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Progress in Chemistry 2020, Vol. 32 Issue (2/3): 239-248 DOI: 10.7536/PC190814 Previous Articles   Next Articles

Sample Pretreatment, Analysis and Detection of Ginsenosides

Zhihua Song1,**(), Shenghong Li3, Gangqiang Yang1, Na Zhou2, Lingxin Chen2,**()   

  1. 1. Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, School of Pharmacy, Yantai University, Yantai 264005, China
    2. CAS Key Laboratory of Coastal Environmental Processes and Ecological Remediation, Yantai Institute of Coastal Zone Research(YIC), Chinese Academy of Sciences(CAS), Shandong Provincial Key Laboratory of Coastal Environmental Processes, Yantai 264003, China
    3. CAS Key Laboratory of Separation Sciences for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
  • Received: Online: Published:
  • Contact: Zhihua Song, Lingxin Chen
  • About author:
    ** e-mail: (Zhihua Song);
    (Lingxin Chen)
  • Supported by:
    Key Research Project of Yantai City(2018ZHGY085); National Demonstration Center for Experimental Pharmacy Education(Yantai University)()
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Ginsenosides are an important kind of active ingredients in Panax genus and can be classified into four main types: the protopanaxadiols(PPD), protopanaxatriols(PPT), oleanolic acids(OA) and ocotillol type(OT). Recently, more than 620 kinds of these compounds have been isolated. Their chemical structures are similar but have quite different medicinal functions. It is of vital importance to develop simple and facile sample pretreatment methods and detection techniques to detect the content of ginsenosides in complex matrix. This review includes many kinds of sample pretreatment methods(such as liquid phase extraction, and solid phase extraction) and detection methods(such as high performance liquid chromatography, ultra-performance liquid chromatography, thin layer chromatography, and gas chromatography), etc., summarizes the sensitivity and recovery of various methods, and reviews the advantages and disadvantages of each method and its research progress.

Key words: ginsenosides, sample pretreatment, analysis methods
Table 1 Four types of common ginsenosides:(a) 20(s)-PPD,(b) 20(s)-PPT,(c) OA,(d) 24(R)-OT[13]. Copyright 2000 American Chemical Society
(a) ginsenoside R1 R2 formula M.W.
Rb1 -glc[2→1]glc -glc[6→1]glc C54H92O23 1108
Rb2 -glc[2→1]glc -glc[6→1]ara(p) C53H90O22 1078
Rc -glc[2→1]glc -glc[6→1]ara(f) C53H90O22 1078
Rd -glc[2→1]glc -glc C48H82O18 946
(b) ginsenoside R1 R2 formula M.W.
Rg1 -glc -glc C42H72O14 800
Re -glc[2→1]rha -glc C48H82O18 946
Rf -glc[2→1]glc -H C42H72O14 800
(c) ginsenoside R1 R2 formula M.W.
Ro -glcUA[2→1]glc -glc C48H76O19 956
(d) pseudoginsenoside R formula M.W.
F11 -glc[2→1]rha C42H72O14 800
Table 2 Sample pretreatment methods for ginsenosides
Sample pretreatment methods Principles Advantages Disadvantages
Solvent extraction method Microwave assisted extraction(MAE) Cell walls of the Chinese traditional medicine are disrupted by the microwave with energy of 300 MHz~300 GHz, and then the extracting rate is increased. Convenient operation, short extraction time, high extraction yield, less solvent consumption, and low cost[24, 25]. Some heat-sensitive
compounds are easy to be destroyed.
Ultrasonic assisted extraction(UAE) The disruption of cell walls, reduction of particle-size and enhancing mass transfer of the cell contents are caused by cavitation bubble collapse, mechanical and thermal effects. Highly efficient, low consumption of solvent, fast(tens minutes), mild conditions(20~30 ℃), simple and low cost[26]. Low degree of automation and difficult to be used on-line.
Accelerated solvent extraction(ASE) ASE is carried out in closed container with a high pressure and a temperature above the boiling point of organic solvent. The extraction rate increases with the increase of pressure and temperature. Fast(a few minutes to ten minutes), save solvent, realize automation easily. Some heat-sensitive
compounds are easy to be destroyed; the instruments are expensive; and operation skills are hard to master.
Sub-and supercritical fluid extraction The extraction process proceeds by using sub-and supercritical fluids near the critical point of temperature and pressure with the good properties of high-density, low-viscosity, and high-permeability. Non-toxic and safe, no organic solvent residual, environment friendly, low energy cost [27]. The instrument is expensive
due to high pressure
resistant.
