caa a22 4500 605504008 CHVBK 20210128100613.0 cr unu---uuuuu 210128e20150401xx s 000 0 eng 10.1007/s00253-015-6431-6 doi (NATIONALLICENCE)springer-10.1007/s00253-015-6431-6 Structural modification of herboxidiene by substrate-flexible cytochrome P450 and glycosyltransferase [Elektronische Daten] [Amit Jha, Dipesh Dhakal, Pham Van, Anaya Pokhrel, Tokutaro Yamaguchi, Hye Jung, Yeo Yoon, Jae Sohng] 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. Springer-Verlag Berlin Heidelberg, 2015 Streptomyces nationallicence Glycosylation nationallicence Hydroxylation nationallicence Epoxidation nationallicence Antibacterial nationallicence Jha Amit Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut Dhakal Dipesh Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut Van Pham Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut Pokhrel Anaya Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut Yamaguchi Tokutaro Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut Jung Hye Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut Yoon Yeo Department of Chemistry and Nano Science, Ewha Womans University, 120-750, Seoul, Republic of Korea aut Sohng Jae Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut Applied Microbiology and Biotechnology Springer Berlin Heidelberg 99/8(2015-04-01), 3421-3431 0175-7598 99:8<3421 2015 99 253 https://doi.org/10.1007/s00253-015-6431-6 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00253-015-6431-6 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Jha Amit Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut NATIONALLICENCE 700 1- Dhakal Dipesh Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut NATIONALLICENCE 700 1- Van Pham Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut NATIONALLICENCE 700 1- Pokhrel Anaya Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut NATIONALLICENCE 700 1- Yamaguchi Tokutaro Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut NATIONALLICENCE 700 1- Jung Hye Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut NATIONALLICENCE 700 1- Yoon Yeo Department of Chemistry and Nano Science, Ewha Womans University, 120-750, Seoul, Republic of Korea aut NATIONALLICENCE 700 1- Sohng Jae Institute of Biomolecule Reconstruction (iBR), Department of BT-Convergent Pharmaceutical Engineering, Sun Moon University, 70, Sunmoon-Ro221, Tangjeong-myeon, 333-708, Asan, Chungnam, Republic of Korea aut NATIONALLICENCE 773 0- Applied Microbiology and Biotechnology Springer Berlin Heidelberg 99/8(2015-04-01), 3421-3431 0175-7598 99:8<3421 2015 99 253