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Phytochemical and Biological Study of Tribulus Terrestris and Fagonia Arabica

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Phytochemical and Biological Study of Tribulus Terrestris and Fagonia Arabica Phytochemical and Biological Study of Tribulus terrestris and Fagonia arabica A Thesis Submitted by Dina Magdy Abd El-Hameed Ghanem (Bachelor Degree of Pharmaceutical Sciences) Research Assistant – Pharmacognosy Department National Research Centre For the Degree of Master in Pharmaceutical Sciences (Pharmacognosy) Under the Supervision of Prof. Dr. Seham Salah El-Din Prof. Dr. Nagwa Mohammed El-Hawary Ammar Prof. of Pharmacognosy Prof. of Pharmacognosy Department of Pharmacognosy Department of Pharmacognosy Faculty of Pharmacy National Research Centre Cairo University, Egypt Giza, Egypt Pharmacognosy Department Faculty of Pharmacy Cairo University Egypt 2016 1 دراسة فيتوكيميائية و بيولوجية للتريبيوﻻس تريسترس و الفاجونيا ارابيكا رسالة مقدمة من دينا مجدى عبد الحميد غانم )بكالوريوس العلوم الصيدلية( مساعد باحث- قسم العقاقير المركز القومى للبحوث للحصول على درجة الماجستير فى العلوم الصيدلية )عقاقير( تحت اشراف أ.د. /سهام صﻻح الدين الهوارى أ.د. نجوى محمد عيسى عمار أستاذ العقاقير- قسم العقاقير أستاذ العقاقير- قسم العقاقير كلية الصيدلة – جامعة القاهرة المركز القومى للبحوث – الجيزة ج. م . ع ج. م . ع قسم العقاقير كلية الصيدلة – جامعة القاهرة ج. م . ع ٦١٠٢ 2 English Abstract This study focused on two plants growing in Egypt, the aerial parts of Tribulus terrestris L. and Fagonia arabica L. (Family Zygophyllaceae), which have been used extensively in folk medicine for a variety of purposes. This study aimed for the performance of phytochemical and biological studies of the two plants under investigation. Tribulus terrestris L. possesses many important biological activities; aphrodisiac activity, antimicrobial, cytotoxic and antioxidant activities. Fagonia arabica L. has effects on hematological parameters, as well as, antimicrobial, cytotoxic and antioxidant activities. The results of the biological study revealed that the aqueous methanolic extracts of the aerial parts of T.terrestris L. and F.arabica L. were responsible for these biological activities. So it was of deemed interest to investigate the phytoconstituents of the two bioactive extracts separately. Phytochemical and chromatographic studies were performed using different solvent systems and detection by Khagi-Mischner and AlCl3 reagents which revealed the presence of high percentage of saponins and phenolic compounds in the two extracts under investigation. Therefore, it was decided to perform quantitative estimation of total flavonoid and phenolic contents, qualitative and quantitative estimation of flavonoids as well as phenolic compounds by HPLC analysis, isolation and identification of flavonoidal compounds, preparation and phytochemical investigation of saponin content through chromatographic and mass screening studies and finally quantitative estimation of diosgenin in T.terrestris L. by HPLC analysis. The flavonoid content of the methanolic extracts of the aerial parts of T.terrestris L. and F.arabica L. were isolated where the extracts were subjected to fractionation using several chromatographic techniques (CC and TLC) leading to the isolation of five compounds which are identified using several spectroscopic techniques (UV, 1HNMR and 13CNMR). From T.terrestris L. quercetin and rutin and from F.arabica L. quercetin, quercetrin and naringenin were isolated respectively. 3 All the obtained results confirm the advantage of the use of T.terrestris L. and F.arabica L. as effective therapeutic agents from botanical origin. This can be realized after doing the necessary toxicological and pharmaceutical studies. The pharmaceutical formulation of the biologically active fractions is recommended after the toxicological tests. The teamwork is looking to achieve the benefits from this work by applying the primary clinical application of the promising results after doing the necessary toxicological and pharmaceutical studies. 4 Introduction The genus Tribulus of the Zygophyllaceae family comprises several species which grow as shrubs or herbs in subtropical areas around the world (Achenbach et al., 1994). From which Tribulus terrestris L. is very common in Egypt. T.terrestris L. is very common in the Nile delta including Cairo but not further South, Nile valley from Cairo to Wadi Halfa, the Mediterranean coastal strip from El-sallum to Rafah, Sinai proper i.e. South of El-Tih desert (especially in waste places) (Täckholm, 1974). This plant can be found in arid climate regions around the world; for example, in Southern USA, Mexico, Spain, Bulgaria, India and China (Ganzera et al., 2001). On the other hand T.terrestris L. used in folk medicine against various diseases. The fruits and seeds are of great importance in folk medicine because they are used as an aphrodisiac, diuretic