Chemical diversity and antiviral potential in the pantropical Diospyros genus

被引:19
作者
Peyrat, Laure-Anne [1 ]
Eparvier, Veronique [1 ]
Eydoux, Cecilia [2 ]
Guillemot, Jean-Claude [2 ]
Stien, Didier [1 ,3 ]
Litaudon, Marc [1 ]
机构
[1] Univ Paris Saclay, CNRS, Inst Chim Subst Nat, UPR2301, F-91198 Gif Sur Yvette, France
[2] Aix Marseille Univ, Ctr Rech Architecture & Fonct Macromol Biol, CNRS, UMR 7257, 163 Ave Luminy, F-13288 Marseille, France
[3] Univ Paris 06, Sorbonne Univ, CNRS, LBBM,Observ Oceanolog, F-66650 Banyuls Sur Mer, France
关键词
Diospyros spp; Diospyros glans; Ebenaceae; Dengue virus; Triterpenoids; MZmine; BETULINIC ACID; DERIVATIVES; INHIBITORS; CONSTITUENTS; EBENACEAE; EXTRACTS; PLANTS;
D O I
10.1016/j.fitote.2016.04.017
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A screening using a dengue replicon virus-cell-based assay was performed on 3563 ethyl acetate (EtOAc) extracts from different parts of 1500 plants. The screening led to the selection of species from the genus Diospyros (Ebenaceae), among which 25 species distributed in tropical areas showed significant inhibitory activity on dengue virus replication. A metabolic analysis was conducted from the UPLC-HRMS profiles of 33 biologically active and inactive plant extracts, and their metabolic proximity is presented in the form of a dendrogram. The results of the study showed that chemical similarity is not related to plant species or organ. Overall, metabolomic profiling allowed us to define large groups of extracts, comprising both active and inactive ones. Closely related profiles from active extracts might indicate that the common major components of these extracts were responsible for the antiviral activity, while the comparison of chemically similar active and-inactive extracts, will permit to find compounds of interest. Eventually, the phytochemical investigation of Diospyros glans bark EtOAc extract afforded usnic acid and 7 known ursane- and lupane-type triterpenoids, among which 5 were found significantly active against dengue virus replication. The inhibitory potency of these compounds was also evaluated on a DENV-NS5 RNA-dependant RNA polymerase assay. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:9 / 15
页数:7
相关论文
共 40 条
[1]   Novel 2-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,3,4-oxadiazole and 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole derivatives as dengue virus inhibitors targeting NS5 polymerase [J].
Benmansour, Fatiha ;
Eydoux, Cecilia ;
Querat, Gilles ;
de Lamballerie, Xavier ;
Canard, Bruno ;
Alvarez, Karine ;
Guillemot, Jean-Claude ;
Barral, Karine .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 109 :146-156
[2]   Chemical constituents of Anacolosa pervilleana and their antiviral activities [J].
Bourjot, Melanie ;
Leyssen, Pieter ;
Eydoux, Cecilia ;
Guillemot, Jean-Claude ;
Canard, Bruno ;
Rasoanaivo, Philippe ;
Gueritte, Francoise ;
Litaudon, Marc .
FITOTERAPIA, 2012, 83 (06) :1076-1080
[3]   Flacourtosides A-F, Phenolic Glycosides Isolated from Flacourtia ramontchi [J].
Bourjot, Melanie ;
Leyssen, Pieter ;
Eydoux, Cecilia ;
Guillemot, Jean-Claude ;
Canard, Bruno ;
Rasoanaivo, Philippe ;
Gueritte, Francoise ;
Litaudon, Marc .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (04) :752-758
[4]   SYNTHESIS OF (+)-8-METHYL CERCOSPORAMIDE - STEREOCHEMICAL CORRELATION OF NATURAL (-)-CERCOSPORAMIDE WITH (+)-USNIC ACID [J].
COOPER, AB ;
WANG, J ;
SAKSENA, AK ;
GIRIJAVALLABHAN, V ;
GANGULY, AK ;
CHAN, TM ;
MCPHAIL, AT .
TETRAHEDRON, 1992, 48 (23) :4757-4766
[5]  
Coulerie P, 2014, REC NAT PROD, V8, P286
[6]   Biflavonoids of Dacrydium balansae with Potent Inhibitory Activity on Dengue 2 NS5 Polymerase [J].
Coulerie, Paul ;
Eydoux, Cecilia ;
Hnawia, Edouard ;
Stuhl, Laetitia ;
Maciuk, Alexandre ;
Lebouvier, Nicolas ;
Canard, Bruno ;
Figadere, Bruno ;
Guillemot, Jean-Claude ;
Nour, Mohammed .
PLANTA MEDICA, 2012, 78 (07) :672-677
[7]   New Betulinic Acid Derivatives for Bevirimat-Resistant Human Immunodeficiency Virus Type-1 [J].
Dang, Zhao ;
Ho, Phong ;
Zhu, Lei ;
Qian, Keduo ;
Lee, Kuo-Hsiung ;
Huang, Li ;
Chen, Chin-Ho .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (05) :2029-2037
[8]   Evaluation of Antiplasmodial activity of extracts and constituents from Ampelozizyphus amazonicus [J].
do Carmo, Dominique F. M. ;
Amaral, Ana Claudia F. ;
Machado, Marta ;
Lopes, Dinora ;
Echevarria, Aurea ;
Rosario, Virgilio E. ;
Silva, Jefferson Rocha de A. .
PHARMACOGNOSY MAGAZINE, 2015, 11 (44) :S244-S250
[9]   A multi-locus plastid phylogenetic analysis of the pantropical genus Diospyros (Ebenaceae), with an emphasis on the radiation and biogeographic origins of the New Caledonian endemic species [J].
Duangjai, Sutee ;
Samuel, Rosabelle ;
Munzinger, Jerome ;
Forest, Felix ;
Wallnoefer, Bruno ;
Barfuss, Michael H. J. ;
Fischer, Gunter ;
Chase, Mark W. .
MOLECULAR PHYLOGENETICS AND EVOLUTION, 2009, 52 (03) :602-620
[10]   Efficacy and Long-Term Safety of a Dengue Vaccine in Regions of Endemic Disease [J].
Hadinegoro, S. R. ;
Arredondo-Garcia, J. L. ;
Capeding, M. R. ;
Deseda, C. ;
Chotpitayasunondh, T. ;
Dietze, R. ;
Ismail, H. I. Hj Muhammad ;
Reynales, H. ;
Limkittikul, K. ;
Rivera-Medina, D. M. ;
Tran, H. N. ;
Bouckenooghe, A. ;
Chansinghakul, D. ;
Cortes, M. ;
Fanouillere, K. ;
Forrat, R. ;
Frago, C. ;
Gailhardou, S. ;
Jackson, N. ;
Noriega, F. ;
Plennevaux, E. ;
Wartel, T. A. ;
Zambrano, B. ;
Saville, M. .
NEW ENGLAND JOURNAL OF MEDICINE, 2015, 373 (13) :1195-1206