1-Cinnamoyl-3,11-dihydroxymeliacarpin is a natural bioactive compound with antiviral and nuclear factor-κB modulating properties

We have reported the isolation of the tetranortriterpenoid 1-cinnamoyl-3,11-dihydroxymeliacarpin (CDM) from partially purified leaf extracts of Melia azedarach L. (MA) that reduced both, vesicular stomatitis virus (VSV) and Herpes simplex virus type 1 (HSV-1) multiplication. CDM blocks VSV entry and...

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Autor principal: Barquero, A.A
Otros Autores: Michelini, F.M, Alché, L.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2006
Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-33745270082 
024 7 |2 cas  |a 1-cinnamoyl-3,11-dihydroxymeliacarpin; Antiviral Agents; Limonins; NF-kappa B 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a BBRCA 
100 1 |a Barquero, A.A. 
245 1 0 |a 1-Cinnamoyl-3,11-dihydroxymeliacarpin is a natural bioactive compound with antiviral and nuclear factor-κB modulating properties 
260 |c 2006 
270 1 0 |m Barquero, A.A.; Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Pabellon II, Piso 4to., Ciudad Univ., C1428BGA Buenos Aires, Argentina; email: alecab@qb.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Haridas, V., Arntzen, C., Gutterman, J., Avicins, a family of triterpenoids saponins from Acacia victoriae (Bentham), inhibit activation of nuclear factor-κB by inhibiting both its nuclear localization and ability to bind DNA (2001) Proc. Natl. Acad. Sci. USA, 98, pp. 11557-11562 
504 |a Jung, H., Nam, J., Choi, J., Lee, K., Park, H., 19 Alpha-hydroxyursane-type triterpenoids: antinociceptive anti-inflammatory principles of the roots of Rosa rugosa (2005) Biol. Pharm. Bull., 28, pp. 101-104 
504 |a Battinelli, L., Mengoni, F., Lichtner, M., Mazzanti, G., Saija, A., Mastroianni, C., Vullo, V., Effect of limonin and nomilin on HIV-1 replication on infected human mononuclear cells (2003) Planta Med., 69, pp. 910-913 
504 |a Ikeda, T., Yokomizo, K., Okawa, M., Tsuchihashi, R., Kinjo, J., Nohara, T., Uyeda, M., Anti-herpes virus type 1 activity of oleanane-type triterpenoids (2005) Biol. Pharm. Bull., 28, pp. 1779-1781 
504 |a Alché, L., Assad Ferek, G., Meo, M., Coto, C., Maier, M., An antiviral meliacarpin from leaves of Melia azedarach L. (2003) Z. Naturforsch. Sect. C, 58 c (3-4), pp. 215-219 
504 |a Barquero, A., Alché, L., Coto, C., Block of VSV endocytic and exocytic pathways by 1-cinnamoyl-3,11-dihydroxymeliacarpin, a tetranortriterpenoid of natural origin (2004) J. Gen. Virol., 85, pp. 483-493 
504 |a Pifarré, M., Berra, A., Coto, C., Alché, L., Therapeutic action of meliacine, a plant-derived antiviral, on HSV-induced ocular disease in mice (2002) Exp. Eye Res., 75, pp. 327-334 
504 |a Hiscott, J., Kwon, H., Genin, P., Hostile takeovers: viral appropriation of the NF-kappaB pathway (2001) J. Clin. Invest., 107, pp. 143-151 
504 |a Diebold, Y., Calonge, M., Enriquez de Salamanca, A., Callejo, S., Corrales, R., Saez, V., Siemasko, K., Stern, M., Characterization of a spontaneously immortalized cell line (IOBA-NHC) from normal human conjunctiva (2003) Invest. Ophthalmol. Vis. Sci., 44, pp. 4263-4274 
504 |a Giraudo, C., Daniotti, J., Maccioni, H., Physical and functional association of glycolipid N-acetyl-galactosaminyl and galactosyl transferases in the Golgi apparatus (2001) Proc. Natl. Acad. Sci. USA, 98, pp. 1625-1630 
504 |a Michelini, F., Ramírez, J., Berra, A., Galagovsky, L., Alché, L., In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues (2004) Steroids, 69, pp. 713-720 
