Alkaloids in S. Buxifolia Root and Stem Bark of S

Introduction Introduction The natural products and natural medicine are nowadays withdrawing attention than the allopathic system. They remain the best sources of drugs and drug leads, and this remains true today despite the fact that many pharmaceutical companies have deemphasized natural products research in favor of HTP screening of combinatorial libraries during the past 2 decades. Moreover, this system of medicine is pollution free and less toxic with minor side effects. Out of the 6000 plants mentioned in the traditional systems of medicine, only 350 species are under use (Malviya et al., 2012). Family Rutaceae comprises about 158 genera and 1900 species widely distributed in both temperate and tropical zones of the new, as well as, the old world. It is represented by 23 genera and over 80 species occurring mostly in the tropical and subtropical Himalayas and the Western Peninsular of India. (Mabberley, 2008). The family consists mainly of trees or shrubs and a very small proportion of herbs, all of which flourish in the tropics and sub- tropics. It belongs to the order Sapindales and has an ancient name known as Rue family (Bailey, 1958). Rutaceae has been used in the folk medicine for the treatment of gastrointestinal 1 Introduction disorder such as anorexia, constipation and nausea, extract of Rue family has been used as a vermifuge, several species are used as tonic and diuretic (Metcalf and Chalk, 1950). Rutaceae is of great economic importance with the most valuable members yielding Citrus fruits such as oranges, lemons, mandarins, limes, tangerines and grapefruit. Numerous species are cultivated for their precious essential oils such as Neroli and Bergamot that are used in the natural healing and perfume industries. Citrus genus is the most important source of essential oil as Citrus oils have been widely used in both perfumery and food industries. The constituents of such major Citrus fruits as lemon (Clark and Bernhard, 1960) orange (Shaw and Coleman, 1974) and grapefruit (Umano et al., 1994) are well characterized. Rutaceae is best known by the exotic genus Citrus, because of its commercially consumed fruits. Other groups of the same subfamily of Citrus are commonly cultivated as ornamentals in America, including species of Atalantia, Clausena, Murraya, and Swinglea. Genus Atalantia includes approximately 20 speciecs (Roskov et al., 2016). Amongst Atalantia species, Atalantia buxifolia or Severinia buxifolia (Poir.) Tenore is the plant of our interest. 2 Introduction Severinia buxifolia (Atalantia buxifolia) which is commonly known as the thorny, evergreen shrub. In Hanian province of China, the roots of Atalantia buxifolia are used in folk medicine for the treatment of influenza, cough, malaria, and stomachache by the people of Li nationality. Acridone alkaloids were the major alkaloids reported in Atalantia buxifolia, these alkaloids nucleus possess insect antifeedant and cytotoxic activities, respectively (YangTao, 2012). Atalantia buxifolia has been used in chinese folk medicine for treatment of chronic rheumatism, paralysis, snake bite and malaria, Atalantia buxifolia is also used for foundation and as a hedge plant (Wu and Chen, 2000). Moreover, leaves are used as yeast cake (Gilman, 1999). This study hightlights the phytochemistry and activity of the leaves. Other organs were not studied as there is only one tree in the Orman garden. The only available organ is the leaf. The present study includes the following: 1. Literature survey and reference books about Severinia buxifolia (Poir.)Tenore. (Atalantia buxifolia) 2. A botanical study of the different organs as well as DNA fingerprinting. 3. Preliminary phytochemical screening of the leaves. 3 Introduction 4. Investigation and identification of essential oil of the leaves by GC ̸ MS. 5. Investigation and identification of lipoidal matter of leaves by GC ̸ MS. 6. HPLC analysis of butanol, ethyl acetate and methylene chloride fractions of leaves of Severinia buxifolia (Poir.) Tenore. 7. Isolation, purification and characterization of the major chemical constituents from different fractions using different chromatographic and spectral methods. 8. Biological study of the ethanolic extract as well as its fractions prepared from the leaves together with the major isolated compounds. 