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Pharmacognostical Investigation of Some Yucca Species (Asparagaceae) a Thesis Submitted By

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Pharmacognostical Investigation of Some Yucca Species (Asparagaceae) a Thesis Submitted By Pharmacognostical Investigation of some Yucca Species (Asparagaceae) A Thesis submitted By M.Sc. Samar Mohamed Bassam Moaz For The Degree of Doctor of Philosophy in Pharmaceutical Sciences (Pharmacognosy) Under the Supervision of Prof. Dr. Seham Salah El Din El-Hawary Professor of Pharmacognosy, Faculty of Pharmacy, Cairo University Assistant Prof. Dr. Abeer Mohamed Ali El-Sayed Assisstant Professor of Pharmacognosy, Faculty of Pharmacy, Cairo University Assistant Prof. Dr. El-Moataz Bellah Ali El-Naggar Assisstant Professor of Pharmacognosy, Faculty of Pharmacy, Damnhour University Dr. Hanan Samir Marzouk Lecturer of Pharmacognosy, Faculty of Pharmacy, Pharos University in Alexandria Pharmacognosy Department Faculty of Pharmacy Cairo University A.R.E 2019 1 Abstract Yucca is a genus of woody perennial shrubs and trees, native to Central America northward to southernmost Canada. This genus is highly reputed for its economic importance as a source of fibers and saponins for rope and soap industries, respectively. Yucca aloifolia L., and its variety Yucca aloifolia variegata L., Yucca filamentosa L. and Yucca elephantipes Regel leaves were collected from Orman Botanical Garden, to investigate their biological activities and to carry on phytochemical investigation of the most active species. The plants were first subjected to thorough botanical study and DNA fingerprinting to aid their authentication and identification in any future study. Biological investigation of the total alcoholic extracts of the leaves of the 4 plants, lead to the conclusion of the excellent hepatoprotective effect of the 4 plants using in-vivo CCl4-induced hepatotoxicity model. In-vitro cytotoxicity investigation proved the outstanding cytotoxic activity of Y. aloifolia variegata L., especially against hepatocellular carcinoma and breast cancer cell lines. However, antimicrobial activity screening showed the lack of activity in both water and alcoholic extracts of the 4 plants. As a result, Y. aloifolia variegata L. was considered the most active and was subjected to further phytochemical investigation. This included preliminary phytochemical screening, determination of total phenolic content, quantitative and qualitative determination of flavonoids and phenolic acids in fraction using HPLC, investigation of lipoid content using GC-MS for both saponifibale and unsaponifiable fractions, and finally LC-MS/MS of the total extract and some fractions. LC-MS/MS was used to for identification of 10 isolated compounds. These investigations lead to the identification of 129 compounds in Y. aloifolia variegata L., among which saponins, flavonoids, phenolic acids, stilbenes, hydrocarbons and fatty acids. This study is the first to investigate Y. aloifolia variegata L. botanically, genetically and phytochemically. Molecular docking in-silico experiments were done for some of the major compounds against possible protein targets in cytotoxic activity. The docking scores were good for all the investigated compounds, indicating the holistic action of the alcoholic extract. Keywords: Yucca aloifolia, Yucca aloifolia variegata, Yucca filamentosa, Yucca elephantipes, LC-MS, HPLC, saponins, flavonoids, phenolics, DNA fingerprinting, molecular docking, hepatoprotective, cytotoxic 2 Introduction Yucca is a genus of woody perennial shrubs and trees. It is a terrestrial plant, stems are absent, short or thick and arborescent, then usually more or less branched. Its species are notable for their rosettes of evergreen, with numerous sword-shaped leaves which are more or less ensiform. These leaves are nearly linear, thin or flexible maybe somewhat thicker and very rigid having horny or smooth margins, which are often desintegrate into fibres and terminal spines often present (Szabo K. , 2011). Genus Yucca was first classified under family Liliaceae (Pai and Patil, 2011), tribe Yuccae, due to its superior ovary (Szabo K. , 2011). However, later it was moved to family Agavaceae (Oleszek and Bialy, 2006). Agavaceae is a monocot family of flowering plants in the order Asparagales, more recently reduced to the subfamily Agavoideae of the family Asparagaceae(Chase et al., 2009). The family includes many well-known desert and dry zone types. It comprises about 550-600 species in around 24 genera, widespread in the tropical, subtropical and warm temperate regions of the world. The genus Yucca has been estimated to conservatively comprise 35–40 species within its native range from Central America northward to southernmost Canada. Historically, three sections have been defined based on differences in fruit morphology. Two sections contain species with indehiscent