Dihydrochalcones from Piper longicaudatum.
Bioactivity-guided fractionation of an ethanolic extract of the leaves and twigs of Piper longicaudatum Trelease & Yunker (Piperaceae) resulted in the isolation of one new (1) and three known (2-4) dihydrochalcones. The known compounds are: 2',6'-dihydroxy-4'-methoxydihydrochalcone (2), 2',6',4-trihydroxy-4'-methoxydihydrochalcone (asebogenin) (3), and 2'-hydroxy-4'-methoxy-2'-[1-hydroxy-1-methylethyl]-2",3"-dihy- drofurano[4",5":5',6"]-3"-[2-hydroxy-5-methoxycarbonylphe- nyl]dihydrochalcone (piperaduncin B) (4). The new compound is 2'-hydroxy-4'-methoxy-2"-[2-hydroxy-5-methoxycarbonyl- phenyl]-furano[4",5":5',6']-dihydrochalcone (longicaudatin) (1). Compounds 1-4 were tested for antibacterial activity against S. aureus and methicillin-resistant S. aureus (MRSA); only compound 3 showed inhibitory activity (IC50 of 10 and 4.5 micrograms/ml, respectively).
Joshi
A S
AS
Li
X C
XC
Nimrod
A C
AC
elSohly
H N
HN
Walker
L A
LA
Clark
A M
AM
D000470:Alkaloids / Q000302:isolation & purification* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000302:isolation & purification* / Q000494:pharmacology; D002599:Chalcone / Q000031:analogs & derivatives* / Q000302:isolation & purification* / Q000494:pharmacology; D047188:Chalcones; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects
C424502:2',6'-dihydroxy-4'-methoxydihydrochalcone; D000470:Alkaloids; D000900:Anti-Bacterial Agents; D047188:Chalcones; C424503:asebogenin; C424504:piperaduncin B; D002599:Chalcone; C041537:longicautadine; C015812:dihydrochalcone