Crategolic acid

Names

[ Name ]:
Crategolic acid

[Synonym ]:
Maslinic acid
Olean-12-en-28-oic acid, 2,3-dihydroxy-, (2α,3β)-
maslinicacid
(2α,3β)- 2,3-dihydroxy-Olean-12-en-28-oic acid
(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Hawthorn Leaf Extract
(2α,3β)-2,3-Dihydroxyolean-12-en-28-oic acid
Crataegolic acid
(2α,3β)-2,3-dihydroxy-Olean-12-en-28-oic acid
CRATEGOLIC ACID

Biological Activity

[Description]:

Maslinic acid can inhibit the DNA-binding activity of NF-κB p65 and abolish the phosphorylation of IκB-α, which is required for p65 activation

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Natural Products >> Terpenoids and Glycosides

[Target]

p65

[In Vitro]

Maslinic acid (MA) inhibits LPS-induced NF-κB translocation to nucleus and phosphorylation of IκB-α. Maslinic acid has also been reported to suppress NF-κB regulated osteoclastogenesis in bone marrow monocytes and inhibit TNF-α-induced NF-κB activity and its downstream genes’ expression in pancreatic cancer cells. To confirm if the anti-inflammatory effects of olive pomace extracts (OPEs) inRAW264.7 cells can be attributed to Maslinic acid, dose-dependence experiments determined the effective concentration of Maslinic acid to be 10-20 μM. 20 μM Maslinic acid significantly suppresses TNF-α production and inhibits IL-1, IL-6, and COX-2 mRNA expression in RAW 264.7 cell. Maslinic acid (at 10 and 20 μM) significantly suppresses the DNA-binding activity of NF-κB p65 in LPS-induced RAW 264.7 cells. Pretreatment with Maslinic acid significantly reduces the LPS-induced phosphorylation of IκB-α[1].

[In Vivo]

Paw swelling is alleviated when mice are administered with 200 mg/kg Maslinic acid (MA), significantly suppressing inflammation, compared to the carrageenan induced control group, 4 h after λ-carrageenan injection (0.91±0.51 mm and 1.79±0.4 mm, respectively)[1].

[Cell Assay]

RAW 264.7 cells are seeded in 96-well culture plates at a density of 1×105 cells/mL and after incubation for 24 h, are treated with OPE1 (300 μg/mL or 400 μg/mL), OPE2 (20 μg/mL or 40 μg/mL), or Maslinic acid (10 μM or 20 μM) , as well as with/without LPS at the same time. Cell viability i determined using the WST-1 reagent. Briefly, WST-1 reagent (10 μL) is added to each well and incubated for 1h in a humidified incubator. The absorbance of the samples measured at 450 nm (reference wavelength is 750 nm). Viability is expressed as a percentage of the absorbance measured in LPS-treated cells[1].

[Animal admin]

Mice[1] Five-week-old male Balb/c mice (19-21 g) are housed in a conventional condition and provided with the free access to standard rodent chow and water. Edema is induced by intraplantar injection of 100 μL 1% carrageenan into the hind left paw. Maslinic acid is tested initially at a dose of 200 mg/kg, orally administered 60 min before and after carrageenan injection. Paw thickness is measured using electronic digital calipers, 2, 3, and 4 h following carrageenan treatment. Mice are sacrificed by carbon dioxide inhalation 4 h after carrageenan injection[1].

[References]

[1]. Fukumitsu S, et al. Anti-inflammatory and anti-arthritic effects of pentacyclic triterpenoids maslinic acid through NF-κB inactivation. Mol Nutr Food Res. 2016 Feb;60(2):399-409.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
570.0±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₀H₄₈O₄

[ Molecular Weight ]:
472.700

[ Flash Point ]:
312.6±26.6 °C

[ Exact Mass ]:
472.355255

[ PSA ]:
77.76000

[ LogP ]:
7.87

[ Appearance of Characters ]:
white to off-white

[ Vapour Pressure ]:
0.0±3.6 mmHg at 25°C

[ Index of Refraction ]:
1.568

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
acetone: soluble1mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Safety Information

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2940000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2940000000

Articles

Pentacyclic triterpene in Olea europaea L: A simultaneous determination by high-performance liquid chromatography coupled to mass spectrometry.

J. Chromatogr. A. 1410 , 68-75, (2015)

Pentacyclic triterpenes are gaining interest due to their beneficial health effects, as anti-inflammatory, anti-diabetic and anti-tumoral, among others. In this study, an analytical LC-MS method was d...

Chemical constituents of Tilia taquetii leaves and their inhibition of MMP-1 expression and elastase activities.

Nat. Prod. Commun. 9(12) , 1683-5, (2014)

The ethanol extract of Tilia taquetii Schneider leaves was investigated for its anti-wrinkle properties and for the relevant chemical constituents. Phytochemical studies led to the identification of f...

Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells.

Cytokine 36(5-6) , 211-7, (2006)

Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption. Maslinic acid, oleanolic acid, erythrodiol, and uvaol are pentacycl...