Chemical profile and biological activities ofDeguelia duckeanaA.M.G. Azevedo (Fabaceae)

Abstract

Deguelia duckeana is popularly known as timbó and used by indigenous people as ictiotoxic. On account of there being no literature pertaining to the chemical profile or biological activity of this plant, the hexane, methanol and aqueous crude extracts from leaves, stems and roots were assayed that presented very high cytotoxic potential against Artemia salina, achieving 100% mortality in up to 5.0 µg mL(-1) concentration, but lower antioxidant potential on 2,2-diphenyl-1-picryl-hydrazyl and Fe(3+)/Phenanthroline assays. The phytochemical analysis of crude extracts showed the presence of flavonoids and related compounds as major constituents as well as steroids in all of them, and tannins in polar extracts. All the extracts were assayed for antibacterial activity but only the hexane extract of stems showed moderate activity on Staphylococcus aureus, which was fractionated and yielded a mixture of 3,5,4'-trimethoxy-4-prenylstilbene, lonchocarpine, 4-hydroxylonchocarpine and derricidine, reported for the first time in D. duckeana and other fraction with β-sitosterol and stigmasterol mixture.

Lonchocarpine Increases Nrf2/ARE-Mediated Antioxidant Enzyme Expression by Modulating AMPK and MAPK Signaling in Brain Astrocytes

“…Compound 1 (1.2 g) was isolated from these subfractions. This compound was identified as lonchocarpine by instrumental analysis and compared to an authentic standard described in the literature (Lima et al ., 2013). The purity of lonchocarpine was more than 95%.…”

“…It also showed acute anti-inflammatory and anti-oedematogenic properties in a paw oedema model (Fontenele et al ., 2009). In addition, lonchocarpine has anti-bacterial activity on Staphylococcus aureus (Lima et al , 2013). A recent study reported that lonchocarpine inhibited nitric oxide production in lipopolysaccharidestimulated BV2 microglial cells (Li et al ., 2015).…”

Isolation of Flavonoids from Deguelia duckeana and Their Effect on Cellular Viability, AMPK, eEF2, eIF2 and eIF4E

“…Based on 1 H-, 13 C-NMR and EI-MS data as well as comparison to spectral data from the literature these compounds were identified as 3,5,4'-trimethoxy-4-prenylstilbene (1) [11], 4-methoxyderricidine (2) [11], 4-hydroxylonchocarpine (4) [11], 4-methoxylonchocarpine (5) [11], 4'-hydroxyisolonchocarpine (7) [12], 4'-methoxyisolonchocarpine (8) [13], 3',4'-methylenedioxy-7-methoxyflavone (10) [14] and 2,2-dimethylchromone-5,4'-dihydroxy-5'-methoxyflavone (11) [15]. The hexane extract from branches yielded two known flavonoids which were identified by the methods mentioned above as lonchocarpine (3) [11] and 3',4',7-trimethoxyflavone (9) [16].…”

“…The hexane extract from branches yielded two known flavonoids which were identified by the methods mentioned above as lonchocarpine (3) [11] and 3',4',7-trimethoxyflavone (9) [16]. Except for 1, 3, and 4 [11] all these compounds are described for the first time in D. duckeana. The structures are given in Figure 1.…”

“…However, the compounds responsible for these cytotoxic effects as well as their mode(s) of action are still unknown. Initial phytochemical investigations revealed three chalcones and a stilbene derivative as constituents, but no studies on their cytotoxic activities have been performed [11]. This prompted us to reinvestigate D. duckeana and to perform the first studies on which way the isolated flavonoids may affect cell life using the neuronal cell line SK-N-SH.…”