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Bioactive Compounds from Boerhavia Erecta L University of Wollongong Research Online University of Wollongong Thesis Collection University of Wollongong Thesis Collections 2010 Bioactive compounds from Boerhavia erecta L. : an African medicinal plant Ari Nugraha University of Wollongong Recommended Citation Nugraha, Ari, Bioactive compounds from Boerhavia erecta L. : an African medicinal plant, Master of Science - Research thesis, School of Chemistry, University of Wollongong, 2010. http://ro.uow.edu.au/theses/3674 Research Online is the open access institutional repository for the University of Wollongong. For further information contact the UOW Library: [email protected] Bioactive compounds from Boerhavia erecta L.: an African medicinal plant A thesis submitted in partial fulfilment of the requirements for the award of the degree Master of Science - Research from University of Wollongong by Ari Satia Nugraha, SF (GMU), GDipSc (UoW), Apt (GMU) School of Chemistry December 2009 ii Certification I, Ari Satia Nugraha, declare that this thesis, submitted in partial fulfilment of the requirements for the award of Master of Science-Research, in the School of Chemistry, University of Wollongong, is wholly my own work unless otherwise referenced or acknowledged. The document has not been submitted for qualifications at any other academic institution. Ari Satia Nugraha 17 December 2009 iii Acknowledgement I would like to give my sincere thanks to my supervisor, A/Prof. Paul A Keller, for guidance and support during the whole course of my study in the School of Chemistry University of Wollongong. My thanks also go to Prof. William E Price for his generous support in my study. Thanks are extended to Australian Development Scholarships (AusAID) for the financial support and the approval for MSc by research conversion. I would like to thanks to our collaborator, Dr. Adama Hilou, for providing plant samples. My utmost thanks go to the following people who provided their help in completing this work: Dr. Wilford Lie for training me to operate the NMR and the never ending NMR discussion; Dr. John Korth for his helps dealing with electron impact mass spectrometry; Dr. Thitima Urathamakul for the assistance to operate ESMS and MS2; Prof. Stephen G Pyne for the idea of acetylated natural products; Dr. Kittiya Somphol for her help on the HPLC and the friendship; Hayden Matthews for training using prep-HPLC; Sarah Murphy for her assistance in my early time in KRG lab and correcting my thesis; Melinda for correcting my written English; Other former and current KRG members (Rajee (in memoriam), Shane, Steve, Andrew, Mohammed, Aaron, Nick, Akash, Qing, Ashraf, Phillip, Verena for help and friendship. Finally, I would like to thanks to my beloved wife, Ira and my son, Abdee, for the support and their patience. The big family in Indonesia for the long distance support. iv Table of Contents List of Abbreviations .................................................................................................... vii Glossary of Botanical Terms ....................................................................................... viii Abstract ........................................................................................................................... ix Chapter 1 Introduction ..................................................................................................................... 1 1.1. African Traditional Medicine ................................................................................. 2 1.2. Antimicrobial Directed Screening on Tropical African Medicinal Plants ............. 4 1.3. Research on Boerhavia Genus Plants ..................................................................... 4 1.3.1. Boerhavia plumbaginea .................................................................................. 5 1.3.2. Boerhaavia chinensis ...................................................................................... 7 1.3.3. Boerhavia repens ............................................................................................ 7 1.3.4. Boerhaavia diffusa .......................................................................................... 9 1.3.5. Boerhavia erecta ........................................................................................... 17 1.4. Aims of The Research .......................................................................................... 19 Chapter 2 Isolation and Characterization of Sterols and Glycosides from Boerhavia erecta .. 21 2.1. Research Scheme ................................................................................................. 21 2.2. Isolation and Structure Elucidation of Less Polar Constituents from Boerhavia erecta ................................................................................................................... 23 2.2.1. LPF01 (β-Sitosterol) ..................................................................................... 24 2.2.2. LPF02 ............................................................................................................ 27 2.2.3. LPF03 and LPF04 ......................................................................................... 28 2.3. Isolation and Structure Elucidation of Polar Compounds from Boerhavia erecta ............................................................................................................................. 29 2.4.1. Isolate PF3.1 .................................................................................................. 32 2.4.2. Isolate PF3.2 .................................................................................................. 39 2.4.3. Isolate PF3.2a ................................................................................................ 42 2.4.4. Isolate PF3.3 .................................................................................................. 44 Chapter 3 Acetylation of PF3.1 ...................................................................................................... 51 3.1. General ................................................................................................................. 51 3.2. Synthesis .............................................................................................................. 51 v 3.3. Molecular Structure Elucidation .......................................................................... 51 Chapter 4 Bioactivity Testing Results ........................................................................................... 57 4.1. Introduction .......................................................................................................... 57 4.2. Anti-microbial Activity Testing ........................................................................... 57 4.3. Bio-testing Against HIV Infected Cells ............................................................... 57 4.4. Reported Anti-microbial Activities ...................................................................... 58 4.4.1. Isolate LPF01 (β-sitosterol, steroid type compound) .................................... 58 4.4.2. Isolate PF3.1 (~Rutin) and PF3.3 (~Isorhamnetin-3-O-rutinoside), Flavonoids .................................................................................................... 59 Chapter 5 Conclusion and Future Directions ............................................................................... 63 5.1. Conclusion ........................................................................................................... 63 5.2. Future work .......................................................................................................... 64 Chapter 6 Experimental ................................................................................................................. 65 6.1. General ................................................................................................................. 65 6.2. Plant Sample, Extraction and Re-extraction ........................................................ 67 6.2.1. Extraction of Stem Bark of Boerhavia erecta (SBBeL) ............................... 67 6.2.2. Extraction of Stem of Boerhavia erecta (SBeL) ........................................... 67 6.2.3. Re-extraction ................................................................................................. 67 6.3. Isolation and Purification ..................................................................................... 68 6.3.1. Isolation and Purification of Sterols from Boerhavia erecta ........................ 68 6.3.2. Isolation and Purification of Polar Constituents from Stem Bark of Boerhavia erecta (SBBeL). .......................................................................... 68 6.3.3. Isolation and Purification Polar Constituents from Stem of Boerhavia erecta (SBeL). ......................................................................................................... 69 6.4. Structure Elucidation............................................................................................ 70 6.4.1. The Less Polar Constituents .......................................................................... 70 6.4.2. Polar Constituents from Sub-fraction PF3 of SBeL...................................... 71 6.5. Acylated PF3.1 ..................................................................................................... 74 6.5.1. Semi-synthetic Procedure ............................................................................. 74 References .....................................................................................................................
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