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Jean Duplex Wansi - One of the best experts on this subject based on the ideXlab platform.
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antimicrobial furoquinoline alkaloids from vepris lecomteana pierre cheek t heller rutaceae
Molecules, 2017Co-Authors: Ariane Dolly Kenmogne Kouam, Achille Nouga Bissoue, Alain Tadjong Tcho, Emmanuel Ngeufa Happi, Alain Francois Kamdem Waffo, Norbert Sewald, Jean Duplex WansiAbstract:Three new prenylated furoquinoline alkaloids named lecomtequinoline A (1), B (2), and C (3), together with the known compounds anhydroevoxine (4), evoxine (5), Dictamnine (6), N-methylflindersine (7), evoxanthine (8), hesperidin, lupeol, β-sitosterol, stigmasterol, β-sitosterol-3-O-β-d-glucopyranoside, stearic acid, and myristyl alcohol, were isolated by bioassay-guided fractionation of the methanolic extracts of leaves and stem of Vepris lecomteana. The structures of compounds were determined by spectroscopic methods (NMR, MS, UV, and IR) and by comparison with previously reported data. Crude extracts of leaves and stem displayed high antimicrobial activity, with Minimum Inhibitory Concentration (MIC) (values of 10.1–16.5 and 10.2–20.5 µg/mL, respectively, against Escherichia coli, Bacillus subtilis, Pseudomonas agarici, Micrococcus luteus, and Staphylococcus warneri, while compounds 1–6 showed values ranging from 11.1 to 18.7 µg/mL or were inactive, suggesting synergistic effect. The extracts may find application in crude drug preparations in Western Africa where Vepris lecomteana is endemic, subject to negative toxicity results in vivo.
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Antimicrobial Furoquinoline Alkaloids from Vepris lecomteana (Pierre) Cheek & T. Heller (Rutaceae)
MDPI AG, 2017Co-Authors: Ariane Dolly Kenmogne Kouam, Achille Nouga Bissoue, Alain Tadjong Tcho, Emmanuel Ngeufa Happi, Alain Francois Kamdem Waffo, Norbert Sewald, Jean Duplex WansiAbstract:Three new prenylated furoquinoline alkaloids named lecomtequinoline A (1), B (2), and C (3), together with the known compounds anhydroevoxine (4), evoxine (5), Dictamnine (6), N-methylflindersine (7), evoxanthine (8), hesperidin, lupeol, β-sitosterol, stigmasterol, β-sitosterol-3-O-β-d-glucopyranoside, stearic acid, and myristyl alcohol, were isolated by bioassay-guided fractionation of the methanolic extracts of leaves and stem of Vepris lecomteana. The structures of compounds were determined by spectroscopic methods (NMR, MS, UV, and IR) and by comparison with previously reported data. Crude extracts of leaves and stem displayed high antimicrobial activity, with Minimum Inhibitory Concentration (MIC) (values of 10.1–16.5 and 10.2–20.5 µg/mL, respectively, against Escherichia coli, Bacillus subtilis, Pseudomonas agarici, Micrococcus luteus, and Staphylococcus warneri, while compounds 1–6 showed values ranging from 11.1 to 18.7 µg/mL or were inactive, suggesting synergistic effect. The extracts may find application in crude drug preparations in Western Africa where Vepris lecomteana is endemic, subject to negative toxicity results in vivo
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New furoquinoline alkaloid and flavanone glycoside derivatives from the leaves of Oricia suaveolens and Oricia renieri (Rutaceae).
Natural product research, 2015Co-Authors: Achille Nouga, Jean Claude Ndom, Emmanuel Mpondo Mpondo, Judith Caroline Ngo Nyobe, Alain Njoya, Luc Mbaze Meva’a, Phillipa B. Cranwell, James A. S. Howell, Laurence M. Harwood, Jean Duplex WansiAbstract:Fractionation of the methanol extract of the leaves of Oricia renieri and Oricia suaveolens (Rutaceae) led to the isolation of 13 compounds including the hitherto unknown furoquinoline alkaloid named 6,7-methylenedioxy-5-hydroxy-8-methoxy-Dictamnine (1) and a flavanone glycoside named 5-hydroxy-4′-methoxy-7-O-[α-l-rhamnopyranosyl(1‴→5″)-β-d-apiofuranosyl]-flavanoside (2), together with 11 known compounds (3–13). The structures of the compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral data and comparison. All compounds isolated were examined for their activity against human carcinoma cell lines. The alkaloids 1, 5, 12, 13 and the phenolic 2, 8, 11 tested compounds exhibited non-selective moderate cytotoxic activity with IC50 8.7–15.9 μM whereas compounds 3, 4, 6, 7, 9 and 10 showed low activity.
