Planta Med 2009; 75(11): 1258-1261
DOI: 10.1055/s-0029-1185545
Natural Product Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Antimicrobial Dihydroisocoumarins from Crassocephalum biafrae

Turibio K. Tabopda1 , Gislain W. Fotso1 , Joseph Ngoupayo1 , Anne-Claire Mitaine-Offer2 , Bonaventure T. Ngadjui1 , Marie-Aleth Lacaille-Dubois2
  • 1Département de Chimie Organique, Université de Yaoundé I, Yaoundé, Cameroon
  • 2Université de Bourgogne, Faculté de Pharmacie, Laboratoire de Pharmacognosie, Dijon cedex, France
Further Information

Publication History

received November 24, 2008 revised February 18, 2009

accepted February 28, 2009

Publication Date:
06 April 2009 (online)

Abstract

Bioassay-guided fractionation of the CHCl3-soluble extract of the stem bark of Crassocephalum biafrae (Asteraceae) resulted in the isolation of three new dihydroisocoumarins, named biafraecoumarins A (1), B (2), and C (3); two known triterpenes (4 and 5); and a known ceramide (6). The structures of the new compounds were established as 7-but-15-enyl-6,8-dihydroxy-3(R)-penta-9,11-dienylisochroman-1-one (1), 7-butyl-6,8-dihydroxy-3(R)-penta-9,11-dienylisochroman-1-one (2), and 7-butyl-6,8-dihydroxy-3(R)-pent-10-enylisochroman-1-one (3) using spectroscopic data. Compounds 13 exhibit low to significant antimicrobial activities against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Pseudomonas picketti, Trichphyton longifusus, Aspergillus flavus, Microsporum canis, Fusarium solani, Candida albicans, and Candida glabrata.

References

  • 1 Adebooye O C. Solanecio biafrae (Olive and Heirne), C Jeffery. Grubben GJH, Denton OA Plant resources of tropical Africa 2: Vegetables. Leiden, Netherlands; PROTA Foundation 2004: 469-471
  • 2 Adjanohoun J E, Aboubakar N, Dramane K, Ebot M E, Ekpere J A, Enow-Orock E G, Focho D, Gbile Z O, Kamanyi A, Kamsu K J, Keita A, Mbenkum T, Mbi C N, Mbiele A L, Mbome I L, Mubiru N K, Nancy W L, Nkongmeneck B, Satabie B, Sofowora A, Tamze V, Wirmum C K. Traditional medicine and pharmacopoeia: contribution to ethnobotanical and floristic studies in Cameroon. Porto-Novo; Organisation of African Unity Scientific, Technical and Research Commission. Centre National de Production de Manuels Scolaires 1996: 85
  • 3 Zollo P HA, Kuiate J R, Menut C, Bessiere J M. Aromatic plants of tropical central Africa. XXXVI. Chemical composition of essential oils from seven Cameroonian Crassocephalum species.  J Essent Oil Res. 2000;  12 533-536
  • 4 Asada Y, Shiraishi M, Takeuchi T, Osawa Y, Furuya T. Pyrrolizidine alkaloids from Crassocephalum crepidioides.  Planta Med. 1985;  51 539-540
  • 5 Kongsaeree P, Prabpai S, Sriubolmas N, Vongvein C, Wiyakrutta S. Antimalarial dihydroisocoumarins produced by Geotrichum sp., an endophytic fungus of Crassocephalum crepidioides.  J Nat Prod. 2003;  66 709-711
  • 6 Mohamed-Elamir F H, Shinji O, Fathy F A, Hazem A A, Emi O, Paul W P, Toshifumi H. Cyclooxygenase (COX)-1 and -2 inhibitory labdane diterpenes from Crassocephalum mannii.  J Nat Prod. 2008;  71 1070-1073
  • 7 Mohamed-Elamir F H, Ashraf A A, Ahmed A A, Djemgou C P, Tane P, Mehawed M A. A new 14,15-dinorlabdane glucoside from Crassocephalum mannii.  Nat Prod Commun. 2008;  3 869-872
  • 8 Albrecht P, Ourisson G. Triterpene alcohol isolation from oil shale.  Science. 1969;  163 1192-1193
  • 9 Jain R, Nagpal S. Chemical constituents of the roots of Kirganelia reticulate.  J Indian Chem Soc. 2002;  79 776-777
  • 10 Mendelsohn R, Rerek M E, Moore D J. Infrared spectroscopy and microscopic imaging of stratum corneum models and skin.  Phys Chem Chem Phys. 2000;  2 4651-4657
  • 11 Barry J, Kagan H B, Snatzke G. Synthèse de methyl-tetralones-1 et de methyl-tetralines optiquement actives: etude de leurs conformations par dichroïsme circulaire.  Tetrahedron. 1971;  27 4737-4748
  • 12 Dornhege E, Snatzke G. Circulardichroismus XL: Chiroptische Eigenschaften von Aminoindanolen und verwandten Verbindungen.  Tetrahedron. 1970;  26 3059-3067
  • 13 Krohn K, Bahramsari R, Florke U, Ludewig K, Kliche-Spory C, Michel A, Aust H J, Draeger S, Schulz B, Antus S. Dihydroisocoumarins from fungi: isolation, structure elucidation, circular dichroism and biological activity.  Phytochemistry. 1997;  45 313-320
  • 14 Paraschos S, Magiatis P, Kalpoutzakis E, Harvala C, Skaltsounis A L. Three new dihydroisocoumarins from the Greek endemic species Scorzonera cretica.  J Nat Prod. 2001;  64 1585-1587
  • 15 Atta-ur-Rahman, Choudhary M I, Thomsen W J. Bioassay techniques for drug development. Amsterdam, The Netherlands; Harwood Academic Publishers 2001: 16-22
  • 16 McLauglin J L, Chang C J, Smith D L. “Bench top” bioassay for the discovery of bioactive natural products: an update. Atta-ur-Rahman Studies in natural products chemistry, Vol. 9. Amsterdam, The Netherlands; Elsevier Science 1991: 383-409
  • 17 Tabopda K T, Ngoupayo J, Liu J W, Mitaine-Offer A C, Tanoli S AK, Khan S N, Ali M S, Ngadjui B T, Tsamo E, Lacaille-Dubois M A, Luu B. Bioactive aristolactams from Piper umbellatum.  Phytochemistry. 2008;  69 1726-1731
  • 18 Tabopda K T, Ngoupayo J, Tanoli S AK, Mitaine-Offer A C, Ngadjui B T, Ali M S, Luu B, Lacaille-Dubois M A. Antimicrobial pentacyclic triterpenoids from Terminalia superba.  Planta Med. DOI: 10.1055/s-0029-1185328

Dr. Turibio Kuiate Tabopda

Département de Chimie Organique
Université de Yaoundé I

BP 812 Yaoundé

Cameroun

Phone: + 2 37 77 97 66 33

Fax: + 2 37 22 22 18 73

Email: ttabopda@yahoo.fr