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Effective Purification of Ginsenosides from Cultured Wild Ginseng Roots, Red Ginseng, and White Ginseng with Macroporous Resins

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Huayue Li at Ocean University of China
Huayue Li
Jae-Hwa Lee
Jae-Hwa Lee
Jae-Hwa Lee
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Jong Myung Ha at Silla University
Jong Myung Ha
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This study was aimed (i) to develop an effective method for the purification of ginsenosides for industrial use and (ii) to compare the distribution of ginsenosides in cultured wild ginseng roots (adventitious root culture of Panax ginseng) with those of red ginseng (steamed ginseng) and white ginseng (air-dried ginseng). The crude extracts of cultured wild ginseng roots, red ginseng, and white ginseng were obtained by using a 75% ethanol extraction combined with ultrasonication. This was followed sequentially by AB-8 macroporous adsorption chromatography, Amberlite IRA 900 Cl anion-exchange chromatography, and Amberlite XAD16 adsorption chromatography for further purification. The contents of total ginsenosides were increased from 4.1%, 12.1%, and 11.3% in the crude extracts of cultured wild ginseng roots, red ginseng, and white ginseng to 79.4%, 71.7%, and 72.5% in the final products, respectively. HPLC analysis demonstrated that ginsenosides in cultured wild ginseng roots were distributed in a different ratio compared with red ginseng and white ginseng.
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J. Microbiol. Biotechnol. (2008), 18(11), 1789–1791
doi: 10.4014/jmb.0800.192
First published online 8 July 2008
Effective Purification of Ginsenosides from Cultured Wild Ginseng Roots,
Red Ginseng, and White Ginseng with Macroporous Resins
Li, Huayue, Jae-Hwa Lee, and Jong-Myung Ha*
Department of Pharmaceutical Engineering, College of Medical Life Science, Silla University, Busan 617-736, Korea
Received: March 9, 2008 / Accepted: April 22, 2008
This study was aimed (i) to develop an effective method
for the purification of ginsenosides for industrial use and
(ii) to compare the distribution of ginsenosides in cultured
wild ginseng roots (adventitious root culture of Panax
ginseng) with those of red ginseng (steamed ginseng) and
white ginseng (air-dried ginseng). The crude extracts of
cultured wild ginseng roots, red ginseng, and white ginseng
were obtained by using a 75% ethanol extraction combined
with ultrasonication. This was followed sequentially by
AB-8 macroporous adsorption chromatography, Amberlite
IRA 900 Cl anion-exchange chromatography, and Amberlite
XAD16 adsorption chromatography for further purification.
The contents of total ginsenosides were increased from 4.1%,
12.1%, and 11.3% in the crude extracts of cultured wild
ginseng roots, red ginseng, and white ginseng to 79.4%,
71.7%, and 72.5% in the final products, respectively. HPLC
analysis demonstrated that ginsenosides in cultured wild
ginseng roots were distributed in a different ratio compared
with red ginseng and white ginseng.
Keywords: Ginsenoside, purification, macroporous resin, HPLC,
cultured wild ginseng roots
Ginseng (Panax ginseng, C.A. Meyer) has been used as a
tonic, antifatigue, sedative, and antigastric ulcer drug for
thousands of years. Recently, many studies have suggested
that its pharmacological effects are mainly due to ginseng
saponins [5, 14]. However, it takes several years to cultivate
ginseng in fields and also needs very sophisticated care
because its growth conditions (i.e., soil, climate, and
pathogenesis) are very difficult to control. For these reasons,
low yields and high costs hamper efforts to meet the
demand of increasing markets. In general, cultured wild
ginseng roots (adventitious root culture of Panax ginseng)
are easily obtained by using a plant cell culture technique
for the production of ginseng and its active ingredient,
ginsenosides, rather than natural cultivation. With the cell
culture technique, fastidious and complicated conditions for
the production of ginseng and ginsenosides can be overcome
and optimized. Although many attempts have been made to
isolate ginseng saponins [8, 9], these were good only
for separation of each single ginsenoside from the total
ginsenosides products. Prior to the process, large amounts
of total pure ginsenosides should be obtained for its latter
separating process and bioassay. Generally, separation of
the ginsenosides was usually performed by using organic
solvents [12], which are not suitable for use in food or
medicine. There is an alternative purification method to
use adsorbents such as silica [6] and Diaion HP 20 [7, 11],
but this method also needs to use toxic organic solvents for
the extraction of crude ginsenosides. In addition, the
absorbents have poor specificity to select ginsenosides with
low efficiency. Thus, a selective and high-yield purification
method for ginsenosides needs to be developed. In this
study, three different macroporous resins (AB-8, IRA 900
Cl, and XAD 16) were used to separate total ginsenosides
from cultured wild ginseng roots (CWG, adventitious root
culture of Panax ginseng), red ginseng (RG, steamed ginseng)
*Corresponding author
Phone: 82-51-999-5467; Fax: 82-51-999-5636;
E-mail: jmha@silla.ac.kr
Fig. 1. Structures of ginsenosides from Panax ginseng.
