Hypericum in infection: Identification of anti-viral and anti-inflammatory constituents

Pharmaceutical Biology

Volumn 47, Issue 8, 2009, Pages 774-782

  Birt, Diane F ^a   Widrlechner, Mark P ^a,b   Hammer, Kimberly D P ^a   Hillwig, Matthew L ^a   Wei, Jingqiang ^a   Kraus, George A ^a   Murphy, Patricia A ^a   McCoy, Joe Ann ^a,b,e   Wurtele, Eve S ^a   Neighbors, Jeffrey D ^a,c   Wiemer, David F ^a,c   Maury, Wendy J ^a,d   Price, Jason P ^a,d  

^a IOWA STATE UNIVERSITY   (United States)

^b AGRICULTURAL RESEARCH SERVICE   (United States)

^c E11 SSH   (United States)

^d UNIVERSITY OF IOWA   (United States)

^e North Carolina Arboretum   (United States)

Author keywords

Anti inflammatory; Anti viral; Flavonoids; Hypericum; Infection; Phloroglucinols

Indexed keywords

AMENTOFLAVONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIINFLAMMATORY AGENT; APIGENIN; CHLOROGENIC ACID; FLAVONE DERIVATIVE; HYPERFORIN; HYPERICIN; HYPERICUM PERFORATUM EXTRACT; HYPEROLACTONE C; ISOQUERCITRIN; LACTONE DERIVATIVE; PHLOROGLUCINOL DERIVATIVE; PSEUDOHYPERICIN; QUERCETIN; RUTOSIDE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ANTIVIRAL ACTIVITY; BIOASSAY; CONFERENCE PAPER; DRUG ACTIVITY; DRUG ISOLATION; DRUG MECHANISM; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HYPERICUM; INFECTION; NONHUMAN; PHYTOCHEMISTRY;

CLUSIACEAE; HUMAN IMMUNODEFICIENCY VIRUS 1; HYPERICUM; HYPERICUM PERFORATUM;

EID: 77149125614     PISSN: 13880209     EISSN: 17445116     Source Type: Journal    
DOI: 10.1080/13880200902988645     Document Type: Conference Paper

References (41)

