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An Overview on Hypericum Perforatum Linn Review Article An overview on Hypericum perforatum Linn. U M Rao Vattikuti and Veeresham Ciddi* Medicinal Plant Biotechnology Laboratory University College of Pharmaceutical Sciences Kakatiya University Warangal-506 009, Andhra Pradesh, India *Correspondent author; E-mail: [email protected] Received 14 September 2004; Revised 2 May 2005 Abstract flowers contain a group of reddish fluorescent dianthrone pigments with 2 Population of the modern world is suffering from dangerous ailments like cancer, AIDS biological activity . It was also reported and depression which have been successfully treated by some herbal medicines. The potentiality of that the biosynthesis of hypericins is Hypericum perforatum Linn. has been proven in treating these diseases. Hypericin, hyperforin connected with morphogenesis and and their analogs are the phytoconstituents of this plant having therapeutic value. The significance formation of dark red coloured oil glands of these constituents is attributed to their botanical safety and therapeutic efficacy. This review on the leaves of the plant3. It has been discusses the pharmacology, extraction and analytical methods of chemical constituents reported on H. perforatum and its plant tissue cultures. known since Greek and Roman times, Dioscorides (1st century A.D) and Galen Keywords: St. John’s Wort, Hypericin, Hyperforin, Biosynthesis, Plant tissue culture, Analysis. described its medicinal properties (2nd IPC code; Int. cl.7 ⎯ A01G 7/00, A61K 35/78, A61P 25/24, A61P 31/12, A61P 31/98, century A.D). It was widely used in the A61P 35/00 folk medicine in European countries as a soothing agent, an antiphlogistic in Introduction approximately one metre high with inflammation of bronchi and urogenital opposite and paired branches. The leaves track, in haemorrhoid treatment, a The genus Hypericum Linn. are opposite and sessile, upto 2cm long, healing agent in the treatment of traumas, consists of nearly 288 species. Of which oblong and contain numerous translucent burns, scabs and ulcers of various kinds H. perforatum Linn., H. maculatum glandular dots, which are visible against and other local and general illness. Today Crantz, H. tomentosum Linn., H. light. The yellow flowers contain 5 petals this drug is little used for these traditional bithynicum Boiss., H. glandulosum with many stamens protruding. These purposes but is largely used in the Gilib. and H. beliaricum Linn. are treatment of depression and reported to contain hypericin1. H. AIDS. perforatum, commonly known as St. John’s Wort (Hindi ⎯ Balsana, Biosynthesis of Bassant, Dendhu) is a potent medicinal Hypericin and plant and is one of the top selling herbs Hyperforin in USA. It is a herbaceous perennial plant of family Hypericaceae widely The biosynthesis of distributed in temperate regions of hypericin (Fig 1&2) involves a Europe, Asia, North Africa and USA. In polyketide derivative through 107 India it grows in Himalayas at higher acetate pathway . The altitudes and in the hills of central parts polyketide (1) with a series of intermediates transforms in to of the country. The plant grows Hypericum perforatum 368 Natural Product Radiance Review Article Chemical composition shown a significant antidepressant activity by inhibiting the enzyme monoamino The plant is reported to contain following categories of chemical constituents: oxidase (MAO)21. The other mechanisms of antidepressant activity are, inhibition Dianthrone derivatives : Hypericin2,4 of dopamine β-hydroxylase22 in vitro, Pseudohypericin5, 6 inhibition of synaptic uptake of serotonin Protohypericin7 and dopamine23, 24, inhibition of catechol- O-methyl transferase25 in vitro, Phloroglucinol derivatives : Hyperforin8 Furohyperforin9 suppression of interlukin-6 in blood Adhyperforin10 samples26 in vivo, modulation of Xanthones11 expression of serotonin receptors27. The antidepressant activity of hyperforin is Essential oil attributed to its inhibition of neuronal Monoterpenes12 : α-Pinene, β-Pinene, Limonene Sesquiterpenes13 : Caryophyllene, Humulene uptake of serotonin, norepinephrine and dopamine like many other antidepressants Flavonols : Catechins14 and also inhibits GABA and α-glutamate uptake28. The antidepressant activity of 15 Flavonoids : Hyperoside hypericum is not only limited to hypericin Quercetin16 Quercetrin17 and hyperforin, xanthones of the plant are Rutin16 also reported to exhibit this property11. Biapigenin18 Antiviral activity ⎯ Kaempferol19 Hypericin is a well-known photosensitizing agent used in the n-Alkanols20 : 0.42% of total herb 1-Tetracosanol (9.7%), 1-Hexacosanol (27.4%), photodynamic therapy of cancer and viral 1-Octacosanol (39.4%), 1-Triacontanol (23.4%) infections. The photodynamic therapy involves the combination of