4 Introduction Review of literature This literature survey was performed on Severinia buxifolia (Poir.) Ten. as an attempt to shed light on the data reported concerning their major constituents and biological activities as well as to serve as a helpful guide during the foregoing study. Major Constituents It was reported that S.buxifolia (Poir.) plant, family Rutaceae characterized by presence of the most important constituents. Examples are volatile oil, flavonoids, coumarins, alkaloids, triterpenes, sesquiterpenes and other miscellaneous compounds. In the leaf extract, the major compounds found are coumarins and volatile oil. No acridone alkaloids or limonoids were detected except in the root bark only (Bacher et al.,2010) as the following: 1- Flavonoids Flavonoids represent one of the largest and most studied classes of phenylpropanoid-derived plant specialized metabolites, with an estimated 10,000 different members. Structurally, they consist of two main groups, the 2-phenylchromans (the flavonoids, including flavanones, flavones, flavonols, flavan-3-ols, and anthocyanidins) and the 3-phenylchromans 5 Introduction (the isoflavonoids, including isoflavones, isoflavans, and pterocarpans. Flavonoids have been ascribed positive effects on human and animal health and are central to the current interest in “botanicals” for disease therapy and chemoprevention (Dixon and Pasinetti, 2010). Bacher et al., (2010), Buckingham et al., (2015) reported presence of two new flavones Atalantoflavone, 4ˊ-O-methyl atalantoflavone in the methanolic extract of the leaves of S. buxifolia (Poir.) Tenore as minor components. Qi and Yu, (1986) isolated 4′, 5-dihydroxy, 3′-OCH3, 2″, 2″- dimethyl pyrano (5″, 6″, 7, 8) flavone from the leaves of Atalantia buxifolia (Poir) Oliv. By spectral analyses (UV, IR, NMR, MS) and chemical transformation the structures of this new compounds was elucidated and identified. 2- Coumarins in S. buxifolia The name coumarin originates from Tonka tree (Coumarouna odorata) from which coumarin itself was isolated. Coumarins have been characterized in 178 rutaceous species from 50 genera. (YangTao, 2012). Bacher et al., 2010 founded coumarins (seselin, isomeranzin, suberosin epoxide, bergaptene, imperatorine, suberosine, 6 Introduction bergamottin) as the major compounds in CHCl3 fraction of the ethanolic leaf extract of S.buxifolia (Poir.) Tenore. While the remaining coumarins and the flavones have not been described for S. buxifolia yet. Chen et al., 2001 also isolated umbelliferone, 8-Geranyl-7- hydroxycoumarin, Auraptene and 7-geranyl-6-methoxycoumarin from the methylene chloride fraction of the methanolic extract of the leaves and the root bark of Atalantia buxifolia (Poir.) Tenore and these compounds are identified by different spectral analysis. WU et al., 1998 studied presence of umbelliferone, 8-Geranyl-7- hydroxycoumarin in the ethanolic extract of the leaves of S.buxifolia (Poir.) Tenore. Qi and Yu, 1986 isolated eleven chemical Constituents including two new compounds were isolated from the leaves of Atalantia buxifolia (Poir) Tenore. By spectral analyses (UV, IR, NMR, MS) and chemical transformation the structures of two new compounds were elucidated as 4′, 5-dihydroxy, 3′- OCH3, 2″, 2″- dimethylpyrano (5″, 6″, 7, 8) flavone and 4-(3′-methyl-but-2′-ene) oxy, N-benzoyl phenethylamine. Seven known compounds were identified as friedelin, lupeol, α-amyrin, γ-sitosterol, β-sitosterol, 7-(6′, 7′-dihydroxy-3′, 7′-dimethyl-2-octenyl) oxycoumarin and umbelliferone. 7 Introduction Dreyer, 1967 described seselin as a major component of the leaves alcoholic extract and small amounts of imperatorin, isopimpinelin and bergapten in the fruit ethanolic extracts of S.buxifolia (Poir.) Tenore. 3- Alkaloids in S. buxifolia Root and stem bark of S. buxifolia (Poir.)Tenore are rich in alkaloids. Yang et al., 2013 isolated two new acridone alkaloids, 3- methoxy-1, 4, 5-trihydroxy-10-methyl acridone and 2, 3- dimethoxy-1, 4, 5-trihydroxy-10-methylacridone from the ethanolic extract of S. buxifolia. Tao et al., 2012 isolated seven alkaloidss from the ethanolic extract of roots of Atalantia buxifolia (Poir.) Oliv. by means of chromatographic technique. On the basis of spectral data, their structures were identified as buxifoliadine A, 1, 3-dihydroxy-2, 4- diprenylacridone, 5-hydroxy-N-methylseverifoline, buxifoliadine B, N-methylatalaphylline, atalaphylline and atalafoline. Acridones having unique molecular structure of two benzene rings fused together having nitrogen atom at C10 position and a keto group at C9 position. Acridone have a wide range of biological activities such as antiviral, anticancer, anti-HIV, anti- fungal, anti-microbial, antiherpes, and antimalarial and anti- 8 Introduction leishmanial. The journey of acridones as pharmaceuticals was started by Paul Ehrlich in late nineteenth century (Giridhar et al., 2010). WU and Chen, 2000 isolated eight new acridone alkaloids, buxifoliadines A-H together with nine known acridone compounds from the root bark of S. buxifolia which was collected in Hainan province of China. Their structures were determined by spectroscopic methods. They studied the relationship between acridone alkaloids with the collecting area. The 13C-NMR

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