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Hypericum in Infection: Identification of Anti-Viral and Anti-Inflammatory Constituents Diane F

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Hypericum in Infection: Identification of Anti-Viral and Anti-Inflammatory Constituents Diane F Food Science and Human Nutrition Publications Food Science and Human Nutrition 8-2009 Hypericum in infection: Identification of anti-viral and anti-inflammatory constituents Diane F. Birt Iowa State University, [email protected] Mark P. Widrlechner United States Department of Agriculture, [email protected] Kimberly D.P. Hammer Iowa State University Matthew L. Hillwig Iowa State University FJinogqillowan thig Ws aeind additional works at: http://lib.dr.iastate.edu/fshn_ag_pubs Iowa State University Part of the Agricultural Science Commons, Agriculture Commons, Agronomy and Crop SSece ienencxt peages Cforommon additionals a,uFthoroods Science Commons, Genetics Commons, Horticulture Commons, Human and Clinical Nutrition Commons, Medicinal-Pharmaceutical Chemistry Commons, and the Microbiology Commons The ompc lete bibliographic information for this item can be found at http://lib.dr.iastate.edu/ fshn_ag_pubs/36. For information on how to cite this item, please visit http://lib.dr.iastate.edu/ howtocite.html. This Article is brought to you for free and open access by the Food Science and Human Nutrition at Iowa State University Digital Repository. It has been accepted for inclusion in Food Science and Human Nutrition Publications by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. Hypericum in infection: Identification of anti-viral and anti-inflammatory constituents Abstract The oI wa Center for Research on Botanical Dietary Supplements seeks to optimize Echinacea, Hypericum, and Prunella botanical supplements for human-health benefit, emphasizing anti-viral, anti-inflammatory, and anti- pain activities. This mini-review reports on ongoing studies on Hypericum. The eC nter uses the genetically diverse, well-documented Hypericum populations collected and maintained at the USDA-ARS North Central Regional Plant Introduction Station (NCRPIS), and the strength of research in synthetic chemistry at Iowa State University to tap natural diversity, to help discover key constituents and interactions among constituents that impact bioactivity and toxicity. The NCRPIS has acquired more than 180 distinct populations of Hypericum, with a focus on Hypericum perforatum L. (Hypericaceae), representing about 13% of currently recognized taxa. Center chemists have developed novel synthetic pathways for key flavones, acyl phloroglucinols, hyperolactones, and a tetralin that have been found in Hypericum, and these compounds are used as standards and for bioactivity studies. Both light-dependent and light-independent anti-viral activities have been identified by using bioactivity-guided fractionation of H. perforatum and a HIV-1 infection test system. Our Center has focused on light-independent activity, potentially due to novel chemicals, and polar fractions are undergoing further fractionation. Anti-inflammatory activity has been found to be light- independent, and fractionation of a flavonoid-rich extract revealed four compounds (amentoflavone, chlorogenic acid, pseudohypericin, and quercetin) that interacted in the light to inhibit lipopolysaccharide- induced prostaglandin E2 activity. The eC nter continues to explore novel populations of H. perforatum and related species to identify constituents and interactions of constituents that contribute to potential health benefits er lated to infection. Keywords Hypericum, infection, anti-viral, anti-inflammatory, phloroglucinols, flavonoids, NCRPIS, Genetics Development and Cell Biology, Chemistry Disciplines Agricultural Science | Agriculture | Agronomy and Crop Sciences | Chemistry | Food Science | Genetics | Horticulture | Human and Clinical Nutrition | Medicinal-Pharmaceutical Chemistry | Microbiology Comments This article is from Pharmaceutical Biology 47, no. 8 (August 2009): 774–782, doi:10.1080/ 13880200902988645. Rights Works produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The onc tent of this document is not copyrighted. This article is available at Iowa State University Digital Repository: http://lib.dr.iastate.edu/fshn_ag_pubs/36 Authors Diane F. Birt, Mark P. Widrlechner, Kimberly D.P. Hammer, Matthew L. Hillwig, Jingqiang Wei, George A. Kraus, Patricia A. Murphy, Joe-Ann McCoy, Eve S. Wurtele, Jeffrey D. Neighbors, David F. Wiemer, Wendy J. Maury, and Jason P. Price This article is available at Iowa State University Digital Repository: http://lib.dr.iastate.edu/fshn_ag_pubs/36 Pharmaceutical Biology, 2009; 47(8): 774–782 RESEARCH ARTICLE Hypericum in infection: Identification of anti-viral and anti-inflammatory constituents Diane F. Birt1,2, Mark P. Widrlechner1,3,7, Kimberly D. P. Hammer 1,2,4, Matthew L. Hillwig1,5, Jingqiang Wei1,6, George A. Kraus1,6, Patricia A. Murphy1,2, Joe-Ann McCoy1,7,10, Eve S. Wurtele1,5, Jeffrey D. Neighbors1,8, David F. Wiemer1,8, Wendy J. Maury1,9, and Jason P. Price1,9 1The Center for Research on Botanical Dietary Supplements,2 Department of Food Science and Human Nutrition, 3Departments of Horticulture and Agronomy, 4Interdepartmental Genetics Graduate Program, 5Department of Genetics, Development, and Cell Biology, 6Department of Chemistry, Iowa State University, Ames, IA, USA, 7US Department of Agriculture-Agricultural Research Service, North Central Regional Plant Introduction Station, Ames, IA, USA, 8Department of Chemistry, University of Iowa, Iowa City, IA, USA, 9Department of Microbiology, University of Iowa, Iowa City, IA, USA, and 10current address: Bent Creek Institute, The North Carolina Arboretum, Asheville, NC, USA Abstract The Iowa Center for Research on Botanical Dietary Supplements seeks to optimize Echinacea, Hypericum, and Prunella botanical supplements for human-health benefit, emphasizing anti-viral, anti-inflammatory, and anti-pain activities. This mini-review reports on ongoing studies on Hypericum. The Center uses the genetically diverse, well-documented Hypericum populations collected and maintained at the USDA-ARS North Central Regional Plant Introduction Station (NCRPIS), and the strength of research in synthetic chem- istry at Iowa State University to tap natural diversity, to help discover key constituents and interactions among constituents that impact bioactivity and toxicity. The NCRPIS has acquired more than 180 distinct populations of Hypericum, with a focus on Hypericum perforatum L. (Hypericaceae), representing about 13% of currently recognized taxa. Center chemists have developed novel synthetic pathways for key fla- vones, acyl phloroglucinols, hyperolactones, and a tetralin that have been found in Hypericum, and these compounds are used as standards and for bioactivity studies. Both light-dependent and light-independent anti-viral activities have been identified by using bioactivity-guided fractionation of H. perforatum and a HIV-1 infection test system. Our Center has focused on light-independent activity, potentially due to novel chemicals, and polar fractions are undergoing further fractionation. Anti-inflammatory activity has been found to be light-independent, and fractionation of a flavonoid-rich extract revealed four compounds (amentoflavone, chlorogenic acid, pseudohypericin, and quercetin) that interacted in the light to inhibit lipopolysaccharide-induced prostaglandin E2 activity. The Center continues to explore novel populations of H. perforatum and related species to identify constituents and interactions of constituents that contrib- ute to potential health benefits related to infection. Keywords: Hypericum; infection; anti-viral; anti-inflammatory; phloroglucinols; flavonoids Introduction: center organization genetic, developmental, and biochemical diversity of Echinacea, Hypericum, and Prunella species to improve The Iowa Botanical Center is unique among Office of our understanding of the key constituents that contrib- Dietary Supplements (ODS) Botanical Supplements ute to their bioactivity. The range of variation in these Research Centers in that we have demonstrated the plants, when systematically analyzed, provides a strong capacity to harness interdisciplinary research on the foundation on which to develop the strategies and tools Address for Correspondence: Diane F. Birt, Department of Food Science and Human Nutrition, Iowa State University, 215 MacKay Hall, Ames, IA 50011, USA. Tel: 515-294-9873. Fax: 515-294-6193. E-mail: [email protected] (Received 17 April 2009; accepted 21 April 2009) ISSN 1388-0209 print/ISSN 1744-5116 online © 2009 Informa UK Ltd DOI: 10.1080/13880200902988645 http://www.informapharmascience.com/phb Hypericum in infection 775 needed to produce the most efficacious products for a were described by Widrlechner and McKeown (2002), growing body of consumers. This mini-review will focus and a recent overview of this important collection and on some of our work with Hypericum. its relationship to the Center was presented by Birt Our general approach is to identify chemical pro- et al. (2008). The NCRPIS Prunella collection is a recent files and the key compounds that define these plants’ development, resulting from the inclusion of this genus bioactivity, and to provide a context that can be used to in research projects incorporated into the Center’s 2007 reinterpret past studies and, in turn, serve as the basis Project Renewal, while the more extensive NCRPIS for future research. The primary goal of our Center is to Hypericum collection is described in detail below. These improve our understanding of the characteristics that resources
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