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Durham Research Online Durham Research Online Deposited in DRO: 10 June 2020 Version of attached le: Published Version Peer-review status of attached le: Peer-reviewed Citation for published item: Anderson, O. and Beckett, J. and Briggs, C.C. and Natrass, L.A. and Cranston, C.F. and Wilkinson, E.J. and Owen, J.H. and Williams, R.M. and Loukaidis, A. and Bouillon, M.E. and Pritchard, D. and Lahmann, M. and Baird, M.S. and Denny, P.W. (2020) 'An investigation of the antileishmanial properties of semi-synthetic saponin.', RSC medicinal chemistry. Further information on publisher's website: https://doi.org/10.1039/D0MD00123F Publisher's copyright statement: This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Additional information: Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: • a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full DRO policy for further details. Durham University Library, Stockton Road, Durham DH1 3LY, United Kingdom Tel : +44 (0)191 334 3042 | Fax : +44 (0)191 334 2971 http://dro.dur.ac.uk RSC Medicinal Chemistry View Article Online RESEARCH ARTICLE View Journal An investigation of the antileishmanial properties † Cite this: DOI: 10.1039/d0md00123f of semi-synthetic saponins Orlagh Anderson, ‡a Joseph Beckett,‡a Carla C. Briggs,‡a Liam A. Natrass,ab Charles F. Cranston, a Elizabeth J. Wilkinson,c Jack H. Owen,c Rhodri Mir Williams,c Angelos Loukaidis,c Marc E. Bouillon, c Deiniol Pritchard,d Martina Lahmann, c Mark S. Baird d and Paul W. Denny *a Leishmaniasis is a neglected tropical disease caused by insect-vector borne protozoan parasites of the, Leishmania species. Whilst infection threatens and affects millions of the global poor, vaccines are absent and drug therapy limited. Extensive efforts have recently been made to discover new leads from small molecule synthetic compound libraries held by industry; however, the number of new chemical entities identified and entering development as anti-leishmanials has been very low. This has led to increased interest in the possibility of discovering naturally derived compounds with potent antileishmanial activity Creative Commons Attribution-NonCommercial 3.0 Unported Licence. which may be developed towards clinical applications. Plant-derived triterpenoid and steroidal saponins have long been considered as anti-microbials and here we describe an investigation of a library of 137 natural (9) and semi-synthetic saponins (128) for activity against Leishmania mexicana, a causative agent of cutaneous leishmaniasis. The triterpenoid sapogenin, hederagenin, readily obtained in large quantities from Hedera helix (common ivy), was converted into a range of 128 derivatives. These semi-synthetic compounds, as well as saponins isolated from ivy, were examined with a phenotypic screening approach to identify potent and selective anti-leishmanial hits. This led to the identification of 12 compounds, including the natural saponin gypsogenin, demonstrating high potency (ED50 < 10.5 μM) against axenic L. Received 15th April 2020, mexicana amastigotes, the mammalian pathogenic form. One of these, hederagenin disuccinate, was This article is licensed under a Accepted 21st May 2020 sufficiently non-toxic to the macrophage host cell to facilitate further analyses, selectivity index (SI) > 10. Whilst this was not active in an infected cell model, the anti-leishmanial properties of hederagenin- DOI: 10.1039/d0md00123f derivatives have been demonstrated, and the possibility of improving the selectivity of natural hederagenin Open Access Article. Published on 09 June 2020. Downloaded 06/10/2020 15:46:14. rsc.li/medchem through chemical modification has been established. Introduction infection leading to a wide spectrum of disease, from self- healing but scarring cutaneous leishmaniasis (CL) to fatal Leishmaniasis is one of the 20 neglected tropical diseases visceral disease (VL). The diversity of disease is dependent on (NTD), and is endemic in over 90 countries, affecting the parasite species, genetic background and host immunity.3 approximately 12 million people per year, with over one billion Driven by elimination efforts in south Asia, the global burden people living at risk of disease.1 Causative Leishmania species of VL has decreased substantially in the past decade. However, are sand fly borne kinetoplastid protozoan parasites2 with in the same time period, CL cases have increased dramatically (0.7–1.0 million per year) largely due to forced migration in conflict zones.4 Against this backdrop, no vaccine is available a Department of Biosciences