Anti-HIV activity of dibenzylbutyrolactone-type lignans from Phenax species endemic in Costa Rica

Journal of Pharmacy and Pharmacology

Volumn 57, Issue 9, 2005, Pages 1109-1115

  Piccinelli, A L ^a   Mahmood, N ^b   Mora, G ^c   Poveda, L ^d   De Simone, F ^a   Rastrelli, L ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b ST GEORGE'S UNIVERSITY OF LONDON   (United Kingdom)

^c UNIVERSIDAD DE COSTA RICA   (Costa Rica)

^d UNIVERSIDAD NACIONAL   (Costa Rica)

Author keywords

[No Author keywords available]

Indexed keywords

DIBENYLBUTYROLACTONE; ISOVITEXIN 7; LIGNAN DERIVATIVE; PHENAX ANGUSTIFOLIUS EXTRACT; PHENAXOLACTONE 1; PHENAXOLACTONE 2; PHENAXOLACTONE 3; PHENAXOLACTONE 4; PHENAXOLACTONE 5; PLANT EXTRACT; UNCLASSIFIED DRUG; VITEXIN 6;

ANTIVIRAL ACTIVITY; ARTICLE; COSTA RICA; DRUG ISOLATION; DRUG STRUCTURE; HUMAN IMMUNODEFICIENCY VIRUS 1; MASS SPECTROMETRY; MEDICINAL PLANT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENAX ANGUSTIFOLIUS; PHENAX RUGOSUS; PLANT LEAF; SPECIES ENDEMICITY; STRUCTURE ANALYSIS;

4-BUTYROLACTONE; ANTI-HIV AGENTS; APIGENIN; CHEMISTRY, PHARMACEUTICAL; COSTA RICA; ETHANOL; GEOGRAPHY; LACTONES; LIGNANS; PLANT EXTRACTS; PLANT LEAVES; STRUCTURE-ACTIVITY RELATIONSHIP; TECHNOLOGY, PHARMACEUTICAL; URTICACEAE;

EID: 25844486484     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.57.9.0006     Document Type: Article

References (24)

