The structure-antifungal activity relationship of 5,7-dihydroxyflavonoids against Penicillium italicum.
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.
Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: yszhen@mail.hzau.edu.cn.
Shuzhen
S
Yang
Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: 631458741@qq.com.
Jie
J
Zhou
Georgetown University Medical Center, Washington, DC, USA. Electronic address: daisyallen2008@163.com.
Dongmei
D
Li
Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: 897080430@qq.com.
Chunyu
C
Shang
Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: penglt12@mail.hzau.edu.cn.
Litao
L
Peng
Key Laboratory of Environment Correlative Dietology, Ministry of Education, College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, PR China. Electronic address: pansiyi@mail.hzau.edu.cn.
Siyi
S
Pan
D000935:Antifungal Agents / Q000737:chemistry* / Q000494:pharmacology; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology; D006031:Glycosylation / Q000187:drug effects; D010407:Penicillium / Q000187:drug effects*; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D005419:Flavonoids
5,7-Dihydroxyflavonoids; P. italicum; Respiration; Spore germination; Structure-activity relationship