Goniomedines A and B: Unprecedented Bisindole Alkaloids Formed through Fusion of Two Indole Moieties via a Dihydropyran Unit

被引:41
作者
Beniddir, Mehdi A. [1 ]
Martin, Marie-Therese [1 ]
Dau, Marie-Elise Tran Huu [1 ]
Grellier, Philippe [2 ]
Rasoanaivo, Philippe [3 ]
Gueritte, Francoise [1 ]
Litaudon, Marc [1 ]
机构
[1] CNRS, Lab Ex LERMIT, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France
[2] CNRS, Team APE, UMR 7245, Museum Natl Hist Nat, F-75231 Paris, France
[3] Inst Malgache Rech Appl, Antananarivo 102, Madagascar
关键词
D O I
10.1021/ol301832t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two novel bisindole alkaloids, goniomedines A (1) and B (2), possessing an unprecedented quebrachamine-pleioarpamine-type skeleton, in which indole moieties are fused via a dihydropyran unit, were isolated from the stem bark of Gonioma malagasy. The structures were elucidated by comprehensive analysis of MS and NMR spectroscopic data. Their absolute configurations were deduced following the comparison of experimental and theoretically calculated ECD spectra and through biogenetic considerations. Goniomedine B (2) exhibited moderate activity against Plasmodium falciparum.
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收藏
页码:4162 / 4165
页数:4
相关论文
共 15 条
[1]   LEAF ALKALOIDS OF RAUWOLFIA-VOLKENSII [J].
AKINLOYE, BA ;
COURT, WE .
PHYTOCHEMISTRY, 1980, 19 (02) :307-311
[2]   Enantioselective synthesis of 3,3-disubstituted piperidine derivatives by enolate dialkylation of phenylglycinol-derived oxazolopiperidone lactams [J].
Amat, Mercedes ;
Lozano, Oscar ;
Escolano, Carmen ;
Molins, Elies ;
Bosch, Joan .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12) :4431-4439
[3]   Diarylheptanoid Glucosides from Pyrostria major and Their Antiprotozoal Activities [J].
Beniddir, Mehdi A. ;
Grellier, Philippe ;
Rasoanaivo, Philippe ;
Loiseau, Philippe M. ;
Bories, Christian ;
Dumontet, Vincent ;
Gueritte, Francoise ;
Litaudon, Marc .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (05) :1039-1046
[4]   STRUCTURE OF GONIOMINE, AN ALKALOID OF A NEW TYPE BIOGENETICALLY RELATED TO INDOLE ALKALOID - X-RAY-ANALYSIS OF DIHYDROGONIOMINE [J].
CHIARONI, A ;
RANDRIAMBOLA, L ;
RICHE, C ;
HUSSON, HP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5920-5921
[5]  
Das B.C., 1974, TETRAHEDRON LETT, V15, P4299
[6]  
Dewick P. M., 2009, MED NATURAL PRODUCTS, P163
[7]   Synthesis of vinca alakaloids and related compounds 98.: Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system.: A simple synthesis of (7S,20S)-(+)-rhazidigenine and (2R,7S,20S)-(+)-rhazidine [J].
Éles, J ;
Kalaus, G ;
Lévai, A ;
Greiner, I ;
Kajtár-Peredy, M ;
Szabó, P ;
Szabó, L ;
Szántay, C .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (04) :767-771
[8]   CONSTITUTION OF 2 NEW DIMERIC INDOLE ALKALOIDS PYCNANTHIN AND ALKALOIDS PLEIOMUTININ .132. [J].
GORMAN, AA ;
DASTOOR, NJ ;
HESSE, M ;
VONPHILI.W ;
RENNER, U ;
SCHMID, H .
HELVETICA CHIMICA ACTA, 1969, 52 (01) :33-+
[9]   Bipleiophylline, an unprecedented cytotoxic bisindole alkaloid constituted from the bridging of two indole moieties by an aromatic spacer unit [J].
Kam, Toh-Seok ;
Tan, Shin-Jowl ;
Ng, Seik-Weng ;
Komiyama, Kanki .
ORGANIC LETTERS, 2008, 10 (17) :3749-3752
[10]   ANWENDUNGEN DER MASSENSPEKTROMETRIE ZUR STRUKTURAUFKLARUNG VON ALKALOIDEN .7. NEUE ALKALOIDE AUS GONIOMA KAMASSI E MEY [J].
KASCHNITZ, R ;
SPITELLER, G .
MONATSHEFTE FUR CHEMIE UND VERWANDTE TEILE ANDERER WISSENSCHAFTEN, 1965, 96 (03) :909-+