494-15-5Relevant articles and documents
Ammodendrine and N-methylammodendrine enantiomers: Isolation, optical rotation, and toxicity
Lee, Stephen T.,Molyneux, Russell J.,Panter, Kip E.,Chang, Cheng-Wei Tom,Gardner, Dale R.,Pfister, James A.,Garrossian, Massoud
, p. 681 - 685 (2007/10/03)
Ammodendrine (1) was found to occur as a mixture of enantiomers in two different collections of plants identified as Lupinus formosus. The ammodendrine fraction was reacted in a peptide coupling reaction with 9- fluorenylmethoxycarbonyl-L-alanine (Fmoc-L-Ala-OH) to give diastereomers, which were separated by preparative HPLC. The pure D- and L-ammodendrine enantiomers were then obtained by Edman degradation. Optical rotation measurements revealed that the D- and L-enantiomers had optical rotations of [a]24 D +5.4° and -5.7°, respectively. D- and L-N- methylammodendrine enantiomers were synthesized from the corresponding ammodendrine enantiomers, and their optical rotations established as [a] 23D +62.4° and -59.0°, respectively. A mouse bioassay was used to determine the difference in toxicity between these two pairs of naturally occurring enantiomers. The LD50 of (+)-D-ammodendrine in mice was determined to be 94.1 ± 7 mg/kg and that of (-)-L-ammodendrine as 115.0 ± 7 mg/kg. The LD50 of (+)-D-N-methylammodendrine in mice was estimated to be 56.3 mg/kg, while that of (-)-L-N-methylammodendrine was determined to be 63.4 ± 5 mg/kg. These results establish the rotation values for pure ammodendrine and N-methylammodendrine and indicate that there is little difference in acute murine toxicity between the respective enantiomers.