Glc: glucose; Rha: rhamnose; Ara(f): arabinose in furanose form; Ara(p):
arabinose in pyranose form.
1790 Li et al.
and white ginseng (WG, air-dried ginseng). In addition, ten
ginsenosides (Rb1, Rb2, Rc, Rd, Re, Rf, Rh1, Rg1, Rg2, and
Rg3) (Fig. 1) were quantitatively compared among three
kinds of ginseng products by HPLC analysis.
Ten g of each ground sample (CWG, RG, and WG) was
extracted with 200 ml of 75% ethanol in an ultrasonic bath for
120 min at 39oC. Then, the concentrated extracts (40 ml)
were passed through an AB-8 polar column (bed volume,
80 ml) to eliminate water, soluble impurities at the flow
rate of 1 BV (bed volume)/h and the adsorbed ginsenosides
were eluted with 3 BV of 70% ethanol (v/v) at 2 BV/h. The
eluent was applied onto the Amberlite IRA 900 Cl strong base
anion-exchange column at the flow rate of 1 BV/h to remove
the pigments and loaded onto the Amberlite XAD 16 column
to get rid of nonpolar substances. The final resulting eluent
was collected and evaporated to yield dried powders. The
purity of the ginsenosides was estimated by using ginsenoside
Re as a calibration standard [1]. A good linear relationship
was obtained in the range of 0.005 to 0.03 mg/ml, and the
regression equation was: y=30.376x
-
0.0258 (R2=0.9983,
n=5), where y represents the absorbance at 544 nm, x the
concentration of total ginsenosides (mg/ml). Analysis of
single ginsenoside content was performed on an HPLC
system with a reversed-phase column (Zorbax Bonus-RP
4.6 mm×150 mm, 3.5 µm).
It has been known that macroporous resins are widely
used in medicine manufacturing and in extraction of active
ingredients in natural plants such as vitexin [2], vanillin [15],
arabinogalactan [4], scutellarin [3], flavone compounds
[10], etc. As the macroporous resin has a lot of advantages
of nontoxicity, good specificity, easy operation, low cost,
and easy regeneration of resin, it can be a powerful method
for industrial use instead of toxic organic solvents. Hence,
here we also tried to develop the purification method to
obtain high levels of yield and purity of ginsenosides from
cultured wild ginseng roots, red ginseng, and white ginseng.
As is shown in Table 1, 3.12±0.14 g, 3.72±0.37 g, and
3.50±0.22 g of crude ethanol extracts were obtained from each
10 g of CWG, RG, and WG, respectively. However, the total
ginsenosides content of each crude extract was only 4.0%,
12.1%, and 11.3%. After purification with the three
macroporous resins, the purity of the ginsenosides increased
to 79.4%, 71.7%, and 72.5% for CWG, RG, and WG,
respectively, indicating that the purification steps used in
this study significantly improved the purity of the
ginsenosides in each product.
Under the chromatographic conditions used in this study,
all ten calibration curves exhibited good linear regressions
(data not shown). Standard and representative chromatograms
of purified ginsenosides products for CWG, RG, and WG
were compared to be shown in Figs. 2A
-
2D. CWG contained
similar ginsenoside types with RG and WG, but they were
distributed in different ratios compared with the other two
ginseng products (Figs. 2B
-
2D). Some unknown small
Fig. 2. HPLC chromatograms of (A) mixed standards (Rb , Rb ,
Rc, Rd, Re, Rf, Rh , Rg , Rg , and Rg ); purified ginsenosides
products of (B) CWG, (C) WG, and (D) RG. HPLC was performed
on a Zorbax Bonus-RP column (4.6 mm×150 mm, 3.5 µm).
