1.Studies on saponin composition of Schefflera sp3
Journal of Medicinal Materials - Hanoi 2004;9(2):46-50
By NAMBA ‘weight method from leaf, root and stem of Schefflera sp. triterpen saponins were qualified. By thin layer chromatography, 11 stains of saponin were determined on leaf, 7 on stem and root with the quantities of 3,66%, 0,93%, 0,77% in absolutely dried leaf,stem and root, respectively. By thin layer chromatography 4 stains of total sapogenins of the leaf and 2 genins were isolated on column chromatography. Fusion points,chromatography,IR spectrum, 1H-NMR,13 C-NMR spectrography,DEPT,HMQC and HMBC had showed oleanolic and hederagenin in the structure of 2 genins
Saponins
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Araliaceae
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Sapogenins
2.Adjuvant effects of saponins on animal immune responses.
Zahid Iqbal RAJPUT ; Song-hua HU ; Chen-wen XIAO ; Abdullah G ARIJO
Journal of Zhejiang University. Science. B 2007;8(3):153-161
Vaccines require optimal adjuvants including immunopotentiator and delivery systems to offer long term protection from infectious diseases in animals and man. Initially it was believed that adjuvants are responsible for promoting strong and sustainable antibody responses. Now it has been shown that adjuvants influence the isotype and avidity of antibody and also affect the properties of cell-mediated immunity. Mostly oil emulsions, lipopolysaccharides, polymers, saponins, liposomes, cytokines, ISCOMs (immunostimulating complexes), Freund's complete adjuvant, Freund's incomplete adjuvant, alums, bacterial toxins etc., are common adjuvants under investigation. Saponin based adjuvants have the ability to stimulate the cell mediated immune system as well as to enhance antibody production and have the advantage that only a low dose is needed for adjuvant activity. In the present study the importance of adjuvants, their role and the effect of saponin in immune system is reviewed.
Adjuvants, Immunologic
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pharmacology
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Animals
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Astragalus Plant
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ISCOMs
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pharmacology
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Immune System
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drug effects
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Oleanolic Acid
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analogs & derivatives
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Panax
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Sapogenins
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Saponins
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pharmacology
3.Protopanaxadiol-type ginsenoside hydrolases and their application in the preparation of ginsenoside Compound K: a review.
Wenhua YANG ; Qiuya GU ; Xiaobin YU
Chinese Journal of Biotechnology 2023;39(3):978-992
Ginsenoside Compound K (CK) has anti-cancer and anti-inflammatory pharmacological activities. It has not been isolated from natural ginseng and is mainly prepared by deglycosylation of protopanaxadiol. Compared with the traditional physicochemical preparation methods, the preparation of CK by hydrolysis with protopanaxadiol-type (PPD-type) ginsenoside hydrolases has the advantages of high specificity, environmental-friendliness, high efficiency and high stability. In this review, the PPD-type ginsenoside hydrolases were classified into three categories based on the differences in the glycosyl-linked carbon atoms of the hydrolase action. It was found that most of the hydrolases that could prepare CK were PPD-type ginsenoside hydrolase type Ⅲ. In addition, the applications of hydrolases in the preparation of CK were summarized and evaluated to facilitate large-scale preparation of CK and its development in the food and pharmaceutical industries.
Ginsenosides/pharmacology*
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Hydrolases
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Sapogenins/chemistry*
4.Chemical constituents of Oxytropis chiliophylla.
Shu-ying YAO ; Yun-Bao MA ; Ya TANG ; Ji-jun CHEN ; Xue-mei ZHANG
China Journal of Chinese Materia Medica 2007;32(16):1660-1662
OBJECTIVETo study the chemical constituents of Oxytropis chiliophylla.
METHODThe air-dried whole plants of O. chiliophylla were extracted with EtOH (90%) three times at room temperature. The compounds were isolated by silica-gel, polyamide, C-18 and Sphadex LH -20 columns. The structures were identified based on spectral analysis.
RESULT8 compounds were isolated from O. chiliophylla and identified as azukisapogenol (1), (22E, 24R) -24-methyl-5alpha-cholesta-7, 22-diene-3beta, 5alpha, 6beta-triol (2), apigein (3), 3', 4'-dimethoxy-quercetin-3-O-beta-D-galactopyranoside (4), 7, 3', 4'-trimethoxy-quercetin-3-O-alpha-L-rhamopyranosyl-(1-->2)-beta-D-glucopyranoside (5), (2S, 3S, 4R)-N-[(R)-2'-hydroxytetracosanoyl]-1, 3, 4-trihydroxy-2-amino-octadeca-6-ene (6), beta-sitosterol (7), daucosterol (8).
CONCLUSIONAll the compounds were isolated from O. chiliophylla for the first time.
Oxytropis ; chemistry ; Plants, Medicinal ; chemistry ; Sapogenins ; chemistry ; isolation & purification ; Sitosterols ; chemistry ; isolation & purification
5.New dammarane type triterpene with cyclization at the side chain from oxidative alkaline-degradation products of PQS.
