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

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• 作者：Amit Kumar Jha (1)
  Dipesh Dhakal (1)
  Pham Thi Thuy Van (1)
  Anaya Raj Pokhrel (1)
  Tokutaro Yamaguchi (1)
  Hye Jin Jung (1)
  Yeo Joon Yoon (2)
  Jae Kyung Sohng (1)
  
  1. Institute of Biomolecule Reconstruction (iBR) ; Department of BT-Convergent Pharmaceutical Engineering ; Sun Moon University ; 70 ; Sunmoon-Ro221 ; Tangjeong-myeon ; Asan ; Chungnam ; 333-708 ; Republic of Korea
  2. Department of Chemistry and Nano Science ; Ewha Womans University ; Seoul ; 120-750 ; Republic of Korea
  
• 关键词：Streptomyces ; Glycosylation ; Hydroxylation ; Epoxidation ; Antibacterial
• 刊名：Applied Microbiology and Biotechnology
• 出版年：2015
• 出版时间：April 2015
• 年：2015
• 卷：99
• 期：8
• 页码：3421-3431
• 全文大小：579 KB
• 参考文献：1. Banwell, M, McLeod, M, Premraj, R, Simpson, G (2000) Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847. Pure Appl Chem 72: pp. 1631-1634 CrossRef
  2. Bierman, M, Logan, R, O鈥橞rien, K, Seno, ET, Nagaraj, R, Schoner, BE (1992) Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116: pp. 43-49 CrossRef
  3. Blakemore, PR, Kocienski, PJ, Morley, A, Muir, K (1999) A synthesis of herboxidiene. J Chem Soc Perkin Trans 1999: pp. 955-968 CrossRef
  4. Blanchard, S, Thorson, JS (2006) Enzymatic tools for engineering natural product glycosylation. Curr Opin Chem Biol 10: pp. 263-271 CrossRef
  5. Bonnal, S, Vigevani, L, Valc谩rcel, J (2012) The spliceosome as a target of novel antitumour drugs. Nat Rev Drug Discov 11: pp. 847-859 CrossRef
  6. Chaudhary, AK, Dhakal, D, Sohng, JK (2013) An insight into the 鈥?Omics鈥?based engineering of streptomycetes for secondary metabolite overproduction. Biomed Res Int 2013: pp. 968518 CrossRef
  7. Edmunds, AJF, Trueb, W, Oppolzer, W, Cowley, P (1997) Herboxidiene: determination of absolute configuration by degradation and synthetic studies. Tetrahedron 53: pp. 2785-2802 CrossRef
  8. Edmunds, AJ, Arnold, G, Hagmann, L, Schaffner, R, Furlenmeier, H (2000) Synthesis of simplified herboxidiene aromatic hybrids. Bioorg Med Chem Lett 10: pp. 1365-1368 CrossRef
  9. Effenberger, KA, Anderson, DD, Bray, WM, Prichard, BE, Ma, N, Adams, MS, Ghosh, AK, Jurica, MS (2014) Coherence between cellular responses and in vitro splicing inhibition for the anti-tumor drug pladienolide B and its analogs. J Biol Chem 289: pp. 1938-1947 CrossRef
  10. Gantt, RW, Peltier-Pain, P, Thorson, JS (2011) Enzymatic methods for glycol (diversification/randomization) of drugs and small molecules. Nat Prod Rep 28: pp. 1811-1853 CrossRef
  11. Gao, Y, Vogt, A, Forsyth, CJ, Koide, K (2013) Comparison of splicing factor 3b inhibitors in human cells. ChemBioChem 14: pp. 49-52 CrossRef
  12. Ghosh, AK, Li, J (2011) A stereoselective synthesis of (+)-herboxidiene/GEX1A. Org Lett 13: pp. 66-69 CrossRef
  13. Hasegawa, M, Miura, T, Kuzuya, K, Inoue, A, Won, KS, Horinouchi, S, Yoshida, T, Kunoh, T, Koseki, K, Mino, K, Sasaki, R, Yoshida, M, Mizukami, T (2011) Identification of SAP155 as the target of GEX1A (herboxidiene), an antitumor natural product. ACS Chem Biol 6: pp. 229-233 CrossRef
  14. Hunt, I (2014) Chapter 16: Ethers, epoxides and sulfides. Department of Chemistry, University of Calgary. http://www.chem.ucalgary.ca/courses/350/Carey5th/Ch16/ch16-6-1.html. Accessed 21 Nov 2014
  15. Isaac, BG, Ayer, SW, Elliott, RC, Stonard, RJ (1992) Herboxidiene: a potent phytotoxic polyketide from Streptomyces sp. A7847. J Org Chem 57: pp. 7220-7226 CrossRef
