Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol α-pyrone from Helichrysum italicum ssp. microphyllum

Journal of Natural Products

Volumn 70, Issue 4, 2007, Pages 608-612

  Appendino, Giovanni ^a,b   Ottino, Michela ^a,b   Marquez, Nieves ^e   Bianchi, Federica ^a,b   Giana, Anna ^a,b   Ballero, Mauro ^b   Sterner, Olov ^c   Fiebich, Bernd L ^d   Munoz, Eduardo ^e  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^b Consorzio per lo Studio dei Metaboliti Secondari ^*  (Italy)

^c LUND UNIVERSITY   (Sweden)

^d UNIVERSITY OF FREIBURG   (Germany)

^e Universidad de Cordoba   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIHYDROXYPHENYL; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIBIOTIC AGENT; ANTIINFLAMMATORY AGENT; ARENARIN; BENZENE DERIVATIVE; CYTOKINE; HELICHRYSUM EXTRACT; HOMOARENOL; I KAPPA B; PHLOROGLUCINOL ALPHA PYRONE ARZANOL; PHLOROGLUCINOL DERIVATIVE; PYRONE DERIVATIVE; TERPENE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; FRAGMENTATION REACTION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROXYLATION; IN VITRO STUDY; MONOCYTE; T LYMPHOCYTE; VIRUS REPLICATION;

ANTI-HIV AGENTS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DINOPROSTONE; HELICHRYSUM; HIV-1; HUMANS; INTERLEUKIN-1BETA; INTERLEUKIN-6; LIPOPOLYSACCHARIDES; MOLECULAR STRUCTURE; MONOCYTES; PHLOROGLUCINOL; PLANTS, MEDICINAL; PYRONES; T-LYMPHOCYTES; TUMOR NECROSIS FACTOR-ALPHA;

HELICHRYSUM ITALICUM; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 34248998455     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np060581r     Document Type: Article

References (39)

