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

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 affo...

Full description

Bibliographic Details
Main Authors: Moraes Valéria R. de S., Tomazela Daniela M., Ferracin Ricardo J., Garcia Cleverson F., Sannomiya Míriam, Soriano M. del Pilar C., Silva M. Fátima das G. F. da, Vieira Paulo C., Fernandes João B., Rodrigues Filho Edson, Magalhães Eva G., Magalhães Aderbal F., Pimenta Eli F., Souza Dulce H. F. de, Oliva Glaucius
Format: Article
Language:English
Published: Sociedade Brasileira de Química 2003-01-01
Series:Journal of the Brazilian Chemical Society
Subjects:
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000300007
_version_ 1811232232322367488
author Moraes Valéria R. de S.
Tomazela Daniela M.
Ferracin Ricardo J.
Garcia Cleverson F.
Sannomiya Míriam
Soriano M. del Pilar C.
Silva M. Fátima das G. F. da
Vieira Paulo C.
Fernandes João B.
Rodrigues Filho Edson
Magalhães Eva G.
Magalhães Aderbal F.
Pimenta Eli F.
Souza Dulce H. F. de
Oliva Glaucius
author_facet Moraes Valéria R. de S.
Tomazela Daniela M.
Ferracin Ricardo J.
Garcia Cleverson F.
Sannomiya Míriam
Soriano M. del Pilar C.
Silva M. Fátima das G. F. da
Vieira Paulo C.
Fernandes João B.
Rodrigues Filho Edson
Magalhães Eva G.
Magalhães Aderbal F.
Pimenta Eli F.
Souza Dulce H. F. de
Oliva Glaucius
author_sort Moraes Valéria R. de S.
collection DOAJ
description 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.
first_indexed 2024-04-12T10:58:52Z
format Article
id doaj.art-4d5b8c1a4c464adf85735d591c1485fd
institution Directory Open Access Journal
issn 0103-5053
language English
last_indexed 2024-04-12T10:58:52Z
publishDate 2003-01-01
publisher Sociedade Brasileira de Química
record_format Article
series Journal of the Brazilian Chemical Society
spelling doaj.art-4d5b8c1a4c464adf85735d591c1485fd2022-12-22T03:36:00ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532003-01-01143380387Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)Moraes Valéria R. de S.Tomazela Daniela M.Ferracin Ricardo J.Garcia Cleverson F.Sannomiya MíriamSoriano M. del Pilar C.Silva M. Fátima das G. F. daVieira Paulo C.Fernandes João B.Rodrigues Filho EdsonMagalhães Eva G.Magalhães Aderbal F.Pimenta Eli F.Souza Dulce H. F. deOliva GlauciusOur 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.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000300007RutaceaeLeguminosaeNeoraputiaMurrayaCitrusLonchocarpusTrypanosoma cruzialkaloidflavonoidschemosystematic
spellingShingle Moraes Valéria R. de S.
Tomazela Daniela M.
Ferracin Ricardo J.
Garcia Cleverson F.
Sannomiya Míriam
Soriano M. del Pilar C.
Silva M. Fátima das G. F. da
Vieira Paulo C.
Fernandes João B.
Rodrigues Filho Edson
Magalhães Eva G.
Magalhães Aderbal F.
Pimenta Eli F.
Souza Dulce H. F. de
Oliva Glaucius
Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)
Journal of the Brazilian Chemical Society
Rutaceae
Leguminosae
Neoraputia
Murraya
Citrus
Lonchocarpus
Trypanosoma cruzi
alkaloid
flavonoids
chemosystematic
title Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)
title_full Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)
title_fullStr Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)
title_full_unstemmed Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)
title_short Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)
title_sort enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in neoraputia rutaceae
topic Rutaceae
Leguminosae
Neoraputia
Murraya
Citrus
Lonchocarpus
Trypanosoma cruzi
alkaloid
flavonoids
chemosystematic
url http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000300007
work_keys_str_mv AT moraesvaleriardes enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT tomazeladanielam enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT ferracinricardoj enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT garciacleversonf enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT sannomiyamiriam enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT sorianomdelpilarc enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT silvamfatimadasgfda enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT vieirapauloc enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT fernandesjoaob enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT rodriguesfilhoedson enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT magalhaesevag enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT magalhaesaderbalf enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT pimentaelif enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT souzadulcehfde enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae
AT olivaglaucius enzymaticinhibitionstudiesofselectedflavonoidsandchemosystematicsignificanceofpolymethoxylatedflavonoidsandquinolinealkaloidsinneoraputiarutaceae