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LC-MS and LC-PDA Analysis of Hypericum Empetrifolium and Hypericum Sinaicum Feras Q

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LC-MS and LC-PDA Analysis of Hypericum empetrifolium and Hypericum sinaicum Feras Q. Alalia,*, Khaled Tawahab, and Mohammad Gharaibehc a Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al Isra Private University, P. O. Box 22, 33, Amman 11622, Jordan. E-mail: [email protected] b Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Jordan, Amman 11942, Jordan c Department of Natural Resources and Environment, Faculty of Agriculture, Jordan University of Science and Technology, P. O. Box 3030, Irbid 22110, Jordan * Author for correspondence and reprint requests Z. Naturforsch. 64 c, 476 – 482 (2009); received February 25/March 26, 2009 Within the framework of our continuous efforts to explore Hypericum species from Jor- dan, we report the analysis of the major active metabolites, naphthodianthrones and phloro- glucinols, in the methanolic extracts of two under-explored Hypericum species; H. empetri- folium Willd. and H. sinaicum Hochst. & Steud. ex Boiss., using LC-(+,–)-ESI-MS (TIC and SIM) and LC-UV/Vis spectroscopy. Based on their LC-UV/Vis profi les, retention times and (+,–)-ESI-MS (TIC and SIM) spectral data, hypericin, protohypericin and pseudohypericin were identifi ed in both of the investigated species. In addition adhyperfi rin was only de- tected in H. empetrifolium, while hyperforin and protopseudohypericin were only detected in H. sinaicum. This is the fi rst report documenting the presence of hypericin, protohypericin, pseudohypericin, protopseudohypericin, and hyperforin in H. sinaicum, and adhyperfi rin in H. empetrifolium. Key words: Hypericum, Naphthodianthrones, Phloroglucinols Introduction species of Hypericum can be identifi ed by: (i) op- posite simple entire exstipulate leaves contain- Hypericum is a genus of about 450 species ing translucent and often black or red glandular of herbs or shrubs belonging to the family Clu- secretions; (ii) fl owers with a 5-merous perianth siaceae, formerly Hypericaceae. The genus grows comprising green (sometimes red-tinged) sepals widely in temperate regions, and is used in tradi- and free yellow (often red-tinged) petals, stamens tional medicinal practices in various parts of the in 3 – 5 bundles or fascicles, and an ovary with 3 – 5 world. All members of the genus may be referred slender styles; and (iii) a capsular fruit containing to as “Saint John’ wort”, though they are also many small cylindrical seeds (Robson, 2003). commonly just called Hypericums; other names One of the most important and commercially include “Rose of Sharon” and “Tutsan” (Anony- recognized species of the genus Hypericum is H. mous, 2007; Robson, 1990, 2003; Yazaki and Oka- perforatum, commonly known as St. John’s wort. da, 1994). The plant specimen records at National The antidepressant activity of this species is the Center for Agricultural Research and Extension cause for the widespread interest in the study of (NCARE), Ministry of Agriculture, Baq’a, Jor- the Hypericum genus (Hu and Sim, 2000). H. per- dan, showed the presence of seven species of Hy- foratum L. is well known for its profound phar- pericum in Palestine fl ora during 1900 – 1910. In macological activities as mild antidepressant, anx- his list of wild plants in Jordan, Al-Eisawi (1998) iolytic, antiviral, wound healing and antimicrobial reported the presence of 5 species of Hypericum; agent (Barnes et al., 2001; Butterweck et al., 2002; H. hyssopifolium Chaix, H. languinosum Lam., H. Sakar and Tamer, 1990). Prescribed as mild anti- olivieri (Spach) Boiss. H. serpyllifolium Lam., and depressant therapeutic, commercially available H. triquetrifolium Turra. Danin (1997) discovered products of H. perforatum are among the best a population of H. sinaicum Hochst. & Steud. ex selling, most successful and effective herbs in the Boiss. in Jordan at Dana Nature Reserve. Most world. 0939 – 5075/2009/0700 – 0476 $ 06.00 © 2009 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D NNC_7_8_2009.indbC_7_8_2009.indb 476476 113.08.20093.08.2009 117:51:377:51:37 F. Q. Alali et al. · Analysis of Hypericum 477 The Hypericum genus is rich in secondary me- Results and Discussion tabolites, many of which are biologically active. Of the main constituents are naphthodianthrones The investigation benefi tted from the available (hypericin, pseudohypericin, protohypericin, and literature on spectral data and chromatographic protopseudohypericin), phloroglucinols (hyper- elution patterns of phloroglucinols and naph- forin, adhyperforin, hyperfi rin, and adhyperfi rin), thodianthrones (Fuzzati et al., 2001; Tolonen et and a broad range of fl avonoids (e.g., hyperoside al., 2002; Wolfender et al., 2003). Thus, LC-(+,–)- and rutin) (Nahrstedt and Butterweck, 1997). The ESI-MS (TIC and SIM) and LC-UV data were antidepressant activity of H. perforatum was fi rst utilized in an integrative manner to confi rm the attributed to the naphthodianthrones. Recent identity of these compounds in the crude meth- studies revealed that the phloroglucinol hyper- anolic extracts. forin