Antibacterial Sesquiterpenoid Derivatives from Ferula
                        ferulaeoides

Tao Liu; Khadijo Osman; Glenn W. Kaatz; Simon Gibbons; Qing Mu

doi:10.1055/s-0032-1328461

Planta Medica, Table of Contents

Planta Med 2013; 79(08): 701-706
DOI: 10.1055/s-0032-1328461

Natural Product Chemistry

Letters

Georg Thieme Verlag KG Stuttgart · New York

Antibacterial Sesquiterpenoid Derivatives from Ferula ferulaeoides

Tao Liu

¹School of Pharmacy, Fudan University, Shanghai, China

,

Khadijo Osman

²Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, London, United Kingdom

,

Glenn W. Kaatz

³The John D. Dingell Department of Veteranʼs Affairs Medical Center and Department of Internal Medicine, Division of Infectious Diseases, School of Medicine, Wayne State University, Detroit, Michigan, USA

,

Simon Gibbons

²Department of Pharmaceutical and Biological Chemistry, UCL School of Pharmacy, London, United Kingdom

,

Qing Mu

¹School of Pharmacy, Fudan University, Shanghai, China

› Author Affiliations

Abstract

Three new sesquiterpenoid derivatives 1, 2, and 3 were isolated from Ferula ferulaeoides. To confirm the structure, compound 2 was also synthesized via a condensation reaction between compound 1 and 2,2-dimethoxypropane. The structures of these three compounds were elucidated by means of spectroscopic and chemical methods. Their antibacterial activity against drug-resistant Staphylococcus aureus strains were evaluated with MIC values in the range of 0.5–128 µg/mL. Compounds 1 and 3 were capable of inhibiting efflux of ethidium bromide using an in vitro assay. The cytotoxicity of the compounds was evaluated on cultured HEK293 cells, and none of them showed toxicity to HEK293 cells at a concentration of 125 µg/mL.

Key words

Ferula ferulaeoides - Apiaceae - sesquiterpenoid - efflux inhibition - drug-resistant Staphylococcus aureus

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References

References
1 Fisher JF, Meroueh SO, Mobashery S. Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity. Chem Rev 2005; 105: 395-424
2 Crowcroft NE, Catchpole M. Mortality from methicillin resistant Staphylococcus aureus in England and Wales: analysis of death certificates. Br Med J 2002; 325: 1390-1391
3 Akins RL, Rybak MJ. Bactericidal activities of two daptomycin regimens against clinical strains of glycopeptide intermediate-resistant Staphylococcus aureus, vancomycin-resistant Enterococcus faecium, and methicillin-resistant Staphylococcus aureus isolates in an in vitro pharmacodynamic model with simulated endocardial vegetations. Antimicrob Agents Chemother 2001; 45: 454-459
4 Patel R. Clinical impact of vancomycin-resistant enterococci. J Antimicrob Chemother 2003; 51: 13-21
5 Wesson KM, Lerner DS, Silverberg NB, Weinberg JM. Linezolid, quinupristin/dalfopristin, and daptomycin in dermatology. Dis Mon 2004; 50: 395-406
6 Jabrane A, Ben jannet H, Skhiri FH, Miyamoto T, Lacaille-Dubois MA. Phytochemical study from the roots of Ferula lutea L. Planta Med 2008; 74: 1073
7 Nazari ZE, Iranshahi M. Biologically active sesquiterpene coumarins from Ferula species. Phytother Res 2011; 25: 315-323
8 Xinjiang Institute of Biology, Pedology and Desert Research (XIBPDR). Flora of medicinal plant in Xinjiang. Wulumuqi: Xinjiang Peopleʼs Press; 1977: 116
9 Nagatsu A, Isaka K, Kojima K, Ondognii P, Zevgeegiin O, Gombosurengyin P, Davgiin K, Irfan B, Iqubal CM, Ogihara Y. New sesquiterpenes from Ferula ferulaeoides (Steud.) Korovin. VI. Isolation and identification of three new dihydrofuro[2,3-b]chromones. Chem Pharm Bull 2002; 50: 675-677
10 Kamilov KM, Niknov GK. Dshamirone, a new ketone from Ferula dshaudshamyr roots. Khim Prir Soedin 1976; 6: 817-818
11 Kojima K, Isaka K, Purev O, Jargalsaikhan G, Suran D, Mizukami H, Ogihara Y. Sesquiterpenoid derivatives from Ferula ferulioides . Chem Pharm Bull 1998; 46: 1781-1784
12 Lange GL, Humber CC, Manthorpe JM. [2 + 2] Photoadditions with chiral 2,5-cyclohexadienone synthons. Tetrahedron Asymm 2002; 13: 1355-1362
13 Kojima K, Isaka K, Purev O, Jargalsaikhan G, Suran D, Mizukami H, Ogihara Y. Sesquiterpenoid derivatives from Ferula ferulioides. II. Chem Pharm Bull 1999; 47: 1145-1147
14 Gibbons S, Udo EE. The effect of reserpine, a modulator of multidrug efflux pumps, on the in vitro activity of tetracycline against clinical isolates of methicillin resistant Staphylococcus aureus (MRSA) possessing the tet(K) determinant. Phytother Res 2000; 14: 139-140
15 Kaatz GW, Seo SM, Ruble CA. Efflux-mediated fluoroquinolone resistance in Staphylococcus aureus . Antimicrob Agents Chemother 1993; 37: 1086-1094
16 Ross JI, Farrell AM, Eady EA, Cove JH, Cunliffe WJ. Characterization and molecular cloning of the novel macrolide-streptogramin B resistance determinant from Staphylococcus epidermidis . J Antimicrob Chemother 1989; 24: 851-862
17 Richardson JF, Reith S. Characterisation of a strain of methicillin-resistant Staphylococcus aureus (EMRSA-15) by conventional and molecular methods. J Hosp Infect 1993; 25: 45-52

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