Chemical Components

Naphthodianthrones (including hypericin and pseudohypericin). Flavonoids, mostly hyperoside, rutin, quercetin, isoquercitrin, quercetin and kaemferol, phenolics including hyperforin, procyanidins, essential oil, sterols (beta-sitosterol), vitamins C and A, xanthones and choline.

Manufactured products will vary in the concentrations and proportions of the different plant constituents present because these are influenced by the plant's place of origin, its harvest time and drying, extraction processes and storage conditions. Hyperforin, in particular, can be present in variable concentrations because it is unstable in light, air and most organic solvents (Mennini & Gobbi 2004). This is extremely important to remember when comparing studies, as variations in chemical

composition could be responsible for differences in results. It also provides a rationale for lack of interchangeability between brands.

Clinical note — Pharmacologically important constituents

It has generally been considered that most of the pharmacological activities of SJW are attributable to hypericin and the flavonoid constituent, hyperforin. Besides contributing to the antidepressant activity, hypericin is the primary constituent responsible for the photosensitivity reactions reported with high intakes. Hyperforin is also a major contributor to the herb's antidepressant activity (Butterweck et al 2003a, Mennini & Gobbi 2004) and considered the main constituent responsible for inducing the cytochrome P-glycoprotein and thereby producing drug interactions. Besides this, it demonstrates many other pharmacological effects such as antibacterial, anti-inflammatory and antineoplastic activities. Components previously considered void of activity have also been identified as important for pharmacological activity. For example, both procyanidin B2 and hyperoside increase the oral bioavailability of hypericin by 58% and 34%, respectively, and therefore, its clinical effects (Butterweck et al 2003b). A report published in June 2003 demonstrated that an extract devoid of both hyperforin and hypericin still exhibited antidepressant activity (Butterweck et al 2003a). Other constituents with antidepressant activity were identified and include hyperoside, isoquercitrin and miquelianin, and the 3-O-galactoside, 3-O-glucoside and 3-O-glucuronide of quercetin.

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