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Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Review Article

Macrolactin Antibiotics: Amazing Natural Products

Author(s): Aurelio Ortiz and Estibaliz Sansinenea*

Volume 20, Issue 7, 2020

Page: [584 - 600] Pages: 17

DOI: 10.2174/1389557519666191205124050

Price: $65

Abstract

The resistance among various microbial species (infectious agents) to different antimicrobial drugs has emerged as a cause of serious public health problem all over the world. In this sense, natural products have been a rich source of compounds for drug discovery with antibiotic activity. Macrolactins are amazing structures which have antibiotic activity against some clinically relevant pathogens. In addition, they have anti-inflammatory, antifungal, antimicrobial, and antitumor activities. They are macrolides containing 24-membered lactone ring with some differences in their chemical structures. The synthesis of these compounds is a difficult task which has attracted attention of researchers; however few syntheses have been reported. In this review, the isolation of all reported macrolactins, their syntheses and biological activities are revisited.

Keywords: Macrolactins, antibiotics, natural products, microorganisms, isolation, biological activities.

Graphical Abstract
[1]
Gustafson, K.; Roman, M.; Fenical, W. The macrolactins, a novel class of antiviral and cytotoxic macrolides from a deep-sea marine bacterium. J. Am. Chem. Soc., 1989, 111, 7519-7524.
[http://dx.doi.org/10.1021/ja00201a036]
[2]
Schneider, K.; Chen, X-H.; Vater, J.; Franke, P.; Nicholson, G.; Borriss, R.; Süssmuth, R.D. Macrolactin is the polyketide biosynthesis product of the pks2 cluster of Bacillus amyloliquefaciens FZB42. J. Nat. Prod., 2007, 70(9), 1417-1423.
[http://dx.doi.org/10.1021/np070070k] [PMID: 17844999]
[3]
Seung-Je, L.; Jeong-Yong, C.; Jung-Il, C.; Jae-Hak, M.; Ki, D.P.; Young, J.L.; Keun-Hyung, P. Isolation and characterization of antimicrobial substance Macrolactin A produced from Bacillus amyloliquefaciens CHO104 isolated from soil. J. Microbiol. Biotechnol., 2004, 14, 525-531.
[4]
Jaruchoktaweechai, C.; Suwanborirux, K.; Tanasupawatt, S.; Kittakoop, P.; Menasveta, P. New macrolactins from a marine Bacillus sp. Sc026. J. Nat. Prod., 2000, 63(7), 984-986.
[http://dx.doi.org/10.1021/np990605c] [PMID: 10924180]
[5]
Nagao, T.; Adachi, K.; Sakai, M.; Nishijima, M.; Sano, H. Novel macrolactins as antibiotic lactones from a marine bacterium. J. Antibiot. (Tokyo), 2001, 54(4), 333-339.
[http://dx.doi.org/10.7164/antibiotics.54.333] [PMID: 11426657]
[6]
Yoo, J-S.; Zheng, C-J.; Lee, S.; Kwak, J-H.; Kim, W-G. Macrolactin N, a new peptide deformylase inhibitor produced by Bacillus subtilis. Bioorg. Med. Chem. Lett., 2006, 16(18), 4889-4892.
[http://dx.doi.org/10.1016/j.bmcl.2006.06.058] [PMID: 16809037]
[7]
Romero-Tabarez, M.; Jansen, R.; Sylla, M.; Lünsdorf, H.; Häussler, S.; Santosa, D.A.; Timmis, K.N.; Molinari, G. 7-O-malonyl macrolactin A, a new macrolactin antibiotic from Bacillus subtilis active against methicillin-resistant Staphylococcus aureus, vancomycin-resistant enterococci, and a small-colony variant of Burkholderia cepacia. Antimicrob. Agents Chemother., 2006, 50(5), 1701-1709.
[http://dx.doi.org/10.1128/AAC.50.5.1701-1709.2006] [PMID: 16641438]
[8]
Lu, X.L.; Xu, Q.Zh.; Shen, Y.H.; Liu, X.Y.; Jiao, B.H.; Zhang, W.D.; Ni, K.Y. Macrolactin S, a novel macrolactin antibiotic from marine Bacillus sp. Nat. Prod. Res., 2008, 22(4), 342-347.
