73584-64-2

Upstream product

• 67-56-1 methanol 
• 1721-58-0 methyl 3-oxooleanolate 
• 508-02-1 Oleanolic acid 
• 17990-42-0 Oleanonsaeure 
• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 77-78-1 dimethyl sulfate 
• 95851-48-2 C₄₂H₆₈O₁₂ 
• 89837-91-2 C₄₈H₇₈O₁₃ 
• 101021-04-9 C₅₆H₉₄O₁₆ 
• 90138-33-3 C₅₇H₉₄O₁₈ 
• 53840-61-2 dimethyl ester of oleanolic acid 3-O-(3'-O-α-L-rhamnopyranosyl)-β-D-glucuronopyranoside 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 25493-69-0 (4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate 

Relevant academic research and scientific papers

Pentacylic triterpenes from Lavandula coronopifolia: structure related inhibitory activity on α-glucosidase

Ten pentacyclic triterpenes (1-10) were isolated from Lavandula coronopifolia. We evaluated their α-glucosidase inhibitory activity, and found that the aglycones, 1, 2, 3, 4, 7 and 10 showed superior IC50 values to the positive control. In order to explain the structural requirements for α-glucosidase inhibitory activity, eleven derivatives were prepared, including one new compound, 2-formyl-(A)1–19α-hydroxy-1-norursane-2, 12-dien-28-oic acid 10c. The results demonstrated that a free hydroxyl at ring-A and a free carboxylic group at position 28 are key structural features for the α-glucosidase inhibitory activity, also that an ursane skeleton is optimum for the activity. Additionally, enzyme kinetic analysis of pomolic acid 2, the most potent compound, revealed that it inhibited α-glucosidase in a mixed-type manner. The molecular docking simulation validated this type of inhibition and highlighted the role of the C-3 hydroxyl and C-28 carboxylic groups in interaction with the enzyme in silico.

Type and position of linkage govern the cytotoxicity of oleanolic acid rhodamine B hybrids

Oleanolic acid/rhodamine B hybrids exhibit different cytotoxicity depending on the way these two structural elements are linked. While a hybrid holding a piperazinyl spacer at C-28 proved to be cytotoxic in the nano-molar concentration range, hybrids with a direct linkage of the Rho B residue to C-3 of the triterpenoid skeleton are cytotoxic only in the low micro-molar concentration range without any selectivity. This once again underlines the importance of selecting the right spacer and the most appropriate position on the skeleton of the triterpene to achieve the most cytotoxic hybrids possible.

Application of methylsulfonyl 12-ketone oleanolic acid methyl ester in preparation of medicine for resisting viral hepatitis B

The invention relates to application of methylsulfonyl 12-ketone oleanolic acid methyl ester in preparation of a medicine for resisting viral hepatitis B, and particularly provides application of 3 beta-methylsulfonyloxy-12-carbonyl oleanane-28-carboxylic acid methyl ester in preparation of a medicine for preventing and treating hepatitis B virus infection diseases. The compound has remarkable activity of inhibiting HBsAg and HBeAg secreted by HepG2.2.15 cells. On the eighth day, the intensity of the compound at a concentration of 100 micrograms/milliliter for inhibiting the HBeAg secretion ishigher than that of positive control drugs alpha-interferon and lamivudine. The HBsAg secretion inhibition strength of the compound is 69.9% at the concentration, and the inhibition rate on HBV-DNA replication is higher than 97%. The above results show that the methylsulfonyl 12-ketone oleanolic acid methyl ester can be expected to be used for preparing non-nucleoside drugs for treating hepatitisB virus infection diseases. Specifically, the compound has the application for preparing an HBV-DNA inhibitor, an HBsAg inhibitor and an HBeAg inhibitor; and the preparation method is simple in steps, low in cost, wide in raw material source and easy for industrial production.

Application of methyl isocycloenone oleanolate to preparation of medicine for preventing and treating viral hepatitis B

The invention relates to an application of methyl isocycloenone oleanolate to preparation of a medicine for preventing and treating viral hepatitis B, and particularly provides an application of 3 beta-hydroxyl-12-carbonyl oleanane-13 (18)-alkene-28-carboxylic acid methyl ester to preparation of a medicine for resisting hepatitis B virus infection diseases. A compound has remarkable effect of inhibiting the activity of HBsAg and HBeAg secreted by HepG2.2. 15 cells, the intensity of inhibiting HBsAg and HBeAg secretion at the concentration of 100 micrograms/milliliter on the eighth day exceedsthat of positive control medicines namely alpha-interferon and lamivudine, and the inhibition rate of the compound on HBV-DNA replication is higher than 97% under the concentration. The result shows that the methyl isocycloenone oleanolate can be expected to be used for preparing non-nucleoside medicines for treating hepatitis B virus infection diseases; and specifically, the compound has the functions of being used for preparing an HBV-DNA inhibitor, an HBsAg inhibitor and an HBeAg inhibitor, and the preparation method is simple in step, low in cost, wide in raw material source and easy for industrial production.

