| Identification | Back Directory | [Name]
ZARAGOZIC ACID A | [CAS]
142561-96-4 | [Synonyms]
Aids111671
Gr 105155x
Aids-111671
Squalestatin 1
ZARAGOZIC ACID A
DFKDOZMCHOGOBR-NCSQYGPNSA-N
Squalestatin A, Squalestatin S1, L 694599
L-Erythro-L-glycero-D-altro-7-trideculo-7,4-furanosonic acid, 2,7-anhydro-3,4-di-C-carboxy-8,9,10,12,13-pentadeoxy-10-methylene-12-(phenylmethyl)-, 11-acetate 5-[(2E,4S,6S)-4,6-dimethyl-2-octenoate], (7S)- | [Molecular Formula]
C39H54O13 | [MDL Number]
MFCD00868072 | [MOL File]
142561-96-4.mol | [Molecular Weight]
730.843 |
| Chemical Properties | Back Directory | [alpha ]
D22 +18.3° (c = 0.60 in CHCl3); D25 +37° (c = 1.29 in methanol) | [Boiling point ]
850.1±65.0 °C(Predicted) | [density ]
1.35±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in DMSO | [form ]
solid | [pka]
1.47±0.70(Predicted) | [color ]
white to light tan | [CAS DataBase Reference]
142561-96-4 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light tan solid. Soluble in ethanol (10 mg/ml), methanol, DMF, DMSO (10 mg/ml), and water (moderate). | [Uses]
Zaragozic acid A is the major metabolite of a class of unusual bicyclic tricarboxylic acids, produced by a number of fungi in the genera Curvularia, Exserohilum, Setosphaeria and others, discovered at Merck and Glaxo in the early 1990s. In nature, zaragozic acid A acts as broad spectrum antifungal but its mode of action as an inhibitor of squalene synthase, involved in sterol biosynthesis, lead to investigation as a cholesterol lowering agent. Zaragozic acid A prepared by BioAustralis is presented as the free acid rather than the tri-sodium salt to avoid stability problems associated with hydrolysis of the salt. | [Application]
Zaragozic Acid A is a squalene synthetase inhibitor. it targeted squalene synthase and lowered the cholesterol levels in vivo of marmosets. | [Definition]
ChEBI: Zaragozic acid A is a polyketide isolated from fungi that is a potent inhibitor of fungal and mammalian squalene synthase. It has a role as an EC 2.5.1.21 (squalene synthase) inhibitor and a fungal metabolite. It is a tricarboxylic acid, an acetate ester, a cyclic ketal, an oxabicycloalkane, a tertiary alcohol and a polyketide. | [Biological Activity]
Zaragozic acid A is an inhibitor of acute liver cholsterol synthesis (50% inhibition dose 200 μg/ kg) with Ki value of 78pM. It inhibited cholesterol synthesis in Hep G2 cells. | [in vitro]
zaragozic acid a, as well as it two analogs zaragozic acid b and c were discovered from an unidentified sterile fungal culture, spororniella intermedia, and leptodontium elatius, respectively. zaragozic acid a, b and c were reported to be three potent competitive inhibitors of rat liver squalene synthase with ki values of 78 pm, 29 pm, and 45 pm, respectively. in addition, zaragozic acid a, b and c could also inhibite cholesterol synthesis in hep g2 cells [1]. | [in vivo]
in the mouse model, zaragozic acid a was found to be an inhibitor of acute hepatic cholesterol synthesis (50% inhibitory dose of 200 μg/kg). the in-vivo inhibition of squalene synthase was accompanied by an accumulation of label from [3hjmevalonate into farnesyl diphosphate, farnesol, as well as organic acids. in summary, these data showed the zaragozic acids were a new class of therapeutic agents with potential for the hypercholesterolemia treatment [1]. | [storage]
Store at -20°C,protect from light | [References]
[1] bergstrom jd,kurtz mm,rew dj,amend am,karkas jd,bostedor rg,bansal vs,dufresne c,vanmiddlesworth fl,hensens od, et al. zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase. proc natl acad sci u s a.1993 jan 1;90(1):80-4. |
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