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العنوان
Isolation and identification of bioactive secondary metabolites from Senna italica & Prosopis farcta (Family Fabaceae), and their soil associated fungi /
المؤلف
KHALAF,OMAR MAAJAL.
هيئة الاعداد
باحث / OMAR MAAJAL KHALAF
مشرف / Hassan M.F. Madkour
مشرف / Mohamed El-Sayed Abdel-Aziz
مشرف / Ahmed Kamel El-Ziaty
مشرف / Amal Mohamed Saad
تاريخ النشر
2018
عدد الصفحات
388p.;
اللغة
الإنجليزية
الدرجة
الدكتوراه
التخصص
Organic Chemistry
تاريخ الإجازة
1/1/2018
مكان الإجازة
جامعة عين شمس - كلية العلوم - كيمياء عضوية
الفهرس
Only 14 pages are availabe for public view

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Abstract

Family Fabaceae commonly known as the legume, pea, or bean family, is a large and economically important family of flowering plants which comprises about 350 species. The Fabaceae have an essentially worldwide distribution, the trees are often found in tropical regions, while the herbaceous plants and shrubs are predominant outside the tropics. Senna italica has been widely used in folk medicine for the treatment of many diseases, while Prosopis farcta has been used in the treatment of neurological disorders. The present work includes phytochemical and biological investigations on two Egyptian plants namely; Senna italica & Prosopis farcta and their soil associated fungi (Terfezia species).
This study resulted in the separation and identification of ninety-nine compounds, some pure and some within natural mixtures. In order to determine the contents of these plants, a series of organic solvents was used (hexane, methylene chloride, ethyl acetate and finally butanol). chromatographic separation techniques such as column and thin layer chromatography were used for separation and purification of compounds. Also, spectroscopic tools like; 1H-NMR, 13C-NMR, DEPTQ, HSQC, HMBC, and GC/MS). In addition to evaluation of their bioactivities including; antimicrobial (measuring the diffusion disk), antioxidants, and cytotoxicity as well as fungal cultures.
The chromatographic investigation led to the isolation of three new compounds from Senna italica as for compound 3 was isolated for the first as a new compound of natural products (3, 4 and 6), and three known compounds (1, 2, and 5). The vehicles were identified using spectral means (1H-NMR, 13C-NMR, DEPTQ, HSQC, HMBC, and GC/MS) as physcion 1, emodin 2, 2-methoxy-emodin-6-O-β-D-glucopyranoside 3, 1-hydroxy-2-acetyl-3-methyl-6-hydroxy-8-methoxynaphthalene (tinnevellin) 4, quercetin 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (rutin) 5, and 1,6,8-trihydroxy-3-methoxy-9,10-dioxo-9,10-dihydroanthracene 6. In addition, the GC/MS analysis of S. italica extracts revealed that the major constituents of the n-hexane were n-hexadecanoic acid (30%), (Z,Z,Z)9,12,15-octadecadienoic acid (21%), vitamin E (7.32%), and for methylene chloride were 3-methyl-4-oxopentanoic acid (16.36%), (E)-stilbene (11.86%), and 2,6-di-tert-butylphenol (10.70%). Moreover, the results revealed that the n-hexane extract of S. italica showed weak antimicrobial activity with inhibition zones were ranged from 3.8 to 7mm, and the methylene chloride extract showed a potent antimicrobial activity with inhibition zones were ranged from 4.2 to 18mm. Also, the n-hexane showed weak anticancer activity with IC50 equal to 81.6±4.1, 73.0±3.90, 66.8±3.12, and 92.8±4.82 μg/ml, while the methylene chloride exhibited a potent anticancer activity with IC50 of 16.9±1.30, 17.4±1.36, 18.3±1.59, and 14.2±1.18 μg/ml, all respectively for HePG-2, Hela, PC3, and MCF-7 tumor cell lines. The activity against ABTS radical was recorded with the methylene chloride (% inhibition= 86.3%), compared to ascorbic acid with 89.2%.
On the other hand, of P. farcta extracts led to the chromatographic isolation of the ethyl acetate and n-butanol extracts resulted in the isolation of four compounds which were identified as; dihydrokaempferol-3-O-α-L-rhamnoside 80, apigenin 81, 4′-methoxyquercetin (tamarixetin) 82 and acacetin-7-O-α-L-rhamnoside 83, were isolated for the first time from P. farcta, In addition, the GC/MS analysis of P. farcta extracts led to the identification of twenty-six and thirty-two compounds respectively from n-hexane and methylene chloride. The major compound identified in the n-hexane is (Z) 9,17- octadecadienal (10.60%) while for methylene chloride is tricosanoic acid (9.24%). The n-butanol extract of P. farcta showed the highest activity against MCF-7 cell line with IC50 of 5.6 μg/ml compared to 5-fluorouracil with IC50 of 5.4 μg/ml, while the ethyl acetate showed the highest activity against Hela cell line with IC50 of 6.9 μg/ml compared to 5-fluorouracil with IC50 of 4.8 μg/ml. Also, the inhibition percentages (I%) of ABTS radical were 83.1, 82.0, 87.2 and 87.0% respectively for the n-hexane, methylene chloride, ethyl acetate and n-butanol extracts, respectively.
The chromatographic isolation separation of methylene chloride, ethyl acetate and n-butanol fractions of Terfezia species led to the identification of eight compounds namely; (R)-4,8-dihydroxy-7-hydroxymethyl-6-methoxyisochroman-1-one 142, 4-deoxy-4α-phorbal-12-(2,3-dimethyl)butyrate-13-isobutyrate 143, oxyphylline B 144, terfezien A 145, latilagascene D 146, amaiouine 147 and senbusine acetate 148, were isolated for the first time from Terfezia species. Moreover, sixteen compounds were identified in n-hexane extract via GC/MS analysis, accounting for 93.69% of the total detected components in the extract. While twenty-six components were detected in methylene chloride extract, represent 43.86% of total detected components in the extract. Eight fungal strains were isolated from Terfezia sp., powder by serial dilution methods and these fungi were cultivated on solid rice medium and their ethyl acetate and acetone extracts were subjected to biological studies including antimicrobial, antioxidant and anticancer activities. The three potent fungal strains 1M, 4M and 8M were identified by the molecular technique 18SrRNA as Aspergillus niger 1M-EGY-IQ, Penicillium crustosum 4M-EGY-IQ, and Fusarium proliferatum 8M-EGY-IQ.
Keywords: Senna italica, Prosopis farcta, Terfezia species, 18SrRN, GC/MS, phenolics, antioxidant, antimicrobial, anticancer.