Aporphinoid Alkaloids, V

Guinaudeau, Hélène; Lebœuf, Michel; Cavé, André

doi:10.1021/np50110a001

Cited by 154 publications

(137 citation statements)

References 139 publications

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“…Benzylisoquinolines and aporphines are the most widespread alkaloids in the Lauraceae, 15 and are commonly found in Cryptocarya species. 20,21,22,23,24 . Alkaloids present in very small amounts insufficient for NMR analysis were identified based on their MS fragmentation patterns compared with those reported in the literature or obtained with authentic samples (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Phytochemical Analysis of Alkaloids From the Chilean Endemic Tree Cryptocarya Alba

Castro-Saavedra

Fuentes-Barros

Tirapegui

et al. 2016

J. Chil. Chem. Soc.

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A phytochemical study of the roots and aerial parts of Cryptocarya alba (Mol.) Looser (Lauraceae), an endemic Chilean tree and the southernmost Cryptocarya species, led for the first time to the isolation and unambiguous characterization of four known alkaloids by NMR techniques: boldine, laurolitsine, laurotetanine and norglaucine, in addition to the previously identified reticuline, and the identification via UHPLC-MS of seven more alkaloids, coclaurine, N-methylcoclaurine, norreticuline, isocorydine, N-methyllaurotetanine, predicentrine and glaucine. In spite of this fairly broad variety of benzyltetrahydroisoquinolines and aporphines, the concentrations of these alkaloids in the different organs of C. alba are quite low, which is in contrast with the sometimes generous yields of alkaloids in this genus.

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Section: Resultsmentioning

confidence: 99%

Phytochemical Analysis of Alkaloids From the Chilean Endemic Tree Cryptocarya Alba

Castro-Saavedra

Fuentes-Barros

Tirapegui

et al. 2016

J. Chil. Chem. Soc.

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“…8 By comparing the 13 C NMR data of 1 with those of 2, using N-O models available in the literature, namely oliveroline β-N-oxide (6a,7α-H, β-Noxide) 9 and dasymaschaline α-N-oxide (6a,7α-H, α-Noxide), 8 and confirming with NOESY the stereochemistry of the N-oxide moiety of 1, it was possible to propose that 1 is a (-)-duguetine β-N-oxide (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…10 The fresh volatile oil was fractionated by CC on silica gel, yielding several fractions. The fractions, composed of a mixture of two compounds, were subjected to an additional preparative thin layer chromatography (TLC) followed by preparative argentation TLC separation, and six compounds (7)(8)(9)(10)(11)(12) were isolated and identified by comparison of their spectral data with literature values (see Experimental section). In order to contribute to the chemical knowledge of nonpolar compounds from the fresh stem bark, the fresh volatile oil was subjected to GC/MS analysis.…”

Section: Resultsmentioning

confidence: 99%

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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“…On the other hand, cassythicine (3) is more commonly found in species of Lauraceae, a family phylogenetically close to the Annonaceae, particularly in the genera Cassytha, Laurus, Litsea, Stephania, and Neolitsea; however, it is also found in some species of the genus Annona, such as A. glabra. [37][38][39][40]43 Additionally, the neutral fraction of the CH 2 Cl 2 extract yielded acanthoic acid (1), 17 three methyl esters of fatty acids 4, 5, and 6, 4,36 one sesquiterpene 7, 44 a mixture of the steroids 8 and 9, 45 and one monounsaturated fatty acid 10, 36 described for the first time in this species. They were characterized on the basis of chromatographic and spectroscopic methods, such as GC-MS, IR, ESI-MS, and NMR (1D and 2D), and comparison with data from the literature.…”

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Acanthoic acid and other constituents from the stem of Annona amazonica (Annonaceae)

Pinheiro

Xavier

Souza

et al. 2009

J. Braz. Chem. Soc.

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O presente trabalho descreve o isolamento, a partir do caule de Annona amazonica, do ácido acantóico, um diterpeno do tipo pimaradieno que possui várias e importantes atividades biológicas descritas na literatura. Neste estudo foi verificado que este composto apresenta significante atividade tripanocida contra as formas epimastigotas de Trypanosoma cruzi. Também foi constatado que este diterpeno é o constituinte majoritário da planta, encontrado em cerca de 65% do extrato hexânico, demonstrando que A. amazonica é uma nova fonte natural renovável desta substância. Além do ácido acantóico, a investigação química resultou no isolamento dos alcalóides liriodenina e cassiticina, entre outros compostos, tais como terpenos, esteróides e ácidos graxos. Adicionalmente, é descrita a completa e inequívoca atribuição dos deslocamentos químicos de RMN de 1 H e 13 C da cassiticina.The present work reports the isolation of acanthoic acid, a promising pimaradiene-type diterpene with several important biological activities described in the literature, from the stems of Annona amazonica. We found that acanthoic acid has significant trypanocidal activity against the epimastigote forms of Trypanosoma cruzi. This diterpene is the major constituent of the plant, comprising at least 65% of the hexane extract, demonstrating that A. amazonica is a new renewable natural source for this compound. The chemical investigation also resulted in the isolation of the alkaloids liriodenine and cassythicine, and other compounds including terpenes, sterols, and fatty acids. Additionally, the complete and unequivocal 1 H and 13 C NMR chemical shift assignments for cassythicine are provided. Keywords: Annona amazonica, Annonaceae, acanthoic acid, cassythicine, trypanocidal activity IntroductionThe family Annonaceae, comprised of tropical and subtropical species with about 135 genera and more than 2500 species and widely distributed in South and Central America, Africa, Asia, and Australia, 1 is known for its edible fruits and the medicinal properties of several species. 2 In Brazil, there are 26 genera with about 260 species, including the genus Annona, which contains approximately 120 species. 3 Chemical investigations of species of Annonaceae have revealed their high chemical diversity in terms of secondary metabolites, such as alkaloids, acetogenins, terpenoids and lactones. These compounds have shown important biological activities, including antiparasitic, in particular against Leishmania sp., Plasmodium falciparum, and Trypanosoma cruzi. [4][5][6][7][8][9][10][11][12] Annona amazonica R.E. Fries is a tropical tree that grows up to 20-25 m tall and 35-60 cm in diameter, and is found from Panama to South America. In Brazil this species commonly occurs in the Amazon, mainly in the states of Amazonas and Pará. 13 To the best of our knowledge, only one previous phytochemical study has described the isolation and identification of cyanogenic constituents from this species. 14 Here we describe the isolation and structural identification of the chemica...

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Aporphinoid Alkaloids, V

Cited by 154 publications

References 139 publications

Phytochemical Analysis of Alkaloids From the Chilean Endemic Tree Cryptocarya Alba

Phytochemical Analysis of Alkaloids From the Chilean Endemic Tree Cryptocarya Alba

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

Acanthoic acid and other constituents from the stem of Annona amazonica (Annonaceae)

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