Chemotaxonomic significance of flavonoids, coumarins and triterpenes of Augusta longifolia (Spreng.) Rehder, Rubiaceae-Ixoroideae, with new insights about its systematic position within the family

Abstract

RESUMO: "Significância quimiotaxômica de flavonoides, cumarinas e triterpenos de Augusta longifolia (Spreng.) Rehder, Rubiaceae-Ixoroideae, com novos entendimentos sobre a posição sistemática dentro da família". Augusta tem sido tradicionalmente colocada na tribo Rondeletieae, Cinchonoideae subfamília. No entanto, recentes filogenias moleculares posicionou-a perto de Wendlandia, porém localizando A. longifolia perto do clado Ixoroidinae II. O estudo de A. longifolia resultou em duas cumarinas, cinco flavonoides, três triterpenoides e um derivado do ácido benzóico. Estes metabolitos reforçam a separação da Augusta como um gênero monoespecífico, e Lindenia como um gênero de três espécies, intimamente relacionada com Wendlandia.Unitermos: Rubiaceae, Augusta, Wendlandia, Lindenia, quimiotaxonomia.ABSTRACT: Augusta has traditionally been placed in the tribe Rondeletieae, subfamily Cinchonoideae. However, recent molecular phylogenies positioned it near to Wendlandia (Ixoroideae), but locate A. longifolia near to the clade Ixoroidinae II. The study of A. longifolia afforded two coumarins, five flavonoids, three triterpenoids and one benzoic acid derivative. These metabolites reinforce the separation of Augusta as a monospecific genus, and Lindenia as a genus of three species, closely related to Wendlandia.

Molecular phylogenetic study of flavonoids in medicinal plants: a case study family Apiaceae

“…This coincidence between molecular phylogeny and other analyses such as flavonoids content (with its sub-groups, flavonol and flavone), other factors related to flavonoids production (ABA-sucrose–PAL activity) and gene expression suggests that phylogeny can predict flavonoids content. The agreement of the present molecular data with secondary metabolites (flavonoids) has been approved in several studies, including Choze et al ( 2010 ), Fico et al ( 2003 ), and Wollenweber et al ( 2003 ), which showed that at different hierarchical levels, the occurrence and distribution patterns of flavonoids mostly confirm newer molecular findings. Moreover, Kharazian, ( 2014 ) revealed that the chemical diversity of flavonoid profiles in 14 Salvia species (flavones, flavonols, flavanones, isoflavones, dihydroflavonols, and chalcones) can be used to assess the taxonomic status of the Salvia genus and that flavonoids are suitable indicators.…”

Isolation and Identification of the Five Novel Flavonoids from Genipa americana Leaves

“…Geniposidic acid (MM = 374, C 16 H 22 O 10 , Table 1 ), showed signals at 397 [M + Na] + , 373 [M − H] − , 409 [M + Cl] − , 379 [M + Na − H 2 O] + , 217 [M + Na − H 2 O − Glc] + , 210 [M − H − Glc] − , 172 [M + Na − H 2 O − Glc − CO 2 ] + , 166 [M − H − Glc − CO 2 ] − , 148 [M − H − Glc − CO 2 − H 2 O] − , 122 [M − H − Glc − C 3 H 4 O 3 ] − . It is a iridoid already identified in fruit of Gardenia jasminoides Ellis (Rubiaceae) [ 19 , 22 , 31 , 32 ] and Wendlandia formosana Cowan leaves [ 33 ].…”

“…Tarenoside (MM = 358, C 16 H 25 O 9 , Table 1 ): showed signals at 357 [M − H] − ; 393 [M + Cl] − , 194 [M − H − Glc] − . This compound is an iridoid already identified in Wendlandia formosana Cowan leaves and Genipa americana [ 2 , 33 ].…”

CHEMICAL CONSTITUENTS AND EVALUATION OF ANTIOXIDANT AND ANTI-INFLAMMATORY ACTIVITIES OF ROOTS OFSabicea brasiliensisWernh (Rubiaceae).

“…Todos esses compostos estão sendo relatados pela primeira vez no gênero Sabicea e na tribo Sabiceae, porém, na subfamília Ixoroideae há relatos do isolamento da escopoletina de Augusta longifolia, 20 do ácido 5-O-cafeoilquínico e ácidos 3,5-e 4,5-O-dicafeoilquínico de Coffea arabica, 21 além do triterpeno ácido ursólico de Duroia macrophylla.…”