Christopher C. R. Allen - One of the best experts on this subject based on the ideXlab platform.
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biphenyl dioxygenase catalysed cis dihydroxylation of tricyclic azaarenes chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids
RSC Advances, 2013Co-Authors: Derek R. Boyd, Jonathan G Carroll, Pui L Loke, Colin Odowd, Narain D. Sharma, Christopher C. R. AllenAbstract:Biotransformation of acridine, Dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings. cis-Dihydroxylation of the furan ring in Dictamnine and 4-chlorofuro[2,3-b]quinoline, followed by ring opening and reduction, yielded two exocyclic diols. The structures and absolute configurations of metabolites have been determined by spectroscopy and stereochemical correlation methods. Enantiopure arene oxide metabolites of acridine and Dictamnine have been synthesised, from the corresponding cis-dihydrodiols. The achiral furoquinoline alkaloids robustine, γ-fagarine, haplopine, isohaplopine-3,3′-dimethylallylether and pteleine have been obtained, from either cis-dihydrodiol, catechol or arene oxide metabolites of Dictamnine.
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cis dihydrodiol arene oxide and phenol metabolites of Dictamnine key intermediates in the biodegradation and biosynthesis of furoquinoline alkaloids
Chemical Communications, 2005Co-Authors: Derek R. Boyd, Jonathan G Carroll, Pui L Loke, Colin Odowd, Narain D. Sharma, Christopher C. R. AllenAbstract:Biotransformation of the parent furoquinoline alkaloid Dictamnine and its 4-chlorofuroquinoline precursor, using the B8/36 bacterial mutant strain of Sphingomonas yanoikuyae, yielded, via biphenyl dioxygenase-catalysed dihydroxylation, the first isolable alkaloid cis-dihydrodiol metabolites; these metabolites were used in the chemoenzymatic synthesis of postulated arene oxide and phenol intermediates, and a range of derived furoquinoline alkaloids.
Vieira,paulo C. - One of the best experts on this subject based on the ideXlab platform.
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Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)
Sociedade Brasileira de Química, 2015Co-Authors: Moraes, Valéria R. De S., Fernandes,joão B., Vieira,paulo C., Fatima Das M G F Da Silva, Tomazela, Daniela M., Ferracin, Ricardo J., Garcia, Cleverson F., Sannomiya Míriam, Soriano M. Del Pilar C., Rodrigues Filho EdsonAbstract:Our taxonomic interest in the Neoraputia stimulated an investigation of N. paraensis searching for alkaloids. Fractions were monitored by ¹H 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.Nosso interesse quimiotaxonômico sobre Neoraputia nos estimulou a examinar N. paraensis, visando a busca de alcalóides. As frações foram monitoradas via RMN ¹H 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
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Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)
'FapUNIFESP (SciELO)', 2015Co-Authors: Moraes, Valéria R. De S., Fernandes,joão B., Vieira,paulo C., Fatima Das M G F Da Silva, Tomazela, Daniela M., Ferracin, Ricardo J., Garcia, Cleverson F., Sannomiya Míriam, Soriano M. Del Pilar C., Rodrigues Filho EdsonAbstract:Our taxonomic interest in the Neoraputia stimulated an investigation of N. paraensis searching for alkaloids. Fractions were monitored by ¹H 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.Nosso interesse quimiotaxonômico sobre Neoraputia nos estimulou a examinar N. paraensis, visando a busca de alcalóides. As frações foram monitoradas via RMN ¹H 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.380387Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES
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Prenylindole alkaloids from Raputia praetermissa (Rutaceae) and their chemosystematic significance
Sociedade Brasileira de Química, 2011Co-Authors: Veiga,thiago André M, Fernandes,joão B., Vieira,paulo C., Fatima Das M G F Da SilvaAbstract:The dichloromethane extract from the stems of Raputia praetermissa afforded four new compounds, 4-deoxyraputindole C (1), raputimonoindoleA-B (2, 3), and hexadecanyl 2-hydroxy-4-methoxy-cinnamate (5), besides the alkaloids 5-(4-methoxymethylfuran-2-yl)-1H-indole (raputimonoindole C), furoquinolines maculosidine, robustine, evolitrine and Dictamnine. The hexane extract yielded N-methyl-4-methoxyquinolin-2(1H)-one, skimmianine, cycloartenone, sitosterol, stigmasterol and sitostenone. The anthranilate alkaloid content indicates that the genus is strongly related to those included in Cusparieae tribe, but differs from Neoraputia by the absence of prenylindole alkaloids in the late, whose species have previously been placed in Raputia
