Four New Dammarane-Type Triterpene Saponins from the Stems and Leaves of Panax ginseng and Their Cytotoxicity on HL-60 Cells

Abstract

Four new triterpene saponins, ginsenosides Rh₁₄-Rh₁₇ (1–4), along with two known compounds, 20(S)-ginsenoside Rg₂ and dammar-(E)-20(22),24-diene-3β,6α,12β-triol, were isolated from the stems and leaves of Panax ginseng. The structures of the new compounds were elucidated as 3β,6α,12β,24ξ-tetrahydroxy-dammar-(E)-20(22),25-diene 6-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranoside (1), 3β,12β,24ξ-trihydroxy-dammar-(E)-20(22),25-diene 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranoside (2), 3β,6α,12β-trihydroxy-dammar-(E)-20(22),24-diene 3-O-β-D-glucopyranoside (3), and 3-oxo-6α,12β,20(S)-trihydroxy-dammar-24-ene 6-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranoside (4) by means of extensive spectroscopic and chemical methods, respectively. The isolated compounds were tested for in vitro cytotoxicity against HL-60 cells.

Key words

Panax ginseng - Araliaceae - dammarane triterpenoids - saponin - cytotoxicity - HL-60

References

• 1 Wang J Y, Li X G, Zheng Y N, Yang X W. Isoginsenoside-Rh₃, a new triterpenoid saponin from the fruits of Panax ginseng C. A. Mey.  J Asian Nat Prod Res. 2004;  6 289-293
• 2 Park J D, Rhee D K, Lee Y H. Biological activities and chemistry of saponins from Panax ginseng.  Phytochem Rev. 2005;  4 159-175
• 3 Chinese Pharmacopoeia Commission .Pharmacopoeia of the People's Republic of China. Vol. 1. Beijing: People's Medical Publishing House; 2005: 71-73
• 4 Wang L B, Wu Z H, Gao H Y, Huang J, Sun B H, Wu L J. A new compound with cytotoxic activities from the leaves of Panax ginseng C. A. Meyer.  Chin Chem Lett. 2008;  19 837-840
• 5 Tung N H, Song G Y, Park Y J, Kim Y H. Two new dammarane-type saponins from the leaves of Panax ginseng.  Chem Pharm Bull. 2009;  57 1412-1414
• 6 Liu G Y, Li X W, Wang N B, Zhou H Y, Wei W, Gui M Y, Yang B, Jin Y R. Three new dammarane-type triterpene saponins from the leaves of Panax ginseng C.A. Meyer.  J Asian Nat Prod Res. 2010;  12 865-873
• 7 Yang X W, Li L Y, Tian J M, Zhang Z W, Ye J M, Gu W F. Ginsenoside-Rg₆, a novel triterpenoid saponin from the stem-leaves of Panax ginseng C. A. Mey.  Chin Chem Lett. 2000;  11 909-912
• 8 Yang X W, Gui F J, Tian J M, Li L Y, Jin Y. Pharmacokinetics of ginsenoside-Rg₂ in rats.  Chin Pharmacol Bull. 2009;  25 967-970
• 9 Yang X W. Complete assignment of ¹H and ¹³C-NMR chemical shifts of 20(R)-ginsenoside Rg₂ and 20(S)-ginsenoside Rg₂.  Chin J Magn Reson. 2000;  17 9-15
• 10 Wu L J, Wang L B, Gao H Y, Wu B, Song X M, Tang Z S. A new compound from the leaves of Panax ginseng.  Fitoterapia. 2007;  78 556-560
• 11 Dou D Q, Chen Y J, Liang L H, Pang F G, Shimizu N, Takeda T. Six new dammarane-type triterpene saponins from the leaves of Panax ginseng.  Chem Pharm Bull. 2001;  49 442-446
• 12 Yoshikawa M, Morikawa T, Kashima Y, Ninomiya K, Matsuda H. Structures of new dammarane-type triterpene saponins from the flower buds of Panax notoginseng and hepatoprotective effects of principal ginseng saponins.  J Nat Prod. 2003;  66 922-927
• 13 Liao P Y, Wang D, Zhang Y J, Yang C R. Dammarane-type glycosides from steamed notoginseng.  J Agric Food Chem. 2008;  56 1751-1756
• 14 Baek N I, Kim D S, Lee Y H, Park J D, Lee C B, Kim S I. Ginsenoside Rh₄, A genuine dammarane glycoside from Korean red ginseng.  Planta Med. 1996;  62 86-87
• 15 Kim S I, Park J H, Ryu J H, Park J D, Lee Y H, Park J H, Kim T H, Baek N I. Ginsenoside Rg₅, a genuine dammarane glycoside from Korean red ginseng.  Arch Pharm Res. 1996;  19 551-553
• 16 Teng R W, Li H Z, Wang D Z, He Y N, Yang C R. NMR complete assignments of three protopanaxadiol monodesmosides.  Chin J Magn Reson. 2000;  17 461-468
• 17 Tanaka O. Application of ¹³C-nuclear magnetic resonance spectrometry to structural studies on glycosides: saponins of Panax spp. and natural sweet glycosides.  Yakugaku Zasshi. 1985;  105 323-351
• 18 Chen G T, Yang M, Song Y, Lu Z Q, Zhang J Q, Huang H L, Wu L J, Guo D A. Microbial transformation of ginsenoside Rb₁ by Acremonium strictum.  Appl Microbiol Biotechnol. 2008;  77 1345-1350
• 19 Chong M W K, Gu K D, Lam P K S, Yang M, Fong W F. Study on the cytotoxicity of microcystin-LR on cultured cells.  Chemosphere. 2000;  41 143-147