The binary gradient elution system consisted of water (A) and acetonitrile (B)
and separation was achieved using the following gradient: 0
-
30 min, 20% B;
30
-
48 min, 20
-
40% B; 48
-
60 min, 40
-
45% B; 60
-
72 min, 45
-
55% B. The
column temperature was kept constant at 35 C. The flow-rate was 1 ml/min
and injection volume was 10 µl for the standard solution (0.5 mg/ml) and 20 µl
for the samples (1 mg/ml). The UV detection wavelength was set at 203 nm. 1:
Rg ; 2: Re; 3: Rf; 4: Rb ; 5: Rc; 6: Rb ; 7: Rg ; 8: Rh ; 9: Rd; 10: Rg .
Tabl e 1 . Yield and purity of total ginsenosides from 10 g of
ground ginseng (CWG: cultured wild ginseng roots; RG: red
ginseng; WG: white ginseng).
Yield (g) Purity (%)
Crude ethanol extracts CWG 3.12±0.14 04.0±0.8
RG 3.72±0.37 12.1±1.2
WG 3.50±0.22 11.3±0.9
Purified ginsenosides CWG 0.14±0.05 79.4±1.3
products RG 0.46±0.04 71.7±0.9
WG 0.39±0.02 72.5±1.5
EFFECTIVE PURIFICATION OF GINSENOSIDES WITH MACROPOROUS RESINS 1791
peaks observed in Figs. 2B
-
2D indicated that there are
still some uninvestigated minor ginsenosides containing in
each ginsenosides product. As shown in Table 2, the
content of protopanaxadiol-type saponins (Rb1, Rb2, Rc, Rd,
Rg3) was higher than that of protopanaxatriol-type ones (Re,
Rf, Rg1, Rg2, Rh1) in CWG and RG, whereas the contents
were opposite in the case of WG. This result was inconsistent
with the previous data reported by Wan et al. [13] that WG
contained more protopanaxadiol-type saponins. One of the
possible reasons for such a different result is that ginsengs
cultivated in different areas might accumulate different
ratios of the ginsenosides. The ratio of Rb1/Rg1, two major
ginsenosides representing protopanaxadiol and protopanaxatriol,
for CWG, RG, and WG were 2.90, 1.33, and 0.67,
respectively. The Rb1 content was higher than Rg1 both in
CWG and RG; however, the difference was much more
significant in CWG. The Rg1/Re ratio of CWG, which
contained more Re (95.1±0.4 µg/mg) than Rg1 (54.3±
0.4 µg/mg), was contrary with those of the other two
ginseng products. The Rd content in CWG (74.1±0.9 µg/
mg) was about seven times and twelve times more than
that in RG (10.6±0.8 µg/mg) and WG (6.1±0.5 µg/mg),
respectively. In addition, Rg3, a kind of minor ginsenoside,
was found both in CWG and RG, but not in WG.
In conclusion, the purification of ginsenosides using three
macroporous resins (AB-8, IRA 900 Cl, and XAD 16)
significantly increased the purity of the total ginsenosides.
In addition, the contents of each investigated ginsenoside in
cultured wild ginseng roots, red ginseng, and white ginseng
were quite different. These results assist the development of a
new ginsenosides purification method and provide a possibility
of high-quality but low-price ginsenosides products. Further
study on how to improve the efficiency of purification of
ginsenosides, and on the relations between ginsenosides
distribution and their biological activities, should be undertaken.
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Tabl e 2 . Contents of ten investigated ginsenosides in three purified ginsenosides products.
