Hypericin from Hypericum perforatum

Hypericin, from Hypericum perforatum (St. John s wort)... 

Sigma receptor ligands bind to metabotropic GPCRs as well as ionotropic cr-Rs (Chapter 3). Endogenous ligands for cr-Rs include some opiates. Sigma-R activation can have antitussive, anxiolytic and ulceroprotective effects. Hypericin from Hypericum perforatum (St John s wort) is... 

Butterweck V, Petereit F, Winterhoff H, Nahrstedt A. Solubilized hypericin and pseudohypericin from Hypericum perforatum exert antidepressant activity in the forced swimming test. Planta Med 1998 64 291-294. 

Stock S, Hoelzl J. Pharmacokinetic tests of (14C)-labeled hypericin and pseudohypericin from Hypericum perforatum and serum kinetics of hypericin in man. Planta Med 1991 57 A61. 

Karppinen K, Hokkanen J, Manila S, Neubauer P, Hohtola A (2008) Octaketide-producing type III polyketide synthase from Hypericum perforatum is expressed in dark glands accumulating hypericins. FEBS J 275 4329-4342... 

Kusari, S., Lamshoft, M., Zuhlke, S. and Spiteller, M. (2008) An endophytic fungus from Hypericum perforatum that produces hypericin. /. Nat. Prod., 71, 159-62. 

Anthrone and anthraquinone derivatives are used as laxatives (F 2). The compounds formed in plants may repel potential predators (E 5.5.3). Hypericin, a photodynamic compound, is a feeding deterrent from Hypericum perforatum St. Johns wort, E 5.5.3). 

Hypericin, the dark-red pigment from Hypericum perforatum, is a dehydrodianthrone, structurally an anthraquinone. However, it does not break down to anthrone in the bowel and is without laxative action. Hypericin has been thoroughly investigated and used (generally in Hypericum extracts standardised to hypericin content) for antidepressant and antiviral activities (Bombardelli and Morazzoni 1995). 

Protopseudohypericin, pseudohypericin, proto pericin, and hypericin were extracted from Hypericum perforatum blossoms and baseline resolved on a C g column (A = 590nm) using a 12-min 70/30 -> 90/10 (at 8min hold 4min) (5/4 methanol/acetonitrile)/(wat [0.1 M triethylammonium acetate]) gradient [392]. Excellent peaks shapes were obtained. The total injected mass of the four compounds was i roximately 12pg. 

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. [ ].

Peebles KA, Baker RK, Kurz EU, Schneider BJ, Kroll DJ. Catalytic inhibition of human DNA topoisomerase Ila by hypericin, a naphthodianthrone from St. John s wort (Hypericum perforatum). Biochem Pharmacol 2001 62 1059-1070. 

Several investigations have studied the in vivo antidepressant activity of this herb and of compounds isolated from it. For example, a commercially available extract of the aerial parts of Hypericum perforatum LI 160 and hypericin, Fig. (13) showed pronounced activity in selected animal bioassays. These include the forced swimming test and the tail suspension test, used to determine antidepressant activity, and tests indicating activity on the central nervous system, such as body temperature and ketamine-induced sleeping time [231,232],... 

Finally, the stimulating effect of cork pieces on hypericin and pseudophypericin production in cells of shoots regenerated from the callus cultures of Hypericum perforatum has also been reported [355],... 

Hypericin 1 is present in plants, insects and protozoa. In plants, apart from H. perforatum, it occurs in a number of other species of Hypericum, namely H. hirsutum, H. maculatum, H. nummularium and H. triquetrifolium [17]. It is located in minute glands on different parts of the plants such as young stems, leaves and flowers. Interestingly, hypericin 1 is found in the integument of Australian Lac insects of the Coccoidea family, and appears with a number of structurally-related compounds [18, 19]. In protozoa, the blue-green ciliate, Stentor coerulus possesses a photoreceptor, stentorin, which consists of proteins bound to hypericin 1 [20]. 

Nature St. John s wort is made from dried flowers of Hypericum perforatum, the active constituents of which include hypericin and h3q3erforin. 

Figure 8 Thin-layer chromatography of Hypericum perforatum. The chromatograms show no important differences between the herbai drug and the extract except the red spots in front. Both spots are the resuit of chiorophyll, which is eliminated by the extraction procedure. Red spots Hypericin and pseudohypericin yeiiow and orange spots fiavonoids (glycosides R, 0.5 agly-cones R, 0.8) blue spot ubiquitous plant acids. Reference traces on the left Hypericin chlorogenic acid and quercetin. (Reproduced with permission from Beat Meier, Zeller AG, Herbal Remedies, Romanshorn, Switzerland.)...

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