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PHYTOCHEMICAL STUDIES ON CERTAIN SOUTH AFRICAN SPECIES OF THE RUTACEOUS GENERA AGATHOSMA WILLD. AND ZANTHOXYLUM L. A dissertation submitted to RHODES UNIVERSITY in partial fulfilment of the requirements for the degree of DOCTOR OF PHILOSOPHY by NATHAN FINKELSTEIN M.Sc., M.P.S. School of Pharmaceutlcal Sciences, Rhodes University, Grahamstown, Republic of South Africa. Decembe r, 1978. With esteem and gratitude this work is dedicated to my friend and former mentor, John M. CaZderwood. His interest afforded me the opportunity for academia advanaement, whiZe his inspiration evoked in me a Zove for naturaZ produat ahemistry. i i ACKNOWLEDGEHENTS This investigation was carried out in the Department of Chemistry, Rhodes University. The author wishes to express his sincere appreciation to Professor J. R. Nunn for making the necessary facilities available. Particular gratitude is also expres·sed to his supervisor, Professor D. E. A. Rivett, for his invaluable guidance, constant interest and inspiration throughout the study. The author is further indebted to: * Professor H. Parol Is and the lecturing staff of the Department of Chemistry for their helpful discussions and constructive suggestions; * Hr. A. W. Sonemann and the technical staff of the Department of Chemistry for their willing technica·l assistance; * Dr. A. Jacot Guillarmod and Hrs. E. Brink for the authentication of plant material, preparation of voucher specimens and advice on nomenclature; * Dr. I. C. Verdoorn and Hiss E. Retief of the Botanical Research Institute, Pretoria, for making available the facilities of the Institute's herbarium as well as useful botanical discussions; * Dr. P. G. Waterman of the Department of Pharmaceutical Chemistry, University of Strathclyde, Glasgow, Professor V. Deulofeu of the Universidad de Buenos Aires, Argentine, and Professor J. SlavIk of the Department of Hedical Chemistry, University J. E. Purkyn~, Czechoslovakia, for generous samples of authentic alkaloids and lignans; * Professor A. Cave and Dr. J. Vaquette of the Universite de Paris-Sud for their original spectra of· decarine; iii ,~ Mr. Gordon Young, Government Forester, Hogsback, for the collection and supply of plant material (Z. davyi(Verdoorn) Waterm.]; * Mr. M. J. Wells, Economic Botany Section, Botanical Research Institute, for arranging the collection and supply of plant material used in the Zantho~~um L. investigation; * Mrs. P. C. Estment for efficiently typing the final manuscript . Grateful appreciation for generous financial support is acknowledged to: * The Council for Sci"entific and Industrial Research; * The Foundation for Pharmaceutical Education; * Rhodes University; * Synthetico (Pty:) Ltd. iv CONTENTS Page Acknowledgements i i Contents iv List of tables, schemes and figures xi i Summary xi i j 1. INTRODUCTION 1.1 The plant family Rutaceae 2 1.2 The genus Agathosm2 Willd. 3 I • 2. I Phytochemical review 4 1.2.1.1 Volatile oil 4 1.2.1.2 Terpenoids 5 1.2.1.3 Sulphur compounds 7 1.2.1.4 Coumarins 8 1.2.1.5 Alkaloids 10 I .2.2 Chemotaxonomic aspects 10 1.3 The genus Zanthoxylum L. 12 1. 3. I Phytochemical review 18 1.3.1.1 Alkaloids 18 1.3.1.2 Lignans 22 1.3.1.3 Miscellaneous compounds 24 I . 3.2 Previous phytochemical studies on South African Zanthoxylum species 25 I .3.3 Medicinal properties 26 1. 