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Activities of extracts and compounds from Spiranthera odoratissima St. Hil. (Rutaceae) in leaf-cutting ants and their symbiotic fungus
Sociedade Brasileira de Química, 2010Co-Authors: Terezan,ana Paula, Rossi,raquel Andrade, Almeida,roberta N. A., Freitas,taís Garcia, Fernandes,joão B., Fátima Das Graças Fernandes M. Da ,silva, Vieira,paulo C., Bueno,odair C., Pagnocca,fernando C., Pirani,josé R.Abstract:The study of the Spiranthera odoratissima St. Hil (Rutaceae) branches extracts led to the isolation of the furoquinoline (dictamine, γ-fagarine and skimmianine) and 2-arylquinoli-4-one (1-methyl-2-phenylquinolin-4-one) alkaloids and limonoids (limonexic acid and limonin). The compounds 1-methyl-2-phenylquinolin-4-one and limonexic acid were isolated for the first time from the Spiranthera. These furoquinoline and 2-arylquinoli-4-one alkaloids and limonoids showed insecticidal and/or fungicidal activity in the nest of the Atta sexdens rubropilosa
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Activities of Extracts and Compounds from Spiranthera odoratissima St. Hil. (Rutaceae) in Leaf-cutting Ants and their Symbiotic Fungus
Soc Brasileira Quimica, 2010Co-Authors: Terezan,ana Paula, Rossi,raquel Andrade, Almeida,roberta N. A., Freitas,taís Garcia, Fernandes,joão B., Vieira,paulo C., Bueno,odair C., Gracas Fernandes Da Silva, M. Fatima Das, Pagnocca, Fernando Carlos, Pirani,josé R.Abstract:The study of the Spiranthera odoratissima St. Hil (Rutaceae) branches extracts led to the isolation of the furoquinoline (dictamine, gamma-fagarine and skimmianine) and 2-arylquinoli-4-one (1-methyl-2-phenylquinolin-4-one) alkaloids and limonoids (limonexic acid and limonin). The compounds 1-methyl-2-phenylquinolin-4-one and limonexic acid were isolated for the first time from the Spiranthera. These furoquinoline and 2-arylquinoli-4-one alkaloids and limonoids showed insecticidal and/or fungicidal activity in the nest of the Atta sexdens rubropilosa.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES
Pirani,josé R. - One of the best experts on this subject based on the ideXlab platform.
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Activities of extracts and compounds from Spiranthera odoratissima St. Hil. (Rutaceae) in leaf-cutting ants and their symbiotic fungus
Sociedade Brasileira de Química, 2010Co-Authors: Terezan,ana Paula, Rossi,raquel Andrade, Almeida,roberta N. A., Freitas,taís Garcia, Fernandes,joão B., Fátima Das Graças Fernandes M. Da ,silva, Vieira,paulo C., Bueno,odair C., Pagnocca,fernando C., Pirani,josé R.Abstract:The study of the Spiranthera odoratissima St. Hil (Rutaceae) branches extracts led to the isolation of the furoquinoline (dictamine, γ-fagarine and skimmianine) and 2-arylquinoli-4-one (1-methyl-2-phenylquinolin-4-one) alkaloids and limonoids (limonexic acid and limonin). The compounds 1-methyl-2-phenylquinolin-4-one and limonexic acid were isolated for the first time from the Spiranthera. These furoquinoline and 2-arylquinoli-4-one alkaloids and limonoids showed insecticidal and/or fungicidal activity in the nest of the Atta sexdens rubropilosa
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Activities of Extracts and Compounds from Spiranthera odoratissima St. Hil. (Rutaceae) in Leaf-cutting Ants and their Symbiotic Fungus
Soc Brasileira Quimica, 2010Co-Authors: Terezan,ana Paula, Rossi,raquel Andrade, Almeida,roberta N. A., Freitas,taís Garcia, Fernandes,joão B., Vieira,paulo C., Bueno,odair C., Gracas Fernandes Da Silva, M. Fatima Das, Pagnocca, Fernando Carlos, Pirani,josé R.Abstract:The study of the Spiranthera odoratissima St. Hil (Rutaceae) branches extracts led to the isolation of the furoquinoline (dictamine, gamma-fagarine and skimmianine) and 2-arylquinoli-4-one (1-methyl-2-phenylquinolin-4-one) alkaloids and limonoids (limonexic acid and limonin). The compounds 1-methyl-2-phenylquinolin-4-one and limonexic acid were isolated for the first time from the Spiranthera. These furoquinoline and 2-arylquinoli-4-one alkaloids and limonoids showed insecticidal and/or fungicidal activity in the nest of the Atta sexdens rubropilosa.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES
