112246-15-8

Usage

Uses

1. Used in Pharmaceutical Applications:
(2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6-methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol is used as a potential therapeutic agent for various diseases due to its unique molecular structure and multiple hydroxyl groups, which may allow for interactions with biological targets.
2. Used in Drug Delivery Systems:
In the pharmaceutical industry, (2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6-methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol can be used as a component in drug delivery systems, potentially enhancing the solubility, stability, and bioavailability of other therapeutic agents.
3. Used in Chemical Research:
(2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6-methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol may also be utilized in chemical research for the synthesis of novel compounds or as a starting material for the development of new drugs with potential therapeutic applications.

Physical form

Solid

Biochem/physiol Actions

20(R)-Ginsenoside Rh2, a matrix metalloproteinase (MMP) inhibitor, acts as a cell antiproliferator. It has anticancer effects via blocking cell proliferation and causing G1 phase arrest. 20(R)-Ginsenoside Rh2 induces apoptosis, and has anti-inflammatory and antioxidative activity. 20(R)-Ginsenoside Rh2 inhibits the replication and proliferation of mouse and human gammaherpesvirus 68 (MHV-68) with an IC50 of 2.77 μM for murine MHV-68. Ginsenoside Rh2 is a triterpene saponin found in Panax (ginseng) that exhibits immunomodulatory, neuroprotective, cognition enhancing, anti-inflammatory, antioxidative, and anticancer activities. In CD8+ T cells, ginsenoside Rh2 increases production of IFN-γ and activation of p38 MAPK and ERK, resulting in an increase in cell proliferation. In animals undergoing the Morris water maze test, ginsenoside Rh2 improves spatial learning and memory. (2R,3R,4S,5R,6R)-2-[[(10S,12S,14R,17S)-12-hydroxy-17-[(2R)-2-hydroxy-6 -methyl-hept-5-en-2-yl]-4,4,10,14,17-pentamethyl-2,3,5,6,7,8,9,11,12,1 3,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxyme thyl)oxane-3,4,5-triol also modulates expression of inflammatory markers, decreasing expression of toll-like receptor 4 (TLR4), CD14, TNF-α, IL-1α and HIF-1α, and inhibiting degradation of IκB kinase and translocation of NF-κB across various cellular models.

InChI:InChI=1/C36H62O8/c1-20(2)10-9-14-36(8,42)35(7)17-16-34(6)21-11-12-25-32(3,4)26(13-15-33(25,5)22(21)18-23(38)30(34)35)44-31-29(41)28(40)27(39)24(19-37)43-31/h10,21-31,37-42H,9,11-19H2,1-8H3/t21?,22?,23-,24+,25?,26?,27+,28-,29+,30?,31-,33+,34+,35-,36+/m0/s1

Upstream product

• 6892-79-1 (20S)-dammar-24-ene-3α,12β,20-triol 
• 6892-79-1 protopanaxadiol 
• 14197-60-5 ginsenoside Rg₃ 
• 133-89-1 UDP-glucose 
• 57-50-1 Sucrose 
• 873850-51-2 C₆₉H₈₆O₁₃ 
• 127750-92-9 12β-acethoxy-3β,20S-dihydroxydammar-24-ene 
• 127750-93-0 12-O-acetyl-dammar-24-ene-12β,20(S)-diol-3-one 
• 51116-90-6 12-β-O-hydroxy-20(S)-hydroxydammarane-24-ene-3-one 
• 127761-61-9 (3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate 
• 108212-06-2 3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)dammar-24-ene-3β,12β,20(S)-triol 
• 97869-56-2 12β-Acetoxydammar-24-en-3β,20(S)-diol 
• 127750-93-0 12β-Acetoxy-20(S)-hydroxydammar-24-en-3-one 
• 51116-90-6 12β,20(S)-Dammar-24-en-3-one 