3.4 Chemotaxonomy 28 2A. EXPERIMENTAL (AGATHOS~ WILLD. INVESTIGATION) 30 2A . I Preliminary extractions 30 v CONTENTS (continued) Page 2A. I . I Plant materials 30 2A.1.1.1 Agathosma puberuZa (Steud.) Fourc . 30 2A. 1. 1.2 Agathosma ovata (Thunb.) Pillans 30 2A. 1. 1.3 Agathosma apieuZata G. F. W. Mey 30 2A.I . I.4 Agathosma aZavisepaZa R. A. Dyer 31 2A. I .2 Drying and comminution 31 2A. 1. 3 Extraction 31 2A.2 Isolation and purification of crystalline material 32 2A.2.1 Small scale 32 2A.2.2 Large scale 32 2A.2.2 . 1 Fraction 8 33 2A . 2 . 2.2 Fractions 9 and 10 33 2A.2.3 "Alkal i-conversion" method 33 2A.3 Hydrogenation of puberul in 34 2A.4 Acetylation of "hydrogenated" puberulin 35 2A.5 Methylation of "hydrogenated" puberulin 36 2A.6 Ethylatlon of "hydrogenated" puberulin 36 2A.7 Prenylation of "hydrogenated" puberulin 37 2A . 8 Acid fission of ether linkage of puberulin 37 2B. EXPERIMENTAL (ZANTHOXYLUM L. INVESTIGATION) 38 2B. I Preliminary extractions 39 2B . 1. I Plant materials 39 2B.1.1.1 Zanthoxytum davyi (Verdoorn) Wate.rm. 39 2B.1.1.2 ZanthoxyZum thorncroftii (Verdoorn) \~aterm. 39 2B . 1.1.3 ZanthoxyZum humiZe (E. A. Bruce) Waterm. 40 2B. I .2 Drying and comminution 40 vi CONTENTS (continued) Page 2B.1.3 Extraction 40 2B.2 Isolation and characterization of compounds 41 2B.2.1 Z. davyi concentrated extracts 41 2B.2.1.1 n-Hexane extract of stem bark (ZO/SB1) 41 2B.2.1.1.1 Acetylation of lupeo1 42 2B.2.1.1.2 Benzoylation of lupeol 42 2B.2.1.1.3 Saponification of lupeol acetate 43 2B.2.1.2 Chloroform extract of stem bark (ZO/SB2) 43 2B.2.1.2.1 Yellowish precipitate (ypl) 43 2B.2.1.2.2 Chloroform fraction and washings (CFMI) 44 2B.2.1.2.3 Liquid-liquid extraction of combined acid filtrate (AF1) 44 2B.2.1.2.4 Conversion of crystals NF/3 to iodide salt 45 2B.2.1.3 Methanol extract of stem bark (ZO/SB3) 46 2B.2.1.3. I Horizontal cellulose chromatography of alkaloidal residue (R j ) 46 2B.2.1.3.2 Fractions - 8 47 2B.2.1.3.3 Fractions 9 - 17 47 2B.2.1.3.4 Fractions 18 - 32 47 2B.2.1.3.5 Fractions 33 and 34 47 2B.2.1.3.6 Fractions 35 - 51 48 2B.2.1.4 n-Hexane extract of root bark (ZO/RB1) 48 2B.2.1.4.1 Fraction 10 49 2B.2.1.4.2 Fractions 9 and 11 (bulked) 49 2B.2.1.4.3 . Fractions 12 and 13 (bulked) 50 2B.2.1.4.4 Acetylation of B-sitostero1 (NF/6) 50 2B.2.1.4.5 Fractions 14 - 16 (bulked) 51 2B.2.1.4.6 Fractions 17 - 36 51 vi j CONTENTS (continued) Page 2B.2.1.5 Chloroform extract of root bark (ZO/RB2) 51 2B.2.1.5. 1 Yellow deposit Y02 51 2B.2.1 . 5.2 Residue R2 51 2B.2 . 1. 5.3 Conversion of R2 to iodide salt 52 2B.2 . 1. 6 Methanol extract of root bark (ZO/RB3) 52 2B . 2. 2 Z. thorncroftii concentrated extracts 52 2B.2.2.1 Light petroleum (b.p.400-600) extract of root bark (ZT/RBJ) 52 2B . 2.2. 1.1 Orange precipitate (OPl) 53 2B.2.2.1 . 2 Combined acid filtrate (AF2) 53 2B . 2. 2. 1.3 Fractions P2 and P3 54 2B . 2.2.2 Chloroform extract of root bark (ZT/RB2) 54 2B.2.2. 2.1 Yellow precipitate (YP2) 54 2B . 2.2.2.2 Combined acid filtrate (AFJ) 55 2B . 2. 2. 2. 3 Column chromatography of remaining ZT/RB2 55 2B.2.2.2.4 Fractions 23 - 26 56 2B.2.2.2.5 Conversion of R3 to the hydrochloride 57 2B . 2.2.2.6 Acetylation of R3 58 2B.2 . 2.2.7 Methylation of R3 59 2B.2.2.2.8 Fraction 31 60 2B.2.2.2.9 Fraction 33 60 2B.2.2.2.10 Yellow insoluble solid (YP3) 60 2B.2 . 2.3 Methanol extract of root bark (ZT/RB3) 61 2B.2.2 . 3. I Low .pressure liquid chromatography of ZT/RB3 62 2B.2 . 2.3. 