Planta Med 2015; 81(17): 1604-1608
DOI: 10.1055/s-0035-1557773
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Isolation of Guttiferones from Renewable Parts of Symphonia globulifera by Centrifugal Partition Chromatography

Kevin Cottet
1   Laboratoire de Pharmacognosie, UMR CNRS 8638 COMETE (Chimie Organique, Médicinale, Extractive, Toxicologie et Environnement), Université Paris Descartes Sorbonne Paris Cité, Paris, France
,
Yann Fromentin
1   Laboratoire de Pharmacognosie, UMR CNRS 8638 COMETE (Chimie Organique, Médicinale, Extractive, Toxicologie et Environnement), Université Paris Descartes Sorbonne Paris Cité, Paris, France
,
Marina Kritsanida
1   Laboratoire de Pharmacognosie, UMR CNRS 8638 COMETE (Chimie Organique, Médicinale, Extractive, Toxicologie et Environnement), Université Paris Descartes Sorbonne Paris Cité, Paris, France
,
Raphaël Grougnet
1   Laboratoire de Pharmacognosie, UMR CNRS 8638 COMETE (Chimie Organique, Médicinale, Extractive, Toxicologie et Environnement), Université Paris Descartes Sorbonne Paris Cité, Paris, France
,
Guillaume Odonne
2   CNRS Guyane, USR 3456, Cayenne, France
,
Christophe Duplais
3   Laboratoire des Substances Naturelles Amazoniennes, Institut Pasteur de la Guyane, UMR EcoFoG (Ecologie des forêts de Guyane), Cayenne, France
,
Sylvie Michel
1   Laboratoire de Pharmacognosie, UMR CNRS 8638 COMETE (Chimie Organique, Médicinale, Extractive, Toxicologie et Environnement), Université Paris Descartes Sorbonne Paris Cité, Paris, France
,
Marie-Christine Lallemand
1   Laboratoire de Pharmacognosie, UMR CNRS 8638 COMETE (Chimie Organique, Médicinale, Extractive, Toxicologie et Environnement), Université Paris Descartes Sorbonne Paris Cité, Paris, France
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Publikationsverlauf

received 14. Oktober 2014
revised 28. April 2015

accepted 12. Juni 2015

Publikationsdatum:
21. September 2015 (online)

Abstract

The aim of this study was to investigate the species Symphonia globulifera, a source of polycyclic polyprenylated acyl phloroglucinols such as guttiferone A, which is known to exhibit a variety of biological activities including noticeable antileishmanial properties. Our goal was the identification and the quantification of guttiferone A in different renewable parts of S. globulifera and its preparative isolation. To the best of our knowledge, there is no data concerning its mechanism of action. Consequently, it is particularly interesting to isolate it in gram quantities in order to establish structure activity relationship studies. After performing high-performance liquid chromatography profiles detecting the presence of guttiferone A and proceeding to its quantification, a centrifugal partition chromatography methodology using a two-phase solvent system of cyclohexane/ethyl acetate/methanol/water (20 : 1 : 20 : 1, v/v/v/v) was applied to each extract. In conclusion, a centrifugal partition chromatography system has been developed to ensure a fast, reliable, and scalable way to isolate, with a high level of purity, guttiferone A from five renewable parts of S. globulifera. Moreover, this methodology can be extended to the isolation of other polycyclic polyprenylated acyl phloroglucinols such as guttiferones B, C, and D.

Supporting Information

 
  • References

  • 1 Marti G, Eparvier V, Moretti C, Prado S, Grellier P, Hue N, Thoison O, Delpech B, Guéritte F, Litaudon M. Antiplasmodial benzophenone derivatives from the root barks of Symphonia globulifera (Clusiaceae). Phytochemistry 2010; 71: 964-974
  • 2 Verotta L. Are acylphloroglucinols lead structures for the treatment of degenerative diseases?. Phytochem Rev 2002; 1: 389-407
  • 3 Ciochina R, Grossman RB. Polycyclic polyprenylated acylphloroglucinols. Chem Rev 2006; 106: 3963-3986
  • 4 Singh IP, Sidana J, Bharate SB, Foley W. Phloroglucinol compounds of natural origin: synthetic aspects. Nat Prod Rep 2010; 27: 393-416
  • 5 Njardarson JT. Synthetic efforts toward [3. 3.1] bridged bicyclic phloroglucinol natural products. Tetrahedron 2011; 67: 7631-7666
  • 6 Richard JA, Pouwer RH, Chen DYK. The chemistry of the polycyclic polyprenylated acylphloroglucinols (PPAPs). Angew Chem Int Ed 2012; 51: 4536-4561
  • 7 Croft SL, Sundar S, Fairlamb AH. Drug resistance in leishmaniasis. Clin Microbiol Rev 2006; 19: 111-126
  • 8 Polonio T, Efferth T. Leishmaniasis: drug resistance and natural products. Int J Mol Med 2008; 22: 277-286
  • 9 Lenta B, Vonthron-Sénécheau C, Weniger B, Devkota K, Ngoupayo J, Kaiser M, Naz Q, Choudhary M, Tsamo E, Sewald N. Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds from Allanblackia monticola and Symphonia globulifera . Molecules 2007; 12: 1548-1557
  • 10 Fromentin Y, Gaboriaud-Kolar N, Ndjakou Lenta B, Wansi JD, Buisson D, Mouray E, Grellier P, Loiseau PM, Lallemand MC, Michel S. Synthesis of novel guttiferone A derivatives: in-vitro evaluation toward Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani . Eur J Med Chem 2013; 65: 284-294
  • 11 Gustafson KR, Blunt JW, Munro MHG, Fuller RW, Mckee TC, Cardellina JH, Mcmahon JB, Cragg GM, Boyd MR. The guttiferone, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea . Tetrahedron 1992; 48: 10093-10102
  • 12 Ngouela S, Lenta BN, Noungoue DT, Diderot T, Ngoupavo J, Boyom F, Fekam F, Tsamo E, Gut J, Rosenthal PJ, Connolly JD. An antiproliferative xanthone of Symphonia pauciflora from the Madagascar rainforest. Phytochemistry 2006; 67: 302-306
  • 13 Kaur R, Chattopadhyay SK, Tandon S, Sharma S. Large scale extraction of the fruits of Garcinia indica for the isolation of new and known polyisoprenylated benzophenone derivatives. Ind Crops Prod 2012; 37: 420-426
  • 14 Ollivier A, Grougnet R, Cachet X, Meriane D, Ardisson J, Boutefnouchet S, Deguin B. Large scale purification of the SERCA inhibitor thapsigargin from Thapsia garganica L. roots using centrifugal partition chromatography. J Chromatogr B 2013; 926: 16-20
  • 15 Fromentin Y, Grellier P, Wansi JD, Lallemand MC, Buisson D. Yeast-Mediated xanthone synthesis through oxidative intramolecular cyclization. Org Lett 2012; 14: 5054-5057