504 |a Gregory, D., Hargett, D., Holmes, D., Money, E., Bachenheimer, S., Efficient replication by herpes simplex virus type 1 involves activation of the IkappaB kinase-IkappaB-p65 pathway (2004) J. Virol., 78, pp. 13582-13590 
504 |a Vermani, K., Garg, S., Herbal medicines for sexually transmitted diseases and AIDS (2002) J. Ethnopharmacol., 80, pp. 49-66 
504 |a Alché, L., Barquero, A., Sanjuan, N., Coto, C., An antiviral principle present in a purified fraction from Melia azedarach L. leaf aqueous extract restrains Herpes simplex virus type 1 propagation (2002) Phytother. Res., 16, pp. 348-352 
504 |a Wachsman, M., Castilla, V., Coto, C., Inhibition of foot and mouth disease virus (FMDV) uncoating by a plant-derived peptide isolated from Melia azedarach L. leaves (1998) Arch. Virol., 143, pp. 581-590 
504 |a Castilla, V., Barquero, A., Mersich, S., Coto, C., In vitro anti-Junín virus activity of a peptide isolated from Melia azedarach L. leaves (1998) Int. J. Antimicrob. Agents, 10, pp. 67-75 
504 |a Nicola, A., Straus, S., Cellular and viral requirements for rapid endocytic entry of herpes simplex virus (2004) J. Virol., 78, pp. 7508-7517 
504 |a Leuzinger, H., Ziegler, U., Schraner, E., Fraefel, C., Glauser, D., Heid, I., Ackermann, M., Wild, P., Herpes simplex virus 1 envelopment follows two diverse pathways (2005) J. Virol., 79, pp. 13047-13059 
504 |a Ludwig, S., Planz, O., Pleschka, S., Wolff, T., Influenza-virus-induced signaling cascades: targets for antiviral therapy? (2003) Trends Mol. Med., 9, pp. 46-52 
504 |a Santoro, M., Rossi, A., Amici, C., NF-kappaB and virus infection: who controls whom (2003) EMBO J., 22, pp. 2552-2560 
504 |a Amici, C., Belardo, G., Rossi, A., Santoro, M., Activation of I kappa b kinase by herpes simplex virus type 1. A novel target for anti-herpetic therapy (2001) J. Biol. Chem., 276, pp. 28759-28766 
504 |a Bremner, P., Heinrich, M., Natural products as targeted modulators of the nuclear factor-kappaB pathway (2002) J. Pharm. Pharmacol., 54, pp. 453-472 
520 3 |a We have reported the isolation of the tetranortriterpenoid 1-cinnamoyl-3,11-dihydroxymeliacarpin (CDM) from partially purified leaf extracts of Melia azedarach L. (MA) that reduced both, vesicular stomatitis virus (VSV) and Herpes simplex virus type 1 (HSV-1) multiplication. CDM blocks VSV entry and the intracellular transport of VSV-G protein, confining it to the Golgi apparatus, by pre- or post-treatment, respectively. Here, we report that HSV-1 glycoproteins were also confined to the Golgi apparatus independently of the nature of the host cell. Considering that MA could be acting as an immunomodulator preventing the development of herpetic stromal keratitis in mice, we also examined an eventual effect of CDM on NF-κB signaling pathway. CDM is able to impede NF-κB activation in HSV-1-infected conjunctival cells and leads to the accumulation of p65 NF-κB subunit in the cytoplasm of uninfected treated Vero cells. In conclusion, CDM is a pleiotropic agent that not only inhibits the multiplication of DNA and RNA viruses by the same mechanism of action but also modulates the NF-κB signaling pathway. © 2006 Elsevier Inc. All rights reserved.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires, UBA X-046 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 12343 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP 6033/05 
536 |a Detalles de la financiación: The authors thank Isabel Paz and Guillermo Assad Ferek for their technical assistance, and Roux-Ocefa laboratory for the liophilization of leaf extracts. This work was supported by grants from the University of Buenos Aires (UBA X-046), Agencia Nacional de Promoción Científica y Técnica (ANPCyT) (PICT 12343), and CONICET (PIP 6033/05). 
