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Phytochemical and Biological Studies of Cordia Africana Family Boraginaceae Cultivated in Egypt

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Phytochemical and Biological Studies of Cordia Africana Family Boraginaceae Cultivated in Egypt Phytochemical and Biological Studies of Cordia africana Family Boraginaceae Cultivated in Egypt A Thesis submitted By Maha Abd El Mohsen Abd El Reheem Mohamed For the degree of master in pharmaceutical sciences (Pharmacognosy) Under the supervision of Prof. Dr. Seham Salah El Din El Hawary Professor of Pharmacognosy, Faculty of Pharmacy, Cairo University Prof. Dr. Mona El Mahdy El Tantawy Professor of Pharmacognosy, Medicinal Plants Department, Ex. Chairman of National Organization for Drug Control and Research Pharmacognosy Department Faculty of Pharmacy Cairo University A.R.E 2016 1 English Abstract This study focus on Cordia africana Lam. cultivated in Egypt. Firstly DNA profiling was done for selective discrimination of this plant. The results of phytochemical screening revealed the presence of different constituents .The chemical composition of the essential oil of flowers was investigated by GC/MS, the percentage of Oxygenated compounds identified in flowers oil (84.16%). Investigation of lipoidal matter of leaves of plant revealed the presence of pentanediol as the major hydrocarbon identified (53.95%). study of carbohydrate content of Cordia africana Lam. Fruits was done .it found that it composed of mannitol (27.60%). Nutritional value of the fruits was evaluated .The fruits are rich in total protein, minerals and vitamins. Qualitatative and Quantitative estimation of polyphenols and flavonoids of some Cordia species in Egypt were performed and comparing between different concentrations of phenolics and flavonoids was done to distinguish between these species. Quantitative determination of polyphenols and flavonoids of leaves, flowers and fruits of Cordia africana Lam. Was carried out. High resolution UPLC-MS analysis of Cordia africana Lam. Leaves and Fruits extracts was done. Twenty one of peaks were tentatively identified in negative mode for each leaves and flowers. Isolation and identification of phytoconstituents of leaves from ethyl acetate and butanol fractions were performed and the compound isolated were Quercetin, Para hydroxy phenyl lactic acid, Quercetin -O-β-D-glucopyranoside, Isorhamnetin -O- rutinosoide, rutin and gallic acid. Biological Study of the different extracts of leaves and fruits of Cordia africana Lam. was done and it was found that the alcoholic extracts of leaves and fruits and aqueous extracts of leaves and fruits have antioxidant, anti-inflammatory and anti- diabetic activities. Evaluation of cytotoxic activity and antimicrobial activity of different extracts of leaves and fruits and the essential oil of flowers showed activities with different percentage. (Key Words: Cordia, africana, Boraginaceae, carbohydrate, rutin 2 INTRODUCTION Cordia is a genus of flowering plants belong to family Boraginaceae, subfamily Cordioideae. The family Boraginaceae consists of about 2,700 species which are distributed in tropical, subtropical and warmer regions around the world (Gottschling, 2003). It is composed of about 130 genera and six subfamilies: Boraginoideae, Cordioideae, Ehretioideae, Heliotropioideae, Hydrophylloideae, and Lennooideae. The subfamily Cordioideae contains the genus Cordia, which is comprised of evergreen trees and shrubs (Thirupathi et al., 2008); about 300 species of Cordia have been identified worldwide Many of these species are commonly called Manjack (Quattrocchi, 2000). Many species of Cordia have fragrant showy flowers and are popular in gardens (Bennett, 2003). The tropical species of Cordia are used widely as anti inflammatory for wound healing (Kuppast & Nayak, 2006), antioxidant (David et al., 2007), for skin diseases, antimicrobial, antifungal, antiviral, astringent, antidiarrhea, digestive, antiulcers, anthelementic (Kuppast & Nayak, 2003), analgesic, hoemostatic, antirhumatic, arthritic and also for treatment of snake-bite, rabies and malaria. Some of the previous uses are proved scientifically and used medicinally and the others are common in folk medicine in their native countries. Cordia africana Lam have many uses in folk medicine; the wood –ash, mixed with butter is applied to certain skin troubles, leaves decoction are administrated to treat headache, nose bleeding, dizziness and vomiting during pregnancy (Protabase-Plant Resources of Tropical Africa). The leaves are dried and powdered to sprinkle over wounds. A root decoction is drunk as a treatment for jaundice and schistosomaisis (Burkil, 2004). 