Studies Related to the Synthesis of Bisindole
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A Review on Tabernaemontana Spp.: Multipotential Medicinal Plant
Online - 2455-3891 Vol 11, Issue 5, 2018 Print - 0974-2441 Review Article A REVIEW ON TABERNAEMONTANA SPP.: MULTIPOTENTIAL MEDICINAL PLANT ANAN ATHIPORNCHAI* Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Burapha University, Bangsaen, Chonburi 20131 Thailand. Email: [email protected] Received: 01 March 2016, Revised and Accepted: 29 January 2018 ABSTRACT Plants in the genus Tabernaemontana have been using in Thai and Chinese traditional medicine for the treatment several diseases. The great majority constituents of Tabernaemontana species have already been subjected to isolation and identification of monoterpene indole alkaloids present in their several parts. Many of monoterpene indole alkaloids exhibited a wide array of several activities. The biogenesis, classification, and biological activities of these alkaloids which found in Tabernaemontana plants were discussed in this review and its brings the research up-to-date on the bioactive compounds produced by Tabernaemontana species, directly or indirectly related to human health. Keywords: Tabernaemontana plants, Phytochemistry, Biogenesis, Terpene indole alkaloids, Biological activities. © 2018 The Authors. Published by Innovare Academic Sciences Pvt Ltd. This is an open access article under the CC BY license (http://creativecommons. org/licenses/by/4. 0/) DOI: http://dx.doi.org/10.22159/ajpcr.2018.v11i5.11478 INTRODUCTION alkaloids are investigated. All monoterpene indole alkaloids are derived from aromatic amino acid tryptophan and the iridoid terpene Several already drugs were discovered from the natural products. secologanin (Scheme 1). Tryptophan converts to tryptamine using Especially, the treatments of infectious diseases and oncology have tryptophan decarboxylase which is a pyridoxal-dependent enzyme. benefited from numerous drugs which were found in natural product The specific iridoid precursor was subsequently identified as sources. -
The Iboga Alkaloids
The Iboga Alkaloids Catherine Lavaud and Georges Massiot Contents 1 Introduction ................................................................................. 90 2 Biosynthesis ................................................................................. 92 3 Structural Elucidation and Reactivity ...................................................... 93 4 New Molecules .............................................................................. 97 4.1 Monomers ............................................................................. 99 4.1.1 Ibogamine and Coronaridine Derivatives .................................... 99 4.1.2 3-Alkyl- or 3-Oxo-ibogamine/-coronaridine Derivatives . 102 4.1.3 5- and/or 6-Oxo-ibogamine/-coronaridine Derivatives ...................... 104 4.1.4 Rearranged Ibogamine/Coronaridine Alkaloids .. ........................... 105 4.1.5 Catharanthine and Pseudoeburnamonine Derivatives .. .. .. ... .. ... .. .. ... .. 106 4.1.6 Miscellaneous Representatives and Another Enigma . ..................... 107 4.2 Dimers ................................................................................. 108 4.2.1 Bisindoles with an Ibogamine Moiety ....................................... 110 4.2.2 Bisindoles with a Voacangine (10-Methoxy-coronaridine) Moiety ........ 111 4.2.3 Bisindoles with an Isovoacangine (11-Methoxy-coronaridine) Moiety . 111 4.2.4 Bisindoles with an Iboga-Indolenine or Rearranged Moiety ................ 116 4.2.5 Bisindoles with a Chippiine Moiety ... ..................................... -
Uses of Voaca Nga Species
