1. Cell Cycle/DNA Damage Vitamin D Related/Nuclear Receptor Apoptosis
  2. Topoisomerase Androgen Receptor Estrogen Receptor/ERR Apoptosis
  3. Alternariol

Alternariol is an orally ingested mycotoxin produced by Alternaria, capable of inhibiting the activity of topoisomerase I and II (topoisomerase I, topoisomerase II). Alternariol has weak estrogenic (Estrogen Receptor/ERR) and androgen/antiandrogen (Androgen Receptor) effects. Alternariol can induce apoptosis, trigger cell cycle arrest, suppress innate immune responses, and exhibit anti-tumor activity. Alternariol has genotoxic, mutagenic, and endocrine-disrupting effects.

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Alternariol Chemical Structure

Alternariol Chemical Structure

CAS No. : 641-38-3

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Based on 1 publication(s) in Google Scholar

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  • Biological Activity

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Description

Alternariol is an orally ingested mycotoxin produced by Alternaria, capable of inhibiting the activity of topoisomerase I and II (topoisomerase I, topoisomerase II). Alternariol has weak estrogenic (Estrogen Receptor/ERR) and androgen/antiandrogen (Androgen Receptor) effects. Alternariol can induce apoptosis, trigger cell cycle arrest, suppress innate immune responses, and exhibit anti-tumor activity. Alternariol has genotoxic, mutagenic, and endocrine-disrupting effects[1][2][3][4][5].

Cellular Effect
Cell Line Type Value Description References
A2780 IC50
> 10 μM
Compound: 12
Cytotoxicity against human A2780 cells by MTT assay
Cytotoxicity against human A2780 cells by MTT assay
[PMID: 27441892]
BGC-823 IC50
> 10 μM
Compound: 12
Cytotoxicity against human BGC823 cells by MTT assay
Cytotoxicity against human BGC823 cells by MTT assay
[PMID: 27441892]
HCT-116 IC50
> 10 μM
Compound: 12
Cytotoxicity against human HCT116 cells by MTT assay
Cytotoxicity against human HCT116 cells by MTT assay
[PMID: 27441892]
HepG2 IC50
> 10 μM
Compound: 12
Cytotoxicity against human HepG2 cells by MTT assay
Cytotoxicity against human HepG2 cells by MTT assay
[PMID: 27441892]
HT-29 IC50
> 20 μM
Compound: 17
Cytotoxicity against human HT-29 cells after 3 days by sulforhodamine B assay
Cytotoxicity against human HT-29 cells after 3 days by sulforhodamine B assay
[PMID: 28409637]
L5178Y EC50
1.7 μg/mL
Compound: 1
Cytotoxicity against mouse L5178Y cells by MTT assay
Cytotoxicity against mouse L5178Y cells by MTT assay
[PMID: 18494522]
MCF7 IC50
> 20 μM
Compound: 17
Cytotoxicity against human MCF7 cells after 3 days by sulforhodamine B assay
Cytotoxicity against human MCF7 cells after 3 days by sulforhodamine B assay
[PMID: 28409637]
NCI-H1650 IC50
> 10 μM
Compound: 12
Cytotoxicity against human NCI-H1650 cells by MTT assay
Cytotoxicity against human NCI-H1650 cells by MTT assay
[PMID: 27441892]
RAW264.7 IC50
51.4 μM
Compound: 14
Antiinflammatory activity in mouse RAW 264.7 cells assessed as inhibition of LPS-induced nitric oxide production measured after 24 hrs by Griess reagent assay
Antiinflammatory activity in mouse RAW 264.7 cells assessed as inhibition of LPS-induced nitric oxide production measured after 24 hrs by Griess reagent assay
[PMID: 35007071]
In Vitro

