| RRC ID |
84385
|
| Author |
Fuchiyama K, Yabuki Y, Yamamoto Y, Asakawa R, Matsumoto S, Ibayashi Y, Furuyama Y, Ohgane K, Kamisuki S, Watashi K, Matsubayashi M, Kuramochi K.
|
| Title |
Synthesis and Biological Assessment of Eucalyptin: Magic Methyl Effects.
|
| Journal |
Int J Mol Sci
|
| Abstract |
A drastic alteration in the potency or efficacy of bioactive compounds due to the addition of a single methyl group is known as the magic methyl effect. This effect has been demonstrated in O-methylated flavonoids, which show differences in physical and chemical properties from those of unmethylated flavonoids-O-methylation converts the hydrophilic hydroxy group into a hydrophobic methoxy group. However, differences in the physical and chemical properties between C-methylated and unmethylated flavonoids are smaller than those for O-methylated flavonoids. Therefore, predicting the magic methyl effect in C-methylated flavonoids is challenging. Eucalyptin and 8-desmethyleucalyptin are C-methylated flavonoids isolated from the leaves of plants, such as Eucalyptus sp. and Kalmia latifolia. These compounds contain 5-hydroxy-7,4'-dimethoxyflavone as the core skeleton. Eucalyptin has two C-methyl groups at the C-6 and C-8 positions, whereas 8-desmethyleucalyptin has one C-methyl group at the C-6 position. In this study, we synthesized eucalyptin and assessed its biological activities. The C-8 methyl group caused significant alterations in cytotoxic and antibiofilm activities. Herein, we report the magic methyl effects in eucalyptin, providing a basis for further chemical and biological studies on C-methylated flavonoids.
|
| Volume |
26(7)
|
| Published |
2025-4-4
|
| DOI |
10.3390/ijms26073391
|
| PII |
ijms26073391
|
| PMID |
40244279
|
| PMC |
PMC11989289
|
| MeSH |
Anti-Bacterial Agents* / chemical synthesis
Anti-Bacterial Agents* / chemistry
Anti-Bacterial Agents* / pharmacology
Cell Line, Tumor
Eucalyptus / chemistry
Flavonoids* / chemical synthesis
Flavonoids* / chemistry
Flavonoids* / pharmacology
Humans
Methylation
Plant Leaves / chemistry
|
| IF |
4.556
|
| Resource |
| Human and Animal Cells |
HeLa |
| General Microbes |
JCM6425 |
