Masticadienolic acid | CAS:472-30-0 | Manufacturer ChemFaces

Masticadienolic acid

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Description:

Masticadienolic acid is a specific competitive inhibitor of secreted phospholipase A2, it not only protects the active site histidine from alkylation but also inhibits the action of secreted from pancreas, synovial fluid, and bee venom. Masticadienolic acid has anti-inflammatory activity, it shows effectiveness on the mouse ear inflammation induced by repeated applications of 12-0-tetradecanoylphorbol 13-acetate and on the phospholipase A2-induced foot paw edema.

Targets:

In vitro:

J Pharm Pharmacol. 2005 Sep;57(9):1087-91.

Cytotoxic activity and effect on nitric oxide production of tirucallane-type triterpenes.[Pubmed: 16105229]

METHODS AND RESULTS:
Hexane extract from the bark of Amphipterygium adstringens, as well as its principal constituents, masticadienonic acid and 3alpha-hydroxyMasticadienolic acid, inhibited the growth of five human cancer cell lines. Derivatives of, namely 24,25 S-dihydromasticadienonic acid and Masticadienolic acid, were also evaluated. The results showed that both and had greater activity than on colon cancer cell lines. The effects of on the production of nitric oxide (NO) from both resting and lipopolysaccharide-activated macrophages were determined.
CONCLUSIONS:
It was found that and caused an increase in NO release from resting macrophages; in lipopolysaccharide-activated macrophages, only and caused an increase in NO production.

In vivo:

Planta Med. 2002 Apr;68(4):311-5.

Anti-inflammatory triterpenes from Pistacia terebinthus galls.[Pubmed: 11988853]

From the galls of Pistacia terebinthus we obtained an extract that proved to be effective against chronic and acute inflammation.
METHODS AND RESULTS:
Now we report on the isolation and identification of three triterpenes: two tirucallane-type lanostanoids and one oleanane, which we have identified as masticadienonic acid (1), Masticadienolic acid (2), and morolic acid (3), respectively. All of them showed effectiveness on the mouse ear inflammation induced by repeated applications of 12-O-tetradecanoylphorbol 13-acetate and on the phospholipase A2-induced foot paw edema.
CONCLUSIONS:
The pharmacological activity of the compounds was ratified by a histological study of the ear samples. In addition, they inhibited leukotriene B4 production in rat polymorphonuclear leukocytes stimulated with calcium ionophore A 23187.

Masticadienolic acid Description

Source:	The herbs of Myrica nana.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Structure Identification:

Phytochemistry. 1995 Jun;39(3):537-47.

Specific competitive inhibitor of secreted phospholipase A2 from berries of Schinus terebinthifolius.[Pubmed: 7576451]

Two structurally related triterpenoids 1 and 2 from pink peppercorn (berries of Schinus terebinthifolius) are identified and characterized as active site-directed specific competitive inhibitors of the three classes of secreted 14 kDa phospholipase A2. The inhibitors not only protect the active site histidine from alkylation but also inhibit the action of secreted phospholipase A2 from pig pancreas, human synovial fluid, and bee venom. Detailed X-ray crystallographic results on the structures of the inhibitors are provided.
METHODS AND RESULTS:
By physical methods and X-ray crystallography the triterpenoids were identified as masticadienoic acid and Masticadienolic acid (schinol). Several other triterpenoids were ineffective as inhibitors of phospholipase A2; however certain ganoderic acid derivatives showed noticeable inhibition. Results show that the side chain of these acidic tetracyclic terpenoids can access the catalytic-site region of phospholipase A2, whereas the acyclic nucleus is at the interfacial recognition region. The selectivity of the assay protocol used here is demonstrated by the fact that the original screen of ethyl acetate extracts of 60 commercially available spices and herbs was carried out with phospholipase A2 from pig pancreas, and only one extract showed inhibitory action on the hydrolytic activity in the scooting mode. Under such assay conditions the enzyme remains tightly bound to the surface of the substrate vesicles. In this way, nonspecific effects of additives that promote desorption of the enzyme from the substrate vesicle surface, under conditions in which the binding of the enzyme to the vesicle is weak, are avoided.
CONCLUSIONS:
The assay protocol is useful for the kinetic characterization of the inhibitors of phospholipase A2, and it does not give false positive results with amphiphilic and hydrophobic compounds, as is the case with virtually all assay systems in use.

Product Name	Masticadienolic acid
Price:
CAS No.:	472-30-0
Catalog No.:	CFN98707
Molecular Formula:	C₃₀H₄₈O₃
Molecular Weight:	456.7 g/mol
Purity:	>=98%
Type of Compound:	Triterpenoids
Physical Desc.:	Cryst.
Source:	The herbs of Myrica nana.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Anti-inflammatory Compound Library Inhibitors Compound Library Triterpenoids Compound Library NO Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.1896 mL	10.9481 mL	21.8962 mL	43.7924 mL	54.7405 mL
5 mM	0.4379 mL	2.1896 mL	4.3792 mL	8.7585 mL	10.9481 mL
10 mM	0.219 mL	1.0948 mL	2.1896 mL	4.3792 mL	5.4741 mL
50 mM	0.0438 mL	0.219 mL	0.4379 mL	0.8758 mL	1.0948 mL
100 mM	0.0219 mL	0.1095 mL	0.219 mL	0.4379 mL	0.5474 mL

CFN90369	3Beta-acetoxy-eupha-7,25-dien-24(R)-ol	1352001-09-2	484.75	C₃₂H₅₂O₃
CFN99253	Dihydroniloticin	115334-05-9	458.7	C₃₀H₅₀O₃
CFN99254	Niloticin	115404-57-4	456.7	C₃₀H₄₈O₃
CFN97458	24,25-Epoxytirucall-7-en-3,23-dione	890928-81-1	454.7	C₃₀H₄₆O₃
CFN99017	Piscidinol A	100198-09-2	474.7	C₃₀H₅₀O₄
CFN99252	Phellochin	115334-04-8	488.8	C₃₁H₅₂O₄
CFN98707	Masticadienolic acid	472-30-0	456.7	C₃₀H₄₈O₃
CFN99671	3,4-Secotirucalla-4(28,7,24-triene-3),26-dioic acid	159623-48-0	470.7	C₃₀H₄₆O₄