[http://dx.doi.org/10.1080/14786410701768162] [PMID: 18322849]
[9]
Sohn, M-J.; Zheng, C-J.; Kim, W-G. Macrolactin S, a new antibacterial agent with FabG-inhibitory activity from Bacillus sp. AT28. J. Antibiot. (Tokyo), 2008, 61(11), 687-691.
[http://dx.doi.org/10.1038/ja.2008.98] [PMID: 19168985]
[10]
Zheng, C-J.; Lee, S.; Lee, C-H.; Kim, W-G. Macrolactins O.-R., glycosylated 24-membered lactones from Bacillus sp. AH159-1. J. Nat. Prod., 2007, 70(10), 1632-1635.
[http://dx.doi.org/10.1021/np0701327] [PMID: 17887720]
[11]
Mondol, M.A.; Kim, J-H.; Lee, H-S.; Lee, Y-J.; Shin, H.J. Macrolactin W, a new antibacterial macrolide from a marine Bacillus sp. Bioorg. Med. Chem. Lett., 2011, 21(12), 3832-3835.
[http://dx.doi.org/10.1016/j.bmcl.2010.12.050] [PMID: 21570834]
[12]
Chakraborty, K.; Thilakan, B.; Raola, V.K. Polyketide family of novel antibacterial 7-O-methyl-5′-hydroxy-3′-heptenoate-macrolactin from seaweed-associated Bacillus subtilis MTCC 10403. J. Agric. Food Chem., 2014, 62(50), 12194-12208.
[http://dx.doi.org/10.1021/jf504845m] [PMID: 25420039]
[13]
Li, W.; Tang, X-X.; Yan, X.; Wu, Z.; Yi, Z-W.; Fang, M-J.; Su, X.; Qiu, Y-K. A new macrolactin antibiotic from deep sea-derived bacteria Bacillus subtilis B5. Nat. Prod. Res., 2016, 30(24), 2777-2782.
[http://dx.doi.org/10.1080/14786419.2016.1155576] [PMID: 27071303]
[14]
Yan, X.; Zhou, Y-X.; Tang, X-X.; Liu, X-X.; Yi, Z-W.; Fang, M-J.; Wu, Z.; Jiang, F-Q.; Qiu, Y-K. Macrolactins from marine-derived Bacillus subtilis B5 bacteria as inhibitors of inducible nitric oxide and cytokines expression. Mar. Drugs, 2016, 14(11), 195.
[http://dx.doi.org/10.3390/md14110195] [PMID: 27792158]
[15]
Smith, A.B.; Ott, G.R. Total synthesis of (-)-Macrolactin A. J. Am. Chem. Soc., 1996, 118, 13095-13096.
[http://dx.doi.org/10.1021/ja963543a]
[16]
Kim, Y.; Singer, R.A.; Carreira, E.M. Total synthesis of macrolactin a with versatile catalytic, enantioselective dienolate aldol addition reactions. Angew. Chem. Int. Ed. Engl., 1998, 37(9), 1261-1263.
[http://dx.doi.org/10.1002/(SICI)1521-3773(19980518)37:9<1261:: AID-ANIE1261>3.0.CO;2-2] [PMID: 29711229]
[17]
Marino, J.P.; McClure, M.S.; Holub, D.P.; Comasseto, J.V.; Tucci, F.C. Stereocontrolled synthesis of (-)-macrolactin A. J. Am. Chem. Soc., 2002, 124(8), 1664-1668.
[http://dx.doi.org/10.1021/ja017177t] [PMID: 11853441]
[18]
Kobayashi, Y.; Fukuda, A.; Kimachi, T.; Ju-ichi, M.; Takemoto, Y. Asymmetric synthesis of macrolactin analogue. Tetrahedron Lett., 2004, 45, 677-680.
[http://dx.doi.org/10.1016/j.tetlet.2003.11.055]
[19]
Xiao, X.; Li, S.; Yan, X.; Liu, X.; Xu, R.; Bai, D. Synthesis of a sec-precursor and analogues of macrolactin A. Chem. Lett., 2005, 34, 906-907.
[http://dx.doi.org/10.1246/cl.2005.906]
[20]
Yadav, J.S.; Kumar, M.R.; Sabitha, G. Stereoconvergent synthesis of the C1–C11 and C12–C24 fragments of (-)-macrolactin-A. Tetrahedron Lett., 2008, 49, 463-466.
[http://dx.doi.org/10.1016/j.tetlet.2007.11.107]
[21]
Souris, C.; Misale, A.; Chen, Y.; Luparia, M.; Maulide, N. From stereodefined cyclobutenes to dienes: Total syntheses of Ieodomycin D and the southern fragment of macrolactin A. Org. Lett., 2015, 17(18), 4486-4489.
[http://dx.doi.org/10.1021/acs.orglett.5b02149] [PMID: 26349917]
[22]
Sayini, R.; Srihari, P. Studies on the total synthesis of antibiotic macrolactin S: A conventional approach for the synthesis of the C1-C9 and C10-C24 fragments. Synthesis, 2018, 50, 663-675.
[http://dx.doi.org/10.1055/s-0036-1589132]

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