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The chemistry, pharmacology, and toxicology of the biologically active constituents of the herb Hypericum perforatum L

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Abstract

St. John's wort (Hypericum perforatum) has been used as a medical herb for over 2000 years. Overthe past two decades, its application as a standardized plant extract for treating depression hasundergone rigorous scientific investigation, and its effectiveness has been shown in studiescomparing it with other commonly used antidepressants and placebos. Safety and tolerability studieshave revealed that Hypericum preparations have better safety and tolerability profiles than syntheticantidepressants. The indications for St. John's wort preparations are mild or moderate depression.The mechanism of the antidepressant action of Hypericum extract is not fully known. The view ofthe chemical composition and pharmaceutical a toxicological properties of biologically activesubstances of Hypericum perforatum is the main purpose of this paper.

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... 14,15,47,48 Flavonoids have exhibited activity against cancer and influenza virus. 15,17 High-performance liquid chromatography (HPLC), linked with UV detectors, is a routine technique in most laboratories for chemical separation and detection. HPLC is also the preferred separation technology for the isolation of nonvolatile, often polar, and unstable components present in natural products. ...
... It is also noteworthy that the main constituents in the St. John's wort extracts, especially hypericins, may be retained by some cartridges in the filter during the filtration process. 17,20 Hypericin and pseudohypericin are substantially insoluble in water at ambient temperature and can only be obtained with less than 40% yield at higher temperatures. 4,17−19 When prepared by the tea method, the extract contains very little amounts of hyperforin. ...
... 19,25 The concentration of chlorogenic acid, which has been detected in St. John's wort, is below 1%. 17 Characterization of Extracts with Standards Using HPLC. In this series of measurements (Figures 4 and 5), the extracts, standards, and extracts spiked with standards were measured under the same conditions. ...
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Hypericum perforatum Linn (St. John's wort) is a popular and widespread medicine in Syria, which is used for a wide range of conditions, including gastrointestinal diseases, heart disease, skin diseases, and psychological disorders. This widespread use prompted us to identify the main compounds of this plant from Syria that are responsible for its medicinal properties, especially since its components differ between countries according to the nature of the soil, climate, and altitude. This is, to the best of our knowledge, the first report in which St. John's wort, a plant native to Syria, is extracted using different solvents and its most important compounds are identified. In this study, the dried above-ground parts, i.e., leaves, stem, petals, and flowers, were extracted using different solvents (water, ethanol, methanol, and acetone) and extraction protocols. By increasing the polarity of the solvent, higher yields were obtained, indicating that mainly hydrophobic compounds were extracted. Therefore, we conclude that extraction using the tea method or using a mixture of water and organic solvents resulted in higher yields compared with pure organic solvents or continuous boiling with water for long periods. The obtained extracts were analyzed using high-performance liquid chromatography equipped with a diode array detector (HPLC-DAD), coupled with UV-visible spectrophotometry at a full spectrum (200-800 nm). The HPLC spectra of the extracts were almost identical at three wavelengths (260 nm for phloroglucinols (hyperforin and derivates), 590 nm for naphthodianthrones (hypericins), and 350 nm for other flavonols, flavones, and caffeoylquinic acids), with differences observed only in the intensity of the peaks. This indicates that the same compounds were obtained using different solvents, but in different amounts. Five standards (chlorogenic acid, quercetin, quercitrin hydrate, hyperoside, and hypericin) were used, and a comparison with retention times and ultraviolet (UV) spectra reported in the literature was performed to identify 10 compounds in these extracts: hyperforin, adhyperforin, hypericin, rutin, quercetin, quercitrin, quercitrin hydrate, hyperoside, biapigenin, and chlorogenic acid. Although the European Pharmacopoeia still describes ultraviolet spectroscopy as a method for determining the quantity of Hyperici herba, interference from other metabolites can occur. Combined HPLC-DAD and electrospray ionization-mass spectrometry (LC-ESI-MS) in the positive mode have therefore also been used to confirm the presence of these compounds in the extracts by correlating known masses with the identified masses or through characteristic fragmentation patterns. Total phenolic contents of the extracts were determined by the Folin-Ciocalteu assay, and antioxidant activity was evaluated as free radical scavenging capacity using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. The results indicate that the aqueous extracts prepared by the tea method gave the highest total phenols, while the pure organic solvents gave very low phenols. Also, the extracts that contain the largest amount of phenols gave lower IC50 values or higher antioxidant activity than that of others.
... John's wort) is one of the most important medicinal plant worldwide. It is used for its medicinal properties from past 2000 years (Patocka 2003;. It is used to treat diseases like depression, inflammation, leukaemia etc. (Karioti and Bilia 2010). ...
... These compounds are found commonly in the reproductive parts of the plant, particularly in mature fruits and in lesser amounts in flowers as well. It is reported that hyperforin normally exists in 2-10 fold higher amounts as compared to adhyperforin (Greeson et al. 2001;Patocka 2003). The biosynthetic intermediates of these compounds like hyperfirin and adhyperfirin as well as their homologues secohyperforin and secoadhyperforin have also been detected and reported as phytoconstituents in H. perforatum (Beerhues 2006;Holscher et al. 2009). ...
... These include tannins (ranging from 3 to 16%), xanthones (1.28 mg/100 g), phenolic compounds (caffeic acid, chlorogenic acid, and p-coumaric acid), and hyperfolin. Additional compounds include, to a lesser extent, acids (nicotinic, myristic, palmitic, and stearic), carotenoids, choline, pectin, hydrocarbons, and long-chain alcohols (Greeson et al. 2001;DerMarderosian and Beutler 2002;Patocka 2003). Several amino acids that have been isolated from the herb include cysteine, glutamine, leucine, lysine, and GABA (c-aminobutyric acid) (Patocka 2003). ...
... H. perforatum is one of the most widely studied medicinal plants because of its chemical composition and pharmacological properties. The bioactive compounds present in H. perforatum can be mainly classified in different groups such as (1) phloroglucinols; (2) naphthodianthrones; (3) flavonoids, tannins, and related compounds; (4) phenylpropanoids and other simple phenolic compounds; (5) xanthones; and (6) volatile compounds (Ganzera et al., 2002;Hansen et al., 1999;Jurgenliemk and Nahrstedt, 2002;Nahrstedt and Butterweck, 1997;Patocka, 2003;Silva et al., 2005;Tatsis et al., 2007;Wurglics and Schubert-Zsilavecz, 2006;Zou et al., 2004). A detailed list of these compounds is given in Table 3.40.3. ...
... Chlorogenic acid Nahrstedt and Butterweck (1997), Patocka (2003), Silva et al. (2005), and Tatsis et al. (2007) Neochlorogenic acid Jurgenliemk and Nahrstedt (2002), and Silva et al. (2005) Chryptochlorogenic acid Jurgenliemk and Nahrstedt (2002) 3-O-(Z)-P-coumaroylquinic acid Jurgenliemk and Nahrstedt (2002) 3-O-(E)-P-coumaroylquinic acid Jurgenliemk and Nahrstedt (2002), and Tatsis et al. (2007) Caffeic acid Barnes et al. (2001) p-Coumaric acid Barnes et al. (2001) Ferulic acid Barnes et al. (2001) p-Hydroxybenzoic acid Barnes et al. (2001) Vanillic acid Barnes et al. (2001) Protocatechuic acid Jurgenliemk and Nahrstedt (2002) (e) Xanthones ...
... Jurgenliemk and Nahrstedt (2002) 1,3,6,7-Tetrahydroxyxanthone Patocka (2003), and Jurgenliemk and Nahrstedt (2002 ...
Chapter
Hypericum perforatum L. also known as St John’s wort (SJW) is an effective dietary supplement for treating various nervous system related disorders. It overcome anxiety, mild to moderate depression, mood disorders and stress due to the presence of vast number of bioactive compounds. As such, hypericin and hyperforin are the major compounds along with other less abundant compounds such as flavonoids, biflavonoids, phloroglucinols, napthodianthrones, xanthones, proanthocyanidins, phenolic acid, etc. Beside its effect over nervous system, SJW also effective against cancer, oxidative stress, inflammation and microbial infections. It is one of the high selling natural supplements in USA and other western countries. However, interaction of SJW with other medicines such as warfarin, phenoprocumon, cyclosporine, oral contraceptives, theophylline, digoxin, indinavir and lamivudine have been reported and thus cautions must be taken while using these medicines along with SJW.
... MedPress Publications LLC symptom disorder, stress and inflammation [64,65,66,67]. In addition to hypericin and hyperforin, which are the major bioactive compounds, several flavonoids, phloroglucinols, napthodianthrones, xanthones and proanthocyanidins have been also identified as active principles in the plant [64,66]. ...
... MedPress Publications LLC symptom disorder, stress and inflammation [64,65,66,67]. In addition to hypericin and hyperforin, which are the major bioactive compounds, several flavonoids, phloroglucinols, napthodianthrones, xanthones and proanthocyanidins have been also identified as active principles in the plant [64,66]. Notably therefore, St. John's wort has gained competing status as the only herbal antidepressant alternative to standard antidepressant drugs [68]. ...
Article
In recent decades, physical inactivity, work pressure and stress as well as change in food habits have led to the deterioration of public health.
... Hypericum perforatum L. (HP) is a perennial herbaceous plant native to western Asia, North Africa, and Europe, commonly known as St. John's wort or millepertuis [12]. It is used as a medicinal herb to treat a variety of diseases, including skin diseases, anxiety, and depression [12][13][14]. ...
... Hypericum perforatum L. (HP) is a perennial herbaceous plant native to western Asia, North Africa, and Europe, commonly known as St. John's wort or millepertuis [12]. It is used as a medicinal herb to treat a variety of diseases, including skin diseases, anxiety, and depression [12][13][14]. It is also characterized by potent antimicrobial, antiviral, anti-inflammatory, neuroprotective, wound healing, antinociceptive, and cytotoxic activities [15]. ...
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Hypericum perforatum (HP) is characterized by potent medicinal activity. However, the poor water solubility of many HP constituents limits their therapeutic effectiveness. Self-nanoemulsifying self-nanosuspension loaded with HP (HP.SNESNS) was formulated to improve the bioefficacy of HP. It was prepared using 10% triacetin, 57% Tween 20, and 33% PEG 400 and then incorporated with HP extract (100 mg/mL). HP.SNESNS demonstrated a bimodal size distribution (258.65 ± 29.35 and 9.08 ± 0.01 nm) corresponding to nanosuspension and nanoemulsion, respectively, a zeta potential of -8.03 mV, and an enhanced dissolution profile. Compared to the unformulated HP (100 mg/kg), HP.SNESNS significantly improved cardiac functions by decreasing the serum myocardial enzymes, nitric oxide (NO), and tumor necrosis factor- α (TNF-α) as well as restoring the heart tissue's normal architecture. Furthermore, it ameliorates anxiety, depressive-like behavior, and cognitive dysfunction by decreasing brain TNF-α, elevating neurotransmitters (norepinephrine and serotonin), and brain-derived neurotrophic factor (BDNF). In addition, HP.SNESNS augmented the immunohistochemical expression of cortical and hippocampal glial fibrillary acidic protein (GFAP) levels while downregulating the cortical Bcl-2-associated X protein (Bax) expression levels. Surprisingly, these protective activities were comparable to the HP (300 mg/kg). In conclusion, HP.SNESNS (100 mg/kg) exerted antidepressant and cardioprotective activities in the post-MI depression rat model. Graphical Abstract
... They have been shown to manifest antioxidant effect, the ability to remove free radicals have cardio-protective, antidiabetic, anti-inflammatory, antiallergic, anti-cancer and potential antiviral effects (7). Procyanidins exhibit antioxidant, antiviral, antimicrobial and vasoactive properties (8). The ethereal oil (0.07 -0.25%) of dried flowering stems contains mainly the substances α-pinene and 2-methyloctane (4). ...
