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Planta Med 2010; 76(2): 165-171
DOI: 10.1055/s-0029-1186038
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Turrealabdane, Turreanone and an Antisalmonellal Agent from Turraeanthus africanus

Pierre C. Djemgou1 , Donatien Gatsing2 , Mohamed-Elamir F. Hegazy3 , Abou H. El-Hamd Mohamed4 , François Ngandeu1 , Pierre Tane1 , Bonaventure T. Ngadjui5 , Serge Fotso6 , Hartmut Laatsch6
  • 1Department of Chemistry, University of Dschang, Dschang, Cameroon
  • 2Department of Biochemistry, University of Dschang, Dschang, Cameroon
  • 3Chemistry of Medicinal Plants Department, National Research Centre, Dokki, Giza, Egypt
  • 4Department of Chemistry, Aswan-Faculty of Science, South Valley University, Aswan, Egypt
  • 5Department of Organic Chemistry, University of Yaoundé I, Yaoundé, Cameroon
  • 6Institute of Organic and Biomolecular Chemistry, University of Göttingen, Göttingen, Germany
Further Information

Publication History

received March 4, 2009 revised July 2, 2009

accepted July 9, 2009

Publication Date:
17 August 2009 (online)

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Abstract

Phytochemical investigation of the seeds of Turraeanthus africanus (Meliaceae), a Cameroonian plant species traditionally used in the treatment of typhoid fever, afforded eight compounds, including two labdanes, a C-arabinoside derivative, a sesquiterpene, and several triterpenes, two of which are new: 15′,16′-dihydroxy-15(12′),15′(16′)-diolidebislabd-8(17),8′(17′),12-trien-16-al (1), trivially named turrealabdane and a C-arabinoside derivative (2), trivially named turreanone. The other compounds are 12,15-epoxylabda-8(17),12,14-trien-16-acetate (3), (+)-eudesmanol-O-L-arabinoside, cyclolaudenol, stigmasterol, sitosterol glucoside and lupeol. Acetylation and oxidation of turrealabdane yielded 15′,16′-diacetoxyturrealabdane and 15,12′-dioxoturrealabdane-15′,16′-dial, respectively. Their structures were determined by means of spectroscopic data including 1D and 2D NMR in combination with MS. The compounds were evaluated for antibacterial activities, chloramphenicol and amoxicillin being used as standard. Compound 3 was the only active principle, possessing the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of respectively 25 µg/mL and 100 µg/mL against Salmonella typhi, S. paratyphi A and S. paratyphi B. This compound did not show any activity against Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae and Staphylococcus aureus.

Key words

Turraeanthus africanus - Meliaceae - labdane - turreanone - antibacterial activities

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Mohamed-Elamir F. Hegazy

Chemistry of Medicinal Plant Department
National Research Centre

El-Bohoth St.

12622 Dokki Giza

Egypt

Phone: + 20 1 20 07 35 57

Fax: + 20 2 33 37 09 31

Email: elamir77@yahoo.com

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