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Antidepressant Activity of Hyperforin Conjugates of the St.John's Wort, Hypericum Perforatum Linn.: an Experimental Study

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Antidepressant Activity of Hyperforin Conjugates of the St.John's Wort, Hypericum Perforatum Linn.: an Experimental Study Indian Journal of Experimental Biology VoL 39, December 2001, pp. 1302-1304 Antidepressant activity of hyperforin conjugates of the St.John's wort, Hypericum perforatum Linn.: An experimental study A V Muruganandam & S K Bhattacharya* Department of Pharmacology, Institute of Medical Sciences, Banaras Hindu University, Varanasi 221 005, India and S Ghosal Drug Research and Deve lopment Centre, 1078, Jessore Road, Calcutta 700 028, India Received 11 November 2000; revised 26 July 2001 Nine extracts of H. petforatwn, containing hyperfo rin in conjugated forms, but devoid of free hyperforin and adhyper­ forin, were subj ected to antidepressant screening using the forced swim test (FST). The observed activity was compared with that of SJW extracts containing hyperforin and adhyperforin (in free form). Results indicate that hyperforin conjugates exhibit significant antidepressant acti vity as evidenced by the reduced immobility period in the FST in rats. Extracts of Hypericum perforatum Linn. (St.John's ministered (50 mg/kg/day) orally for three days in wort, SJW) have shown significant antidepressant 0 .3% CMC suspension. The experiment was per­ activity in both expenmenta. 1 1· 2 an d c l'mtca . l stu d'te s 3 . formed after 45 min of the final administration of the Earli er, hypericin, a napthodiantherene derivative pre­ drugs or the vehicle. sent in SJW, was thought to be the active constituent SJW Extracts- In a typical experiment, the dried responsible for the antidepressant activit/. However, overground parts of the H. peiforatum (SJW), col­ in later studies the earlier results could not be con­ lected from Northern India, were extracted continu­ firmed5. More recently, hyperforin, a prenylated ously with aqueous acetone (Soxhlet, 12h). The sol­ phloroglucinol derivative, present in the plant, has vent was removed from the extract under vacuum. A been projected as primarily responsible for the antide­ portion of the dried extract was accurately weighed, 6 9 pressant activity of SJW . In the present study, SJW dispersed in water and further extracted with chloro­ collected from Northern parts of India were examined form. The chloroform soluble fraction was dried and for their hyperforin and adhyperforin contents by redissolved in methanol (1 mg/ml) and subjected (20 HPLC, usi111g authentic markers. Interestingly, in five ~-tl) to HPLC analysis (WATERS ASSOCIATES of the nine extracts examined (SJW 1-5) hyperforin HPLC assembly equiped with PDA detector; column : and adhyperforin were vicariously represented by the reverse phase RP-Cl8 (Novapak 3.9xl50 mm); elu­ corresponding conjugates. The remaining four ex­ ent: acetonitrile - water- phosphoric acid (80:20:01); tracts (SJW 6-9) contained hyperforin, adhyperforin flow rate : 1.2 mVmin; pressure 1500 psi; scanning at and also hyperforin conjugates (as minor entities). In 270 nm) using hyperforin and adhyperforin as mark­ thi s study, the contribution of hyperforin conjugates, ers to eliminate the possibility of their occurrence in if any, on the antidepressant activity of SJW was the extract. Likewise, the HPLC spectrum of hyper­ studied on forced swim test (FST). FST was selected forin conjugates exhibited absence of hyperforin and for thi s study since its relevance has been demon­ adhyperforin. strated with a large number of clinically used antide­ 10 The nature of the hyperforin conjugates was estab­ pressants . li shed by comprehensive spectroscopic analyses (UY, Animals-Albino rats (CF strain) of either sex. 1 HNMR) and crucial chemical transformation of hy- were housed in colony cages maintained at 22° ± I °C . 10 perf onn . in a 12 hr darkilight cycle. The rats had free access to Forced swim test- The rats were pl aced in a water and standard lab chow. SJW extracts were ad- chambers (45x20 em) containing water up to 25 em *Correspondent author: Fax No. 0542-316068 (25° ± 2°C), so that it could not touch the bottom of . E. mai l:salil @banaras.ernet.in the cylinder with its hind limb or tai l, or climb over NOTES 1303 Table !- Percentage abundances of hyperforin, adhyperforin· and its conjugates in SJW extracts and their effect on Forced Swim Test (FST) in rats [Values are mean± SE, n=6] Groups % Relative Abundance FST Hyperforin Adhyperforin Hyperforin conjugates Immobility period (sec) Vehicle 115.2 ± 9.37 SJW I 16.31 46.0 ± 4.25•• SJW2 06.32 60.0 ± 5.51 aa SJW3 09.64 42.6 ± 6.14aa SJW4 14.31 49.8 ± 6.14aa SJW 5 12.42 69.0 ± 4.45 .. SJW6 4.60 4.15 00.53 52.0 ± 5.78aa SJW 7 0.33 0.09 02.48 41.8 ± 5.02aa SJW 8 1.70 0.92 05.2 1 48.4 ± 4.93aa SJW9 0.53 0.31 08.42 39.4 ± 2.32aa Imipramine 62.3 ± 3.81 aa aaP<O.OI (One way ANOV A followed by Newmann-Keuls test). Identities of hyperforin, adhyperforin and its conjugates were based on the UV spectral ()"max 272 nm) and 1HNMR characteristi cs. Hyperfori n tR = I 0. 