New Antibacterial Germacrene from Verbesina negrensis

Abstract

Several health benefits have been attributed to members of the Verbesina genus, including promotion of urinary and gastrointestinal health. Verbesina species are also reported to exhibit antibacterial, antiparasitic, and antioxidant activities. Although members of the Verbesina genus produce various pharmacologically relevant chemicals as secondary metabolites, including eudesmanes, flavonoids, guanidine alkaloids, acetylenic compounds, and germacrenes, the active compounds required for these benefits remain unknown. To investigate potential antimicrobial activities of Verbesina negrensis, crude extracts from plant aerial structures were evaluated. Following chemical fractionation, the chloroformic extract from Verbesina negrensis was subjected to bioassay-guided isolation using disk diffusion assays to determine antimicrobial activity. The active compound was characterized as 6β-cinnamoyloxy-1β-hydroxy-10α-metoxy-3-oxo-germacra-4,5Z-ene (1). Fractions containing 1 inhibited both Enterococcus faecalis (ATCC 29 212) and Staphylococcus aureus (ATCC 29213). The MIC for 1 was determined by microbroth dilution assay to be 64 µg/mL for both E. faecalis and S. aureus.

Key words

Verbesina negrensis - Asteraceae - antibacterial - germacrene

• References

• 1 Mabberley DJ. Mabberleyʼs plant-book. A portable dictionary of plants, their classifications, and uses, 3rd edition.. Seattle: Cambridge University Press; 2008
• 2 Dematteis M, Molero J, Angulo MB, Rovira AM. Chromosome studies on some Asteraceae from South America. Bot J Linn Soc 2007; 153: 221-230
• 3 Lobitz GO, Heilmann J, Zschocke S, Tamayo-Castillo G, Bauer R, Merfort I. Bornyl cinnamate derivatives with antiinflammatory activity from Verbesina turbacensis . Pharm Pharmacol Lett 1998; 8: 115-118
• 4 Network UNP. N.P.N U. Verbesina virginica . In: Network UNP, editor. Natureʼs Notebook. Tucson, AZ, USA: National Phenology Network; 2012
• 5 Shluker A. Verbesina encelioides [(Cav.) Bentham & Hooker fil. ex Gray] ssp. exauriculata [Robinson & Greenman]. Available at: http://hear.org/hnis/reports/verbesina_encelioides_hnis.pdf Accessed March 15, 2012
• 6 Amaro-Luis JM, Ramirez I, Delgado-Mendez P, Jorge ZD. Eudesmane derivatives from Verbesina turbacensis . J Braz Chem Soc 2002; 13: 352-357
• 7 Banerjee S, Jakupovic J, Bohlmann F, King RM, Robinson H. A rearranged eudesmane and further verbesindiol derivatives from Verbesina eggersii . Phytochemistry 1985; 24: 1106-1108
• 8 Bohlmann F, Zdero C. Naturally occurring terpene derivatives. Part 72. New terpene constituents from Verbesina species. Phytochemistry 1976; 15: 1310-1311
• 9 Bohlmann F, Lonitz M. Naturally occurring terpene derivatives. Part 123. New sesquiterpenes from Verbesina occidentalis . Phytochemistry 1978; 17: 453-455
• 10 Bohlmann F, Zdero C. Naturally occurring terpene derivatives. Part 224. The configuration of alpha- and beta-verbesinol coumarate. Phytochemistry 1979; 18: 1751-1752
• 11 Bohlmann F, Grenz M, Gupta RK, Dhar AK, Ahmed M, King RM, Robinson H. Naturally occurring terpene derivatives. Part 285. Eudesmane derivatives from Verbesina species. Phytochemistry 1980; 19: 2391-2397
• 12 Bohlmann F, Zdero C, Robinson H, King RM. Naturally occurring terpene derivatives. Part 409. Two new eudesmane cinnamates from Verbesina sordescens . Phytochemistry 1982; 21: 1663-1664
• 13 Box VGS, Chan WR, Taylor DR. Structure of rupestrol, a new sesquiterpenoid from Verbesina rupestris . Tetrahedron Lett 1971; 4371-4374
• 14 Box VGS, Chan WR. Terpenoids from Verbesina rupestris . Phytochemistry 1975; 14: 583
