Subscribe to RSS
DOI: 10.1055/s-0029-1240619
© Georg Thieme Verlag KG Stuttgart · New York
Semi-Synthesis of Dihydrochalcone Derivatives and Their in Vitro Antimicrobial Activities
Publication History
received July 6, 2009
revised October 12, 2009
accepted October 22, 2009
Publication Date:
20 November 2009 (online)
Abstract
We describe the semi-synthesis of dihydrochalcone derivatives and their in vitro antimicrobial activities. These compounds were prepared by modifying two naturally occurring antimicrobial dihydrochalcones, erioschalcones A and B, reported by us earlier. The structures of the compounds were assigned on the basis of spectroscopic evidence and by comparing their physical and spectroscopic data with those reported in the literature. All the compounds were subjected to in vitro antimicrobial assays against a panel of pathogenic microorganisms, including gram-positive and gram-negative bacteria, and fungi. The antimicrobial efficacies of this class of compounds were established by correlating the activity profile of each compound with its structure and by comparing the activities of all the compounds with each other based on their structure. This should enable the development of other derivatives of the dihydrochalcone family that would serve as more potent antimicrobial agents against specific pathogens.
Key words
erioschalcone A - erioschalcone B - dihydrochalcones - antimicrobial - semi‐synthesis
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Awouafack M D, Kouam S F, Hussain H, Ngamga D, Tane P, Schulz B, Green I R, Khron K. Antimicrobial prenylated dihydrochalcones from Eriosema glomerata. Planta Med. 2008; 74 50-54
- 2 Hufford C D, Oguntimein B O. New dihydrochalcones and flavanones from Uvaria angolensis. J Nat Prod. 1982; 45 337-342
- 3 Choi J M, Yoon B S, Lee S K, Hwang J K, Ryang R. Antioxidant properties of neohesperidin dihydrochalcone: inhibition of hypochlorous acidinduced DNA strand breakage, protein degradation, and cell death. Biol Pharm Bull. 2007; 30 324-330
- 4 Portet B, Fabre N, Roumy V, Gornitzka H, Bourdy G, Chevalley S, Souvain M, Valentin A, Moulis C. Activity-guided isolation of antiplasmodial dihydrochalcones and flavanones from Piper hostmannianum var. berbicense. Phytochemistry. 2007; 68 1312-1320
- 5 Tadigoppula N, Tanvir K, Shweta N, Neena G, Suman G. A convenient and biogenetic type synthesis of few naturally occurring chromenodihydrochalcones and their in vitro antileishmanial activity. Bioorg Med Chem Lett. 2004; 14 3913-3916
- 6 Hufford C D, Oguntimein B O. Dihydrochalcones from Uvaria angolensis. Phytochemistry. 1980; 19 2036-2038
- 7 Ahluwalia V K, Nayal L, Kalia N, Bala S, Tehim A K. Synthesis and antimicrobial activity of substituted 3,4-dihydro-2H-1-benzopyrans. Ind J Chem. 1987; 26 B 384-386
- 8 Camele G, Monache F D, Monache G D, Bettolo G B M, De Lima R A. 2-Isoprenylemodin and 5,5′-dimethoxysesamin from Vismia guaramirangae. Phytochemistry. 1982; 21 417-419
- 9 Yamauchi K, Tanabe T, Kinoshita M. Trimethylsulfonium hydroxide: a new methylating agent. J Org Chem. 1979; 44 638-639
- 10 Khron K, Steingröver K, Rao M S. Isolation and synthesis of chalcones with different degrees of saturation. Phytochemistry. 2002; 61 931-936
- 11 Rao M S, Kotesh J, Narukulla R, Duddeck H. Synthesis and spectroscopic characterization of some chromanochalcones and their dihydro derivatives. Arkivoc. 2004; XIV 96-102
- 12 Nickl J. Synthese von β-Tubasäure und von Lonchocarpin. Chem Ber. 1958; 91 1372-1376
- 13 Kusari S, Lamshöft M, Spiteller M. Aspergillus fumigatus Fresenius, an endophytic fungus from Juniperus communis L. Horstmann as a novel source of the anticancer pro-drug deoxypodophyllotoxin. J Appl Microbiol. 2009; 107 1019-1030
- 14 Wikler M A. Performance standards for antimicrobial disk susceptibility tests; approved standard, ninth edition (M2-A9). Wayne; CLSI (Clinical and Laboratory Standards Institute) 2006
Prof. Dr. Dr. h.c. Michael Spiteller
Institut für Umweltforschung (INFU)
Technische Universität Dortmund
Otto-Hahn-Strasse 6
44221 Dortmund
Germany
Phone: + 49 23 17 55 40 80
Fax: + 49 23 17 55 40 85
Email: m.spiteller@infu.uni-dortmund.de
- www.thieme-connect.de/ejournals/toc/plantamedica