A survey of restriction site variation in the chloroplast genome of th
e annual plant genus Amsinckia, together with estimation of outcrossin
g rates, was conducted to analyze the evolutionary history of rbe mati
ng system. Species, and in some cases populations within species, diff
er markedly in their mating system. Five taxa are distylous and predom
inantly outcrossing, or show mixed mating systems, while the remaining
taxa are homostylous and predominantly self-fertilizing Reconstructio
n of the molecular phylogeny of the group places different distylous a
nd homostylous tars at four separate branch tips. When distyly is trea
ted as ancestral in the group, or when the loss of distyly is assumed
to be more common than its gain, the results of the phylogenetic analy
sis support the hypothesis that the self-fertilizing taxa are of recen
t origin from outcrossing relatives. These findings are discussed with
respect to theory fur the evolution and breakdown of distyly and the
probability of extinction of selling lineages.