The antibacterial properties of 6-tuliposide B. Synthesis of 6-tuliposide B analogues and structure-activity relationship

Phytochemistry
Kengo ShigetomiMakoto Ubukata

Abstract

6-Tuliposide B is a secondary metabolite occurring specifically in tulip anthers. Recently, a potent antibacterial activity of 6-tuliposide B has been reported. However, its molecular target has not yet been established, nor its action mechanism. To shed light on such issues, 6-tuliposide B and tulipalin B analogues were synthesized and a structure-activity relationship (SAR) was examined using a broad panel of bacterial strains. As the results of SAR among a total of 25 compounds, only tulipalin B and the compounds having 3',4'-dihydroxy-2'-methylenebutanoate (DHMB) moieties showed any significant antibacterial activity. Moreover, the 3'R analogues of these compounds displayed essentially the same activities as 6-tuliposide B and the structure of the 3'R-DMBA moiety was the same as that of the proposed active moiety of cnicin. These results suggest that 6-tuliposide B has the same action mechanism as proposed for cnicin and bacterial MurA is one of the major molecular targets of 6-tuliposide B.

References

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Citations

Dec 10, 2013·Bioscience, Biotechnology, and Biochemistry·Kengo ShigetomiMakoto Ubukata
Aug 24, 2010·Bioorganic & Medicinal Chemistry Letters·Thomas MendgenChristian D Klein
May 21, 2013·Journal of Basic Microbiology·Sanne H OlesenErnst Schönbrunn
May 23, 2015·The Plant Journal : for Cell and Molecular Biology·Taiji NomuraYasuo Kato
Apr 24, 2014·Bioorganic Chemistry·Martina HrastStanislav Gobec
Oct 5, 2016·Bioscience, Biotechnology, and Biochemistry·Taiji Nomura
Mar 22, 2018·Bioscience, Biotechnology, and Biochemistry·Makoto Ubukata
Apr 23, 2011·Bioscience, Biotechnology, and Biochemistry·Kengo ShigetomiMakoto Ubukata
May 8, 2013·Bioscience, Biotechnology, and Biochemistry·Taiji NomuraYasuo Kato
Feb 25, 2020·Zeitschrift Für Naturforschung. C, a Journal of Biosciences·Taiji Nomura, Yasuo Kato

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