title: Ingasaponin, a complex triterpenoid saponin with immunological adjuvant activity from Inga laurina.
abstract: As part of our search of bioactive saponins from Brazilian plants, phytochemical study of the seeds of Inga laurina led to the isolation of a new complex triterpenoid saponin, named ingasaponin. It is the first saponin isolated from a species of Inga genus. It was isolated by using chromatographic methods and its structural elucidation was performed using detailed analyses of (1)H and (13)C NMR spectra including 2D-NMR spectroscopic techniques and chemical conversions. Its structure was established as 21-[[(2E,6S)-6-[[6-deoxy-4-O-[(2E,6S)-6-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-[(β-D-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]oxy]-16-hydroxy-3-[[O-β-D-xylopyranosyl-(1 → 2)-O-α-L-arabinopyranosyl-(1 → 6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-(3β,16α,21β)-olean-12-en-28-oic acid O-α-L-arabinofuranosyl-(1 → 4)-O-[β-D-glucopyranosyl-(1 → 3)]-O-6-deoxy-α-L-mannopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (1). The hemolytic potential of 1 was evaluated using in vitro assays, and its adjuvant activity on the cellular immune response against ovalbumin antigen was investigated using in vivo models.
authors.affiliation: Laboratório de Química de Plantas Medicinais, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, P.O. Box 68045, CEP 21941-971 Rio de Janeiro, Brazil.
authors.forename: Maria de Fátima Simão Jucá
authors.initials: Mde F
authors.lastname: Cruz
authors.affiliation: Laboratório de Química de Plantas Medicinais, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, P.O. Box 68045, CEP 21941-971 Rio de Janeiro, Brazil.
authors.forename: Gabriela Moysés
authors.initials: GM
authors.lastname: Pereira
authors.affiliation: Laboratório de Química de Plantas Medicinais, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, P.O. Box 68045, CEP 21941-971 Rio de Janeiro, Brazil.
authors.forename: Marcela Gonçalves
authors.initials: MG
authors.lastname: Ribeiro
authors.affiliation: Laboratório de Química de Plantas Medicinais, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, P.O. Box 68045, CEP 21941-971 Rio de Janeiro, Brazil.
authors.forename: Ari Miranda
authors.initials: AM
authors.lastname: da Silva
authors.affiliation: Laboratório Multiusuário de Análises por Ressonância Magnética Nuclear, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, CEP 21941-902 Rio de Janeiro, Brazil.
authors.forename: Luzineide Wanderley
authors.initials: LW
authors.lastname: Tinoco
authors.affiliation: Laboratório de Química de Plantas Medicinais, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, P.O. Box 68045, CEP 21941-971 Rio de Janeiro, Brazil.
authors.forename: Bernadete Pereira
authors.initials: BP
authors.lastname: da Silva
authors.affiliation: Laboratório de Química de Plantas Medicinais, Instituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, P.O. Box 68045, CEP 21941-971 Rio de Janeiro, Brazil. Electronic address: parente@pq.cnpq.br.
authors.forename: José Paz
authors.initials: JP
authors.lastname: Parente
mesh_terms: D000276:Adjuvants, Immunologic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D004912:Erythrocytes / Q000166:cytology / Q000187:drug effects; D007887:Fabaceae / Q000737:chemistry*; D008297:Male; D051379:Mice; D015394:Molecular Structure; D010047:Ovalbumin / Q000008:administration & dosage / Q000276:immunology; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000276:Adjuvants, Immunologic; D012503:Saponins; D014315:Triterpenes; D010047:Ovalbumin
keywords: Adjuvant activity; Complex triterpenoid saponin; Hemolytic property; Inga laurina; Ingasaponin; Leguminosae