Grifolic acid

Selective partial FFA4 (GPR120) agonist CAS# 80557-12-6

Grifolic acid

Catalog No. BCN4344----Order now to get a substantial discount!

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Chemical structure

Grifolic acid

3D structure

Chemical Properties of Grifolic acid

Cas No. 80557-12-6 SDF Download SDF
PubChem ID 9976563 Appearance Powder
Formula C23H32O4 M.Wt 372.5
Type of Compound Phenols Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO
Chemical Name 2,4-dihydroxy-6-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzoic acid
SMILES CC1=CC(=C(C(=C1C(=O)O)O)CC=C(C)CCC=C(C)CCC=C(C)C)O
Standard InChIKey QPIZDZGIXDKCRC-JTCWOHKRSA-N
Standard InChI InChI=1S/C23H32O4/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-19-20(24)14-18(5)21(22(19)25)23(26)27/h8,10,12,14,24-25H,6-7,9,11,13H2,1-5H3,(H,26,27)/b16-10+,17-12+
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 Grifolic acid

The Cylindrocarpon ianthothele var. majus

Biological Activity of Grifolic acid

Description1. Grifolic acid has antibacterial activity, it can inhibit the growth of Staphylococcus aureus and Staphylococcus epidermidis. 2. Grifolic acid is a natural carbonic anhydrase Ⅱ inhibitor(CAⅡ), it shows in-hibitory activities against CAⅡ with IC50 of 6.37 umol/L.
TargetsAntifection

Grifolic acid Dilution Calculator

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Grifolic acid Molarity Calculator

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Preparing Stock Solutions of Grifolic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6846 mL 13.4228 mL 26.8456 mL 53.6913 mL 67.1141 mL
5 mM 0.5369 mL 2.6846 mL 5.3691 mL 10.7383 mL 13.4228 mL
10 mM 0.2685 mL 1.3423 mL 2.6846 mL 5.3691 mL 6.7114 mL
50 mM 0.0537 mL 0.2685 mL 0.5369 mL 1.0738 mL 1.3423 mL
100 mM 0.0268 mL 0.1342 mL 0.2685 mL 0.5369 mL 0.6711 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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References on Grifolic acid

Free fatty acid receptor GPR120 is highly expressed in enteroendocrine K cells of the upper small intestine and has a critical role in GIP secretion after fat ingestion.[Pubmed:25535828]

Endocrinology. 2015 Mar;156(3):837-46.

Gastric inhibitory polypeptide (GIP) is an incretin secreted from enteroendocrine K cells in response to meal ingestion. Recently free fatty acid receptor G protein-coupled receptor (GPR) 120 was identified as a lipid sensor involved in glucagon-like peptide-1 secretion. However, Gpr 120 gene expression and its role in K cells remain unclear, partly due to difficulties in separation of K cells from other intestinal epithelial cells. In this study, we purified K cells using GIP-green fluorescent protein (GFP) knock-in mice, in which K cells can be visualized by GFP fluorescence. GFP-positive cells (K cells) were observed in the small intestine but not in the stomach and colon. K cell number and GIP content in K cells were significantly higher in the upper small intestine than those in the lower small intestine. We also examined the expression levels of several free fatty acid receptors in K cells. Among free fatty acid receptors, GPR120 was highly expressed in the K cells of the upper small intestine compared with the lower small intestine. To clarify the role of GPR120 on K cells in vivo, we used GPR120-deficient mice (GPR120(-/-)). GPR120(-/-) exhibited significantly lower GIP secretion (75% reduction, P < .01) after lard oil ingestion compared with that in wild-type mice. Consistently, pharmacological inhibition of GPR120 with Grifolic acid methyl ether in wild-type mice significantly attenuated lard oil-induced GIP secretion. In conclusion, GPR120 is expressed abundantly in K cells of the upper small intestine and plays a critical role in lipid-induced GIP secretion.