Yuan HUANG ; Ning LI ; Xian LI ; Lu-Sha GAO ; Da-Li MENG
Acta Pharmaceutica Sinica 2008;43(3):277-280
To study the oxidative alkaline-degradation products of PQS (Panax quinquefolium saponin), two compounds were isolated from the crude product of oxidative alkaline-degradation by silica gel column chromatography, Sephadex LH-20 column chromatography and recrystallized methods. On the basis of spectroscopic analysis, their structures were established as (12R, 20S, 24R)-20, 24; 12, 24-diepoxy-24-deisopropyl-dammarane-3beta-ol (1) and (20S, 24R)-20, 24-epoxydammarane-3beta3, 12beta, 25-triol (2). Compounds 1 and 2, dammarane type triterpene with cyclization at the side chain, were obtained for the first time from alkaline-degradation products of total ginsenosides of Panax quinquefolium L., compound 1 is a new compound.
Cyclization
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Oxidation-Reduction
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Panax
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chemistry
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Sapogenins
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chemistry
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Saponins
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chemistry
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Steroids
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chemistry
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Triterpenes
;
chemistry
6.Biotransformation in vivo/vitro and bioactive properties of rare ginsenoside IH901.
Yuxing TONG ; Zhizhong ZHENG ; Qingxuan TONG ; Yi LIN ; Yanlin MING
Chinese Journal of Biotechnology 2012;28(6):684-695
Recent metabolomics research revealed a new ginseng ginsenoside IH901 that is synthesized by intestinal microbial transformation in oral administration of ginseng. IH901 shows various biological activities, including anti-tumor, anti-inflammatory, anti-diabetic, and anti-aging. In recent years, great effort has been made to prepare IH901 by microbial and enzymatic transformation in a large scale. In this paper, we reviewed the biotransformation pathways both in vivo and in vitro and bioactive properties of rare ginsenoside IH901.
Biotransformation
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Ginsenosides
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metabolism
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pharmacokinetics
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Humans
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Intestines
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metabolism
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microbiology
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Panax
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chemistry
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Sapogenins
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metabolism
7.Inhibitory Effects of Ginsenoside Metabolites, Compound K and Protopanaxatriol, on GABAC Receptor-Mediated Ion Currents.
Byung Hwan LEE ; Sung Hee HWANG ; Sun Hye CHOI ; Hyeon Joong KIM ; Joon Hee LEE ; Sang Mok LEE ; Yun Gyong AHN ; Seung Yeol NAH
The Korean Journal of Physiology and Pharmacology 2013;17(2):127-132
Ginsenosides, one of the active ingredients of Panax ginseng, show various pharmacological and physiological effects, and they are converted into compound K (CK) or protopanaxatriol (M4) by intestinal microorganisms. CK is a metabolite derived from protopanaxadiol (PD) ginsenosides, whereas M4 is a metabolite derived from protopanaxatriol (PT) ginsenosides. The gamma-aminobutyric acid receptorC (GABAC) is primarily expressed in retinal bipolar cells and several regions of the brain. However, little is known of the effects of ginsenoside metabolites on GABAC receptor channel activity. In the present study, we examined the effects of CK and M4 on the activity of human recombinant GABAC receptor (rho1) channels expressed in Xenopus oocytes by using a 2-electrode voltage clamp technique. In oocytes expressing GABAC receptor cRNA, we found that CK or M4 alone had no effect in oocytes. However, co-application of either CK or M4 with GABA inhibited the GABA-induced inward peak current (IGABA). Interestingly, pre-application of M4 inhibited IGABA more potently than CK in a dose-dependent and reversible manner. The half-inhibitory concentration (IC50) values of CK and M4 were 52.1+/-2.3 and 45.7+/-3.9 microM, respectively. Inhibition of IGABA by CK and M4 was voltage-independent and non-competitive. This study implies that ginsenoside metabolites may regulate GABAC receptor channel activity in the brain, including in the eyes.
Brain
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Eye
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gamma-Aminobutyric Acid
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Ginsenosides
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Humans
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Oocytes
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Panax
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Retinal Bipolar Cells
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RNA, Complementary
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Sapogenins
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Xenopus
8.Study on transformation rules of terrestrosin D in course of Tribuli Fructus stir-frying based on simulated processing technology.