Origins Protopanaxadiol (µg/mg) Protopanaxatriol (µg/mg) Rb /Rg
Rb Rb Rc Rd Rg Re Rf Rg Rg Rh
CWG 157.7±0.7 76.7±2.3 78.5±0.5 74.1±0.9
-
095.1±0.4 54.6±7.8 054.3±0.4 8.0±1.7
-
2.90
RG 129.4±1.5 40.0±0.7 58.1±0.2 10.6±0.8
-
059.0±0.9 22.6±5.7 097.4±0.6 4.1±1.2 4.3±1.1 1.33
WG 102.7±1.3 28.3±0.6 50.0±0.5 06.1±0.5
-
106.1±1.7 26.2±2.9 153.1±0.8 2.8±0.9
-
0.67
Contents=mean±SD (n=3).
Too low to be measured.
Not detected.
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Article
  • Mar 2020
In this paper, four types of middle‐pressure chromatogram isolated gels are evaluated for adsorption/desorption characteristics of ginsenosides from Panax ginseng. Among them, SP207SS and SP2MGS were selected for dynamic investigations based on their static adsorption/desorption capacity of total ginsenoside. Their adsorption kinetics was better explained by pseudo‐second‐order model and isotherms were preferably fitted to Langmuir model. Dynamic breakthrough experiments indicated an optimum sample loading speed of 4BV/h for either SP207SS or SP2MGS. Desorption speed was determined to be 2BV/h according to desorption amount of total ginsenoside in their effluents. Eight ginsenosides were identified and quantified by HPLC‐TQ‐MS in total ginsenoside extract and different fractions during stepwise dynamic elution. For SP207SS, 27.62% of loaded ginsenosides was detected in 40% ethanol fraction, while 59.12% of them were found in 60% ethanol fraction. As on SP2MGS, the number went to 53.71% and 44.43% respectively. Recovery rate of ginsenosides were calculated to 78.65% for SP207SS and 89.53% for SP2MGS. Intriguingly, content of Rg1 and Re in 40% ethanol fraction from SP207SS became 20.1 and 18.6 times higher than that in total ginsenoside extract by one step elution, which could be leveraged for the facile enrichment of these two ginsenosides from natural sources. This article is protected by copyright. All rights reserved
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A Growth Inhibition Effect of Saponin from Red Ginseng on Some Pathogenic Microorganisms
Article
Full-text available
  • Sep 2006
  • Ginseng Res
Saponin isolated from red ginseng was added to cultures of Staphylococcus aureus and Candida albicans in order to investigate saponin's influence on the growth of some pathogenic bacteria and yeasts. S. aureus and C. albicans were incubated at 38^{\circ}C\;and\;28^{\circ}C for 5 days with 100 rpm after addition of 0.013, 0.125, 0.500 and 1.000% (w/v, final concentration) of saponin, respectively. After incubated for 1 day, 2 days or 5 days, pH and viable cell counts of the cultures were investigated. The both of pH of S. aureus and C. albicans were decreased in concentration-dependent manner. Viable cell counts after incubation of 5 days were 1.0\;{\times}\;10^8,\;9.4\;{\times}\;10^7,\;1.0\;{\times}\;10^3 and 0 CFU/ml, respectively, when compared with 1.8{\times}10^8\;CFU/ml of saponin non-treated group. Especially, 1.0% concentration of saponin inhibited completely the growth of S. aureus. While, viable cell count in C. albicans somewhat lower values than that of saponin non-treated group, but the values not significant. These results suggest that ginseng saponin inhibit the growth of S. aureus in a concentration-dependent manner, but not the growth of C. albicans.
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Recovery of Vanillin from Aqueous Solutions using Macroporous Adsorption Resins
Article
Full-text available
  • Jan 2008
A simple method for recovery of dissolved vanillin from aqueous solutions by the adsorption–regeneration technique has been developed. Three macroporous adsorption resins with crosslinked-polystyrene framework were NKA-2, S-8 and H103, respectively. Static equilibrium adsorption studies were used for comparing the adsorption capacities of the three resins. The results showed that H103 resin had the best adsorption capacity because of its large and nonpolar surface areas. The effects of pH, temperature and salt concentration on the adsorption capacity of H103 were investigated. The results revealed that the resin had a maximum adsorption capacity, 416mg/g (vanillin/resin) in acidic condition when the molecule of vanillin is neutral. Furthermore, its adsorption capacity increased with the increase of temperature and salt concentration. The mass transfer zone motion model was used for analyzing the fixed bed adsorption. H103 resin had a shorter mass transfer zone of 24.7cm and both NKA-2 and S-8 were higher than 30cm in the experiment conditions. More than 95.6% of adsorbed vanillin can be recovered by use of 3–5 bed volumes of absolute ethanol. The resin can be used repeatedly by simple regeneration and its adsorption capacity was almost unchangeable.
