Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596218
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Out of fashion plants at the “big data” Era: Illuminating the overlooked Apocynaceae alkaloids chemical space by Molecular Networking

MA Beniddir
1   BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France
,
AFE Ramos
1   BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France
,
EO N'nang
1   BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France
,
C Alcover
1   BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France
,
A Maciuk
1   BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France
,
L Evanno
1   BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France
,
E Poupon
1   BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France
,
P Champy
1   BioCIS, Univ. Paris-Sud, CNRS, Université Paris-Saclay, 92290 Châtenay-Malabry, France
› Author Affiliations
Further Information

Publication History

Publication Date:
14 December 2016 (online)

 
 

    The latest advances in bio-informatics and analytical chemistry, particularly in mass spectrometry, are totally revolutionizing the field of natural product discovery [1]. Indeed, when experimental data are combined to computational algorithms, a powerful synergy arises and enables to expedite the discovery process by predicting the structural identity of all detectable metabolites within complex natural extracts [2].

    Despite the fact that Apocynaceae plants were extensively studied since the beginning of phytochemistry in the 50's due to their content in alkaloids with major pharmacological activities, a thorough literature survey reveals that a considerable number of those early obtained compounds, has remained without biological evaluation neither assigned structure. Obviously, this is understandable given the striking molecular architecture complexity of those compounds. In this vein, as part of our continuing interest for monoterpenoid indole alkaloid chemistry [3], we decided to chemically reinvestigate the previously studied Apocynaceae plant, Picralima nitida, using molecular networking as a dereplication strategy [4]. By taking advantage from our historical laboratory's collections of natural monoterpenoid indole alkaloids, we used the above mentioned natural standards to seed the alkaloidic extract networks, in order to shed light on unexplored matter leading to prioritize the isolation workflow towards unknown compounds. Additionally, as the training set of natural standards possesses characterized biological attributes, their integration provided an early biological annotation of the networks. Satisfyingly, this study led to the identification of new compounds bearing unprecedented carbon skeleton and interesting biological activities. This presentation is intended to offer the promising perspectives gleaned from the reinvestigation of several forgotten plants by this new generation of sophisticated tools.

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    Acknowledgements: We are grateful to Karine Leblanc for the LC/MS assistance, and Jean-Christophe Jullian, Jean-François Gallard and Camille Dejean for NMR assistance.

    Keywords: Alkaloids, Apocynaceae, networking, mass, Geissospermum, Pleiocarpa, Picralima.

    References:

    [1] Medema MH, Fishback MA. Computational approaches to natural product discovery. Nat Chem Biol 2015; 11: 639 – 648

    [2] Kurita KL, Glassey E, Linington RG. Integration of high-content screening and untargeted metabolomics for comprehensive functional annotation of natural product librairies. Proc Natl Acad Sci USA 2015; 112: 11999 – 12004

    [3] Benayad S, Beniddir MA, Evanno L, Poupon E. Biomimetic assembly of leucoridine A. Eur J Org Chem 2015, 2015: 1894 – 1898. Beniddir MA, Martin MT, Dau METH, Grellier P, Rasoanaivo P, Guéritte F, Litaudon M. Goniomedines A and B: unprecedented bisindole alkaloids formed through fusion of two indole moieties via a dihydropyran unit. Org Lett 2012; 14: 4162 – 4165

    [4] Yang JY, Sanchez LM, Rath CM, Liu X, Boudreau PD, Bruns N, Glukhov E, Wodtke A, De felicio R, Fenner A, Wong WR, Linington RG, Zhang L, Debonsi HM, Gerwick WH, Dorrestein PC. Molecular networking as a dereplication strategy. J Nat Prod 2013; 76: 1686 – 1699


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    No conflict of interest has been declared by the author(s).

     
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