Downstream Products

• 117666-46-3 3,12-di-O-β-D-glucopyranosyl-dammar-24-ene-3β,12β,20(S)-triol 
• 1357259-75-6 12,6'-dioctanoyl ginsenoside Rh₂ 
• 127761-61-9 (3β,12β,20S)-12-(acetyloxy)-20-hydroxydammar-24(25)-en-3-yl β-D-glucopyranoside-2,3,4,6-tetraacetate 

Relevant academic research and scientific papers

Hydrolysis of the outer β-(1,2)-d-glucose linkage at the C-3 position of ginsenosides by a commercial β-galactosidase and its use in the production of minor ginsenosides

Commercial β-galactosidase from Aspergillus oryzae (SUMILACT LTM) was used for the bioconversion of the ginsenosides Rb1, Rb2, Rc, Rd, and Rg3 to gypenoside-XVII, compound-O, compound-MC1, F2, and Rh2, respectively. The optimal conditions were

Simplified preparation of the ginsenoside-Rh2 minor saponin from ginseng

Condensation of the 12-O-acetylderivative of 20(S)-protopanaxadiol [dammar-24-ene-3β,12β,20(S)-triol] with tetra-O-acetyl-α-D-glucopyranosyl bromide in the presence of silver oxide in dichloroethane, followed by deprotection with sodium methoxide in methanol, results in formation of the 3-O-β-D-glucopyranosyldammar-24-ene-3β,12β,20(S)-triol identical with natural ginsenoside-Rh2. The 12-O-acetyl-20(S)-protopanaxadiol is easily prepared from betulafolienetriol via the 3-keto-12-O-acetylderivative followed by NaBH4 reduction. This comparatively simple five-step synthesis makes this hitherto rare ginsenoside relatively accessible.

GLYCOSYLATION OF TRITERPENOIDS OF THE DAMMARANE SERIES. X. REGIO- AND STEREOSELECTIVE SYNTHESIS OF 20(S)-PROTOPANAXADIOL 3-O-β-D-GLUCOPYRANOSIDE (GINSENOSIDE Rh2)

The regio- and stereoselective synthesis of ginsenoside Rh2, which possesses anti-tumoral activity, has been effected by the glycosylation of 12β-acetoxydammar-24-ene-3β,20(S)-diol.Condensation with α-acetobromoglucose was carried out in the presence of silver oxide in dichloroethane at room temperature, and the yield of the desired glycoside amounted to 50percent.A method for the selective protection of the C-12-OH group of dammar-24-ene-3β,12β,20(S)-triol has been proposed.

One-Pot Synthesis of Ginsenoside Rh2 and Bioactive Unnatural Ginsenoside by Coupling Promiscuous Glycosyltransferase from Bacillus subtilis 168 to Sucrose Synthase

Ginsenosides, the major effective ingredients of Panax ginseng, exhibit various biological properties. UDP-glycosyltransferase (UGT)-mediated glycosylation is the last biosynthetic step of ginsenosides and contributes to their immense structural and functional diversity. In this study, UGT Bs-YjiC from Bacillus subtilis 168 was demonstrated to transfer a glucosyl moiety to the free C3-OH and C12-OH of protopanaxadiol (PPD) and PPD-type ginsenosides to synthesize natural and unnatural ginsenosides. In vitro assays showed that unnatural ginsenoside F12 (3-O-β-d-glucopyranosyl-12-O-β-d-glucopyranosyl-20(S)-protopanaxadiol) exhibited remarkable activity against diverse human cancer cell lines. A one-pot reaction by coupling Bs-YjiC to sucrose synthase (SuSy) was performed to regenerate UDP-glucose from sucrose and UDP. With PPD as the aglycon, an unprecedented high yield of ginsenosides F12 (3.98 g L-1) and Rh2 (0.20 g L-1) was obtained by optimizing the conversion conditions. This study provides an efficient approach for the biosynthesis of ginsenosides using a UGT-SuSy cascade reaction.

Highly efficient biotransformation of ginsenoside Rb1 and Rg3 using β-galactosidase from Aspergillus sp.

