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A Comparative Pharmacognostical Study of Certain Jasminum Species

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A Comparative Pharmacognostical Study of Certain Jasminum Species English Summary A comparative Pharmacognostical Study of certain Jasminum Species A thesis Presented by The master Fatma Alzahraa Mokhtar Ali For the degree of Ph.D in Pharmaceutical Sciences (Pharmacognosy) Under the supervision of Prof. Dr. Seham Salah El-din El-Hawary Prof. of Pharmacognosy, Pharmacognosy Department, Faculty of Pharmacy, Cairo University Prof. Dr. Hala M. El-Hefnawy Prof. of Pharmacognosy, Head of Pharmacognosy Department, Faculty of Pharmacy, Cairo University Dr. Samir M. Osman Dr. Mohamed A. ELRaey Assoc. Prof. of Pharmacognosy, Assoc. Prof. of Pharmacognosy, pharmacognosy Department, Phytochemistry and Plant Faculty of Pharmacy, October 6 Systematic Department, National University Research Centre Pharmacognosy Department Faculty of Pharmacy 1 English Summary Cairo University 2019 2 English Summary Abstract Jasminum is a genus of flowering climbing shrubs and vines (family Oleaceae). Genus Jasminum composed of over 2000 plants distributed all over the world. They are native to Eurasia, India, and the Mediterranian region. Jasminum. azoricum L., Jasminum humile L., Jasminum multiflorum Burm.f.., Jasminum officinale L., Jasminum sambac L. (Arabian nights) and Jasminum sambac L. (Grand Duke of Tuscany) were collected from AL-Keram farms, Al-Beheira Government. The plants; were subjected to DNA fingerprinting using SCOT and ISSR primers for genetic characterization. The study was performed on biologically guided bases, so four in-vitro biological studies were performed; antioxidant, antimicrobial, cytotoxic effect on three cell lines and antihepatic C virus. The comparative biological studies showed that J. multiflorum leaves have higher antioxidant effects by DPPH assay, while J. officinale and J. sambac (G) flower extracts showed more antimicrobial effects than other species and cultivars. The cytotoxicity study showed that all the species possessed cytotoxic effects in different degrees, the higher cytotoxic effects observed in J. humile and J. sambac. In-vitro HCV activity was performed in addition to cell genes analysis by western blot technique, proved that J. multiflorum leaves and flowers can decrease the viral load and inhibit its replication by 85-88%. They inhibit viral replication by affecting NS5A protein and inhibit viral penetration and expansion of infection by affecting the EPAH2 gene. Comparative phytochemical investigations were performed on the six Jasminum plants, starting with phytochemical screening for the flowers and leaves. The HPLC-PDA-ESI-MS/MS technique was used to explore the chemical composition of the leaves, a total of 115 compounds were determined tentatively with interspecies variations, different classes of compounds were identified; 5 phenylethanoids, 19 simple phenols, 18 flavonoids, 7 lignans, and 66 secoiridoids. Estimation of flavonoids and phenolic component in each plant showed the highest phenolic contents in J. multiflorum, while similarity in flavonoid contents was observed in the six plants. Volatile components of the six plants were investigated using solid phase microextraction technique, that showed the interspecies differences of volatile oil composition among selected species and cultivars, the major components were; E,E-α-Farnesene, benzoyl acetate and cis-3- hexenyl benzoate. The quantitative determination of some phenolic acids and flavonoids of the methanolic extracts of leaves were performed using HPLC-DAD method. 3 English Summary As J. multiflorum showed a very high activity towards Virus C infection, J. multiflorum was the selected plant for the isolation of biologically active compounds. A total of 14 compounds were isolated from the leaves and flowers methanolic extracts include; secoiridoids, flavonoids, phenylethanoids and phenolic acid. Virtual docking screening was performed as antiviral and cytotoxic activities, that showed compound sambacoside and molihausides are cytotoxic with no carcinogenicity, while jasfloroside A and Jasfloroside B have the antiviral activity theoretically. Green synthesis of silver nanoparticles using leaves methanolic extracts of the selected Jasminum species and cultivars was performed and study their cytotoxic activities towards three cell lines; breast cancer (MCF-7), bladder (5637), and hepatocellular (Huh-7) cell lines. Keywords: Anti HCV; Docking; Jasminum; Oleaceae; Silver nanoparticles; Secoiridoids 4 English Summary 1. Introduction Jasminum is a genus of flowering climbing shrubs and vines (family Oleaceae). Genus Jasminum composed of over 2000 pants distributed all over the world, the flowers are mostly white in color except few are yellow. They are native to Eurasia especially Italy, Iran, India