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Panosialin B

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Category Enzyme inhibitors
Catalog number BBF-03747
CAS
Molecular Weight 480.63
Molecular Formula C21H36O8S2

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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, but it has weak anti-microbial effect.

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Synonyms 5-Pentadecylresorcinol 1,3-bissulfuric acid; Panosialin II; Panosialin-IA; Resorcinol, 5-pentadecyl-, disulfate (ester); 5-Pentadecyl-1,3-phenylenbis(hydrogensulfat)
IUPAC Name (3-pentadecyl-5-sulfooxyphenyl) hydrogen sulfate
Canonical SMILES CCCCCCCCCCCCCCCC1=CC(=CC(=C1)OS(=O)(=O)O)OS(=O)(=O)O
InChI InChI=1S/C21H36O8S2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(28-30(22,23)24)18-21(17-19)29-31(25,26)27/h16-18H,2-15H2,1H3,(H,22,23,24)(H,25,26,27)
InChI Key USQVRFZEIYYKND-UHFFFAOYSA-N
Appearance White Powder
Density 1.2±0.1 g/cm3
Solubility Soluble in Methanol
1. Panosialins, inhibitors of an alpha1,3-fucosyltransferase Fuc-TVII, suppress the expression of selectin ligands on U937 cells
K Shinoda, K Shitara, Y Yoshihara, A Kusano, Y Uosaki, S Ohta, N Hanai, I Takahashi Glycoconj J. 1998 Nov;15(11):1079-83. doi: 10.1023/a:1006953626578.
Panosialins A and B were isolated as inhibitors of an alpha1,3-fucosyltransferase, Fuc-TVII, which is a key enzyme in the biosynthesis of selectin ligands, from culture broth of Streptomyces sp. Panosialins A and B inhibited the Fuc-TVII activity with IC50 values of 4.8 and 5.3 microg/ml, respectively. Panosialin A suppressed expression of selectin ligands on U937 cells, and inhibited the cell adhesion to immobilized E-selectin-immunoglobulin. Panosialins are the first reported Fuc-TVII inhibitors which can suppress the biosynthesis of selectin ligands and then inhibit selectin-mediated cell adhesion.
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.
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