Isolation and anti-HIV-1 integrase activity of lentzeosides A–F from extremotolerant lentzea sp. H45, a strain isolated from a high-altitude Atacama Desert soil

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The extremotolerant isolate H45 was one of several actinomycetes isolated from a high-altitude Atacama Desert soil collected in northwest Chile. The isolate was identified as a new Lentzea sp. using a combination of chemotaxonomic, morphological and phylogenetic properties. Large scale fermentation of the strain in two different media followed by chromatographic purification led to the isolation of six new diene and monoene glycosides named lentzeosides A–F, together with the known compound (Z)-3-hexenyl glucoside. The structures of the new compounds were confirmed by HRESIMS and NMR analyses. Compounds 16 displayed moderate inhibitory activity against HIV integrase.

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  1. 1

    Harvey, A. L., Edrada-Ebel, R. & Quinn, R. J. The re-emergence of natural products for drug discovery in the genomics era. Nat. Rev. Drug Discov. 14, 111–129 (2015).

  2. 2

    Pidot, S. J., Coyne, S., Kloss, F. & Hertweck, C. Antibiotics from neglected bacterial sources. Int. J. Med. Microbiol. 304, 14–22 (2014).

  3. 3

    Bull, A. T. in Extremophiles Handbook Vol. 2 (eds Horikoshi, K., Antranikian, G., Bull, A.T., Robb, F. & Stetter, K. 1203–1240 Springer-Verlag, (2011).

  4. 4

    Gómez-Silva, B., Rainey, F. A., Warren-Rhodes, K. A., McKay, C. P. & Navarro-González, R. in Microbiology of Extreme Soils, Soil Biology Vol. 13 (eds Dion, P. & Nautiyal, C. S. 117–132 Springer, Berlin, (2008).

  5. 5

    Navarro-González, R. et al. Mars-Like soils in the Atacama Desert, Chile, and the dry limit of microbial Life. Science 302, 1018–1021 (2003).

  6. 6

    Crits-Christoph, A. et al. Colonization patterns of soil microbial communities in the Atacama Desert. Microbiome 1, 28 (2013).

  7. 7

    Bull, A.T. et al. The Atacama Desert: technical resources and the growing importance of novel microbial diversity. Ann. Rev. Microbiol. 70: (2016).

  8. 8

    Okoro, C. K. et al. Diversity of culturable actinomycetes in hyper-arid soils of the Atacama Desert, Chile. Antonie van Leeuwenhoek 95, 121–133 (2009).

  9. 9

    Bull, A. T. & Asenjo, J. A. Microbiology of hyper-arid environments: recent insights from the Atacama Desert, Chile. Antonie van Leeuwenhoek 103, 1173–1179 (2013).

  10. 10

    Rateb, M. E. et al. Chaxamycins A-D, bioactive ansamycins from a hyper-arid desert Streptomyces sp. J. Nat. Prod. 74, 1491–1499 (2011).

  11. 11

    Rateb, M. E. et al. Diverse metabolic profiles of a Streptomyces strain isolated from a hyper-arid environment. J. Nat. Prod. 74, 1965–1971 (2011).

  12. 12

    Schulz, D. et al. Abenquines A–D: aminoquinone derivatives produced by Streptomyces sp. strain DB634. J. Antibiot. 64, 763–768 (2011).

  13. 13

    Nachtigall, J. et al. Atacamycins A–C, 22-membered antitumor macrolactones produced by Streptomyces sp. C38. J. Antibiot. 64, 775–780 (2011).

  14. 14

    Elsayed, S. S. et al. Chaxapeptin, a lasso peptide from extremotolerant Streptomyces leeuwenhoekii strain C58 from the hyperarid Atacama Desert. J. Org. Chem. 80, 10252–10260 (2015).

  15. 15

    Busarakam, K. et al. Streptomyces leeuwenhoekii sp. nov., the producer of chaxalactins and chaxamycins, forms a distinct branch in Streptomyces gene trees. Antonie van Leeuwenhoek 105, 849–861 (2014).

