Abstract
The presence of several phytochemicals, namely naphthodianthrones hypericin and pseudohypericin, phloroglucinol derivatives hyperforin and adhyperforin, the phenolic acids as chlorogenic acid, neochlorogenic acid, caffeic acid and 2,4-dihydroxybenzoic acid, the flavonols, hyperoside, isoquercitrin, quercitrin, quercetin, avicularin, rutin, and flavanols (+)-catechin and (−)-epicatechin, as well as biflavonoid amentoflavone was investigated in seven Turkish species of Hypericum from Taeniocarpium and Drosanthe sections. Plants were harvested at flowering, dried at room temperature, dissected into different tissues and assayed for chemical contents by HPLC. All chemicals were detected at various levels depending on species and plant parts. Despite the observed quantitative variation in the chemical content of plant material, it was found that phytochemical profiles of the species from the same section were very similar. The present data could be helpful in selecting the future targets for phytochemical and biological studies as well as enriching our current chemical knowledge about Hypericum species. Such kind of data could also be useful for elucidation of the chemotaxonomical relationships among the sections of Hypericum genus.
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Barros FMC, Ccana-Ccapatinta GV, Meirelles GC, Nunes JM, Cargnin ST, Sakamoto S, Bordignon S, del Carpio C, Crockett SL, von Poser GL (2013) Determination of phenolic compounds in flowers of Hypericum species native to South Brazil and Peruvian Páramos. Plant Syst Evol (in press)
Baytop T (1999) Therapy with medicinal plants in Turkey, plants from Guttiferae family. Istanbul University Press, İstanbul, pp 66–167
Bingol U, Cosge B, Gurbuz B (2011) Hypericum species in flora of Turkey. In: Odabas MS, Cirak C (Eds) Hypericum. Medicinal and aromatic plant science and biotechnology, vol 5 (Special Issue 1), pp 86–90
Cirak C (2006) Hypericin in Hypericum lydium Boiss. growing in Turkey. Biochem Syst Ecol 34:897–899
Cirak C, Saglam B, Ayan AK, Kevseroğlu K (2006) Morphogenetic and diurnal variation of hypericin in some Hypericum species from Turkey during the course of ontogenesis. Biochem Syst Ecol 34:1–13
Cirak C, Radusiene J, Sağlam B, Janulis V (2007a) Variation of bioactive substances and morphological traits in Hypericum perforatum populations from Northern Turkey. Biochem Syst Ecol 35:403–409
Cirak C, Radusiene J, Janulis V, Ivanauskas L (2007b) Variation of bioactive secondary metabolites in Hypericum origanifolium during its phenological cycle. Acta Physiol Plant 29:197–203
Cirak C, Radusiene J, Sağlam B (2008) Variation of bioactive substances in Hypericum montbretii during plant growth. Nat Prod Res 22:246–252
Cirak C, Radusiene J, Janulis V, Ivanauskas L (2010) Secondary metabolites of Hypericum confertum and their possible chemotaxonomic significance. Nat Product Commun 5:897–898
Cirak C, Radusiene J, Stanius Z, Camas N, Caliskan O, Odabas MS (2012) Secondary metabolites of Hypericum orientale L. growing in Turkey: variation among populations and plant parts. Acta Physiol Plant 34:1313–1320
Crockett SL, Robson NKB (2011) Taxonomy and chemotaxonomy of the genus Hypericum. In: Odabas MS, Cirak C (eds) Hypericum. Medicinal and aromatic plant science and biotechnology, vol 5 (Special Issue 1), pp 1–13
Crockett SL, Wenzig EM, Kunert O, Bauer R (2008) Anti-inflammatory phloroglucinol derivatives from Hypericum empetrifolium. Phytochem Lett 1:37–43
Davis PH (1988) Flora of Turkey and the East Aegean Islands. Edinburgh University Press, Edinburgh
Demirci B, Baser KHC, Crockett SL, Khan IA (2005) Analysis of the volatile constituents of Asian Hypericum L. (Clusiaceae, Hyperidoideae) species. J Essent Oil Res 17:659–663
Ferraz ABF, Schripsema J, Pohlmann AR, von Poser GL (2002a) Uliginosin B from Hypericum myrianthum. Biochem Syst Ecol 30:989–991
Ferraz A, Bordignon S, Mans DRA, Schimitt A, Ravazzolo AP, von Poser GL (2002b) Screening for the presence of hypericins in Southern Brazilian species of Hypericum. Pharm Biol 40:294–297