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A new imidazole alkaloid and other constituents from Pilocarpus grandiflorus and their antifungal activity
2005Co-Authors: De Souza, Rejane C., Fernandes,joão B., Vieira,paulo C., Bueno,odair C., Pagnocca,fernando C., Da Silva, Fátima Das M. G. F., Godoy, Marizete F. P., Hebling, José M. A., Pirani,josé R.Abstract:The stems of Pilocarpus grandiflorus have afforded the new imidazole alkaloid 4,6-dehydro-1,2,4,5-tetrahydro-2,5-dioxopilocarpine in addition to the 17 known compounds germanicol, β-amiryn, ocotillone, stigmast-4-en-3-one, 3β-hydroxy-stigmast-5-en-7-one, 6β-hydroxy-stigmast-4-en-3-one, β-sitosterol, scopoletin, 3-(1′,1′-dimethylallyl)-scopoletin, elisin, dictamine, 4-methoxy-2-quinolone, platydesmine, syringaresinol, syringaldehyde, syringic acid and vanillic acid. Their structures were elucidated on the basis of chemical and spectroscopic evidence. The phenolic compounds vanillic acid and syringaldehyde and the furoquinoline alkaloid platydesmine exhibited antifungal activity against Leucoagaricus gongylophorus, the symbiotic fungus of leaf-cutting ants (Atta sexdens rubropilosa). © 2005 Verlag der Zeitschrift für Naturforschung
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Cycloartane Triterpenoid and Alkaloids from Ameidea SPP
Sociedade Brasileira de Química, 1998Co-Authors: Santos,celcione S., Fernandes,joão B., Vieira,paulo C., Januário,ana H., Fátima G.f. M. Da ,silva, Pirani,josé R.Abstract:A new triterpene 3-beta-tiglyl-24-methylcycloartanol jointly with a mixture containing 3beta-hydroxy-urs-12-ene-28-oic and 3beta-hydroxy-olean-12-ene-28-oic acids were isolated from Almeidea coerulea. In addition to the triterpenes five alkaloids were also isolated from the same plant: 7-O-acetylhaplophyllidine, dutadrupine, isodutadrupine, 7-methoxy-8-(3,3-dimethylallyl)-Dictamnine and arborinine. From A. rubra, the alkaloids arborinine, methylarborinine, evolitrine, skimmianine, kokusagine and folinine were isolated. Their structures were established based on their spectral data. The alkaloids 7-methoxy-8-(dimethylallyl)-Dictamnine and 7-O-acetylhaplophyllidine are described for the first time as natural products
Derek R. Boyd - One of the best experts on this subject based on the ideXlab platform.
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biphenyl dioxygenase catalysed cis dihydroxylation of tricyclic azaarenes chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids
RSC Advances, 2013Co-Authors: Derek R. Boyd, Jonathan G Carroll, Pui L Loke, Colin Odowd, Narain D. Sharma, Christopher C. R. AllenAbstract:Biotransformation of acridine, Dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings. cis-Dihydroxylation of the furan ring in Dictamnine and 4-chlorofuro[2,3-b]quinoline, followed by ring opening and reduction, yielded two exocyclic diols. The structures and absolute configurations of metabolites have been determined by spectroscopy and stereochemical correlation methods. Enantiopure arene oxide metabolites of acridine and Dictamnine have been synthesised, from the corresponding cis-dihydrodiols. The achiral furoquinoline alkaloids robustine, γ-fagarine, haplopine, isohaplopine-3,3′-dimethylallylether and pteleine have been obtained, from either cis-dihydrodiol, catechol or arene oxide metabolites of Dictamnine.
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cis dihydrodiol arene oxide and phenol metabolites of Dictamnine key intermediates in the biodegradation and biosynthesis of furoquinoline alkaloids
Chemical Communications, 2005Co-Authors: Derek R. Boyd, Jonathan G Carroll, Pui L Loke, Colin Odowd, Narain D. Sharma, Christopher C. R. AllenAbstract:Biotransformation of the parent furoquinoline alkaloid Dictamnine and its 4-chlorofuroquinoline precursor, using the B8/36 bacterial mutant strain of Sphingomonas yanoikuyae, yielded, via biphenyl dioxygenase-catalysed dihydroxylation, the first isolable alkaloid cis-dihydrodiol metabolites; these metabolites were used in the chemoenzymatic synthesis of postulated arene oxide and phenol intermediates, and a range of derived furoquinoline alkaloids.