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Phytochemical and Biological Study of Pelargonium Peltatum (L.) L'her

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Phytochemical and Biological Study of Pelargonium Peltatum (L.) L'her Phytochemical and Biological Study of Pelargonium peltatum (L.) L’Her. Family Geraniaceae Cultivated in Egypt Thesis submitted by Fatma Hassan Mohammed Nossier For the Degree of Master in Pharmaceutical Science (Pharmacognosy) Under supervision of Prof. Dr. Aly Mohamed El Sayed Professor of pharmacognosy Faculty of pharmacy Cairo University Prof. Dr. Azza Ramy Abd El Moneam Professor of Pharmacognosy Faculty of Pharmacy Cairo University Dr. Rehab Mohammed Seif El Din Ashour Lecturer of Pharmacognosy Faculty of Pharmacy Cairo University 2019 Abstract are noted with considerable economic (عتر :Several herbs belong to genus Pelargonium (Arabic importance in ornamental plants market. Pelargonium originates from South Africa, where more than 200 species are cultivated. In Egypt, Pelargonium species are cultivated in Upper Egypt, mainly Beni Suef and Faiyum. Some Pelargonium species contain volatile oil called geranium oil which has economic value in perfume industry and cosmetics. Also, geranium oil has biological importance as it was reported to possess antibacterial, antifungal, anti-oxidant, insect repellent and other activities. Pelargonium peltatum (L.) L‟Her. cv. Balcon lilla is characterized by green, succulent and palmately lobed leaves. The color of the flowers is pale pink. The preliminary phytochemical screening followed by TLC of the 70% ethanolic extract and its fractions revealed that n-hexane and methylene chloride fractions were rich in sterols and triterpenes, while ethyl acetate and n-butanol fractions were rich in flavonoids and tannins. This is the first study of the volatile components of Pelargonium peltatum (L.) L‟Her. and the first time to use head space GC/MS for analyzing the oil of Pelargonium species. Five compounds were identified, namely; β- myrcene (44.86%), (-)-β-pinene (35.89), (-)-α-pinene (10.4%), p-mentha-1(7),8-diene (5.14%) and camphene (3.71%). Four compounds were isolated and identified from the ethyl acetate fraction; 1- O-monogalloyl-β-glucose, gallic acid, ethyl gallate and 1,2,3,4,6-pentagalloyl-ß-D-glucopyranose (PGG). The total phenolic and flavonoids contents were 19.3992 mg GAE/g and 2.7203 mg QE/g of dry weight, respectively. HPLC/MS profiling revealed the presence of thirty one compounds, twelve flavonoids and nineteen phenolic acid derivatives. Seventeen compounds were identified for the first time in the Pelargonium species. It is the first HPLC profiling of Pelargonium peltatum (L.) L‟Her. cv. Balcon lilla. In vivo and in vitro screening of biological activities of the 70% ethanolic extract of Pelargonium peltatum (L.) L‟Her. leaves and its fractions revealed that n- hexane fraction showed the most potent analgesic activity. The 70% ethanolic extract showed analgesic, anti-inflammatory and anti-hyperglycemic activities. Methylene chloride and ethyl acetate fractions showed high anti-inflammatory and anti-oxidant activities. The most effective cytotoxic fraction on the three tested cell lines was methylene chloride fraction. Introduction For thousands of years, natural compounds, mostly from plants, have been the mainstay of traditional medicine. They also have been the source of lead compounds for modern medicine (Ginsburg and Deharo 2011). In fact more than 25% of modern pharmaceuticals are plant derived are noted with considerable (عتر :Duke 1993). Several herbs belong to genus Pelargonium (Arabic) economic importance as ornamental plants in the market, gardens and forest free area. Pelargonium comes from Greek word “pelargos” (stork) because of the beak like fruits. Pelargonium commonly called geranium and originates from South Africa where more than 200 species are cultivated (Adams et al., 2006). In Egypt, Pelargonium species are cultivated in Upper Egypt, mainly Beni Suef and Fayoum. Geranium oil is secreted from glandular hairs located on both surfaces of the scented leaves of several species and cultivars. The volatile oil constitutes valuable commercial value in perfumery, cosmetics and aromatherapy. The main sites of production of geranium oil are Egypt, China and Reunion (Wells and Lis-Balchin 2002). European countries such as Spain, France and Italy produce smaller scale. The best quality of geranium oil comes from Reunion and Egypt where climate, soil and other vital factors contribute to quality of the oil (Demarne 2002). Geranium oil is among the top twenty of plant volatile oils; so many researches were conducted on volatile oils of different species to explore their chemical composition and biological activities. The oil was reported to contain monoterpenoid (Cavar and Maksimovec 2012) and sesquiterpenoid constituents (Kayser et al., 1998). Best oil