Acetogenins from Porcelia macrocarpa: Stereochemical determination of 2-alkyl-3-hydroxy-4-methyl γ-lactones by 13C NMR spectroscopy

Chaves, Mariana Helena; Roque, Nı́dia Franca

doi:10.1016/s0031-9422(96)00542-0

Cited by 33 publications

(43 citation statements)

References 7 publications

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“…14, No. 1,2003 The EIMS spectrum of 10 showed the molecular ion peak at m/z 220 Da. The 13 C NMR spectra (BBD and DEPT 135°) displayed fifteen signals refering to three methyls, four methylenes, six methines, as well as two quaternary carbon atoms, suggesting the occurrence of an oxygenated sesquiterpene with molecular formula C 15 H 24 O.…”

Section: Resultsmentioning

confidence: 99%

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Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Chaves¹,

Lago

Roque³

2003

J. Braz. Chem. Soc.

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Section: Resultsmentioning

confidence: 99%

“…In the first one, acetogenins from seeds were reported. 1 Two other papers report the presence of amides, lignanamides and alkaloids from the branches. 2,3 The polar constituents, such as aminoacids, trimethylamonium salts and glycosilated flavonoids were also described.…”

Section: Introductionmentioning

confidence: 99%

Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Chaves¹,

Lago

Roque³

2003

J. Braz. Chem. Soc.

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“…It is well-known that the coupling constants of a five-membered ring cannot provide conclusive evidence for the relative configurations of its substituents. In the case of the compounds above, the trans-configuration of the g-lactone substituents was determined by comparison of their 13 C-NMR chemical shifts with those described for models in the literature [34]. When a Me group is trans to a neighboring OH group, it is shifted downfield to ca.…”

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confidence: 99%

Antimycobacterial Butanolides from the Root of Lindera akoensis

Chang

Cheng

Peng

et al. 2008

Chemistry & Biodiversity

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Three racemic butanolides, majorenolide (1), majorynolide (2), and majoranolide (3), with 18 known compounds, including ten butanolides, i.e., litsenolide A(2) (4), litsenolide B(2) (5), litsenolide C(1) (6), litsenolide C(2) (7), hamabiwalactone A (8), hamabiwalactone B (9), litseakolide A (10), litseakolide B (11), isoobtusilactone (12), and obtusilactone (13); one lignan, i.e., (+/-)-syringaresinol (14), two flavans, i.e., (+)-catechin (15), and (-)-epicatechin (16), one coumarin, i.e., scopoletin (17), and four steroids, i.e., a mixture of beta-sitosterol (18) and stigmasterol (19), and a mixture of beta-sitosteryl-3-O-beta-D-glucoside (20) and stigmasteryl-3-O-beta-D-glucoside (21) were isolated from the root of Lindera akoensis. The structures of the isolates were elucidated by in-depth spectroscopic analysis. Compounds 1-3 were previously assigned a delta-lactone structure, which was then revised to a gamma-lactone structure, based on 1D-NMR data. The cigar-HMBC technique was used to confirm the accuracy of the gamma-lactone structure, and the zero [alpha] (20)_D value of compounds 1-3 suggested that they were considerably racemized. Nine butanolides 1-3, 4-8, and 10 showed antimycobacterial activities against M. tuberculosis H(37)Rv, with MIC values of 15-50 microg/ml.

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“…1 This species has a very diversified chemical composition, revealed by isolation of acetogenins, lignanamides, hydroxycinnamoyltyramines, sesquiterpenes and alkaloids, including azapolycyclics, from different parts, previously investigated, of the same specimen. [2][3][4][5][6] This paper describes the isolation and identification of three steroid mixtures and two flavonoid glycosides from the ethanol extract of the branches of Porcelia macrocarpa.…”

Section: Introductionmentioning

confidence: 99%

Steroids and flavonoids of Porcelia macrocarpa

Chaves¹,

Roque²,

Ayres³

2004

J. Braz. Chem. Soc.

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Três misturas de esteróides (1a+1b, 2a+2b e 3a+3b) e dois flavonóides glicosilados (4 e 5) foram isolados do extrato etanólico dos galhos da Porcelia macrocarpa (Warm.) R. E. Fries (Annonaceae). Os esteróides Estigmasta-4,25-dien-3-ona (2a) e (22E)-Estigmasta-4,22,25-trien-3-ona (2b) são substâncias novas. As estruturas foram determinadas com base na análise de dados espectrais de RMN e de massas e por comparação com dados de substâncias da literatura usadas como modelos.Three mixtures of steroids (1a+1b, 2a+2b and 3a+3b) and two flavonoid glycosides (4 and 5) were isolated from the ethanol extract of branches of Porcelia macrocarpa (Warm.) R. E. Fries (Annonaceae). The steroids Stigmasta-4,25-dien-3-one (2a) and (22E)-Stigmasta-4,22,25-trien-3-one (2b) are news. The structures were elucidated by NMR and MS data and comparison with literature data of model compounds.

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Acetogenins from Porcelia macrocarpa: Stereochemical determination of 2-alkyl-3-hydroxy-4-methyl γ-lactones by 13C NMR spectroscopy

Cited by 33 publications

References 7 publications

Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Antimycobacterial Butanolides from the Root of Lindera akoensis

Steroids and flavonoids of Porcelia macrocarpa

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