Hypericum perforatum Hyperforin, Hypericin

Fig. 2.49. Profile of Hypericum perforatum extract with the H LC-MS attributions of the components detected. 1 = chlorogenic acid isomer 2 = 3-0- -coumaroylquinic acid 3 = chlorogenic acid 4 = rutin 5 = hyperoside 6 = isoquercitrin 7 = 3,3, , , 7-pentahydroxyflavanone 7-0-rhamnopyranoside 8 = quercitrin 9 = quercetin 10 = 13,118 tapigenin 11 = pSeudohypericin 12 = hypericin 13 = hyperforin analogue 14 = hyperform dialogue 15 = hyperforin 16 = adhyperforin. Reprinted with permission from M. Brolis eta. [ ].

To ensure lot-to-lot consistency, standardization of extracts often relies on constituents as biomarkers for plant identity and potency. SJW Hypericum perforatum), a perennial shrub traditionally used as a mood enhancer and mild antidepressant, has been tested in dozens of clinical trials, with mixed results for efficacy. Some of its purported bioactive constituents include naphthodianthrones, including hypericin flavonoids phloroglucinols, including hyperforin and essential oils. For many years, hypericin was presumed to be the active component. As a result most extracts were standardized based on hypericin concentration. Recent data, however, support other components such as hyperforin and the flavanoids, that may also contribute to the therapeutic efficacy of the SJW extracts (33-35). Because these secondary components were previously unaccounted for in the standardization of the former clinical test articles, and because these constituents are chemically unrelated to and their content within the plant varies independently of hypericin, it has been argued that the potency of these constituents in any particular batch was unlikely to be similar to that of other batches. This variability between batches could explain the observed differences in the clinical trial results (36). 

St. John s wort. The St. John s wort plant (Hypericum perforatum Figure 6.4) is an increasingly popular herbal supplement that proponents claim has the ability to cure a vast array of ailments. St. John s wort appears to boost the release of the neurotransmitter serotonin in the brain, which may be the reason it is able to treat anxiety and depression. The herb contains numerous substances, two of which, hypericin and hyperforin, maybe key active ingredients. St. John s wort appears to be effective in relieving the muscle pain associated with fibromyalgia and the tissue pain associated with hemorrhoids. The herb comes in tablet, capsule, cream, and ointment forms and must be taken for several weeks before it takes full effect. St. John s wort should not be taken with antidepressants such as... 

Hypericum perforatum (devil s scourge, goat weed, rosin rose, St. John s wort, Tipton weed, witch s herb) contains the naphthodianthrones hypericin and pseudohypericin, flavonoids, such as hyperoside, isoquercitin, and rutin, and phloroglucinols, such as adhyperforin and hyperforin. It is effective in mUd to moderate depression (1). 

Key Words Hypericum perforatum, hypericin hyperforin antidepressant anxiolytic P450 enzyme induction. 

Hypericum perforatum L. St. John s wort Shoots Depression, antiviral agent Hyperforin, hypericin, flavonol glycosides... 

In a randomised, crossover study in 12 healthy subjects, one tablet of St John s wort three times daily for 3 weeks modestly decreased the AUC of both R- and S -warfarin by about 25% after a single 25-mg dose of warfarin taken on day 14. In this study, the brand of St John s wort used was Biog-lan tablets, each tablet containing an extract equivalent to 1 g of Hypericum perforatum flowering herb top containing 825 micrograms of hypericin and 12.5 mg of hyperforin. ... 

Hypericum perforatum (St. John s Wort) was extracted and analyzed for pseuo-dohypericin, hypericin, hyperforin, and adhyperforin content. Excellent peak shapes... 

ESI-MS in negative mode of Hypericum perforatum extracts provides typical fingerprints showing three different classes of compounds, i.e., flavonoids, hypericins, and hyperforins (Fig. 2). The abundant ions at m z 535 and 549 are due to [M-H] ions of hyperforin and adhyperforin, respectively. Deprotonated molecules ([M-H] ) of hypericin m z 503), pseudohypericin (miz 519), and... 

Figure 2 Typical negative ESI-MS mass spectrum of Hypericum perforatum extract. ESI-MS, electrospray ionization mass spectrometry Mi, rutin M2, hyperforin M3, pseudohypericin M4, hypericin M5, adhyperforin Me, isoquerci-trin/hyperoside. 

Hypericin and pseudohypericin (Fig. 21) are naphthodianthrones and occur in St. John s wort Hypericum perforatum, Clusiaceae). These dark-red compounds are accumulated in glands on the margin oiK perforatum leaves and petals. It was assumed for a long time that they represent the antidepressant principle in extracts of St. John s wort. Recently, however, it became evident that the prenylated acylphloroglucinols hyperforin and adhyperforin are responsible for most of the pharmacological effects. 

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