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Isolation and Structural Studies on Phytochemicals Active in Various Biological Assays Thesis submitted for The Fulfilment of the Degree of DOCTOR OF PHILOSOPHY by AFSHAN BEGUM H. E. J. Research Institute of Chemistry International Center for Chemical and Biological Sciences University of Karachi, Karachi-75270, Pakistan 2007 Dedicated to my Affectionate and Loving Parents Contents @ ACKNOWLEDGEMENT i fi) SUMMARY itt Gi) URDU SUMMARY (Khulasa) x Li INTRODUCTION 1 1.1.1 Natural Products and Drug Development 2 1.1.2 Natural Products-Based Medicines 2 PARTA 24 INTRODUCTION 8 24.1 ‘The Family Brogniacene 8 2.1.2 The Genus Lindelofia 8 2.1.3 Previous Phytochemical Investigation on Genus Lindelofia stylosa 9 2.14 The Plant Lindetofia stylosa 1s 2.1.5 Major Secondary Metabolites of the Plant: Polypheayl Propanoids and 15 Glycosides 21.5.1 Rosmarinie Acid 16 2.1.5.1.1 Biosynthesis of Rosmarinic Acid " 22 RESULTS AND DISCUSSION 2.2.1 Isolation of Glycosides and Phenylpropanoids from Lindelofia stylosa 24 22.2 New Compounds from Lindelofia stylosa 25 2.2.2.1 3.0-Fensloyt-6'-O-coumaroyl sucrose (1) 25 2222 —3-0-Feruloyl-6'-O-caffeoyl sucrose (2) 32 22.23 3,60-Diferuloyl I-kestose (3) 3B 22.24 — 3-0-Feruloyl-6'-O-coumaroyl 1 -kestose (4) 43 222.5 — 3,60-Diferuloyl nystase (8) 49 2.22.6 — 3-0-Feruloyi-6’-O-coumaroyl nystose (6) 55 2.2.2.7 Bthyl lithospermate (7) 6