Alternariol
(Synonyms: 交链孢酚) 目录号 : GC10779
Alternariol是一种由链格孢菌（Alternaria）产生的霉菌毒素，在自然界中广泛存在，尤其在潮湿温暖环境下的谷物、水果和蔬菜中。Alternariol能够抑制拓扑异构酶I和IIα的催化活性，干扰DNA的正常功能，并具有细胞毒性、遗传毒性、诱变性及内分泌干扰作用。
Cas No.:641-38-3
Sample solution is provided at 25 µL, 10mM.
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Alternariol is a mycotoxin produced by Alternariafungi, which is widely distributed in nature, particularly in grains, fruits, and vegetables under warm and humid conditions[1]. Alternariol inhibits the catalytic activity of topoisomerase I and IIα, interferes with normal DNA function, and exhibits cytotoxicity, genotoxicity, mutagenicity, and endocrine-disrupting effects[2]. While demonstrating toxicity, Alternariol has also been found to possess various biological activities such as antimicrobial, anti-HIV, anticancer, and immunomodulatory properties[3-4].
In vitro, treatment of human colon adenocarcinoma Caco-2 cells with Alternariol (15–60μM) for 24–48 hours induced cell cycle arrest in the S and G2/M phases, accompanied by loss of mitochondrial membrane potential and necrotic/apoptotic cell death[5]. Treatment of mouse RAW 264.7 macrophages with Alternariol (15–30μM) for 24–48 hours resulted in G2/M phase cell cycle arrest, along with abnormal nuclear morphology and polyploid formation[6].
In vivo, a single topical application of Alternariol (12.5–50μg per mouse) to the skin of Swiss albino mice for 24 hours induced an increase in skin fold thickness, edema, epidermal hyperplasia, and inflammatory responses[7]. Dietary exposure of C57BL/6 mice to Alternariol (5–20μg/kg) for 90 days caused dose-dependent hepatotoxicity, characterized by an increased liver index, elevated serum ALT and AST levels, and histopathological alterations in liver tissue[8].
References:
[1] Siegel D, Troyanov S, Noack J, et al. Acta Crystallogr Sect E Struct Rep Online. 2010 May 15;66(Pt 6):o1366.
[2] Saleh I, Zeidan R, Abu-Dieyeh M. The characteristics, occurrence, and toxicological effects of alternariol: a mycotoxin. Arch Toxicol. 2024 Jun;98(6):1659-1683.
[3] Islam MT, Martorell M, González-Contreras C, et al. An updated overview of anticancer effects of alternariol and its derivatives: underlying molecular mechanisms. Front Pharmacol. 2023 Mar 23;14:1099380.
[4] Ding J, Zhao J, Yang Z, et al. Microbial Natural Product Alternariol 5-O-Methyl Ether Inhibits HIV-1 Integration by Blocking Nuclear Import of the Pre-Integration Complex. Viruses. 2017 May 10;9(5):105.
[5] Fernández-Blanco C, Juan-García A, Juan C, et al. Alternariol induce toxicity via cell death and mitochondrial damage on Caco-2 cells. Food Chem Toxicol. 2016 Feb;88:32-9.
[6] Solhaug A, Holme JA, Haglund K, et al. Alternariol induces abnormal nuclear morphology and cell cycle arrest in murine RAW 264.7 macrophages. Toxicol Lett. 2013 May 10;219(1):8-17.
[7] Bansal M, Singh N, Alam S, et al. Alternariol induced proliferation in primary mouse keratinocytes and inflammation in mouse skin is regulated via PGE2/EP2/cAMP/p-CREB signaling pathway. Toxicology. 2019 Jan 15;412:79-88.
[8] Yu S, Shen X, Huang Y, et al. Mycotoxin Alternariol Exposure Promotes Endoplasmic Reticulum Stress-induced Hepatotoxicity to Exacerbate Chronic Liver Injury. Environ Pollut. 2025 Oct 6:127217.
