Antibacterial Constituents from the Roots of Erythrina herbacea against Methicillin-resistant Staphylococcus aureus

Abstract

Two new compounds, erybacin A (1) and erybacin B (2), together with 10 known compounds (3–12), were isolated from the roots of Erythrina herbacea. Their structures were established on the basis of spectroscopic analyses. Erybacin A is a rare, naturally occurring 1-hydroxy-1,3-diphenylpropan-2-one derivative. The isolated compounds were evaluated for their antibacterial activity against 13 strains of methicillin-resistant Staphylococcus aureus (MRSA). The new compound 2 showed a potent bactericidal activity against MRSA.

Erythrina herbacea - Leguminosae - erybacin A - erybacin B - anti‐MRSA activity

References

• 1 Tanaka H, Hattori H, Oh-Uchi T, Sato M, Yamaguchi R, Sako M, Tateishi Y. Two new isoflavanones from Erythrina costaricensis.  J Asian Nat Prod Res. 2008;  10 983-987
• 2 Tanaka H, Hattori H, Oh-Uchi T, Sato M, Sako M, Tateishi Y, Ghazala H R. Three new isoflavanones from Erythrina costaricensis.  Nat Prod Res. 2009;  23 1089-1094
• 3 Tanaka H, Hattori H, Tanaka T, Sakai E, Tanaka N, Kulkarni A, Etoh H. A new Erythrina alkaloid from Erythrina herbacea.  J Nat Med. 2008;  62 228-231
• 4 Hanssen H P, Abraham W R. Volatiles from liquid cultures of Lentinellus cochleatus (Basidiomycotina).  Z Naturforsch. 1986;  41c 959-962
• 5 Leverett R S, Noreen M, Russell J M. Synthesis and structure-phytotoxicity relationships of acetylenic phenols and chromene metabolites, and their analogues, from the grapevine pathogen Eutypa lata.  J Nat Prod. 2003;  66 169-176
• 6 Telikepalli H, Gollapudi S R, Keshavarz-Shokri A, Velazquez L, Sandmann R A, Veliz E A, Rao K V J, Madhavi A S, Mitscher L A. Isoflavonoids and a cinnamyl phenol from root extracts of Erythrina variegata.  Phytochemistry. 1990;  29 2005-2007
• 7 Zeng L, Fukai T, Nomura T, Zhang R Y, Lou Z C. Five new isoprenoid-substituted favonoids, glyasperins F, G, H, I, and J from the roots of Glycyrrhiza aspera.  Heterocycles. 1992;  34 1813-1828
• 8 Tanaka H, Hirata M, Etoh H, Sako M, Sato M, Murata J, Murata H, Darnaedi D, Fukai T. Four new isoflavonoids and a new 2-arylbenzofuran from the roots of Erythrina variegata.  Heterocycles. 2003;  60 2767-2773
• 9 Iinuma M, Okawa Y, Tanaka T, Kobayashi Y, Miyauchi K. Phenolic compounds in Erythrina x bidwillii and their activity against oral microbial organisms.  Heterocycles. 1994;  39 687-692
• 10 Tanaka H, Tanaka T, Hosoya A, Kitade Y, Etoh H. An isoflavan from Erythrina x bidwillii.  Phytochemistry. 1998;  47 1397-1400
• 11 Biggs D R, Fielder S. Synthesis and properties of phaseollidin isoflavan.  J Nat Prod. 1994;  57 663-664
• 12 Nomura T, Fukai T. Phenolic constituents of licorice (Glycyrrhiza species). Progress in the chemistry of organic natural products, Vol. 73. Vienna; Springer 1998: 1-140
• 13 Kinoshita T, Kajiyama K, Hiraga Y, Takahashi K, Tamura Y, Mizutani K. The isolation of new pyrano-2-arylbenzofuran derivatives from the root of Glycyrrhiza glabra.  Chem Pharm Bull. 1996;  44 1218-1221
• 14 Fukai T, Sheng C B, Horikoshi T, Nomura T. Isoprenylated flavonoids from underground parts of Glycyrrhiza glabra.  Phytochemistry. 1996;  43 1119-1124
• 15 Katritzky A R, Oniciu D C, Ghiviriga I, Soti F. Syntheses of dialkyl and functionalized ketones via 1-(benzotriazol-1-yl)alkyl methyl thioethers.  J Org Chem. 1998;  63 2110-2115
• 16 Sanchez-Gonzalez M, Rosazza J P N. Mixed aromatic acyloin condensations with recombinant benzaldehyde lyase: synthesis of α-hydroxydihydrochalcones and related α-hydroxy ketones.  Adv Synth Catal. 2003;  345 819-824
• 17 Markham K R, Chari V M, Mabry T J. Carbon-13 NMR spectroscopy of flavonoids. Harborne JB, Mabry TJ The flavonoids: advances in research. New York; Chapman & Hall 1982: 19-134
• 18 Kiuchi F, Chen X, Tsuda Y. Four new phenolic constituents from licorice (root of Glycyrrhiza sp.).  Heterocycles. 1990;  31 629-636
• 19 Magalhaes A F, Tozzi A M G A, Magalhaes E G, Souza Moraes V R. Prenylated flavonoids from Deguelia hatschbachii and their systematic significance in Deguelia.  Phytochemistry. 2001;  57 77-89
• 20 Fukai T, Nomura T. Isoprenoid-substituted flavonoids from roots of Glycyrrhiza inflata.  Phytochemistry. 1995;  38 759-765
• 21 Na M, Hoang D M, Njamen D, Mbafor J T, Fomum Z T, Thuong P T, Ahn J S, Keun W. Inhibitory effect of 2-arylbenzofurans from Erythrina addisoniae on protein tyrosine phosphatase-1B.  Bioorg Med Chem Lett. 2007;  17 3868-3871