Antimicrobial Prenylated Dihydrochalcones from Eriosema glomerata

Abstract

Two new natural dihydrochalcones exhibiting antimicrobial properties together with six known compounds were isolated from the Cameroonian medicinal plant Eriosema glomerata. The structures of the new dihydrochalcones were elucidated as 2′,4′-dihydroxy-4-methoxy-3′-(γ,γ-dimethylallyl)dihydrochalcone and 2′,4′-dihydroxy-3′-(γ,γ-dimethylallyl)dihydrochalcone by detailed spectroscopic analysis. The two new dihydrochalcones, named erioschalcones A (1) and B (2), demonstrated significant inhibitory activity against the microbial strains Bacillus megaterium, Escherichia coli, Chlorella fusca and Microbotryum violaceum.

Eriosema glomerata - Fabaceae - dihydrochalcone - antimicrobial - erioschalcone A - erioschalcone B

References

• 1 Ma W G, Fuzzati N, Li Q S, Yang C R, Stoeckli-Evans H, Hostettmann K. Polyphenols from Eriosema tuberosum. .  Phytochemistry. 1995;  39 1049-61
• 2 Ojewole J AO, Drewes S E, Khan F. Vasodilatory and hypoglycaemic effects of two pyrano-isoflavone extractives from Eriosema kraussianum N. E. Br. [Fabaceae] rootstock in experimental rat models.  Phytochemistry. 2006;  67 610-7
• 3 Drewes S E, Horn M M, Khan F, Munro O Q, Dhlamini J TB, Rakuambo C. et al . Pyro-isoflavones with erectile-dysfunction activity from Eriosema kraussianum.  Phytochemistry. 2002;  59 739-47
• 4 Drewes E S, Horn M M, Khan F, Munro O Q, Jabu T B, Rakuambo D C. et al . Minor pyrano-isoflavones from Eriosema kraussianum: activity-structure, and chemical reaction studies.  Phytochemistry. 2004;  65 1955-61
• 5 Ma W G, Fuzzati N, Xue Y, Yang C R, Hostettmann K. Four chromones from Eriosema tuberosum.  Phytochemistry. 1996;  41 1287-91
• 6 Höller U, Wright A D, Matthée G F, König G M, Draeger S, Aust H -J. et al . Fungi from marine sponges: Diversity biological activity and secondary metabolites.  Mycol Res. 2000;  104 1354-65
• 7 Matsuura S, Yoshioka S, Iinuma M. Studies on the constituents of the useful plants. II. The constituents of the leaves of Cassia obtusifolia L.  Yakugaku Zasshi. 1978;  98 1288-91
• 8 Qi S -H, Wu D -G, Zhang S, Luo X -D. Constituents of Carapa guianensis Aubl. (Meliaceae).  Pharmazie. 2004;  59 488-90
• 9 Meyer A, Jeger O, Ruzicka L. Mitteilung.  Zur Konstitution der Sojasapogenole D und B Helv Chim Acta. 1950;  33 687-99
• 10 Semmar N, Jay M, Chemli R. Chemical diversification trends in Astragalus caprinus (Leguminosae), based on the flavonoid pathway.  Biochem Syst Ecol. 2001;  29 727-38
• 11 Mizuno M, Tanaka T, Katsuragawa M, Saito H, Iinuma M. A new pterocarpan from the heartwood of Cladrastis platycarpa.  J Nat Prod. 1990;  53 498-9
• 12 Tazoo D, Krohn K, Hussain H, Kouam S F, Dongo E. Laportoside A and laportomide A: a new cerebroside and a new ceramide from leaves of Laportea ovalifolia.  Z Naturforsch. 2007;  62b 1208-12
• 13 Shiao Y J, Wang C -N, Wang W -Y, Lin Y -L. Neuroprotective flavonoids from Flemingia macrophylla. .  Planta Med. 2005;  71 835-40
• 14 Portet B, Fabre N, Roumy V, Gornitzka H, Bourdy G, Chevalley S. et al . Activity-guided isolation of antiplasmodial dihydrochalcones and flavanones from Piper hostmannianum var. berbicense.  Phytochemistry. 2007;  68 1312-20
• 15 Hufford C D, Oguntimein B O. New dihydrochalcones and flavanones from Uvaria angolensis.  J Nat Prod. 1982;  45 337-42
• 16 Logendra S, Ribnicky D M, Yang H, Poulev A, Ma J, Kennelly E J. et al . Bioassay-guided isolation of aldose reductase inhibitors from Artemisia dracunculus.  Phytochemistry. 2006;  67 1539-46
• 17 Krasnov E A, Ermilova E V, Kadyrova T V, Raldugin V A, Bagryanskaya I Y, Gatilov Y V. et al . Phenolic components of Empetrum nigrum extract and the crystal structure of one of them.  Chem Nat Comp. 2000;  36 493-6
• 18 Adityachaudhury N, Chowdhury A, Kirtaniya C, Chatterjee A. Synthesis of tetrahydroflemichapparin A. London; Chemistry & Industry 1975: 179-80
• 19 Nkengfack A E, Van Heerden F R, Fuendjiep V, Fomum Z T. Asebotin, a dihydrochalcone glucoside from Guibourtia tessmannii.  Fitoterapia. 2001;  72 834-6
• 20 Fuendjiep V, Wandji J, Tillequin F, Mulholland D A, Budzikiewicz H, Fomum Z T. et al . Chalconoid and stilbenoid glycosides from Guibourtia tessmanii.  Phytochemistry. 2002;  60 803-6
• 21 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 3913-6
• 22 Choi J -M, Yoon B -S, Lee S -K, Hwang J -K, Ryang R. Antioxidant properties of neohesperidin dihydrochalcone: inhibition of hypochlorous acid-induced DNA strand breakage, protein degradation, and cell death.  Biol Pharm Bull. 2007;  30 324-30
• 23 Chen J -J, Lee H -H, Duh C -Y, Chen I -S. Cytotoxic chalcones and flavonoids from the leaves of Muntingia calabura.  Planta Med. 2005;  71 970-3
• 24 Orjala J, Wright A D, Behrends H, Folkers G, Sticher O, Rüegger H. et al . Cytotoxic and antibacterial dihydrochalcones from Piper aduncum.  J Nat Prod. 1994;  57 18-26
• 25 Waffo A K., Azebaze G A, Nkengfack A E, Fomum Z T, Meyer M, Bodo B. et al . Indicanines B and C, two isoflavonoid derivatives from the root bark of Erythrina indica.  Phytochemistry. 2000;  53 981-5
• 26 Erasto P, Bojase-Moleta G, Majinda R RT. Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus.  Phytochemistry. 2004;  65 875-80
• 27 Matern U, Oberer L, Erhard M, Herdman M, Weckesser J. Hofmannolin, a cyanopeptolin from Scytonema hofmanni PCC 7110.  Phytochemistry. 2003;  64 1061-7