The structure-antifungal activity relationship of 5,7-dihydroxyflavonoids against Penicillium italicum

Shuzhen Yang; Jie Zhou; Dongmei Li; Chunyu Shang; Litao Peng; Siyi Pan

doi:10.1016/j.foodchem.2016.12.001

The structure-antifungal activity relationship of 5,7-dihydroxyflavonoids against Penicillium italicum

Food Chem. 2017 Jun 1:224:26-31. doi: 10.1016/j.foodchem.2016.12.001. Epub 2016 Dec 9.

Authors

Shuzhen Yang¹, Jie Zhou², Dongmei Li³, Chunyu Shang⁴, Litao Peng⁵, Siyi Pan⁶

Affiliations

¹ Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: [email protected].
² Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: [email protected].
³ Georgetown University Medical Center, Washington, DC, USA. Electronic address: [email protected].
⁴ Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: [email protected].
⁵ Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: [email protected].
⁶ Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: [email protected].

PMID: 28159264
DOI: 10.1016/j.foodchem.2016.12.001

Abstract

To evaluate the structure-activity relationship of 5,7-dihydroxyflavonoids against P. italicum, we tested the antifungal activity of 23 selected 5,7-dihydroxyflavonoids against spore germination of P. italicum, and the effects of hydroxyl group, hydrogenation, methylation and glycosylation on the antifungal activity are explored. C-4'-OH and C-3-OH are active groups for the 5,7-dihydroxyflavonoids against P. italicum. We find that hydrogenation of the C2/C3 bond decreases the antifungal activity of 5,7-dihydroxyflavonoids. Antifungal activity of 5,7-dihydroxyflavonoids against P. italicum was affected by the conjugation site of glycosylation and the class of sugar moiety. The correlation between antifungal activity and the inhibition of respiration of 5,7-dihydroxyflavonoids was further evaluated. We find no significant relationship among the IC50 of 5,7-dihydroxyflavonoids on spore germination and on respiration. Some 5,7-dihydroxyflavonoids even enhance the respiration of P. italicum. This indicate respiration is not the only target for 5,7-dihydroxyflavonoids against P. italicum.

Keywords: 5,7-Dihydroxyflavonoids; P. italicum; Respiration; Spore germination; Structure-activity relationship.

MeSH terms

Antifungal Agents / chemistry*
Antifungal Agents / pharmacology
Flavonoids / chemistry*
Flavonoids / pharmacology
Glycosylation / drug effects
Penicillium / drug effects*
Structure-Activity Relationship

Substances

Antifungal Agents
Flavonoids