2 Fractions 57 - 66 63 2B.2.2.3. 3 Fractions 84 - 86 63 2B . 2.3 Z. humiZe concentrated extracts 64 2B.2 . 3. 1 Light petroleum (b . p. 40°- 60°) extract of root bark (ZH/RB1) 64 vii i CONTENTS (continued) Page 2B.2.3.1.1 Orange precipitate (OP2) 64 2B.2.3.1.2 Fractions 1 - 3 65 2B.2.3.1.3 Fractions 12 - 15 65 2B.2.3.1.4 Fractions 16 - 17 65 2B.2.3.1.5 Isolation of chelerythrlne chloride from OP2 66 2B.2.3.1.6 Combined acid filtrate (AF4) 67 2B.2.3.1.7 Low pressure liquid chromatography of E2 68 2B.2.3.1.8 Fractions 17 - 23 68 2B . 2 . 3. I • 9 Frae t 1on s 30 - 38 68 2B.2.3.I.l0 Fractions 50 - 59 69 28.2.3.2 Chloroform extract of root bark (ZH/RB2) 69 2B.2.3.2. I Fractions 19 - 23 (bulked) 70 2B.2.3.3 Methanol extract of root bark (ZH/RB3) 71 28.2.3.3.1 Conversion of candlclne chloride to Iodide salt 73 28.2.3.3.2 Column chromatography of R4 73 2B.2.3.3.3 Fraction 4 74 3A· DISCUSSION (AGATHOS~ WILLD. INVESTIGATION) 75 3A. I Coumarlns 75 3A.2 Extraction and purification of puberulln 76 3A.3 Locality of puberulln 76 3A.4 Structure elucidation of puberulln 77 3A.S Coumarlns with I.soprenold substltuents 84 38. DISCUSSION (ZANTHOXYLUM I.. INVESTIGATION) 88 3B.1 Preliminary extractions and separations 88 ix CONTENTS (continued) Page 3B. 1 . 1 Materials 88 3B.l . 2 Extraction 88 3B.2 Screening of concentrated extracts 89 3B.2.1 Alumina chromatograms 90 3B . 2.2 Silica Gel G chromatograms 90 3B.2. 3 Cellulose chromatograms 90 3B . 2.4 Detection of compounds 91 3B.3 Compounds isolated from Z. davyi extracts 92 3B.3.1 Stem bark extracts 92 3B . 3.1 .1 Concentrated n-hexane extract (lD/SB1) 92 Lupeol 93 3B .
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    South African Journal of Botany 87 (2013) 66–75 Contents lists available at SciVerse ScienceDirect South African Journal of Botany journal homepage: www.elsevier.com/locate/sajb Indigenous plant species used by Bapedi healers to treat sexually transmitted infections: Their distribution, harvesting, conservation and threats S.S. Semenya a,⁎, M.J. Potgieter a, L.J.C. Erasmus b a Department of Biodiversity, School of Molecular and Life Sciences, University of Limpopo, Private Bag X1106, Sovenga 0727, South Africa b Department of Physiology and Environmental Health, School of Molecular and Life Sciences, University of Limpopo, Private Bag X1106, Sovenga 0727, South Africa article info abstract Article history: An ethnobotanical survey on indigenous plant species used by Bapedi traditional healers to treat sexually Received 15 November 2012 transmitted infections was conducted in three districts of the Limpopo Province. Data was collected from 34 Received in revised form 11 February 2013 traditional healers via a semi-structured questionnaire, supplemented by field observations. Results showed Accepted 4 March 2013 that 37 species from 33 genera belonging to 24 families, mostly Asteraceae (10.8%), Asphodelaceae, Fabaceae Available online 16 April 2013 and Hyacinthaceae (8.1%, each) are used to treat STIs such as chlamydia, gonorrhoea, HIV/AIDS, syphilis and — Edited by J Van Staden other STIs (nta Bapedi terminology). The vast majority (90%) of these species were harvested from commu- nal lands. Entire plants (10.2%) and underground parts such as roots (61.5%), bulbs (10.2%) and tubers (7.6%) Keywords: were mostly harvested. All species recorded in this study appear on the South African National Red Data List.
