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Glisoprenin B

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Glisoprenin B
Category Enzyme inhibitors
Catalog number BBF-01254
CAS 144376-63-6
Molecular Weight 719.13
Molecular Formula C45H82O6

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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 Gliocladium sp. FO-1513. It is a cholesterol acyltransferase (ACAT) inhibitor.

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Synonyms 2,6,10,14-Tricosatetraene-1,19,23,27-tetrol,3,7,11,15,19,23,27-heptamethyl-30-(tetrahydro-5-(1-hydroxy-1-methylethyl)-2-methyl-2-furanyl)-
IUPAC Name (2E,6E,10E,14E)-30-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3,7,11,15,19,23,27-heptamethyltriaconta-2,6,10,14-tetraene-1,19,23,27-tetrol
Canonical SMILES CC(=CCCC(=CCCC(=CCCC(=CCO)C)C)C)CCCC(C)(CCCC(C)(CCCC(C)(CCCC1(CCC(O1)C(C)(C)O)C)O)O)O
InChI InChI=1S/C45H82O6/c1-36(18-11-19-37(2)21-13-23-39(4)26-35-46)20-12-22-38(3)24-14-27-42(7,48)28-15-29-43(8,49)30-16-31-44(9,50)32-17-33-45(10)34-25-40(51-45)41(5,6)47/h18,21-22,26,40,46-50H,11-17,19-20,23-25,27-35H2,1-10H3/b36-18+,37-21+,38-22+,39-26+
InChI Key JVMGRPXMVYGAQN-QYOQUFJESA-N
Appearance Colorless Oily Matter
Boiling Point 790.2±60.0 °C (Predicted)
Density 0.992±0.06 g/cm3 (Predicted)
Solubility Soluble in Methanol, Chloroform
1. Glisoprenins, new inhibitors of acyl-CoA: cholesterol acyltransferase produced by Gliocladium sp. FO-1513. I. Production, isolation and physico-chemical and biological properties
H Tomoda, X H Huang, H Nishida, R Masuma, Y K Kim, S Omura J Antibiot (Tokyo). 1992 Aug;45(8):1202-6. doi: 10.7164/antibiotics.45.1202.
Gliocladium sp. FO-1513 was found to produce novel inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT). Two active compounds, designated glisoprenins A and B, were isolated from the culture broth of the producing strain by a conventional method. The IC50 values of glisoprenins A and B for ACAT activity were 46 and 61 microM in an enzyme assay using rat liver microsomes, and 1.2 and 0.57 microM in a J774 macrophage assay, respectively.
2. Glisoprenins, new inhibitors of acyl-CoA: cholesterol acyltransferase produced by Gliocladium sp. FO-1513. II. Structure elucidation of glisoprenins A and B
H Nishida, X H Huang, H Tomoda, S Omura J Antibiot (Tokyo). 1992 Oct;45(10):1669-76. doi: 10.7164/antibiotics.45.1669.
The structure of glisoprenins A and B, novel acyl-CoA: cholesterol acyltransferase (ACAT) inhibitors, was determined by spectroscopic analyses, mainly 1H and 13C NMR and MS. Glisoprenin A was deduced to be a tetrahydroxynonaprenol and glisoprenin B to be an oxidative modification of glisoprenin A.

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