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Chemical and Biological Assessment of Stachys Aegyptiaca Pers

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Chemical and Biological Assessment of Stachys Aegyptiaca Pers Chemical and Biological Assessment of Stachys aegyptiaca Pers. Growing in Egypt A thesis submitted by Alaa Mohamed Abd-El-Moniem Mohamed Shaheen In partial fulfillment of the requirements for the degree of Master in Pharmaceutical Sciences (Pharmacognosy) Under the Supervision of Prof. Dr. Essam Abdel-Sattar Chairman of Pharmacognosy Department Faculty of Pharmacy Cairo University Prof. Dr. El-Sayeda Ahmed El-Kashoury Professor of Pharmacognosy Faculty of Pharmacy Cairo University Assoc. Prof. Dr. Mohamed El-Amir Fathey Hegazy Associate Professor of Medicinal Plant Chemistry National Research Center Pharmacognosy Department Faculty of Pharmacy Cairo University A.R.E. 2017 تقييم كيميائي وبيولوجي لنبات ستاكيس ايجيبتياكا (القرطم( الذي ينمو في مصر رسالة مقدمة من أﻻء محمد عبد المنعم محمد شاهين ﻹستيفاء متطلبات الحصول على درجة الماجستير في العلوم الصيدلية )عقاقير( تحت إشراف أ.د/ عصام عبد الستار أستاذ ورئيس قسم العقاقير كلية الصيدلة-جامعة القاهرة أ.د/ السيدة أحمد الكاشورى أستاذ العقاقير كلية الصيدلة- ج امعة القاهرة أ.م.د/ محمد اﻷمير فتحي حجازي أستاذ مساعد بقسم كيمياء النباتات الطبية المركز القومي للبحوث قسم العقاقير كلية الصيدلة- جامعة القاهرة جمهورية مصر العربية 2017 Abstract Genus Stachys is one of the largest genera of family Lamiaceae consisting of about 300 species. It is centered in the Mediterranean region and south western Asia. Stachys aegyptiaca Pers. is a perennial aromatic plant growing wild in Wadi Jilbal, Sainte Catherine, Sinai. Preliminary phytochemical screening and estimation of the total phenolic and flavonoid contents were performed. Essential oil of Stachys aegyptiaca was obtained by two different techniques, conventional hydrodistillation (HD) and microwave assisted extraction (MAE). Gas chromatography-mass spectrometry analysis of the essential oil obtained by both techniques was carried out. Phytochemical investigation of the methylene chloride/methanol (1:1) extract of the air-dried aerial parts of the plant resulted in isolation and characterization of three new diterpenes (Stachyaegyptin A, B and C) together with four known neo-clerodane diterpenes (Stachysolone, 13- Mono-acetyl-stachysolone, Diacetyl-stachysolone and Rosestachenone). Seven methoxylated flavonoid aglycones were isolated. Three methoxy flavones were isolated for the first time from genus Stachys identified as 3, 7, 3', 4'- Tetramethyl-quercetin, Eupatilin-7-methyl ether and 5, 8-Dihydroxy-3, 6, 7, 4'- tetramethoxy flavone. 5-Hydroxy-3, 6, 7, 4'-tetramethoxy flavone was isolated for the first time from S. aegyptiaca while Calycopterin, 5-Hydroxy auranetin and Xanthomicrol were previously isolated from S. aegyptiaca. The extract and isolated compounds were evaluated for their anti-inflammatory, cytotoxic and antioxidant activities. Keywords: Stachys aegyptiaca, Lamiaceae, essential oil, diterpenes, methoxylated flavones, biological activities. Introduction People have always suffered from diseases by bacteria, fungi, viruses, parasites, cold, digestive problems, inflammation and pain. Modern medicines, depending on synthetic drugs and antiinfectives, became only available during the last 150 years. Previously, people had to rely on drugs from nature especially from plants, fungi and animals. Medicinal systems, developed thousands of years ago, heavily relied on herbal medicine. The treatment of infections and health disorders with herbal medicines is due to their content of active natural products (Wink, 2015). Family Lamiaceae (Labiatae or mint family) is one of the most diverse and widespread plant families. It contains about 236 genera and 6,900 to 7,200 species of flowering plants. Its medicinal value is mainly based on high essential oil content. Many species belonging to the family are highly aromatic due to the presence of external glandular structures that produce essential oil. Members of family Lamiaceae are widely cultivated due to their aromatic nature and their ease of cultivation as they can propagate by stem cuttings (Raja, 2012). Genus Stachys is one of the largest genera of family Lamiaceae consisting of 300 species and centered in the Mediterranean region and south western Asia (Jassbi et al., 2014). Many species of this genus have been widely used in traditional medicine, as long ago as the times of early Egyptian civilization. Aerial parts of several species have been used as infusions and decoctions to treat skin disorders, stomachache, ulcer, asthma, rheumatic pains and cancer (Gören, 2014). Many species of the Stachys genus are used to prepare a wild tea, also known as ‘mountain tea,’ that is believed to be sedative, antispasmodic, diuretic and emmenagogue (Gören, 2014). In addition, several Stachys species are also