1. Agostinis P, Vandenbogaerde A, Donella-Deana A, Pinna LA, Lee KT, Goris J, Merlevede W, Vandenheede JR, De Witte P (1995): Photosensitized inhibition of growth factor-regulated protein kinases by hypericin. Biochem Pharmacol 49: 1615-1622.
2. Aramaki Y, Chiba K, Tada M (1995): Spiro-lactones, hyperolactone A-D from Hypericum chinense. Phytochemistry 38: 1419-1421.
3. Birt DF, Widrlechner MP, LaLone CA, Wu L, Bae J, Solco AKS, Kraus GA, Murphy PA, Wurtele ES, Leng Q, Hebert SC, Maury WJ, Price JP (2008): Echinacea in infection. Am J Clin Nutr 87(Suppl.): 488S-492S.
4. Bombardelli E, Morazzoni P (1995): Hypericum perforatum. Fitoterapia 66: 43-68.
5. Brenner DM, Widrlechner MP (1998): Amaranthus seed regeneration in plastic tents in greenhouses. Plant Genet Resour Newsl 116: 1-4.
6. Carpenter S, Fehr MJ, Kraus GA, Petrich JW (1994): Chemiluminescent activation of the antiviral activity of hypericin: a molecular flash-light. Proc Natl Acad Sci USA 91: 12273-12277.
7. De Witte P, Agostinis P, Van Lint J, Merlevede W, Vandenheede JR (1993): Inhibition of epidermal growth factor receptor tyro-sine kinase activity by hypericin. Biochem Pharmacol 46: 1929-1936.
8. Degar S, Prince AM, Pascual D, Lavie G, Levin B, Mazur Y, Lavie D, Ehrlich LS, Carter C, Meruelo D (1992): Inactivation of the human immunodefficiency virus by hypericin: evidence for photochemical alterations of p24 and a block in uncoating. AIDS Res Hum Retrovir 8: 1929-1936.
9. Farnet CM, Wang B, Hansen M, Lipford JR, Zalkow L, Robinson WE Jr, Siegel J, Bushman F (1998): Human immunodeficiency virus type 1 cDNA integration: new aromatic hydroxylated inhibitors and studies of the inhibition mechanism. Antimicrob Agents Chemother 42: 2245-2253.
10. Ganzera M, Zhao J, Khan IA (2002): Hypericum perforatum - Chemical profiling and quantitative results of St. John's wort products by an improved high-performance liquid chromatography method. J Pharmaco Sci 91: 623-630.
11. Gaudin M, Simonnet X, Debrunner N (2003): Colletotrichum gloeosporioides as the cause of St. John's wort (Hypericum perforatum) dieback in Switzerland and breeding for a tolerant variety. In: Ernst E, ed., Hypericum: The Genus Hypericum. London, Taylor & Francis, pp. 23-42.
12. Gibbons S, Moser E, Hausmann S, Stavri M, Smith E, Clennett C (2005): An anti-staphylococcal acylphloroglucinol from Hypericum foliosum. Phytochemistry 66: 1472-1475.
13. 2 production by anti-inflammatory Hypericum perforatum extracts and constituents in RAW264.7 mouse macrophage cells. J Agric Food Chem 55: 7323-7331.
14. Hammer KDP, Hillwig ML, Neighbors JD, Sim YJ, Kohut ML, Wiemer DF, Wurtele ES, Birt DF (2008): Pseudohypericin is necessary for the light-activated inhibition of prostaglandin E2 by Hypericum perforatum. Phytochemistry 69: 2354-2362.
15. Hildebrand PD, Jensen KIN (1991): Potential for the biological control of St. John's-wort (Hypericum perforatum) with an endemic strain of Colletotrichum gloeosporioides. Can J Plant Pathol 13: 60-70.
16. Hudson JB, Lopez-Bazzocchi I, Towers GH (1991): Antiviral activities of hypericin. Antiviral Res 15: 101-112.
17. Ichinari D, Ueki T, Yoshihara K, Kinoshita T (1997): First total synthesis of (β)-hyperolactone A. Chem Commun (Camb) 18: 1743-1744.
18. Jacobson JM, Feinman L, Liebes L, Ostrow N, Koslowski V, Tobia A, Cabana BE, Lee D, Spritzler J, Prince AM (2001): Pharmacokinetics, safety, and antiviral effects of hypericin, a derivative of St. John's Wort plant, in patients with chronic hepatitis C virus infection. Antimicrob Agents Chemother 45: 517-524.
19. Kartnig T, Goebel I, Heydel B (1996): Production of hypericin, pseudohypericin and flavonoids in cell cultures of various Hypericum species and their chemotypes. Planta Med 62: 51-53.
20. Kraus GA, Jeon I (2006): Use of allylic strain to enforce stereochemistry. A direct synthesis of calamenenes from Hypericum elodeoides. Org Lett 8: 5315-5316.
21. Kraus GA, Pratt D, Tossberg J, Carpenter S (1990): Antiretroviral activity of synthetic hypericin and related analogs. Biochem Biophys Res Commun 172: 149-153.
22. Kraus GA, Wei J (2004): A direct synthesis of hyperolactone C. J Nat Prod 67: 1039-1040.
23. Kuhn D (1995): Hypericin: An answer for safer blood? Common Factor 10: 36.
24. Laurent D, Baumann F, Benoit AG, Mortelecqe A, Nitatpattana N, Desvignes I, Debitus C, Laille M, Gonzalez JP, Chungue E (2005): Structure-activity relationships of dengue antiviral polycyclic quinines. Southeast Asian J Trop Med Public Health 36: 901-905.
25. Lavie G, Mazur Y, Lavie D, Prince AM, Pascual D, Liebes L, Levin B, Meruelo D (1995): Hypericin as an inactivator of infectious viruses in blood components. Transfusion 35: 392-400.
26. Lopez-Bazzocchi I, Hudson JB, Towers GH (1991): Antiviral activity of the photoactive plant pigment hypericin. Photochem Photobiol 54: 95-98.
27. Marais JPJ, Ferreira D, Slade D (2005): Stereoselective synthesis of monomeric flavonoids. Phytochemistry 66: 2145-2176.
28. Mathela DK, Mathela CS, Dev V (1984): Volatile constituents of Hypericum elodeoides Chois. J Indian Chem Soc 61: 792-793.
29. McCoy J (2007): Utilizing the national plant germplasm system for medicinal plant research. In: Janick J, Whipkey A, eds., Issues in New Crops and New Uses. Alexandria, VA, ASHS Press, pp. 258-260.
30. Meruelo D, Lavie G, Lavie D (1988): Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: Aromatic polycyclic diones hypericin and pseudohypericin. Proc Natl Acad Sci USA 85: 5230-5234.
31. Middleton E Jr, Kandaswami C, Theoharides TC (2000): The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol Rev 52: 673-751.
32. Naesens L, Bonnafous P, Agut H, De Clercq E (2006): Antiviral activity of diverse classes of broad-acting agents and natural compounds in HHV-6-infected lymphoblasts. J Clin Virol 37 (Suppl. 1): S69-S75.
33. Park J, English DS, Wannemuehler Y, Carpenter S, Petrich JW (1998): The role of oxygen in the antiviral activity of hypericin and hypocrellin. Photochem Photobiol 68: 593-597.
34. Percifield RJ, Hawkins JS, McCoy J, Widrlechner MP, Wendel JF (2007): Genetic diversity in Hypericum and AFLP markers for species-specific identification of H. perforatum L. Planta Med 73: 1614-1621.
35. Reed-Inderbitzin E, Maury W (2003): Cellular specificity of HIV-1 replication can be controlled by LTR sequences. Virology 314: 680-695.
36. Robson NKB (2003): Hypericum botany. In: Ernst E, ed., Hypericum: The Genus Hypericum. London, Taylor & Francis, pp. 1-22.
37. US Department of Agriculture (2007): Germplasm Resources Information Network Database. Accessed on the Internet at http://www.ars-grin.gov/npgs, on 27 August 2007.
38. Viola H, Wasowski C, Levi de Stein M, Wolfman C, Silveira R, Dajas F, Medina JH, Paladini AC (1995): Apigenin, a component of Matricaria recutita flowers, is a central benzodiazepine receptors-ligand with anxiolytic effects. Planta Med 61: 213-216.
39. Vyas GN (1995): Inactivation and removal of blood-borne viruses. Transfusion 35: 367-370.
40. Widrlechner MP, Abel CA, Wilson RL (1997): Ornamental seed production in field cages with insect pollination. Comb Proc IPPS 46: 512-516.
41. Widrlechner MP, McKeown KA (2002): Assembling and characterizing a comprehensive Echinacea germplasm collection. In: Janick J, Whipkey A, eds., Trends in New Crops and New Uses. Alexandria, VA, ASHS Press, pp. 506-508.