fruit, including the fleshy-fruited Sarcocarpa and the spongy-fruited Clistocarpa, and the remainder belonging to the section Chaenocarpa with dry, dehiscent fruits. Within the Chaenocarpa, there is also consensus in historical, morphology-based treatments for a subset referred to as the Rupicolae. Clistocarpa is monotypic, while the two other sections have roughly equal numbers of taxa. Relationships among these sections remain unsettled (Olle P., 2007) These flowering plants generally thrive in arid parts of Southwestern US and Mexico, namely Mojave, Sonoran, Colorado and Chihuahuan Deserts, chaparrals of coastal California, sand dunes and Baja California.The majority are xeromorphic and succulent rosette plants of desertic regions. However, the species Yucca aloifolia L. (Spanish bayonet) grows in Southeastern USA. Yucca whipplei (Chaparral yucca) is prevalent in the south California chaparral. Yucca brevifolia (Joshua tree) is the signature plant of Mojave Desert. Yucca schidigera (Mojave yucca) is prevalent across Mojave and Sonoran Deserts and regarded highly for its pharmaceutical values. Yucca elata (Soap tree yucca) is another distinct species in Sonoran and Chihuahua deserts. Yucca elephantipes (Giant yucca) is often planted for landscape purpose in urban area (Patel, 2012). 3 Yucca is widely recognized for its pollination mutualism with yucca moths. Pollination of Yucca depends entirely on moths of the genera Tegeticula and Parategeticula (Prodoxidae).These moths have coevolved as obligate mutualists with their yucca hosts, and their whole life cycle is intimately associated with the host plant. Yucca moths mate within host flowers, and the mated female uses unique mouth parts to collect pollen from anthers (Svensson et al., 2011). The main application of yucca products is in animal nutrition, in particular as a food additive to reduce ammonia and fecal odors in animal excreta. The positive effects of dietary supplementation with yucca products on the growth rates, feed efficiency, and health of livestock seem to be due not only to the saponin constituents but also to other constituents (Paola Montoro, 2008). Yucca gloriosa roots were used historically to remove gall bladder stones. Crushed roots are taken every morning and night (Mohammed Rahmatullah, 2010). Aim of the work Very few studies were done to investigate different yucca species introduced to Egypt. Therefore, this study aims at investigating the chemical composition and the biological activities of three yucca species cultivated in Egypt; Yucca aloifolia and its variety Yucca aloifolia variegata, Yuuccafilamentosa and Yucca elephantipes. This work includes the following: 1. Review of the current literature. 2. Botanical study and DNA fingerprinting of the plant. 3. Investigation and evaluation of biological activities of different extracts and fractions. 4. Preliminary phytochemical screening of different organs of the different plant species. 5. Biologically-guided phytochemical investigation of the most active species. 6. Identification of major chemical constituents of the active species. 4 Review of Literature Chemistry of Genus Yucca Review of literature illustrated that genus Yucca is rich in saponins, which represents the major chemical constituent. Other constituents reported to be isolated from yucca include, sterols and phenolic constituents. 1- Saponins: Steroidal saponins, both spirostanol type and furostanol type have been isolated from different species of Yucca. Yokosuka et al. (2014) succeeded to isolate six steroidal glycosides and 14 known compounds from the underground parts of Yucca glauca. Their structures were determined from extensive spectroscopic analysis, including two-dimensional NMR data, and chemical transformations. The isolated saponins were both of spirostan and furostan types. The compounds were also evaluated for cytotoxic activities against HL-60 human leukemia cells and A549 human lung adenocarcinoma cells. Ibrahem and Awad (2013) performed a study to detect the presence of the most important steroidal sapogenin “Tigogenin” in the leaves of Yucca aloifolia widely cultivated in Iraq. The identification of isolated Tigogenin was carried out using melting point (M.P.), thin layer chromatography (TLC), infrared spectroscopy (IR) and High performance liquid chromatography (HPLC). 2- Phenolic compounds and Flavonoids (Table 3 and Table 4) Many phenolic compounds have been isolated or identified from Yucca species. Juarez-Trujillo et al. (2018) investigated the methanol crude extract of Yucca elephantipes Regel flowers from Mexico using LC-MS analysis. The analysis led to the tentative identification of a considerable number of flavonoids and phenolics. Nakashima et al. (2016) isolated three new phenolic compounds, yuccalides A–C from the roots of Y. gloriosa. The structures of the new compounds were established by extensive
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