USES OF VOACA NGA SPECIES N.G.BISSET PharmacognosyResearch Laboratories, Department of Pharmacy, Chelsea College, Universityof London, Manresa Road, London SW36LX Received4-II-198 5 Dateo fPublicatio n 16-VIII-1985 INTRODUCTION None of the species of the genus has attained any widespread application and evenV. afriLa, the one with the greatest distribution range and the one to which most of the uses described apply, has rather tainted localu e..A few ofti e medicinalapplication s appear to reflect theactivxt.e so fth ealkaloid spre - luntoriEnte (cf. Phytochemistry,Sectio n 3).Th efollowin g paragraphsgiv e aSoutline ox the uses which have been reported in the literature and as annotations on specimenskep ti nth eherbari a listedo np .00 . 1. THE PLANTS 1.1. V.AFRICANA (ANGUSTIFOLIA ?,LUTESCENS, PUBERULA) West Africa: The latex is said to be a rubber adul^t^dU i^put into acariou s tooth (Dalziel, 1937).Th e plant xs reported tob euse dm treatin g scabies (Janot and Goutarel, 1955).Senegal :Th e^amnk a (or Serere^) eat the fruit; theytrea t woundswit hth elatex .Th eplan tx sals oco n^ *obea pan a cea - the leafy branches are put into baths morning and ev«J^d a ^. prepared from them is given to people affected ^r^^S^ss. tierx of the leaves isdrun k as a tonic and against fatigue due^ obr«h^n Inth eCasamanc ea decoctio n ofth eroot stake nthre etime sdad y« . ecomme ed for women to counteract the effects of premature and rapid birth it » a 19 giveninternall y for hernial pain (Kerharo and Adam, ^' ^^hoca; Theleave shav esevera luses :A decoctio ni sapplie da sa wash •aganistduur t , it is put into baths against generalized oedema; it xs, utxhzea a fnction in a drink in the treatment of leprosy; a lotion is ^^^^ (possibly in children; and the juice is placed in the nostrlis oca^.^ Zernal v0 through confusion with other Apocynaceae- *«"* ™""£ °ossibly used -—^(Bouquetand^^ l for adulterating rubber (F. -
Regulation of Alkaloid Biosynthesis in Plants
CONTRIBUTORS Numbers in parentheses indicate the pages on which the authors’ contributions begin. JAUME BASTIDA (87), Departament de Productes Naturals, Facultat de Farma` cia, Universitat de Barcelona, 08028 Barcelona, Spain YEUN-MUN CHOO (181), Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia PETER J. FACCHINI (1), Department of Biological Sciences, University of Calgary, Calgary, AB, Canada TOH-SEOK KAM (181), Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia RODOLFO LAVILLA (87), Parc Cientı´fic de Barcelona, Universitat de Barcelona, 08028 Barcelona, Spain DANIEL G. PANACCIONE (45), Division of Plant and Soil Sciences, West Virginia University, Morgantown, WV 26506-6108, USA CHRISTOPHER L. SCHARDL (45), Department of Plant Pathology, University of Kentucky, Lexington, KY 40546-0312, USA PAUL TUDZYNSKI (45), Institut fu¨r Botanik, Westfa¨lische Wilhelms Universita¨tMu¨nster, Mu¨nster D-48149, Germany FRANCESC VILADOMAT (87), Departament de Productes Naturals, Facultat de Farma` cia, Universitat de Barcelona, 08028 Barcelona, Spain vii PREFACE This volume of The Alkaloids: Chemistry and Biology is comprised of four very different chapters; a reflection of the diverse facets that comprise the study of alkaloids today. As awareness of the global need for natural products which can be made available as drugs on a sustainable basis increases, so it has become increas- ingly important that there is a full understanding of how key metabolic pathways can be optimized. At the same time, it remains important to find new biologically active alkaloids and to elucidate the mechanisms of action of those that do show potentially useful or novel biological effects. Facchini, in Chapter 1, reviews the significant studies that have been conducted with respect to how the formation of alkaloids in their various diverse sources are regulated at the molecular level. -
Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Varicose Veins
Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Varicose Veins Chemical Activity Count (+)-ALLOMATRINE 1 (+)-ALPHA-VINIFERIN 1 (+)-CATECHIN 7 (+)-EUDESMA-4(14),7(11)-DIENE-3-ONE 1 (+)-GALLOCATECHIN 2 (+)-HERNANDEZINE 1 (+)-ISOCORYDINE 1 (+)-PRAERUPTORUM-A 1 (+)-PSEUDOEPHEDRINE 1 (+)-SYRINGARESINOL 1 (-)-16,17-DIHYDROXY-16BETA-KAURAN-19-OIC 1 (-)-ACETOXYCOLLININ 1 (-)-ALPHA-BISABOLOL 2 (-)-ARGEMONINE 1 (-)-BETONICINE 1 (-)-BISPARTHENOLIDINE 1 (-)-BORNYL-CAFFEATE 2 (-)-BORNYL-FERULATE 2 (-)-BORNYL-P-COUMARATE 2 (-)-DICENTRINE 1 (-)-EPIAFZELECHIN 1 (-)-EPICATECHIN 3 (-)-EPICATECHIN-3-O-GALLATE 1 (-)-EPIGALLOCATECHIN 1 (-)-EPIGALLOCATECHIN-3-O-GALLATE 2 (-)-EPIGALLOCATECHIN-GALLATE 3 (-)-HYDROXYJASMONIC-ACID 1 Chemical Activity Count (-)-N-(1'-DEOXY-1'-D-FRUCTOPYRANOSYL)-S-ALLYL-L-CYSTEINE-SULFOXIDE 1 (1'S)-1'-ACETOXYCHAVICOL-ACETATE 2 (15:1)-CARDANOL 1 (2R)-(12Z,15Z)-2-HYDROXY-4-OXOHENEICOSA-12,15-DIEN-1-YL-ACETATE 1 (7R,10R)-CAROTA-1,4-DIENALDEHYDE 1 (E)-4-(3',4'-DIMETHOXYPHENYL)-BUT-3-EN-OL 2 1,2,6-TRI-O-GALLOYL-BETA-D-GLUCOSE 1 1,7-BIS(3,4-DIHYDROXYPHENYL)HEPTA-4E,6E-DIEN-3-ONE 1 1,7-BIS(4-HYDROXY-3-METHOXYPHENYL)-1,6-HEPTADIEN-3,5-DIONE 1 1,7-BIS-(4-HYDROXYPHENYL)-1,4,6-HEPTATRIEN-3-ONE 1 1,8-CINEOLE 3 1-(METHYLSULFINYL)-PROPYL-METHYL-DISULFIDE 1 1-O-(2,3,4-TRIHYDROXY-3-METHYL)-BUTYL-6-O-FERULOYL-BETA-D-GLUCOPYRANOSIDE 1 10-ACETOXY-8-HYDROXY-9-ISOBUTYLOXY-6-METHOXYTHYMOL 2 10-DEHYDROGINGERDIONE 1 10-GINGERDIONE 1 11-HYDROXY-DELTA-8-THC 1 11-HYDROXY-DELTA-9-THC 1 12,118-BINARINGIN 1 12-ACETYLDEHYDROLUCICULINE -
THE Moga and VOACANGA ALKALOIDS
--CHAPTER 9-- THE mOGA AND VOACANGA ALKALOIDS W. 1. TAYLOR Research Department,OIBA Pharmaceutical Oompany, Division of OIBA Oorporation, Summit, New Jersey I. The Iboga Alkaloids. ... .... .... ..... ....... .. .. .. .. 203 A. The Structures of Ibogaine and Iboxygaine. ... ...... ...... 206 B. Ibogamine and Tabernanthine... .. .. .. .. .. .. .. .... .. .. .. .... 213 C. 18-Carbomethoxy Alkaloids _. .. 213 D. Voacryptine.. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. 217 E. Catharanthine, Cleavamine, and Velbanamine.. .. .. .. .. .. .. .. .. .. .. .. 218 F. Mass Spectra of Iboga Alkaloids.. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .. .... 221 G. Other Alkaloids.. .. .. .. .. .. .. .. 223 II. The Voacanga Alkaloids. ........................ 225 A. Voachalotine .... .... .. .. .. .................. ... 225 B. Vobasine, Dregamine, Tabernaemontanine, and Callichiline....... .. .. .. 228 C. Bisindoles....................................................... 229 III. Miscellaneous.. ..... .. ... .... .. .. .. .. .. 231 References _... ... .... .. .. .... .. ..... ... .... 233 I. The Ihoga Alkaloids The iboga alkaloids (Table I) presently number twelve, if their oxida- tion products are excluded, all from apocynaceous plants of the genera Oonopharyngia (Plumeria), Ervatamia, Gabunea, Stemmadenia, Taber- naemontana, Voacanga, Vinca (Lochnera, Oatharanthus), and Tabernanthe. It was from the last genus that the parent pentacyclic heterocycle, ibogamine, was first obtained. The structures of these compounds depend entirely -
PCT/US2020/0393 12 (22) International Filing Da
( (51) International Patent Classification: A61K 31/55 (2006.01) (21) International Application Number: PCT/US2020/0393 12 (22) International Filing Date: 24 June 2020 (24.06.2020) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 62/865,5 14 24 June 2019 (24.06.2019) US (71) Applicant: CAAMTECH LLC [US/US]; 58 E . Sunset Way, Suite 208, Issaquah, WA 98027 (US). (72) Inventor: CHADEAYNE, Andrew, R.; 13200 Squak Mt. Road S.E., Issaquah, WA 98027 (US). (74) Agent: LINDEMAN, Jeffrey, A.; J.A.lindeman & Co., PLLC, 3190 Fairview Park Drive, Suite 1070, Falls Church, VA 22042 (US). (81) Designated States (unless otherwise indicated, for every kind of national protection available) : AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, WS, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available) : ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, Cl, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). -
Alkaloids – Secrets of Life