Alternariol是一种由链格孢菌（Alternaria）产生的霉菌毒素，在自然界中广泛存在，尤其在潮湿温暖环境下的谷物、水果和蔬菜中[1]。Alternariol能够抑制拓扑异构酶I和IIα的催化活性，干扰DNA的正常功能，并具有细胞毒性、遗传毒性、诱变性及内分泌干扰作用[2]。Alternariol在表现出毒性的同时，也被发现具有抗微生物、抗HIV、抗癌以及免疫调节等多种生物活性[3-4]。
在体外，Alternariol (15–60μM) 处理人结肠腺癌Caco-2细胞24–48小时，可诱导细胞周期阻滞于S期和G2/M期，并引发线粒体膜电位损失及细胞坏死/凋亡性死亡[5]。Alternariol（15–30μM）处理小鼠RAW 264.7巨噬细胞24–48小时，可诱导细胞周期阻滞于G2/M期，并伴随细胞核形态异常和多倍体形成[6]。
在体内，Alternariol（12.5–50μg/只）单次局部涂抹处理皮肤受损的Swiss albino mice 24小时，可诱导皮肤双褶厚度增加和水肿，并引发表皮增生及炎症反应[7]。Alternariol（5–20μg/kg）通过饮食暴露持续90天处理C57BL/6小鼠，可诱导剂量依赖性肝损伤，表现为肝脏指数升高、血清转氨酶（ALT/AST）水平增加及肝组织病理学改变[8]。
| Cell experiment [1]: | |
Cell lines | Caco-2 cells (human colon adenocarcinoma cell line) |
Preparation Method | Caco-2 cells were maintained in Dulbecco's Modified Eagle's Medium (DMEM) supplemented with 25mM HEPES buffer, 1% non-essential amino acids, 100U/mL penicillin, 100µg/mL streptomycin, and 10% fetal bovine serum at 37°C, 5% CO₂. Caco-2 cells were treated with Alternariol at sub-cytotoxic concentrations (15, 30, and 60µM) for 24 and 48 hours. |
Reaction Conditions | 15-60μM; 24-48 hours |
Applications | Alternariol significantly disrupted the cell cycle by decreasing the proportion of cells in the G1 phase and increasing accumulation in the S and G2/M phases in a dose- and time-dependent manner. Alternariol also induced necrosis and apoptosis/necrosis, as evidenced, and caused a loss of mitochondrial membrane potential indicating mitochondrial damage. |
| Animal experiment [2]: | |
Animal models | C57BL/6 mice |
Preparation Method | Male C57BL/6 mice (4-week-old) were fed a diet containing Alternariol (AOH) at doses of 5, 10, and 20µg/kg daily for 90 days. A separate intervention group received co-administration of Alternariol (10µg/kg) with Tauroursodeoxycholic acid (TUDCA, 500mg/kg) via drinking water. Mice were sacrificed after 90 days of exposure for analysis. |
Dosage form | 5, 10, and 20mg/kg; dietary administration. |
Applications | Alternariol exposure induced dose-dependent hepatotoxicity characterized by increased liver index, elevated serum ALT and AST levels, and histopathological liver injury including parenchymal congestion, sinusoidal dilatation, and inflammatory cell infiltration. |
References: | |
| Cas No. | 641-38-3 | SDF | |
| 别名 | 交链孢酚 | ||
| 化学名 | 3,7,9-trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one | ||
| Canonical SMILES | CC1=C(C2=C(C(O3)=O)C(O)=CC(O)=C2)C3=CC(O)=C1 | ||
| 分子式 | C14H10O5 | 分子量 | 258.2 |
| 溶解度 | ≤0.5mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide | 储存条件 | Store at -20°C,protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.873 mL | 19.3648 mL | 38.7297 mL |
| 5 mM | 774.6 μL | 3.873 mL | 7.7459 mL |
| 10 mM | 387.3 μL | 1.9365 mL | 3.873 mL |
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| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
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2.
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