51116-90-6

Upstream product

• 6892-79-1 betulafolienetriol 
• 6892-79-1 (20S)-dammar-24-ene-3α,12β,20-triol 
• 873583-49-4 (5R,8R,9R,10R,12R,13R,14R,17S)-17-((S)-1-Hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,12-diol 
• 6892-79-1 protopanaxadiol 
• 873850-45-4 3-β-hydroxy-12-β-O-trimethylacetyl-20(S)-protopanaxadiol 
• 6892-79-1 Betulafolienetriol 

Downstream Products

• 6892-79-1 protopanaxadiol 
• 67400-17-3 ginsenoside Rh₂ 
• 14197-60-5 ginsenoside Rg₃ 
• 67400-17-3 Ginsenoside R_h2 
• 62025-49-4 ginsenoside F₂ 

Relevant academic research and scientific papers

Synthesis of 3α,20S-Dihydroxydammar-24-en-12-One β-D-Glucopyranosides

3α,20S-Dihydroxydammar-24-en-12-one 3-, 20-, and 3,20-di-O-β-D-glucopyranosides, close structural analogs of chikusetsusaponin-LT8 glycoside from Panax japonicus, were synthesized for the first time. Condensation of 3,20S-dihydroxydammar-24-en-12-one (1) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (6) in the presence of Ag2O gave a mixture of the three acetylated 3-, 20-, and 3,20-di-O-β-Dglucopyranosides 7–9 with 7 dominating (34.6%). Glycosylation of 3α-acetoxy-20S-hydroxydammar-24-en-12-one by glycosyl donor 6 led to regio- and stereoselective formation of acetylated 20-O-β-Dglucopyranoside 10 (48.6%). Subsequent removal of the protecting groups by sodium methoxide gave the corresponding free 3-, 20-, and 3,20-di-O-β-D-glucopyranosides 11–13.

GLYCOSYLATION OF TRITERPENOIDS OF THE DAMMARANE SERIES. IV. β-D-GLUCOPYRANOSIDES OF BETULAFOLIENETRIOL AND ITS DERIVATIVES

The glycosylation of betulafolienetriol (dammar-24-ene-3α,12β,20(S)-triol) under the conditions of the Koenigs-Knorr, the Heflerich, and the orthoester methods has been studied.It has been shown that the condensation of β-folienetriol and its 3-epimer with α-acetobromoglucose in the presence of silver oxide leads to a mixture of the corresponding 3-, 12-, and 20-mono- and 3,12- and 3,20-di-O-β-pD-glucopyranosides.It has been established that the glycosylation of dammar-24-ene-3α,12β,20(S)-triol under Heflerich's conditions and those of the orthoester method is accompanied by a side rea ction of dehydration in the side chain and leads to 20-dehydroxy derivatives.The structures of all the newly obtained compounds have been established on the basis of the results of IR and of 1H and 13C NMR spectroscopy.

Synthesis and biological evaluation of Ginsenoside Compound K analogues as a novel class of anti-asthmatic agents

Ginsenoside Compound K (CK) showed potent activity against IgE for the treatment of asthma. A series of CK analogues were then synthesized by straightforward procedures. The in vivo anti-IgE activity evaluations using the OVA-induced asthmatic mouse model revealed preliminary SARs of the CK analogues, which showed that the sugar type, modifications on A-ring and the C20 side chain of CK all affected much on the activities. Primary SARs optimization led to the discovery of compounds T1, T2, T3, T8 and T12, which displayed superior or comparable anti-asthmatic effects (IgE value = 1237.11 ± 106.28, 975.82 ± 160.32, 1136.96 ± 121.85, 1191.08 ± 107.59 and 1258.27 ± 148.70 ng/mL, respectively) in comparison with CK (1501.85 ± 184.66 ng/mL). These potent compounds could serve as leads for further development.

Panaxadiol glycoside derivative, a preparation method and applications thereof

The invention discloses a panaxadiol glycoside derivative, a preparation method and applications thereof. According to the present invention, the results of in vitro and animal model experiments showthat the compound has strong anti-inflammatory effects, such that the compound can used for preparing anti-inflammatory drugs, especially drugs for treatment of asthma and COPD; and in the experiments, the compound has obvious effects on asthma and COPD, the high-dose group has the treatment effects superior to dexamethasone and budesonide, and detection results of blood routine examination and blood glucose are not significantly affected at the dose of far more than the effective treatment dose, such that the compound has high application prospects in anti-inflammatory drugs, especially drugsfor treatment of asthma and COPD.

Ginsenoside derivative for treating dermatitis

The invention discloses a panaxadiol saponins derivative and a preparation method and application thereof. The compound embodies a very high anti-inflammatory effect in vitro and in animal model experiments, thus can be used for preparing anti-inflammatory drugs, and especially can be used for treating dermatitis. In the experiments, the compound has the obvious effect on dermatitis, has no significant impact on blood routine and blood glucose with the dose far beyond the effective treating dose, and has very high application prospects in the fields of the anti-inflammatory drugs, especially dermatitis treatment.

Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-DI-O-β-D- glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicus

A method for preparative production of 3β,20S-dihydroxydammar-24-en- 12-one 3,20-di-O-β-D-glucopyranoside (1), a glycoside from Panax japonicus, chikusetsusaponin-LT8 was developed. Chemical transformation of betulafolientriol, a component of Betula leaves extract, produced the 12-keto-20S-protopanaxadiol (3β,20S-dihydroxydammar-24-en-12-one) (2), exhaustive glycosylation of which by 2,3,4,6-tetra-O-acetyl-α-D- glucopyranosylbromide (3) under Koenigs - Knorr reaction conditions with subsequent removal of protecting groups formed 3β,20S-dihydroxydammar-24- en-12-one3,20-di-Q-β-D-glucopyranoside (1). The principal glycosylation product was 3β,20S-dihydroxydammar-24-en-12-one 3-O-β-D- glucopyranoside if equimolar amounts of (2) and (3) were used. 2006 Springer Science+Business Media, Inc.

Synthesis of 20S-protopanaxadiol 20-O-β-D-glucopyranoside, a metabolite of Panax ginseng glycosides, and compounds related to it

A preparative semi-synthetic method was developed to prepare 20S-protopanaxadiol 20-O-β-Dglucopyranoside (1), a metabolite of Panax ginseng glycosides. The 20-O-?-D-glucopyranosides of 20S-hydroxydammar-24- en-3,12-dione, 3β,20S-dihydroxydammar-24-en-12-one, and 3β,12α, 20S-trihydroxydammar-24-ene were synthesized for the first time.

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.

Synthesis of ginsenoside Rg3, a minor constituent of Ginseng radix.

Glycosylation of 12beta-acetoxy-dammar-24-en-3beta,20(S)-diol (4), with hepta-O-acetyl-alpha-sophorosyl bromide (5) under catalysis by Ag2CO3 or Ag2O afforded a chromatographically unseparated mixture of the alpha- and beta-linked octaacetates 6 and 7 in an approximately 2.5:1 ratio. After deprotection and chromatographic purification, the free alpha- (8) and beta-glycosides (9) were obtained. Sophoroside 9 was identical in all respects with ginsenoside Rg3, the minor component of Ginseng Radix rubra. All compounds were fully characterized by 1H and 13C NMR spectroscopy.

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.