Identification of light-independent inhibition of human immunodeficiency virus-1 infection through bioguided fractionation of Hypericum perforatum

Virology Journal

Volumn 6, Issue , 2009, Pages

  Maury, Wendy ^a   Price, Jason P ^a   Brindley, Melinda A ^a   Oh, Choonseok ^a   Neighbors, Jeffrey D ^b   Wiemer, David F ^b   Wills, Nickolas ^c   Carpenter, Susan ^c   Hauck, Cathy ^c   Murphy, Patricia ^c   Widrlechner, Mark P ^c,d   Delate, Kathleen ^c   Kumar, Ganesh ^c   Kraus, George A ^c   Rizshsky, Ludmila ^c   Nikolau, Basil ^c  

^a UNIVERSITY OF IOWA   (United States)

^b University of Iowa   (United States)

^c IOWA STATE UNIVERSITY   (United States)

^d AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYDODECANOIC ACID; 3 HYDROXYMYRISTIC ACID; FATTY ACID DERIVATIVE; HYPERICUM PERFORATUM EXTRACT; LAURIC ACID DERIVATIVE; MYRISTIC ACID DERIVATIVE; UNCLASSIFIED DRUG; 3-HYDROXY-LAURIC ACID; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; BETA-HYDROXYMYRISTIC ACID; PLANT EXTRACT;

ANTIVIRAL ACTIVITY; ARTICLE; BIOASSAY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; FRACTIONATION; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; HYPERICUM PERFORATUM; LIGHT; MASS FRAGMENTOGRAPHY; NONHUMAN; PLANT GROWTH; SEEDLING; VIRUS INFECTIVITY; VIRUS INHIBITION; CHEMISTRY; DRUG EFFECT; HELA CELL; HUMAN; HYPERICUM; ISOLATION AND PURIFICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1; HYPERICUM PERFORATUM;

ANTI-HIV AGENTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HELA CELLS; HIV-1; HUMANS; HYPERICUM; LAURIC ACIDS; MYRISTIC ACIDS; PLANT EXTRACTS;

EID: 68749099751     PISSN: None     EISSN: 1743422X     Source Type: Journal    
DOI: 10.1186/1743-422X-6-101     Document Type: Article

References (44)