... Hypericin and pseudohypericin are practically water insoluble at room temperature, but this can be overcome at higher temperatures. Therefore, St. John's wort infusion may contain almost half of the amount of these two compounds (8). ...
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Spectral analyses of 1% water extracts of fresh and dry Hypericum perforatum L. and 1% dry H. perforatum with colloidal nano silver (NSPs) 30 ppm were conducted. The nano silver is standardised and patented by the Swiss company Evodrop. Non-equliblrium energy spectrum (NES) and Differential non-equliblrium energy spectrum (DNES) methods were used for the spectral analysis. A comparative analysis of 1% extracts of fresh and dry H. perforatum was performed in order to determine the local extremums for effects of nerve tissue conductivity at (-0.1112) eV, anti-inflammatory (-0.1212) eV, anti-tumor effects (-0.1387) eV. The results showed stimulating effect on the nervous system and improvement of nerve conduction (local extremums E=-0.1112 eV)(?=11.15 ?m) (?=897 cm-1), as well as anti-inflammatory effect (E = -0.1212 eV)( ?=10.23 ?m) (?=978 cm-1) and inhibition of development of tumor cells at a molecular level (E=-0.1387 eV) (?=8.95 ?m) (?=1117 cm-1). It was found that clusters of 16 and 15 water molecules are formed in the water herbal extracts of fresh H. perforatum and of dry H. perforatum with AgNPs 30 ppm. The fresh plant showed better results then the dry one. The addition of colloidal nano silver 30 ppm led to better results of the drug.
... Due to its wide range of pharmacological activities, including antidepressant, antiviral, and antibacterial effects, Hypericum perforatum is one of the most consumed medicinal plants in the world (Linde et al., 1996), and its extracts are extensively used as phytopharmaceuticals and nutraceuticals. The active constituents of H. perforatum have been reviewed by several papers (Patočka, 2003;Napoli et al., 2018); the identified compounds belong to the chemical families of naphthodianthrones ( . 1F), along with a number of "minor" compounds. ...
... 1F), along with a number of "minor" compounds. Naphthodianthrones, including hypericin and related compounds (pseudohypericin, protohypericin and protopseudohypericin) are typical of the genus Hypericum (Patočka, 2003), and represent the best known and most studied components of H. perforatum extracts. Although hypericins were found in many Hypericum species, they are more abundant in H. perforatum (Napoli et al., 2018), that for commercial purposes, should contain not less than 0.08 % hypericins calculated as hypericin (WHO, 2002). ...
Article
St John’s Wort (Hypericum perforatum L.; Hypericaceae) is a perennial medicinal herb widespread and largely used in folk medicine inside the Mediterranean basin. Many bioactive compounds have been identified within its extracts. Under a pharmacological point of view, the most important of them belong to the chemical classes of naphthodianthrones, phloroglucinols and polyphenols. Many factors have been claimed responsible for the phytochemical variability in Hypericum perforatum, such as genotype, geographical origin, harvesting stage and age of the plants. Yet, when harvested plant material is addressed to the industry, the standardization of the active ingredients over cultivation years is a crucial issue. With the aim to detect the stability over years and genotypes of several bioactive Hypericum compounds, seven Hypericum biotypes retrieved from different Italian geographical areas were cultivated in 2015 and 2016, and their aerial flowering parts were analyzed. Naphthodianthrones (hypericin and its biosynthetic precursors), phloroglucinols (hyperforin and adhyperforin), and main polyphenols were determined by HPLC-DAD analysis. The results were statistically evaluated through ANOVA, and the stability over cultivation years of the tested genotypes was assessed. In rather all the examined metabolites, the ANOVA revealed a remarkable effect of both factors “year” (Y) and “provenance” (P), but the occurrence of significant “Y x P” interactions evidenced that the effect of climatic variability was often different according to the genotype. The evaluation of the stability level between years evidenced that only one biotype out of seven exhibited constantly higher-than-average amounts of rather all identified metabolites.
... Chemical composition H. perforatum aerial parts contain several bioactive compounds classes, namely: naphthodianthrone (0.03-0.3% hypericin and pseudohypericin and their derivatives), phloroglucinol (2.0-4.5% hyperforin, and its precursors and derivatives), 2-4% flavonoids (quercetin, myricetin, luteolin, kaempferol, catechin, epicatechin, rutin, hyperoside, quercitrin, isoquercitrin, kaempferol 3-O-glucoside, kaempferol 3rutinoside), phenolic acids (chlorogenic, neochlorogenic, caffeic, shikimic, p-coumaric and ferulic acids), 0.05-0.9% essential oil, xanthones, alkaloids, proanthocyanidins (procyanidin B2) and tannins (Cretu et al., 2011;Greeson et al., 2001;Ionescu et al., 2018a;Ionescu et al., 2018b;Patočka, 2003;Saddiqe et al., 2010;Stanescu et al., 2014;Tebrencu et al., 2018c;Tebrencu et al., 2018d;Velingkar et al., 2017;WHO, 2010;Wirz, 2000;Yousuf et al., 2012). Other constituents include: acids (isovalerianic, nicotinic, myristic, palmitic, stearic), carotenoids, choline, nicotinamide, pectin, β-sitosterol, straight-chain saturated hydrocarbons (C16, C30) and alcohols . ...
... The extracts, fractions and isolated compounds from H. perforatum have been reported to have antidepressant, antiparkinsonian, anticonvulsant, anxiolytic, antioxidant, antibacterial, antifungal, antiviral, wound healing, anti-inflammatory, analgesic, anti-diabetic, antiangiogenic and anticancer activities (Asgarpanah, 2012;Butterweck et al., 2001;Gruenwald et al., 2000;Patočka, 2003;Shrivastava & Dwivedi, 2015;Silva et al., 2005;Velingkar et al., 2017). (Saddiqe et al., 2010;Yousuf et al., 2012). ...
... Since conventional methods are time-consuming and yield of fieldgrown plants is affected by physiological and environmental factors, effective biotechnological methods have been attempted for the improvement of specific secondary metabolite production under controlled conditions [8]. In vitro cell and organ cultures were mainly exploited for the production of target compounds such as naphthodianthrones (hypericins) and acylphloroglucinols (hyperforin), which contribute to the antidepressant activity of Hypericum plant extracts [9,10]. The development of novel technologies of cell culture and molecular biology, such as cell line selection, cell immobilization, permeabilization, precursor feeding, product secretion, biotransformation, metabolic engineering, bioreactor engineering, synthetic biology, and elicitation, allow many ways to improve secondary metabolite production [11,12]. ...
... Hypericum spp. are known worldwide for traditional and modern medicinal uses in rural and ethnic communities of different countries and have been reported as an antitumor, antidepressant, antiviral, antimicrobial, anti-inflammatory, and healing agents [9,[20][21][22][23]. The vital compounds imparting medicinal properties to Hypericum spp. ...
Chapter
The rich phytochemical profile of Hypericum species and the presence of unique compounds, such as hypericins and hyperforin, make them medicinally valuable worldwide. Among Hypericum spp., H. perforatum L. remains the most investigated and exploited species for specific compound production, while others have been surveyed mainly as a source of novel drugs. The main focus of Hypericum biotechnology is the manipulation of secondary metabolism and development of environmentally sustainable and economically viable culture systems toward the efficient production of target and novel secondary metabolites. Since specific compounds accumulate mainly in the aerial parts of Hypericum plants, large-scale shoot cultures are viewed as superior alternative for the production of these compounds under controlled conditions to their extraction from wild- or greenhouse-grown plants or their chemical synthesis. This chapter describes how media culture composition, culture conditions, elicitors, and other critical parameters influence the behavior of Hypericum spp. in shoot cultures and how optimization of these factors could allow improvements in secondary metabolite-related production and discovery of novel drugs.
... Farmakopesi'ne kayıtlıdır [5][6][7]. ...
... Uzun yıllardır yapılan çalışmalar sonucunda H. perforatum bitkisinin kimyasal bileşimi aydınlatılmış; bitkinin, naftodiantron türevleri (hiperisin, psödohiperisin), flavonoitler (rutin, hiperozit, izokersitrin, kersitrin, luteolin, kempferol, mirsetin, amentoflavon ve I3, II8 biapigenin), floroglusinoller (hiperforin, adhiperforin), biflavonlar, prosiyanidinler, ksanton türevleri, tanenler, uçucu yağ bileşikleri, fenolik asit türevleri, amino asitler, ayrıca; organik asitler, peptidler, polisakkaritler gibi hidrofilik maddeler ile bazı lipofilik maddeleri taşıdığı saptanmıştır [6,10,12,13]. ...
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ÖZ Amaç: Ülkemizde, halk arasında tedavi amacıyla kullanılan bitkisel droglar genellikle aktarlardan temin edilmektedir. Aktarlarda satılan drogların kalitesi ve güvenilirliği uzun yıllardır tartışılmaktadır. Bu çalışma ile önemli tıbbi bitkilerimizden biri olan ve halk arasında yaygın olarak kullanılan Hypericum perforatum türünün İstanbul aktarlarından satın alınan örnekleri incelenmiştir. Gereç ve Yöntem: Sarı Kantaron adı ile satılan droglar, İstanbul’da faaliyet gösteren, rastgele seçilmiş 12 farklı aktardan temin edilmiştir. Bitkinin toplanan kısmının (drog) ve toplanma zamanının kontrolü makroskobik ve mikroskobik incelemelerle; saklama koşullarının uygunluğu ise mikrobiyolojik test ile araştırılmıştır. Drogların kül ve nem miktarı, total antioksidan statü (TAS) ve total oksidan statü (TOS) değerleri, oksidatif stres indeksi (OSI), mineral ve ağır metal madde düzeyleri tespit edilmiştir. Droglardan hazırlanan metanol ekstrelerinin hiperisin içeriği Yüksek Performanslı Sıvı Kromatografisi (YPSK) ile analiz edilmiştir. Sonuç ve Tartışma: Bu çalışma ile örneklerin çoğunun gözle görülebilen kirlilikler ile kontamine olduğu, 6 tanesinin hiperisin içermediği, 2 tanesinin çok yüksek oranda alüminyum (Al) içerdiği belirlenmiştir. Sonuç olarak tıbbi bitkilerin gerekli denetimlere tabi tutulmadan aktarlarda satılmasının halk sağlığı açısından uygun olmadığı bir kez daha anlaşılmıştır. Mevcut bu durumun önüne geçilmesi, halkın doğru ve standart kalitede droglara ulaşabilmesi sağlanmalıdır. Anahtar Kelimeler: ağır metal, aktarlar, halk sağlığı, hiperisin, Hypericum perforatum ***ABSTRACT In our country, herbal drugs used for medical purposes by the folk are generally purchased from the herbal stores. The quality and reliability of the plants sold in the herbal stores have been discussed for many years. The present study aims to investigate samples of Hypericum perforatum, which is one of the important medicinal plants and widely used by the folk. The drugs sold as “St John’s Wort” were purchased from 12 different herbal stores which were randomly chosen in Istanbul. Quality control of the collected part and collection time of the plant were examined by using macroscopic and microscopic methods. The suitability of the plant storage conditions were investigated by microbiological test. The ash and moisture contents, total antioxidant status (TAS), total oxidant status (TOS), oxidative stress index (OSI), mineral and heavy metal levels of the plant were determined. Hypericin contents of the methanol extracts prepared from the plant samples were analyzed by High Performance Liquid Chromatography (HPLC). Result and Discussion: In this study, it was determined that most of the samples were contaminated by impurities, 6 of them did not contain hypericin, and 2 of them contained high levels of aluminium (Al). As a result, it was once again understood that it might be inconvenient to sell the medicinal plants in the herbal stores unless inspected for public health. Sale of the medicinal plants in herbal stores should be prevented, and it should be ensured that the public can reach the high quality medicinal plants. Keywords: heavy metal, herbalists, hypericin, Hypericum perforatum, public health
... Since conventional methods are time-consuming and yield of fieldgrown plants is affected by physiological and environmental factors, effective biotechnological methods have been attempted for the improvement of specific secondary metabolite production under controlled conditions [8]. In vitro cell and organ cultures were mainly exploited for the production of target compounds such as naphthodianthrones (hypericins) and acylphloroglucinols (hyperforin), which contribute to the antidepressant activity of Hypericum plant extracts [9,10]. The development of novel technologies of cell culture and molecular biology, such as cell line selection, cell immobilization, permeabilization, precursor feeding, product secretion, biotransformation, metabolic engineering, bioreactor engineering, synthetic biology, and elicitation, allow many ways to improve secondary metabolite production [11,12]. ...
