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3-oxo-Olean-12-en-28-oic acid

CAS# 17990-42-0

3-oxo-Olean-12-en-28-oic acid

Catalog No. BCN3171----Order now to get a substantial discount!

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Chemical structure

3-oxo-Olean-12-en-28-oic acid

3D structure

Chemical Properties of 3-oxo-Olean-12-en-28-oic acid

Cas No. 17990-42-0 SDF Download SDF
PubChem ID 12313704 Appearance White powder
Formula C30H46O3 M.Wt 454.7
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms 3-Oxooleanolic acid
Solubility DMSO : 100 mg/mL (219.93 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name (4aS,6aR,6aS,6bR,8aR,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
SMILES CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(=O)C5(C)C)C)C)C2C1)C)C(=O)O)C
Standard InChIKey FMIMFCRXYXVFTA-FUAOEXFOSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of 3-oxo-Olean-12-en-28-oic acid

1 Lantana sp. 2 Pistacia sp. 3 Scrophularia sp. 4 Ziziphus sp.

Biological Activity of 3-oxo-Olean-12-en-28-oic acid

Description3-oxo-Olean-12-en-28-oic acid and kulinone have cytotoxic effects, with IC50 values of 5.6-21.2 μg/mL.
In vitro

Cytotoxic triterpenoids and steroids from the bark of Melia azedarach.[Pubmed: 21243584]

Planta Med., 2011, 77(9):922-8.

Two new triterpenoids (1, 2) and two new steroids (3, 4) along with twelve related known compounds (5-16) were isolated from the bark of Melia azedarach.
METHODS AND RESULTS:
The new structures were elucidated by means of spectroscopic methods and molecular modeling studies and found to be 21,24-cycloeupha-7-ene-3 β,16 β,21 α,25-tetrol (1), 3 β-acetoxy-12 β-hydroxy-eupha-7,24-dien-21,16 β-olide (2), 29-hydroperoxy-stigmasta-7,24(28) E-dien-3 β-ol (3), and 24 ξ-hydroperoxy-24-vinyl-lathosterol (4). All isolated compounds were tested for their cytotoxic activity against three human cancer cell lines (A549, H460, HGC27) using the CellTiter Glo™ luminescent cell viability assay.
CONCLUSIONS:
Among them, compounds 2- 4, 24 ξ-hydroperoxy-24-vinyl-cholesterol (6), kulinone (7), meliastatin 3 ( 8), 3-oxo-Olean-12-en-28-oic acid (10), and (22 E,24 S)-5 α,8 α-epidioxy-24-methyl-cholesta-6,22-dien-3 β-ol (12) were found to have cytotoxic effects, with IC₅₀ values of 5.6-21.2 μg/mL.

3-oxo-Olean-12-en-28-oic acid Dilution Calculator

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3-oxo-Olean-12-en-28-oic acid Molarity Calculator

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Preparing Stock Solutions of 3-oxo-Olean-12-en-28-oic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1993 mL 10.9963 mL 21.9925 mL 43.985 mL 54.9813 mL
5 mM 0.4399 mL 2.1993 mL 4.3985 mL 8.797 mL 10.9963 mL
10 mM 0.2199 mL 1.0996 mL 2.1993 mL 4.3985 mL 5.4981 mL
50 mM 0.044 mL 0.2199 mL 0.4399 mL 0.8797 mL 1.0996 mL
100 mM 0.022 mL 0.11 mL 0.2199 mL 0.4399 mL 0.5498 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on 3-oxo-Olean-12-en-28-oic acid

