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THE CHEMOTAXONOMY and BIOLOGICAL ACTIVITY of SALVIASTENOPHYLLA(LAMIACEAE) and RELATED TAXA Angela Gono-Bwalya

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THE CHEMOTAXONOMY and BIOLOGICAL ACTIVITY of SALVIASTENOPHYLLA(LAMIACEAE) and RELATED TAXA Angela Gono-Bwalya THE CHEMOTAXONOMY AND BIOLOGICAL ACTIVITY OF SALVIASTENOPHYLLA (LAMIACEAE) AND RELATED TAXA £ •f * > •*« & ¥r .V\ P-. A t 1 . ' tlM* i I Angela Gono-Bwalya University of the Witwatersrand Faculty of Health Sciences A dissertation submitted to the Faculty of Health Sciences, University of the Witwatersrand, in fulfilment of the requirements for the degree o f Master of Medicine Johannesburg, South Africa, 2003. DECLARATION I, Angela Gono-Bwalya declare that this dissertation is my own work. It is being submitted for the degree of Master of Medicine in the University of the Witwatersrand, Johannesburg. It has not been submitted before for any degree or examination in any other University. 11 To my late parents Andrea Gono and Angeline Lisa Gono ABSTRACT Salvia stenophylla Burch, ex Benth. (Lamiaceae) is a perennial aromatic herb, which is widespread in the high altitude areas of the central and eastern parts of South Africa and also occurs in southwest Botswana and central Namibia. It is closely related to Salvia runcinata L. f. and Salvia repens Burch, ex Benth., with which it forms a species complex. The most recent revision of southern African Salvia species is that by Codd (1985). In this revision, the most important characters used in delimiting the three taxa were corolla size, calyx size and trichome density. As a result of intergrading morphological characters, the specific limits between the three taxa are not clear and positive identification of typical material is often difficult. Taxonomic delimitation through use of chemical characters was therefore the principle objective of this study. The taxa represented in this species complex are known in folk medicine and plant extracts have been used in the treatment of urticaria, body sores, and stomach ailments and as a disinfectant. S. stenophylla is reported to contain a-bisabolol, a compound that has anti-inflammatory properties. Based on the traditional uses of these plants and the international use of a-bisabolol to develop active cosmetic products, establishing a scientific rationale for the known uses was an important secondary objective. Plant material was collected from a total of 30 natural populations (10 populations of S. stenophylla; six of S. repens and 14 of X runcinata). Trichome studies were undertaken using scanning electron microscopy (SEM). The aerial parts of the plants were hydrodistilled to extract essential oil and analytical assessment of the oil was carried out using thin layer chromatography (TLC), gas chromatography (GC) and gas chromatography coupled to mass spectroscopy (GC/MS). Non-volatile compounds were extracted using methanol and analyzed by TLC and high performance liquid chromatography coupled to mass spectroscopy (HPLC/UV/MS). For the documentation of biological activity, antimicrobial activity was assessed by disc diffusion assay and the microplate dilution method. Antioxidant activity was assessed by TLC-DPPH and the anti­ inflammatory activity was performed by COX-2 radiometric assay. To investigate whether observed chemical variations were genotypic or phenotypic, seeds from selected populations were cultivated, harvested and distilled upon maturity. A molecular study attempted to evaluate genetic differences amongst individual plants and populations using the amplified fragment length polymorphism (AFLPs) technique. IV The SEM results did not reveal variation of the trichome types between the different taxa. TLC and GC/MS results showed variation in the qualitative and quantitative chemical composition within and between populations of the same and different taxa. The dominant compounds in S. stenophylla include; a-bisabolol (46.5%), limonene (38 1%), 5-3-carene (24.9%), y-terpinene (20.3%), p-cymene (18.4%) and (£)-nerolidol (53.6%). S. repens accumulated major compounds like (£)-nerolidol (25 2%), ledol (25 4%), camphor (12.7%), P-caryophyllene (13.6%) and P-phellandrene (22.2%). S. runcinata has (£)- nerolidol (72%), a-bisabolol (41.1%), limonene (24.1%), a-pinene (45%) and P-pinene (15%) and 26% of guaiol in high percentages, and three chemotypes were identified. The HPLC/UV/MS results revealed the occurrence of rosmarinic acid, carnosic acid, carnosol, isocarnosol and oleanolic acid derivatives in the methanol extracts analysed. This was also portrayed in the TLC-DPPH assay. The chemical variation was also expressed in the biological activity assays that were performed. S. stenophylla extracts exhibited high antibacterial activity against Gram-positive bacteria and the essential oils exhibited good anti-inflammatory activity. The AFLP results showed congruency with the chemical