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Protective effects of apigenin, apigenin-8-sulfonate, and apigenin-3′, 8-disulfonate on d-galactosamine-induced acute liver damage in mice

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Abstract

The water-soluble sulfated derivatives, apigenin-8-sulfonate sodium (AS) and apigenin-3′, 8-disulfonate sodium (ADS) derived from parent apigenin (AP), were synthesized and characterized by infrared (IR) spectra, hydrogen nuclear magnetic resonance (1H NMR), carbon nuclear magnetic resonance (13C NMR), high-resolution mass spectra (HRMS), and elemental analysis. The mice model of hepatotoxicity induced by d-Galactosamine (d-GalN) was used to evaluate the hepatoprotective effects of AP, AS, and ADS. The results indicated that AP, AS, and ADS could reduce the level of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), and hepatic malondialdehyde (MDA) induced by d-GalN, and restore the activities of antioxidant enzymes superoxide dismutase (SOD), glutathione peroxidase (GSH-Px), and catalase (CAT) toward normal levels. The histological results also suggested that AP, AS, and ADS could alleviate liver toxicity. The possible mechanisms could be ascribed to the protection role of AP, AS, and ADS, which kept hepatic cells from oxidative damage and maintain intracellular antioxidant enzyme activity. These findings uncovered that AP, AS, and ADS were able to protect liver from d-GalN-induced acute damage, and AS was the most potent hepatoprotective drug among the three compounds.

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Abbreviations

AP:

apigenin

ADS:

apigenin-3′, 8-disulfonate sodium

ALT:

alanine aminotransferase

AS:

apigenin-8-sulfonate sodium

AST:

aspartate aminotransferase

CAT:

catalase

CNMR:

Carbon nuclear magnetic resonance

d-GalN:

d-Galactosamine

HNMR:

Hydrogen nuclear magnetic resonance

GSH-Px:

glutathione peroxidase

MDA:

malondialdehyde

PBS:

phosphate-buffered saline

SOD:

superoxide dismutase

IR:

infrared

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Acknowledgements

This study was financially supported by the National Science Foundation of China (No. 21362026).

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Authors and Affiliations

  1. Rongchang Campus, Southwest University, Chongqing, 402460, PR China

    Xin-Bin Yang

  2. Pharmacy College, Ningxia Medical University, Yinchuan, 750004, PR China

    Yu Huang

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  1. Xin-Bin Yang
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Correspondence to Xin-Bin Yang.

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Yang, XB., Huang, Y. Protective effects of apigenin, apigenin-8-sulfonate, and apigenin-3′, 8-disulfonate on d-galactosamine-induced acute liver damage in mice. Med Chem Res 29, 1867–1873 (2020). https://doi.org/10.1007/s00044-020-02608-2

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