... Hypericum spp. are known worldwide for traditional and modern medicinal uses in rural and ethnic communities of different countries and have been reported as an antitumor, antidepressant, antiviral, antimicrobial, anti-inflammatory, and healing agents [9,[20][21][22][23]. The vital compounds imparting medicinal properties to Hypericum spp. ...
... The active compounds of Hypericum perforatum are gathered under six major natural product groups which are naphthodianthrones, phloroglucinols, flavonoids, biflavones, phenylpropanes, and proanthocyanidins. Especially the compounds hypericin and pseudohypericin are concerned to be the biologically active compounds of H.perforatum, and quercetin, which is an aglycone flavonoid, is accepted as active components as well (Patocka, 2003). The nephroprotective activity of H.perforatum has been proven by in-vivo studies (Abd El Motteleb and Abd El Aleem, 2017;Çakır et al., 2017). ...
Article
The purpose of this study is to identify the plant species that are used traditionally as herbal medicines for kidney disorders in both Iraq and Türkiye, as well as to compare their traditional medicine based on the practical use of plants and highlight the same ones. Ethnomedicine is defined as the study or comparison of traditional medicine based on plants` bioactive compounds. Traditional herbal applications for kidney disorders are frequently used among people, as kidneys have a major role in the maintenance of homeostasis of the body, fluid, and electrolyte, and also, have a role to fulfill many metabolic functions. Iraq and Türkiye are homeland for many medicinal plants and it is crucial to understand local medicinal plant uses and their relationship with surrounding areas. To obtain valuable information, approximately 100 ethnobotanical and ethnomedicinal articles were scanned. As a result of this study, it has been found that 9 taxa are used for renal disorders in Iraq only while, 30 taxa are used for kidney diseases in Türkiye only, and 5 taxa were found to be effective against renal diseases in both countries. Furthermore, 22 plant families have been recorded in which Apiaceae (4 taxa), Compositae (8 taxa), Malvaceae (3 taxa) and Lamiaceae (3 taxa) were the most used ones. The fact that the same plant species are used for the same disease in both countries will give us an idea about the development of herbal medicine with these plant species in the future.
... The H. perforatum extracts showed antidepressant, antitumoral, antiviral, antimicrobial and antioxidant activity (Velingkar et al., 2017). The Hypericum species collected around the world have shown to possess different phytochemical composition and biological activities (Patočka, 2003;Çırak et al., 2011;Božin et al., 2013). ...
... The H. perforatum extracts showed antidepressant, antitumoral, antiviral, antimicrobial and antioxidant activity (Velingkar et al., 2017). The Hypericum species collected around the world have shown to possess different phytochemical composition and biological activities (Patočka, 2003;Çırak et al., 2011;Božin et al., 2013). ...
... (Grünwald, 1999;Ng ve Ho, 2017). H. perforatum L. ilaç ve gıda olarak kullanımının yanı sıra tekstil sektöründe kumaş boyamada ve kozmetik sanayide de yaygın olarak kullanılmaktadır (Patocka, 2003). ...
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zet Türkiye'de birçok bölgede doğal olarak yetişen ve sarı kantaron olarak da bilinen Hypericum perforatum L. bitkisi de değerli tıbbi aromatik bir bitkidir. Bu çalışmada, farklı eko-coğrafik özelliklere sahip Bayburt ve Kırklareli lokasyonlarından toplanan H. perforatum L. bitkisinin çiçek, yaprak, sap ve kök kısımlarının antioksidan aktivitelerin belirlenmesi amaçlanmaktadır. Farklı bölgelerde doğal olarak yetişen H. perforatum L. bitki kısımlarının karşılaştırıldığı ilk olma özelliğine sahip bu çalışmada; en yüksek toplam fenolik madde değeri (11.87 mg GAE/g) Kırklareli lokasyonundan toplanan bitki yaprak örneğinde, en düşük değer ise (4.49 mg GAE/g) Bayburt lokasyonundan toplanan bitki sap örneğinde, en yüksek DPPH değeri (SC50 1.734 mg/mL) Bayburt lokasyonundan toplanan bitki kök örneğinde, en düşük değer ise (SC50 0.259 mg/mL) Kırklareli lokasyonundan toplanan bitki yaprak örneğinde, en yüksek FRAP değeri, (216.97 μmol FeSO4.7H2O/g) Kırklareli lokasyonundan toplanan bitki yaprak örneğinde, en düşük FRAP değeri ise (60.42 μmol FeSO4.7H2O/g) Bayburt lokasyonundan toplanan bitki kök örneğinde belirlenmiştir. Antioksidan aktivite değerleri incelendiğinde, Kırklareli ilinde doğal olarak yetişen H. perforatum L. bitkisinin, Bayburt ilinde doğal olarak yetişene kıyasla daha tercih edilebilir olduğu sonucu ortaya çıkmaktadır.. Abstract Hypericum perforatum L., also known as St. John's Wort, which grows naturally in many regions in Turkey, is also a valuable medicinal aromatic plant. In this study, it is aimed to determine the antioxidant activities of the flower, leaf, stem and root parts of H. perforatum L. plant collected from Bayburt and Kırklareli locations with different eco-geographical characteristics. In this study, which is the first to compare the plant parts of H. perforatum L. naturally grown in different regions; The highest total phenolic substance value (11.87 mg GAE/g) in the plant leaf sample collected from Kırklareli location, the lowest value (4.49 mg GAE/g) in the plant stem sample collected from Bayburt location, the highest DPPH value (SC50 1.734 mg/mL) Bayburt location, the lowest value (SC50 0.259 mg/mL) in the plant leaf sample collected from Kırklareli location, the highest FRAP value (216.97 μmol FeSO4.7H2O/g) the lowest FRAP value in the plant leaf sample collected from Kırklareli location (60.42 μmol FeSO4.7H2O/g) was determined in the plant root sample collected from Bayburt location. When the antioxidant activity values are examined, it is concluded that the naturally grown H. perforatum L. plant in Kırklareli is more preferable than the naturally grown plant in Bayburt.
... Hypericum perforatum L. commonly known as St. John's wort, is an elite medicinal plant of Kashmir Himalaya, which has been used by ancient herbalists (locally called as Hakims) since 2000 years ago [1]. H. perforatum depicts remarkable variation in its morphological traits, breeding system and ploidy level [2]. ...
Article
A number of environmental factors such as mean temperature, precipitation, soil characteristics etc. changes with elevational gradient and thereby, affect the morphological pattern of a plant species. Phenotypic attributes of a particular species varies along different altitudes in order to adapt and also to overcome these changeable and stressful conditions. The present study was undertaken to assess the distribution pattern and impact of habitat variability along an elevational gradient on morphology of an important medicinal plant Hypericum perforatum L. growing in the Kashmir Himalaya. Hypericum perforatum L., member of family Hypericaceae, is a perennial herb and distributed in North Western Himalaya. The species exhibited distinct variability and a peculiar trend in morphological traits in response to different environmental conditions along an elevational gradient.
... 42 De mat. med., V, 54. 43 Patocka, 2003. 44 Delatte, 1938 Ya en el siglo XII, Hildegarda de Bingen, 45 monja asceta y visionaria y autora de compendios de botánica y medicina, había escrito: Para uno que es estúpido y tonto y le falta el conocimiento, machaque betónica para sacar su jugo y póngala por la noche encima de todo su pecho. ...
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... In aqueous solution, at room temperature, Hyp is self-aggregating, due to hydrogen bonds between the carbonyl group of one Hyp molecule with the phenol group of another adjacent Hyp molecule. The molecule is soluble in organic solvents, due to its apolar property, determined by the presence of multiple rings (Patocka 2003). In this way, to increase the solubility of Hyp and prevent the formation of aggregates, the addition of compounds capable of modifying its dissolution is indicated (Falk and Schmitzberger 1992). ...
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Considering the multifaceted and increasing application of photodynamic therapy (PDT), in recent years the antimicrobial employment of this therapy has been highlighted, because of the antiviral, antibacterial, antiparasitic, and antifungal activities that have already been demonstrated. In this context, research focussed on antimycological action, especially for treatment of superficial infections, presents promising growth due to the characteristics of these infections that facilitate PDT application as new therapeutic options are needed in the field of medical mycology. Among the more than one hundred classes of photosensitizers the antifungal action of hypericin (Hyp) stands out due to its ability to permeate the lipid membrane and accumulate in different cytoplasmic organelles of eukaryotic cells. In this review, we aim to provide a complete overview of the origin, physicochemical characteristics, and optimal alternative drug deliveries that promote the photodynamic action of Hyp (Hyp-PDT) against fungi. Furthermore, considering the lack of a methodological consensus, we intend to compile the best strategies to guide researchers in the antifungal application of Hyp-PDT. Overall, this review provides a future perspective of new studies and clinical possibilities for the advances of such a technique in the treatment of mycoses in humans.
... Diversified Hypericum species possess antiviral, anti-inflammatory antioxidant, and antibacterial properties [9]. Naphthodianthrones, chlorogenic acid, phloroglucinols, flavonoids, xanthones, proanthocyanidins, phenylpropanes, benzofuran, and benzopyrans are widely reported from this genus [10][11][12][13]. ...
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Purpose: To investigate the vasodilating effect of Hypericum revolutum Vahl (Clusiaceae) in rats. Methods: H. revolutum aerial parts were extracted with methanol. The total methanol extract was fractionated with chloroform to yield fraction I. The remaining aqueous solution was chromatographed on Diaion HP-20 using water, 50 % methanol, and methanol to yield three fractions (II- IV). Total methanol extract and fractions I-IV were applied to phenylephrine-pre-contracted (10 μM) rat aortic rings at doses of 1, 3, and 10 μg/mL. Subsequent decreases in aortic tension were recorded by an isometric force transducer to evaluate the vasodilation. Column chromatography was utilized to separate the active components of the bioactive fraction. Results: Remarkable decreases in aortic tension (p<0.05) revealed that fraction I (3 and 10 μg/mL) produced a vasodilating effect, whereas fractions III and IV did not possess any substantial effect. Vasodilation induced by fraction I was endothelial-dependent because it was significantly (p<0.05) blocked by endothelial denudation. Phytochemical inspection of fraction I led to the isolation of β- sitosterol (1), 1,7-dihydroxyxanthone (euxanthone) (2), and 2,3,4-tirmethoxy xanthone (3). Conclusion: Fraction I of the H. revolutum extract was responsible for its vasodilating effect. This fraction may be used as a possible anti-hypertensive preparation after in vivo testing and successful clinical trials.
