammatory mechanism of ginsenoside Rh1 in lipopolysaccharidestimulated microglia: critical role of the protein kinase A pathway and hemeoxygenase-1 expression. J Neurochem 2010;115:1668-1680.
116. Park EK, Choo MK, Han MJ, Kim DH. Ginsenoside Rh1 possesses antiallergic and anti-inflammatory activities. Int Arch Allergy Immunol 2004;133:113-120.
117. Lee Y, Jin Y, Lim W, Ji S, Choi S, Jang S, Lee S. A ginsenoside-Rh1, a component of ginseng saponin, activates estrogen receptor in human breast carcinoma MCF- 7 cells. J Steroid Biochem Mol Biol 2003;84:463-468.
118. Masuno H, Kitao T, Okuda H. Ginsenosides increase secretion of lipoprotein lipase by 3T3-L1 adipocytes. Biosci Biotechnol Biochem 1996;60:1962-1965.
119. Leung KW, Leung FP, Mak NK, Tombran-Tink J, Huang Y, Wong RN. Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. Br J Pharmacol 2009;156:626-637.
120. Bae EA, Shin JE, Kim DH. Metabolism of ginsenoside Re by human intestinal microflora and its estrogenic effect. Biol Pharm Bull 2005;28:1903-1908.
121. Han KL, Jung MH, Sohn JH, Hwang JK. Ginsenoside 20S-protopanaxatriol (PPT) activates peroxisome proliferator-activated receptor gamma (PPARgamma) in 3T3- L1 adipocytes. Biol Pharm Bull 2006;29:110-113.
122. Usami Y, Liu YN, Lin AS, Shibano M, Akiyama T, Itokawa H, Morris-Natschke SL, Bastow K, Kasai R, Lee KH. Antitumor agents. 261. 20(S)-protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of (1)H NMR spectra. J Nat Prod 2008;71:478-481.
123. Wang M, Guilbert LJ, Ling L, Li J, Wu Y, Xu S, Pang P, Shan JJ. Immunomodulating activity of CVT-E002, a proprietary extract from North American ginseng (Panax quinquefolium). J Pharm Pharmacol 2001;53:1515-1523.
124. Hu S, Concha C, Cooray R, Holmberg O. Ginsengenhanced oxidative and phagocytic activities of polymorphonuclear leucocytes from bovine peripheral blood and stripping milk. Vet Res 1995;26:155-161.
125. Kim JY, Germolec DR, Luster MI. Panax ginseng as a potential immunomodulator: studies in mice. Immunopharmacol Immunotoxicol 1990;12:257-276.
126. Hwang I, Ahn G, Park E, Ha D, Song JY, Jee Y. An acidic polysaccharide of Panax ginseng ameliorates experimental autoimmune encephalomyelitis and induces regulatory T cells. Immunol Lett 2011;138:169-178.
127. Shin HJ, Kim YS, Kwak YS, Song YB, Kim YS, Park JD. Enhancement of antitumor effects of paclitaxel (taxol) in combination with red ginseng acidic polysaccharide (RGAP). Planta Med 2004;70:1033-1038.
128. Baek SH, Lee JG, Park SY, Bae ON, Kim DH, Park JH. Pectic polysaccharides from Panax ginseng as the antirotavirus principals in ginseng. Biomacromolecules 2010;11:2044-2052.
129. Metabolism of ginsenosides to bioactive compounds by intestinal microflora and its industrial application. J Ginseng Res 2009;33:165-176.
130. Park CS, Yoo MH, Noh KH, Oh DK. Biotransformation of ginsenosides by hydrolyzing the sugar moieties of ginsenosides using microbial glycosidases. Appl Microbiol Biotechnol 2010;87:9-19.
131. Lee JH, Hyun YJ, Kim DH. Cloning and characterization of α-L-arabinofuranosidase and bifunctional α-L-arabinopyranosidase/β-D-galactopyranosidase from Bifidobacterium longum H-1. J Appl Microbiol 2011;111:1097-1107.
132. Noh KH, Son JW, Kim HJ, Oh DK. Ginsenoside compound K production from ginseng root extract by a thermostable beta-glycosidase from Sulfolobus solfataricus. Biosci Biotechnol Biochem 2009;73:316-321.
133. Kim BH, Lee SY, Cho HJ, You SN, Kim YJ, Park YM, Lee JK, Baik MY, Park CS, Ahn SC. Biotransformation of Korean Panax ginseng by pectinex. Biol Pharm Bull 2006;29:2472-2478.
134. Park EK, Choo MK, Oh JK, Ryu JH, Kim DH. Ginsenoside Rh2 reduces ischemic brain injury in rats. Biol Pharm Bull 2004;27:433-436.
