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Leu T.* 1 , Soulet S. 1 , Herbette G. 2 , Faure R. 2 , Bianchini J.-P. 1 , Meijer L. 3 and Raharivelomanana P 1 . *E-mail to: [email protected] PowerPoint PPT Presentation


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Elastase inhibitors and cancer preventive potential agents from Calophyllum inophyllum (L.) grown in French Polynesia. Fig 1: Separation of resins from Tamanu oil. Calophyllolide. Inophyllum C. Inophyllum E. Inophyllum D. Inophyllum P. Calanolide « No name ». Calanolide A.

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Leu T.* 1 , Soulet S. 1 , Herbette G. 2 , Faure R. 2 , Bianchini J.-P. 1 , Meijer L. 3 and Raharivelomanana P 1 . *E-mail to: [email protected]

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Elastase inhibitors and cancer preventive potential agents from Calophyllum inophyllum (L.) grown in French Polynesia

Fig 1: Separation of resins from Tamanu oil

Calophyllolide

Inophyllum C

Inophyllum E

Inophyllum D

Inophyllum P

Calanolide « No name »

Calanolide A

12-oxocalanolide A

Calanolide B

Epicalanolide C

Calanolide D

Inocalophyllin A

Inocalophyllin B

Tamanolide

Tamanolide D

Tamanolide P

GA 2009

Leu T.*1, Soulet S.1, Herbette G.2, Faure R.2, Bianchini J.-P.1, Meijer L.3 and Raharivelomanana P1.

*E-mail to: [email protected]

1 Laboratoire Biotem EA 4239, Université de la Polynésie Française, BP 6570, 98702 Faa’a, Tahiti, French Polynesia

2 Spectropole de Marseille, Université Paul Cézanne, 13397 Marseille Cedex 20, France

3 Station Biologique de Roscoff, CNRS/USR 3151, Place G. Tessier, BP 74, 29682, Roscoff, Cedex, France

Introduction:

 Elastase.

 Calophyllum inophyllum, L.

  • Division: Magnoliophyta

     Class: Magnoliopsida

     Order: Theales

     Family: Clusiaceae

    Genus: Calophyllum

    Species: C. inophyllum

Tamanu (C. inophyllum) is a pantropical species widely used in Polynesian folk medicine for skin treatments, wound healing and as pain killer3.

Previous studies have shown the presence of bioactive coumarin derivatives4.

Elastase is a serin endo-proteinase responsible for extracellular matrix proteins degradation.

Overexpression was linked to COPD, Cystic Fibrosis1 and associated to increased low-molecular weight form Cyclin E correlating with poor diagnosis and morbidity increase in breast cancer2.

Enzymatic screening assay revealed elastase inhibiting properties of fractions of Tamanu oil. Bioguided phytochemical investigations led to the identification of elastase inhibiting new pyranocoumarin compounds.

  • Experimental.

  • Resin of Tamanu was extracted from seed oil with 96° EtOH and neutral fraction was separated from the acidic one (fig. 1).

  • Products of NRT and ART were isolated by chromatographic methods and identified by spectroscopic analyses (UV, IR, HRMS, 1D and 2D NMR).

  • In vitro enzymatic inhibition assay was carried out at different steps of purification.

  • Bioguided fractionation led to the isolation of new elastase inhibitory compounds.

Coumarin derivatives identified in Tamanu oil.

Elastase inhibiting activity.

Inophyllum serie

Calanolide serie

Calophyllolide is the most active compound (IC50 = 8.4 µM)

Structure-activity relationship.

Inocalophyllin serie

Tamanolide serie

Phenyl C-4 substituent, methoxyl C-8b and tigloyl C-12a groups appears to be structural requirements for elastase inhibition by coumarin derivatives

Tamanolide is a new serie of coumarin derivatives

Conclusions.

 16 coumarin derivatives were identified from the resin of Tamanu including the new tamanolides and the firstly occuring in C. inophyllum calanolides.

 Among those, 5 compounds led to significant inhibition of elastase, the most active compound being calophyllolide.

 Phenyl C-4 susbtituent and opened D-ring are structural requirements for elastase inhibition by coumarin derivatives.

  • References:

  • Barnes, P.J., Hansel, T.T. (2004) The Lancet 364: 985-996.

  • Akli, S., Keyomarsi, K. (2004) Br Cancer Res 6: 188-191.

  • Pétard, P. (1986) Plantes utiles de Polynésie – Raau Tahiti, Editions Haere Po No Tahiti, Papeete, Tahiti.

  • Laure, F. et al. (2008) Anal Chim Act 624: 147-153.

Acknowledgement:

The Ministère chargé de la Recherche en Polynésie française is greatly acknowledge for financial support (Convention n°5.0314/PR du 30/11/05, avenant n°6.0360/PR du 24/08/06). The authors are also grateful to Dr. J.-Y. Meyer and Dr. P. Frogier for helpful commentaries.


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