Enzymatic dissociation method Active ingredients can beextracted from plant tissues by using suitable enzymes(cellulase, amylase, etc.) under mild conditions[28]. Furthermore, the fragmentation of cell walls will be accelerated with the increase of the pressure(100~600 MPa) [29]. Efficient and has great potential in extraction of active ingredients from traditional Chinese medicine. Susceptible to external
conditions.
Solid phase extraction (SPE) The ginsenoside compounds and impurities are separated by adsorbents according to the difference in adsorption. Simple, low cost and wide
range ofapplication.		 Large amount of organic reagents consumption, only suitable for pretreatment of small batches of samples.
Table 3 The application of liquid chromatography for analysis of active compounds in Chinese herbs
Analyte Matrix Sample
pretreatment		 Column and temperature Mobile phases and detection Recovery(%) LOD Ref
Re, Rh1, Rg2,
Rg1, Rf		 White ginseng, red ginseng, American ginseng, and ginseng. Extracted by methanol Shiseido UG 80 Capcell Pak
NH2 column
(250 × 4.6 mm
i.d., 5 μm), 25 ℃		 0~3 min, 89% A; 3~25 min, 89%→84% A; 25~30 min, 84%→82% A; 30~35 min, 82%→76% A; 35~40 min,89% A.
A:acetonitrile; B water. UV:203 nm		 95.31%~103.85% 0.0047 ~
0.225
(mg·L-1)		 12
20 (S)-Rh1, 20
(R)-Rh1, Rg6,
F4, Rk3, 20(S)-Rg3, 20(R)-Rg3, Rk1, Rg5		 Roots of P. quinquefolius L. Reflux extraction by water and
methanol		 Acchrom Technologies ODS-C18 type column(250 ×4.6 mm i.d., 5 μm), 30 ℃. 0~10 min, 33% B; 10~15 min, 33%→40% B; 15~40 min, 40%→60% B; 40~70 min, 60% B.
A: water; B: acetonitrile. HPLC-UV: 203 nm.
HPLC-ESI-MS		 97.97%~103.24% 0.18~
0.45
(μg·mL-1)		 24
ginsenosides Rb1, Rc, Rb2, Rb3;
notoginsenosides Fc, Fe, Fd		 Panax notoginseng leaves Rxtracted by methanol Agilent Zorbax ODS C8 column(250 × 4.6 mm
i.d.,5 μm),
35 ℃		 0~5 min, 15%→30% B; 5~15 min, 30%→32% B; 15~35 min, 32%→32% B; 35~45 min, 32%→45% B; 45~60 min, 45%→50% B. A: water; B: acetonitrile.
HPLC-UV: 203 nm		 98.7%~106.1% 98 (ng) 40
Ginsenoside Rg1,
Ginsenoside Rb1,
Ginsenoside Rc,
Ginsenoside Rd,
Ginsenoside Re,
Ginsenoside Rf,
Ginsenoside Rg3,
Ginsenoside Rh1,
Ginsenoside Rb2,
Ginsenoside Rb3		 Ginsenosides in chronic
heart failure(CHF) rats		 Solid-phase extraction(SPE) ACQUITY UPLC?? HSS T3 column(100 × 2.1 mm i.d.,
1.8 μm),
40 ℃		 0~1 min, 30%→35% B; 1.0~5.0 min, 35%→38% B; 5.0~5.5 min, 38%→45% B; 5.5~6.0 min, 45%→80% B; 6.0~7.0 min, 80%→90% B; 7.0~7.5 min, 90%→30% B; 7.5~8.0 min, 30%→30% B. A: water with 0.1% formic acid; B: acetonitrile.
UFLC-MS/MS		 60%~105% - 42
Ginsenoside Rg1,
Ginsenoside Re,
Ginsenoside Rb1		 Panax quinquefolii Radix Reflux extraction by water-saturated
n-butanol		 Venusil XBP
C18 column
(250 × 4.6 mm i.d., 5 μm),
30 ℃.		 0.01~25 min, 19%→20% A;
25.01~60 min, 20%→40% A;
60.01~80 min, 40.1%→100% A.
A: acetonitrile; B: 0.1%
phosphoric acid solution.