135. Chang KH, Jee HS, Lee NK, Park SH, Lee NW, Paik HD. Optimization of the enzymatic production of 20(S) ginsenoside Rg(3) from white ginseng extract using response surface methodology. N Biotechnol 2009;26:181-186.
136. Shin HY, Lee JH, Lee JY, Han YO, Han MJ, Kim DH. Purification and characterization of ginsenoside Ra-hydrolyzing beta-D-xylosidase from Bifidobacterium breve K-110, a human intestinal anaerobic bacterium. Biol Pharm Bull 2003;26:1170-1173.
137. Yu H, Liu H, Zhang C, Tan D, Lu M, Jin F. Purification and characterization of gypenoside-alpha-L-rhamnosidase hydrolyzing gypenoside-5 into ginsenoside Rd. Process Biochem 2004;39:861-867.
138. Shin HY, Park SY, Sung JH, Kim DH. Purification and characterization of alpha-L-arabinopyranosidase and alpha-L-arabinofuranosidase from Bifidobacterium breve K-110, a human intestinal anaerobic bacterium metabolizing ginsenoside Rb2 and Rc. Appl Environ Microbiol 2003;69:7116-7123.
139. Kim SJ, Lee CM, Kim MY, Yeo YS, Yoon SH, Kang HC, Koo BS. Screening and characterization of an enzyme with beta-glucosidase activity from environmental DNA. J Microbiol Biotechnol 2007;17:905-912.
140. Zhao X, Gao L, Wang J, Bi H, Gao J, Du X, Zhou Y, Tai G. A novel ginsenoside Rb1-hydrolyzing beta-D-glucosidase from Cladosprium fulvum. Process Biochem 2009; 44:612-618.
141. Son JW, Kim HJ, Oh DK. Ginsenoside Rd production from the major ginsenoside Rb1 by beta-glucosidase from Thermus caldophilus. Biotechnol Lett 2008;30:713-716.
142. Ko SR, Suzuki Y, Suzuki K, Choi KJ, Cho BG. Marked production of ginsenosides Rd, F2, Rg3, and compound K by enzymatic method. Chem Pharm Bull (Tokyo) 2007;55:1522-1527.
143. Ko SR, Choi KJ, Suzuki K, Suzuki Y. Enzymatic preparation of ginsenosides Rg2, Rh1, and F1. Chem Pharm Bull (Tokyo) 2003;51:404-408.
144. Yan Q, Zhou W, Li X, Feng M, Zhou P. Purification method improvement and characterization of a novel ginsenoside-hydrolyzing beta-glucosidase from Paecilomyces bainier sp. 229. Biosci Biotechnol Biochem 2008;72:352-359.
145. Yan Q, Zhou XW, Zhou W, Li XW, Feng MQ, Zhou P. Purification and properties of a novel beta-glucosidase, hydrolyzing ginsenoside Rb1 to CK, from Paecilomyces bainier. J Microbiol Biotechnol 2008;18:1081-1089.
146. Park SY, Bae EA, Sung JH, Lee SK, Kim DH. Purification and characterization of ginsenoside Rb1-metabolizing beta-glucosidase from Fusobacterium K-60, a human intestinal anaerobic bacterium. Biosci Biotechnol Biochem 2001;65:1163-1169.
147. Yu H, Zhang C, Lu M, Sun F, Fu Y, Jin F. Purification and characterization of new special ginsenosidase hydrolyzing multi-glycisides of protopanaxadiol ginsenosides, ginsenosidase type I. Chem Pharm Bull (Tokyo) 2007;55:231-235.
148. Su JH, Xu JH, Lu WY, Lin GQ. Enzymatic transformation of ginsenoside Rg3 to Rh2 using newly isolated Fusarium proliferatum ECU 2042. J Mol Catal B Enzym 2006;38:113-118.
149. Bae EA, Choo MK, Park EK, Park SY, Shin HY, Kim DH. Metabolism of ginsenoside R(c) by human intestinal bacteria and its related antiallergic activity. Biol Pharm Bull 2002;25:743-747.
150. Bae EA, Shin JE, Kim DH. Metabolism of ginsenoside Re by human intestinal microflora and its estrogenic effect. Biol Pharm Bull 2005;28:1903-1908.
151. Yu H, Gong J, Zhang C, Jin F. Purification and characterization of ginsenoside-alpha-L-rhamnosidase. Chem Pharm Bull (Tokyo) 2002;50:175-178.
152. Ruan CC, Zhang H, Zhang LX, Liu Z, Sun GZ, Lei J, Qin YX, Zheng YN, Li X, Pan HY. Biotransformation of ginsenoside Rf to Rh1 by recombinant beta-glucosidase. Molecules 2009;14:2043-2048.