Medicinal application of 12-ketone methyl oleanolate in preparation of anti-viral hepatitis B medicine

The invention relates to medicinal application of 12-ketone methyl oleanolate in preparation of anti-viral hepatitis B medicines and particularly provides application of 3beta-hydroxyl-12-carbonyl oleanolate-28-methyl carboxylate in preparation of medicines for preventing and treating hepatitis B viral infectious diseases. The compound has remarkable activity of inhibiting HBsAg and HBeAg secreted from HepG2.2.15 cells, the strength of the compound on inhibiting secretion of HBsAg and HBeAg are respectively 89.1 percent and 95.1 percent under the concentration of 100mg/ml on the 8th day, replication of the compound on HBV-DNA can show the inhibition rate of 92.6 percent under the concentration of 100mg/ml, which is higher than that of positive medicines alpha-interferon. Thus, the 12-ketone methyl oleanolate is expected to be applied to preparation of non-nucleoside drugs for treating hepatitis B viral infectious diseases, especially applied to preparation of HBV-DNA inhibitors, HBsAginhibitors and HBeAg inhibitors. The preparation method has simple steps and low cost, is wide in raw material sources and is easy for industrial production.

Preparation of dienyl mesyloxy oleanane alcohol and medical application of dienyl mesyloxy oleanane alcohol in resisting hepatitis B

The invention relates to preparation of dienyl mesyloxy oleanane alcohol and a medical application of the dienyl mesyloxy oleanane alcohol in resisting hepatitis B. Particularly, the invention provides an application of 3[beta]-mesyloxy oleanane 11,13(18)-dien-28-ol in preparation of a medicine for preventing and treating hepatitis B virus infected diseases. The intensity of the compound for inhibiting the secretion of HBsAg and HBeAg under the concentration of 100 micrograms/milliliter exceeds that of positive drugs alpha-interferon and lamivudine; and when the test concentration is only 1/50(2.0 micrograms/milliliter) of the highest test concentration of the lamivudine, the inhibitory activity of the compound on HBV-DNA replication is as high as 44.1%. It is showed that the dienyl mesyloxy oleanane alcohol can be expected to be used for preparing non-nucleoside medicines for treating the hepatitis B virus infected diseases; specifically, the compound has an application for preparingan HBV-DNA inhibitor, an HBsAg inhibitor and an HBeAg inhibitor; and the preparation method is simple in steps, low in cost, wide in raw material source and easy for industrial production.

Nematicidal activity of oleanolic acid derivatives on Meloidogyne incognita

In this study, oleanolic acid and its derivatives were studied for their invivo nematicidal activity against root-knot nematode (RKN) Meloidogyne incognita. A series of C-28-oleanolates including five new (5, 7–10) and seven known (1–4, 6, 11, 12) compounds were synthesised and their nematicidal activity was determined and compared with the standard nematicide furadan for the first time. The structures of the compounds were elucidated through 1H NMR, 13C NMR and EIMS. Compounds 4, 5, 7, 8 and 10 showed ～ 90percent inhibition of RKN at 0.125percent concentration after 72 h showing their potential use in nematicidal control.

Total syntheses of (+)-arisugacins F, G

(+)-Arisugacin F and G are synthesized from commercially available oleanolic acid in 9 and 10 steps, respectively. This strategy features a AgOTf/Pd(PPh3)4-mediated cis/trans olefin isomerization and a highly convergent formal oxa-[3 + 3] cycloaddition between key α, β-unsaturated aldehyde and pyrone, which lays the foundation for efficient and concise synthesis of other natural products with similar terpenoid scaffolds.

The Novel Synthetic Triterpene Methyl 3β-O-[4-(2-Aminoethylamino)-4-oxo-butyryl]olean-12-ene-28-oate Inhibits Breast Tumor Cell Growth in Vitro and in Vivo

Oleanolic and ursolic acids were used as lead compounds to synthesize a series of pentacyclic triterpenoid derivatives bearing ethylenediamine, butanediamine, or hexanediamine groups at the C-3 position. The potential antiproliferative activity of these compounds was examined in A549 (human non-small cell lung cancer cells), MCF-7 (human breast cancer cells), and HeLa (human cervical carcinoma cells) cells. Methyl 3β-O-[4-(2-aminoethylamino)-4-oxo-butyryl]olean-12-ene-28-oate (DABO-Me) was identified as a promising antiproliferative agent in vitro and in vivo. DABO-Me strongly suppressed the proliferation of A549, MCF-7, and HeLa cells (IC50=4–7μM). In MCF-7 cells, DABO-Me upregulated the pro-apoptotic protein Bax, downregulated the anti-apoptotic protein Bcl-2, promoted the release of cytochrome c, and activated caspase-3/9. Transwell and flow cytometry assays showed that DABO-Me inhibited MCF-7 cell proliferation, migration, and invasion, and induced apoptosis and S phase arrest. In vitro and in vivo experiments indicated that DABO-Me inhibited MCF-7 cell proliferation and suppressed tumor growth. Taken together, these results indicate that DABO-Me could be developed as an effective antitumor drug.

Oleanolic acid oxime derivatives and their conjugates with aspirin modulate the NF-κB-mediated transcription in HepG2 hepatoma cells

The aim of this study was to evaluate the effect of new oleanolic acid oxime (OAO) derivatives and their conjugates with aspirin (ASP) on the expression and activation of NF-κB in human hepatoma HepG2 cells. OAO derivatives showed a stronger cytotoxic effect against HepG2 cells compared with their conjugates with aspirin. Moreover, conjugation of OAO with ASP led to enhanced downregulation of NF-κB expression and activation. Among the hybrids with ASP, compounds: 19, 3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid morpholide and 13, 3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid methyl ester, differing, respectively, in morpholide and methyl ester groups at the C-17 position of oleanolic acid (OA) molecule were the most efficient. COX-2 transcript and protein levels were also diminished after treatment with these compounds. The results of this study indicate that the new derivatives of OAO and particularly their conjugates with ASP, downregulate the expression of COX-2 in HepG2 cells by modulating the NF-κB signaling pathway and suggest their potential application in the prevention of liver inflammation and cancer.