  16. 16

    Gomez-Escribano, J. P. et al. The Streptomyces leeuwenhoekii genome: de novo sequencing and assembly in single contigs of the chromosome, circular plasmid pSLE1 and linear plasmid pSLE2. BMC Genomics 16, 485 (2015).

  17. 17

    Craigie, R. HIV integrase, a brief overview from chemistry to therapeutics. J. Biol. Chem. 276, 23213–23216 (2001).

  18. 18

    Craigie, R. The road to HIV-1 integrase inhibitors: the case for supporting basic research. Future Virol. 9, 899–903 (2014).

  19. 19

    Labeda, D. P. in Bergey’s Manual of Systematic Bacteriology 2nd end, Vol. 5 (eds Goodfellow, M. et al. 1379–1383 Springer, New York, NY, USA, (2012).

  20. 20

    Cao, C.-L. et al. Lentzea guizhouensis sp. nov., a novel Lithophilous actinobacterium isolated from limestone from the Karst area, Guizhou, China. Antonie van Leeuwenhoek 108, 1365–1372 (2015).

  21. 21

    Kiuchi, F. et al. Acacia concinna Saponins. II. Structure of monoterpenoid glycosides in the alkaline hydrolysate of the saponin fraction. Chem. Pharm. Bull. 45, 807–812 (1997).

  22. 22

    Francis, J et al. Insulin Secretagogues from Moringa oleifera with cyclooxygenase enzyme and lipid peroxidation inhibitory activities. Helv. Chim. Acta 87, 317–326 (2004).

  23. 23

    Fujimoto, H. & Isomura, M. Chemical studies on chinese traditional medicine, Dangshen. I. Isolation of (Z)-3- and (E)-2-hexenyl β-D-glucosides. Biosci. Biotechnol. Biochem. 36, 2689–2690 (1988).

  24. 24

    Miyase, T. et al. Studies on the glycosides of Epimedium grandiflorum MORR. var. thunbergianum (MIQ.) NAKAI. III. Chem. Pharm. Bull. 36, 2475–2484 (1988).

  25. 25

    Yassin, A. F. et al. Lentzea gen. nov., a new genus of the order Actinomycetales. Int. J. Syst. Bacteriol. 45, 357–363 (1995).

  26. 26

    Sasamura, S. et al. Bioconversion of FR901459, a novel derivative of cyclosporin A, by Lentzea sp. 7887. J. Antibiot. 68, 511–520 (2015).

  27. 27

    Maes, M., Loyter, A. & Friedler, A. Peptides that inhibit HIV-1 integrase by blocking its protein–protein interactions. FEBS J. 279, 2795–2809 (2012).

  28. 28

    Sherman, M. P. & Greene, W. C. Slipping through the door: HIV entry into the nucleus. Microbes Infect. 4, 67–73 (2002).

  29. 29

    Hicks, C. & Gulick, R. M. Raltegravir: the first HIV type 1 integrase inhibitor. Clin. Infect. Dis. 48, 931–939 (2009).

  30. 30

    Nakanishi, T., Inada, A., Kambayashi, K. & Yoneda, K. Flavonoid glycosides of the roots of Glycyrrhiza uralensis. Phytochemistry 24, 339–341 (1985).

  31. 31

    Zakharova, O. S., Zenova, G. M. & Zvyagintsev, D. G. Some approaches to the selective isolation of actinomycetes of the Genus Actinomadura from soil. Microbiology 72, 110–113 (2003).

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We thank the College of Physical Sciences, University of Aberdeen, for provision of infrastructure and facilities in the Marine Biodiscovery Centre, and staff at the European Southern Observatory for permission and assistance in collecting soil samples from the Chajnantor plateau. ATB and JAA thank The Royal Society for support (International Joint Project Grant JP 100654). JAA thanks Conicyt for the Basal Grant FB0001 for the Centre CeBiB. HI is grateful for a scholarship from the Malaysian Government and MG for an Emeritus Fellowship from the Leverhulme Trust.

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Correspondence to Mostafa E Rateb.

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Supplementary Information accompanies the paper on The Journal of Antibiotics website

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