Panosialin wA
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02354 |
| CAS | |
| Molecular Weight | 400.57 |
| Molecular Formula | C21H36O5S |
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Description
It is produced by the strain of Str. sp OH-5186. It can inhibit α,β-glucosidase and mannose glycosidase. It does not inhibit the influenza virus, it has weak anti-microbial effect.
Specification
| IUPAC Name | [3-hydroxy-5-(13-methyltetradecyl)phenyl] hydrogen sulfate |
| Canonical SMILES | CC(C)CCCCCCCCCCCCC1=CC(=CC(=C1)OS(=O)(=O)O)O |
| InChI | InChI=1S/C21H36O5S/c1-18(2)13-11-9-7-5-3-4-6-8-10-12-14-19-15-20(22)17-21(16-19)26-27(23,24)25/h15-18,22H,3-14H2,1-2H3,(H,23,24,25) |
| InChI Key | SLCFAIQTHOPISH-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 176°C (dec.) |
| Solubility | Soluble in Methanol |
Reference Reading
1. New glycosidases inhibitors, panosialins D and wD produced by Streptomyces sp. OH-5186
H Yamada, K Shiomi, Q Xu, T Nagai, M Shibata, I Oya, Y Takahashi, S Omura J Antibiot (Tokyo). 1995 Mar;48(3):205-10. doi: 10.7164/antibiotics.48.205.
New panosialin analog, panosialins D and wD have been isolated from the culture broth of Streptomyces sp. OH-5186. Their structures were elucidated as 5-(13-methylpentadecyl)-1,3-benzenediol bis(sodium sulfate) and 5-(13-methylpentadecyl)-1,3-benzenediol 1-(sodium sulfate), respectively. They showed strong inhibitory activity against alpha-mannosidase, alpha-glucosidase, and beta-glucosidase. Panosialins wA-wD mixture also showed weak mitogenic activity but suppressed the mitogen induced activity.
2. Panosialins, inhibitors of enoyl-ACP reductase from Streptomyces sp. AN1761
Yun Ju Kwon, Mi-Jin Sohn, Taegwon Oh, Sang-Nae Cho, Chang-Jin Kim, Won-Gon Kim J Microbiol Biotechnol. 2013 Feb;23(2):184-8. doi: 10.4014/jmb.1209.09038.
In the continued search for inhibitors of enoyl-acyl carrier protein (ACP) reductase, we found that four acylbenzenediol sulfate metabolites from Streptomyces sp. AN1761 potently inhibited bacterial enoyl-ACP reductases of Staphylococcus aureus, Streptococcus pneumoniae, and Mycobacterium tuberculosis. Their structures were identified as panosialins A, B, wA, and wB by MS and NMR data. They showed stronger inhibition against S. aureus FabI and S. pneumoniae FabK with IC50 of 3-5 microM than M. tuberculosis InhA with IC50 of 9-12 microM. They also exhibited a stronger antibacterial spectrum on S. aureus and S. pneumoniae than M. tuberculosis. In addition, the higher inhibitory activity of panosialin wB than panosialin B on fatty acid biosynthesis was consistent with that on bacterial growth, suggesting that they could exert their antibacterial activity by inhibiting fatty acid synthesis.
3. Sulfotanone, a new alkyl sulfonic acid derivative from Streptomyces sp. IFM 11694 with TRAIL resistance-overcoming activity
Mohamed S Abdelfattah, Naoki Ishikawa, Utpal K Karmakar, Masami Ishibashi J Nat Med. 2016 Apr;70(2):266-70. doi: 10.1007/s11418-015-0951-3. Epub 2015 Nov 25.
One new alkyl sulfonic acid derivative, sulfotanone (1), and the known panosialin wA (2) were isolated from the methanolic extract of mycelium of Streptomyces sp. 11694. The structure of the new compound (1) was established by a combination of spectroscopic techniques, including HRESIMS, IR, 1D and 2D NMR measurements. Compound 1 (40 µM) in combination with TRAIL showed synergistic activity in sensitizing TRAIL-resistance in human gastric adenocarcinoma cell lines.
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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 ╳