... Hypericum species contain a large number of secondary metabolites, including naphrodiantrons, flurogonol derivatives, flavonoids, organic acids, essential oils, amino acids, xanthones, tannins, proxyanidines and other water-soluble components 18,19 . Although Hypericum perforatum has many bioactive compounds in its structure, the most active in terms of pharmacological properties are hyperforin, a phloroglucinol derivative, and hypericin, a naphthodianthron derivative 20 . Hypericin, a colored pigment that gives oil its red color, is the most important component 21 . ...
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Objective: Consumers' preference for products produced with natural additives has accelerated the search for natural substances that are alternative to synthetic materials in cosmetics and food production. The aim of the study is to obtain a herbal cream by using the natural preservative effect of propolis and the moisturizing effect of St. John's wort fixed oil of Hypericum perforatum plant which grows naturally in our country. Material-Method: The chemical content of the obtained propolis ethanolic extract was determined by Liquid Chromatography Mass Spectrometry (LC-MS/MS) analysis. Hypericum perforatum fixed oil was obtained by maceration and the chemical content of the oil was determined by gas chromatography mass spectrometry (GC-MS) analysis. Herbal cream was prepared using PEG400 to facilitate dispersion of Hypericum perforatum oil and propolis extract obtained in water-based cream formulations and to provide a creamy consistency. Microbiological stability tests were carried out with reference to ISO21149, ISO16212, ISO18416, ISO22717 and ISO21150 standards and ISO11930: 2012 standard for challenge test (preservative efficacy tests). Results: The total phenolic content of propolis ethanol extract was determined as 66.096 ± 1.546 mg gallic acid equivalent (GAE) / mL sample, dry weight and flavonoid content as 13.375 ± 0.185 quercetin equivalent (QE) / mL sample. An extract rich in phenolic components such as quercetin, p-coumaric acid, ferulic acid, trans-cinnamic acid, benzoic acid was obtained. Component analysis showed that propolis ethanolic extract could show preservative efficiency. The presence in the GC-MS analysis of Hypericum perforatum oil that it contains fatty acids widely used in the cosmetic and pharmaceutical industry clearly demonstrated that the oil can be used safely in cream formulations. Conclusion: The test results of the creams were prepared using Hypericum perforatum and propolis clearly revealed that the obtained propolis extract provided protective efficacy. The thickener property of PEG400, which is used to ensure homogeneous distribution, reduced the need for an extra thickener additive.
... Dried above-ground parts of H. perforatum, which is rich in bioactive components (Naphthodianthrones, flavonoids, phloroglucinols, antioxidants, tannins, coumarins, xanthones, indoleamines), are used as food additives and medicinal preparation (Murch et al., 2000;Barnes et al., 2001;Kasper et al., 2010). The plant that shows antiviral, antimicrobial, anticancer, and cytotoxic activity thanks to these components is used in the treatment of diabetes, chronic rheumatism, respiratory and digestive system disorders, jaundice, antidepressant, wound healing, and cancer (Duke 1985, Schinazi et al., 1990Agostinis et al., 2002;Patocka 2003;Silva et al., 2005;Gartner et al 2005;Barcaccia et al 2006). In particular, hypericin is effective in antiretroviral, anticancer and cytotoxic activity (Lavie et al., 1995;Schempp, 2002). ...
... Hypericum perforatum (HP)/ St. John's wort is a plant that has been used by humans for the treatment of various diseases for centuries. Hypericin, pseudohypericin, hyperforin, adhyperforin, hyperoside, quercetin, quercitrin, isoquercitrin, rutin, kaempferol, biapigenin and chlorogenic acid which are the main ingredients in plant extract, are important active compounds 2,3 . Studies have shown that some of the active ingredients contained in HP affect apoptosis in the cell4. ...
Article
Objectives: Basal cell carcinoma is the most common malignancy in in the Caucasian race and is a serious health problem with its ever-increasing incidence and high cost. Although the treatment is surgical, some elderly patients do not accept surgical intervention. In this case, non-surgical treatments come into prominence. The Hypericum perforatum (HP) / St. John's Wort plant has been used in the treatment of many diseases for centuries among local people. Here, we aimed to aimed to elucidate the effect and molecular mechanism of the HP plant on BCC cells. Methods: Human BCC cell lines TE 354.T were acquired from ATCC®, then were cultured in Dulbecco's Modified Eagle's Medium. BCC cells were seeded at a concentration of 2x106cells in each flask (n=12). After incubation, while six of the flasks were applied with a 0.8% HP extract and 99.2% medium for 48 hours, no application was made to the control group. The effects of HP on mitochondrial mediated intrinsic and extrinsic apoptotic pathway agents, cell cycle G2 / M checkpoint kinases and inflammatory mediators were investigated in BCC cancer cells. The expression and activities of these mediators in both groups were evaluated by ELISA test. Results: It was determined that HP extract treatment increased the expression of apoptotic proteins (AIF, GADD153, GRP78, caspase-3, Bax) and cell cycle G2 / M checkpoint kinase (Wee1), though it reduced antiapoptotic protein (Bcl-2) and inflammatory mediators (iNOS, COX-2, cPLA2, NFkB) in BCC cell lines. Conclusion: HP extract can support routine chemotherapy on BCC cells with its apoptotic, anti-inflammatory and anti-cancer effect, and may be a beacon of hope in reducing resistance to chemotherapeutic drugs in the treatment of BCC.
... The extract of aerial parts from Hypericum perforatum L. is rich in polyphenolic compounds ( Figure 11) and contains six major bioactive natural products groups: (1) naphthodianthrones (such as hypericin and pseudohypericin), (2) phloroglucinols (such as hyperforin and adhyperforin), (3) flavonoids (such as quercetin, rutin, quercitrin and kaempferol), (4) biflavones (such as 3,8′-biapigenin and amentoflavone), (5) phenylpropanes (such as chlorogenic acid and caffeic acid), and (6) proanthocyanidins (such as dimeric procyanidin B2 and trimeric procyanidin). In addition, there are some amounts of tannins (such as proanthocyanidins), xanthones (such as 1,3,6,7-tetrahydroxyxanthone and kielcorin), essential oils (hydrocarbons and long chain alcohols), and amino acids (such as -aminobutyric acid) ( Figure 11) [77,105,106]. ...
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This contribution focuses on the green synthesis of silver nanoparticles (AgNPs) with a size < 100 nm for potential medical applications by using silver nitrate solution and Hypericum Perforatum L. (St John’s wort) aqueous extracts. Various synthesis methods were used and compared with regard to their yield and quality of obtained AgNPs. Monodisperse spherical nanoparticles were generated with a size of approximately 20 to 50 nm as elucidated by different techniques (SEM, TEM). XRD measurements showed that metallic silver was formed and the particles possess a face-centered cubic structure (fcc). SEM images and FTIR spectra revealed that the AgNPs are covered by a protective surface layer composed of organic components originating from the plant extract. Ultraviolet-visible spectroscopy, dynamic light scattering, and zeta potential were also measured for biologically synthesized AgNPs. A potential mechanism of reducing silver ions to silver metal and protecting it in the nanoscale form has been proposed based on the obtained results. Moreover, the AgNPs prepared in the present study have been shown to exhibit a high antioxidant activity for 2, 2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) radical cation, and super oxide anion radical and 2,2-diphenyl-1-picrylhydrazyl. Synthesized AgNPs showed high cytotoxicity by inhibiting cell viability for Hela, Hep G2, and A549 cells.
... H. perforatum L. is the most studied taxon. It is used for the extraction of several bioactive compounds known for their photodynamic, antidepressive, and antiviral activities (Patocka, 2003;Vinterhalter et al., 2006;Bejaoui et al., 2017). ...
Chapter
Hypericum perforatum L. (Hypericaceae) is a perennial plant commonly known as St. John’s Wort that has been used for centuries as a medicinal herb (it has antidepressant, antiviral, wound healing, antiinflammatory, etc. properties). It contains numerous pharmacologically active ingredients, including naphthodianthrones (hypericin, pseudohypericin). These natural compounds have beneficial activity in neurodegenerative disorders, such as Alzheimer’s disease, because of their neuroprotective and antidepressant properties.
... [1] Several species of the genus have medicinal properties and are major sources of phytochemicals such as hyperforin, hypericin, pseudohypericin, hyperoside, rutin, quercetin, biapigenin, and the phenylpropanes. [2] Many species of Hypericum have photodynamic, wound healing, antidepressant, antiseptic, antiviral, anti-inflammatory, antitumor, and other pharmacological activities. [3] Of the 29 species of Hypericum occurring in India [4] , H. gaitii is an endemic and endangered species with existence of few wild populations and very narrow range of distribution in Eastern Ghats and central India. ...
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An efficient vegetative propagation method was developed for Hypericum gaitii. Indole-3-butyric acid (IBA), indole acetic acid, and naphthalene acetic acid in different concentrations and combinations were used to induce rooting in cuttings of H. gaitii. Rooting was influenced by type of cuttings and concentrations of auxins. Best rooting percentage (86.66%), number of roots (29.70), and length of roots (15.5 cm) and survival of propagules (92.30%) were recorded in apical cuttings treated with 300 mg L −1 IBA. ARTICLE HISTORY
... John's wort), has been used in traditional medicine externally for the treatment of wounds, inflammation of skin, and nerve pain, and internally as antidepressant [2]. Phytochemical researches showed that Hypericum species possessed several types of secondary metabolites such as phloroglucinols (adhyperforin, and hyperforin), flavonoids (quercitrine, hyperoside, and quercetin), naphthodianthrones (pseudohypericin, and hypericin), tannins, xanthones, phenolic acids, and the extracts prepared from Hypericum species exhibited many pharmacological and biological activities [2][3][4][5]. Hypericum extracts, especially H. perforatum extract, have been commonly used as antidepressant in Germany and other European countries, also in USA since these extracts have less side effects than those of synthetic antidepressant drugs [6]. Hypericin and hyperforin in Hypericum species are responsible for the antidepressant activity [5]. ...
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The aim of the present study was to develop and validate a LC–MS/MS method for quantification of 15 phytochemicals in Hypericum species. The developed method was fully validated in terms of repeatability (inter-day and intra-day precision), limits of detection and quantification, linearity, recovery and relative standard uncertainty. The developed and validated LC–MS/MS method was applied to determine 15 phytochemicals in the ethanol extracts of H. lysimachioides var. spathulatum aerial parts (HLS-A) and roots (HLS-R). Hyperoside was found to be the major compound in HLS-A and HLS-R ethanol extracts (16,560.3 and 3561.6 µg analyte/g extract, respectively). According to the results of GC–MS analyses, cis-13,16-docosadienoic acid (35.0%), caryophyllene oxide (24.33%) and undecane (28.21%) were determined as the major components in fatty acid, essential oil and aroma compositions of H. lysimachioides var. spathulatum, respectively. HLS-A and HLS-R ethanol extracts showed moderate activity in ABTS cation radical decolorization assay. The major components (hyperoside, astragalin, and quercetin) present in HLS-A and HLS-R ethanol extracts were found to have also the highest antioxidant effect in ABTS cation radical scavenging method. The extracts, main constituents in the extracts and essential oil had no toxic-cytotoxic potential against PDF, MCF-7 and HT-29 cell lines. HLS-A ethanol extract and essential oil exhibited high butyrylcholinesterase inhibitory activity. Quercetin showed the highest inhibitory effect against acetyl- and butyryl-cholinesterase, urease and tyrosinase among the tested samples. According to biological activity studies, H. lysimachioides var. spathulatum and their major components might be promoted as promising sources of natural agents and used in the development of nutraceuticals, functional food ingredients and pharmaceutical industry.