ALKALOIDS – SECRETS OF LIFE ALKALOID CHEMISTRY, BIOLOGICAL SIGNIFICANCE, APPLICATIONS AND ECOLOGICAL ROLE This page intentionally left blank ALKALOIDS – SECRETS OF LIFE ALKALOID CHEMISTRY, BIOLOGICAL SIGNIFICANCE, APPLICATIONS AND ECOLOGICAL ROLE Tadeusz Aniszewski Associate Professor in Applied Botany Senior Lecturer Research and Teaching Laboratory of Applied Botany Faculty of Biosciences University of Joensuu Joensuu Finland Amsterdam • Boston • Heidelberg • London • New York • Oxford • Paris San Diego • San Francisco • Singapore • Sydney • Tokyo Elsevier Radarweg 29, PO Box 211, 1000 AE Amsterdam, The Netherlands The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, UK First edition 2007 Copyright © 2007 Elsevier B.V. All rights reserved No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means electronic, mechanical, photocopying, recording or otherwise without the prior written permission of the publisher Permissions may be sought directly from Elsevier’s Science & Technology Rights Department in Oxford, UK: phone (+44) (0) 1865 843830; fax (+44) (0) 1865 853333; email: [email protected]. Alternatively you can submit your request online by visiting the Elsevier web site at http://elsevier.com/locate/permissions, and selecting Obtaining permission to use Elsevier material Notice No responsibility is assumed by the publisher for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation -
Part I. the Reactions of 2-Oximino-Cholesta-4, 6-Diene-3
This dissertation has been microfilmed exactly as received ® 7-2401 AHMED, Quazi Anwaruddin, 1938- PART I. THE REACTIONS OF 2-OXIMINO-CHOLESTA-4,6-DIENE-3-ONE. PART n. THE ALKALOIDAL CONSTITUENTS OF TABERNAEMONTANA RIGIDA. The Ohio State University, Ph.D„ 1966 Chemistry, organic University Microfilms, Inc., Ann Arbor, Michigan PART I THE REACTIONS OP 2-0XIMIN0-CH0LESTA-^,6-DIENE-3-0NE PART I I THE ALKALOIDAL CONSTITUENTS OP TABERNAEMONTANA RIGIDA DISSERTATION Presented in Partial Pulfillment of the Requirements for the Degree of Philosophy in the Graduate School of the Ohio S tate U niversity By Quazi Anwaruddin Ahmed, B .Sc..(Honours), M.Sc, ****** The Ohio State U niversity 1966 Approved by Adviser Department of Chemistry ACKNOWLEDGMENTS I wish to express my sincere thanks and appreciation to Professor Michael P. Cava for the guidance and encourage ment received during the course of these problems' and to Dr. G. Praenkel for acting as a temporary adviser. I am indebted to Dr. B. H. Bhat for many helpful dis cussions both in and outside the laboratory. I also thanlc Dr. ,M. J. Mitchell, Dr. K. V. Rao and.Dr. K. Bessho for their helpful suggestions. Lastly, I owe a debt of gratitude to my parents-and most esp ecially to my wife Verena,. l i VITA September 1938 Born - Rajshahi, East Pakistan November, 1958 B. Sc. (Hons.) in Chemistry, Dacca Uni versity, Dacca, East Palcistan November,, 1959 M. Sc. (Thesis Gr.) in Chemistry, Dacca University, Dacca, East Pakistan 1961-1963 . Teaching Assistant, Department of Chemis try , The Ohio S tate U niversity, Columbus, Ohio 1961+-1966 . -
Phytochemical Analysis of Tabernaemontana Divaricata
Journal of Pharmacognosy and Phytochemistry 2020; 9(2): 1283-1291 E-ISSN: 2278-4136 P-ISSN: 2349-8234 www.phytojournal.com Phytochemical analysis of Tabernaemontana JPP 2020; 9(2): 1283-1291 Received: 19-01-2020 divaricata Accepted: 21-02-2020 Bindu Rathaur Bindu Rathaur, Meraj Ali, Sumit Kumar and Urmila Nishad S.B.S. Dadduji College of Pharmacy Fatehgarh, Farrukhabad, Uttar Pradesh, India Abstract Objectives Meraj Ali 1. Procurement of Raw Material: Collection of part of plant in which alkaloids are present in great Gaya Prasad Institute Human Excellence for Pharmacy Malihabad, concentration like roots, flowers, seeds, barks, fruits etc. Lucknow, Uttar Parades, India 2. Extraction and Fractionation: Extraction can be done by using different techniques like Percolation and Soxhlet Extraction and Fractionation by using Column Chromatography. Sumit Kumar 3. Isolation and Characterization S.B.S. Dadduji College of Pharmacy Fatehgarh, Farrukhabad, 4. These isolation and Characterization can be done by using TLC and Column Chromatography. Uttar Pradesh, India 5. Standardization The standardization of crude drug materials includes the following steps 1. Authentication (Stage of collection, Parts of the plant collected, Regional status, Botanical identity Urmila Nishad like Phytomorphology microscopically and Histological analysis, Taxonomical identity, etc.) Gaya Prasad Institute Human Excellence for Pharmacy Malihabad, 2. Chromatographic and spectroscopic evaluation. TLC, HPTLC, HPLC methods will provide Lucknow, Uttar Parades, India qualitative and semi quantitative information about the main active constituents present in the crude drug as chemical markers in the TLC fingerprint evaluation of herbals (FEH). The quality of the drug can also be assessed on the basis of the chromatographic fingerprint. -
