Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596249
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Molecular networking approach to detect new analogues of prenylated stilbenes from Macaranga spp.

T Péresse
1   Centre de Recherche de Gif, CNRS UPR 2301, Institut de Chimie des Substances Naturelles ICSN, Université Paris Saclay, 1 av de la Terrasse, 91198, Gif-sur-Yvette, France
,
PM Allard
2   Phytochemistry and bioactive natural products, University of Geneva, Quai Ernest Ansermet 30, CH-1211, Genève 4, Switzerland
,
JL Wolfender
2   Phytochemistry and bioactive natural products, University of Geneva, Quai Ernest Ansermet 30, CH-1211, Genève 4, Switzerland
,
VC Pham
3   Institut of Marine Biochemistry of the Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet Road, 90184 Cau Giay, Hanoi, Vietnam
,
DTM Huong
3   Institut of Marine Biochemistry of the Vietnamese Academy of Science and Technology, 18 Hoang Quoc Viet Road, 90184 Cau Giay, Hanoi, Vietnam
,
F Roussi
1   Centre de Recherche de Gif, CNRS UPR 2301, Institut de Chimie des Substances Naturelles ICSN, Université Paris Saclay, 1 av de la Terrasse, 91198, Gif-sur-Yvette, France
,
M Litaudon
1   Centre de Recherche de Gif, CNRS UPR 2301, Institut de Chimie des Substances Naturelles ICSN, Université Paris Saclay, 1 av de la Terrasse, 91198, Gif-sur-Yvette, France
› Author Affiliations
Further Information

Publication History

Publication Date:
14 December 2016 (online)

 

Phytochemical studies from Macaranga species led to the discovery of an interesting family of prenylated stilbenes having an original hexahydroxanthene moiety (Figure below), named schweinfurthins (SWF). Vedelianin, the first member of this chemical series was isolated from the leaves of Macaranga vedeliana, an endemic New Caledonian species[1]. Studying these molecules is of great interest since they display promising antiproliferative activities at low concentration (nM) for specific tumor-derived cell lines, such as glioblastoma[2].

Our project aims to discover new active analogues of these molecules among 20 species of Macaranga collected in various countries such as Madagascar, Vietnam, New Caledonia...

A molecular networking approach was set up to determine which species contain these molecules and to detect new analogues [3]. This LC/HRMS2-based methodology permitted us to select M. tanarius as the most interesting species, in which a new structurally close analogue of mappain could be detected (Figure below). Based on these results, we carried out a chemical study from an ethanolic extract of Macaranga tanarius fruits, affording various prenylated stilbenes including the new analogue previously detected.

Zoom Image

Acknowledgements to the International Associated Laboratory (LIA: NATPROCHEMLAB) between the Centre National de la Recherche Scientifique (CNRS-ICSN, France) and the Vietnam Academy of Science and Technology (Institute of Marine Biochemistry, VAST, Vietnam) which support the project. We are also grateful to the doctoral school “ Innovation therapeutique ” at Paris Saclay university for the PhD fellowship.

Keywords: Euphorbiaceae, Macaranga tanarius, schweinfurthins, molecular networking.

References:

[1] Thoison O, Hnawia E, Guéritte-Voegelein F, Sévenet T. Vedelianin, a Hexahydroxanthene Derivative Isolated from Macaranga Vedeliana. Phytochem 1992; 31: 1439 – 1442

[2] Beutler JA, Shoemaker RH, Johnson T, Boyd MR. Cytotoxic Geranyl Stilbenes from Macaranga Schweinfurthii. J Nat Prod 1998; 61: 1509 – 1512

[3] Allard PM, Péresse T, Bisson J, Gindro K, Marcourt L, Pham VC, Roussi F, Litaudon M, Wolfender JL. Integration of Molecular Networking and In-Silico MS/MS Fragmentation for Natural Products Dereplication. Anal Chem 2016; 88: 3317 – 3323