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

Applied Microbiology and Biotechnology

Volumn 99, Issue 8, 2015, Pages 3421-3431

  Jha, Amit Kumar ^a   Dhakal, Dipesh ^a   Van, Pham Thi Thuy ^a   Pokhrel, Anaya Raj ^a   Yamaguchi, Tokutaro ^a   Jung, Hye Jin ^a   Yoon, Yeo Joon ^b   Sohng, Jae Kyung ^a  

^a SunMoon University   (South Korea)

^b Ewha Womans University   (South Korea)

Author keywords

Antibacterial; Epoxidation; Glycosylation; Hydroxylation; Streptomyces

Indexed keywords

BACTERIOLOGY; DRUG PRODUCTS; ELECTROSPRAY IONIZATION; EPOXIDATION; GENES; GLYCOSYLATION; HYDROXYLATION; ISOMERS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR QUADRUPOLE RESONANCE;

ANTI-BACTERIAL ACTIVITY; ANTIBACTERIAL; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE(NMR); QUADRUPOLE-TIME OF FLIGHTS; SACCHAROPOLYSPORA ERYTHRAEA; STREPTOMYCES; STRUCTURAL MODIFICATIONS;

BACTERIA;

ANTIINFECTIVE AGENT; CYTOCHROME P450; FATTY ALCOHOL; GLYCOSYLTRANSFERASE; HERBOXIDIENE; PYRAN DERIVATIVE; RECOMBINANT PROTEIN;

BACILLUS; BIOTRANSFORMATION; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; GENETICS; GROWTH, DEVELOPMENT AND AGING; METABOLIC ENGINEERING; METABOLISM; MICROCOCCUS LUTEUS; SACCHAROPOLYSPORA; STAPHYLOCOCCUS AUREUS; STREPTOMYCES;

ANTI-BACTERIAL AGENTS; BACILLUS; BIOTRANSFORMATION; CYTOCHROME P-450 ENZYME SYSTEM; FATTY ALCOHOLS; GLYCOSYLTRANSFERASES; METABOLIC ENGINEERING; MICROCOCCUS LUTEUS; PYRANS; RECOMBINANT PROTEINS; SACCHAROPOLYSPORA; STAPHYLOCOCCUS AUREUS; STREPTOMYCES;

EID: 84940006777     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-015-6431-6     Document Type: Article

References (50)