  • Tuberculosis: History, Epidemiology, Antitubercular Drugs and Plant-Based Alternatives

    Tuberculosis: History, Epidemiology, Antitubercular Drugs and Plant-Based Alternatives

    Review Article Tuberculosis: History, Epidemiology, Antitubercular Drugs and Plant-based Alternatives B. TIWARI*, SUNITA SHAILAJAN1, S. MENON2 AND SAVITA KULKARNI3 Enaltec Labs Pvt. Ltd., Analytical Research and Development Department, Plot No. W-59A, Anand Nagar, Additional MIDC, Ambernath-421 506, 1Herbal Research Laboratory, Ramnarain Ruia College, Matunga-400 019, 2Institute for Advanced Training and Research in Interdisciplinary Sciences, TDM Laboratory, Sion (East)-400 022, 3Radiation Medicine Centre, Bio- Medical Group, Bhabha Atomic Research Centre, Trombay-400 085, Mumbai, India Tiwari, et al.: A Brief Review on Tuberculosis The article is a brief review on certain important aspects of tuberculosis. A good number of medicinal plants and their chemical constituents are reported to have antimycobacterial activity comparable to the existing antitubercular drugs or sometimes even better in efficacy. The present review covers the literature published concerning medicinal plants and plant-based active constituents showing both immunomodulatory and antimycobacterial activity. These plants might eventually be studied and screened with a well-defined strategy to develop effective new drugs against tuberculosis. Key words: Tuberculosis, chemotherapy, immunotherapy, alternative therapy Millions of people of all age groups die each year is essential to find new drugs that allow better control of worldwide from diseases such as chest and respiratory TB. In the present review, various aspects of TB were disorders, bacteraemia, wound suppuration, diarrhoea, covered along with pharmacological information on dysentery and tuberculosis (TB). Additionally, millions 11 medicinal plants and 11 phytochemical suffer from several long-standing chronic infections constituents with potential immunomodulatory and such as TB[1]. TB is characterized as a chronic bacterial antimycobacterial activities.

  • Zimbabwe-Mozambique)

    A peer-reviewed open-access journal PhytoKeys 145: 93–129 (2020) Plant checklist for the Bvumba Mountains 93 doi: 10.3897/phytokeys.145.49257 RESEARCH ARTICLE http://phytokeys.pensoft.net Launched to accelerate biodiversity research Mountains of the Mist: A first plant checklist for the Bvumba Mountains, Manica Highlands (Zimbabwe-Mozambique) Jonathan Timberlake1, Petra Ballings2,3, João de Deus Vidal Jr4, Bart Wursten2, Mark Hyde2, Anthony Mapaura4,5, Susan Childes6, Meg Coates Palgrave2, Vincent Ralph Clark4 1 Biodiversity Foundation for Africa, 30 Warren Lane, East Dean, E. Sussex, BN20 0EW, UK 2 Flora of Zimbabwe & Flora of Mozambique projects, 29 Harry Pichanick Drive, Alexandra Park, Harare, Zimbabwe 3 Meise Botanic Garden, Bouchout Domain, Nieuwelaan 38, 1860, Meise, Belgium 4 Afromontane Research Unit & Department of Geography, University of the Free State, Phuthaditjhaba, South Africa 5 National Her- barium of Zimbabwe, Box A889, Avondale, Harare, Zimbabwe 6 Box BW53 Borrowdale, Harare, Zimbabwe Corresponding author: Vincent Ralph Clark ([email protected]) Academic editor: R. Riina | Received 10 December 2019 | Accepted 18 February 2020 | Published 10 April 2020 Citation: Timberlake J, Ballings P, Vidal Jr JD, Wursten B, Hyde M, Mapaura A, Childes S, Palgrave MC, Clark VR (2020) Mountains of the Mist: A first plant checklist for the Bvumba Mountains, Manica Highlands (Zimbabwe- Mozambique). PhytoKeys 145: 93–129. https://doi.org/10.3897/phytokeys.145.49257 Abstract The first comprehensive plant checklist for the Bvumba massif, situated in the Manica Highlands along the Zimbabwe-Mozambique border, is presented. Although covering only 276 km2, the flora is rich with 1250 taxa (1127 native taxa and 123 naturalised introductions).