1. Pignatti, S. Flora d'Italia; Edagricole: Bologna, 1982; Vol. 3, p 42.
2. Heliochrysum ... duritias and inflammations discutit, ambustis cum melle inponitur. Contra ... lumborum vitia bibitur (Helichrysum heals hardenings and inflammation, and mixed with honey soothes burnings. It is used as a potion against rheumatisms): Pliny the Elder. Naturalis Historia, XXI; pp 168-169.
3. For a review, see: Ballero, M.; Maxia, A. Erboristeria Domani 2006, 300, 52-56.
4. (a) Santini, L. Considerazioni sugli Effetti Terapeutici dell'Elicriso; Salvetti: Castelnuovo, 1948.
5. (b) Santini, L. Atti Soc. Lomb. Sci. Med. Biol. 1949, 5, 18.
6. A synopsis of Santini's studies on Helicrysum was recently published (Santini, L. Erboristeria Domani 2006, 300, 65-71).
7. Most investigations on the chemistry of plants from the genus Helichrysum were carried out by Bohlmann and Jakupovic. In an impressive publication, 26 phloroglucinols, nine diterpenoids, one sesquiterpene, and one pyrone were described, besides known compounds, from 11 South African species (Jakupovic, J.; Kuhnke, J.; Schuster, A.; Metwally, M. A.; Bohlmann, F. Phytochemistry 1986, 25, 1133-1142).
8. (a) Araceli, S.; Recio, M. C.; Giner, R. M.; Máňez, S.; Rios, J. L. J. Nat. Prod. 2001, 64, 1360-1362.
9. (b) Araceli, S.; Recio, M. C.; Schinella, L. G. R.; Máňez, G.; Giner, R. M.; Rios, J.-L. J. Pharmacol. 2003, 460, 219-226.
10. (c) Sala, A.; Recio, M. C.; Schinella, G.; Máňez.; Giner, R. M.; Cereda-Nicolas, M.; Rios, J.-L. Eur. J. Pharmacol. 2003, 461, 53-61.
11. Hume, D. A.; Fairlie, D. P. Curr. Med. Chem. 2005, 25, 2925-2929.
12. (a) Karin, M. Nature 2006, 414, 431-436.
13. (b) Karin, M.; Ben-Neriah, Y. Annu. Rev. Immunol. 2000, 18, 621-663.
14. 6
15. (a) Singh, I. P.; Bharate, S. B. Nat. Prod. Rep. 2006, 23, 558-591.
16. (b) Ciochina, R.; Grossman, R. B. Chem. Rev. 2006, 106, 3963-3986.
17. Vrkoč, J.; Dolejš, L.; Sedmera, P.; Vaší čková, S.; Šorm, F. Tetrahedron Lett. 1971, 247-250.
18. Bohlmann, F.; Zdero, C. Phytochemistry 1980, 19, 153-155.
19. For a short biography of F. Šorm, see: http://www.garfield. library.upenn.edu/essays/v15p051y1992-93.pdf
20. Appendino, G.; Cravotto, G.; Nano, G. M.; Palmisano, G.; Annunziata, R. Helv. Chim. Acta 1993, 76, 1194-1201.
21. (a) Verona, L.; Lovaglio, E.; Sterner, O.; Appendino, G.; Bombardelli, E. Eur. J. Org. Chem. 2004, 1193-1197.
22. (b) Verotta, L.; Lovaglio, E.; Sterner, O.; Appendino, G.; Bombardelli, E. J. Org. Chem. 2004, 69, 7869-7864.
23. 12 we were unable to reproduce this reaction. In a typical experiment, treatment of the tetraacetate of 1b with 1 M KOH in MeOH at room temperature led to the complete consumption of the starting material in less than 6 h, affording a complex mixture from which no pure product could be characterized.
24. Rashba, O. Y. Acad. Nauk. Ukr. R.S.P. 1957, 19, 25-28; Chem. Abstr. 1958, 51, 87680. Arenarin was successfully employed as an eye antibiotic.
25. Atropisomerism was detected in flavan-acylphloroglucinol dimers around the bond connecting these two moieties (Sawadjoon, S.; Kittakoop, P.; Kirtikara, K.; Vichai, V.; Tanticharoen, M.; Thebtaranonth, Y. J. Org. Chem. 2002, 67, 5470-5475).
26. Appendino, G.; Bianchi, F.; Minassi, A.; Sterner, O.; Ballero, M.; Gibbons, S. J. Nat. Prod. 2002, 65, 334-338.
27. Hänsel, R.; Cybulski, E.-M.; Çubukçu, B.; Meriçli, A. H.; Bohlmann, F.; and Zdero, C. Phytochemistry 1980, 19, 639-644.
28. (a) Tira, S.; Di Modica, G.; Casinovi, C. G.; Galeffi, C.; Pela, A. Tetrahedron Lett. 1967, 143-148.
29. (b) Manritto, P.; Monti, D.; Colombo, E. Phytochemistry 1972, 6, 2122-2124.
30. Opiz, L.; Hänsel, R. Tetrahedron Lett. 1970, 3369-3370.
31. The tremetone bitalin A (12-hydroxytremetone, 9a) had already been isolated from H. italicum (Zapesochnaya, G. G.; Dzyadevich, T. V.; Karasartov, B. S. Khim Prir. Soedin. 1990, 409-410; Chem. Abstr. 1991, 114, 98154).
32. Tremetone is the (in)famous white snakeroot (Eupatorium rugosum) toxicant excreted in cows' milk and responsible for the so-called "milk sickness" of humans (Panter, K. E.; James, L. F. J. Anim. Sci. 1990, 68, 892-904).
33. Some tremetones show anti-inflammatory activity (Favier, L.; Tonn, C.; Guerriero, E.; Rotell, A.; Pelzer, L. Planta Med. 1998, 64, 657-659).
34. (a) Satta, M.; Tuberoso, C. I. G.; Angioni, A.; Pirisi, F. M.; Cabras, P. J. Essent. Oil. Res. 1999, 11, 711-715.
35. (b) Angioni, A.; Barra, A.; Arlorio, M.; Coisson, J. D.; Russo, M. T.; Pirisi, F. M.; Satta, M.; Cabras, P. J. Agric. Food Chem. 2003, 51, 1030-1034.
36. Behr, D.; Wahlberg, I.; Nishida, T.; Enzell, C. R. Acta Chem. Scand. B 1978, 32, 228-234.
37. Marquez, N.; Sancho, R.; Macho, A.; Calzado, M: A.; Fiebich, B. L.; Muñoz, E. J. Pharmacol. Exp Ther. 2004, 308, 993-1001.
38. Canki, M.; Thai, J. N.; Chao, W.; Ghorpade, A.; Potash, M. J.; Volsky, D. J. J. Virol. 2001, 75, 7925-7933.
39. Sancho, R.; Medarde, M.; Sanchez-Palomino, S.; Madrigal, B. M.; Alcami, J.; Muñoz, E.; San, Feliciano, A. Bioorg. Med. Chem. Lett. 2004, 14, 4483-4486.