Download PDF
Planta Med 2004; 70(11): 1087-1090
DOI: 10.1055/s-2004-832653
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Potent Antibacterial Activity of Halogenated Compounds against Antibiotic-Resistant Bacteria

Charles Santhanaraju Vairappan1 , Tomotake Kawamoto2 , 4 , Hideaki Miwa3 , Minoru Suzuki2 , 5
  • 1Laboratory of Marine Natural Product Chemistry, Borneo Marine Research Institute, Universiti Malaysia Sabah, Kota Kinabalu, Sabah, Malaysia
  • 2Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo, Japan
  • 3Discovery Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan
  • 4Present address: Tama Laboratory, Japan Food Research Laboratories, Tama, Japan
  • 5Present address: Borneo Marine Research Institute, Universiti Malaysia Sabah, Kota Kinabalu, Sabah, Malaysia
Further Information

Publication History

Received: February 6, 2004

Accepted: May 15, 2004

Publication Date:
18 November 2004 (online)

    Permissions and Reprints

Abstract

Common Gram-positive clinical pathogens are showing an increasing trend for resistance to conventional antimicrobial agents. New drugs with potent antibacterial activities are urgently needed to remediate this problem. Halogenated compounds isolated from several species of the red algae genus Laurencia were examined for their antibacterial activity against 22 strains of human pathogenic bacteria, 7 strains of which were antibiotic-resistant bacteria. Four phenolic sesquiterpenes and a polybrominated indole showed wide spectra of antibacterial activity against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), penicillin-resistant Streptococcus pneumoniae, and vancomycin-resistant Enterococcus faecalis and E. faecium (VRE). In addition, laurinterol and allolaurinterol displayed potent bactericidal activity against three strains of MRSA at 3.13 μg mL-1, and three strains of vancomycin-susceptible Enterococcus, at 3.13 μg mL-1 and 6.25 μg mL-1, respectively.

References

  • 1 Panlilio A L, Culver D H, Gaynes R P. et al . Methicillin-resistant S. aureus in US hospitals, 1975 - 1991.  Infection Control Hospital Epidemiol. 1992;  13 582-6
    PubMedGoogle Scholar
  • 2 Moellering R C. Vancomycin-resistant enterococci.  Clin Infect Dis. 1998;  26 1196-9
    PubMedGoogle Scholar
  • 3 Diekema D J, Jones R N. Oxazolidinone antibiotics.  Lancet. 2001;  358 1975-82
    CrossrefPubMedGoogle Scholar
  • 4 Erickson K L. Marine Natural Products: Chemical and Biological Perspectives. Constituents of Laurencia. In: Scheuer PJ, editor Vol. 5 Academic Press New York; 1983: pp 131-257
    Google Scholar
  • 5 Waraszkiewicz S M, Erickson K L. Halogenated sesquiterpenoids from the Hawaiian marine alga Laurencia nidifica: nidificene and nidifidiene. Tetrahedron Lett 1974: 2003-6
    Google Scholar
  • 6 Wratten S J, Faulkner D J. Metabolites of the red alga Laurencia subopposita .  J Org Chem. 1977;  42 3343-9
    PubMedGoogle Scholar
  • 7 Carter G T, Rinehart K L, Li L H, Kuentzel S L, Connor J L. Brominated indoles from Laurencia brongniartii . Tetrahedron Lett 1978: 4479-82
    Google Scholar
  • 8 Caccamese S, Azzolina R, Duesler E N, Paul I C, Rinehart K L. Laurencienyne, a new acetylenic cyclic ether from the marine red alga Laurencia obtusa .  Tetrahedron Lett. 1980;  21 2299-302
    CrossrefPubMedGoogle Scholar
  • 9 König G M, Wright A W. Sesquiterpene content of the antibacterial dichloromethane extract of the marine red alga Laurencia obtusa .  Planta Medica. 1997;  63 186-7
    PubMedGoogle Scholar
  • 10 Vairappan C S, Daitoh M, Suzuki M, Abe T, Masuda M. Antibacterial halogenated metabolites from the Malaysian Laurencia species.  Phytochemistry. 2001;  58 291-7
    CrossrefPubMedGoogle Scholar
  • 11 Vairappan C S, Suzuki M, Abe T, Masuda M. Halogenated metabolites with antibacterial activity from the Okinawan Laurencia species.  Phytochemistry. 2001;  58 517-23
    CrossrefPubMedGoogle Scholar
  • 12 Vairappan C S. Potent antibacterial activity of halogenated metabolites from Malaysian red algae, Laurencia majuscula (Rhodomelaceae, Ceramiales).  Biomol Engineering. 2003;  20 255-9
    PubMedGoogle Scholar
  • 13 Suzuki M, Kurosawa E. Halogenated and non-halogenated aromatic sesquiterpenes from the red algae Laurencia okamurai Yamada.  Bull Chem Soc Japan. 1979;  52 3352-4
    PubMedGoogle Scholar
  • 14 Kazlauskas R, Murphyi P T, Quinn R J, Wells R J. New laurene derivatives from Laurencia filiformis .  Aust J Chem. 1976;  29 2533-9
    PubMedGoogle Scholar
  • 15 Ichiba T, Higa T. New cuparene-derived sesquiterpenes with unprecedented oxygenation patterns from the sea hare Aplysia dactylomela .  J Org Chem. 1986;  51 3364-6
    PubMedGoogle Scholar
  • 16 Sims J J, Lin G HY, Wing R M. Marine natural product X. Elatol, a halogenated sesquiterpene alcohol from the red alga Laurencia elata . Tetrahedron Lett 1974: 3487-90
    Google Scholar
  • 17 Gonzalez A G, Martin J D, Martin V S, Martinez-Ripoli M, Fayos J. X-ray studies of sesquiterpene constituents of the alga L. obtusa leads to structure revision. Tetrahedron Lett 1979: 2717-8
    Google Scholar
  • 18 Masuda M, Kawaguchi S, Abe T, Kawamoto T, Suzuki M. Additional analysis of chemical diversity of the red algal genus Laurencia (Rhodomelaceae) from Japan.  Phycol Res. 2002;  50 135-44
    CrossrefPubMedGoogle Scholar
  • 19 Masuda M, Kawaguchi S, Takahashi Y, Okamoto K, Suzuki M. Halogenated secondary metabolites of Laurencia similis (Rhodomelaceae, Rhodophyta).  Botanica Marina. 1999;  42 199-202
    CrossrefPubMedGoogle Scholar

Dr. Charles S. Vairappan

Laboratory of Marine Natural Product Chemistry

Borneo Marine Research Institute

Universiti Malaysia Sabah

88999 Kota Kinabalu

Sabah

Malaysia

Phone: +60-88-320000 (ext. 2587)

Fax: +60-88-320261

Email: csv@ums.edu.my

      >