EpifriedelanolCAS# 16844-71-6 |
- Friedelanol
Catalog No.:BCN5620
CAS No.:5085-72-3
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 16844-71-6 | SDF | Download SDF |
| PubChem ID | 119242 | Appearance | Cryst. |
| Formula | C30H52O | M.Wt | 428.7 |
| Type of Compound | Triterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (3S,4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-1,2,3,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-hexadecahydropicen-3-ol | ||
| SMILES | CC1C(CCC2C1(CCC3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C)C)C)C)C)C)O | ||
| Standard InChIKey | XCDQFROEGGNAER-PFOIMGGJSA-N | ||
| Standard InChI | InChI=1S/C30H52O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20-24,31H,9-19H2,1-8H3/t20-,21-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1 | ||
| 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 | Epifriedelanol has antitumor activity, it can reduce cellular senescence in human primary cells and may be used to develop dietary supplements or cosmetics that modulate tissue aging or aging-associated diseases. Epifriedelanol exhibits significant inhibition of NF-kappa B, it may be used to treat asthma. |
| Targets | NF-kB |
| In vitro | Epifriedelanol from the root bark of Ulmus davidiana inhibits cellular senescence in human primary cells.[Pubmed: 21049397]Planta Med. 2011 Mar;77(5):441-9.Among twenty-two compounds isolated, Epifriedelanol (3), ssioriside (15), and catechin-7-O- β-D-glucopyranoside (22) had inhibitory effects on adriamycin-induced cellular senescence in HDFs. Friedelin (2), Epifriedelanol (3), and catechin-7-O- β-apiofuranoside (18) were active in HUVECs. In particular, Epifriedelanol (3) suppressed adriamycin-induced cellular senescence as well as replicative senescence in HDFs and HUVECs. These results suggest that Epifriedelanol (3) reduces cellular senescence in human primary cells and might be used to develop dietary supplements or cosmetics that modulate tissue aging or aging-associated diseases. Antitumor activity of epifriedelanol from Vitis trifolia.[Pubmed: 11449513]Fitoterapia. 2000 Sep;71(5):577-9.The isolation and NMR spectral data of Epifriedelanol from Vitis trifolia are reported. It demonstrated antitumor activity in a potato disc bioassay. Bioactive Constituents from the Rhizomes of Aster tataricus L. f. Afford the Treatment of Asthma through Activation of beta(2)AR and Inhibition of NF-kappa b[Reference: WebLink]Lat. Am. J. Pharm., 2015, 34(2):291-5.The rhizomes of Aster tataricus L. f. are used as materia medica or prescriptions for the treatment of asthma in Chinese folklore.
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| Kinase Assay | Potent protein tyrosine phosphatase 1B (PTP1B) inhibiting constituents from Anoectochilus chapaensis and molecular docking studies.[Pubmed: 25609152]Pharm Biol. 2015 Jan 22:1-5.Anoectochilus chapaensis Gagnep. (Orchidaceae), an indigenous and valuable Chinese folk medicine, has been used as an antidiabetic remedy. However, the bioactive constituents have not been reported.
To explore potent protein tyrosine phosphatase 1B (PTP1B) inhibitors from the whole herbs of A. chapaensis for the treatment of diabetes.
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| Structure Identification | J Asian Nat Prod Res. 2013 Sep;15(9):1050-4.A new cycloartane nortriterpenoid from stem and leaf of Quercus variabilis.[Pubmed: 23869388]
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Epifriedelanol Dilution Calculator
Epifriedelanol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3326 mL | 11.6632 mL | 23.3263 mL | 46.6527 mL | 58.3158 mL |
| 5 mM | 0.4665 mL | 2.3326 mL | 4.6653 mL | 9.3305 mL | 11.6632 mL |
| 10 mM | 0.2333 mL | 1.1663 mL | 2.3326 mL | 4.6653 mL | 5.8316 mL |
| 50 mM | 0.0467 mL | 0.2333 mL | 0.4665 mL | 0.9331 mL | 1.1663 mL |
| 100 mM | 0.0233 mL | 0.1166 mL | 0.2333 mL | 0.4665 mL | 0.5832 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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Potent protein tyrosine phosphatase 1B (PTP1B) inhibiting constituents from Anoectochilus chapaensis and molecular docking studies.[Pubmed:25609152]
Pharm Biol. 2015 Jul;53(7):1030-4.