Oleanolic acid is a triterpenoid, inhibits infection by HIV-1 in in vitro infected PBMC, naturally infected PBMC and monocyte/macrophages with EC50 of 22.7 mM, 24.6 mM and 57.4 mM, respectively. Besides,it has IC50 of 17μM for the production of leukotriene B4 from rat peritoneal leukocytes. IC50:17μM(The production of leukotriene B4 from rat peritoneal leukocytes)[1] IC50:22.7 mM, 24.6 mM and 57.4 mM(in vitro infected PBMC, naturally infected PBMC and monocyte/macrophages by HIV-1, respectively.[2] In vitro: The highest of the four tested doses (100 μM), showed only a slight inhibition approximately, 30%. In contrast, the more powerful effect of oleanonic acid in this system, suggests that it acts through a mechanism related to the inhibition of 5-lipoxygenase, either directly or interfering with some of the mechanisms that participate in the complex activation of this enzyme. Oleanonic acid also acts by reducing prostaglandin synthesis.[1] Oleanolic acid inhibits the HIV-1 replication in all the cellular systems used (EC50 values: 22.7 microM, 24.6 microM and 57.4 microM for in vitro infected PBMC, naturally infected PBMC and M/M, respectively). As regards the mechanism of action, oleanolic acid inhibits in vitro the HIV-1 protease activity.[2] In vivo: Oleanonic acid exerted no activity on the oedema induced by application of ethyl phenylpropiolate after a pre-treatment of 16 h. In the TPA ear oedema test, it showed a non-significant 28% inhibition. However, when assayed on the ear oedema induced by DPP, oleanonic acid reduced the swelling by 40%, an effect similar to that of the standard carbamazepine. In the mouse model of delayed hypersensitivity induced by dinitrofluorobenzene, oleanonic acid was ineffective at both 24 and 96 h, while oleanolic acid reduced non-significantly the oedema at 96 h by 32%.In the TPA model of chronic inflammation induced by multiple applications, oleanonic acid showed a significant effect, with 45% inhibition. In contrast, oleanolic acid was inactive. Both inhibited the neutrophil infiltration measured as myeloperoxidase activity by 84% and 67%, respectively. The inhibition observed for dexamethasone on the swelling and myeloperoxidase activity was around 90%. The histological study of ears treated only with repeated doses of TPA showed an extensive diffusive inflammatory lesion with microabscesses affecting dermis and epidermis. The main infiltrating cells in the skin were neutrophils and epithelial thickness was 6.6±1.0 cells. In the tissues treated only with the solvent acetone, epithelial thickness was 2.1±0.5 and no signs of lesion or leukocyte infiltration were detectable. The multidose treatment with oleanonic acid reduced both the intensity and extension of the damage produced by TPA, as this was localized in the dermis, where the main infiltrating cells were lymphocytes, and where fibrosis was observed. In this case, epithelium thickness was 4.4±0.7 cells. The ears treated with dexamethasone showed minimal inflammatory lesions and sometimes none at all, and the epithelium thickness was 4.3±0.7 cells.The paw oedema induced by bradykinin was significantly reduced (61%) by oleanonic acid, whereas isoprenaline had a slightly lower effect (52%). Both oleanolic and oleanonic acid also reduced the paw oedema induced by phospholipase A2; the latter showing its strongest effect at 60 min, with an 84% inhibition, and maintaining activity at 90 min. Oleanolic acid also had its maximum effect at 60 min, vanishing at 90 min, while the activity of cyproheptadine was uniform along the experiment, ranging 80–90% inhibition .[1]

References:
[1]. Giner-Larza EM et al.Oleanonic acid, a 3-oxotriterpene from Pistacia, inhibits leukotriene synthesis and has anti-inflammatory activity.Eur J Pharmacol.Sep 28;428(1):137-43.doi:10.1016/S0014-2999(01)01290-0(2001) [2]. Fabio Mengoni.Anti-HIV Activity of Oleanolic Acid on Infected Human Mononuclear Cells.Planta Med 68(2): 111-114.DOI: 10.1055/s-2002-20256(2002)

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References on 3-oxo-Olean-12-en-28-oic acid

Cytotoxic triterpenoids and steroids from the bark of Melia azedarach.[Pubmed:21243584]

Planta Med. 2011 Jun;77(9):922-8.

Two new triterpenoids (1, 2) and two new steroids (3, 4) along with twelve related known compounds (5-16) were isolated from the bark of Melia azedarach. The new structures were elucidated by means of spectroscopic methods and molecular modeling studies and found to be 21,24-cycloeupha-7-ene-3 beta,16 beta,21 alpha,25-tetrol (1), 3 beta-acetoxy-12 beta-hydroxy-eupha-7,24-dien-21,16 beta-olide (2), 29-hydroperoxy-stigmasta-7,24(28) E-dien-3 beta-ol (3), and 24 xi-hydroperoxy-24-vinyl-lathosterol (4). All isolated compounds were tested for their cytotoxic activity against three human cancer cell lines (A549, H460, HGC27) using the CellTiter Glo luminescent cell viability assay. Among them, compounds 2- 4, 24 xi-hydroperoxy-24-vinyl-cholesterol (6), kulinone (7), meliastatin 3 ( 8), 3-oxo-Olean-12-en-28-oic acid (10), and (22 E,24 S)-5 alpha,8 alpha-epidioxy-24-methyl-cholesta-6,22-dien-3 beta-ol (12) were found to have cytotoxic effects, with IC(5)(0) values of 5.6-21.2 microg/mL.

Description

Oleanonic acid (3-Oxooleanolic acid) is a triterpenoid, inhibits infection by HIV-1 in in vitro infected PBMC, naturally infected PBMC and monocyte/macrophages with EC50 of 22.7 mM, 24.6 mM and 57.4 mM, respectively.

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