UV: 203 nm		 88.61%~94.29% 0.066~
0.400
(μg·mL-1)		 55
notoginsenoside R1,
ginsenoside Rg1,
ginsenoside Rb1,
astragaloside Ⅳ,
ginsenoside Rd		 Qishen Yiqi
Dripping Pills(QYDP)		 liquid-liquid Extraction using water-
saturated n-butanol		 Acquity UPLC HSS T3 column (100 × 2.1 mm i.d., 5 μm), 30 ℃ 0~1 min, 83% A; 1~14 min, 83%→56%; 14~15 min, 56% A. A: water containing 0.1% formic acid; B: acetonitrile. UPLC-ELSD 96.87%~99.97% 2.36~
7.68
(μg·mL-1)		 57
Analyte Matrix Sample
pretreatment		 Column and temperature Mobile phases and detection Recovery(%) LOD Ref
G-Ra1, G-Ra2,
G-Rb1, G-Rb2,
G-Rb3, G-Rc,
G-Rd, G-Re,
G-Re4, G-Rf,
G-Rg1, G-Rg2,
G-Ro, G-Rs2,
G-RoMe, 20-Glc-
G-Rf, Ma-G-Rb2,
NG-R1, NG-R2		 Roots and
rhizomes of
Panax ginseng samples.		 Extracted by 70% aqueous MeOH solutions Diamonsil ODS C18 column
(250 × 4.6 mm i.d., 5 μm), room temperature		 0~20 min, 10%→20% A; 20~30 min, 20%→22% A; 30~40 min, 22%→31%A; 40~75 min, 31%→33% A; 75~80 min, 33%→40% A; 80~90 min, 40%→50% A; 90~100 min, 50%→60% A; 100~110 min, 60%→70% A. Flow rate: 0~32 min, 0.8 mL/min; 32.1~110 min, 0.5 mL/min.
A: MeCN; B: MeCN: H2O: 0.1% formic acid aqueous solution(5∶90∶8; v/v/v)
HPLC-ESI-MS		 94.87%~102.45% 0.159~
9.052 (ng)		 58
N-R1, G-Rg1,
G-Re, G-Rf,
G-F3, G-Rg2,
G-Rh1, G-Rb1,
G-Ro, G-Rc,
G-Rb2, G-Rb3,
CS-IV, CS-Iva,
G-Rd, G-Rg3		 Panax japonicas(PJ), Panax japonicus var. major(PM), and Panax zingiberensis (PZ) Extracted by 60% aqueous methanol solutions Waters C18
column(150×3.9 mm i.d., 4.6 μm), room
temperature		 0~3 min, 20%→23% A; 3~8 min, 30%→35% A; 8~15 min, 35% A; 15~20 min, 35%→60% A; 20~22 min, 60%→80% A; 22~24 min, 80%→95% A; 24~25 min, 95%→20% A.
A: acetonitrile; B: 0.05% formic acid aqueous solution.
HPLC-ESI-MS/MS		 99.25%~104.10% 0.13~
2.22
(ng·mL-1)		 59
ginsenosides Rg1, 20(S)-Rg2, Re, 20(S)-Rh, Rb1, Rb2, Rd Tissue extracts from the root and rhizome of Panax ginseng C.A. Mey. Extracted by methanol Waters C18
column(100 mm ×2.1 mm i.d., 1.7 μm), room temperature ~20 ℃.		 0~3 min, 10%→20% B; 3~25 min, 20%→38% B; 25~30 min, 38%→85% B; 30~30.1 min, 85%→100% B; 30.1~32 min, 100% B; 32~32.1 min 100%→10% B. A: formic acid aqueous solution; B: acetonitrile containing 0.1% formic acid.
UPLC-QTOF-MS		 - 6.08~
108.72
(ng·mL-1)		 60
Rg1 and
its metabolites		 Sprague-
Dawley rat
bile, urine,
and feces		 Extracted by methanol Shim-Pack XR-ODS Ⅱ(75 × 2 mm, 2.3 μm) column, 40 ℃. 0~7 min, 22%→80% B; 7~7.01 min, 80%→22%; 7.01~10 min, 22%→22% B.
A: 0.05% formic acid aqueous solution; B: 0.05% formic acid in acetonitrile.
HPLC-MS/MS		 Rg1, ginsenoside Rh1(Rh1), and protopanaxatriol(Ppt) in bile, urine, and feces ≥70%. The fecal excretion recoveries of Rg1, Rh1, and Ppt, 22.19%~ 40.11%. Rg1 in bile, 6.88%; Rh1 and Rg1in Urinary excretion 0.04%~0.09%. - 61
Rg1, Re, Rf,
Rg2, Rb1, Rc,
Rb2, Rd		 Kang’ai
injection		 Aqueous two-
phase system
based Deep
eutectic solvent
and K2HPO4
solution		 Agilent Zorbax SB-C18 column(250×4.6 mm i.d., 5 μm),
30 ℃		 0~34 min, 19.2% A; 34~35 min, 19.2%→28.0% A; 35~48 min, 28.0% A; 48~56 min, 28.5% A; 56~72 min, 36.0% A. A: acetonitrile; B: 0.1% phosphoric acid aqueous solution. HPLC-DAD: 203 nm 92.7%~110.8% 0.3~1.5
(μg·mL-1)		 62
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