Chemical constituents of the underground stem bark of Duguetia furfuracea (Annonaceae)

Abstract

No presente trabalho foi realizado um estudo fitoquímico com os diferentes extratos obtidos a partir de órgãos subterrâneos de Duguetia furfuracea (Annonaceae), o qual incluiu o teste de toxicidade para Artemia salina. O extrato alcaloídico, obtido das cascas do caule subterrâneo, conduziu ao isolamento de (-)-duguetina β-N-óxido, de (-)-duguetina, dicentrinona, (-)-Nmetiltetraidropalmatina e (+)-N-metilglaucina. Do extrato etanólico do cerne do caule subterrâneo obteve-se alantoína por precipitação. O óleo volátil e o extrato apolar também foram extraídos das cascas do caule subterrâneo. As substâncias 2,4,5-trimetoxiestireno, α-gurjuneno, aromadendreno, biciclogermacreno, (E)-metil-isoeugenol e α-asarona foram isoladas a partir do óleo volátil, e as substâncias policarpol, óxido de β-cariofileno, 2,4,5-trimetóxi-estireno, α-asarona e asaraldeído foram obtidas do extrato em éter de petróleo. Este estudo descreve pela primeira vez o alcalóide β-N-óxido de (-)-duguetina, e a ocorrência das substâncias (-)-Nmetiltetraidropalmatina e (+)-N-metilglaucina na família Annonaceae. Todos os extratos se mostraram tóxicos nos testes com Artemia salina.In the present investigation the underground parts of Duguetia furfuracea (Annonaceae) were used to conduct a phytochemical study that included the brine shrimp (Artemia salina) lethality bioassay. The substances (-)-duguetine β-N-oxide, (-)-duguetine, dicentrinone, (-)-Nmethyltetrahydropalmatine, and (+)-N-methylglaucine were isolated from the alkaloid extract of the bark of the underground stem, and the ureide allantoin was also isolated by precipitation from the ethanol extract of the wood of the underground stem. A fresh volatile oil and a nonpolar extract were also obtained from the underground stem bark. The substances 2,4,5-trimethoxystyrene, α-gurjunene, aromadendrene, bicyclogermacrene, (E)-methylisoeugenol, and α-asarone were isolated from the fresh volatile oil and polycarpol, β-caryophyllene oxide, 2,4,5-trimethoxystyrene, α-asarone, and asaraldehyde were obtained from the petroleum ether extract. The present study describes for the first time the alkaloid (-)-duguetine β-N-oxide and the occurrence of (-)-N-methyltetrahydropalmatine and (+)-N-methylglaucine in the family Annonaceae. All extracts were active in the brine shrimp lethality bioassay.Keywords: alkaloids, Annonaceae, aporphines, duguetine β-N-oxide, Duguetia furfuracea, sesquiterpenoids IntroductionNearly 80 species are known in the genus Duguetia, which is one of the 128 genera included in the family Annonaceae. 1 This paper reports the results of our continued phytochemical investigations of the family Annonaceae. We analyzed various extracts obtained from the underground stem bark of Duguetia furfuracea (A. St.-Hil.) Benth. & Hook f., which is a shrub distributed throughout the Brazilian state of Mato Grosso do Sul. Two species of the genus Duguetia have been found and worked up to date, and little data on their use in folk medicine can be found in the literature.D. furfuracea is known as "araticum-s...

Modulatory effects of Duguetia furfuracea (A. St. Hil) Benth. and Hook. f. in Drosophila melanogaster somatic and germinative cells

“…Studies on the chemical composition of D. furfuracea essential oil showed a high percentage of alkaloids, including monoterpenes and sesquiterpenes (Silva et al, 2007;Valter et al, 2008). Flavonoid glycosides are also found in this plant (Carollo et al, 2006).…”

“…Among these activities, the most representative in the Duguetia genus is cytotoxicity, which has been demonstrated in experiments using different strains of tumor cells. This is the case for the commonly isolated substance liriodenine (Silva et al, 2007). Liriodenine is a potent topoisomerase II inhibitor (Woo et al, 1999).…”

“…Silva et al (2007) carried out biomonitored phytochemical studies of the extract obtained from the underground parts of D. furfuracea in a toxicity bioassay using brine shrimp (Artemia salina) and all extracts were active in the brine shrimp lethality bioassay. Garcia et al (2000) conducted a triage of extracts obtained from plants that belong to the families Combretaceae, Apocynaceae and Annonaceae in order to assess their possible anti-tumor activity and biomonitored isolates of active compounds against A. salina.…”

Polycarpol in Unonopsis, Bocageopsis and Onychopetalum Amazonian species: chemosystematical implications and antimicrobial evaluation

“…This idea was supported over the years (Goulart et al, 1986;Jung et al, 1990). Polycarpol was recently isolated from Duguetia glabriuscula (Pereira et al, 2003), Duguetia furfuraceae (Silva et al, 2007), Artabotrys madagascariensis (Murphy et al, 2008), Piptostigma preussi (Ngantchou et al, 2009) and Artabotrys spinosus (Sichaem et al, 2011), all species from Annonaceae family, which has enhances the initial proposition of this compound as a chemotaxonomic marker for this family. Considering its broad occurrence at genera level, is appropriate to restrict the term "chemotaxonomic marker" at family level, being suggested the use of the term "chemical marker" to genera level.…”

Acaricidal activity of Annonaceae fractions against Tetranychus tumidus and Tetranychus urticae (Acari: Tetranychidae) and the metabolite profile of Duguetia lanceolata (Annonaceae) using GC-MS

“…2,4,5-trimethoxystyrene trans-asarone m/z Trans-asarone and 2,4,5-trimethoxystyrene are relatively common metabolites in the Annonaceae family (WANG et al, 1988;NGADJUI et al, 1989;SILVA et al, 2007;YAPI et al, 2012). It is noteworthy that trans-asarone was recently identified as a component of an essential oil extracted from D. lanceolata branches (SOUSA et al, 2012).…”