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Structural modification of herboxidiene by substrate-flexible cytochrome P450 and glycosyltransferase

Title
Structural modification of herboxidiene by substrate-flexible cytochrome P450 and glycosyltransferase
Authors
Jha A.K.Dhakal D.Van P.T.T.Pokhrel A.R.Yamaguchi T.Jung H.J.Yoon Y.J.Sohng J.K.
Ewha Authors
윤여준
SCOPUS Author ID
윤여준scopus
Issue Date
2015
Journal Title
Applied Microbiology and Biotechnology
ISSN
1757-7598JCR Link
Citation
vol. 99, no. 8, pp. 3421 - 3431
Keywords
AntibacterialEpoxidationGlycosylationHydroxylationStreptomyces
Publisher
Springer Verlag
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Herboxidiene is a natural product produced by Streptomyces chromofuscus exhibiting herbicidal activity as well as antitumor properties. Using different substrate-flexible cytochrome P450s and glycosyltransferase, different novel derivatives of herboxidiene were generated with structural modifications by hydroxylation or epoxidation or conjugation with a glucose moiety. Moreover, two isomers of herboxidiene containing extra tetrahydrofuran or tetrahydropyran moiety in addition to the existing tetrahydropyran moiety were characterized. The hydroxylated products for both of these compounds were also isolated and characterized from S. chromofuscus PikC harboring pikC from the pikromycin gene cluster of Streptomyces venezuelae and S. chromofuscus EryF harboring eryF from the erythromycin gene cluster of Saccharopolyspora erythraea. The compounds generated were characterized by high-resolution quadrupole-time-of-flight electrospray ionization mass spectrometry (HR-QTOF-ESI/MS) and 1H- and 13C-nuclear magnetic resonance (NMR) analyses. The evaluation of antibacterial activity against three Gram-positive bacteria, Micrococcus luteus, Bacillus subtilis, and Staphylococcus aureus, indicated that modification resulted in a transition from anticancer to antibacterial potency. © 2015, Springer-Verlag Berlin Heidelberg.
DOI
10.1007/s00253-015-6431-6
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자연과학대학 > 화학·나노과학전공 > Journal papers
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