A preliminary study on the enzymatic biotransformation of ginsenosides is evaluated. β-Galactosidase from Aspergillus sp. displayed β-glucosidase activity, which was responsible for its ability to transform major ginsenoside Rb1 to rare ginsenoside F2 via ginsenoside Rd. The Rb1 conversion, Rd and F2 yields reached 100%, 80.7% and 14.3% after 60 h at 60 °C, respectively. Ginsenoside Rg3 can be selectively hydrolyzed and only Rh2 was obtained with this β-galactosidase as well. Before hydrolysis, an Rg3 inclusion complex was prepared with hydroxypropyl-β-cyclodextrin (HP-β-CD) to improve the aqueous solubility. The solubility of Rg3 increased 74.6 fold, and the phase solubility curve displayed a typical AL-type, which indicates the formation of a 1 : 1 inclusion complex. Using an enzyme loading of 500 U g-1 Rg3, the highest Rg3 conversion of 90.6% and Rh2 yield of 88.5% were obtained after 24 h at 60 °C. These results indicate that β-galactosidase from Aspergillus sp. could be useful for the mass production of rare ginsenosides.

METHOD FOR PREPARING NOVEL PROCESSED GINSENG OR AN EXTRACT THEREOF, THE USUALLY MINUTE GINSENOSIDE CONTENT OF WHICH IS INCREASED

The present invention relates to a method for preparing a processed ginseng or processed ginseng extract. Specifically, the invention relates to a method for preparing a processed ginseng or processed ginseng extract having increased ginsenoside contents. More specifically, the invention relates to a method of preparing a novel processed ginseng or processed ginseng extract having increased ginsenoside contents by preparing saponinase, fermenting ginseng or red ginseng with the prepared saponinase and hydrolyzing the fermented ginseng or red ginseng with an organic acid and to an anticancer supplement composition or pharmaceutical composition comprising the processed ginseng or processed ginseng extract prepared thereby.

Synthesis of ginsenoside Rh2 and chikusetsusaponin-LT8 via gold(I)-catalyzed glycosylation with a glycosyl ortho-alkynylbenzoate as donor

Glycosylation of the acid labile protopanaxadiol derivatives was succeeded with a glycosyl ortho-hexynylbenzoate as donor under the catalysis of PPh 3AuNTf2, leading to the subsequent elaboration of ginsenoside Rh2 and chikusetsusaponin-LT8 in a concise manner.

Microwave degradation of floatation-enriched ginsenoside extract from Panax quinquefolium L. Leaf

Even though the degradation of ginsenosides has been thoroughly studied in animals and in vitro using acids, enzymes, and intestinal bacteria, a new degradation method is established for obtaining the ginsenosides Rg3, Rh2 and their

Metabolism of 20(S)- and 20(R)-ginsenoside Rg3 by human intestinal bacteria and its relation to in vitro biological activities.

When ginsenoside Rg3 was anaerobically incubated with human fecal microflora, all specimens metabolized ginsenoside Rg3 to ginsenoside Rh2 and protopanaxadiol. The main metabolite was ginsenoside Rh2. 20(S)-ginsenoside Rg3 was quickly transformed to 20(S)

SEMISYNTHETIC ANALOGUES OF GINSENOSIDES, GLYCOSIDES FROM GINSENG

Glycosylation of the dammar-24-ene-3,12β,20(S)-triols with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (A) in the presence of silver oxide in dichloromethane gives a mixture of the acetylated 3-, 12-, 20-, 3,12-di-, and 3,20-di-O-β-D-glucopyranosyl derivatives in a total yield of 83-84.5percent.Under similar conditions, the 3-O-acetyl derivatives of dammar-24-ene-3,12β,20(S)-triols give a mixture of 12- and 20-O-β-D-glucopyranosyl derivatives.Condensation of betulafolienetriol both with the glycosyl bromide A in the presence of mercuric cyanide in nitromethane and with 3,4,6,-tri-O-acetyl-β-D-glucopyranose 1,2-(tert-butyl ortoacetate) in the presence of 2,4,6-trimethyl-pyridinium perchlorate in chlorobenzene under azeotropic distillation results in dehydration and 20-dehydroxyglucosides are formed.