and its derivative adhyperforin inhibit vari- A hypericin reference standard was used to de- ous neurotransmitter receptors (Butterweck et al., velop the optimum chromatographic separation 2001; Chatterjee et al., 1998; Laakmann et al., 1998; conditions. A neutral mobile phase was used to Meruelo et al., 1988; Muller et al., 1998, 2001). able the switch between the positive and nega- The objective of the present study was to in- tive ionization modes simultaneously. The condi- vestigate, at the analytical level, the methanolic tions were optimized for resolution and response extracts of two unexplored Hypericum species of as outlined in the experimental section. The to- Jordanian origin, namely H. empetrifolium Willd. tal run time was 35 min, with a retention time of and H. sinaicum Hochst. & Steud. ex Boiss., for 16.1 min for hypericin. their major secondary metabolites, mainly phlo- The methanolic extract of the total aerial parts roglucinols and naphthodianthrones using liquid of H. empetrifolium and H. sinaicum were ana- chromatography-electrospray mass spectrometry lyzed for the presence of phloroglucinols (hyper- and liquid chromatography-UV spectroscopy forin, adhyperforin, hyperfi rin, and adhyperfi rin) [LC-(+,–)-ESI-MS (total ion chromatograms, and naphthodianthrones (hypericin, pseudohyper- TIC, and selected ion monitoring, SIM) and LC- icin, protohypericin, and protopseudohypericin) UV]. Although there were limited preliminary using LC-ESI-MS and LC-UV. LC-MS full scan phytochemical and analytical studies, none of the TICs, scanning m/z 50 – 1000, were fi rst acquired abovementioned species has been investigated in both positive and negative ionization modes. previously for bioactive constituents using LC- This was followed by positive and negative SIM ESI-MS and LC-UV/PDA (Crockett et al., 2007; analyses. SIM was utilized in compounds’ detec- Kitanov, 2001; Rezanka and Sigler, 2007; Xeno- tion in order to overcome the low sensitivity of phontos et al., 2007). the TIC observed. The following naphthodian- H. empetrifolium and H. sinaicum grow wild in throne molecular ions, [M-H]–, were monitored the northern part of Jordan at Ramtha, Ajloun and in the negative ionization mode: hypericin, m/z Irbid. H. sinaicum is 10 – 30 cm high, altogether 503; pseudohypericin, m/z 519; protohypericin, slightly pubescent. Flowers are few in a terminal m/z 505; and protopseudohypericin, m/z 521. The corymbose panicle. The plant is toxic to livestock negative ionization mode was found to be highly (Batanouny, 1999). H. empetrifolium, also called sensitive for this class of phenolic compounds. Dwarf Hypericum, has deep yellow fl owers in late On the other hand, the positive ionization SIM spring to early summer (Batanouny, 1999). mode was used to monitor the following phloro- Based on their UV profi les, retention times and glucinol molecular ions, [M+H]+: hyperforin; m/z (+,–)-ESI (TIC and SIM) mass spectral data, hy- 537; adhyperforin, m/z 551; hyperfi rin, m/z 469; pericin, protohypericin and pseudohypericin were and adhyperfi rin, m/z 483. Compared to TIC, the identifi ed in both of the investigated Hypericum SIM sensitivity was signifi cantly higher for both species; while adhyperfi rin was only detected in investigated chemical classes. Fig. 1 shows typical H. empetrifolium, hyperforin and protopseudohy- stacked (+,–)-ESI LC-MS TIC chromatograms of pericin were only detected in H. sinaicum. This the methanolic extracts of the aerial parts of H. is the fi rst report documenting the presence of empetrifolium and H. sinaicum. Table I summa- hypericin, protohypericin, pseudohypericin, pro- rizes the retention times, UVmax data, and the mo- topseudohypericin, and hyperforin in H. sinaicum, lecular ions of the identifi ed compounds. By ana- and adhyperfi rin in H. empetrifolium. lyzing the LC-UV and mass spectral data and by NNC_7_8_2009.indbC_7_8_2009.indb 477477 113.08.20093.08.2009 117:51:377:51:37 478 F. Q. Alali et al. · Analysis of Hypericum A 5 6 1 2 7 13 3 8 9 10 11 12 14 15 16 5 10 15 20 25 30 Time [min] B 3 1 2 4 6 8 9 5 7 10 5 10 15 20 25 30 Time [min] Fig. 1. Stacked (+,–)-ESI TIC chromatograms of (A) H. empetrifolium and (B) H. sinaicum. Table I. Retention times and mass spectral data of the (+)- and (-)-ESI TIC and (+)- and (-)-SIM chromatographic peaks. Plant tR [min] UVmax [nm] Molecular ion Compound – H. empetrifolium 16.1 288, 325, 465, 580 503.2 [M-H] OH O OH H. sinaicum HO HO OH O OH Hypericin (1) – H. empetrifolium 4.6 288, 325, 465, 580 519.3 [M-H] OH O OH H. sinaicum OH HO HO OH O OH Pseudohypericin (2) – H. empetrifolium 14.1 285, 375, 530, 590 505.2 [M-H] OH O OH H. sinaicum HO HO OH O OH Protohypericin (3) NNC_7_8_2009.indbC_7_8_2009.indb 478478 113.08.20093.08.2009 117:51:377:51:37 F. Q. Alali et al. · Analysis of Hypericum 479 Plant tR [min] UVmax [nm] Molecular ion Compound – H. sinaicum 3.2 285, 375, 550 521.3 [M-H] OH O OH OH HO HO OH O OH Protopseudohypericin (4) H.
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  • Antidepressant Activity of Hyperforin Conjugates of the St.John's Wort, Hypericum Perforatum Linn.: an Experimental Study

    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.