... [1] Several species of the genus have medicinal properties and are major sources of phytochemicals such as hyperforin, hypericin, pseudohypericin, hyperoside, rutin, quercetin, biapigenin, and the phenylpropanes. [2] Many species of Hypericum have photodynamic, wound healing, antidepressant, antiseptic, antiviral, anti-inflammatory, antitumor, and other pharmacological activities. [3] Of the 29 species of Hypericum occurring in India [4] , H. gaitii is an endemic and endangered species with existence of few wild populations and very narrow range of distribution in Eastern Ghats and central India. ...
Article
Full-text available
An efficient vegetative propagation method was developed for Hypericum gaitii. Indole-3-butyric acid (IBA), indole acetic acid, and naphthalene acetic acid in different concentrations and combinations were used to induce rooting in cuttings of H. gaitii. Rooting was influenced by type of cuttings and concentrations of auxins. Best rooting percentage (86.66%), number of roots (29.70), and length of roots (15.5 cm) and survival of propagules (92.30%) were recorded in apical cuttings treated with 300 mg L⁻¹ IBA.
... H. Perforatum has many secondary metabolites, including naphthodianthrones (hypericin, pseudo-hypericin, etc.), phloroglucinols derivatives (hyperforin, adhiperforin, etc.), flavonoids (hyperositis, routine, quercetin, etc.), biflavones (biapigenin, amentoflavone), phenolic acids (ferulic acid, caffeic acid etc.), organic acids, essential oils, amino acids, xanthones , tannins, procyanidins and other water-soluble components (Cracchiolo, 1998;Greeson et al., 2001;. The main responsible components of the pharmacological effect of H. perforatum extracts are the active constituent of naphthodianthrone pigments is hypericin and pseudohypericin, phloroglucinol derivative hyperforin, flavonoids and essential oils Hışıl et al., 2005;Medina et al., 2006;Patocka, 2003). It shows that hypericin is the main component in antidepressant effect of H. perforatum used in mental disorders (Briskin, 2000;Veronika Butterweck et al., 1998). ...
Article
Hypericum perforatum has been used by physicians since ancient times to treat certain diseases. Nowadays, phyto-therapy has an important place for people to turn to natural treatments. It is significant to examine the bioactivity of H. perforatum which is of pharmacological importance and used as a traditional medicine. H. perforatum plant was harvested in mountainous area in Celikhan region of Adiyaman. This plant was subjected to extraction process and the antioxidant capacity of the obtained extract was examined. H. Perforatum was found to have remarkable activity when evaluated for DPPH free radical scavenging activity and FRAP reducing power activity.
... H. Perforatum has many secondary metabolites, including naphthodianthrones (hypericin, pseudo-hypericin, etc.), phloroglucinols derivatives (hyperforin, adhiperforin, etc.), flavonoids (hyperositis, routine, quercetin, etc.), biflavones (biapigenin, amentoflavone), phenolic acids (ferulic acid, caffeic acid etc.), organic acids, essential oils, amino acids, xanthones , tannins, procyanidins and other water-soluble components (Cracchiolo, 1998;Greeson et al., 2001;. The main responsible components of the pharmacological effect of H. perforatum extracts are the active constituent of naphthodianthrone pigments is hypericin and pseudohypericin, phloroglucinol derivative hyperforin, flavonoids and essential oils Hışıl et al., 2005;Medina et al., 2006;Patocka, 2003). It shows that hypericin is the main component in antidepressant effect of H. perforatum used in mental disorders (Briskin, 2000;Veronika Butterweck et al., 1998). ...
Article
Full-text available
Hypericum perforatum has been used by physicians since ancient times to treat certain diseases. Nowadays, phyto-therapy has an important place for people to turn to natural treatments. It is significant to examine the bioactivity of H. perforatum which is of pharmacological importance and used as a traditional medicine. H. perforatum plant was harvested in mountainous area in Celikhan region of Adiyaman. This plant was subjected to extraction process and the antioxidant capacity of the obtained extract was examined. H. Perforatum was found to have remarkable activity when evaluated for DPPH free radical scavenging activity and FRAP reducing power activity.
... Bu çalışmalar sonucunda içeriğinde uçucu yağlar (α-pinen, sineol), antrakinon bileşikleri, karotenoidler, kumarin, flavonoidler (hiperozit, rutin, kersetin), naftodiantron yapılı bileşikler (hiperisin, psödohiperisin), karbolik asitler, floroglusinol türevi bileşikler (hiperforin), ksanton bileşikleri ve proantosiyanidinler bulunduğu belirlenmiştir (Wichtl, 1994). Patocka, 2003 Uçucu yağlar (%0,05-0,9) Hidrokarbonlar: n-oktan, nonan,dekan,dodekan,siklododekan,tridekan,undekan,limonen,afellandren,pinen,sabinen,terpinen,terpinolen,karvakrol,1,geraniol,aromadendren,bisikloseskifellandren,1,kadinen,karyofillen,karyofillen oksit, a-sedren, akopaen, kubeben, b-elemen, farnesen, germakren-D, bimakalen, humulen, leden, a-longipinen, nerolidol, selinen, spatulenol, viridiflorol, ylangen, zingiberen Barnes ve ark. 2001, Ghasemi Pirbalouti ve ark. ...
Thesis
In this study, chemical compositions of methanolic extracts prepared from flowered aerial parts of the following species collected from Uludağ, Hypericum calycinum, H. confertum and H. perforatum were investigated by LC-MS/MS. Total phenolic and total flavonoid contents were determined as pyrocatechol and quercetin equivalents, respectively. Antioxidant activities of the species were carried out by using DPPH free radical scavenging, ABTS cation radical scavenging, metal chelate and CUPRAC activity. Acetylcholinesterase, butyrylcholinesterase, urease, tyrosinase, collagenase, elastase, hyaluronidase inhibition and antimicrobial activity were also investigated.
... The major classes of Hypericum compounds that could be extracted in methanol include naphthodianthrones hypericin and pseudohypericin (Kitanov, 2001), phloroglucinol derivatives hyperforin and adhyperforin (Maggi et al., 2004;Smelcerovic and Spiteller, 2006), flavonoids (Radusiene et al., 2005), phenylpropanes (Chandrasekera et al., 2005), essential oils (Bertoli et al., 2011), xanthones (Hong et al., 2004;Tanaka and Takaishi, 2006), tannins (Dall'Agnol et al., 2003), procyanidins and other water-soluble compounds (Greeson et al., 2001). Although many of these compounds possess interesting biological properties (Patočka, 2003), hypericin holds an unique position in the pharmaceutical industry due to its application as a drug lead molecule. Hence, many Hypericum species have been investigated for the presence of hypericin and related compounds (Ferraz et al., 2002;Alali et al., 2004;Piovan et al., 2004;Çirak, 2006;Çirak et al., 2006;Ayan and Çirak, 2008). ...
Article
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Hypericum perforatum L. (St John's wort) extracts are top-selling herbal medicines for the treatment of various ailments including mild to moderate depression across the world. One of the major bioactive compounds of these extracts is hypericin that is also considered as a lead molecule for drug development. Here, we report on the development of a robust method for the simultaneous quantification of hypericins (hypericin, pseudohypericin, protohypericin and protopseudohypericin), their presumed precursors (emodin and skyrin) and new skyrin derivatives (oxyskyrin, iridoskyrin, rubroskyrin and luteoskyrin). Compounds extracted from the in vitro shoot cultures of H. perforatum L. in ethanol, acetone, 80 % methanol, ethylacetate and dichloromethane were separated by ultra-performance liquid chromatography (UPLC), quantified by photo diode array/ fluorescence (PDA-FLR) and annotated by Q- Exactive Orbitrap mass spectrometer (UPLC-QE-MS). Analyses of the UPLC data revealed that ethanol is the best extractant for the efficient quantification of all target compounds, although all of them could also be extracted in acetone and 80 % methanol. The extractants as well as the method of detection proved to be important for the efficient quantification of naphtodianthrones. Our results are expected to significantly contribute to the dissection of the hypericin biosynthesis pathway and the quality control of Hypericum extracts in the pharmaceutical industry.
... Native from Europe, western Asia, and northern Africa, this herbaceous perennial plant currently can be found worldwide. The crude drug, known as Hyperici herba, is collected from the upper part of the aerial parts of the plant before or during the flowering period [130][131][132]. ...
Article
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Patients with spinal cord injury (SCI) face devastating health, social, and financial consequences, as well as their families and caregivers. Reducing the levels of reactive oxygen species (ROS) and oxidative stress are essential strategies for SCI treatment. Some compounds from traditional medicine could be useful to decrease ROS generated after SCI. This review is aimed at highlighting the importance of some natural compounds with antioxidant capacity used in traditional medicine to treat traumatic SCI. An electronic search of published articles describing animal models of SCI treated with natural compounds from traditional medicine was conducted using the following terms: Spinal Cord Injuries (MeSH terms) AND Models, Animal (MeSH terms) AND [Reactive Oxygen Species (MeSH terms) AND/OR Oxidative Stress (MeSH term)] AND Medicine, Traditional (MeSH terms). Articles reported from 2010 to 2018 were included. The results were further screened by title and abstract for studies performed in rats, mice, and nonhuman primates. The effects of these natural compounds are discussed, including their antioxidant, anti-inflammatory, and antiapoptotic properties. Moreover, the antioxidant properties of natural compounds were emphasized since oxidative stress has a fundamental role in the generation and progression of several pathologies of the nervous system. The use of these compounds diminishes toxic effects due to their high antioxidant capacity. These compounds have been tested in animal models with promising results; however, no clinical studies have been conducted in humans. Further research of these natural compounds is crucial to a better understanding of their effects in patients with SCI.
... The extract of aerial parts from Hypericum perforatum L. is rich in polyphenolic compounds ( Figure 11) and contains six major bioactive natural products groups: (1) naphthodianthrones (such as hypericin and pseudohypericin), (2) phloroglucinols (such as hyperforin and adhyperforin), (3) flavonoids (such as quercetin, rutin, quercitrin and kaempferol), (4) biflavones (such as 3,8 -biapigenin and amentoflavone), (5) phenylpropanes (such as chlorogenic acid and caffeic acid), and (6) proanthocyanidins (such as dimeric procyanidin B2 and trimeric procyanidin). In addition, there are some amounts of tannins (such as proanthocyanidins), xanthones (such as 1,3,6,7-tetrahydroxyxanthone and kielcorin), essential oils (hydrocarbons and long chain alcohols), and amino acids (such as γ-aminobutyric acid) ( Figure 11) [77,105,106]. ...
Article
Backround and Objectives A simple and eco- friendly green method was successfully used to synthesis of nano colloidal silver (NCS) using an aqueous extract of Eucalyptus camaldulensis leaves, which acts as a reducing and capping agent. Method The goal of this work is to ensure the ability of aqueous extract of Eucalyptus camaldulensis leaves which is widely available in our region cheap and has high antioxidant activities as reducing agent for synthesis of silver nanoparticles. Total phenolic content of extract was evaluated by the well-known colorimetric assay using Folin Ciocalteu reagent. DPPH and ABTS scavenging methods were applied to assessment the antioxidant activities The formation of silver nanoparticles is tested by various techniques like UV-Vis, FTIR-spectroscopy and X-ray diffraction (XRD), scanning electron microscope (SEM), energy dispersive X-ray spectrum (EDX) and Dynamic Light Scattering (DLS). The advantage of our method lies on the fact that Eucalyptus camaldulensis extract acts both as a reducing agent and a stabilizer of silver nanoparticles. Results and Conclusion The rapid change of color from yellowish to dark brown within 10 min indicate the high ability of Eucalyptus camaldulensis aqueous extract to reduce Ag+ ions to Ago. FTIR measurements indicated the presence of amine groups which play as capping agent to prevent agglomeration of silver nanoparticles.
