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Journal of Natural Medicines

, Volume 71, Issue 2, pp 357–366 | Cite as

Lupinifolin from Derris reticulata possesses bactericidal activity on Staphylococcus aureus by disrupting bacterial cell membrane

  • Kamol Yusook
  • Oratai Weeranantanapan
  • Yanling Hua
  • Pakarang Kumkrai
  • Nuannoi ChudapongseEmail author
Original Paper

Abstract

In this study, lupinifolin, a prenylated flavonoid, was isolated from Derris reticulata stem, identified by NMR spectra and confirmed with mass spectrometry. Lupinifolin was freshly prepared by solubilizing in 0.1 N NaOH and immediately diluted in Müller–Hinton broth for antibacterial testing. The data showed that Gram-positive bacteria were more susceptible to lupinifolin than Gram-negative bacteria. Of four strains of Gram-positive bacteria tested, Staphylococcus aureus was the most susceptible. Using the two-fold microdilution method, it was found that lupinifolin possessed antimicrobial activity against S. aureus with minimum inhibitory concentration and minimum bactericidal concentration of 8 and 16 µg/ml, respectively, which is less potent than ampicillin. However, from the time–effect relationship, it was shown that lupinifolin had faster onset than ampicillin. The faster onset of lupinifolin was confirmed by scanning electron microscopy. To investigate the mechanism of action of lupinifolin, transmission electron microscopy (TEM) was performed to observe the ultrastructure of S. aureus. The TEM images showed that lupinifolin ruptured the bacterial cell membrane and cell wall. Due to its fast onset, it is suggested that the action of lupinifolin is likely to be the direct disruption of the cell membrane. This hypothesis was substantiated by the data from flow cytometry using DiOC2 as an indicator. The result showed that the red/green ratio which indicated bacterial membrane integrity was significantly decreased, similar to the known protonophore carbonyl cyanide 3-chlorophenylhydrazone. It is concluded that lupinifolin inhibits the growth of S. aureus by damaging the bacterial cytoplasmic membrane.

Keywords

Derris reticulata Lupinifolin Staphylococcus aureus Antimicrobial Cell membrane disruption 

Notes

Acknowledgements

We thank Dr. Paul J. Grote for verification of plant botanical classification.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11418_2016_1065_MOESM1_ESM.png (9 kb)
S1. 1H-NMR signal of lupinifolin (PNG 9 kb)
11418_2016_1065_MOESM2_ESM.png (11 kb)
S2. 13C-NMR signal of lupinifolin (PNG 10 kb)

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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan 2016

Authors and Affiliations

  • Kamol Yusook
    • 1
  • Oratai Weeranantanapan
    • 1
  • Yanling Hua
    • 2
  • Pakarang Kumkrai
    • 3
  • Nuannoi Chudapongse
    • 1
    Email author
  1. 1.School of Preclinical Sciences, Institute of ScienceSuranaree University of TechnologyNakhon RatchasimaThailand
  2. 2.The Center for Scientific and Technological EquipmentSuranaree University of TechnologyNakhon RatchasimaThailand
  3. 3.Division of Health Promotion, Faculty of Health ScienceSrinakharinwirot UniversityOngkharakThailand

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