GrifolinCAS# 6903-07-7 |
Quality Control & MSDS
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| Cas No. | 6903-07-7 | SDF | Download SDF |
| PubChem ID | 5372312 | Appearance | Powder |
| Formula | C22H32O2 | M.Wt | 328.49 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 5-methyl-2-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene-1,3-diol | ||
| SMILES | CC1=CC(=C(C(=C1)O)CC=C(C)CCC=C(C)CCC=C(C)C)O | ||
| Standard InChIKey | PZHNKNRPGLTZPO-VZRGJMDUSA-N | ||
| Standard InChI | InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-21(23)14-19(5)15-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10+,18-12+ | ||
| 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. |
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| 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. |
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| 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. | ||
| Description | 1. Grifolin enhances the differentiation and proliferation of oligodendrocyte precursor cells (OPCs) in oxygen/glucose deprivation (OGD)-induced injury by altering the expressions of Id2 and Olig2. 2. Grifolin has anti-cancer effects, it induces apoptosis and promotes cell cycle arrest in the A2780 human ovarian cancer cell line via inactivation of the ERK1/2 and Akt pathways. 3. Grifolin inhibits tumor cells adhesion and migration via suppressing interplay between PGC1α and Fra-1 / LSF- MMP2 / CD44 axes. 4. Grifolin possesses antimicrobial activities against Bacillus cereus and Enterococcus faecalis. 5. Grifolin shows antifungal activity against plant pathogenic fungi (Erysiphe graminis). 6. Grifolin exhibits in vitro antileishmanial activity. 7. Grifolin shows hypocholesterolemic action on rats fed with a High-cholesterol diet. |
| Targets | Akt | ERK | Bcl-2/Bax | Caspase | PARP | ROS | MMP(e.g.TIMP) | Antifection |
Grifolin Dilution Calculator
Grifolin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.0442 mL | 15.2212 mL | 30.4423 mL | 60.8847 mL | 76.1058 mL |
| 5 mM | 0.6088 mL | 3.0442 mL | 6.0885 mL | 12.1769 mL | 15.2212 mL |
| 10 mM | 0.3044 mL | 1.5221 mL | 3.0442 mL | 6.0885 mL | 7.6106 mL |
| 50 mM | 0.0609 mL | 0.3044 mL | 0.6088 mL | 1.2177 mL | 1.5221 mL |
| 100 mM | 0.0304 mL | 0.1522 mL | 0.3044 mL | 0.6088 mL | 0.7611 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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Hypocholesterolemic Action of Dietary Grifolin on Rats Fed with a High-cholesterol Diet.[Pubmed:27315726]
Biosci Biotechnol Biochem. 1994 Jan;58(1):211-2.
The hypocholesterolemic action of Grifolin was investigated in terms of its structure-activity relationship with rats fed on a high-cholesterol diet. The results show that the structure of farnesylorcinol was required for the hypocholesterolemic action, and that the effect of Grifolin might be elicited, at least in part, through the augmented excretion of cholesterol into the feces.
Grifolin inhibits tumor cells adhesion and migration via suppressing interplay between PGC1alpha and Fra-1 / LSF- MMP2 / CD44 axes.[Pubmed:27626695]
Oncotarget. 2016 Oct 18;7(42):68708-68720.
Grifolin, a farnesyl phenolic compound isolated from the fresh fruiting bodies of the mushroom Albatrellus confluens, exhibits effective antitumor bioactivity in previous study of our group and other lab. In this study, we observed that Grifolin inhibited tumor cells adhesion and migration. Moreover, Grifolin reduced reactive oxygen species (ROS) production and caused cellular ATP depletion in high-metastatic tumor cells. PGC1alpha (Peroxisome proliferator-activated receptor gamma, coactivator 1alpha) encodes a transcriptional co-activator involved in mitochondrial biogenesis and respiration and play a critical role in the maintenance of energy homeostasis. Interestingly, Grifolin suppressed the mRNA as well as protein level of PGC1alpha. We further identified that MMP2 and CD44 expressions were PGC1alpha inducible. PGC1alpha can bind with metastatic-associated transcription factors: Fra-1 and LSF and the protein-protein interaction was attenuated by Grifolin treatment. Overall, these findings suggest that Grifolin decreased ROS generation and intracellular ATP to suppress tumor cell adhesion/migration via impeding the interplay between PGC1alpha and Fra-1 /LSF-MMP2/CD44 axes. Grifolin may develop as a promising lead compound for antitumor therapies by targeting energy metabolism regulator PGC1alpha signaling.
Antibacterial compounds from mushrooms I: a lanostane-type triterpene and prenylphenol derivatives from Jahnoporus hirtus and Albatrellus flettii and their activities against Bacillus cereus and Enterococcus faecalis.[Pubmed:19644795]
Planta Med. 2010 Feb;76(2):182-5.
Antibacterial bioassay-guided fractionation of two American mushroom species, Jahnoporus hirtus and Albatrellus flettii, led to the isolation and identification of their major antibacterial constituents: 3,11-dioxolanosta-8,24( Z)-diene-26-oic acid (1) from J. hirtus and confluentin (2), Grifolin (3), and neoGrifolin (4) from A. flettii. Compound 1 is a new lanostane-type triterpene. All purified compounds were evaluated for their ability to inhibit the growth of Bacillus cereus and Enterococcus faecalis using standard MIC assays. Compounds 1- 4 demonstrated MIC values of 40, 20, 10, and 20 microg/mL, respectively, against B. cereus and MIC values of 32, 1.0, 0.5, and 0.5 microg/mL, respectively, against E. faecalis. Thus, one novel compound and three others were shown to possess antimicrobial activities against these gram-positive bacteria employed as surrogates for more virulent and dangerous pathogens.