CONTEXT: Anoectochilus chapaensis Gagnep. (Orchidaceae), an indigenous and valuable Chinese folk medicine, has been used as an antidiabetic remedy. However, the bioactive constituents have not been reported. OBJECTIVE: To explore potent protein tyrosine phosphatase 1B (PTP1B) inhibitors from the whole herbs of A. chapaensis for the treatment of diabetes. MATERIALS AND METHODS: The compounds were obtained by PTP1B bioactivity-guided isolation from the active fraction of ethonal extract of A. chapaensis, and elucidated by extensive spectroscopic methods and evaluated for their potential to inhibit PTP1B with a series of doses in dimethyl sulphoxide by a colorimetric assay in vitro. The Autodock program was used to dock the active compounds into the binding sites. RESULTS: Fifteen compounds were identified; Epifriedelanol, friedelane, 2alpha, 3beta-dihydroxyolean-12-en-23, 28, 30-trioic acid, dibutyl-phthalate, and 7-hydroxy-2-methoxy-9,10-dihydrophenanthrene-1,4-dione were isolated from the genera Anoectochilus for the first time. All 15 compounds were tested for their inhibitory activity against PTP1B in vitro. Nine active compounds exhibited potent inhibitory effect with IC50 values of 1.16-6.21 muM, which were comparable with the positive control suramin. The 3D-docking simulations showed negative binding energies of -7.4 to -8.5 kcal/mol and supported a high affinity to PTP1B residues in the pocket site, indicating that they may stabilize the open form and generate tighter binding to the catalytic sites of PTP1B. DISCUSSION AND CONCLUSION: The results clearly demonstrated that the potential active constituents from A. chapaensis could inhibit PTP1B, which may be mainly attributed to a combination of triterpenoids and flavonoids.
A new cycloartane nortriterpenoid from stem and leaf of Quercus variabilis.[Pubmed:23869388]
J Asian Nat Prod Res. 2013 Sep;15(9):1050-4.
A new compound 3-acetyloxy-epicycloeucalenol-24-one (1), with 11 known compounds 3alpha-acetyloxy-4alpha,14alpha-dimethyl-9beta,19-cycloergost-24-oic acid (2), 3-epicycloeucalenol (3), 3-epicycloeucalenyl-24-one (4), 3-epicycloeucalenyl acetate (5), 4beta,14alpha-dimethyl-5alpha-ergosta-9beta,19-cyclo-24(31)-en-3beta-hydroxy-4alp ha-carboxylic acid (6), cycloeucalenone (7), friedelin (8), Epifriedelanol (9), lup-20 (29)-en-3beta,30-diol (10), betulin (11), lupeol (12), was isolated from the stems and leaves of Quercus variabilis Blume. Seven compounds (1-7) showed anti-inflammatory activity.
Antitumor activity of epifriedelanol from Vitis trifolia.[Pubmed:11449513]
Fitoterapia. 2000 Sep;71(5):577-9.
The isolation and NMR spectral data of Epifriedelanol from Vitis trifolia are reported. It demonstrated antitumor activity in a potato disc bioassay.
Epifriedelanol from the root bark of Ulmus davidiana inhibits cellular senescence in human primary cells.[Pubmed:21049397]
Planta Med. 2011 Mar;77(5):441-9.
Since cellular senescence involves organismal aging as well as diverse diseases, aging intervention might contribute to inhibit the aging process as well as aging-associated diseases. We tried to search for effective compounds from the root bark of ULMUS DAVIDIANA that are able to inhibit cellular senescence in human fibroblasts (HDFs) and human umbilical vein endothelial cells (HUVECs). Twenty-two compounds from the root bark of U. DAVIDIANA were isolated and screened for their inhibitory effects on adriamycin-induced cellular senescence by measuring senescence-associated beta-galatosidase (SA- beta-gal) activity. Among twenty-two compounds isolated, Epifriedelanol (3), ssioriside (15), and catechin-7-O- beta-D-glucopyranoside (22) had inhibitory effects on adriamycin-induced cellular senescence in HDFs. Friedelin (2), Epifriedelanol (3), and catechin-7-O- beta-apiofuranoside (18) were active in HUVECs. In particular, Epifriedelanol (3) suppressed adriamycin-induced cellular senescence as well as replicative senescence in HDFs and HUVECs. These results suggest that Epifriedelanol (3) reduces cellular senescence in human primary cells and might be used to develop dietary supplements or cosmetics that modulate tissue aging or aging-associated diseases.