1. Abdel-Kader, M. S., Wisse, J., Evans, R., Van der Werff, H., Kingston, D. G. (1997) Bioactive iridoids and a new lignan from Allamanda cathartica and Himatanthus fallax from the Suriname rainforest. J. Nat. Prod. 60: 1294-1297
2. Agrawal, P. K. (1989) In: Carbon-13 NMR of flavonoids. Elsevier, London
3. Burger, W. (1997) Flora Costaricensis. FIELDIANA Botany 40: 241-246
4. Charlton, J. L. (1998) Antiviral activity of lignans. J. Nat. Prod. 61: 1447-1451
5. Dalgleish, A. G., Beverley, P. C., Clapham, P. R., Crawford, D. H., Greaves, M. F., Weiss, R. A. (1984) The CD4 (T4) antigen is an essential component of the receptor for the AIDS retrovirus. Nature 312: 763-767
6. 1H NMR spectra by selective excitation of experimental subspectra. J. Am. Chem. Soc. 107: 7198-7199
7. Eich, E., Pertz, H., Kaloga, M., Schulz, J., Fesen, M. R., Mazumder, A., Pommier, Y. (1996) (-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase. J. Med. Chem. 39: 86-95
8. Estevez-Reyes, R., Estevez-Braun, A., Gonzales, A. G. (1993) New lignan butenolides from Bupleurum salicifoliu. J. Nat. Prod. 56: 1177-1181
9. Gnabre, J. N., Brady, J. N., Clanton, D. J., Ito, Y., Dittmer, J., Bates, R. B., Huang, R. C. (1995) Inhibition of human immunodeficiency virus type 1 transcription and replication by DNA sequence-selective plant lignans. Proc. Natl. Acad. Sci. USA 92: 11239-11243
10. Gonzales, A. G., Estevez-Reyes, R., Mato, C., Estevez-Braun, A. M. (1990) Three lignans from Bupleurum salicifolium. Phytochemistry 29: 1981-1983
11. Hammonds, T. R., Denyer, S. P., Jackson, D. E., Irving, W. L. (1996) Studies to show that with podophyllotoxin the early replicative stages of herpes simplex virus type 1 depend upon functional cytoplasmic microtubules. J. Med. Microb. 45: 167-172
12. Harborne, J. B. (1994) In: The flavonoids: advances in research since 1986. Chapman & Hall, New York
13. Hu, C. Q., Chen, K., Shi, Q., Kilkuskie, R. E., Cheng, Y. C., Lee, K. H. (1994) Anti-aids agents, 10. Acacetin-7-O-β-D-galactopyranoside, an anti-HIV principle from Chrysanthemum morifolium and a structure-activity correlation with some related flavonoids. J. Nat. Prod. 57: 42-51
14. Inagaki, I., Hisada, S., Nishibe, S. (1972) Lignans of Trachelospermum asiaticum var intermedium. I. Isolation and structures of arctiin, matairesinoside, and tracheloside. Chem. Pharm. Bull. 20: 2710-2718
15. LaBranche, C. C., Galasso, G., Moore, J. P., Bolognesi, D. P., Hirsch, M. S. (2001) HIV fusion and its inhibition. Antiviral Res. 50: 95-115
16. Li-Ming, Y., Shwu-Jiuan, L., Tsang-Hsiung, Y., Kuo-Hsiung, L. (1996) Synthesis and anti-HIV activity of dibenzylbutyrolactone lignans. Bioorg. Med. Chem. Lett. 6: 941-944
17. Mahmood, N., Hay, A. J. (1992) An ELISA utilizing immobilized snowdrop lectin GNA for the detection of envelope glycoproteins of HIV and SIV. J. Immunol. Methods 151: 9-13
18. Mahmood, N., Pizza, C., Aquino, R., De Tommasi, N., Piacente, S., Colman, S., Burke, A., Hay, A. J. (1993) Inhibition of HIV infection by flavonoids. Antiviral Res. 22: 189-199
19. Nishibe, S., Chiba, M., Sakushima, A., Hisada, S., Yamanouchi, S., Takido, M., Sankawa, U., Sakakibara, A. (1980) Introduction of an alcoholic hydroxyl group into 2,3-dibenzylbutyrolactone lignans with oxidizing agents and carbon-13 nuclear magnetic resonance spectra of the oxidation products. Chem. Pharm. Bull. 28: 850-860
20. Rastrelli, L., Mora, G., Brenes, J. C., De Simone, F., Aquino, R. (1998) In: The 7th annual meeting of the ItaloLatinAmerican Society of Ethnomedicine. Silae (ed.), Salerno, p. 28
21. Rastrelli, L., De Simone, F., Mora, G., Poveda, L. J., Aquino, R. (2001) Phenolic constituents of Phenax angustifolius. J. Nat. Prod. 64: 79-81
22. Weislow, O. S., Kiser, R., Fine, D. L., Bader, J., Shoemaker, R. H., Boyd, M. R. (1989) New soluble-formazan assay for HIV-1 cytopathic effects: application to high-flux screening of synthetic and natural products for AIDS-antiviral activity. J. Natl. Cancer Inst. 81: 577-586
23. Wyatt, R., Kwong, P. D., Desjardins, E., Sweet, R. W., Robinson, J., Hendrickson, W. A., Sodroski, J. G. (1988) The antigenic structure of the HIV gp120 envelope glycoprotein. Nature 393: 705-711
24. Yachou, A., Sekaly, R. P. (1999) Binding of soluble recombinant HIV envelope glycoprotein, rgp120, induces conformational changes in the cellular membrane-anchored CD4 molecule. Biochem. Biophys. Res. Commun. 265: 428-433