composition is obtained with citronellol/geraniol ratio of 33/26% in January planted crops (Williams and Harborne 2002). Geranium oil is applicable in aromatherapy for massage as relaxant agent. For skin disorders, it heals fungal infections, athlete's foot, eczema, hemorrhoids (Saraswathi et al., 2011), bruises and burns. It has antiseptic and haemostatic activities, and relieves tiredness, general fatigue and convalescence (Lis-Balchin 2002). Geranium oil is also a wonderful insect repellent (Alipour et al., 2015). Pelargonium species were reported as rich source of tannins, flavonoid derivatives (El-Sherei et al., 2004a), coumarins (Hauer et al., 2010) and phenolic acids (Bauer and Treutter 1990). Pelargonium peltatum (L.) L‟Her. (family Geraniaceae), known as ivy-leaved geranium, hanging is one of the species cultivated in Egypt and used for ,(جارونيا مدادة أو جارونيا لير :geranium (Arabic ornamental purpose. It has faint odor and attractive flowers which last from May to July. It is used in folk medicine for treatment of oral ulcer and toothache (Scott et al., 2004; Walt 1977). Aim of work The current literature revealed the importance of Pelargonium species concerning their commercial value as oil producing, chemical constituents and biological activities. Although, available literature about this genus was numerous, little was reported on Pelargonium peltatum (L.) L‟Her. No published data was found concerning the chemical composition and biological activities of the Egyptian Pelargonium peltatum (L.) L‟Her. cultivar Balcon lilla. This encouraged us to investigate this ornamental species chemically and biologically and explore its medicinal value. The current present study includes reviewing the literature of different Pelargonium species, determination of the macro-morphological characters of Pelargonium peltatum (L.) L‟Her. cultivar Balcon lilla. plant, phytochemical screening of the 70% ethanolic extract of the dried leaves and its fractions (n-hexane, methylene chloride, ethyl acetate and n-butanol) to determine the different constituents, investigation of the volatile constituents of the leaves using GC/MS, isolation and identification of major phenolic compounds by chromatographic and spectroscopic techniques, determination of total phenolic and flavonoids, profiling the polar secondary metabolites of the 70% ethanolic extract by HPLC/MS/MS, finally; the biological activity of the 70% ethanolic extract and its different fractions (n-hexane, methylene chloride, ethyl acetate and n-butanol) were evaluated for their analgesic, anti-inflammatory, anti-hyperglycemic, cytotoxicity and antioxidant properties. Review Geuns Pelargonium was rich in compounds from different classes such as essential oil flavonoids tannins and coumarins. Also this genus showed diversity of biological activities such as antimicrobial, anti-oxidant, anti-cancer, anti-inflammatory and other biological activities. Essential oil Some Pelargonuium species have distinct fragrance and contain essential oil. The essential oil distilled from Pelargonium species is called geranium oil. The oil was reported to contain monoterpenoid and sesquiterpenoid constituents. Pelargonium graveolens L'Herit. constitutes the main source of geranium oil. The major components of geranium oil are citronellol, geraniol, linalool and 10-epi-γ-eudesmol Geranium oil is important in aromatherapy for massage and for skin disorders. Verma et al., (2010) studied the changes in the essential oil composition of rose scented geranium Palergonium graveolens L‟Herit. cv. „CIM-Pawan‟ due to the date of transplanting in India (from December to April). The oil was analyzed by GC. The main components of the oil were citronellol (21.3-28.7%), geraniol (23.1-38.4%), linalool (4.2-6.5%), iso-menthone (6.5-7.9%), citronellyl formate (6.3-8.3%), 10-epi-γ-eudesmol (4.7-5.6%) and geranyl formate (3.3-4.3%). Boukhris et al., (2013a) analyzed the essential oil of the aerial parts of Pelargonium graveolens L'Herit. by GC/MS. The main constituents of the oil were β-citronellol (21.9%), citronellyl formate (13.2%), geraniol (11.1%), 10-epi-γ-eudesmol (7.9%), geranyl formate (6.2%) and linalool (5.6%). Koheil et al., (2012) analyzed the composition of the essential oil of leaves and flowers of Pelargonium zonale L. cultivated in Egypt by GC/MS. Hydrodistillation of the leaves and flowers yielded 0.12% and 0.06% v/w of the fresh plant, respectively. The essential oil of the leaves was typified by the presence of β-caryophyllene (24.6%), α-humulene (23.8%), caryophyllene oxide (8.5%) and α-cedrol (8.3%); while that of the flowers was characterized by α-humulene (36.73%). Meanwhile, the major monoterpene hydrocarbon was β-myrecene (7% & 1.6%, respectively) in both oil samples. Andrade et al., (2011) identified the chemical composition of the essential oil from the leaves of Pelargonium
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