Re-evaluation of physicochemical and NMR data of triol ginsenosides Re, Rf, Rg2, and 20-gluco-Rf from Panax ginseng roots

Cho, Jin-Gyeong (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University)
In, Seo-Ji (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University)
Jung, Ye-Jin (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University)
Cha, Byeong-Ju (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University)
Lee, Dae-Young (Department of Herbal Crop Research, National Institute of Horticultural and Herbal Science, Rural Development Administration)
Kim, Yong-Bum (Technology Services Division, National Institute of Horticultural and Herbal Science, Rural Development Administration)
Yeom, Myeonghun (Amorepacific Corporation Research and Development Center)
Baek, Nam-In (Graduate School of Biotechnology and Department of Oriental Medicinal Materials and Processing, Kyung Hee University)

published in 2014. 4. 15

Abstracts

Ginseng roots were extracted with aqueous methanol, and extracts were suspended in water and extracted successively with ethyl acetate and n-butanol. Column chromatography using the n-butanol fraction yielded four purified triol ginseng saponins: the ginsenosides Re, Rf, Rg2, and 20-gluco-Rf. The physicochemical, spectroscopic, and chromatographic characteristics of the ginsenosides were measured and compared with reports from the literature. For spectroscopic analysis, two-dimensional nuclear magnetic resonance (NMR) methods such as $^1H$-$^1H$ correlation spectroscopy, nuclear Overhauser effect spectroscopy, heteronuclear single quantum correlation, and heteronuclear multiple bond connectivity were employed to identify exact peak assignments. Some peak assignments for previously published $^1H$-and $^{13}C$-NMR spectra were found to be inaccurate. This study reports the complete NMR assignment of 20-gluco-Rf for the first time.

Keyword

fast atom bombardment/MS
HPLC
NMR
Panax ginseng
triol ginsenoside

Chemical Compound (All 9)

Ginsenoside Rf (C₄₂H₇₂O₁₄)

Notoginsenoside R1 (C₄₇H₈₀O₁₈)

(2R,4aS,6aS,6aR,14aS,14bR)-10-hydroxy-11-keto-2,4a,6a,6a,9,14a-hexamethyl-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid | (2R,4aS,6aS,6aR,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid (C₂₉H₃₈O₄)

(5S,8R,9R,10S,13R,14R,17R)-17-[(1R)-1,5-dimethylhexyl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene | (5S,8R,9R,10S,13R,14R,17R)-4,4,8,10,14-pentamethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene | dammarane (C₃₀H₅₄)

(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid | oleanolic acid (C₃₀H₄₈O₃)

(4aS,6aR,6aR,6bR,8aR,12aS,14aR,14bS)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicene (C₃₀H₅₂)

beta-D-glucopyranose (C₆H₁₂O₆)

panaxatriol (ginsenosied Re) (C₄₈H₈₂O₁₈)

panaxatriol (ginsenosied Rg_1) (C₄₂H₇₂O₁₄)

Analytical Information

Analytical Information of the Articles
IPC	A61K 36/258, C07J 51/00, G01N 24/08
Analytical Keyword	Panax ginseng; triol ginsenoside; ginsenoside Re; ginsenoside Rf; ginsenoside Rg2; MeOH=methanol; extract; water; EtOAc=ethyl acetate; n-butanol=n-BuOH; 20-gluco-Rf; two-dimensional nuclear magnetic resonance=NMR
Herb keywrd	Panax ginseng
Etc. keywrd	triol ginsenoside; ginsenoside Re; ginsenoside Rf; ginsenoside Rg2; MeOH=methanol; extract; water; EtOAc=ethyl acetate; n-butanol=n-BuOH; 20-gluco-Rf; two-dimensional nuclear magnetic resonance=NMR

Published Information

Cover

Published Information of the Articles
Country	kor
Publisher	The Korean Society of Ginseng
KJTK Publish Information	Volume 8. 2014. 12. 31
TKOI It is persistent identifier of content provided by the Korean Traditional Knowledge Portal. It is used as a permanent access route to each content. Syntax: http://tkoi.koreantk.com/[TKOI] Example: http://tkoi.koreantk.com/TKOI:KTKP-TSS-0000045749	TKOI:KTKP-TSS-0000225206