Multicomponent assessment and ginsenoside conversions of Panax quinquefolium L. roots before and after steaming by HPLC-MSn

Abstract

BackgroundThe structural conversions in ginsenosides induced by steaming or heating or acidic condition could improve red ginseng bioactivities significantly. In this paper, the chemical transformations of red American ginseng from fresh Panax quinquefolium L. under steaming were investigated, and the possible mechanisms were discussed.MethodsA method with reversed-phase high-performance liquid chromatography coupled with linear ion trap mass spectrometry (HPLC-MSn)-equipped electrospray ionization ion source was developed for structural analysis and quantitation of ginsenosides in dried and red American ginseng.ResultsIn total, 59 ginsenosides of protopanaxadiol, protopanaxatriol, oleanane, and ocotillol types were identified in American ginseng before and after steaming process by matching the molecular weight and/or comparing MSn fragmentation with that of standards and/or known published compounds, and some of them were determined to be disappeared or newly generated under different steaming time and temperature. The specific fragments of each aglycone-type ginsenosides were determined as well as aglycone hydrated and dehydrated ones. The mechanisms were deduced as hydrolysis, hydration, dehydration, and isomerization of neutral and acidic ginsenosides. Furthermore, the relative peak areas of detected compounds were calculated based on peak areas ratio.ConclusionThe multicomponent assessment of American ginseng was conducted by HPLC-MSn. The result is expected to provide possibility for holistic evaluation of the processing procedures of red American ginseng and a scientific basis for the usage of American ginseng in prescription.

Phytochemical analysis of Panax species: a review

“…Then, the loss of glycosylation moiety at C-20 and C-3 of Rd through hydrolysis generated ginsenosides 20( R / S )-Rg 3 and F 2 . 20( R / S )-Rh 2 , Rk 1 , and Rg 5 under the reaction conditions gradually increased [ 44 , 74 , 75 , [77] , [78] , [79] , [80] , [81] ]. Interestingly, ginsenosides Rk 1 and Rg 5 were deduced to 20( R / S )-Rg 3 by Δ20(21) and Δ20(22) dehydration at C-20.…”

“…Ginsenosides Rk 1 and Rg 5 are hydrolyzed to generate Rk 2 and Rh 3 by loss of a glycosylation moiety at C-20 [ 74 , 75 , 80 , 81 ]. Protopanaxatriol including ginsenosides Re and Rg 1 produced 20( R / S )-Rg 2 , F 1 , Rg 6 , 20( R / S )-Rh 1 , and Rg 4 through hydrolysis of a glycosylation moiety at C-20 and C-6 when the creaming with high-temperature and long-time shown in Scheme 2 [ 74 , 75 , 77 , 80 , 81 ]. Specifically, ginsenosides 20( R / S )-Rf 2 was deduced by C-24 and C-25 hydration of Rg 2 [ 81 ].…”

Inhibitory Effects of Ginsenoside Ro on the Growth of B16F10 Melanoma via Its Metabolites

“…In fact, Ro can also convert to IVa, R1, and E in vitro. After ginseng is steamed at 120 °C for 6 h, Ro levels sharply decrease, and the contents of IVa, R1, and E increase [76]. The improvement of biological activity after ginseng is steamed is possibly attributed to this form of composition transformation.…”

Optimization of flash extraction, separation of ginsenosides, identification by HPLC-FT-ICR-MS and determination of rare ginsenosides in mountain cultivated ginseng

“…In the Chinese pharmacopoeia and many existing ginseng standards, the extraction of ginseng requires a long time of heating with some ginsenosides may be transformed. 13 Therefore, there is an urgent need for a room temperature and fast extraction method in order to better extract and distinguish MCG and CG.…”