Names | |
---|---|
Preferred IUPAC name
(1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(Acetyloxy)-5-methyl-3-methylidene-6-phenylhexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid | |
Other names
Squalestatin 1
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C35H46O14 | |
Molar mass | 690.73134 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Zaragozic acids are a family of natural products produced by fungi. The first characterized zaragozic acids, A, B, and C were isolated from an unidentified sterile fungal culture, Sporormiella intermedia, and L. elatius, respectively. [1] just outside the European city Zaragoza, Spain on the Jalón river. This family of natural products possesses a unique 4,8-dioxabicyclo[3.2.1]octane core, and vary in their 1-alkyl and their 6-acyl side chains. [2]
Zaragozic acids are potent inhibitors of S. cervisiae, fungal and mammalian squalene synthase and therefore inhibitors of sterol synthesis. [2] Squalene synthase is the first committed enzyme in sterol synthesis, catalyzing the reductive condensation of farnesyl pyrophosphate to form squalene. [3] As a squalene synthase inhibitor, zaragozic acid produces lower plasma cholesterol levels in primates. [2] Treatment of rats with zaragozic acid A caused an increase in hepatic low density lipoprotein (LDL) receptor mRNA levels. [4]
Zaragozic acids also mildly inhibit Ras farnesyl-protein transferase. [5]
Zaragozic acid D and D2 have been isolated from the keratinophilic fungus Amauroascus niger. [5]
The core biosynthetic route is via a polyketide synthase pathway from 10 acetates, 4 methyls of methionines, 1 succinate, and 1 benzoic acid. [6]
Names | |
---|---|
Preferred IUPAC name
(1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-(Acetyloxy)-5-methyl-3-methylidene-6-phenylhexyl]-6-{[(2E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy}-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid | |
Other names
Squalestatin 1
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C35H46O14 | |
Molar mass | 690.73134 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Zaragozic acids are a family of natural products produced by fungi. The first characterized zaragozic acids, A, B, and C were isolated from an unidentified sterile fungal culture, Sporormiella intermedia, and L. elatius, respectively. [1] just outside the European city Zaragoza, Spain on the Jalón river. This family of natural products possesses a unique 4,8-dioxabicyclo[3.2.1]octane core, and vary in their 1-alkyl and their 6-acyl side chains. [2]
Zaragozic acids are potent inhibitors of S. cervisiae, fungal and mammalian squalene synthase and therefore inhibitors of sterol synthesis. [2] Squalene synthase is the first committed enzyme in sterol synthesis, catalyzing the reductive condensation of farnesyl pyrophosphate to form squalene. [3] As a squalene synthase inhibitor, zaragozic acid produces lower plasma cholesterol levels in primates. [2] Treatment of rats with zaragozic acid A caused an increase in hepatic low density lipoprotein (LDL) receptor mRNA levels. [4]
Zaragozic acids also mildly inhibit Ras farnesyl-protein transferase. [5]
Zaragozic acid D and D2 have been isolated from the keratinophilic fungus Amauroascus niger. [5]
The core biosynthetic route is via a polyketide synthase pathway from 10 acetates, 4 methyls of methionines, 1 succinate, and 1 benzoic acid. [6]