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Separation and purification of Arabinogalactan obtained from Larix gmelinii by macroporous resin adsorption
Article
  • Mar 2007
Arabinogalactan (AG) obtained from Larix gmelinii R. was purified with the method of macroporous resin adsorption. Effects of various parameters on the adsorption, including adsorption time and temperature, the concentration and the dosage of raw AG, the reused numbers of resin, were investigated. The effect of purification was tested through the removal rate of impurity and the contents of AG and impurity. The optimal condition was determined as follows: adsorbed at 30°C for 2 h with the concentration of raw AG <0.1 g·mL−1 and its dosage < 7 mL, the dose of resin was 3 g and reused for 4 times. On the basis of these, macroporous resin column was used for AG purification. The result showed that the AG yield could reach 68.28% with sugar content of 95.02%. The analysis of IR and UV showed that the effect of macroporous resin characteristics on the purification of AG was significant. The obtained product had the same functional groups with standard sample.
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High-performance thin-layer chromatographic determination of six major ginsenosides in Panax ginseng
Article
  • Mar 2000
  • J CHROMATOGR A
A densitometric determination of six major ginsenosides in Panax ginseng, separated by high-performance thin-layer chromatography (HPTLC), was optimized. Simple extraction and clean-up methods of the target constituents and the development of standardized conditions of chromatoplates with a quaternary-solvents system allowed an efficient saponins recovery from the plant material and their selective separation. After exposure of the chromatograms to thionyl chloride vapors and further heating, stable reaction products of ginsenosides, which showed absorption maxima at lambda=275 nm as well as a fluorescence (lambda(excitation)=366 nm, lambda(emission)=400 nm), allowed the application of a sensitive and reproducible method for their simultaneous determination. The method was validated by spiking the ginseng extracts with pure standards.
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Wild Ginseng Grows in Myanmar
Article
  • Jul 2003
Ginseng, the underground parts of plants of Panax species, has been used in oriental traditional medicine for centuries. Unfortunately, because of extensive exploitation over thousands of years, the natural source of these species has been almost exhausted. Recently, we have found a wild ginseng growing in Myanmar. Here, by a combination of chemical composition study and gene sequence analysis, we unambiguously demonstrate that the wild ginseng is actually P. zingiberensis, commonly known as ginger ginseng. This ginseng was an indigenous to the southwestern China. However, now it is seriously threatened to brink of extinction and is put on the highest level of protection in China. Therefore, an appropriate protection measure is highly recommended to preserve this valuable resource, since this Myanmar ginseng might turn out to be the last P. zingiberensis, which could ever be seen in the planet.
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High-performance liquid chromatographic method with quantitative comparisons of whole chromatograms of raw and steamed Panax notoginseng
Article
  • Dec 2004
  • J CHROMATOGR A
A high-performance liquid chromatographic (HPLC) method coupled with chromatographic pattern matching was developed to differentiate whole chromatograms of raw and steamed Panax notoginseng objectively and quantitatively. The major peaks differentiating chromatograms of raw and steamed samples were also identified for the first time in this herb. The raw and steamed P. notoginseng roots and its products were successfully differentiated. The quantitative differences between the chromatograms were correlated to the duration of steaming. Chromatographic pattern matching allows rapid, simple, automated, and quantitative comparisons of complex chromatograms. It is a useful tool in ensuring safety and quality of herbal products.
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Simultaneous quantification of six major active saponins of Panax notoginseng by high-performance liquid chromatography-UV method
Article
  • Jul 2005
  • J PHARMACEUT BIOMED
A simple, sensitive and specific high-performance liquid chromatography-UV (HPLC-UV) method has been developed for the first time to simultaneously quantify the six major active saponins of Panax notoginseng, namely notoginsenoside R1, ginsenoside Rg1, Rb1, Rg2, Rh1 and Rd. Astragaloside IV is used as the internal standard. This HPLC assay was performed on a reversed-phase C18 column with gradient elution of acetonitrile and 0.01% formic acid in 30 min. The method provided good reproducibility and sensitivity for the quantification of six saponins with overall intra- and inter-day precision and accuracy of less than 4.0% and higher than 90%, respectively. This assay is successfully applied to the determination of the six saponins in 23 notoginseng samples. The results indicated that the developed HPLC assay can be readily utilized as a quality control method for P. notoginseng.