Alternariol (10 μM, 24 h) inhibits the innate immune response of human lung epithelial cells (BEAS-2B) and mouse macrophages (RAW264.7)[2].
Alternariol (5-10 μM, 24 h) dose-dependently reduces inflammation in BEAS-2B cells induced by LPS (HY-D1056, 10 µg) [2].
Alternariol (1-100 μM, 24 h) inhibits the proliferation of BEAS-2B cells and induces cell cycle arrest[2].
Alternariol (10 μM, 24 h) induces HPRT and TK mutations in V79 cells and mouse lymphoma L5178Y tk+/− cells (MLC)[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Real Time qPCR[2]

Cell Line: BEAS-2B, RAW264.7 (induced by LPS)
Concentration: 10 μM
Incubation Time: 24 h
Result: Reduced IL6, IL8, MCP-1/CCL2 levels, induced cytochrome P450 CYP1A1 gene expression, and partially prevented LPS-induced downregulation.

Cell Viability Assay[2]

Cell Line: BEAS-2B
Concentration: 1, 5, 10, 15, 20, 25, 30, 50, 100 μM
Incubation Time: 24 h
Result: Inhibited cell proliferation, but not cell death.
In Vivo

Alternariol (1-5 mg/kg, intravenous injectionon, daily, 4 days) has embryotoxic and immunotoxic effects during the embryonic and infant developmental stages in mice, inducing apoptosis[4].
Alternariol (50-200 mg/kg, orally, once daily, 24 weeks) induces cell death and inhibits cell proliferation in DMBA (HY-W011845) induced breast cancer in mice, significantly suppressing breast cancer[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: Pregnant mice[4]
Dosage: 1, 3, 5 mg/kg; daily; 4 days
Administration: Intravenous injection (i.v.)
Result: Showed embryonic apoptosis at the blastocyst stage, fetal weight loss, triggering a significant increase in total oxidative stress content and expression of genes encoding antioxidant proteins, and reducing the expression of CXCL1, IL-1β and IL-8.
Animal Model: Mice induced by DMBA(HY-W011845)[5]
Dosage: 50, 100, 200 mg/kg; daily; 24 weeks
Administration: Oral
Result: Reduced proliferative lesions of breast tissue, restored normal histopathological characteristics of breast tissue, downregulated the expression of oncogenic markers such as PI3K and Akt, increased the expression of apoptosis markers such as p53, caspase-3 and Bax, reduced cell proliferation and increased cell apoptosis.
Molecular Weight

258.23

Formula

C14H10O5

CAS No.
Appearance

Solid

Color

White to light brown

SMILES

CC1=CC(O)=CC(O2)=C1C3=CC(O)=CC(O)=C3C2=O

Structure Classification
Initial Source

fungi of the genus Alternaria

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

*In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility
In Vitro: 

DMSO : ≥ 30 mg/mL (116.18 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.8725 mL 19.3626 mL 38.7252 mL
5 mM 0.7745 mL 3.8725 mL 7.7450 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

  • Molarity Calculator

  • Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

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Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Calculation results:
Working solution concentration: mg/mL
Purity & Documentation

Purity: 99.67%

References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 3.8725 mL 19.3626 mL 38.7252 mL 96.8129 mL
5 mM 0.7745 mL 3.8725 mL 7.7450 mL 19.3626 mL
10 mM 0.3873 mL 1.9363 mL 3.8725 mL 9.6813 mL
15 mM 0.2582 mL 1.2908 mL 2.5817 mL 6.4542 mL
20 mM 0.1936 mL 0.9681 mL 1.9363 mL 4.8406 mL
25 mM 0.1549 mL 0.7745 mL 1.5490 mL 3.8725 mL
30 mM 0.1291 mL 0.6454 mL 1.2908 mL 3.2271 mL
40 mM 0.0968 mL 0.4841 mL 0.9681 mL 2.4203 mL
50 mM 0.0775 mL 0.3873 mL 0.7745 mL 1.9363 mL
60 mM 0.0645 mL 0.3227 mL 0.6454 mL 1.6135 mL
80 mM 0.0484 mL 0.2420 mL 0.4841 mL 1.2102 mL
100 mM 0.0387 mL 0.1936 mL 0.3873 mL 0.9681 mL
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Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Alternariol
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