A novel nor-megastigmane from the leaves of Rhaphiostylis beninensis.

A novel nor-megastigmane, normegastigmane-5α,9-epoxy-3ß,8-diol (1), together with 10 known compounds of diverse classes including megastigmanes, sesquiterpenoids, and triterpenoids were isolated from the leaves of Rhaphiostylis beninensis. The structure of 1 was established by 1D and 2D NMR and HRESIMS data analysis. The known compounds were identified as 5,11-epoxy-3,9-megastigmanediol (2), 7-megastigmene-3,6,9-triol (3), 1,3-dihydroxypropan-2-yl stearate (4), (1E,5E)-1,5-dimethyl-8-(propan-2-ylidene)cyclodeca-1,5-diene germacrene (5) 3,5-dihyroxy-6,7-megastigmadien-9-one (6), squalene (7), ß-amyrin (8), ß-amyrone (9), ß-amyrin eicosanoate (10), and ß-sitosterol (11). Compounds 2, 3, and 6 displayed inhibitory effects on acetylcholinesterase enzyme. This is the first report of these compounds from the plant and their anticholinesterase activity.

Systematics and phylogeny of Oecopetalum (Metteniusaceae), a genus of trees endemic to North and Central America

El género Oecopetalum Greenm. & C.H. Thomps. (Metteniusaceae) se distribuye en el sureste de México y en América Central (Guatemala, Nicaragua y Costa Rica). Tres especies han sido descritas. Estudiamos especímenes de herbario de Oecopetalum y realizamos un análisis filogenético basado en los genes de los cloroplastos matK y ndhF para responder a las preguntas principales: ¿Cuántas especies hay en el género Oecopetalum? ¿Es Oecopetalum monofilético? ¿Cuáles son las relaciones genéricas con otros miembros de la familia? Oecopetalum es un género monofilético con solo dos especies y Pittosporosis es el grupo hermano. La relación transatlántica de Oecopetalum y Pittosporosis es un patrón geográfico recurrente en la familia Mettenuisaceae, así como en Icacinaceae. Nuestros resultados, en concordancia con la evidencia fósil y las relaciones de otros grupos, apoyan el modelo boreotropical de migraciones terrestres de táxones tropicales desde latitudes altas durante el Paleoceno-Eoceno, globalmente cálido.

Oecopetalum Greenm. & C.H. Thomps. (Metteniusaceae) is distributed in the southeastern portion of Mexico to Central America (Guatemala, Nicaragua, and Costa Rica). Three species have been described. We studied herbarium specimens of the genus Oecopetalum and performed a phylogenetic analysis based on the plastid genes matK and ndhF to answer several major questions: How many species are in the genus Oecopetalum? Is Oecopetalum monophyletic, and how is the genus related to other members of the family? Our results indicate that Oecopetalum is monophyletic, with only two species, and sister to the Asian genus Pittosporopsis. The Trans-Atlantic relationship of Oecopetalum and Pittosporosis is a recurrent geographic pattern in the families Mettenuisaceae and Icacinaceae. Our results, in agreement the fossil record and previous phylogenetic studies, support the boreotropical model of high-latitude terrestrial migrations of tropical taxa during the globally warm Paleocene-Eocene.

Resolving basal lamiid phylogeny and the circumscription of Icacinaceae with a plastome-scale data set.

PREMISE OF THE STUDY: Major relationships within Lamiidae, an asterid clade with ∼40000 species, have largely eluded resolution despite two decades of intensive study. The phylogenetic positions of Icacinaceae and other early-diverging lamiid clades (Garryales, Metteniusaceae, and Oncothecaceae) have been particularly problematic, hindering classification and impeding our understanding of early lamiid (and euasterid) character evolution. METHODS: To resolve basal lamiid phylogeny, we sequenced 50 plastid genomes using the Illumina sequencing platform and combined these with available asterid plastome sequence data for more comprehensive phylogenetic analyses. KEY RESULTS: Our analyses resolved basal lamiid relationships with strong support, including the circumscription and phylogenetic position of the enigmatic Icacinaceae. This greatly improved basal lamiid phylogeny offers insight into character evolution and facilitates an updated classification for this clade, which we present here, including phylogenetic definitions for 10 new or converted clade names. We also offer recommendations for applying this classification to the Angiosperm Phylogeny Group (APG) system, including the recognition of a reduced Icacinaceae, an expanded Metteniusaceae, and two orders new to APG: Icacinales (Icacinaceae + Oncothecaceae) and Metteniusales (Metteniusaceae). CONCLUSIONS: The lamiids possibly radiated from an ancestry of tropical trees with inconspicuous flowers and large, drupaceous fruits, given that these morphological characters are distributed across a grade of lineages (Icacinaceae, Oncothecaceae, Metteniusaceae) subtending the core lamiid clade (Boraginales, Gentianales, Lamiales, Solanales, Vahlia). Furthermore, the presence of similar morphological features among members of Aquifoliales suggests these characters might be ancestral for the Gentianidae (euasterids) as a whole.