1. St. John's wort: role of active compounds for its mechanism of action and efficacy. V Butterweck M Schmidt, Wien Med Wochenschr 2007 157 356 361 10.1007/s10354-007-0440-8 17704987 (Pubitemid 47356264)
2. Characterization of apoptosis induced by photodynamic treatment with hypericin in A431 human epidermoid carcinoma cells. J Berlanda T Kiesslich CB Oberdanner FJ Obermair B Krammer K Plaetzer, J Environ Pathol Toxicol Oncol 2006 25 173 188 16566716
3. Hyperforin down-regulates effector function of activated T lymphocytes and shows efficacy against Th1-triggered CNS inflammatory-demyelinating disease. A Cabrelle I Dell'Aica L Melchiori S Carraro E Brunetta R Niero E Scquizzato G D'Intino L Calza S Garbisa C Agostini, J Leukoc Biol 2008 83 212 219 10.1189/jlb.0707469 17947392
4. Matrix proteases, green tea, and St. John's wort: biomedical research catches up with folk medicine. I Dell'Aica R Caniato S Biggin S Garbisa, Clin Chim Acta 2007 381 69 77 10.1016/j.cca.2007.02.022 17382921 (Pubitemid 46719133)
5. Hyperforin blocks neutrophil activation of matrix metalloproteinase-9, motility and recruitment, and restrains inflammation-triggered angiogenesis and lung fibrosis. I Dell'Aica R Niero F Piazza A Cabrelle L Sartor C Colalto E Brunetta G Lorusso R Benelli A Albini F Calabrese C Agostini S Garbisa, J Pharmacol Exp Ther 2007 321 492 500 10.1124/jpet.106.116459 17289834 (Pubitemid 46624507)
6. Inhibition of prostaglandin E(2) production by anti-inflammatory hypericum perforatum extracts and constituents in RAW264.7 Mouse Macrophage Cells. KD Hammer ML Hillwig AK Solco PM Dixon K Delate PA Murphy ES Wurtele DF Birt, J Agric Food Chem 2007 55 7323 7331 17696442 10.1021/jf0710074 (Pubitemid 47492285)
7. Monograph. Hypericum perforatum. Altern Med Rev 2004 9 318 325 15387723
8. Anthraquinones as a new class of antiviral agents against human immunodeficiency virus. RF Schinazi CK Chu JR Babu BJ Oswald V Saalmann DL Cannon BF Eriksson M Nasr, Antiviral Res 1990 13 265 272 10.1016/0166-3542(90) 90071-E 1697740 (Pubitemid 20185347)
9. Screening of in vitro antimicrobial and antioxidant activity of nine Hypericum species from the Balkans. N Radulovic' V Stankov-Jovanovic' G Stojanovic' A Melcerovic M Spiteller Y Asakawa, Food Chemistry 2007 103 15 21 10.1016/j.foodchem.2006.05.062 (Pubitemid 46290608)
10. St John's for depression, worts and all. JW Williams Jr T Holsinger, Bmj 2005 330 E350 351 10.1136/bmj.330.7500.E350 15891203
11. Hypericum perforatum: a 'modern' herbal antidepressant: pharmacokinetics of active ingredients. M Wurglics M Schubert-Zsilavecz, Clin Pharmacokinet 2006 45 449 468 10.2165/00003088-200645050-00002 16640452
12. Therapeutic agents with dramatic antiretroviral activity and little toxicity at effective doses: aromatic polycyclic diones hypericin and pseudohypericin. D Meruelo G Lavie D Lavie, Proc Natl Acad Sci USA 1988 85 5230 5234 2839837 10.1073/pnas.85.14.5230 (Pubitemid 18192941)
13. Virucidal activity of hypericin against enveloped and non-enveloped DNA and RNA viruses. J Tang JM Colacino SH Larsen W Spitzer, Antiviral Res 1990 13 313 325 10.1016/0166-3542(90)90015-Y 1699494 (Pubitemid 20223545)
14. Photosensitization is required for inactivation of equine infectious anemia virus by hypericin. S Carpenter GA Kraus, Photochem Photobiol 1991 53 169 174 10.1111/j.1751-1097.1991.tb03919.x 1707176
15. Antiviral activities of hypericin. JB Hudson I Lopez-Bazzocchi GH Towers, Antiviral Res 1991 15 101 112 10.1016/0166-3542(91)90028-P 1650164
16. Chemiluminescent activation of the antiviral activity of hypericin: a molecular flashlight. S Carpenter MJ Fehr GA Kraus JW Petrich, Proc Natl Acad Sci USA 1994 91 12273 12277 7991618 10.1073/pnas.91.25.12273 (Pubitemid 24368647)
17. Evaluation of the light-sensitive cytotoxicity of Hypericum perforatum extracts, fractions, and pure compounds. LA Schmitt Y Liu PA Murphy DF Birt, J Agric Food Chem 2006 54 2881 2890 16608204 10.1021/jf052344k
18. Mitochondria are a primary target of hypericin phototoxicity: synergy of intracellular calcium mobilisation in cell killing. TA Theodossiou A Noronha-Dutra JS Hothersall, Int J Biochem Cell Biol 2006 38 1946 1956 10.1016/j.biocel.2006.05.009 16814590 (Pubitemid 44425252)
19. Phase I studies of hypericin, the active compound in St. John's Wort, as an antiretroviral agent in HIV-infected adults. AIDS Clinical Trials Group Protocols 150 and 258. RM Gulick V McAuliffe J Holden-Wiltse C Crumpacker L Liebes DS Stein P Meehan S Hussey J Forcht FT Valentine, Ann Intern Med 1999 130 510 514 10075619
20. Agents for treating human immunodeficiency virus infection. EP Acosta CV Fletcher, Am J Hosp Pharm 1994 51 2251 2267 7801986
21. Hypericin as an inactivator of infectious viruses in blood components. G Lavie Y Mazur D Lavie AM Prince D Pascual L Liebes B Levin D Meruelo, Transfusion 1995 35 392 400 10.1046/j.1537-2995.1995.35595259149.x 7740610
22. Virucidal activity of pure singlet oxygen generated by thermolysis of a water-soluble naphthalene endoperoxide. A Dewilde C Pellieux S Hajjam P Wattre C Pierlot D Hober JM Aubry, J Photochem Photobiol B 1996 36 23 29 10.1016/S1011-1344(96)07323-X 8988609 (Pubitemid 27007310)
