Oleanonic acid
(Synonyms: 齐墩果酮酸,3-Oxooleanolic acid) 目录号 : GC36798
Oleanonic Acid (3-Ketooleanolic Acid, 3-Oxooleanolic acid), extracted from Pistacia terebinthus galls, is a cell cycle inhibitor and used as antitumor agents.
Cas No.:17990-42-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oleanonic Acid (3-Ketooleanolic Acid, 3-Oxooleanolic acid), extracted from Pistacia terebinthus galls, is a cell cycle inhibitor and used as antitumor agents.
| Cas No. | 17990-42-0 | SDF | |
| 别名 | 齐墩果酮酸,3-Oxooleanolic acid | ||
| Canonical SMILES | CC1(C)C(CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@](C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H])=O | ||
| 分子式 | C30H46O3 | 分子量 | 454.68 |
| 溶解度 | DMSO: 100 mg/mL (219.93 mM); Water: < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.1993 mL | 10.9967 mL | 21.9935 mL |
| 5 mM | 0.4399 mL | 2.1993 mL | 4.3987 mL |
| 10 mM | 0.2199 mL | 1.0997 mL | 2.1993 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Development of New Antimicrobial Oleanonic acid Polyamine Conjugates
Antibiotics (Basel) 2022 Jan 12;11(1):94.PMID:35052971DOI:10.3390/antibiotics11010094.
A series of oleanolic acid derivatives holding oxo- or 3-N-polyamino-3-deoxy-substituents at C3 as well as carboxamide function at C17 with different long chain polyamines have been synthesized and evaluated for antimicrobial activities. Almost all series presented good to moderate activity against Gram-positive S. aureus, S. faecalis and B. cereus bacteria with minimum inhibitory concentration (MIC) values from 3.125 to 200 µg/mL. Moreover, compounds possess important antimicrobial activities against Gram-negative E. coli, P. aeruginosa, S. enterica, and EA289 bacteria with MICs ranging from 6.25 to 200 µg/mL. The testing of ability to restore antibiotic activity of doxycycline and erythromycin at a 2 µg/mL concentration in a synergistic assay showed that Oleanonic acid conjugate with spermine spacered through propargylamide led to a moderate improvement in terms of antimicrobial activities of the different selected combinations against both P. aeruginosa and E. coli. The study of mechanism of action of the lead conjugate 2i presenting a N-methyl norspermidine moiety showed the effect of disruption of the outer bacterial membrane of P. aeruginosa PA01 cells. Computational ADMET profiling renders this compound as a suitable starting point for pharmacokinetic optimization. These results give confidence to the successful outcome of bioconjugation of polyamines and oleanane-type triterpenoids in the development of antimicrobial agents.
Hypoglycaemic activity of Oleanonic acid, a 3-oxotriterpenoid isolated from Aidia Genipiflora (DC.) Dandy, involves inhibition of carbohydrate metabolic enzymes and promotion of glucose uptake
Biomed Pharmacother 2022 May;149:112833.PMID:35316751DOI:10.1016/j.biopha.2022.112833.
The present study evaluated the antidiabetic activities of the 70% ethanol stem bark extract of Aidia genipiflora (AGB) and one of its constituents, Oleanonic acid in streptozotocin (40 mg/kg)-induced diabetic rats. In vitro assays of glucose uptake and inhibition of carbohydrate metabolizing enzymes were then used to investigate their mechanism(s) of hypoglycaemic action. In silico evaluation of the pharmacokinetic and toxicity properties of the compound was also carried out. Administration of AGB (100-400 mg/kg) and Oleanonic acid (15 - 60 mg/kg) resulted in significant reductions (p < 0.001) in the blood glucose and considerable decrease (p < 0.05) in the elevated lipid parameters of the diabetic animals. AGB activity at 200 and 400 mg/kg; and Oleanonic acid at 60 mg/kg were comparable to glibenclamide (5 mg/kg). The extract and its isolate strongly inhibited α-glucosidase and α-amylase activity with IC50 values of (10.48 ± 1.39 µg/mL and 14.51 ± 1.26 µg/mL) and (36.52 ± 1.95 µM and 105.84 ± 1.08 µM) respectively. The glucose uptake assays showed that AGB and Oleanonic acid exerted both insulin-dependent and independent promotional effect of glucose transport into the periphery by upregulating the expression of PI3K and PPARγ transcripts with a concomitant increase in GLUT-4 transcripts. Although Oleanonic acid was predicted to be teratogenic, it was found to be generally non-lethal with favourable pharmacokinetics properties making it suitable for further studies. The study has shown that the stem bark of A. genipiflora is a source of new hypoglycaemic agents and that Oleanonic acid possesses hypoglycaemic and anti-hyperlipidaemic activities.