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Effects of ginseng saponins isolated from Red Ginseng roots on burn wound healing in mice
Article
  • Aug 2006
We recently demonstrated that ginsenoside Rb 1 (C 54 H 92 O 23 , molecular weight 1108) isolated from ginseng, when intravenously infused into rats with permanent middle cerebral artery occlusion, reduced cerebral infarct volume and ameliorated place navigation disability of the animals, through an anti‐apoptotic action and possibly promotion of vascular regeneration. To investigate the ginsenoside Rb 1 ‐mediated vascular regeneration in vivo in a more easily accessible experimental systems, we made a burn wound on the backs of mice and topically applied either Vaseline (vehicle) alone or Vaseline containing low doses of ginsenoside Rb 1 to the wound. Surprisingly, we found that ginsenoside Rb 1 at low concentrations (100 pg g ⁻¹ , 1 pg g ⁻¹ and 10 fg g ⁻¹ ointment) exhibited the strongest burn wound‐healing action. Furthermore, ginsenoside Rb 1 (100 fg–1 ng per wound) increased neovascularization in the surrounding tissue and production of vascular endothelial growth factor (VEGF) and interleukin (IL)‐1 β from the burn wound, compared to those mice with burn wounds treated with vehicle alone. In human keratinocyte cultures (HaCaT cells), ginsenoside Rb 1 (100 fg ml ⁻¹ to 1 ng ml ⁻¹ ) enhanced VEGF production induced by IL‐1 β and expression of hypoxia‐inducible factor (HIF)‐1 α . These findings suggest that the promotion of burn wound healing by ginsenoside Rb 1 might be due to the promotion of angiogenesis during skin wound repair via the stimulation of VEGF production, through the increase of HIF‐1 α expression in keratinocytes, and due to the elevation of IL‐1 β resulting from the macrophage accumulation in the burn wound. British Journal of Pharmacology (2006) 148 , 860–870. doi: 10.1038/sj.bjp.0706794
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Preparative separation of vitexin and isovitexin from pigeonpea extracts with macroporous resins
Article
  • Jan 2007
  • J CHROMATOGR A
Vitexin and isovitexin are a pair of isomeric compounds known as the major constituents in pigeonpea leaves and possess various pharmacological activities. In the present study, the preparative separation of vitexin and isovitexin with macroporous resins (Nankai Hecheng S & T, Tianjin, China) was studied. The performance and adsorption characteristics of eight macroporous resins including ADS-5, ADS-7, ADS-8, ADS-11, ADS-17, ADS-21, ADS-31 and ADS-F8 have been evaluated. The research results indicate that ADS-5 resin is most appropriate for the separation of vitexin and isovitexin. Langmuir and Freundlich isotherms were used to describe the interactions between solutes and resin at different temperatures, and the equilibrium experimental data were well fitted to the two isotherms. Column packed with ADS-5 resin was used to perform dynamic adsorption and desorption tests to optimize the separation process. The optimum parameters for adsorption were as follows: the concentration of vitexin and isovitexin in sample solution: 0.22 and 0.40mg/mL, respectively, processing volume: 3 BV, flow rate: 1mL/min, pH 4, temperature: 25 degrees C; for desorption: ethanol-water (40:60, v/v), 5 BV as an eluent, flow rate: 1mL/min. After one run treatment with ADS-5 resin, the contents of vitexin and isovitexin were increased 4.07-fold and 11.52-fold from 0.86%, 1.53% to 3.50% and 17.63%, the recovery yields were 65.03% and 73.99%, respectively. In conclusion, the preparative separation of vitexin and isovitexin can be easily and effectively achieved via adsorption and desorption on ADS-5 resin, and the method can be referenced for the separation of other flavone C-glucosides from herbal materials.
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