3 Fruits of several Cordia species are edible as they have nutrition value due to its carbohydrate content specially mucilage (Verma et al., 1977). The studies carried about this genus Cordia approved the presence of wide variety of active constituents; Cordia contains a group of chemicals; naphthoquinones derivatives called Cordiachrome A-F & cordiaquinones A-M. Other plant chemicals in Cordia include, cordialin A and B (Velde et al., 1982), Cordianols, A-I. (Kuroyangi et al., 2005) and many flavonoids and phenolic acid as artemetin rutin and robinin (Ficarra et al., 1995). Although certain species of the genus Cordia had attracted the attention of several authors from the phytochemical point of view, little work appears to have been reported on Cordia africana Lam. It was thus, deemed important to carry out a phytochemical investigation of Cordia africana cultivated in Egypt. Aim of work Phytochemical investigation of different plant extracts and study of their biological activities. The study includes: I. Taxonomy and DNA Profiling. 1- Taxonomy of plant 2- DNA Profiling of Cordia africana lam. II. Phytochemical study 4 1. Preliminary phytochemical screening of the Cordia africana 2. Analysis of the essential oil content of flowers 3. Investigation of lipoidal matter of leaves of Cordia africana Lam. 4. Investigations of carbohydrate content of Fruits 5. Nutritional evaluation of fruits. 6. Qualitative and Quantitative estimation of phenolic compounds and flavonoids in some species of Cordia present in Egypt. 7. UPLC/UV/MS analysis of leaves and Fruits extracts 8. Isolation and Identification of some active constituents by different chromatographic and spectroscopic techniques. III. Biological evaluation - Determination of LD50. - Investigation of the anti-inflammatory activity. - Estimation of the antioxidant activity. - Estimation of hypoglycemic activity. - Cytotoxic activity. - Antimicrobial activity of the essential oil and different extracts of leaves and fruits. REVIEW OF LITERATURE Reviewing the current literature, genus Cordia contains many chemical constituents viz, volatile constituents as α-Pinene (Oliveria et al., 2007), flavonoides and phenolic derivatives (Marstan et al., 2009), terpenoides compounds (Freitas et al., 2012), Sterols (Geler, 2010), alkaloids (Parks et al., 2010), polysaccharides and free sugars (Benhura & Chidewe, 2002). It was reported also that the plant extracts of different species of Cordia possess different biological and microbiological activities (Emtinan et al., 2015). 5 A- Chemical constituents of genus Cordia Previous studies on different Cordia species revealed the presence of the following chemical constituents: - Volatile constituents: Table (1). - Flavonoids and phenolic compounds: Table (2). - Terpenoid compounds: Table (3).- 6 1) Volatile constituents: Table (1): Volatile constituents reported in genus Cordia. Plant Compounds Plant Species Structure Reference Part Menezes C.trichotoma Heart α-Muurolol et al., Vell. wood (2005( Menezes et al., C.trichotoma Heart (2001). α-Cadinol Vell. wood Menezes et al., (2005). Menezes et al., Epi-α- C.trichotoma Heart (2005) muurolol Vell. wood Menezes C.trichotoma Heart et al., γ-Cadinene Vell. wood (2005) 7 Continue Table (1): Volatile constituents reported in genus Cordia. Plant Compounds Plant Species Structure Reference Part - Menezes ol - C.trichotoma Heart 11 et al., - Vell. wood (2005) dien Guaia 3,10(4) C.curassavica Stem Oliveria, Jacq. et al., hulenol (2007) Spat C.salicifolia leaves Oliveria - C.globosa Jacq. Stem et al., Endo - 1 (2007) bourbonanol Oliveria C.globosa Jacq Stem et al., Linalyl butyrate (2007) Oliveria C.globosa Jacq Leaves et al., ne - (2007) C.verbenacea Meccia Caryophylle – D.C Aerial et al., β parts ) 2009( 8 Continue Table (1): Volatile constituents reported in genus Cordia. Plant Plant Structure Reference Compounds Species part H C C. 3 H3C H C CH3 verbenacea 3 Mederios - D.C H C et al., rans 3 T H2C ) 2007( Caryophllene C.globosa Leaves Oliveria Jacq. et al., (2007) Mederios et al., (2007). Passos et al., Humulene - -- (2007). α C. Fernandes verbenacea et al., D.C (2007). Chaves et al., (2008) H C H3C 3 C. Oliveria curassavica Stem et al., H C 3 CH Transe hydrate 3 Jacq. OH (2007) Sesquisabinene 9 2) Flavonoids and phenolic compounds: Table (2): Flavonoids and phenolic compounds reported in genus Cordia. Plant Plant Compounds Structure Reference species part CH3 Dominguez 3,4'-Dimethyl C.boissiri HO O Flower et al., kaempferol A.D.C CH3 OH (1973) O OH 5,7-Dimethoxy- Chauchan C.obliqua H CO O taxifolin-3-O- α-L- Root 3 OH et al., Willd Orhamnose rhamnopyranoside. OCH (1978) 3 O Chauchan Root et al., OH (1978) Hesperetin-7-O-α-L- C.obliqua O rhamnose O rhamnopyranoside Willd OH Agnihotri O Seed et al., (1987) 3', 5-Dihydroxy-4'- OCH 3 O Tiwari methoxy flavonone C.obliqua Stem rhamnose O OH et al., 7-O-α-L- Willd bark OH O (1979) rhamnopyranoside. OH Taxifolin-3-O-α-L- C.obliqua HO O Srivastava Seed OH rhamnopyranoside. Willd (1979) O rhamnose OH O Continue Table (2): Flavonoids and phenolic compounds reported in genus Cordia. 10 Plant Plant
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