Rui YUAN ; Tong SU ; Chao ZHANG ; Xiao SONG ; Yao-Hui YUAN ; Rui-Teng LI ; Yi-Jing LIU
China Journal of Chinese Materia Medica 2019;44(14):3049-3054
The contents of terrestrosin D and hecogenin from Tribuli Fructus were determined before and after stir-frying. The results showed that the content of terrestrosin D was decreased significantly,and the content of hecogenin was increased significantly after such processing. In order to verify the inference that terrestrosin D was converted to hecogenin by stir-frying,the quantitative variation rules of terrestrosin D and hecogenin were studied by simulated processing technology,and the simulated processing product of terrestrosin D was qualitatively characterized by ultra performance liquid chromatography/time of flight mass spectrometry( UPLC-TOF/MS) to clarify its transformation process during stir-frying. The results showed that the content of terrestrosin D was decreased significantly at first and then a platform stage appeared with the prolongation of processing time at a certain temperature. Raising the stir-frying temperature could further decrease the content of terrestrosin D and delay the time that the platform stage appeared. When the processing was simulated at higher temperatures( 220 ℃ and 240 ℃),the content of hecogenin was increased gradually with the increase of processing temperature and the prolongation of processing time. In the process of stir-frying,the deglycosylation reaction of terrestrosin D to hecogenin was not completed in one step. The deglycosylation reaction occurred first at the end of the sugar chain,and then other glycosyl units in the sugar chain were sequentially removed from the outside to the inside to finally form the hecogenin. This study provides a basis for further revealing the detoxification mechanism of stir-fried Tribuli Fructus.
Chromatography, Liquid
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Fruit
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chemistry
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Hot Temperature
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Phytochemicals
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analysis
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Sapogenins
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analysis
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Tandem Mass Spectrometry
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Zygophyllaceae
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chemistry
9.Determination of content and entrapment efficiency of 20 (S)-protopanaxadiol in pharmacosomes by RP-HPLC method.
Meihua HAN ; Jing CHEN ; Shilin CHEN ; Xiangtao WANG
China Journal of Chinese Materia Medica 2009;34(9):1082-1085
OBJECTIVETo establish a RP-HPLC method for content and entrapment efficiency of 20 (S)-protopanaxadiol in pharmacosomes.
METHODThe separation was performed with a COSMOSIL 5 C18-MS-II column (4.6 mm x 250 mm, 5 mmicrom) using methanol-water (95:5) as the mobile phase and detected at 203 nm. The flow rate was 1.0 mL x min(-1) and 50 microL sample solution was injected for each time.
RESULTThe calibration curve was linear within the range 0.1-0.5 mg x mL(-1) (r = 0. 9999) , the intra-day RSD and inter-day RSD were less than 2% and the average recovery was between 101.44%-103.11% (n = 3).
CONCLUSIONThe method is simple, accurate, sensitive and applicable for determination of content and entrapment efficiency of 20 (S)-protopanaxadiol pharmacosomes.
Calibration ; Chromatography, High Pressure Liquid ; Drugs, Chinese Herbal ; chemistry ; Panax ; chemistry ; Reproducibility of Results ; Sapogenins ; analysis ; isolation & purification
10.Chemistry and Cancer Preventing Activities of Ginseng Saponins and Some Related Triterpenoid Compounds.
Journal of Korean Medical Science 2001;16(Suppl):S28-S37
More than 25 dammarane-type tetracyclic triterpenoid saponins have been isolated from ginseng, the root and rhizome of Panax ginseng C.A. Meyer (Araliaceae). The genuine sapogenins of those saponins, 20(S)-protopanaxa-diol and -triol, were identified as 20(S) 12beta-hydroxy-and 20(S) 6alpha,12beta-dihydroxy-dammarenediol-II, respectively. There are two types of preparations from ginseng: white ginseng prepared by drying after peelling off and red ginseng prepared by steaming and drying. Some partly deglycosylated saponins such as ginsenoside Rh-1, Rh-2, and Rg-3 are obtained from red ginseng as artifacts produced during steaming. Several workers studied the metabolic transformation by human intestinal bacteria after oral administration of ginsenoside Rb-1 and Rb-2 and found that the stepwise deglyco-sylation yielded compound K and finally 20(S)-protopanaxadiol. Ginsenoside Rg-1 was converted into 20(S)-protopanaxatriol via ginsenoside Rh-1. Yun et al. in Korea conducted the epidemiological case-control studies of ginseng and suggested its cancer preventing activities. Kitagawa et al. demonstrated in vitro that ginsenosides, especially 20(R)-ginsenoside Rg-3, specifically inhibited cancer cell invasion and metastasis. Azuma et al. found that ginsenoside Rb-2 inhibited tumor angiogenesis, and Kikuchi et al. reported that ginsenoside Rh-2 inhibited the human ovarian cancer growth in nude mice. Recently, ginsenoside Rg-3 was produced as an anti-angiogenic anti-cancer drug in China. The aforementioned reports suggest that less glycosylated protopanaxadiol derivatives are effective in cancer prevention. Apart from Ginseng tetracyclic triterpenoid saponins, some oleanane-type pentacyclic triterpenoid compounds showed the anti-carcinogenic activity in the two-stage anti-cancer-promotion experiments in vitro and in vivo.
Animal
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Antineoplastic Agents, Phytogenic/*therapeutic use
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Human
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Molecular Structure
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Neoplasms/*prevention & control
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*Panax/chemistry
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Sapogenins/chemistry
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Saponins/chemistry/isolation & purification/metabolism/*pharmacology
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Triterpenes/chemistry/*pharmacology