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.
Key words
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
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
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
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
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
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
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
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