composition data as it supported the erratic chemical variations within the species complex. In view of all these results, we concluded that the three taxa are closely related with the existence of intermediates (hybrids) within the species complex. Furthermore, the essential data suggest that S. stenophylla and S. repern are the closest allies within the complex. v ACKNOWLEDGEMENTS Firstly, I would like to sincerely thank my supervisors, Dr A M Viljoen and Mr T. De Castro for their supervision and knowledge they impacted on me. The enthusiasm and interest towards the research encouraged me so much and for all the undivided time they put towards the completion of this research To my family, I sincerely thank my husband Gregory for allowing me pursue this study, for his patience, encouragement, prayers, moral support and his desire to see me complete this study. I also thank my brothers and sisters who checked on me regularly This study being a multidisciplinary project had a lot of input from many people of different fields and expertise. There are a number of laboratories we collaborated with, which 1 would like to thank for their facilities and staff who generously rendered support These laboratories include; 1. The Research Center for Plant Growth and Development, School of Botany and Zoology, University of Natal, Pietermaritzburg, Private bag X01, Scottsville 3209, where we performed the anti-inflammatory activity using the COX-2 assay. 2. The Medicinal and Aromatic Plant and Drug Research Center (TBAM), Anadolu University, 26470-Eski$ehir, Turkey. I would like to sincerely thank in particular Professor K.H.C Ba§er and Dr B. Demirci for their assistance and expertise in generating GC/MS results and for allowing me to use the microdistillation unit. 3. The Lesley Hill Laboratory at the Compton Herbarium, Kirstenbosch Research Centre, Newlands, Cape Town. I thank Dr Gail Reeves for her input towards the molecular study (AFLPs technique) and the hospitality 1 enjoyed at the research center. 4. Many thanks to Mr Chris van der Merwe who generously helped with the scanning electron microscopy (SEM) at the Laboratory for Microscopy and Micro Analysis, University of Pretoria. 5. Mr Paul Steenkamp for guidance with the HPLC/UV/MS analysis on the methanol extracts. 6. I thank Mr Tinus Fourie, who cultivated and looked after the plants at the Rand Afrikaans University. vi Sincere gratitude to Sandy van Vuuren for her generous time and knowledge that she gave for all the antibacterial assays. The understanding and tolerance she showed when I had very little knowledge of microbiological assays. Not forgetting all the staff and fellow students at the Department of Pharmacy and Pharmacology, University of the Witwatersrand, for their support. I would also like to thank the staff at C E Moss Herbarium, University of the Witwatersrand for their advice, encouragement and interest towards my study I thank all my friends for their prayers and support. Lastly, the support of the following sponsors is greatly acknowledged; SABONET, NRF, University of the Witwatersrand Research Committee and Robertet (France) Vll LIST OF FIGURES ] Salvia stenophylla habit ........................................................................................ 4 2 Salvia stenophylla flower......................................................................................4 3 Salvia repens h ab it................................................................................................ 4 4 Salvia repens flower .............................................................................................4 5 Salvia runcinata habit ...........................................................................................4 6 Salvia runcinata flow er........................................................................................ 4 7 Distribution map of Salvia stenophylla .............................................................5 8 Distribution map of Salvia repens .......................................................................5 9 Distribution map of Salvia runcinata .................................................................5 10 Distribution map of all the taxa from where plant material was collected for this study.........................................................................................................5 11 Chemical structures of the four a-bisabolol stereoisomers........................ 12 12 Commercial advertisements of a-bisabolol................................................. 13 13 Chemical structures of the four common non-volatile compounds in the genus Salvia...................................................................................................... 14 14 Hydrodistillation of plant material to obtain essential oil............................24 15 Microdistillation apparatus for small amounts of plant material..............
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