and anthelmintic, as well as, to treat cough and kidney failure. T.terrestris L. has the reputation of having anabolic effect as well as in USA as dietary supplement. It is used in many countries against sexual impotency, oedema, abdominal distention and cardiovascular diseases (Combarieu et al., 2003). Preparation containing T.terrestris L. extract are on sale in USA as food supplement with claim of general stimulating action on motor activity, muscle tone and restorative tonic for vigor. Indeed, T.terrestris L. preparations are mainly used to improve performance in sports and for treatment of impotency. More recently, it has been reported that an aqueous extract of T.terrestris L. appeared to possess aphrodisiac properties probably due to androgen increasing properties. Earlier investigation performed on T.terrestris L. resulted in the isolation of steroidal saponins, flavonoids, carbohydrates and alkaloids (De Kock and Enslin, 1958), (Tomova et al., 1974), (Perepelitsa and Kintya, 1975), (Hamed et al., 2004), (Wang and Lu, 1991), (Kang et al., 2014), (Bhutani et al., 1969), (Saleh et al., 1982), (Shi et al., 1999), (Reshma et al., 2015), (Borkowski and Lutomski, 1960), (Wu et al., 1999), (Sharma and Narula, 1977), (Huang et al., 1991) and (Chen et al., 2002). The genus Fagonia (family Zygophyllaceae) is represented in Egypt by eighteen species (Täckholm, 1974). The Fagonia arabica – complex is made up of four species: F.arabica L., F.acerosa Boiss., F.zilloides Humbert and F.taeckholmiana Hadidi. While Fagonia acerosa Boiss. is only reported 5 from South Persia and West Pakistan on the Eastern distribution limits of F.arabica L., on the other hand, F.zilloides Humbert is only known from South Morocco and Fagonia taeckholmiana Hadidi is endemic to the Galala Desert of Egypt. F.arabica L. is considered to be wide spread, ranging in distribution from the North Africa Sahara to South Arabica and Pakistan (Hadidi, 1972). F.arabica L. and F.taekholniana Hadidi are found in Egypt. F.arabica L. is a common and rather polymorphic species with distinct spiny stipules, lower tri and upper unifoliate leaves. Fagonia taekholmiana is a rare species characterized by the absence of the spiny stipules and the distinctly unifoliate leaves (Täckholm, 1974). In traditional medicine, aqueous extracts of Fagonia species were reported to exhibit medicinal properties and used for treatment of cholera, prolonged fever and snake bites (Chopra et al., 1956). It’s reputed to be a medicinal plant in scientific and folkloric literature and its medicinal values are well documented (Chopra et al., 1982). An aqueous decoction of the aerial parts is a popular remedy in the indigenous system of medicine for cancer in its early stages and for treatment of various other diseases of digestive and blood vascular system (Saeed, 1969). The medicinal properties of the plant were attributed due to its variety of active constituents. Although the plant had received a great interest for the phytochemical investigation since many years, yet the chemical structure of most of its constituents were established during the last 15 years. The entire plants of various Fagonia species were investigated mainly for the presence of two major classes of phytochemical compounds, i.e. flavonol glycosides and terpenoid glycosides (Saleh et al., 1990), (Miyase et al., 1996), (El-Wakil, 2007), (El-Negoumy et al., 1986) and (El-Hadidi et al., 1988). This study will include: Part I: Phytochemical study: 1. Preliminary phytochemical screening and proximate analysis of the aerial parts of T.terrestris L. and F.arabica L. 2. Investigation of the volatile constituents of the aerial parts of T.terrestris L. and F.arabica L. 3. Investigation of the lipoidal matter of the aerial parts of T.terrestris L. and F.arabica L. 4. Investigation of the carbohydrate content of the aerial parts of T.terrestris L. and F.arabica L. 6 5. Investigation of the protein and amino acid contents of the aerial parts of T.terrestris L. and F.arabica L. Part II: Biological study: 1. Determination of acute toxicity of T.terrestris L. and F.arabica L. 2. Evaluation of the aphrodisiac activity of T.terrestris L. 3. Evaluation of the effect on hematological parameters of F.arabica L. 4. Evaluation of the in vitro antimicrobial activity of T.terrestris L. and F.arabica L. 5. Determination of the in vitro cytotoxic activity of T.terrestris L. and F.arabica L. 6. Determination of the in vitro antioxidant activity of T.terrestris L. and F.arabica L. Part III: Phytochemical investigation of biologically active extracts: 1. Phytochemical investigation of flavonoid and phenolic contents in the bioactive aqueous methanolic extract of T.terrestris L. and F.arabica L. 2. Investigation of the flavonoidal compounds in the bioactive methanolic extract of T.terrestris L. and F.arabica L. 3. Phytochemical investigation
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