Oleanonic acid ameliorates pressure overload-induced cardiac hypertrophy in rats: The role of PKCζ-NF-κB pathway
Mol Cell Endocrinol 2018 Jul 15;470:259-268.PMID:29138023DOI:10.1016/j.mce.2017.11.007.
It has been reported that inflammation is closely related with cardiac hypertrophy. Some inflammatory cytokines such as tumor necrosis factor-α, interleukin-1β, and interleukin-6 directly induce cardiac hypertrophy, which is associated with the activation of nuclear factorkappa B (NF-κB). Thus, NF-κB is an attractive target for cardiac hypertrophy. In the present study, Oleanonic acid inhibited the elevation of transcriptional activity of NF-κB and reduced the mRNA expressions of hypertrophic genes such as atrial natriuretic factor (ANF) and brain natriuretic peptide (BNP) in a concentration-dependent manner in phenylephrine (PE)-treated cardiomyocytes. Furthermore, we found that Oleanonic acid inhibited the phosphorylation of protein kinase C ζ (PKCζ) at Thr410 site and then reduced the activation of NF-κB using gain- and loss-of-function approaches in PE-treated cardiomyocytes. In vivo, similar results were observed in abdominal aortic constriction (AAC) rats that were intragastrically administered with Oleanonic acid, and the pathological changes accompanying cardiac hypertrophy were relieved. In conclusion, Oleanonic acid can effectively ameliorate cardiac hypertrophy by inhibiting PKCζ-NF-κB signaling pathway.
Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic acid Polyamine Derivatives
Molecules 2022 Dec 2;27(23):8499.PMID:36500593DOI:10.3390/molecules27238499.
A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) Oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of Oleanonic acid demonstrated high potency with selectivity index SI 27 (IC50 21 μM) and 42 (IC50 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC50's 67 and 107 μM) and -2 (IC50's 86 and 68 μM correspondingly) serotypes.
Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity
Eur J Pharmacol 2001 Sep 28;428(1):137-43.PMID:11779030DOI:10.1016/s0014-2999(01)01290-0.
One of the best known bioactive triterpenoids is oleanolic acid, a widespread 3-hydroxy-17-carboxy oleanane-type compound. In order to determine whether further oxidation of carbon 3 affects anti-inflammatory activity in mice, different tests were carried out on oleanolic acid and its 3-oxo-analogue Oleanonic acid, which was obtained from Pistacia terebinthus galls. The last one showed activity on the ear oedema induced by 12-deoxyphorbol-13-phenylacetate (DPP), the dermatitis induced by multiple applications of 12-O-tetradecanoyl-13-acetate (TPA) and the paw oedemas induced by bradykinin and phospholipase A2. The production of leukotriene B4 from rat peritoneal leukocytes was reduced by Oleanonic acid with an IC50 of 17 microM. Negligible differences were observed in the response of both triterpenes to DPP, bradykinin, and phospholipase A2, while Oleanonic acid was more active on the dermatitis by TPA and on the in vitro leukotriene formation. In conclusion, the presence of a ketone at C-3 implies an increase in the inhibitory effects on models related to 5-lipoxygenase activity and on associated in vivo inflammatory processes.