... Жълтият кантарион е използван като лечебна билка от древността, първоначално в Гърция. Биологично активните вещества в екстракта от жълт кантарион са нафтодиантрони (хиперицин и др.), флороглуциноли (хиперфорин и др.), флавоноиди (например кверцетин, кверцитрин, хиперозид и рутин), ксантони, етерични масла, фенолни киселини и проантроцианидини (6,10). Хиперицинът, маркер за стандартизацията за продуктите, предлагани понастоящем, се счита за основната съставка на екстракта от жълт кантарион. ...
... Effects on human behavior and animal models: regulation of mood, motivation, and reward, drugs addictions, anxiolytic, sedative, nootropic activities, anti-depressive, anti-schizophrenic and antinociceptive effects Hypericum perforatum L., also known as hypericum or St. John's Wort, is a herbaceous perennial plant native to Europe and Asia, recently introduce in North America (Barnes et al., 2001), nowadays it has a worldwide distribution (Patocka, 2003). There are many pharmacologicals active compounds that could be extracted from the roots, leaves and flowers such as flavonoids derivated as flavonols, flavones and glycosides biflavonoids including biapigeninand amentoflavone (Berghöfer and Hölzl, 1987). ...
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The aim of this review was to know the effect, properties and mechanism of action of essential oils in order to enhance their use as a treatment and adjuvant in some neurodegenerative pathologies and others associated to stress and human behavior, based on clinical trials and descriptive research. Some studies suggest that essential oils have been widely used in various applications, mainly in the pharmaceutical, cosmetic, food and agricultural industries since middle age. At the same time, based on human and animal studies has been established the effects of some essential oils about their behavior in the treatment of depression, anxiety, schizophrenic, sleep disorders in the regulation of mood modulating several neurotransmitters such as serotonin, noradrenaline, dopamine, glutamate, and gamma-aminobutyric acid also in some degenerative diseases such as Parkinson's or Alzheimer, as well as in the associated behaviors in depressive disorders, Autism spectrum disorder, ADHD, drugs addictions, people with stress and sleep disorders. It is necessary to know. RESUMEN Esta revisión tiene como objetivo conocer el efecto, propiedades y mecanismo de acción de los aceites esenciales para potenciar su uso como tratamiento y coadyuvante en algunas patologías neurodegenerativas y otras asociadas al estrés y al comportamiento humano, basado en ensayos clínicos y trabajos descriptivos. Algunos estudios sugieren que desde la edad media, los aceites esenciales han sido ampliamente utilizados en diversas aplicaciones, principalmente en las industrias farmacéutica, cosmética, alimentaria y agrícola. Al mismo tiempo, a partir de estudios en humanos y animales se han establecido los efectos de algunos aceites esenciales sobre el comportamiento en el tratamiento de la depresión, ansiedad, esquizofrenia, trastornos del sueño y en en la regulación del estado de ánimo modulando varios neurotransmisores: serotonina, noradrenalina, dopamina, glutamato y ácido gamma-aminobutírico; también en algunas enfermedades degenerativas como el Parkinson o el Alzheimer, así como en los comportamientos asociados en los trastornos depresivos, trastornos del espectro autista, trastorno de déficit de atención con hiperactividad (TDAH) , adicciones a las drogas, personas con estrés y trastornos del sueño.
... John's wort) is one of the most important medicinal plants worldwide. It is a widespread Eurasian perennial plant species with remarkable variation in its morphology, ploidy and breeding system, which ranges from sex to apomixes [3,4]. In India, it grows in Himalayas at higher altitudes and in hills of central parts of country [5]. ...
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The phytochemistry of Hypericum perforatum (St. John’s wort) has been elaborated extensively owing to its immense application in medicinal chemistry. Most of pharmacological activities were assigned to presence of photosensitive naphthodianthrone, hypericin and other allied flavonoid constituents. Escalating demands of hyperforin as antidepressant added more lure to Hypericum perforatum L. In the current study, efforts were made for quick propagation of the plant by in vitro culture using nodal explants. The nodal explants were cultured on agarized Murashige and Skoog (MS) medium supplemented with auxin and cytokinin. The highest number of shoots (50.5) per explant was found on media supplemented with 6-Benzylaminopurine (BAP) 7.5 μM and Indole-3-acetic acid (IAA) 2.0 µM. Our study showed 1.4 fold increment in shoot number viz –a-viz shoot morphogenesis from the nodal explants took about 24 days which is significantly shorter than earlier published reports. In the current study auxins Indole-3-butyric acid (IBA) and IAA were found to be equally important for root induction, whereas Napthalene acetic acid (NAA) was not required. The maximum root number (15.8) with 100% response was observed on MS + IBA (4.0 µM). Further, free radicals produced due to various environmental stresses and numerous metabolic processes ultimately lead to complete cell impairment. To combat this cellular damage organisms require dynamic defense systems. In addition to inherent defense machinery, we can supplement the defense systems of organisms with natural resources like herbs. In this regard, the free radical scavenging assay was also assessed. In our experiment line, best plant hormonal combination (I1 = MS + BAP 7.5 µM + IAA 2.0 µM) was selected on the basis of higher shootlet formation and their antioxidant activity was compared with in vitro control (I0 = MS) as well as with wild plants (W). I1 plant extracts have shown strong free radical scavenging activity with 1 fold increment as compared with wild and in vitro control.
... Effects on human behavior and animal models: regulation of mood, motivation, and reward, drugs addictions, anxiolytic, sedative, nootropic activities, anti-depressive, anti-schizophrenic and antinociceptive effects Hypericum perforatum L., also known as hypericum or St. John's Wort, is a herbaceous perennial plant native to Europe and Asia, recently introduce in North America (Barnes et al., 2001), nowadays it has a worldwide distribution (Patocka, 2003). There are many pharmacologicals active compounds that could be extracted from the roots, leaves and flowers such as flavonoids derivated as flavonols, flavones and glycosides biflavonoids including biapigeninand amentoflavone (Berghöfer and Hölzl, 1987). ...
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Full-text available
The aim of this review was to know the effect, properties and mechanism of action of essential oils in order to enhance their use as a treatment and adjuvant in some neurodegenerative pathologies and others associated to stress and human behavior, based on clinical trials and descriptive research. Some studies suggest that essential oils have been widely used in various applications, mainly in the pharmaceutical, cosmetic, food and agricultural industries since middle age. At the same time, based on human and animal studies has been established the effects of some essential oils about their behavior in the treatment of depression, anxiety, schizophrenic, sleep disorders inthe regulation of mood modulating several neurotransmitters such as serotonin, noradrenaline, dopamine, glutamate, and gamma-aminobutyric acid also in some degenerative diseases such as Parkinson's or Alzheimer, as well as in the associated behaviors in depressive disorders, Autism spectrum disorder, ADHD, drugs addictions, people with stress and sleep disorders. Keywords:essential oils, behavior, depression, anxiety, autism, ADHD, Parkinson's, Alzheimer
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The objectives of this research were to determine the variation in the amount and composition of the herbage essential oil according to different harvesting periods, and the amount and composition of the dry capsule essential oil in H. heterophyllum. The samples of herbage in four different growth stages as before flowering, beginning flowering, 50% of flowering, and full flowering and dry capsule in full maturity stage were taken from plants in a natural environment. The highest essential oil rate (0.09%) in aerial parts was recorded before the flowering stage. Also, germacrene-D, δ-cadinene, spathulenol, and α-guaiene in herbage and germacrene-D, caryophyllene oxide, and α-guaiene in the dry capsule were determined as main components. The essential oil content and the components show variation depending on the developmental stages of the plant and the part used.
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Azərbaycan Respublikasının müxtəlif coğrafi ərazilərində yayılan və kimyəvi tərkib baxımından perspektivli növ kimi qiymətləndirilən bitkilərindən biri də adi dazı – Hypericum perforatum L. bitkisidir. H.perforatum bitkisi fitokimyəvi tədqiqatlara cəlb edilərək tərkibində bioloji fəal birləşmələrdən antrasen törəmələri, flavonoidlər, polisaxaridlər aşkar edilmişdir. Aparılmış bir çox farmakoloji, klinik və laborator tədqiqatlarla dazı bitkisinin antiviral, antidepressant, yarasağaldıcı, antifunqal, iltihab əleyhinə, antibakterial təsirləri müəyyən edilmişdir. Son illərdə H.perforatum bitkisindən əldə edilən dərman vasitələrinin istehsalı kəskin şəkildə artıb və hazırda dünyada ən çox istehlak edilən dərman bitkilərindən biridir. Dazı bitkisindən alınan dərman vasitələri daxilə mədə-bağırsaq traktının xəstəlikləridə, psixoloji pozğunluqlarda, depressiv vəziyyətlərdə, nevrotik hallarda, xaricə isə müxtəlif mənşəli yaralar, ekzema, yanıqlar zamanı geniş şəkildə tətbiq olunur. Hazırda dazı bitkisinin istər elmi təbabətdə, istərsə də xalq təbabətində geniş şəkildə istifadə olunduğunu nəzərə alaraq, bu bitki haqqında topladığımız məlumatları nəzərinizə çatdırırıq... Hypericum perforatum L. is one of the plants distributed in various geographical regions of the Republic of Azerbaijan and considered as a promising species in terms of its chemical composition. As a result of the phytochemical studies of the plant, biologically active compounds, anthracene derivatives, flavonoids and polysaccharides have been found in it. Many pharmacological, clinical and laboratory studies have demonstrated the antiviral, antidepressant, anti-inflammatory, antifungal, anti-inflammatory, and antibacterial effects of the St. John’s Wort plant. In recent years, the production of medicinal products obtained from the H. perforatum has exponentially increased and it is currently one of the most consumed medicinal plants in the world. These products are widely used internally for diseases of the gastrointestinal tract, psychological disorders, depressive states, neurotic conditions, externally for wounds of various origins, eczema and burns. Given that the St. John’s Wort plant is widely used in both scientific and traditional medicine, we bring to your attention the information we have collected about this plant.
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The possibility of using the method of cell and tissue culture for microclonal reproduction of St. Johns wort is shown. Direct morphogenesis was obtained using seedlings without roots at the age of 12 days. It was found that the introduction of BAP in a low concentration (0,1 mg/l) with IAA 1,0 mg/l into the MS nutrient medium promoted the minimum bud formation with the maximum yield of morphologically normal shoots without the need for an elongation phase. At the stage of rhizogenesis, the process of root formation was observed in all variants of the experiment; the proportion of shoots with roots was high and ranged from 88 to 90%. The maximum height of shoots, the number of pairs of leaves per shoot, and the length of plant roots were reached on the MS nutrient medium with IAA 1,0 mg/l. The period of adaptation to non-sterile conditions was 30 days, while a high yield of regenerant plants was observed. The survival rate of the adapted regenerant plants in field conditions was high (100%). Regenerant plants developed rapidly and bloomed in the first year. It was revealed that before planting in open ground, St. Johns wort plants propagated in vitro culture and passed the stage of adaptation to non-sterile conditions in containers with soil mixture formed a sufficiently developed root system from regenerant plants with a large number of adventitious roots 68 cm long. At the base of the shoot, from 2 to 5 renewal shoots 912 cm in height were formed. On the 65th day after transplanting, the number of renewal shoots more than doubled and averaged 7,8 pcs. per individual with a shoot height of 23 cm. In the third decade of August, the plants entered the budding phase, and on September 20, they entered the flowering phase. It was noted that by the beginning of flowering, the height of the plants increased to 4954 cm, and the diameter of the shoot up to 0,4 cm. From 16 to 24 pairs of oblong-ovoid standard leaves were formed on the plant. The formation of the floral part of the shoot (inflorescence) 2027 cm long began with the axils of 914 leaves and consisted of 710 pairs of lateral axes (paracladia). The average number of flowers was 82. The amplitude of variability of the main morphological traits of the shoot of the studied plants was at low and medium levels. It was found that the development of microclonally propagated plants by the end of the first growing season corresponded to the growth and development of St. Johns wort plants of the second year of life grown by seedlings.