  16. Jha, AK, Lamichhane, J, Sohng, JK (2014) Enhancement of herboxidiene production in Streptomyces chromofuscus ATCC 49982. J Microbiol Biotechnol 24: pp. 52-58 CrossRef
  17. Johnson, AW (1999) Invitation to organic chemistry. Jones and Bartlett, Mississauga
  18. Khosla, C, Keasling, JD (2003) Metabolic engineering for drug discovery and development. Nat Rev Drug Discov 2: pp. 1019-1025 CrossRef
  19. Kieser, T, Mervyn, JB, Mark, BJ, Keith, CF, David, HA (2000) Practical Streptomyces genetics. John Innes Foundation Norwich, UK
  20. Koguchi, Y, Nishio, M, Kotera, J, Omori, K, Ohnuki, T, Komatsubara, S (1997) Trichostatin A and herboxidiene up-regulate the gene expression of low density lipoprotein receptor. J Antibiot (Tokyo) 50: pp. 970-971 CrossRef
  21. Kren, V, Martinkova, L (2001) Glycosides in medicine: 鈥渢he role of glycosidic residue in biological activity鈥? Curr Med Chem 8: pp. 1303-1328 CrossRef
  22. Lagisetti, C, Yermolina, MV, Sharma, LK, Palacios, G, Prigaro, BJ, Webb, TR (2013) Pre-mRNA splicing-modulatory pharmacophores: the total synthesis of herboxidiene, a pladienolide鈥揾erboxidiene hybrid analog and related derivatives. ACS Chem Biol 9: pp. 643-648 CrossRef
  23. Le, TT, Pandey, RP, Gurung, RB, Dhakal, D, Sohng, JK (2014) Efficient enzymatic systems for synthesis of novel 伪-mangostin glycosides exhibiting antibacterial activity against Gram-positive bacteria. Appl Microbiol Biotechnol 98: pp. 8527-8538 CrossRef
  24. Lee, SK, Basnet, DB, Hong, JSJ, Jung, WS, Choi, CY, Lee, HC, Sohng, JK, Ryu, KG, Kim, DJ, Ahn, JS, Kim, BS, Oh, HC, Sherman, DH, Yoon, YJ (2005) Structural diversification of macrolactones by substrate鈥恌lexible cytochrome P450 monooxygenases. Adv Synth Catal 347: pp. 1369-1378 CrossRef
  25. Menzella, HG, Reeves, CD (2007) Combinatorial biosynthesis for drug development. Curr Opin Microbiol 10: pp. 238-245 CrossRef
  26. Murray, TJ, Forsyth, CJ (2008) Total synthesis of GEX1A. Org Lett 10: pp. 3429-3431 CrossRef
  27. Pandey, RP, Parajuli, P, Koirala, N, Park, JW, Sohng, JK (2013) Probing 3-hydroxyflavone for in vitro glycorandomization of flavonols by YjiC. Appl Environ Microbiol 79: pp. 6833-6838 CrossRef
  28. Pandey, RP, Gurung, RB, Parajuli, P, Koirala, N, Tuoi, LT, Sohng, JK (2014) Assessing acceptor substrate promiscuity of YjiC-mediated glycosylation toward flavonoids. Carbohydr Res 393: pp. 26-31 CrossRef
  29. Park, SR, Park, JW, Jung, WS, Han, AR, Ban, YH, Kim, EJ, Yoon, YJ (2008) Heterologous production of epothilones B and D in Streptomyces venezuelae. Appl Microbiol Biotechnol 81: pp. 109-117 CrossRef
  30. Pellicena, M, Kr盲mer, K, Romea, P, Urpi, F (2011) Total synthesis of (+)-herboxidiene from two chiral lactate-derived ketones. Org Lett 13: pp. 5350-5353 CrossRef
  31. Piggott, AM, Karuso, P (2004) Quality, not quantity: the role of natural products and chemical proteomics in modern drug discovery. Comb Chem High Throughput Screen 7: pp. 607-630
  32. Podust, LM, Sherman, DH (2012) Diversity of P450 enzymes in the biosynthesis of natural products. Nat Prod Rep 29: pp. 1251-1266 CrossRef
  33. Premraj, R, McLeod, MD, Simpson, GW, Banwell, MG (2012) A total synthesis of herboxidiene methyl ester. Heterocycles 85: pp. 2949-2976 CrossRef
  34. Sakai, Y, Tsujita, T, Akiyama, T, Yoshida, T, Mizukami, T, Akinaga, S, Horinouchi, S, Yoshida, M, Yoshida, T (2002) GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp II. The effects on cell cycle progression and gene expression. J Antibiot (Tokyo) 55: pp. 863-872 CrossRef
