Carbon-13 NMR Shift Assignments of Amines and Alkaloids

Shamma, Maurice; Hindenlang, David M.

doi:10.1007/978-1-4684-3432-3

Cited by 87 publications

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“…In the present paper, we describe the isolation and characterization of a novel oleanane-type triterpene, olean-12-ene-11a-methoxy-3β-acetate (10), along with seven known triterpenes, β-amyrin (3), lupeol (4), β-amyrin acetate (5), lupeol acetate (6), olean-12-ene-28-hydroxy-3β-tetradecanoate (7), olean-12-ene-28-carboxy-3β-hexadecanoate (8), ursolic acid (9) and two known monoterpenic indole alkaloids, β-yoimbine (1) and 1,2-dehidroaspidospermidine (2). The structures of known and new compound are being mentioned for the first time in this species and were established on the basis of spectral data, mainly 1 H and 13 C (1D and 2D) NMR spectra, mass spectrometry and by comparison with literature data.…”

Section: Introductionmentioning

confidence: 99%

“…A partir de Aspidosperma illustre, foi obtido como produto natural um novo triterpeno da série oleanano, o olean-12-en-11a-metóxi-3β-acetato (10), além dos triterpenos β-amyrina (3), lupeol (4), acetato de β-amyrina (5), acetato de lupeol (6), olean-12-en-28-hidróxi-3β-tetradecanoato (7), olean-12-en-28-carboxi-3β-hexadecanoato (8), ácido ursólico (9) e dois alcalóides indólicos monoterpênicos, β-ioimbina (1) e 1,2-desidroaspidospermidina (2). As substâncias isoladas foram identificadas através de métodos espectroscópicos, principalmente uni (RMN 1 H, 13 C, APT) e bidimensionais ( A new natural product oleanane-type triterpene, olean-12-ene-11a-methoxy-3β-acetate (10) was isolated from Aspidosperma illustre, together with β-amyrin (3), lupeol (4), β-amyrin acetate (5), lupeol acetate (6), olean-12-ene-28-hydroxy-3β-tetradecanoate (7), olean-12-ene-28-carboxy-3β-hexadecanoate (8), ursolic acid (9) triterpenes, and two monoterpenic indole alkaloids, β-yoimbine (1) and 1,2-dehydroaspidospermidine (2).…”

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“…As substâncias isoladas foram identificadas através de métodos espectroscópicos, principalmente uni (RMN 1 H, 13 C, APT) e bidimensionais ( A new natural product oleanane-type triterpene, olean-12-ene-11a-methoxy-3β-acetate (10) was isolated from Aspidosperma illustre, together with β-amyrin (3), lupeol (4), β-amyrin acetate (5), lupeol acetate (6), olean-12-ene-28-hydroxy-3β-tetradecanoate (7), olean-12-ene-28-carboxy-3β-hexadecanoate (8), ursolic acid (9) triterpenes, and two monoterpenic indole alkaloids, β-yoimbine (1) and 1,2-dehydroaspidospermidine (2). These compounds were characterized on their spectral data basis, mainly one-( …”

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confidence: 99%

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Chemical constituents from Aspidosperma illustre (Apocynaceae)

Barbosa¹,

Mathias²,

Braz-Filho³

et al. 2010

J. Braz. Chem. Soc.

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A partir de Aspidosperma illustre, foi obtido como produto natural um novo triterpeno da série oleanano, o olean-12-en-11a-metóxi-3β-acetato (10), além dos triterpenos β-amyrina (3), lupeol (4), acetato de β-amyrina (5), acetato de lupeol (6), olean-12-en-28-hidróxi-3β-tetradecanoato (7), olean-12-en-28-carboxi-3β-hexadecanoato (8), ácido ursólico (9) e dois alcalóides indólicos monoterpênicos, β-ioimbina (1) e 1,2-desidroaspidospermidina (2). As substâncias isoladas foram identificadas através de métodos espectroscópicos, principalmente uni (RMN 1 H, 13 C, APT) e bidimensionais (

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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Chemical constituents from Aspidosperma illustre (Apocynaceae)

Barbosa¹,

Mathias²,

Braz-Filho³

et al. 2010

J. Braz. Chem. Soc.

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“…Particular attention was paid to the structure determination of the cyclization products. The 13 C-NMR spectra of compounds 4a-c were assigned on the basis of the model spectrum of 2-methyl-4-quinolone [17]. The respective changes to the spectral information of this compound using the chemical shift additivity rules enabled us to evaluate the chemical shifts of the carbons of the formed ring and its influence on carbazolyl fragment moiety, which is adjacent to the newly formed cycle.…”

Section: Resultsmentioning

confidence: 99%

Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo-butanoate and Identification of the Products Obtained

Sapijanskaitė

Mickevicius

Mikulskiene³

2006

Molecules

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Abstract:The reactions in benzene of 9-alkyl-3-aminocarbazoles with ethyl-3-oxobutanoate yielded ethyl-3-[(9-alkyl-9H-carbazol-3-yl)amino]but-2-enoate condensation products or N-(9-ethyl-9H-carbazol-3-yl)-3-oxobutanamide acylation products. The condensation products were cyclized to the corresponding 4,7-dihydro-pyrido[2,3-c]-carbazol-1-ones upon heating in mineral oil at 240-250 °C. The structures of the synthesized compounds were investigated by IR, mass spectrometry, 1 H-and 13 C-NMR spectroscopy and MM2 molecular mechanics and AM1 semi-empirical quantum mechanical methods.

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“…According to an analysis of the results and a comparison with the literature, 2 was identified as tetrahydroberberine [3,5].…”

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Alkaloids from Chelidonium majus growing in Georgia

et al. 2012

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Chelidonium majus L. (Papaveraceae) is broadly distributed over Georgia. It is a perennial herbaceous plant, the alkaloids of which are known for their cytotoxic activity [1]. The alkaloids chelidonine, protopine, L-stylopine, chelerythrine, and berberine were isolated earlier during studies of the species growing in Georgia [2].Herein we communicate results of further research on the composition of alkaloids in C. majus. The specimen was the aerial part of the plant collected near Tbilisi during seed ripening.Ground herb (2 kg) was extracted with EtOH by standing at room temperature. The organic solvent was distilled off. The thick extract was treated with HCl (5%) and then made basic using NH 4 OH (25%). Alkaloids were extracted with CHCl 3 to afford an amorphous total that was separated over a column of silica gel with gradient elution by CHCl 3 :MeOH (1:0o0:1, v/v) to afford two bases that were identified based on an analysis of spectral data compared with the literature. 1 H and 13 C NMR spectra were recorded in CDCl 3 + CD 3 OD on a Bruker-400 spectrometer (400 MHz for 1 H; 100, for 13 C).HPLC analysis of the total was performed on an Agilent-1100 chromatograph using Silicagel-ODS (250 u 6 mm), 25°C, mobile phase H 2 O + AcCN (pH 7.5) at flow rate 1 mL/min. According to an analysis of the results and a comparison with the literature, 2 was identified as tetrahydroberberine [3,5]. REFERENCES1.

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Carbon-13 NMR Shift Assignments of Amines and Alkaloids

Cited by 87 publications

References 0 publications

Chemical constituents from Aspidosperma illustre (Apocynaceae)

Chemical constituents from Aspidosperma illustre (Apocynaceae)

Reactions of 9-Alkyl-3-aminocarbazoles with Ethyl-3-oxo-butanoate and Identification of the Products Obtained

Alkaloids from Chelidonium majus growing in Georgia

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