Dihydroperfamine, an alkaloid from haplophyllum glabrinum

Rózsa, Zs.; Rábik, M.; Szendrei, K.; Kàlmán, Alajos; Argay, Gy.; Pelczer, István; Aynechi, M.; Mester, L.; Reisch, J.

doi:10.1016/s0031-9422(00)81200-5

Cited by 15 publications

(3 citation statements)

References 4 publications

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“…10 The HSQC and HMBC experiments on flindersine, permitted minor corrections to previous 13 C NMR assignments. 10 Table 1 shows that the signals for C-3 and C-10 to C-12 were reassigned.…”

Section: Resultsmentioning

confidence: 99%

“…10 The HSQC and HMBC experiments on flindersine, permitted minor corrections to previous 13 C NMR assignments. 10 Table 1 shows that the signals for C-3 and C-10 to C-12 were reassigned. The observed correlations between the methine hydrogen signal at δ 6.77 and the The methanolic extract from stems afforded skimmianine, 11 8-methoxyflindersine (2) 12 and dictamnine.…”

Section: Resultsmentioning

confidence: 99%

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Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)

Moraes

Tomazela

Ferracin

et al. 2003

J. Braz. Chem. Soc.

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Nosso interesse quimiotaxonômico sobre Neoraputia nos estimulou a examinar N. paraensis, visando a busca de alcalóides. As frações foram monitoradas via RMN 1 H e ESI-EM/EM e foram analisadas somente aquelas cujos espectros apresentavam características de alcalóides do ácido antranílico e flavonóides não isolados anteriormente. Foram isolados do caule os alcalóides flindersina, skimmianina, 8-metoxiflindersina e dictamnina; das folhas os flavonóides 3',4',7,8-tetrametoxi-5,6-(2",2"-dimetilpirano)-flavona, 3',4',5,7,8-pentametoxiflavona, 5-hidroxi-3',4',6,7-tetrametoxiflavona, 3',4'-metilenodioxi-5,6,7-trimetoxiflavona e 5-hidroxi-3',4'-metilenodioxi-6,7-dimetoxiflavona,. Os alcalóides do ácido antranílico não foram encontrados em dez anos.Vários flavonóides isolados de N. paraensis, N. magnifica, Murraya paniculata, enxerto de Citrus sinensis (Rutaceae) e Lonchocarpus montanus (Leguminosae) foram testados frente a gliceraldeído-3-fosfato desidrogenase de Trypanosoma cruzi, visando verificar seus potenciais em inibir a atividade da enzima. Os flavonóides polimetoxilados e um isoflavonóide foram os mais ativos.Our taxonomic interest in the Neoraputia stimulated an investigation of N. paraensis searching for alkaloids. Fractions were monitored by 1 H NMR and ESI-MS/MS and only those which showed features of anthranilate alkaloids and flavonoids absent in the previous investigations were examined. Stems afforded the alkaloids flindersine, skimmianine, 8-methoxyflindersine and dictamnine; leaves yielded 3',4',7,8-tetramethoxy-5,6-(2",2"-dimethylpyrano)-flavone, 3',4',5,7,8-pentamethoxyflavone, 5-hydroxy-3',4',6,7-tetramethoxyflavone, 3',4'-methylenedioxy-5,6,7-trimethoxyflavone and 5-hydroxy-3',4'-methylenedioxy-6,7-dimethoxyflavone. The alkaloids have remained undiscovered for 10 years.A number of flavonoids isolated from N. paraensis, N. magnifica, Murraya paniculata, Citrus sinensis graft (Rutaceae), Lonchocarpus montanus (Leguminosae) were evaluated for their ability to inhibit the enzymatic activity of the protein glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi. Highly oxygenated flavones and isoflavone were the most actives.

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“…10 The HSQC and HMBC experiments on flindersine, permitted minor corrections to previous 13 C NMR assignments. 10 Table 1 shows that the signals for C-3 and C-10 to C-12 were reassigned.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)

Moraes

Tomazela

Ferracin

et al. 2003

J. Braz. Chem. Soc.

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“…2,11 In order to improve the therapy of Chagas disease, we have been studying species of the order Rutales (Rutaceae, Meliaceae, Simaroubaceae, Burseraceae, and Cneoraceae) aiming to isolate hit compounds that could be used in the development of new antichagasic drugs.…”

Section: A Rel-(7r8r)-8-[(e)-3-hydroxy-3-methyl-1-butenyl]-mentioning

confidence: 99%

New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

Ambrozin¹,

Mafezoli²,

Vieira³

et al. 2005

J. Braz. Chem. Soc.

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O estudo da fração acetato de etila do extrato metanólico das folhas de Almeidea rubra A. St.-Hil. (Rutaceae) permitiu o isolamento de duas substâncias inéditas: 4-metoxi-6-[2-(metilamino)fenil]-2H-piran-2-ona e acetato de rel-(7R,8R)-8-[(E)-3-hidroxi-3-metil-1-butenil]-4,8-dimetoxi-5,6,7,8-tetraidrofuro[2,3-b]quinolin-7-ila; e dos alcalóides arborinina, N-metil-1-hidroxi-3-metoxiacridona, esquimianina, cocusagina, isodutaduprina, isoesquimianina e isococusagina. Através da análise dos dados espectroscópicos foram estabelecidas as estruturas químicas das substâncias isoladas sendo que para os alcalóides inéditos tais dados são descritos pela primeira vez. Além disso, os ensaios bilógicos sobre as formas tripomastigotas do Trypanosoma cruzi das substâncias isoladas mostraram que elas possuem atividade tripanocida moderada.The investigation of the ethyl acetate fraction of methanol extract from leaves of Almeidea rubra A. St.-Hil. (Rutaceae) afforded two new compounds 4-methoxy-6-[2-(methylamino)phenyl]-2H-pyran-2-one and rel-(7R,8R)-8- [(E)-3-hydroxy-3-methyl-1-butenyl]-4,8-dimethoxy-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-7-yl acetate, along with the known compounds arborinine, N-methyl-1-hydroxy-3-methoxyacridone, skimmianine, kokusagine, isodutaduprine, isoskimmianine, and isokokusagine. Their structures were established based on their spectral data, and for the new compounds these data are described herein. Additionally, these compounds were assayed on the tripomastigote forms of Trypanosoma cruzi showing moderate trypanocidal activity.

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Haplophyllum patavinum (L.) G. Don fil. (Paduan rue): In Vitro Regeneration, and the Production of Coumarin Compounds

Cappelletti

Innocenti

Caniato

et al. 1998

Biotechnology in Agriculture and Forestry

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Dihydroperfamine, an alkaloid from haplophyllum glabrinum

Cited by 15 publications

References 4 publications

Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)

Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)

New pyrone and quinoline alkaloid from Almeidea rubra and their trypanocidal activity

Haplophyllum patavinum (L.) G. Don fil. (Paduan rue): In Vitro Regeneration, and the Production of Coumarin Compounds

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