• 15 Box VGS, Bardouille V, Chan WR. Enantio-eudesmane sesquiterpenes from Verbesina rupestris . Phytochemistry 1977; 16: 987-990
• 16 Castro V, Jakupovic J, Bohlmann F. New oplodiol derivatives from Verbesina oerstediana . Rev Latinoam Quim 1984; 15: 111-114
• 17 Dominguez XA, Sanchez H, Franco R, Slim J, Ellmauerer E. Constituents from Verbesina oncophora V. lindheimeri . Rev Latinoam Quim 1987; 18: 113
• 18 Gardner PD, Park GJ, Albers CC. Alpha- and beta-Verbesinol. Sesquiterpene alcohols of the cis-decahydronaphthalene series. J Am Chem Soc 1961; 83: 1511-1512
• 19 Guerrero C, Iriarte A, Diaz E, Taboada J, Gonzalez DM, Tellez J. Determination of the structure and stereochemistry of elemenolide verafinin C and isolation of verafinin B, cytotoxic substances isolated from Verbesina coahuilensis . Rev Latinoam Quim 1975; 6: 119-123
• 20 Guerrero C, Martinez M, Diaz E, Romo de Vivar A. Elemenolides. II. Structure and stereochemistry of veratinin, a new elemenolide isolated from Verbesina coahuilensis . Rev Latinoam Quim 1975; 6: 53-56
• 21 Guerrero C, Diaz E. Structure of verafinin B, a new elemanolide isolated from Verbesina aff coahuilensis . Rev Latinoam Quim 1983; 14: 70-72
• 22 Herz W, Kumar N. Aromatic and other constituents of four Verbesina species: structure and stereochemistry of verbesindiol. Phytochemistry 1981; 20: 247-250
• 23 Ortega A, Martinez R, Romo de Vivar A. Elemanolides of Verbesina aff stricta. Structure of zempoalines A and B. Rev Latinoam Quim 1977; 8: 166-168
• 24 Martinez M, Romo de Vivar A, Ortega A, Quintero MdL, Garcia C, Fronczek FR. Eudesmane triols from Verbesina virgata . Phytochemistry 1983; 22: 979-982
• 25 Ortega A, Maldonado E, Fronczek FR, Delord TJ, Chiari G. Elemanolides from Verbesina seattonii . Phytochemistry 1985; 24: 1755-1760
• 26 Delle Monache G, Botta B, Delle Monache F, Espinal R, De BSC, De LC, Botta M, Corelli F, Carmignani M. Caracasanamide, a novel hypotensive agent from Verbesina caracasana . Bioorg Med Chem Lett 1992; 2: 415-418
• 27 Delle Monache G, Botts B, Delle Monache F, Espinal R, De Bonnevaux SC, De Luca C, Botta M, Corelli F, Dei D, Gacs-Baitz E, Carmignani M. Novel hypotensive agents from Verbesina caracasana. 3. Caracasandiamide, a truxinic hypotensive agent from Verbesina caracasana . Bioorg Med Chem Lett 1996; 6: 233-238
• 28 Delle Monache G, Volpe AR, Delle Monache F, Vitali A, Botta B, Espinal R, De Bonnevaux SC, De Luca C, Botta M, Corelli F, Carmignani M. Novel hypotensive agents from Verbesina caracasana. 7. Further hypotensive metabolites from Verbesina caracasana . Bioorg Med Chem Lett 1999; 9: 3249-3254
• 29 Eichholzer JV, Lewis IAS, MacLeod JK, Oelrichs PB, Vallely PJ. Galegine and a new dihydroxyalkylacetamide from Verbesina enceloiodes . Phytochemistry 1982; 21: 97-99
• 30 Glennie CW, Jain SC. Flavonol 3, 7-diglycosides of Verbesina encelioides . Phytochemistry 1980; 19: 157-158
• 31 Oelrichs PB, Vallely PJ, MacLeod JK, Lewis IAS. Isolation of galegine from Verbesina enceloiodes . J Nat Prod 1981; 44: 754-755
• 32 Wagner H, Iyengar MA, Seligmann O, Herz W. Rhamnocitrin-3-glucuronide in Verbesina myriocephala . Phytochemistry 1974; 13: 493-494
• 33 Xu WH, Jacob MR, Agarwal AK, Clark AM, Liang ZS, Li XC. Verbesinosides A–F, 15, 27-Cyclooleanane Saponins from the American Native Plant Verbesina virginica . J Nat Prod 2009; 72: 1022-1027
• 34 Pagliero RJ, Mercado R, McCracken V, Mazzieri MR, Nieto MJ. Rapid and facile synthesis of N-benzenesulfonyl derivatives of heterocycles and their antimicrobial properties. Lett Drug Des Discov 2011; 8: 778-791