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. 2009 May 27;32(5):655–659. doi: 10.1007/s12272-009-1502-9

Antibacterial activity of two phloroglucinols, flavaspidic acids AB and PB, from Dryopteris crassirhizoma

Hyang Burm Lee 1,✉, Jin Cheol Kim 2, Sang Myung Lee 3,✉
PMCID: PMC7091015  PMID: 19471878

Abstract

The antimicrobial effect of solvent extracts from the rhizome of a thick-stemmed wood fern (Dryopteris crassirhizoma) was evaluated and its phloroglucinol components, flavaspidic acids PB and AB. Flavaspidic acids PB and AB were isolated from the D. crassirhizoma rhizomes by methanol extraction, followed by silica gel and Sephadex LH-20 column chromatography. The chemical structures were characterized by spectral techniques, including ESI-MS, UV, 1H- and 13C-NMR spectrum analysis. When the antimicrobial activity of the extracts and compounds was tested by the paper disc method, the extracts and compounds were highly active against Gram-positive bacteria, such as methicillin-resistant Staphylococcus aureus KCTC 1928 (a MRSA bacterium), Streptococcus mutans and Bacillus subtilis. The extracts and compounds were not active against fungi and chlorella. Our study revealed that the antibacterial activity of samples from D. crassirhizoma was mainly related to the flavaspidic acids.

Key words: Antibacterial activity, Phloroglucinols, Flavaspidic acids, Dryopteris crassirhizoma

Contributor Information

Hyang Burm Lee, Email: hblee@jnu.ac.kr.

Sang Myung Lee, Email: smlee@ktng.com.

References

  1. Dharmananda, S., SARS AND CHINESE MEDICINE. How the Chinese People and Institutions Responded with Herbs: http://www.itmonline.org/arts/sars.htm (2003).
  2. Do D. S. Antibacterial components of Dryopteris crassirhizoma against a Streptococcus mutans OMZ 176. Daejeon, Korea: Chungnam National University.; 1993. [Google Scholar]
  3. Govind J. K., Harukuni T., Takao K., Midori T., Junko T., Hoyoku N. Anti-tumor promoting activity of Dryopteris phlorophenone derivatives. Cancer Letters. 1996;105:161–165. doi: 10.1016/0304-3835(96)04275-9. [DOI] [PubMed] [Google Scholar]
  4. Hideo N., Munehisa A., Akio F., Saburo K., Katsuhiko O. Inhibition of HIV-reverse transcriptase activity by some phloroglucinol derivatives. FEBS Letters. 1991;286:83–85. doi: 10.1016/0014-5793(91)80946-Z. [DOI] [PubMed] [Google Scholar]
  5. Kang K. A., Lee K. H., Chae S., Zhang R., Jung M. S., Ham Y. M., Baik J. S., Lee N. H., Hyun J. W. Cytoprotective effect of phloroglucinol on oxidative stress induced cell damage via catalase activation. J. Cell Biochem. 2006;97:609–620. doi: 10.1002/jcb.20668. [DOI] [PubMed] [Google Scholar]
  6. Lee S. M., Na M. K., An R. B., Min B. S., Lee H. K. Antioxidant activity of two phloroglucinol derivatives from Dryopteris crassirhizoma. Biol. Pharm. Bull. 2003;26:1354–1356. doi: 10.1248/bpb.26.1354. [DOI] [PubMed] [Google Scholar]
  7. Mathekga A. D. M., Meyer J. J. M., Horn M. M., Drewes S. E. An acylated phloroglucinol with antimicrobial properties from Helichrysum caespititium. Phytochemistry. 2000;53:93–96. doi: 10.1016/S0031-9422(99)00424-0. [DOI] [PubMed] [Google Scholar]
  8. Min B. S., Tomiyama M., Ma C. M., Nakamura N., Hattori M. Kaempferol Acetylrhamnosides from the rhizome of Dryopteris crassirhizoma and their inhibitory effects on three different activities of human immunodeficiency Virus-I reverse transcriptase. Chem. Pharm. Bull. 2001;49:546–550. doi: 10.1248/cpb.49.546. [DOI] [PubMed] [Google Scholar]
  9. Na M., Jang J., Min B. S., Lee S. J., Lee M. S., Kim B. Y., Oh W. K., Ahn J. S. Fatty acid synthase inhibitory activity of acylphloroglucinols isolated from Dryopteris crassirhizoma. Bioorg. Med. Chem. Lett. 2006;16:4738–4742. doi: 10.1016/j.bmcl.2006.07.018. [DOI] [PubMed] [Google Scholar]
  10. Namba T., Tsunezuka M., Hattori M. Dental caries prevention by traditional Chinese medicines. Planta Medica. 1982;44:100–106. doi: 10.1055/s-2007-971412. [DOI] [PubMed] [Google Scholar]
  11. Namba T. The encyclopedia of Wakan-Yaku with Color Picture Vol. I. Osaka, Japan: Hoikusha Co., Ltd.; 1993. pp. 142–144. [Google Scholar]
  12. Noro Y., Okuda K., Hisada S., Inagaki I., Tanaka T., Yokohashi H. Dryocrassin: A new acylphloroglucinol from Dryopteris crassirhizoma. Phytochemistry. 1973;12:1491–1493. doi: 10.1016/0031-9422(73)80591-6. [DOI] [Google Scholar]
  13. Rie I., Masakazu H., Koichi S., Munehisa A., Susumu K. Inhibitory effects of phloroglucinol derivatives from Mallotus japonicus on nitric oxide production by a murine macrophage-like cell line, RAW 264.7, activated by lipopolysaccharide and interferon-γ. Biochimica et Biophysica Acta — General Subjects. 2001;1568:74–82. doi: 10.1016/S0304-4165(01)00203-3. [DOI] [PubMed] [Google Scholar]
  14. Widen C. -J., Fraser-Jenkins C. R., Reichstein T., Gibby M., Sarvela J. Phloroglucinol derivatives in Dryopteris sect. Fibrillosae and related taxa (Pteridophyta, Dryopteridaceae) Ann. Bot. Fennici. 1996;33:69–100. [Google Scholar]

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