Fiebich BL, Knörle R, Apel K, Kammler T, Weiss G (2011) Pharmacological studies in an herbal drug combination of St. John’s wort (Hypericum perforatum) and passion flower (Passiflora incarnata): in vitro and in vivo evidence of synergy between Hypericum and Passiflora in antidepressant pharmacological models. Fitoterapia 82:474–480
Hosni K, Msaada K, Taarit MB, Marzouk B (2011) Phenological variations of secondary metabolites from Hypericum triquetrifolium Turra. Biochem Syst Ecol 39:43–50
Kasper S, Caraci F, Forti B, Drago F, Aguglia E (2010) Efficacy and tolerability of Hypericum extract for the treatment of mild to moderate depression. Eur Neuropsychopharm 20:74–765
Kazlauskas S, Bagdonaite E (2004) Quantitative analysis of active substances in St. John’s wort (Hypericum perforatum L.) by the high performance liquid chromatography method. Medicina (Kaunas) 40:975–981
Kitanov GM (2001) Hypericin and pseudohypericin in some Hypericum species. Biochem Syst Ecol 29:171–178
Lu HF, Shen ZG, Li JYH, Hu ZH (2001) The patterns of secretory structure and their relation to hypericin content in Hypericum. Acta Bot Sin 43:1085–1088
Mathis C, Ourisson G (1963) Etude chimio-taxonomique du genre Hypericum. I. Repartition de hypericine. Phytochemistry 2:157–171
Nahrstedt A, Butterweck V (2010) Lessons learned from herbal medicinal products: the example of St. John’s wort. J Nat Prod 73:1015–1021
Nor C, Bernardi APM, Haas JS, Schripsema J, Rech SB, von Poser GL (2008) Phenolic constituents of Hypericum flowers. Nat Prod Commun 3:237–240
Nunes JM, Pinto PS, Bordignon SAL, Rech SB, von Poser GL (2010) Phenolic compounds in Hypericum species from the Trigynobrathys section. Biochem Syst Ecol 38:224–228
Pharm. Eur. (2010) Directorate for the quality of medicine. European Pharmacopoeia, 7th edn. Council of Europe, Strasbourg, pp 1241–1244
Robson NKB (1977) Guttiferales 109 Guttiferae (Clusiaceae). In: Tutin TG, Heywood WH, Burges NA, Moore DM, Valentine DH, Walters SM, Webb DA. Flora Europa, Vol 2. Cambridge University Press, Cambridge, pp 261–269
Saddiqe Z, Naeem I, Maimoona A (2010) A review of the antibacterial activity of Hypericum perforatum L. J Ethnopharmacol 131:511–521
Schmidt S, Jürgenliemk G, Skaltsa H, Heilmann J (2012) Phloroglucinol derivatives from Hypericum empetrifolium with antiproliferative activity on endothelial cells. Phytochemistry 77:218–225
Smelcerovic A, Spiteller M, Ligon AP, Smelcerovic Z, Raabe N (2007) Essential oil composition of Hypericum L. species from Southeastern Serbia and their chemotaxonomy. Biochem Syst Ecol 35:99–113
Smelcerovic A, Zuehlke S, Spiteller M, Raabe N, Özen T (2008) Phenolic constituents of 17 Hypericum species from Turkey. Biochem Syst Ecol 36:316–319
Spiteller M, Özen T, Smelcerovic A, Zuehlke S, Mimica-Dukić N (2008) Phenolic constituents and the in vitro antioxidant activity of the flowers of Hypericum venustum. Fitoterapia 79:191–193
Stein AC, Viana AF, Müller LG, Nunes JM, Stolz ED, do Rego J, Costentin J, von Poser GL, Rates SMK (2012) Uliginosin B, a phloroglucinol derivative from Hypericum polyanthemum: a promising new molecular pattern for the development of antidepressant drugs. Beh Brain Res 228:66–73
Wolfender JL (2009) HPLC in natural product analysis: the detection issue. Planta Med 75:719–734
Zheng M, Fan Y, Shi D, Liu C (2013) Antidepressant-like effect of flavonoids extracted from Apocynum venetum leaves on brain monoamine levels and dopaminergic system. J Ethnopharmacol 147:108–113
Acknowledgment
Authors are grateful to Metropolitan Municipality of Gaziantep, Turkey for the valuable help in sampling the wild plant material.
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Camas, N., Radusiene, J., Ivanauskas, L. et al. Chemical composition of Hypericum species from the Taeniocarpium and Drosanthe sections. Plant Syst Evol 300, 953–960 (2014). https://doi.org/10.1007/s00606-013-0934-3
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DOI: https://doi.org/10.1007/s00606-013-0934-3