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Photoredox catalysis is a powerful and modern strategy for the synthesis of complex organic molecules. So far, this field has relied on the use on a limited range of metal-based chromophores or artificial organic dyes. Here, we show that the ubiquitous plant genus Hypericum can be used as efficient photoredox catalyst. The dried blossoms efficiently catalyze two typical photoredox reactions, a photoreduction and a photooxidation reaction, with a versatile substrate scope. Constitution analysis of the worldwide available plant genus indicated that naphthodianthrones, namely compounds of the hypericin family, are crucial for the photocatalytic activity of the dried plant material. In situ UV-vis spectroelectrochemical methods provide insights into the mechanism of the photoreduction reaction where the radical dianion of hypericin (Hyp•2–) is the catalytically active species. Our strategy provides a sustainable, efficient and an easy to handle alternative for a variety of visible light induced photocatalytic reactions
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Altitudinal variations in the content of main bioactive secondary metabolites namely, hypericin, pseudohypericin, hyperforin, the chlorogenic, neochlorogenic, caffeic and 2,4-dihydroxybenzoic acids, isoquercitrin, quercitrin, avicularin, hyperoside, rutin, biapigenin, (+)-catechin, (-)-epicatechin and in the composition of essential oil (EO) among Hypericum perforatum populations from two growing sites of Northern Turkey were investigated in detail for the first time. Aerial parts of 30 individuals at full flowering were collected at five different altitudes (391, 631, 1318, 1586 and 1733 m) of “Anzer” upland and six different altitudes (1311, 1447, 1968, 2068, 20169 and 2210 m) of “Cimil” upland in territory of Rize province, Turkey. Air dried plant samples were assayed for polar ingredients by high-performance liquid chromatography (HPLC) and for EO components by solid-phase microextraction (SPME) supported gas chromatography-mass spectrometry (GC-MS) analyses. All the tested polar phytochemicals were detected at various levels depending on altitude in both uplands and the accumulation level of each compound showed a positive consistent and significant response to altitudinal gradient. A considerable diversity in quality and quantity of major EO components was also observed and 2,2,6-trimethyl-cyclohexanone, caryophyllene oxide, tricycloheptane, hexanoic acid, tetradecanol, 2-methyl-dodecane, tetradecane, α-amorphene, eicosene, β-cedrene, piperitone, spathulenol, β-caryophyllene, δ-cadinene and linalool were identified as major EO components depending on altitude. The present results suggest that altitude of plant habitat has an ultimate effect on secondary metabolism of Hypericum perforatum and indicate the investigated populations as new chemotypes in terms of their EO composition. Such kind of findings could be useful to characterize the unique strains with desired chemical composition and can provide new viewpoints for investigations on this valuable medicinal plant.
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Amaç: Ülkemizde, halk arasında tedavi amacıyla kullanılan bitkisel droglar genellikle aktarlardan temin edilmektedir. Aktarlarda satılan drogların kalitesi ve güvenilirliği uzun yıllardır tartışılmaktadır. Bu çalışma ile önemli tıbbi bitkilerimizden biri olan ve halk arasında yaygın olarak kullanılan Hypericum perforatum türünün İstanbul aktarlarından satın alınan örnekleri incelenmiştir. Gereç ve Yöntem: Sarı Kantaron adı ile satılan droglar, İstanbul’da faaliyet gösteren, rastgele seçilmiş 12 farklı aktardan temin edilmiştir. Bitkinin toplanan kısmının (drog) ve toplanma zamanının kontrolü makroskobik ve mikroskobik incelemelerle; saklama koşullarının uygunluğu ise mikrobiyolojik test ile araştırılmıştır. Drogların kül ve nem miktarı, total antioksidan statü (TAS) ve total oksidan statü (TOS) değerleri, oksidatif stres indeksi (OSI), mineral ve ağır metal madde düzeyleri tespit edilmiştir. Droglardan hazırlanan metanol ekstrelerinin hiperisin içeriği Yüksek Performanslı Sıvı Kromatografisi (YPSK) ile analiz edilmiştir. Sonuç ve Tartışma: Bu çalışma ile örneklerin çoğunun gözle görülebilen kirlilikler ile kontamine olduğu, 6 tanesinin hiperisin içermediği, 2 tanesinin çok yüksek oranda alüminyum (Al) içerdiği belirlenmiştir. Sonuç olarak tıbbi bitkilerin gerekli denetimlere tabi tutulmadan aktarlarda satılmasının halk sağlığı açısından uygun olmadığı bir kez daha anlaşılmıştır. Mevcut bu durumun önüne geçilmesi, halkın doğru ve standart kalitede droglara ulaşabilmesi sağlanmalıdır. Anahtar Kelimeler: ağır metal, aktarlar, halk sağlığı, hiperisin, Hypericum perforatum olmadığı bir kez daha anlaşılmıştır. Mevcut bu durumun önüne geçilmesi, halkın doğru ve standart kalitede droglara ulaşabilmesi sağlanmalıdır. Anahtar Kelimeler: ağır metal, aktarlar, halk sağlığı, hiperisin, Hypericum perforatum ABSTRACT Objective: In our country, herbal drugs used for medical purposes by the folk are generally purchased from the herbal stores. The quality and reliability of the plants sold in the herbal stores have been discussed for many years. The present study aims to investigate samples of Hypericum perforatum, which is one of the important medicinal plants and widely used by the folk. Material and Method: The drugs sold as “St John’s Wort” were purchased from 12 different herbal stores which were randomly chosen in Istanbul. Quality control of the collected part and collection time of the plant were examined by using macroscopic and microscopic methods. The suitability of the plant storage conditions were investigated by microbiological test. The ash and moisture contents, total antioxidant status (TAS), total oxidant status (TOS), oxidative stress index (OSI), mineral and heavy metal levels of the plant were determined. Hypericin contents of the methanol extracts prepared from the plant samples were analyzed by High Performance Liquid Chromatography (HPLC). Result and Discussion: In this study, it was determined that most of the samples were contaminated by impurities, 6 of them did not contain hypericin, and 2 of them contained high levels of aluminium (Al). As a result, it was once again understood that it might be inconvenient to sell the medicinal plants in the herbal stores unless inspected for public health. Sale of the medicinal plants in herbal stores should be prevented, and it should be ensured that the public can reach the high quality medicinal plants. Keywords: heavy metal, herbalists, hypericin, Hypericum perforatum, public health
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In this study, the chemical and morphological diversity among eleven wild populations of Hypericum aviculariifolium Jaub. et Spach subsp. depilatum (Freyn et Bornm.) N. Robson var. depilatum, an endemic Turkish species was studied. These populations were investigated for their contents of hypericin, pseudohypericin, hyperforin, the chlorogenic, neochlorogenic, caffeic and 2,4-dihydroxybenzoic acids, hyperoside, quercitrin, isoquercitrin, avicularin, 13,118 biapigenin, (+)-catechin and (-)-epicatechin as well as for their morphological traits, including density of leaf light and dark glands, leaf area, leaf length/width ratio and plant height. The top two-thirds of the plants representing thirty individuals was harvested at full flowering from eleven sites and analyzed for the content of bioactive compounds by high-performance liquid chromatography after being dried at room temperature. Morphological characterization of the wild populations was performed on twenty randomly selected individuals from each plant-growing locality. The content of the tested compounds, except for caffeic acid and avicularin, and some morphological traits, namely, the density of leaf translucent glands and black nodules and leaf area varied significantly with the investigated populations. It was observed that hypericin and pseudohypericin contents were connected positively with leaf black nodule density, but negatively with leaf area and the contents of hyperforin, quercitrin and 13,118-biapigenin were correlated positively with leaf translucent gland density. Data presented here could be useful in determining future targets for further wide-ranging studies on this endemic species as well as in identifying superior germplasm in terms of high chemical content.
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Main conclusion Phenolic oxidative coupling protein (Hyp-1) isolated from Hypericum perforatum L. was characterized as a defense gene involved in H. perforatum recalcitrance to Agrobacterium tumefaciens-mediated transformation Abstract Hypericum perforatum L. is a reservoir of high-value secondary metabolites of increasing interest to researchers and to the pharmaceutical industry. However, improving their production via genetic manipulation is a challenging task, as H. perforatum is recalcitrant to Agrobacterium tumefaciens-mediated transformation. Here, phenolic oxidative coupling protein (Hyp-1), a pathogenesis-related (PR) class 10 family gene, was selected from a subtractive cDNA library from A. tumefaciens-treated H. perforatum suspension cells. The role of Hyp-1 in defense against A. tumefaciens was analyzed in transgenic Nicotiana tabacum and Lactuca sativa overexpressing Hyp-1, and in Catharanthus roseus silenced for its homologous Hyp-1 gene, CrIPR. Results showed that Agrobacterium-mediated expression efficiency greatly decreased in Hyp-1 transgenic plants. However, silencing of CrIPR induced CrPR-5 expression and decreased expression efficiency of Agrobacterium. The expression of core genes involved in several defense pathways was also analyzed in Hyp-1 transgenic tobacco plants. Overexpression of Hyp-1 led to an ample down-regulation of key genes involved in auxin signaling, microRNA-based gene silencing, detoxification of reactive oxygen species, phenylpropanoid pathway and PRs. Moreover, Hyp-1 was detected in the nucleus, plasma membrane and the cytoplasm of epidermal cells by confocal microscopy. Overall, our findings suggest Hyp-1 modulates recalcitrance to A. tumefaciens-mediated transformation in H. perforatum.
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Phenylpropanes, flavonol derivatives, biflavones, proanthocyanidins, xanthones, phloroglucinols, some amino acids, naphthodianthrones and essential oil constituents are the natural plant products known from the crude drug of Hypericum perforatum, Hyperici herba. These compounds are discussed with respect to structural features, their concentration, biological activities and their possible contribution to the clinically demonstrated antidepressant efficacy of extracts obtained from Hyperici herba.
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Efforts leading to the identification of hyperforin as an antidepressive component of therapeutically used alcoholic hypericum extracts are described and discussed. Initially, the effects of this unique and major constituent of the herb were detected in peripheral organs using in vitro models and an extract was obtained by supercritical extraction of the herb by carbon dioxide. These extracts are highly enriched in hyperforin (38.8%) and are devoid of hypericines and numerous other components of alcoholic extracts. Studies with such an extract and with isolated hyperforin indicated that this acylphloroglucinol derivative can inhibit serotonin-induced responses and uptake of this neurotransmitter in peritoneal cells. Assuming that the effects of hyperforin were due to its actions on serotoninergic 5-HT3/5-HT4 receptors, further studies were conducted to investigate its effects on the CNS. These efforts revealed its antidepressant activity in the behavioral despair test and led to the working hypothesis that hyperforin and serotoninergic mechanisms are involved in the antidepressant activities of alcoholic hypericum extracts. The observations made during this study also indicate that hyperforin is the major, but not the only antidepressive component of alcoholic extracts.
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To review preclinical information related to possible antidepressant mechanism(s) of action of St. John's wort in order to address the issue of whether its purported clinical effectiveness has a rational pharmacologic basis. Primary and review articles were identified by a MEDLINE search (1966-January 1998) and through secondary sources. Many of the original German articles had English abstracts, but where necessary, German articles were translated into English. The results of a new screen of hypericin activity at receptor and uptake sites are summarized. All of the articles identified from the data sources were evaluated and all information deemed relevant was included in this review. The neuropharmacology of St. John's wort has been examined in only a few studies. A mechanism similar to that of the synthetic antidepressants, such as the selective serotonin-reuptake inhibitors or monoamine oxidase (MAO) inhibitors, might play a role, but other mechanisms are possible. Hypericum extracts have only weak activity in assays related to mechanisms of the synthetic antidepressants, that is, inhibition of MAO, catechol O-methyltransferase, or serotonin reuptake. It has been postulated that the clinical efficacy of St. John's wort could be attributable to the combined contribution of several mechanisms, each one too weak by itself to account for the overall effect. The recent demonstration of a significant affinity of hypericin for sigma receptors presents new possibilities for consideration.