593 |a Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Pabellon II, Piso 4to., Ciudad Univ., C1428BGA Buenos Aires, Argentina 
690 1 0 |a 1-CINNAMOYL-3,11-DIHYDROXYMELIACARPIN 
690 1 0 |a ANTIINFLAMMATORY 
690 1 0 |a HERPES SIMPLEX VIRUS TYPE 1 
690 1 0 |a MELIA AZEDARACH L. 
690 1 0 |a NATURAL ANTIVIRAL 
690 1 0 |a NF-ΚB 
690 1 0 |a TRITERPENOIDS 
690 1 0 |a 1 CINNAMOYL 3,11 DIHYDROXYMELIACARPIN 
690 1 0 |a ANTIVIRUS AGENT 
690 1 0 |a TERPENOID DERIVATIVE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a 1 CINNAMOYL 3,11 DIHYDROXYMELIACARPIN 
690 1 0 |a 1-CINNAMOYL-3,11-DIHYDROXYMELIACARPIN 
690 1 0 |a ANTIVIRUS AGENT 
690 1 0 |a IMMUNOGLOBULIN ENHANCER BINDING PROTEIN 
690 1 0 |a LIMONOID 
690 1 0 |a ANIMAL CELL 
690 1 0 |a ARTICLE 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a DNA REPLICATION 
690 1 0 |a DNA VIRUS 
690 1 0 |a GOLGI COMPLEX 
690 1 0 |a HERPES SIMPLEX VIRUS 
690 1 0 |a HOST CELL 
690 1 0 |a IMMUNOMODULATION 
690 1 0 |a MEMBRANE TRANSPORT 
690 1 0 |a NONHUMAN 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a PURIFICATION 
690 1 0 |a RNA REPLICATION 
690 1 0 |a RNA VIRUS 
690 1 0 |a VESICULAR STOMATITIS VIRUS 
690 1 0 |a VIROGENESIS 
690 1 0 |a ANIMAL 
690 1 0 |a CELL LINE 
690 1 0 |a CERCOPITHECUS 
690 1 0 |a CONJUNCTIVA 
690 1 0 |a DOSE RESPONSE 
690 1 0 |a DRUG EFFECT 
690 1 0 |a GROWTH, DEVELOPMENT AND AGING 
690 1 0 |a HERPES SIMPLEX VIRUS 1 
690 1 0 |a HUMAN 
690 1 0 |a METABOLISM 
690 1 0 |a PHYSIOLOGY 
690 1 0 |a VERO CELL 
690 1 0 |a VIROLOGY 
690 1 0 |a VIRUS REPLICATION 
690 1 0 |a HUMAN HERPESVIRUS 1 
690 1 0 |a MELIA AZEDARACH 
690 1 0 |a RNA VIRUSES 
690 1 0 |a VESICULAR STOMATITIS VIRUS 
690 1 0 |a ANIMALS 
690 1 0 |a ANTIVIRAL AGENTS 
690 1 0 |a CELL LINE 
690 1 0 |a CERCOPITHECUS AETHIOPS 
690 1 0 |a CONJUNCTIVA 
690 1 0 |a DOSE-RESPONSE RELATIONSHIP, DRUG 
690 1 0 |a HERPESVIRUS 1, HUMAN 
690 1 0 |a HUMANS 
690 1 0 |a LIMONINS 
690 1 0 |a NF-KAPPA B 
690 1 0 |a VERO CELLS 
690 1 0 |a VIRUS REPLICATION 
700 1 |a Michelini, F.M. 
700 1 |a Alché, L.E. 
773 0 |d 2006  |g v. 344  |h pp. 955-962  |k n. 3  |p Biochem. Biophys. Res. Commun.  |x 0006291X  |w (AR-BaUEN)CENRE-905  |t Biochemical and Biophysical Research Communications 
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