b-Zearalanol

Names

[ Name ]:
b-Zearalanol

[Synonym ]:
|A-Zearanol
Taleranol
(6S,10S)-6-(6,10-Dihydroxyundecyl)-b-resorcyclic acid m-lactone
1H-2-Benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10,11,12-decahydro-7,14,16-trihydroxy-3-methyl-, (3S,7S)-
|A-Zearalanol
Taleranolum
|A-Zeranol
(6S,10S)-6-(6,10-Dihydroxyundecyl)-β-resorcyclic acid μ-lactone
β-Zearalanol
β zearalanol
b-Zearalanol
(3S,7S)-3,4,5,6,7,8,9
(3S,7S)-3,4,5,6,7,8,9,10,11,12-Decahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one
(3S,7S)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one
[3S-(3R*,7R*)]-3,4,5,6,7,8,9,10,11,12-Decahydro-7,14,16-trihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1-one

Biological Activity

[Description]:

Beta-zearalenol is an mycotoxin produced by Fusarium spp, which causes apoptosis and oxidative stress in mammalian reproductive cells[1]. Beta-zearalenol is the derivative of zearalenone (ZEA) which can conjugate with glucuronic acid[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Metabolic Disease

[In Vitro]

βeta-zearalenol (0-200 μM; 24 hours) inhibits BGC proliferation in a dose-dependent manner, with an IC50 of 25 μM[1]. βeta-Zearalenol (0-100 μM; 72 hours) shows high toxic with an IC50 of 15.2 μM in the HepG2 cells, synergistic effect of β-ZOL+ZEN or β-ZOL+α-ZOL with IC50 values of 19.8 uM, 16.8 uM, respectively[2]. βeta-Zearalenol (0-10 μM; 72 hours) has the highest inhibition effect on the all three investigated cytokines: IL-8, IL-1β and TNF-α by comparation with ZEA or α-Zearalenol[2]. Cell Viability Assay[2] Cell Line: HepG2 cells Concentration: 0–100 μM Incubation Time: 72 hours Result: Shown a dose-dependent reduction of viability of cells treated with β-ZOL. Cell Proliferation Assay[1] Cell Line: BGC cells Concentration: 0 μM, 5 μM, 10 μM, 15 μM, 25 μM, 50 μM, 100 μM, and 200 μM Incubation Time: 24 hours Result: Inhibited cell proliferation in a dose-dependent manner. RT-PCR[2] Cell Line: HepG2 cells Concentration: 1 μM, 5 μM, 10 μM Incubation Time: 72 hours Result: Had the higher cytotoxic effect in comparation with α-Zearalenol.

[References]

[1]. Yang F, et al. Melatonin alleviates β-zearalenol and HT-2 toxin-induced apoptosis and oxidative stress in bovine ovarian granulosa cells. Environ Toxicol Pharmacol. 2019 May;68:52-60.

[2]. Marin DE, et al. Cytotoxic and inflammatory effects of individual and combined exposure of HepG2 cells to zearalenone and its metabolites. Naunyn Schmiedebergs Arch Pharmacol. 2019 Aug;392(8):937-947.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
576.0±50.0 °C at 760 mmHg

[ Melting Point ]:
134-137ºC

[ Molecular Formula ]:
C₁₈H₂₆O₅

[ Molecular Weight ]:
322.396

[ Flash Point ]:
207.9±23.6 °C

[ Exact Mass ]:
322.178009

[ PSA ]:
86.99000

[ LogP ]:
3.86

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.536

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H319-H335-H360

[ Precautionary Statements ]:
P201-P261-P305 + P351 + P338-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T,Xn,F

[ Risk Phrases ]:
60-36/37/38

[ Safety Phrases ]:
53-36/37/39-45

[ RIDADR ]:
UN 1648 3 / PGII

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Determination of resorcylic acid lactones in biological samples by GC-MS. Discrimination between illegal use and contamination with fusarium toxins.

Anal. Bioanal. Chem 384(5) , 1221-7, (2006)

An EU project, FAIR5-CT-1997-3443, has been undertaken to distinguish illegal use of zeranol from consumption of food contaminated with Fusarium spp. toxin. One of the tasks was development of screeni...

Cytosol protein regulation in H295R steroidogenesis model induced by the zearalenone metabolites, α- and β-zearalenol.

Toxicon 59(1) , 17-24, (2012)

α- and β-zearalenol (α-ZOL and β-ZOL, respectively) are metabolites of the mycotoxin zearalenone (ZEN). All three individual mycotoxins have shown to be biological active i.e. being estrogenic and abl...

Determination of the cross-reactivities for alpha-zearalenol, beta-zearalenol, zearalanone, alpha-zearalanol, and beta-zearalanol on three commercial immunoaffinity columns targeting zearalenone.

J. AOAC Int. 90(4) , 1197-202, (2007)

Immunoaffinity extraction has become increasingly important as a sample preparation and cleanup method in mycotoxin analysis. In this study, the antibody specificities of 3 commercial immunoaffinity c...