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Found 1 structure.
Displayed structure 1
| b-D-Glcp-(1-3)-Protopanaxadiol20s | Show graphically |
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Structure type: monomer
Trivial name: ginsenoside Rh2, (20S)-ginsenoside Rh2, ginsenoside
Compound class: saponin glycoside, glycoside, triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
This study examined the biotransformation pathway of ginsenoside Rb1 by the fungus Esteya vermicola CNU 120806. Ginsenosides Rb1 and Rd were extracted from the root of Panax ginseng. Liquid fermentation and purified enzyme hydrolysis were employed to investigate the biotransformation of ginsenoside Rb1. The metabolites were identified and confirmed using NMR analysis as gypenoside XVII and gypenoside LXXV. A mole yield of 95.4% gypenoside LXXV was obtained by enzymatic conversion (pH 5.0, temperature 50°C). Ginsenoside Rd was used to verify the transformation pathway under the same reaction condition. The product Compound K (mole yield 49.6%) proved a consecutive hydrolyses occurred at the C-3 position of ginsenoside Rb1. Conclusions: Strain CNU 120806 showed a high degree of specific β-glucosidase activity to convert ginsenosides Rb1 and Rd to gypenoside LXXV and Compound K, respectively. The maximal activity of the purified glucosidase for ginsenosides transformation occurred at 50°C and pH 5.0. Compared with its activity against pNPG (100%), the β-glucosidase exhibited quite lower level of activity against other aryl-glycosides. Enzymatic hydrolysate, gypenoside LXXV and Compound K were produced by consecutive hydrolyses of the terminal and inner glucopyranosyl moieties at the C-3 carbon of ginsenoside Rb1 and Rd, giving the pathway: ginsenoside Rb1 → gypenoside XVII → gypenoside LXXV; ginsenoside Rd → F2 → Compound K, but did not hydrolyse the 20-C, β-(1-6)-glucoside of ginsenoside Rb1 and Rd. Significance and Impact of the Study: The results showed an important practical application on the preparation of gypenoside LXXV. Additionally, this study for the first time provided a high efficient preparation method for gypenoside LXXV without further conversion, which also gives rise to a potential commercial enzyme application.
β-glucosidase, compound K, Esteya vermicola CNU120806, ginsenoside Rb 1, gypenoside LXXV, gypenoside XVII
NCBI PubMed ID: 22805203Ginsenoside Rh1 or Rh2 differentiated B16 melanoma or F9 teratocarnoma to phenotypic normal melanocyte-like cells or parietal endoderm-like cells. Ginsenoside Rh3 and Rh4 were recently isolated from Panax ginseng, but their biochemical and pharmacological effects remain unidentified. The present study investigated whether the ginsenoside Rh group (G-Rh1, -Rh2, -Rh3 and -Rh4) having similar structures induce differentiation of HL-60 cells and whether protein kinase C (PKC) is involved in differentiation by ginsenoside. Differentiation was assessed by Wright-Giemsa stain and nitroblue tetrazolium reduction. G-Rh2 and G-Rh3 induced differentiation of HL-60 cells into morphologically and functionally granulocytes but G-Rh1 and G-Rh4 did not. G-Rh2 and G-Rh3 arrested the cell cycle at the GI/S phase, consistent with the ability to induce differentiation in a decreasing order of retinoic acid > GRh2>G-Rh3. During differentiation by G-Rh2, Ca2+/phospholipid-dependent PKC activity was increased in both the cytosol and total cell extract and 2+ Ca/phospholipid-dependent phosphorylation of 38 and 200 kDa endogenous proteins increased, while phosphorylation of 60, 64, 66 and 97 kDa proteins was Ca2+/phospholipid-independent. When cytosolic PKC isoforms were analyzed by immunoblotting, no significant change was observed in the α level, however, the immunoreactive 60 kDa band of a similar mass to the PKC catalytic fragment appeared following treatment with G-Rh2. The β isoform was gradually increased with prolonged treatment. The γ isoform was not detected in the cytosol of untreated cells, whereas a small amount was detected 5 days after treatment. It is concluded that G-Rh2 and G-Rh3 can induce differentiation of HL-60 cells into granulocytes and modulation of PKC isoform levels may contribute to differentiation of HL-60 cells by G-Rh2.