1; adhyperforin tR = 11.3; hyperforin conjugates tR = 2.3 to 6.5. the edge of the chamber. Two swim sessions were pressant actiVIty. This was evidenced from the sig­ conducted, an initial 15 min pretest, followed by a 5 nificantly reduced immobility period of the SJW min test 24 hr later. The period of immobility (animal treated rats. Thus, our findings are consonant with the 6 9 remains floating in water without struggling and recent reports - that hyperforin and adhyperforin making only those movements necessary to keep its contribute to the antidepressant activity of the SJW. head over water) during the 5 min test period was Interestingly, the SJW extracts (SJW 1-5), which were 11 noted • completely devoid of free hyperforin and adhyperfo­ The test paradigm is based on the observation that rin, and contained more polar hyperforin conjugates, rats or mice, when forced to swim in a restricted space exhibited like SJW extract (6-9) containing hyperforin from which they cannot escape, eventually cease at­ and adhyperforin, significant antidepressant acti vity tempts to escape and become immobile, except from in the FST as well (Table 1). The extent of antide­ the small movements necessary to keep their heads pressant activity of hyperforin conjugates and free above water. This characteristic behavioural immo­ hyperforins was of same order. In the case of for­ bility refl ects a state of despair in rats and mice. mer, the advantage of using the hyperforin conjugates Treatment with antidepressant agents reduce the im­ lies in the stability compared to that of hyperforin and 12 13 mobility period . SJW extracts containing hyperforin adhyperforin . and adhyperforin (SJW 6-9, 50 mgfkg/day) signifi­ The authors are thankful to CSIR, New Delhi and cantly reduced the immobility period in comparison to Indian Herbs, Saharanpur, India, for financial and vehi cle treated rats. Interestingly, the SJW extracts technical assistance. (SJW 1-5, 50 mg!kg/day), containing hyperforin conjugates, and devoid of free hyperforin and adhy­ References , perforin, also significantly reduced the immobility I Bhattacharya SK, Chakrabarti A & Chatterjee SS, Activity period in treated rats (Table 1). The antidepressant profiles of two hyperforin-containing Hypericum extracts in activity of SJW extracts was compared with that of behavioural models, Pharmacopsychiat, 31 ( 1998) 22. imipramine (10 mg/kg, ip), a clinically used tricyclic 2 Chatterj ee SS, Noldner M, Koch E & Erdemeier C, Antide­ antidepressant. pressant activi ty of Hypericum perforatum and hyperforins : Both SJW extracts (SJW 1-5), containing only hy­ the neglected possibility, Pharmacopsychiat, 31 (Suppl I) (1998) 7. perforin conjugates (but free from hyperforin and ad­ 3 Muller WE, Singer, A, Wonnemann, M, Hafner, U, Rolli , M hyperforin), and SJW extracts (SJW 6-9), containing & Schafer C, Hyperforin represents the neurotransmitter re­ hyperforin, adhyperforin and also hyperforin conju­ uptake inhibiting constituent of Hypericum extract, Phanna­ gates (as minor entities), showed significant antide- copsychiat, 3 1 ( 1998) 16. 1304 INDIAN J EXP BIOL, DECEMBER 2001 4 Mulder H & Zoller M, Antidepressive Wirkung eines auf forin for the clinical efficacy, Pharmacopsychiat, 31 (1998) den Wirkstoffkomplex Hypericin standardisierten, Hyperi­ 54. cum extraktes Arzneim Forsch, 34 (1984) 918. 9 Muller WE, Rolli, M, Schafer, C and Hafner, U, Effect of 5 Sparenberg B, Demisch L & Holzl J, Investigations of the Hypericum extract (Ll-160) in biochemical models of anti­ antidepressive effects of StJohn's wort, Pharm Zig Wiss, 2 depressant activity, Pharmacopsychiat, 30 (1997) 102. (1993) 50. 10 Ghosal S, Hypericum perforatum composition, USA patent pending ( 1999). 6 Chatterjee SS, Bhattacharya SK, Wonnemann M, Singer A & 11 Willner P, The validity of animal models of depression, Muller WE, Hyperforin as a possible antidepressant compo­ nent of Hypericum extracts, Life Sciences, 63 ( 1998) 499. Psychopharmacology (Ber), 83 ( 1984) L 12 Porsolt RD, Anton G, Blavet N & Jalfre M, Behav ioural de­ 7 Biber A, Fischer H, Romer A & Chatterjee SS, Oral bioavi­ spair in rats : a new model sensitive to an tidepressant treat­ lability of hyperforin from Hypericum extracts in rats and ments, Eur J Pharmacal, 47 ( 1978) 379 human volunteers, Pharmacopsychiat, 31 (1998) 36. 13 Nahrstedt A & Butterweck V, Biologically active and other 8 Laakmann G, Schule C, Baghai T & Kieser M, St John's chemical constituents of the herb Hypericum petforatum L wort in mild to moderate depression: the relevance of hyper- Pharmacopsychiat, 30 (1997) (Supplement) 129. .
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