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Chapter
Bei einer von H. v. Tappeiner angeregten Untersuchung über die Einwirkung von Acridin-hydrochlorid und Acridinfarbstoffen auf Infusorien fand Raab (64) im Jahre 1897, daß seine Substanzen im Licht viel toxischer wirkten als im Dunkeln. Dieser Lichteffekt ist, wie eingehende Untersuchungen gezeigt haben [v. TAPPEINER (72, 73)], kein Einzelfall. So wie Infusorien verhielten sich viele andere Mikroorganismen, und wie Acridin und Acridinfarbstoffe viele andere organisch-chemische Verbindungen. Dabei ließ sich keinerlei Zusammenhang zwischen Konstitution und Sensibilisierungsvermögen erkennen. Eine Eigenschaft nur war allen sensibilisierend wirkenden Verbindungen gemeinsam, so verschieden ihre Konstitution auch sein mochte, alle zeigten in Lösung mehr oder weniger starke Fluoreszenz.
Chapter
Hypericism is a state of sensitivity to sunlight following ingestion of plants containing a pigment (hypericin) that is transferred by the bloodstream to the skin. It is mainly a disease of range animals such as sheep, cattle, and horses, but is also found in goats and swine. In the laboratory it can be induced in rabbits, rats, mice, and guinea pigs fed a diet containing the plant pigment mixed with their normal food.
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Hypericin, pseudohypericin, flavonoids, procyanidines, and tannins of the aerial parts of Hypericum perforatum and Hypericum maculatum collected in southern Austria were quantified. Analysis of covariance showed that the investigated phytochemical characteristics do not allow a chemotaxonomic assignment to H. perforatum or H. maculatum. Both a relatively strong and weak quantitative relation could be proved between the different substances by correlation analysis. Only flavonoids turned out to be in correlation to the altitude of the sites where the plants were gathered. The highest amounts of hypericin, pseudohypericin, and tannins were found at blossoming time whereas the highest yields of flavonoids and procyanidines were detected at the stage of budding. Testing of five drying methods established that the treatment to choose depends on the chemical properties of a substance.
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Benzodiazepines (BDZs) are the most widely prescribed class of psychoactive drugs in current therapeutic use, despite the important unwanted side-effects that they produce such as sedation, myorelaxation, ataxia, amnesia, ethanol and barbiturate potentiation and tolerance. Searching for safer BDZ-receptor (BDZ-R) ligands we have recently demonstrated the existence of a new family of ligands which have a flavonoid structure. First isolated from plants used as tranquilizers in folkloric medicine, some natural flavonoids have shown to possess a selective and relatively mild affinity for BDZ-Rs and a pharmacological profile compatible with a partial agonistic action. In a logical extension of this discovery various synthetic derivatives of those compounds, such as 6,3′-dinitroflavone were found to have a very potent anxiolytic effect not associated with myorelaxant, amnestic or sedative actions. This dinitro compound, in particular, exhibits a high affinity for the BDZ-Rs (Ki = 12–30 nM). Due to their selective pharmacological profile and low intrinsic efficacy at the BDZ-Rs, flavonoid derivatives, such as those described, could represent an improved therapeutic tool in the treatment of anxiety. In addition, several flavone derivatives may provide important leads for the development of potent and selective BDZ-Rs ligands.
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The two red and two violet “soluble” pigments ofHypericum species were isolated by means of extraction, chromatography, and counter-current droplet chromatography. In contrast to authentic hypericin, they are soluble in common organic solvents and even in water. Using NMR experiments it was deduced that hypericin, pseudohypericin, protohypericin, and protopseudohypericin are present in the plant as their rapidly interconverting 3- and 4-phenolate ions. From AAS the main counter-ion of these phenolates was derived to be potassium. The potassium and N-ethyl-N,N-diisopropylammonium salts of hypericin were synthesizcd for comparison. A preparative procedure to isolate hypericin and pseudohypericin from plant material was developed.
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St. John’s wort (Hypericum perforatum) is the most widely used herbal medicine for the treatment of depression. However, concerns have arisen about the potential of its interaction with other drugs due to the induction of cytochrome P450 isozymes 1A2 and 3A4 by the components hypericin and hyperforin, respectively. Structurally similar natural products are often employed as antitumor agents due to their action as inhibitors of DNA topoisomerases, nuclear enzymes that modify DNA during cellular proliferation. Preliminary findings that hypericin inhibited the DNA relaxation activity of topoisomerase IIα (topo II; EC 5.99.1.3) led us to investigate the mechanism of enzyme inhibition. Rather than stabilizing the enzyme in covalent complexes with DNA (cleavage complexes), hypericin inhibited the enzyme prior to DNA cleavage. In vitro assays indicate that hypericin is a potent antagonist of cleavage complex stabilization by the chemotherapeutics etoposide and amsacrine. This antagonism appears to be due to the ability of hypericin to intercalate or distort DNA structure, thereby precluding topo II binding and/or DNA cleavage. Supporting its non-DNA damaging, catalytic inhibition of topo II, hypericin was shown to be equitoxic to both wild-type and amsacrine-resistant HL-60 leukemia cell lines. Moreover, hypericin was incapable of stimulating DNA damage-responsive gene promoters that are activated by etoposide. As with the in vitro topo II assay, antagonism of DNA damage stimulated by 30 μM etoposide was evident in leukemia cells pretreated with 5 μM hypericin. Since many cancer patients experience clinical depression and concomitantly self-medicate with herbal remedies, extracts of St. John’s wort should be investigated further for their potential to antagonize topo II-directed chemotherapy regimens.
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The aerial parts of Hypericum reflexum contain six xanthones, two pyranoxanthones, two xanthonolignoids and a biphenyl. Six of these compounds are described for the first time.
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The hypericin content of in vitro regenerated plants of Hypericum perforatum L. was determined by spectrophotometry. A significant variability of some of the morphological characters, of the biomass production and the hypericin formation was found within the somaclones of the same genetic origin and among the regerants of different genotypes. The concentration of BAP which promoted the shoot differentiation did not affect the hypericin content and the gland density. New information on the ultrastructure of hypericin-containing multicellular glands is presented here.
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Tannin toxicity for fungi, bacteria and yeasts is reviewed and compared to toxicity of related lower molecular weight phenols. The dependence of toxicity on tannin structure is examined. The different mechanisms proposed so far to explain tannin antimicrobial activity include inhibition of extracellular microbial enzymes, deprivation of the substrates required for microbial growth or direct action on microbial metabolism through inhibition of oxidative phosphorylation. A further mechanism involving iron deprivation is proposed. Many microorganisms can overcome plant defences based on tannins. They may detoxify tannins through synthesis of tannin- complexing polymers, oxidation, tannin biodegradation or synthesis of siderophores.
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Since the last review in 1980, over eighty new xanthones have been isolated from the Guttiferae. These are listed with reference to structure elucidation and synthesis. The distribution of xanthones is examined in relation to the taxonomic divisions of the Guttiferae. Xanthone biosynthesis is discussed in the light of new biosynthetic results and the various pharmacological properties of xanthones are summarized.
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Procanidin fractions (PC) were isolated from Hypericum perforatum L. (Guttiferae). Characterization of the main components of each fraction was performed by UV- and mass spectroscopy. Their biological activity was tested in porcine isolated coronary arteries. All PC fractions antagonized histamine- or prostaglandin F2 alpha-induced arterial contractions. In contrast, vasorelaxation was insignificant in KCl-precontracted coronary arteries except with the higher oligomeric PC fraction 3. Vasoactive properties of the PC seem to be dependent on their relative molecular mass. An inhibition of cellular phosphodiesterase might be involved in the underlying mechanism of action.
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The research group at Research Triangle Institute (RTI) has had many years of experience in the isolation and structural elucidation of antitumor agents. Several of us attended the First International Conference on Antimutagenesis and Anticarcinogenesis Mechanisms (University of Kansas, 1985). Stimulated by papers presented at this meeting and the subsequent book (7), we became interested in the question whether secondary plant metabolites have a role in antimutagenesis mechanisms. There was already considerable evidence that higher plants contain a variety of preformed secondary metabolites which represent a structurally diverse array of antimutagenic and mutagenic compounds (3,5). Since we had on hand thousands of plant extracts from previous antitumor studies and had extensive experience in bioassay-directed isolation of naturally-occurring compounds, along with the availability of an active microbiology laboratory, we believed that we might be able to make a contribution to this interesting field.
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Hypericin and pseudohypericin which have been isolated from plants of the Hypericum family are aromatic polycyclic diones. Daniel Meruelo et. al. have reported that hypericin and pseudohypericin showed potent antiretroviral activity including anti-human immunodeficiency virus (1,2). However, the mechanism of these antiretroviral activities has not been clarified. In the course of screening specific inhibitors of protein kinase C we have found that both compounds specifically inhibit protein kinase C with IC50 values 1.7 micrograms/ml and 15 micrograms/ml, respectively, and show antiproliferative activity against mammalian cells. These data suggest that antiretroviral activity of hypericin and pseudohypericin could be attributable to the inhibition of some phosphorylation involved by protein kinase C during viral infection of cells.
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In a search for pharmacologically-active ingredients in the plant extract Karmelitter Geist, we have isolated and identified a high-affinity benzodiazepine receptor ligand, amentoflavon. Amentoflavon binds in a mix-type competitive and non-competitive manner to brain benzodiazepine receptors with an IC50-value of 6 nM in vitro, comparable to the affinity of diazepam. Amentoflavon shows a GABA ratio of 1.4 at 0 degrees and increases 35S-TBPS binding by 12% (60 min incubation at 25 degrees), which indicates a partial agonistic effect on benzodiazepine receptors. The substance does not influence the binding of a variety of other brain receptor ligands. Amentoflavon does not inhibit 3H-flunitrazepam-binding to brain benzodiazepine receptors following i.v. administration in the mouse in vivo, and it is therefore not likely that amentoflavon is responsible for any pharmacological effect of Karmelitter Geist.
Article
Glycosides of flavonols such as quercetin, are found in the edible portions of most food vegetables. Flavonols present in plants as glycosides can be freed during fermentation. We have compared the DNA-damaging activity of quercetin, rutin (3-o-rutinoside of quercetin) and a fermented flavonoid-containing beverage, red wine, for different genetic end-points under different metabolic conditions. The genotoxicity of quercetin, rutin and commercial red wine has been studied for the induction of: (i) reverse mutation in the Ames assay; (ii) SOS functions in the SOS Chromotest; (iii) sister-chromatid exchanges (SCEs) in human lymphocytes. While in the Ames assay the mutagenicity of quercetin is enhanced by the presence of rat liver microsomal enzymes (S9) or the respective cytosolic fraction (S100), genotoxicity is reduced when the induction of SOS responses is assessed using the SOS Chromotest. Similarly, the induction of SCEs is lowered when testing in the presence of liver enzymes. Rutin has no activity whatsoever. Detection of activity of red wine in the three assays is not dependent upon hydrolysis by glycosidases and its content of quercetin accounts almost entirely for the levels of genotoxicity detected. The results suggest that the putative genotoxic metabolites of quercetin vary for different genetic end-points considered and that the metabolic fate of flavonoids might partly account for the conflicting data about their genotoxicity in vivo and carcinogenic activity.