2,4,5-Trimethoxystyrene, a Bioactive Component of the Bark of Duguetia panamensis

Wang, Z.-W.; Ma, Wenwen; McLaughlin, Jerry L.; Gupta, Michèle

doi:10.1021/np50056a041

Cited by 14 publications

(12 citation statements)

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“…The toxicity exhibited by the extracts and fresh volatile oil might be explained by the presence of active substances previously tested in the brine shrimp lethality bioassay, namely 2,4,5-trimethoxystyrene (7) (LD 50 = 8 μg mL -1 ), 18 found in both the fresh volatile oil and petroleum ether extract, polycarpol (13) (LD 50 = 254 μg mL -1 ), 19 in the petroleum ether extract, and several oxoaporphine alkaloids. 20 …”

Section: Resultsmentioning

confidence: 98%

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

Silva¹,

Tulli²,

Garcez³

et al. 2007

J. Braz. Chem. Soc.

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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...

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Section: Resultsmentioning

confidence: 98%

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

Silva¹,

Tulli²,

Garcez³

et al. 2007

J. Braz. Chem. Soc.

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“…However, the HDL cholesterol concentration level was exceeded considerably for the former. Compound 10a has been, on the other hand, isolated from Piperaceae and Annonaceae families [26,28], and it shows cytotoxic activity [29].…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Hypolipidemic Activity of Modified Side Chain α-Asarone Homologues

Cruz¹,

Garduno²,

Salazar³

et al. 2011

Arzneimittelforschung

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A series of homologues of alpha-asarone (1), containing variable size and functionality on the side chain attached to the aromatic ring, has been subjected to a study of structure-activity relationship. For most of the prepared derivatives, either with a carbonyl (8a-8e), a hydroxy group (9a-9e), or with a conjugated double bond (10a-10d), significant effects on serum lipoprotein cholesterol, LDL-cholesterol, HDL-cholesterol and triglycerides were displayed. The results showed an enhancement of the hypocholesterolemic activity as the length of the chain is decreased. Theoretical conformational and electrostatic potential analyses of I and olefins 10 suggest unfavorable steric interactions in the bulky superior side-chain homologues as the deactivating biological effect.

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“…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).…”

Section: Analysis By Gc-msmentioning

confidence: 99%

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

et al. 2015

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Species of the Tetranychus genus feed on plant tissues, which reduces the rate of photosynthesis and can lead to the death of plant tissues. As a result, considerable production losses are caused by these arthropods. Thus, in order to aid in the development of new products for the control of Tetranychus tumidus Banks and Tetranychus urticae Koch (Acari: Tetranychidae), the initial objective of this study was to select Annonaceae derived fractions that were soluble in dichloromethane and have acaricidal activity. Then, an exploratory analysis of the metabolite profile of the most successful fraction was performed by gas chromatography-mass spectrometry (GC-MS). Among the dichloromethane soluble fractions derived from Annona cacans Warm., Annona coriacea Mart., Annona neolaurifolia H. Rainer, Annona sylvatica A.St.-Hil., Duguetia lanceolata A.St.-Hil., Guatteria australis A.St.-Hil., Xylopia brasiliensis Spreng., Xylopia emarginata Mart. and Xylopia sericea A.St.-Hil., only the fraction from D. lanceolata stem bark reduced the survival of T. tumidus females. However, ovicidal activity was not detected when D. lanceolata stem bark was evaluated against T. tumidus eggs. Further, we studied the effect of dichloromethane soluble fractions from D. lanceolata leaves, berry fruits and stem bark on T. urticae, and the stem bark was found to be the most active fraction against T. urticae. The metabolite profile analysis of D. lanceolata stem bark by GC-MS, suggested that the main constituents were 2,4,5-trimethoxystyrene and trans-asarone. Key words: Botanic acaricide, secondary metabolites, 1,2,4-trimethoxy-5-vinylbenzene, 1,2,4-trimethoxy-5-[(1E)-1-propen-1-yl]benzene ResumoAs espécies do gênero Tetranychus alimentam-se de tecidos vegetais acarretando redução na capacidade fotossintética da planta, que pode resultar em morte dos tecidos vegetais, como consequência são

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2,4,5-Trimethoxystyrene, a Bioactive Component of the Bark of Duguetia panamensis

Cited by 14 publications

References 0 publications

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

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

Synthesis and Hypolipidemic Activity of Modified Side Chain α-Asarone Homologues

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

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