used as a food, as their edible tubers are an important source of carbohydrates such as Stachys affinis Bunge. They were also used in traditional medicine in treatment of diarrhea, sore throat, internal bleeding and weakness of heart and liver (Venditti et al., 2013a). Pharmacological studies on extracts or pure compounds of several Stachys species demonstrated cytotoxic, antimicrobial, antioxidant, anti- inflammatory and anxiolytic effects. Phytochemical reports on the genus revealed the presence of flavonoids, essential oils, phenylethanoid glycosides, diterpenes and irridoids as secondary metabolites (Tundis et al., 2014). Stachys aegyptiaca is a perennial plant growing wild in Sinai deserts. Aim of work Several flavonoid compounds were isolated from the 70% ethanolic extract (El-Ansari et al., 1991 and 1995) or the methanolic extract (El- Desoky et al., 2007) of S. aegyptiaca while few reports were found on diterpenoid content of S. aegyptiaca (Melek et al., 1992; Mohamed and Mohamed, 2014) despite of the numerous types of diterpene skeletons identified in the genus Stachys (Piozzi and Bruno, 2011). In this study, the aerial parts of the plant were extracted with the less polar solvent mixture methylene chloride/methanol (1:1) with the aim of: Isolation of new natural products with an important biological profile. Chemical characterization of the isolated compounds. Comprehensive bioassay testing of lead compounds, including cytotoxicity, antioxidant and anti-inflammatory activities. This study includes the following 1. Review of literature regarding the phytoconstituents and bioactivity of the members of the genus Stachys. 2. Preliminary phytochemical screening of the aerial parts of Stachys aegyptiaca. 3. Estimation of the total phenolic and flavonoid contents of the aerial parts of the plant. 4. Comparative investigation of the essential oils of the aerial parts prepared by conventional hydrodistillation and microwave assisted extraction. 5. Isolation, purification and characterization of the chemical constituents of the aerial parts using different chromatographic and spectral techniques. 6. In-vivo evaluation of the anti-inflammatory activity of the total extract as well as the in-vitro evaluation of the total extract and the isolated compounds for their cytotoxic, anti-inflammatory and antioxidant activities. Review of literature Stachys is one of the largest genera of family Lamiaceae, containing about 300 species. It is a subcosmopolitan genus distributed in warm temperate regions of Mediterranean, Europe and in almost all types of habitats and at all altitudes (Munoz et al., 2001). Phytochemical investigations of the genus Stachys revealed the presence of essential oils (Halim et al., 1991; Grujic-Jovanovic et al., 2011; Karami and Dehghan-Mashtani, 2015), terpenoids (Fazio et al., 1994a and 1994b; Paternostro et al., 2000; Mohamed and Mohamed, 2014), flavonoids (El-Ansari et al., 1991 and 1995; Vundać et al., 2005), phenylethanoid glycosides (Ikeda et al., 1994; Nishimura et al., 1991; Delazar et al., 2011), iridoids (Munoz et al., 2001; Murata et al., 2008) and triterpenoid saponins (Yamamato et al., 1994; Cho et al., 2014a and 2014b). The different species of the genus were also investigated for their antimicrobial (Farjam et al., 2011; Yildirim et al., 2013; Jassbi et al., 2014;), antioxidant (Morteza-Semnani et al., 2006; Bilušić Vundać et al., 2007; Ebrahimabadi et al., 2010), anxiolytic (Rabbani et al., 2003 and 2005; Kumar et al., 2013) and anti-inflammatory activities (Benmebarek et al., 2013a; Sadeghi et al., 2014; Barreto et al., 2016). Major active constituents of the genus Stachys I. Essential oil constituents The essential oil yield of Stachys species is low compared to other members of family Lamiaceae (e.g. Origanum, Satureja, Sideritis, Salvia and Thymus) however, the consumption pattern of the Stachys species is quite similar to the other members of the family. Most species of the genus Stachys have pleasant smell except few species have unpleasant smell due to their essential oil (Gören, 2014). They are consumed as herbal tea in the major parts of the world due to their moderate antibacterial, antifungal, anti-inflammatory and anti-oxidant capacity. They are widely used as herbal remedy in alternative medicine (Gören, 2014). The composition of the essential oil of the genus Stachys has been studied extensively. Investigation of the essential oil of S. aegyptiaca obtained from the leaves by hydrodistillation revealed the presence of fourteen monoterpenes hydrocarbons, four oxygenated monoterpenes and seven sesquiterpene hydrocarbons (Halim et al., 1991). Published data concerning the chemical composition of the essential oils of different species of the genus are summarized in Table (1) and the structures of selected oil constituents are represented in Figure (1). II.
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