and Centre for Global Infectious Diseases, Durham and treatment relies entirely on a limited number of less than University, Stockton Road, Durham, DH1 3LE, UK. ideal drugs. Recently, public–private partnerships have seen E-mail: [email protected]; Tel: +44 (0)191 3343983 b industrial scale (>1 000 000) compound libraries screened for Department of Chemistry and Centre for Global Infectious Diseases, Durham 5,6 7 University, Stockton Road, Durham, DH1 3LE, UK anti-leishmanials either phenotypically or target-based. All c Department of Chemistry, School of Natural Science, Bangor University, Gwynedd, these initiatives focused on VL, leaving the most common form LL57 2UW, UK of leishmaniasis, CL, as a neglected NTD. Treatment of CL d Naturiol Bangor Ltd, Alun Roberts Building, Bangor University, Gwynedd, LL57 largely relies on the pentavalent antimonials – sodium 2UW, UK † Electronic supplementary information (ESI) available. See DOI: 10.1039/ stibogluconate (Pentostam) and meglumine antimoniate 8,9 d0md00123f (Glucantime). Both drugs have been in clinical use for over 10 ‡ Contributed equally to the work. 70 years despite their severe side-effects, parenteral This journal is © The Royal Society of Chemistry 2020 RSC Med. Chem. View Article Online Research Article RSC Medicinal Chemistry administration,11 and the emergence of drug resistance.12 Diamidine pentamidine13 and amphotericin B (Fungizone)14 are second-line CL drugs, but are similarly associated with severe side-effects and Leishmania resistance has been observed under laboratory conditions.15 The severe issues with the drugs used to treat CL demand the discovery and development of new effective therapies. Natural products are the basis of traditional ‘folk’ therapies, including for leishmaniasis.16,17 The active compounds from – these include chalcones,18 21 flavonoids,22,23 alkaloids24 and terpenoids.25,26 Further, the anti-leishmanial amphotericin B is a natural product polyene, which was isolated from Streptomyces nodosus as an antifungal in 1955.27 With Fig. 1 Short-hand structures for hederagenin and its benzyl ester (Bn- reference to this history, it is logical to revisit the natural Hed) with relevant numbering. world in the search for much needed anti-leishmanials.28 Saponins are a diverse class of compounds produced by many plants, and some marine organisms, via the mevalonic sapogenin, hederagenin. It is therefore of interest to acid pathway. They consist of an aglycone unit (sapogenin) determine whether the biological activity of these saponins, linked to between one and three carbohydrate moieties.29,30 and of hederagenin, can be optimised by simple chemical Depending on the nature of the sapogenin, saponins are modification to provide novel, plant based, solutions for divided into two main classes – triterpenoid and steroidal. application in medicine or agriculture. As part of a wider Triterpenoid saponins mainly occur in dicotyledonous study of chemically modified saponins, we now describe the Creative Commons Attribution-NonCommercial 3.0 Unported Licence. angiosperms and comprise sapogenin moieties of six evaluation of the anti-leishmanial effects of 128 semi- isoprene units, usually arranged as five rings, and bear synthetic molecules obtained by modification of the structurally diverse carbohydrate groups.31 The less varied hederagenin core, together with nine natural product and widespread steroidal saponins consist primarily of a five- controls isolated from ivy extracts. ring furostane or a six-ring spirostane skeleton and are almost exclusively produced by monocotyledonous Results and discussion angiosperms.32 The structural diversity of saponins is associated with a wide range of bioactivities. As secondary Compound screening scheme metabolites, their role in plants lies primarily in protection The library of hederagenin based compounds (137), either This article is licensed under a 29 from herbivory and pathogen attack. However, saponins isolated from Hedera helix or synthesised from hederagenin also possess a variety of pharmaceutical properties, from obtained by extraction and hydrolysis of ivy saponins, were anti-inflammatory and anti-cancer to vaccine adjuvant screened as illustrated in Fig. 2. Open Access Article. Published on 09 June 2020. Downloaded 06/10/2020 15:46:14. 33,34 activity. Several previous studies have identified saponins All available compounds were subjected to a primary 35–51 with anti-leishmanial activity. screen against mammalian stage L. mexicana axenic The beneficial effects of extracts from
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