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As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits of  Vitex agnus-castus . These isolates, along with our previously obtained novel compound vitexlactam A ( 1 ), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing an   α  ,   β  -unsaturated   γ  -lactam moiety. Structurally, they were elucidated to be 9  α  -hydroxy-13(14)-labden-16,15-amide ( 2 ) and 6  β  -acetoxy-9  α  -hydroxy-13(14)-labden-15,16-amide ( 3 ), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as vitexilactone ( 4 ), rotundifuran ( 5 ), 8-epi-manoyl oxide ( 6 ), vitetrifolin D ( 7 ), spathulenol ( 8 ),  cis -dihydro-dehydro-diconiferylalcohol-9-O-  β  -D-glucoside ( 9 ), luteolin-7-O-glucoside ( 10 ), 5-hydroxy-3,6,7,4′-tetramethoxyflavone ( 11 ), casticin ( 12 ), artemetin ( 13 ), aucubin ( 14 ), agnuside ( 15 ),   β  -sitosterol ( 16 ),  p -hydroxybenzoic acid ( 17 ), and  p -hydroxybenzoic acid glucose ester ( 18 ). All compound structures were determined/identified on the basis of 1D and/or 2D NMR and mass spectrometry techniques. Compounds  6 ,  8 ,  9 , and  18  were reported from a  Vitex  spieces for the first time. The cancer chemopreventive potentials of these isolates were evaluated for NADP(H):quinone oxidoreductase type 1 (QR1) induction activity. Compound  7  demonstrated promising QR1 induction effect, while the new compound vitexlactam ( 3 ) was only slightly active.

evidence-based complementary and alternative medicine

Compounds from the Fruits of the Popular European Medicinal Plant<i>Vitex agnus-castus</i>in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction

Compounds from the Fruits of the Popular European Medicinal PlantVitex agnus-castusin Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction