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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > October  >
In the Classroom
Chemistry of St. John's Wort: Hypericin and Hyperforin
John J. Vollmer and Jon Rosenson
Department of Chemistry, Mills College, Oakland, CA 94613
Cover
October 2004
Vol. 81 No. 10
p. 1450
Abstract
St. John's wort is a common plant that has been used medicinally for over 20 centuries. This herb is currently used by millions of people, primarily as natural antidepressant; yet, its efficacy is still under constant debate. St. John's wort contains a large aromatic molecule, hypericin, twisted by steric interactions into the shape of a propeller. For use as antidepressant, St. John's wort is standardized to the content of hypericin, but this molecule was recently found not to be the active ingredient. A totally different bicyclic molecule with complex substitution pattern, hyperforin, was then studied as the causative agent. Both molecules are strongly active in biological systems. Hypericin has shown antiviral activity and is a potent natural photosensitizer that has been used in photodynamic therapy against cancer and against HIV in stored blood. Hyperforin was found to activate a particular receptor in the liver that induces the production of an enzyme used for the metabolism of medications. This effect causes more rapid breakdown of many prescription medications and can interfere with their effectiveness. This finding should prompt a reevaluation of regular use of St. John's wort.
More Information
*  Citation
 Vollmer, John J.; Rosenson, Jon. J. Chem. Educ. 2004 81 1450.
*  Keywords
 Biochemistry; Bioorganic Chemistry; Consumer Chemistry; Drugs / Pharmaceuticals; Medicinal Chemistry; Natural Products; Organic Chemistry; Plant Chemistry
*  History
 Created:
Last Updated:		 August 31, 2004
September 8, 2004
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