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Flavonol monoglycosides isolated from the antiviral fractions ofPersea americana (Lauraceae) leaf infusion

1998; Wiley; Volume: 12; Issue: 8 Linguagem: Inglês

10.1002/(sici)1099-1573(199812)12

1099-1573

Ana Paula de Almeida, M. M. F. S. Miranda, Isabela Cristina Simoni, M.D. Wigg, M. H. C. Lagrota, Sônia Soares Costa,

Herpesvirus Infections and Treatments

Phytotherapy ResearchVolume 12, Issue 8 p. 562-567 Original Paper Flavonol monoglycosides isolated from the antiviral fractions of Persea americana (Lauraceae) leaf infusion A. P. de Almeida, A. P. de Almeida Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this authorM. M. F. S. Miranda, M. M. F. S. Miranda Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this authorI. C. Simoni, I. C. Simoni Instituto Biológico de São Paulo, Seção de Biologia Celular, Cx Postal 7119, São Paulo, SP, BrazilSearch for more papers by this authorM. D. Wigg, M. D. Wigg Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this authorM. H. C. Lagrota, M. H. C. Lagrota Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this authorS. S. Costa, Corresponding Author S. S. Costa Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilNúcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this author A. P. de Almeida, A. P. de Almeida Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this authorM. M. F. S. Miranda, M. M. F. S. Miranda Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this authorI. C. Simoni, I. C. Simoni Instituto Biológico de São Paulo, Seção de Biologia Celular, Cx Postal 7119, São Paulo, SP, BrazilSearch for more papers by this authorM. D. Wigg, M. D. Wigg Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this authorM. H. C. Lagrota, M. H. C. Lagrota Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this authorS. S. Costa, Corresponding Author S. S. Costa Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilNúcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, 21 941-590 Rio de Janeiro, RJ, BrazilSearch for more papers by this author First published: 21 December 1998 https://doi.org/10.1002/(SICI)1099-1573(199812)12:8 3.0.CO;2-6Citations: 67AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract An infusion of Persea americana leaves (Lauraceae) strongly inhibited herpes simplex virus type 1 (HSV-1), Aujeszky's disease virus (ADV) and adenovirus type 3 (AD3) in cell cultures. Its fractionation, guided by anti-HSV-1 and ADV assays, allowed the isolation and identification of two new flavonol monoglycosides, kaempferol and quercetin 3-O-α-D-arabinopyranosides, along with the known kaempferol 3-O-α-L-rhamnopyranoside (afzelin), quercetin 3-O-α-L-rhamnopyranoside (quercitrin), quercetin 3-O-β-glucopyranoside and quercetin. The known quercetin 3-O-β-galactopyranoside was identified in a mixture. Afzelin and quercetin 3-O-α-D-arabinopyranoside showed higher activity against acyclovir-resistant HSV-1. Chlorogenic acid significantly inhibited the HSV-1 replication without any cytotoxicity. However, all the substances tested were less active than the infusion or fractions. The same substances did not affect ADV replication. Chemical structures were elucidated by the analysis of UV, 1H and 13C NMR data, mainly by APT, homo and heteronuclear COSY experiments. The configuration of the D-arabinose unit, not usual in natural plant products, was established on the basis of the optical rotation of the free sugar obtained after acid hydrolysis. Copyright © 1998 John Wiley & Sons, Ltd. References Adikaram, N. K. B., Ewing, D. F., Karunaratne, A. M., and Wijeratne, E. M. K. (1992). Antifungal compounds from immature Avocado fruit peel. Phytochemistry 3, 93–96. Alves, H. M., Coxon, D. T., Falshaw, C. P., Godtfredsen, W. O., and Ollis, W. D. (1970). The Avocatins — A new class of natural products. An. Acad. Brasil. Cienc. 42, (suplemento), 39–43. Amoros, M., Simoes, C. M. O., and Girre, L. (1992). Synergistic effect of flavones and flavonols against herpes simplex virus type 1 in cell culture. Comparison with the antiviral activity of propolis. J. Nat. 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