and Mediterranian region (Joshi, 2000). Jasminum flowers are characterized by a very pleasant aroma, used for thousands of years in perfume industry (Yang et al, 2008). Among Jasminum species; Jasminum azoricum L., Jasminum humile L, Jasminum multiflorum (Burm.f.), Jasminum officinale L, Jasminum sambac L. Ait. (Arabian nights) and Jasminum sambac L. Ait. (Grand Duke of Tuscany) are cultivated in Egypt for commercial purposes. Jasmine flowers are sensitive flowers of great importance in industrial, food, and medicinal applications. Small differences in morphological characteristics of the flowers are present especially number and arrangement of petals. Industrially, J. officinale and J. sambac are the major sources of raw material for the perfume industry as Jasmine oil (Groom, 1997). In fact, Egypt is considered the top producer of J. officinale concrete worldwide. The concrete is exported to France, England, and USA. (Wickens et al., 1989) for the production of high grade perfumes. The Egyptian concrete is synthesized mainly from the flowers of Jasminum officinale L by solvent extraction technique (Braun et al., 2009) and have a valuable contribution in the national income. Jasminum officinale and Jasminum sambac flowers are important edible flowers used worldwide as in infusion water, Jasmine tea in USA, Europe and Asia. Jasminum officinale leaves are used as a spice in Asian foods and the flowers are used as flavoring agent in high fancy desserts (Wickens et al., 1989). Phytochemical studies of different Jasminum species attracted the attention of many authors for their wide variety of constituents. These include mainly volatile constituents (Kaviani et al., 2014; Peyrot et al., 1995); iridoids (Hao et al., 2013); secoiridoids (Takenaka et al., 1998a; Tanahashi et al., 1999b), lignans (Ali, 2018) and flavonoids (Wang et al., 2012; Zhao et al., 2012). Extracts of the plant were reported to possess many biological activities as; anticancer (Akter et al., 2014; Kalaiselvi et al., 2011), antimicrobial activity (Nagarajappa et al., 2015), anthelmintic activity (Dullu, 2014), antioxidant (Alali et al., 2007), effects on CNS (Pal et al., 2007). Reviewing the current literature, nothing was reported concerning the different Jasminum species cultivated in Egypt. 5 English Summary The aim of work: Differentiate between the different Jasminum species cultivated in Egypt A- Genetically B- Chemically C- Biologically The present study includes: 1. DNA profiling of the selected Jasminum species and cultivarsto establish genetic criteria for their characterization 2. Biological study: Evaluation of the antioxidant activity of the leaves extracts of the selected Jasminum species and cultivars Evaluation of the antimicrobial activity of the flower extracts of the selected Jasminum species and cultivars. Cytotoxic activity of the selected Jasminum species and cultivars towards breast cancer (MCF-7), hepatic cancer (Huh-7) and bladder cancer (5637) cell lines. Antiviral activity of the selected Jasminum species and cultivars towards hepatic viral C infection. 3. Phytochemical study Preliminary phytochemical screening of methanolic extracts of leaves and flowers of the selected Jasminum species and cultivars HPLC-PDA-ESI-MS/MS analysis of chemical composition of the leaves of the selected Jasminum species and cultivars Estimation of volatile oil composition flowers of the selected Jasminum species and cultivars by solid phase microextraction (SPME) technique and chemometric analysis Qualitative and quantitative detrermination of phenolics and flavonoids in the selected Jasminum species and cultivars Isolation of chemical constituents from the most bioactive fractions. Virtual screening of some identified and isolated compounds using molecular docking. 4. Application Green synthesis of silver nanoparticles using leaves methanolic extracts of the selected Jasminum species and cultivars. 6 English Summary Review of literature Several reports focused on the chemical constituents of different Jasminum species and isolation of chemical components viz; iridoids, secoiridoids, phenolic acids, flavonoids and volatile oils, which have been reported as major components of these spp. 2.1. Chemical constituents of genus Jasminum 2.1.1. Iridoids and secoiridoids: Analysis performed on Jasminum tortuosum Willd, led to the isolation and the identification of four compounds, namely ginkgool, olivil-4′-O-β- glucopyranoside. oleoside dimethyl ester, and oleoside 11-methyl ester. The presence of these compounds is significant from a chemotaxonomic point of view (Tomassini et al., 2018). Eight compounds including four caffeoyl phenylpropanoid glycosides, jasnervosides A–D, one monoterpenoid glycoside, jasnervoside E, and three secoiridoid glycosides, jasnervosides F–H, were isolated from the stems of Jasminum nervosum Lour. (Oleaceae),
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