PHCOG REV. : Plant Review Phytochemical Survey and Pharmacological Activities of the Indole Alkaloids in the Genus Voacanga Thouars (Apocynaceae) – an Update
Phcog Rev. Vol, 3, Issue 5, 143-153, 2009 Available Online : www.phcogrev.com PHCOG REV. : Plant Review Phytochemical Survey and Pharmacological Activities of the Indole Alkaloids in the Genus Voacanga Thouars (Apocynaceae) – An Update Allan Patrick G. Macabeo,1,3* Grecebio Jonathan D. Alejandro 2, Arnold V. Hallare 4, Warren S. Vidar 1, Oliver B. Villaflores 1 1Phytochemistry and 2Plant Sciences, Research Center for the Natural Sciences, University of Santo Tomas, Espana Blvd, Manila 1015 Philippines 3Institut für Organische Chemie, Universität Regensburg, Universitätsstraße 31, D-93053 Regensburg, Germany 4Department of Biology, CAS, University of the Philippines-Manila, Padre Faura St., Manila 1000 Philippines *Corresponding author: Phone: +499419434631 E-mail: [email protected]/[email protected] ABSTRACT Numerous species of the Apocynaceous genus Voacanga Thouars have been demonstrated to elaborate a host of indole alkaloids that display various structural complexities and a wide array of biological activities. Monoterpenoid indole alkaloids are nitrogenous metabolites borne from the biosynthetic union of tryptophan and the terpene-derived iridoid, secologanin. As a genus is closely related to Tabernaemontana , representative species of Voacanga were reported to contain the vobasine, vallesamine, eburnane, iboga and aspidosperma–type indole alkaloids. A lot of these compounds are associated with analgesic, CNS, antimicrobial, anti-ulcer, cytotoxic, antioxidant and antimalarial activities. Voacanga is a small taxon with 12 species that are mainly found in tropical Africa and Malesia except for V. grandifolia which extends to Australia. This comprehensive review compiles the phytochemical and pharmacological explorations that have been undertaken on Voacanga in relation to its indole alkaloids. -
Bioactive Alkaloids from Medicinal Plants of Lombok Surya Hadi University of Wollongong
University of Wollongong Research Online University of Wollongong Thesis Collection University of Wollongong Thesis Collections 2002 Bioactive alkaloids from medicinal plants of Lombok Surya Hadi University of Wollongong Recommended Citation Hadi, Surya, Bioactive alkaloids from medicinal plants of Lombok, Doctor of Philosophy thesis, Department of Chemistry, University of Wollongong, 2002. http://ro.uow.edu.au/theses/1117 Research Online is the open access institutional repository for the University of Wollongong. For further information contact the UOW Library: [email protected] BIOACTIVE ALKALOIDS FROM MEDICINAL PLANTS OF LOMBOK A Thesis Submitted in Fulfillment ofthe Requirements for the Award ofthe Degree of DOCTOR OF PHILOSOPHY from The University of Wollongong by SURYA HADI, Ir. M.Sc. (Hons.) Department of Chemistry October 2002 CERTIFICATION I, Surya Hadi, declare that this thesis, submitted in fulfillment of requirement for the award of Doctor of Philosophy, in the Department of Chemistry, University of Wollongong, is wholly my own work unless otherwise referenced or acknowledge. The document has not been submitted for qualifications at any other academic institution. SURYA HADI 10 October 2002 u PUBLICATIONS 1. Initial Studies on Alkaloids from Lombok Medicinal Plants (Molecules)1 2. Constituents of Medicinal Plants of Lombok: A New Antibacterial Alkaloid from Voacangafoetida (Bl.) Rolfe (Phytochernistry, in preparation) 3. New Bioactive Alkaloids from Young Trees of Alstonia scholaris R. Br. (Planta Medica, in preparation) (1) Hadi, S.; Bremner, J. B. Initial studies on alkaloids from Lombok medicinal plants. Molecules [online computer file] 2001, 6, 117-129. Ill ACKNOWLEDGEMENTS I would like to give my sincere thanks to my supervisor, Prof.