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The early-branching clades of Fabaceae subfamily Papilionoideae are characterized by their remarkable lability in floral architecture. In contrast, more derived papilionoid lineages are marked by evolutionary conservatism towards strongly bilateral, papilionate flowers. Here, we show an unexpected example of conservatism of a unique floral architecture during the early diversification history of the papilionoids. We built the most comprehensively sampled molecular phylogenetic tree with a focus on the early-diverging papilionoid Dipterygeae clade to evaluate conservatism of the winged papilionate architecture and associated traits related to flower specialization (e.g. zygomorphy, petal differentiation, stable stamen number and stamen sheath). Dipterygeae comprise c. 22 species of mostly giant trees from across tropical forests in Central America and the Amazon, but they are also ecologically dominant in the savannas of the Brazilian Central Plateau. Phylogenetic analyses of nuclear ribosomal ITS/5.8S and plastid matK and trnL intron sequences strongly supported inter-relationships and the monophyly of each genus (Dipteryx , Monopteryx , Pterodon and Taralea). Bayesian relaxed-clock dating and a Bayesian model of ancestral character estimation revealed c. 30 Myr of conservatism of all winged papilionate-related flower traits in a clade comprising the most recent common ancestor of Dipteryx , Pterodon and Taralea , but lability in fruit morphology during the diversification of the entire Dipterygeae clade. Despite Monopteryx and remaining Dipterygeae being florally discrepant, they are collectively defined by a floral synapomorphy that is unique among all papilionoid Fabaceae: the highly differentiated calyx, where the two upper lobes are enlarged and wing-like, whereas the other three lower lobes are reduced. We suggest that the different dispersal strategies and the ancient winged papilionate floral conservatism in Dipterygeae, which has maintained effective ecological interactions with specialized pollinators and ensured the protection of young flower buds and developing fruits, may explain successful evolutionary and ecological persistence of the clade across the main Neotropical biomes. [ABSTRACT FROM AUTHOR]