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
2007Dedicated to my
Affectionate and
Loving ParentsContents
@ 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