The aporphine alkaloids of Litsea glutenosa

Tewari, Shobha; Bhakuni, D. S.; Dhar, Mridul

doi:10.1016/s0031-9422(00)88469-1

Cited by 35 publications

(23 citation statements)

References 10 publications

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“…46 Therefore, this study reports the complete and unequivocal 1 H and 13 C NMR chemical shift assignments for cassythicine 3, as well as their heteronuclear 1 H-13 C correlations, nOe observations, and accurate 1 H-1 H scalar coupling constants (Table 1). The NMR data for 3 were initially collected in CDCl 3 as the solvent.…”

Section: Chemical Studiesmentioning

confidence: 95%

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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Section: Chemical Studiesmentioning

confidence: 95%

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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“…Metabolites MI-4, -8, and -9 were characterized as the known lastourvilline (O,O-demethylenyldicentrine) (Eloumi-Ropivia et al, 1985), actinodaphnine (N,O 9 -didemethyldicentrine) (Lee and Yang, 1992), and cassythicine (N-methylactinodaphnine, O 9 -demethyldicentrine) (Tewari et al, 1972;Hara et al, 1986), respectively, based on the online 1 H NMR (Supplemental Fig. S1 and Table S1) and the ϩ HRESIMS analyses.…”

Section: Dicentrine Metabolites In Miniature Pig Urinementioning

confidence: 99%

Metabolism of Dicentrine: Identification of the Phase I and Phase II Metabolites in Miniature Pig Urine

Lai¹,

Kuo²,

Chen³

et al. 2010

Drug Metab Dispos

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ABSTRACT:The metabolic profile of dicentrine, a selective ␣ 1 -adrenoceptor antagonist with potent antiarrhythmic and antihypertensive activities, in miniature pig urine via oral administration was investigated for the first time. The urine, collected after a single oral administration of dicentrine, was pretreated using solvent extraction and column chromatographic methods to identify the metabolites containing fractions. Twenty-four metabolites (MI-1-9 and MII-1-15), of which 21 compounds are new, were identified by mass spectrometry and high-performance liquid chromatography-diode array detector solid-phase extraction-NMR techniques. Of these, 14 metabolites (MI-5, MII-1 and 2, and MII-5-15) were further isolated for structure confirmation. The phase I metabolic transformations of dicentrine were found to be N-demethylation, N-oxidation, O-demethylation (9,10-OMe), O,O-demethylenation (1-OCH 2 O-2), and hydroxylation at the benzylic (C-4) and the aromatic (C-3) positions, whereas those for the phase II were O-glucuronidation and O-glucosylation of the phenolic group of the phase I metabolites.

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“…From the root of L. chunii we isolated 20 compounds, including three new compounds called lindenanolides E (1), F (2) and G (3), new naturally occurring lindenanolide H (4), 5) two new aporphine alkaloids called lindechunines A (18) and B (20), six known sesquiterpenes: pseudoneolinderane (5), 6) lindeneol (6), 7) lindeneyl acetate (7), 7) lindera lactone (8), 7) strychinstenolide 6-O-acetates A (9) and B (10), 8) and eight known aporphine alkaloids: hernandine (11), 9) hernangerine (12), 9) ocokryptine (N-methylhernandine) (13), 10) hernandonine (14), 11) N-methylhernangerine (15), 12) laurolistine (norboldine) (16), 13) 7-oxohernangerine (17) 14) and 7-oxohernagine (19) 14) (Chart 1). The structures of known compounds were determined by comparing their spectral data with those of authentic samples or previously reported data.…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H-1 H correlation spectroscopy (COSY) experiment showed the presence of a cyclopropane ring (H-1, H 2 -2, H-3). The presence of three carbonyl carbons, including an aldehyde group, was suggested on the basis of the 13 C-NMR signals at d 164.5, 167.9 and 186.0, and the IR absorption bands at n max 1768 and 1653 cm…”

Section: Resultsmentioning

confidence: 99%

“…The structure of 2 was unambiguously assigned by detailed analysis of the two-dimensional (2D)-NMR [ 1 H-1 H COSY, HMQC and HMBC (see Fig. 2)] spectra and by comparison of the 13 C-NMR spectral data with those of strychnistenolides A (9) and B (10), 8) as well as lindenanolide H (4) ( Table 1). Compound 2 was consequently deduced to be a bis-sesquiterpene linked together at C-8.…”

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Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase.

et al. 2002

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The aporphine alkaloids of Litsea glutenosa

Cited by 35 publications

References 10 publications

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

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

Metabolism of Dicentrine: Identification of the Phase I and Phase II Metabolites in Miniature Pig Urine

Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase.

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