differentiation, protein kinase C, ginsenoside, HL-60 cells
NCBI PubMed ID: 9611775The adaptogen concept is examined from an historical, biological, chemical, pharmacological and medical perspective using a wide variety of primary and secondary literature. The definition of an adaptogen first proposed by Soviet scientists in the late 1950s, namely that an adaptogen is any substance that exerts effects on both sick and healthy individuals by 'correcting' any dysfunction(s) without producing unwanted side effects, was used as a point of departure. We attempted to identify critically what an adaptogen supposedly does and to determine whether the word embodies in and of itself any concept(s) acceptable to western conventional (allopathic) medicine. Special attention was paid to the reported pharmacological effects of the 'adaptogen-containing plant' Eleutherococcus senticosus (Rupr. & Maxim.) Maxim. (Araliaceae), referred to by some as 'Siberian ginseng', and to its secondary chemical composition. We conclude that so far as specific pharmacological activities are concerned there are a number of valid arguments for equating the action of so-called adaptogens with those of medicinal agents that have activities as anti-oxidants, and/or anti-cancerogenic, immunomodulatory and hypocholesteroletic as well as hypoglycemic and choleretic action. However, 'adaptogens' and 'anti-oxidants' etc. also show significant dissimilarities and these are discussed. Significantly, the classical definition of an adaptogen has much in common with views currently being invoked to describe and explain the 'placebo effect'. Nevertheless, the chemistry of the secondary compounds of Eleutherococcus isolated thus far and their pharmacological effects support our hypothesis that the reported beneficial effects of adaptogens derive from their capacity to exert protective and/or inhibitory action against free radicals. An inventory of the secondary substances contained in Eleutherococcus discloses a potential for a wide range of activities reported from work on cultured cell lines, small laboratory animals and human subjects. Much of the cited work (although not all) has been published in peer-reviewed journals. Six compounds show various levels of activity as anti-oxidants, four show anti-cancer action, three show hypocholesterolemic activity, two show immunostimulatory effects, one has choleretic activity and one has the ability to decrease/moderate insulin levels, one has activity as a radioprotectant, one shows anti-inflammatory and anti-pyretic activities and yet another has shown activity as an antibacterial agent. Some of the compounds show more than one pharmacological effect and some show similar effects although they belong to different chemical classes. Clearly, Eleutherococcus contains pharmacologically active compounds but one wishes that the term adaptogen could be dropped from the literature because it is vague and conveys no insights into the mechanism(s) of action. If a precise action can be attributed to it, then the exact term for said action should obviously be used; if not, we strongly urge that generalities be avoided. Also, comparison of Eleutherococcus with the more familiar Panax ginseng C.A. Meyer (Araliaceae), 'true ginseng' has underscored that they differ considerably chemically and pharmacologically and cannot be justifiably considered as mutually interchangeable. Accordingly, we recommend that the designation 'Siberian ginseng' be dropped and be replaced with 'Eleutherococcus'. In the case of both Eleutherococcus and true ginseng, problems inherent in herbal preparation use include inconsistencies not only in terms of indications for use, but in the nomenclature of constituent chemical compounds, standardization, dosage and product labeling. Finally, our re-examination and fresh interpretation of the literature on Eleutherococcus and comparison with true ginseng shows that the potential for a scientifically more complete and defensible exploitation of these plants will be better served by investigating and considering them in a context that consciously ignores the fact that the word ‘adaptogen’ was ever invented.
saponins, Panax ginseng, lignans, adaptogen, adaptogenic activity, Eleutherococcus senticosus, anti-cancer agents, anti-oxidants, placebo effect, true ginseng, ‘Siberian ginseng’
NCBI PubMed ID: 10996277A liquid chromatographic method was developed and validated for the determination of ginsenosides in Panax ginseng roots by using evaporative light-scattering detection. Eighteen ginsenosides were separated on a reversed-phase C18 column with water-ammonium acetate-acetonitrile as the mobile phase. The method is suitable for the routine determination of ginsenosides in P. ginseng roots and extracts. The validation of the method was comprehensive for efficiency and recovery optimization of the P. ginseng roots extraction, specificity by liquid chromatography/mass spectrometry, linearity, stability, reproducibility, repeatability, intermediate precision, and robustness.
ginsenosides, ginseng, LC, ELSD
NCBI PubMed ID: 10995108Inasmuch as the oxidation of low-density lipoprotein (Ox-LDL) may play a key role in the initiation and progression of atherosclerosis, it has become increasingly important to identify potential antioxidants. Panax quinquefolium saponins (PQS) are extracted from the stems and leaves of the North American form of ginseng,Panax quinquefolium. Our previous studies have indicated that PQS (0.25-1 mg/ml) can protect against oxidation of LDLin vitro. The purpose of the current work was to investigate the potential interaction of lower concentrations of PQS (1-100 μg/ml) with vitamin C on the reduction of LDL oxidation. LDL was isolated from the plasma of healthy human donors by sequential ultracentrifugation. Native LDL (0.05 or 0.2 mg/ml) was incubated with PQS and/or vitamin C for 30 min at 20°C. Oxidative modification was initiated with 2 μM or 5 μM CuSO4 at 37°C for 0-24 h. Pretreatment with PQS (100 μg/ml) reduced alterations in phospholipids, lipid peroxide levels and relative electrophoretic mobility of Ox-LDL. The presence of vitamin C (1-10 μM) significantly enhanced the protective effects of PQS. Pretreatment with PQS (1-100 μg/ml) resulted in concentration-dependent inhibition of LDL oxidation and prolongation of lag time as determined from measurements of conjugated lipid hydroperoxide content in Ox-LDL samples. Interestingly, the inhibitory actions of lower amounts of PQS (1 and 10 μg/ml) on the formation of conjugated dienes were significantly increased when vitamin C (0.1 or 1 μM) was present. In conclusion, our results suggest that PQS not only have direct antioxidant property but at low concentrations, their actions can be enhanced by vitamin C.
Antioxidant, Panax quinquefolium saponins, vitamin C, LDL oxidation
NCBI PubMed ID: 10718627Triterpenoid and steroidal glycosides, referred to collectively as saponins, are bioactive compounds present naturally in many plants. They have considerable potential as pharmaceutical and/or nutraceutical agents in natural or synthetic form. Saponins, from a variety of sources, have been shown to have hypocholesterolemic, anticoagulant, anticarcinogenic, hepatoprotective, hypoglycemic, immunomodulatory, neuroprotective, anti-inflammatory and anti-oxidant activity. This paper reviews saponin research of the last decade, focussing on developments in understanding their mechanism of action and structure-activity relationships. Virtually all of this work has used animal and in vitro models. To date there are very few human data.
immunomodulation, hypoglycemic activity, antiinflammatory activity, anti-oxidant activity, Hepatoprotection, steroidal glycosides, saponins, neuroprotection, triterpenoid glycosides, hypocholesterolemic activity, anti-coagulation, anticarcinogen
NCBI PubMed ID: 11201296| New query | Export IDs | Home | Help |
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