Polyporenic acid C
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| Category | Antibiotics |
| Catalog number | BBF-02582 |
| CAS | 465-18-9 |
| Molecular Weight | 482.69 |
| Molecular Formula | C31H46O4 |
| Purity | >98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-02582 | 5 mg | $729 | In stock |
Online Inquiry
Add to cartDescription
Polyporenic acid C is a steroid antibiotic produced by Polyporus betulinus and Polyporus benzoinus. It has strong anti-mycobacterial activity and weak anti-gram-negative bacteria activity.
Specification
| Synonyms | (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid |
| IUPAC Name | (2R)-2-[(5R,10S,13R,14R,16R,17R)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid |
| Canonical SMILES | CC(C)C(=C)CCC(C1C(CC2(C1(CC=C3C2=CCC4C3(CCC(=O)C4(C)C)C)C)C)O)C(=O)O |
| InChI | InChI=1S/C31H46O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h11,13,18,20,23-24,26,32H,3,9-10,12,14-17H2,1-2,4-8H3,(H,34,35)/t20-,23-,24+,26+,29-,30-,31+/m1/s1 |
| InChI Key | KPKYWYZPIVAHKU-WMNQUVFJSA-N |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria; mycobacteria |
| Boiling Point | 620.3±55.0°C at 760 mmHg |
| Melting Point | 273-276°C |
| Density | 1.1±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1.Inhibition of tumor-promoting effects by poricoic acids G and H and other lanostane-type triterpenes and cytotoxic activity of poricoic acids A and G from Poria cocos.
Ukiya M;Akihisa T;Tokuda H;Hirano M;Oshikubo M;Nobukuni Y;Kimura Y;Tai T;Kondo S;Nishino H J Nat Prod. 2002 Apr;65(4):462-5.
The structures of two novel 3,4-seco-lanostane-type triterpenes isolated from the sclerotium of Poria cocos were established to be 16alpha-hydroxy-3,4-seco-lanosta-4(28),8,24-triene-3,21-dioic acid (1; poricoic acid G) and 16alpha-hydroxy-3,4-seco-24-methyllanosta-4(28),8,24(24(1))-triene-3,21-dioic acid (2; poricoic acid H) on the basis of spectroscopic methods. These two, and eight other known compounds isolated from the sclerotium, poricoic acid B (3), poricoic acid A (4), tumulosic acid (5), dehydrotumulosic acid (6), 3-epidehydrotumulosic acid (7), polyporenic acid C (8), 25-hydroxy-3-epidehydrotumulosic acid (9), and dehydroabietic acid methyl ester (10), showed potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). Evaluation of the cytotoxicity of compounds 1 and 4 against human cancer cell lines revealed that 1 was significantly cytotoxic to leukemia HL-60 cells [GI(50) (concentration that yields 50% growth) value 39.
2.Two new lanostane triterpenoids from Poria cocos.
Zheng Y;Yang XW J Asian Nat Prod Res. 2008 Mar-Apr;10(3-4):323-8. doi: 10.1080/10286020801892250.
Two new lanostane triterpenoids, 29-hydroxypolyporenic acid C (4) and 25-hydroxypachymic acid (5), together with three known compounds, ergosta-7,22-dien-3beta-ol (1), polyporenic acid C (2) and pachymic acid (3), were isolated from the 95% ethanolic extract of the sclerotium of Poria cocos (Schw.) Wolf. Their structures were determined by extensive spectroscopic analyses, including IR, UV, ESITOF-MS, HRESI-MS, 1D and 2D NMR data (1H NMR, 13C NMR, 1H-1H COSY, NOESY, HSQC and HMBC).
3.Triterpenes from the fungus Poria cocos and their inhibitory activity on nitric oxide production in mouse macrophages via blockade of activating protein-1 pathway.
Cai TG;Cai Y Chem Biodivers. 2011 Nov;8(11):2135-43. doi: 10.1002/cbdv.201100013.
Two new triterpenes, 29-hydroxydehydrotumulosic acid (1) and 29-hydroxydehydropachymic acid (2), together with six known compounds, dehydropachymic acid (3), dehydrotumulosic acid (4), 29-hydroxypolyporenic acid C (5), polyporenic acid C (6), tumulosic acid (7), and pachymic acid (8), were isolated from the dried sclerotia of Poria cocos. In the in vitro bioassays, these isolated compounds reduced, in a dose-dependent manner, nitric oxide (NO) production from lipopolysaccharide (LPS)-induced RAW 264.7 cells, with compounds 5 and 6, the IC(50) values of which were 16.8±2.7 and 18.2±3.3 μM, respectively, exhibiting the greatest inhibition activity. Further Western blot analysis conducted on cells pre-treated with compounds 5 and 6, and luciferase assays on activator protein 1-dependent gene expression revealed that the inhibited NO release was attributed to the reduced expression of iNOs (=inducible NO synthase) enzymes, which might be regulated via the blockade of activator protein-1 signaling pathway.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
