Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.
Bioactivity-guided fractionation of a CH2Cl2 extract from the leaves of Piper aduncum afforded three new dihydrochalcones, piperaduncins A [3], B [4], and C [5], as well as two known dihydrochalcones, 2',6'-dihydroxy-4'-methoxydihydrochalcone [1] and 2',6',4-trihydroxy-4'-methoxydihydrochalcone [2] (asebogenin), together with sakuranetin, anodendroic acid methyl ester, and the carotenoid lutein. The structures of the isolates were elucidated by spectroscopic methods, mainly 1D- and 2D nmr spectroscopy. The proposed stereochemistry for compound 4 was deduced by NOESY spectroscopy and the corresponding energy minimum was established by molecular modelling calculations and translated into a 3D structure.
Orjala
J
J
Department of Pharmacy, Swiss Federal Institute of Technology (ETH) Zurich, Switzerland.
Wright
A D
AD
Behrends
H
H
Folkers
G
G
Sticher
O
O
Rüegger
H
H
Rali
T
T
D000818:Animals; D000900:Anti-Bacterial Agents / Q000302:isolation & purification* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D001700:Biomphalaria; D002599:Chalcone / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D047188:Chalcones; D002855:Chromatography, Thin Layer; D003198:Computer Simulation; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects; D006801:Humans; D007624:KB Cells / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D016982:Micrococcus luteus / Q000187:drug effects; D008958:Models, Molecular; D008968:Molecular Conformation; D008975:Molluscacides / Q000302:isolation & purification / Q000633:toxicity; D009512:New Guinea; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*
D000900:Anti-Bacterial Agents; D000972:Antineoplastic Agents, Phytogenic; D047188:Chalcones; D008975:Molluscacides; D010936:Plant Extracts; D002599:Chalcone; C015812:dihydrochalcone