Glycarpine, a new alkaloid from Glycosmis cyanocarpa

Sarkar, Moumita Biswas; Kundu, Subrata; Chakraborty, D. P.

doi:10.1016/s0031-9422(00)89307-3

Cited by 14 publications

(8 citation statements)

References 2 publications

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“…The ethyl protons appear at 1.52 and 4.57 with a characteristic coupling pattern; the methoxy protons appear as a singlet at 3.92; and the five aromatic protons appear at 6.83 (d, 7=2.5 Hz), 7.03 (ddj=9 Hz, 2.5 Hz), 7.29 (d, 7=2.5 Hz), 7.46(d, 7=2.5 Hz), and 8.08 (d, 7=9 Hz). The 'H-nmr spectrum of 8 shows great resemblance to that of evolitrine (11) (12). The 13C-nmr spectrum of 8 summarized in Table 1 further substantiates the structure assignment.…”

supporting

confidence: 60%

Studies on Heterocyclic Compounds, VI. Synthetic Investigation of Taifine

Kuo¹,

Lin²,

Chang³

et al. 1986

J. Nat. Prod.

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A synthetic approach to the structure reported for the naturally isolated alkaloid named taifine has been developed. The structural assignment is established by spectral data: ir, uv, nmr, and 13C nmr. However, both the spectral and physical properties indicate that synthetic and natural taifine are different in constitution, suggesting the original structure assigned for taifine should be revised.Recently, a novel furo(2, 3-¿)quinolin-4-one named taifine was isolated from Ruta chalepensis L. (Rutaceae) by El-Tawil and co-workers, and was assigned the structure 9ethyl-7-methoxy-4,9-dihydrofuro(2,3-¿)quinolin-4-one (1) purely based upon spectral data (2). As part of our continuing interest in the synthesis and biological activities of furo(2,3-¿)quinolin-4-one derivatives (1), we carried out a synthetic approach to the structure reported for taifine using the modified procedure of Tuppy and Bóhm (3). We now report the results from this synthetic investigation which suggest that the proposed structure for taifine needs reinvestigation. SYNTHETIC RESULTS AND DISCUSSIONThe synthetic approach to taifine is shown in summary form in Scheme 1. Ethyl Scheme 1 'For Part V, see Kuo et al. (1).

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supporting

confidence: 60%

Studies on Heterocyclic Compounds, VI. Synthetic Investigation of Taifine

Kuo¹,

Lin²,

Chang³

et al. 1986

J. Nat. Prod.

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“…The spectral data of the synthetic product (1) were not identical with those described previously for glycarpine (3). In order to confirm the structure of 1, the method of Govindachari (2), which involves the treatment of 5 with excess sodium borohydride and ethanolic alkali, was employed to prepare 1.…”

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confidence: 90%

“…Recently, glycarpine, a novel furo(2, 3-¿)quinolin-4-one alkaloid, was isolated from Glycosmis cyanocarpa Spreng. (Rutaceae) by Sarkar and co-workers (3). The structure of glycarpine was suggested to be 5,7-dimethoxy-9-methyl-4,9-dihydrofuro(2,3-¿)quinolin-4-one (1) based on the spectral evidence.…”

mentioning

confidence: 99%

“…The uv spectrum showed max (EtOH) at 253.5, 333 nm (log 4.45, 4.01), which is very similar to that of isoacronycidine (2). The ir spectrum showed a carbonyl absorption at 1640 cm"1, and the 'H-nmr spectrum (CDC13) exhibited three methyl groups at 3.74 (3H, s, N-CH3), 3.86 (3H, s, 7-OCH3), and 3.89 (3H, s, 5-OCH3). Two protons on the aromatic ring were found at 6.33 (2H, s), and AB quartets were found at 6.91 (H, d,/=2.5 Hz) and 7.14 (H, d,/=2.5 Hz), representing the protons at position 2 and 3 of the fiiran ring.…”

mentioning

confidence: 99%

“…The solvent was partially evaporated and the concentrated residue refrigerated for 2 days. The precipitate was collected and recrystallized from EtOH to afford the tetronic ester ( 4 1.38 (3H, t, -CHj-CHj), 3.80 (6H, s, -OCH3), 4.35 (2H, q, -CH2-CH3), 65.3 (H, s, 4-H), 6.4-6.5 (2H, 2-H, 6-H) and 10.22 (H, s, -NH). Caled for C15H17N06; C 58.63, H 5.53, N 4.56.…”

mentioning

confidence: 99%

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Studies on Heterocyclic Compounds, V. Synthetic Investigation of Glycarpine

Kuo¹,

Lin²,

Lin³

et al. 1984

J. Nat. Prod.

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Chemical studies on alkaloids in the root of Acronychia oligophylebia Merr

Wen-Hao

Zhi

1984

Acta Chim. Sin.

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Nine alkaloids and β‐sitosterol were isolated from the root of Acronychia oligophylebia Merr. (Rutaceae). Among these alkaloids, five were identified as preskimmianine (2), evolitrine (5), kokusaginine (6), skimmianine (7) and maculosidine (8). The alkaloids 2, 5 and 8 were isolated from Acronychia genus for the first time. Oligophylicidine (10) and oligophylidine (4) were new bases. Oligophyline (3) and oligophylicine (9) were first found from natural source. Based on spectroscopic data, the structures of 3, 4, 9 and 10 were postulated. The structures of 10 and 9 were confirmed by synthesis. 3 and 9 showed a wide spectrum of antifungal activity, but the actions were weak.

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Glycarpine, a new alkaloid from Glycosmis cyanocarpa

Cited by 14 publications

References 2 publications

Studies on Heterocyclic Compounds, VI. Synthetic Investigation of Taifine

Studies on Heterocyclic Compounds, VI. Synthetic Investigation of Taifine

Studies on Heterocyclic Compounds, V. Synthetic Investigation of Glycarpine

Chemical studies on alkaloids in the root of Acronychia oligophylebia Merr

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