photosensitizing agent and visible light at atrochrysone (2). Atrochrysone on CoA is subsequently lengthened by 3 the absorption wavelength of the dehydration converts into emodine malonyl CoA units and cyclization in to compound. Lavie et al29 demonstrated the anthrone (3). Emodine anthrone readily an intermediate, which would then lead inhibitory effect of hypericin and transforms into hypericin (4) via oxidative to the acylphloroglucinol. Elaboration of pseudohypericin against vesicular free radical chemistry. hyperforin (5) from the unsubstituted stomatitis, influenza virus and herpes The biosynthesis of hyperforin acylphloroglucinol precursor is assumed simplex virus types II and I. Inactivation (Fig 1 & 3) involves isoprenoid moieties, to be with the participation of the geranyl of murine cytomegalo virus, sindbis virus which are derived predominantly via the pyrophosphate and three dimethyl- and HIV-I on exposure to fluorescent light non-mevalonate pathway85. The allylpyrophosphate units. While the with hypericin treatment was reported first acylphloroglucinol (4) moiety is sequence of remaining steps remain to be time by Hudson et al30 and Lopez-Bazzocchi generated via a polyketide type a large extent unidentified. et al31. Both hypericin and pseudohypericin mechanism. This acylphloroglucinol is prevents the viral fusion by the generation formed from isobutyryl-CoA (3) as a starter Pharmacological activities of singlet oxygen up on illumination32. The point, which in turn is formed from two antiviral activity against retroviruses like HIV units of pyruvate via α-acetolactate (1) Antidepressant activity ⎯ involves combination of its photodynamic and α-ketoisovalerate (2). The isobutyryl- Hypericin in a standardized extract has and lipophilic properties. Vol 4(5) September-October 2005 369 Review Article Fig. 1 : Structures of Hypericin and Hyperforin Fig. 2 : Biosynthesis of Hypericin 370 Natural Product Radiance Review Article c Fig. 3 : Biosynthesis of Hyperforin Hypericin binds the cell membranes and significance of hypericin in photodynamic activity. Hyperforin activates a crosslinks the viral proteins leading to its therapy of cancer both in vitro and in mitochondria mediated apoptosis when inability to retrieve the reverse vivo34. Hypericin seems to inhibit EGF added to MT-450 cells. In in vivo, transcriptase activity33. (Epidermal Growth Factor) receptor and hyperforin inhibited the growth of Anticancer activity ⎯ PTK (Protein Tyrosine Kinase) activity. A antologous MT-450 breast carcinoma in Hypericins have been found active against review35 on the mechanism of action of immuno-competent Wistar rats to a similar human leukaemia, squamos cell hypericin and its interaction with cellular extent as that of Paclitaxel without any carcinoma, nasopharyngial carcinoma, components reveals that the signs of acute toxicity36. mouse mammary carcinoma and photogenerated pH drop can achieve the The pharmacology of this plant fibroblasts. Several studies have proven the potentiation of hypericin’s photodynamic also reveals a broad spectrum of activities Vol 4(5) September-October 2005 371 Review Article like analgesic37, anti-anxiety38, anti- permeabilization, immobilization and contrast to this reduced levels of cellular alcoholic39, antispasmodic40, antioxidant41, various other strategies to improve the capacity to produce hypericin in St. John’s calcium channel blocker42, gene production of active constituents Wort seedlings grown in Nickel expression induction43, wound healing44, compared to the intact plant. This supplemented medium was reported by smooth muscle relaxant45, sleep technique has already been Murch et al 63. potentiation46, anti-inflammatory47 and commercialized for the production of In order to eliminate the quality anti-microbial 48, 49. taxol, shikonin and rosmarinic acid55. impairment in St John’s Wort products, Saxena et al 64 have reported six different Production of Hypericin and Callus formation and plant culture systems for in vitro propagation Hyperforin through tissue cultures regeneration of the plant to compare the biomass and secondary metabolite production with Over the last few years, St. John’s Santarean and Pretto56 reported green houseplants. Of the six culture Wort producers have enjoyed a callus formation and plant regeneration systems they found that growth in large tremendous surge in interest and sales due within few months, from leaf explants of vessel with gelled medium under forced to its potential in the treatment of the species. Li et al 57 reported callus and ventilation (LFV system) was optimal for depression and AIDS. Linde50 revealed the suspension cultures from the leaves and the production of biomass and secondary efficacy of St. John’s Wort when compared stems. Rani et al58
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