23. The lipophilic extract of Hypericum perforatum exerts significant cytotoxic activity against T24 and NBT-II urinary bladder tumor cells. D Skalkos NE Stavropoulos I Tsimaris E Gioti CD Stalikas UO Nseyo E Ioachim NJ Agnantis, Planta Med 2005 71 1030 1035 10.1055/s-2005-873127 16320204 (Pubitemid 41802871)
24. Reduction in hypericin-induced phototoxicity by Hypericum perforatum extracts and pure compounds. LA Schmitt Y Liu PA Murphy JW Petrich PM Dixon DF Birt, J Photochem Photobiol B 2006 85 118 130 16859921 10.1016/j.jphotobiol. 2006.06.001 (Pubitemid 44542577)
25. Seasonal variation in hypericin content of Hypericum perforatum L. (St. John's Wort). IA Southwell CA Bourke, Phytochemistry 2001 56 437 441 10.1016/S0031-9422(00)00411-8 11261576 (Pubitemid 32193089)
26. Regional differences in hypericin and pseudohypericin concentrations and five morphological traits among Hypericum perforatum plants in the northwestern United States. L Walker T Sivent TD Gibson N Vance, Can J Bot 2001 79 1248 10.1139/cjb-79-10-1248 (Pubitemid 33037709)
27. Quantification of bacterial lipopolysaccharides (endotoxin) by GC-MS determination of 3-hydroxy fatty acids. N Binding S Jaschinski S Werlich S Bletz U Witting, J Environ Monit 2004 6 65 70 10.1039/b309237b 14737472 (Pubitemid 38122123)
28. Histochemical evidence for lipid A (endotoxin) in eukaryote chloroplasts. MT Armstrong SM Theg N Braun N Wainwright RL Pardy PB Armstrong, Faseb J 2006 20 2145 2146 10.1096/fj.05-5484fje 16935939 (Pubitemid 44953881)
29. Innate immune reactions stimulated by a lipopolysaccharide-like component of the alga Prototheca (strain 289). JC Bedick A Shnyra DW Stanley RL Pardy, Naturwissenschaften 2001 88 482 485 10.1007/s00114-001-0269-8 11771478 (Pubitemid 33116460)
30. Lipopolysaccharide endotoxins. CR Raetz C Whitfield, Annu Rev Biochem 2002 71 635 700 12045108 10.1146/annurev.biochem.71.110601.135414 (Pubitemid 34800232)
31. The functional and structural properties of MD-2 required for lipopolysaccharide binding are absent in MD-1. N Tsuneyoshi K Fukudome J Kohara R Tomimasu JF Gauchat H Nakatake M Kimoto, J Immunol 2005 174 340 344 15611257
32. Comparison of lipopolysaccharide-binding functions of CD14 and MD-2. J Koraha N Tsuneyoshi M Kimoto JF Gauchat H Nakatake K Fukudome, Clin Diagn Lab Immunol 2005 12 1292 1297 16275943
33. Human Toll-like receptor 4 recognizes host-specific LPS modifications. AM Hajjar RK Ernst JH Tsai CB Wilson SI Miller, Nat Immunol 2002 3 354 359 10.1038/ni777 11912497 (Pubitemid 34308623)
34. Penta-acylated lipopolisaccharide binds to murine MD-2 but does not induce the oligomerization of TLR4 required for signal transduction. N Tsuneyoshi J Kohara U Bahrun S Saitoh S Akashi JF Gauchat M Kimoto K Fukudome, Cell Immunol 2006 244 57 64 10.1016/j.cellimm.2007.02.010 17420011 (Pubitemid 46659717)
35. Comparison of the growth-inhibitory effect of Hypericum perforatum L. extracts, differing in the concentration of phloroglucinols and flavonoids, on leukaemia cells. K Hostanska S Bommer M Weber B Krasniqi R Saller, J Pharm Pharmacol 2003 55 973 980 10.1211/0022357021251 12906754 (Pubitemid 36916687)
36. Aqueous ethanolic extract of St. John's wort (Hypericum perforatum L.) induces growth inhibition and apoptosis in human malignant cells in vitro. K Hostanska J Reichling S Bommer M Weber R Saller, Pharmazie 2002 57 323 331 12061257
37. Effect of drying temperature on alkylamide and cichoric acid concentrations of Echinacea purpurea. DL Stuart RB Wills, J Agric Food Chem 2003 51 1608 1610 10.1021/jf026213k 12617592
38. Effects of CCR5 and CD4 cell surface concentrations on infections by macrophagetropic isolates of human immunodeficiency virus type 1. EJ Platt K Wehrly SE Kuhmann B Chesebro D Kabat, J Virol 1998 72 2855 2864 9525605
39. Characteristics of a human cell line transformed by DNA from human adenovirus type 5. FL Graham J Smiley WC Russell R Nairn, J Gen Virol 1977 36 59 74 10.1099/0022-1317-36-1-59 886304
40. Identification of conserved and divergent domains within the envelope gene of the acquired immunodeficiency syndrome retrovirus. RL Willey RA Rutledge S Dias T Folks T Theodore CE Buckler MA Martin, Proc Natl Acad Sci USA 1986 83 5038 5042 3014529 10.1073/pnas.83.14.5038
41. Cellular and viral specificity of equine infectious anemia virus Tat transactivation. WJ Maury S Carpenter K Graves B Chesebro, Virology 1994 200 632 642 10.1006/viro.1994.1226 8178449 (Pubitemid 24146539)
42. Disruption of the FATB gene in Arabidopsis demonstrates an essential role of saturated fatty acids in plant growth. G Bonaventure JJ Salas MR Pollard JB Ohlrogge, Plant Cell 2003 15 1020 1033 12671095 10.1105/tpc.008946 (Pubitemid 36453297)
43. Epicuticular waxes of eceriferum mutants of Arabidopsis thaliana. A Hannoufa J McNevin B Lemieux, Phytochemistry 1993 33 851 855 10.1016/0031-9422(93)85289-4
44. New potential immunoenhancing compounds. Synthesis and pharmacological evaluation of new long-chain 2-amido-2-deoxy-D-glucose derivatives. U Valcavi C Albertoni A Brandt GB Corsi P Farina P Foresta G Pascucci MT Ramacci, Arzneimittelforschung 1989 39 1190 1195 2610709