1. Banwell M, McLeod M, Premraj R, Simpson G (2000) Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847. Pure Appl Chem 72:1631–1634
2. Bierman M, Logan R, O’Brien K, Seno ET, Nagaraj R, Schoner BE (1992) Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116:43–49
3. Blakemore PR, Kocienski PJ, Morley A, Muir K (1999) A synthesis of herboxidiene. J Chem Soc Perkin Trans 1999:955–968
4. Blanchard S, Thorson JS (2006) Enzymatic tools for engineering natural product glycosylation. Curr Opin Chem Biol 10:263–271
5. Bonnal S, Vigevani L, Valcárcel J (2012) The spliceosome as a target of novel antitumour drugs. Nat Rev Drug Discov 11:847–859
6. Chaudhary AK, Dhakal D, Sohng JK (2013) An insight into the “-Omics” based engineering of streptomycetes for secondary metabolite overproduction. Biomed Res Int 2013:968518. doi:10.1155/2013/968518
7. Edmunds AJF, Trueb W, Oppolzer W, Cowley P (1997) Herboxidiene: determination of absolute configuration by degradation and synthetic studies. Tetrahedron 53:2785–2802
8. Edmunds AJ, Arnold G, Hagmann L, Schaffner R, Furlenmeier H (2000) Synthesis of simplified herboxidiene aromatic hybrids. Bioorg Med Chem Lett 10:1365–1368
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 289:1938–1947
10. Gantt RW, Peltier-Pain P, Thorson JS (2011) Enzymatic methods for glycol (diversification/randomization) of drugs and small molecules. Nat Prod Rep 28:1811–1853
11. Gao Y, Vogt A, Forsyth CJ, Koide K (2013) Comparison of splicing factor 3b inhibitors in human cells. ChemBioChem 14:49–52
12. Ghosh AK, Li J (2011) A stereoselective synthesis of (+)-herboxidiene/GEX1A. Org Lett 13:66–69
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 6:229–233
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 57:7220–7226
16. Jha AK, Lamichhane J, Sohng JK (2014) Enhancement of herboxidiene production in Streptomyces chromofuscus ATCC 49982. J Microbiol Biotechnol 24:52–58
17. Johnson AW (1999) Invitation to organic chemistry. Jones and Bartlett, Mississauga, p 169
18. Khosla C, Keasling JD (2003) Metabolic engineering for drug discovery and development. Nat Rev Drug Discov 2:1019–1025
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) 50:970–971
21. Kren V, Martinkova L (2001) Glycosides in medicine: “the role of glycosidic residue in biological activity”. Curr Med Chem 8:1303–1328
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–herboxidiene hybrid analog and related derivatives. ACS Chem Biol 9:643–648
23. Le TT, Pandey RP, Gurung RB, Dhakal D, Sohng JK (2014) Efficient enzymatic systems for synthesis of novel α-mangostin glycosides exhibiting antibacterial activity against Gram-positive bacteria. Appl Microbiol Biotechnol 98:8527–8538
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‐flexible cytochrome P450 monooxygenases. Adv Synth Catal 347:1369–1378
25. Menzella HG, Reeves CD (2007) Combinatorial biosynthesis for drug development. Curr Opin Microbiol 10:238–245
26. Murray TJ, Forsyth CJ (2008) Total synthesis of GEX1A. Org Lett 10:3429–3431
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 79:6833–6838
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 393:26–31
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 81:109–117
30. Pellicena M, Krämer K, Romea P, Urpi F (2011) Total synthesis of (+)-herboxidiene from two chiral lactate-derived ketones. Org Lett 13:5350–5353
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 7:607–630
32. Podust LM, Sherman DH (2012) Diversity of P450 enzymes in the biosynthesis of natural products. Nat Prod Rep 29:1251–1266
33. Premraj R, McLeod MD, Simpson GW, Banwell MG (2012) A total synthesis of herboxidiene methyl ester. Heterocycles 85:2949–2976
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) 55:863–872
35. Salas JA, Méndez C (2009) Indolocarbazole antitumour compounds by combinatorial biosynthesis. Curr Opin Chem Biol 13:152–160
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 102:461–466
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 78:2034–2038
38. Simkhada D, Lee HC, Sohng JK (2010) Genetic engineering approach for the production of rhamnosyl and allosyl flavonoids from Escherichia coli. Biotechnol Bioeng 107:154–162
39. Singh S, Phillips GN, Thorson JS (2012) The structural biology of enzymes involved in natural product glycosylation. Nat Prod Rep 29:1201–1237
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 566:201–206
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) 45:914–921
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 F4 and which shows a broad sugar substrate specificity. J Am Chem Soc 120:10596–10601
43. Wong FT, Khosla C (2012) Combinatorial biosynthesis of polyketides-a perspective. Curr Opin Chem Biol 16:117–123
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 78:7680–7686
45. Yadav JS, Reddy GM, Anjum SR, Reddy BV (2014) A formal synthesis of herboxidiene/GEX1A. Eur J Org Chem 2014:4389–4397
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 9:203–214
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 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 23:5667–5670
49. Yu D, Xu F, Shao L, Zhan J (2014) A specific cytochrome P450 hydroxylase in herboxidiene biosynthesis. Bioorg Med Chem Lett 24:4511–4514
50. Zhang Y, Panek JS (2007) Total synthesis of herboxidiene/GEX 1A. Org Lett 9:3141–3143