Grifolin induces apoptosis and promotes cell cycle arrest in the A2780 human ovarian cancer cell line via inactivation of the ERK1/2 and Akt pathways.[Pubmed:28588729]
Oncol Lett. 2017 Jun;13(6):4806-4812.
Grifolin, a secondary metabolic product isolated from the mushroom Albatrellus confluence, has been demonstrated to possess antitumor activities in a variety of malignant cells. However, the signaling pathways and the molecular mechanisms underlying the anticancer effects of the agent in human ovarian cancer remain to be elucidated. The aim of the present study was to examine the effect of Grifolin treatment on the human ovarian cancer cell line, A2780. MTT and flow cytometry analysis were used to analyze the viability of A2780 cells following treatment with Grifolin. Western blotting was used analyze the expression of apoptosis-associated and cell cycle arrest-associated proteins. The results of MTT assays and flow cytometry analysis revealed that Grifolin suppressed cell viability, induced apoptosis and triggered cell cycle arrest. Western blotting revealed that Grifolin treatment resulted in inactivation of protein kinase B (Akt) and extracellular signal-related kinase 1/2 (ERK1/2), accompanied by upregulation of Bcl-2 associated X, apoptosis regulator, cleaved-caspase-3 and cleaved-poly (ADP-ribose) polymerase, and downregulation of B cell lymphoma-2, cyclin dependent kinase 4 and cyclinD1. The results of the present study indicated that Grifolin had significant anti-cancer effects on the human ovarian cancer A2780 cells, which occurred via the Akt and ERK1/2 signaling pathways to at least a certain extent. These results demonstrate the therapeutic potential of Grifolin as a treatment for ovarian cancer.
Activity in vitro and in vivo against plant pathogenic fungi of grifolin isolated from the basidiomycete Albatrellus dispansus.[Pubmed:15787244]
Z Naturforsch C. 2005 Jan-Feb;60(1-2):50-6.
In the course of screening for novel naturally occurring fungicides from mushrooms in Yunnan province, China, the ethanol extract of the fruiting bodies of Albatrellus dispansus was found to show antifungal activity against plant pathogenic fungi. The active compound was isolated from the fruiting bodies of A. dispansus by bioassay-guided fractionation of the extract and identified as Grifolin by IR, 1H and 13C NMR and mass spectral analysis. Its antifungal activities were evaluated in vitro against 9 plant pathogenic fungi and in vivo against the plant disease of Erysiphe graminis. In vitro, Sclerotinina sclerotiorum and Fusarium graminearum were the most sensitive fungi to Grifolin, and their mycelial growth inhibition were 86.4 and 80.9% at 304.9 microM, respectively. Spore germination of F. graminearum, Gloeosporium fructigenum and Pyricularia oryzae was almost completely inhibited by 38.1microM Grifolin. In vivo, the curative effect of Grifolin against E. graminis was 65.5% at 304.9 microM after 8 days.
Grifolin Attenuates White Matter Lesion in Oxygen/Glucose Deprivation.[Pubmed:29071135]
Transl Neurosci. 2017 Oct 15;8:102-110.
The present study evaluates the effect of Grifolin (GFL) in oxygen/glucose deprivation (OGD) induced white matter lesion. Injury induced with OGD was found to be significant at the 9th h of OGD induction and the effect of GFL on the proliferation of oligodendrocyte precursor cells (OPCs) was assessed by CCK-8 and Hoechst 33258 assay at GFL 1, 5, 25, 50 and 100 mum concentrations. Whereas immunocytochemistry was performed for the assessment of survival and apoptosis of OPCs, western blot assay and RT-PCR were performed after 8th day of OGD injury for the estimation of expressions of myelin basic protein (MBP) and inhibitor of DNA binding 2 (Id2) in OPCs respectively. Results of the study suggests that treatment with GFL significantly enhances the survival rate and decreases the apoptosis of OPCs in OGD induced injury model. Immunocytochemical staining of Oligodendrocyte transcription factor (Olig2) and Bromodeoxyuridine (Brdu) shows that GFL treatment improves the proliferation of OPCs than OGD group. Moreover data of western blot assay suggested that treatment with GFL significantly enhances the expressions of MBP and Olig2 than OGD. It was observed that expressions of Id2 decreases and Olig2 enhances in GFL treated group than OGD group. Data of our study concludes that GFL enhances the differentiation and proliferation of OPCs in OGD-induced injury by altering the expressions of Id2 and Olig2.
In vitro and in vivo leishmanicidal studies of Peperomia galioides (Piperaceae).[Pubmed:23195082]
Phytomedicine. 1996 Nov;3(3):271-5.
Petroleum ether and methylene chloride extracts of Peperomia galioides and three prenylated diphenols, grifolic acid, Grifolin and piperogalin exhibited in vitro antileishmanial activity. During the course of infection of BALB/c mice with Leishmania amazonensis, the treatments with each of these compounds did not influence the progression of the disease.
