Chemical constituents of Pseudobrickellia brasiliensis leaves(Spreng.) R.M. King & H. Rob. (Asteraceae)

Abstract

Pseudobrickelliabrasiliensisis aspecies endemic toBrazil, popularlyknown as "arnica"/ "arnica-do-campo"/ "arnica-do-mato" and used for itsanalgesicand antiinflammatoryproperties. The objective of this research was thephytochemical studyof the essential oilandhexaneandethyl acetateextracts of the leaves of this species. The essential oilwasextracted byhydrodistillation using a Clevengerapparatusand was analyzed byGC/MS, 25components were identified, with a predominance ofmonoterpenes. The extractswere subjected toclassicalchromatographyand the fractionswere analyzed byGC/ MS, 1D 1 H-NMR, 13 C-NMR and 13 C-NMR-DEPT 135.α-amyrin, α-amyrin acetate, β-amyrin, β-amyrin acetate, lupeol, lupeolacetate, pseudotaraxasterol andtaraxasterol (triterpenes), andkaurenoicacid (diterpene) were identified.Theseterpenesarechemo-taxonomicallyrelated to theEupatorieaetribe(Asteraceae) and may be responsible for the anti-inflammatory activity attributed to the plant.Key words: Pseudobrickellia brasiliensis, Asteraceae, medicinal plant, phytochemistry, terpenes. RESUMO: Constituintes químicos das folhas de Pseudobrickellia brasiliensis (Spreng.) R.M. King & H. Rob. (Asteraceae).Pseudobrickellia brasiliensis é uma espécie endêmica do Brasil, popularmente conhecida como "arnica"/ "arnica-do-campo"/ "arnica-do-mato" e usada por suas propriedades analgésica e antiinflamatória. O objetivo do trabalho foi o estudo fitoquímico do óleo essencial e dos extratos hexânico e em acetato de etila das folhas dessa espécie. O óleo essencial foi extraído por hidrodestilação em aparato de Clevenger e foi analisado por CG/ EM, sendo identificados 25 componentes, com predomínio de monoterpenos. Os extratos foram submetidos a cromatografia clássica, e as frações foram analisadas por CG/EM, 1D 1 H-RMN, 13 C-RMN e 13 C-RMN-DEPT 135. Foram identificados α-amirina, acetato de α-amirina, β-amirina, acetato de β-amirina, lupeol, acetato de lupeol, pseudotaraxasterol e taraxasterol (triterpenos) e o ácido caurenóico (diterpeno). Estes terpenos estão quimiotaxonomicamente relacionados a tribo Eupatorieae (Asteraceae) e podem ser responsáveis pela atividade antiinflamatória atribuída a planta. Palavras-chave:Pseudobrickellia brasiliensis, Asteraceae, planta medicinal, fitoquímica, terpenos.

Scents from Brazilian Cerrado: chemical composition of the essential oil fromPseudobrickellia brasiliensis(Asteraceae)

“…Only one previous investigation on the essential oil of the same species was found, as a Master of Science thesis (5). A very low oil yield, 0.02%, and a quite different chemical composition, with α-pinene (32.6%), α-thujene (17.9%), α-phellandrene (8.9%), β-pinene (7.6%) as major compounds were reported (5).…”

“…A very low oil yield, 0.02%, and a quite different chemical composition, with α-pinene (32.6%), α-thujene (17.9%), α-phellandrene (8.9%), β-pinene (7.6%) as major compounds were reported (5).…”

“…5 were picked in April (fall) at 1348 m in vegetative stage. It is worth note to mention the two oils are rich in different cyclic monoterpenoids, but these compounds share a common precursor, the terpinyl cation (12).…”

“…An essential oil containing 32.6% of α-pinene and 17.2% of α-thujene was reported in a phytochemical investigation on this species (5). Ethanol and ethyl acetate extracts from the leaves showed to be cytotoxic to human peripheral blood mononuclear cells, but not the aqueous extract, which was then observed to reduce the expression of interferon-gamma and tumor necrosis factor, cytokines related to cell inflammatory process (6).…”

Biotechnological applications of the medicinal plant Pseudobrickellia brasiliensis and its isolated endophytic bacteria

“…popularly known as 'arnica-do-campo' or 'arnicado-mato', is a native species of the Brazilian Cerrado (Nakajima and Semir 2016) known for its medicinal properties. It is a shrub or subshrub species, belonging to the Eupatorieae tribe, Asteraceae family (Amorim et al 2016). The alcoholic extract obtained from the leaves of that species is used as a topical anti-inflammatory, wound healing and analgesic agent.…”