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Planta Med 2016; 82(11/12): 1087-1095
DOI: 10.1055/s-0042-108741
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

New Polyfunctional Phragmalin Limonoids from Neobeguea mahafalensis [*]

Torgils Fossen
1   Department of Chemistry, University of Bergen, Bergen, Norway
,
Aleh Yahorau
2   Department of Pharmaceutical Biosciences, Uppsala University, Uppsala, Sweden
,
Sviatlana Yahorava
2   Department of Pharmaceutical Biosciences, Uppsala University, Uppsala, Sweden
,
Fanja Raharinjato
3   Institut Malagasy de Recherches Appliquées, Fondation Rakoto Ratsimamanga, Antananarivo, Madagascar
,
Solofoniaina Razafimahefa
3   Institut Malagasy de Recherches Appliquées, Fondation Rakoto Ratsimamanga, Antananarivo, Madagascar
,
Philippe Rasoanaivo
3   Institut Malagasy de Recherches Appliquées, Fondation Rakoto Ratsimamanga, Antananarivo, Madagascar
,
Jarl E. S. Wikberg
2   Department of Pharmaceutical Biosciences, Uppsala University, Uppsala, Sweden
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Publikationsverlauf

received 08. März 2016
revised 05. Mai 2016

accepted 09. Mai 2016

Publikationsdatum:
24. Juni 2016 (online)

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Abstract

Neobeguea mahafalensis is used as a medicinal plant in Madagascar. A decoction of the stem bark of this species is reported to treat back pain. Recently, it was reported that a decoction of the root bark, containing two novel phragmalin limonoids as identified active constituents, exhibited an extraordinarily high potency and remarkably long duration in augmenting sexual activity in male rodents.

From the dichloromethane extract of the root barks of N. mahafalensis, nine phragmalin limonoids were isolated, of which eight were novel compounds. The structures were established mainly by extensive use of 2D NMR spectroscopic techniques and high-resolution mass spectrometry. One of the new compounds named dodoguin displayed sleep-inducing activity in Swiss albino mice. The amount of 3–10 mg/kg of this compound induced sleep 18–22 min after its administration with a duration of 16–18 min.

Key words

Neobeguea mahafalensis - Meliaceae - phragmalin limonoids - structure elucidation - 2D NMR - sleep-inducing activity

* Dedicated to Professor Kurt Hostettmann in recognition of his outstanding contribution to natural product research.


Supporting Information

 

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