Use of a modified microplate bioassay method to investigate antibacterial activity in the Peruvian medicinal plant Peperomia galioides.[Pubmed:15325731]

J Ethnopharmacol. 2004 Oct;94(2-3):279-81.

A versatile microplate bioassay for quick and sensitive determination of antibacterial activity was developed for use in screening medicinal plants and identification of their active principles. This assay can be used to determine minimum inhibitory concentrations for small quantities of organic or water-soluble plant extracts. Bioassay-guided fractionation of the stem and leaves of Peperomia galioides using this method found fractions containing grifolin and Grifolic acid, which inhibited growth of Staphylococcus aureus and Staphylococcus epidermidis.

Structure-activity relationships of GPR120 agonists based on a docking simulation.[Pubmed:20685848]

Mol Pharmacol. 2010 Nov;78(5):804-10.

GPR120 is a G protein-coupled receptor expressed preferentially in the intestinal tract and adipose tissue, that has been implicated in mediating free fatty acid-stimulated glucagon-like peptide-1 (GLP-1) secretion. To develop GPR120-specific agonists, a series of compounds (denoted as NCG compounds) derived from a peroxisome proliferator-activated receptor gamma agonist were synthesized, and their structure-activity relationships as GPR120 agonists were explored. To examine the agonistic activities of these newly synthesized NCG compounds, and of compounds already shown to have GPR120 agonistic activity (Grifolic acid and MEDICA16), we conducted docking simulation in a GPR120 homology model that was developed on the basis of a photoactivated model derived from the crystal structure of bovine rhodopsin. We calculated the hydrogen bonding energies between the compounds and the GPR120 model. These energies correlated well with the GPR120 agonistic activity of the compounds (R(2) = 0.73). NCG21, the NCG compound with the lowest calculated hydrogen bonding energy, showed the most potent extracellular signal-regulated kinase (ERK) activation in a cloned GPR120 system. Furthermore, NCG21 potently activated ERK, intracellular calcium responses and GLP-1 secretion in murine enteroendocrine STC-1 cells that express GPR120 endogenously. Moreover, administration of NCG21 into the mouse colon caused an increase in plasma GLP-1 levels. Taken together, our present study showed that a docking simulation using a GPR120 homology model might be useful to predict the agonistic activity of compounds.

Novel selective ligands for free fatty acid receptors GPR120 and GPR40.[Pubmed:19471906]

Naunyn Schmiedebergs Arch Pharmacol. 2009 Sep;380(3):247-55.

GPR120 and GPR40 are G-protein-coupled receptors whose endogenous ligands are medium- and long-chain free fatty acids, and they are thought to play an important physiological role in insulin release. Despite recent progress in understanding their roles, much still remains unclear about their pharmacology, and few specific ligands for GPR120 and GPR40 besides medium- to long-chain fatty acids have been reported so far. To identify new selective ligands for these receptors, more than 80 natural compounds were screened, together with a reference compound MEDICA16, which is known to activate GPR40, by monitoring the extracellular regulated kinase (ERK) and [Ca(2+)](i) responses in inducible and stable expression cell lines for GPR40 and GPR120, respectively. MEDICA16 selectively activated [Ca(2+)](i) response in GPR40-expressing cells but not in GPR120-expressing cells. Among the natural compounds tested, grifolin derivatives, Grifolic acid and Grifolic acid methyl ether, promoted ERK and [Ca(2+)](i) responses in GPR120-expressing cells, but not in GPR40-expressing cells, and inhibited the alpha-linolenic acid (LA)-induced ERK and [Ca(2+)](i) responses in GPR120-expressing cells. Interestingly, in accordance with the pharmacological profiles of these compounds, similar profiles of glucagon-like peptide-1 secretion were seen for mouse enteroendocrine cell line, STC-1 cells, which express GPR120 endogenously. Taken together, these studies identified a selective GPR40 agonist and several GPR120 partial agonists. These compounds would be useful probes to further investigate the physiological and pharmacological functions of GPR40 and GPR120.

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