  35. Salas, JA, M茅ndez, C (2009) Indolocarbazole antitumour compounds by combinatorial biosynthesis. Curr Opin Chem Biol 13: pp. 152-160 CrossRef
  36. Sanchez, C, Zhu, L, Brana, AF, Salas, AP, Rohr, J, Mendez, C, Salas, JA (2005) Combinatorial biosynthesis of antitumor indolocarbazole compounds. Proc Natl Acad Sci U S A 102: pp. 461-466 CrossRef
  37. Shao, L, Zi, J, Zeng, J, Zhan, J (2012) Identification of the herboxidiene biosynthetic gene cluster in Streptomyces chromofuscus ATCC 49982. Appl Environ Microbiol 78: pp. 2034-2038 CrossRef
  38. Simkhada, D, Lee, HC, Sohng, JK (2010) Genetic engineering approach for the production of rhamnosyl and allosyl flavonoids from Escherichia coli. Biotechnol Bioeng 107: pp. 154-162 CrossRef
  39. Singh, S, Phillips, GN, Thorson, JS (2012) The structural biology of enzymes involved in natural product glycosylation. Nat Prod Rep 29: pp. 1201-1237 CrossRef
  40. Sthapit, B, Oh, TJ, Lamichhane, R, Liou, K, Lee, HC, Kim, CG, Sohng, JK (2004) Neocarzinostatin naphthoate synthase: an unique iterative type I PKS from neocarzinostatin producer Streptomyces carzinostaticus. FEBS Lett 566: pp. 201-206 CrossRef
  41. Wideman, M, Makkar, N, Tran, M, Isaac, B, Biest, N, Stonard, R (1992) Herboxidiene, a new herbicidal substance from Streptomyces chromofuscus A7847-taxonomy, fermentation isolation, physicochemical and biological properties. J Antibiot (Tokyo) 45: pp. 914-921 CrossRef
  42. Wohlert, SE, Blanco, G, Lombo, F, Fernandez, E, Brana, AF, Reich, S, Udvarnoki, G, Mendez, C, Decker, H, Frevert, J, Salas, JA, Rohr, J (1998) Novel hybrid tetracenomycins through combinatorial biosynthesis using a glycosyltransferase encoded by the elm genes in cosmid 16聽F4 and which shows a broad sugar substrate specificity. J Am Chem Soc 120: pp. 10596-10601 CrossRef
  43. Wong, FT, Khosla, C (2012) Combinatorial biosynthesis of polyketides-a perspective. Curr Opin Chem Biol 16: pp. 117-123 CrossRef
  44. Wu, CZ, Jang, JH, Woo, M, Ahn, JS, Kim, JS, Hong, YS (2012) Enzymatic glycosylation of nonbenzoquinone geldanamycin analogs via Bacillus UDP-glycosyltransferase. Appl Environ Microbiol 78: pp. 7680-7686 CrossRef
  45. Yadav, JS, Reddy, GM, Anjum, SR, Reddy, BV (2014) A formal synthesis of herboxidiene/GEX1A. Eur J Org Chem 2014: pp. 4389-4397 CrossRef
  46. Yoon, YJ, Beck, BJ, Kim, BS, Kang, HY, Reynolds, KA, Sherman, DH (2002) Generation of multiple bioactive macrolides by hybrid modular polyketide synthases in Streptomyces venezuelae. Chem Biol 9: pp. 203-214 CrossRef
  47. Yu JM, Kishi Y, Littlefield BA (2005) Discovery of E7389, a fully synthetic macrocyclic ketone analog of halichondrin B. In: Cragg GM, Kingston DG, Newman DJ (eds.) Anticancer agents from natural products. CRC聽press, p. 329. doi:10.1201/9781420039658.ch13
  48. Yu, D, Xu, F, Zhang, S, Shao, L, Wang, S, Zhan, J (2013) Characterization of a methyltransferase involved in herboxidiene biosynthesis. Bioorg Med Chem Lett 23: pp. 5667-5670 CrossRef
  49. Yu, D, Xu, F, Shao, L, Zhan, J (2014) A specific cytochrome P450 hydroxylase in herboxidiene biosynthesis. Bioorg Med Chem Lett 24: pp. 4511-4514 CrossRef
  50. Zhang, Y, Panek, JS (2007) Total synthesis of herboxidiene/GEX 1A. Org Lett 9: pp. 3141-3143 CrossRef
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Biotechnology
  Microbiology
  Microbial Genetics and Genomics
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1432-0614

文摘

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.