Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 35, 2021 - Issue 23
336
Views
11
CrossRef citations to date
0
Altmetric
Research Articles

Isolation of 2,5-diketopiperazines from Lysobacter capsici AZ78 with activity against Rhodococcus fascians

ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon
Pages 4969-4977 | Received 28 Feb 2020, Accepted 07 Apr 2020, Published online: 30 Apr 2020

References

  • Arunrattiyakorn P, Nitoda T, Kanzaki H. 2006. Enzymatic conversion-based method for screening cyclic dipeptide-producing microbe. Peptides. 27(4):633–639.
  • Brescia F, Marchetti-Deschmann M, Musetti R, Perazzolli M, Pertot I, Puopolo G. 2020. The rhizosphere signature on the cell motility, biofilm formation and secondary metabolite production of a plant-associated Lysobacter strain. Microbiol Res. 234:126424.
  • Bobylev MM, Bobyleva LI, Strobel GA. 1996. Synthesis and bioactivity of analogs of maculosin, a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa). J Agric Food Chem. 44(12):3960–3964.
  • Borthwick AD. 2012. 2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products. Chem Rev. 112(7):3641–3716.
  • Brauns SC, Milne P, Naude R, Van de Venter M. 2004. Selected cyclic dipeptides inhibit cancer cell growth and induce apoptosis in HT-29 colon cancer cells. Anticancer Res. 24:1713–1720.
  • Campbell J, Lin Q, Geske GD, Blackwell HE. 2009. New and unexpected insights into the modulation of LuxR-type quorum sensing by cyclic dipeptides. ACS Chem Biol. 4(12):1051–1059.
  • Cimmino A, Puopolo G, Perazzolli M, Andolfi A, Melck D, Pertot I, Evidente A. 2014. Cyclo(L-Pro-L-Tyr), the fungicide isolated from Lysobacter capsici AZ78: A Structure—Activity relationship study. Chem Heterocycl Comp. 50(2):290–295.
  • Fdhila F, Vázquez V, Sánchez JL, Riguera R. 2003. DD-diketopiperazines: antibiotics active against Vibrio anguillarum isolated from marine bacteria associated with cultures of Pecten maximus. J Nat Prod. 66(10):1299–1301.
  • Jamal Q, Cho JY, Moon JH, Kim KY. 2017. Purification and antifungal characterization of cyclo(D-Pro-L-Val) from Bacillus amyloliquefaciens Y1 against Fusarium graminearum to control head blight in wheat. Biocat Agri Biotechnol. 10:141–147.
  • Jayatilake GS, Thornton MP, Leonard AC, Grimwade JE, Baker BJ. 1996. Metabolites from an antartic sponge-associated bacterium, Pseudomonas aeruginosa. J Nat Prod. 59(3):293–296.
  • Li XJ, Gao JM, Chen H, Zhang AL, Tang M. 2012. Toxins from a symbiotic fungus, Leptographium qinlingensis associated with Dendroctonus armandi and their in vitro toxicities to Pinus armandi seedlings. Eur J Plant Pathol. 134(2):239–247.
  • Mangamuri UK, Muvva V, Poda S, Chitturi B, Yenamandra V. 2016. Bioactive natural produts from Pseudocardia endophytica VUK-10. J Genet Eng Biotechnol. 14(2):261–267.
  • Mangamuri UK, Muvva V, Poda S, Manavathi B, Bhujangarao C, Yenamandra V. 2016. Chemical characterization and bioactivity of diketopiperazine derivatives from the mangrove derived Pseudocardia endophytica. Egypt J Aquat Res. 42(2):169–175.
  • Kumar SN, Mohandas C, Siji JV, Rajasekharan KN, Nambisan B. 2012. Identification of antimicrobial compound, diketopiperazines, from a Bacillus sp. N strain associated with a rhabditid entomopathogenic nematode against major plant pathogenic fungi. J Appl Microbiol. 113(4):914–924.
  • Labrière C, Kondori N, Caous JS, Boomgaren M, Sandholm K, Ekdahl KN, Hansen JH, Svenson J. 2018. Development and evaluation of cationic amphiphilic antimicrobial 2,5-diketopiperazines. J Pept Sci. 24(7):e3090.
  • Ortiz-Castro R, Díaz-Pérez C, Martínez-Trujillo M, del Río RE, Campos-García J, López-Bucio J. 2011. Transkingdom signalling based on bacterial cyclopeptides with auxin activity in plants. P Natl Acad Sci USA. 108(17):7253–7258.
  • Panthee S, Hamamoto H, Paudel A, Sekimizu K. 2016. Lysobacter species: a potential source of novel antibiotics. Arch Microbiol. 198(9):839–845.
  • Park YC, Gunasekera SP, Lopez JV, McCarthy PJ, Wright AE. 2006. Metabolites from the marine-derived fungus Chromocleista sp. isolated from a deep-water sediment sample collected in the Gulf of Mexico. J Nat Prod. 69(4):580–584.
  • Prasad C. 2005. Food-derived neuroactive cyclic dipeptides. In Nutritional neuroscience. Boca Raton, FL: CRC Press LLC; pp. 331–340.
  • Puopolo G, Giovannini O, Pertot I. 2014. Lysobacter capsici AZ78 can be combined with copper to effectively control Plasmopara viticola on grapevine. Microbiol Res. 169(7-8):633–642.
  • Puopolo G, Cimmino A, Palmieri MC, Giovannini O, Evidente A, Pertot I. 2014. Lysobacter capsici AZ78 produces cyclo(L-Pro-L-Tyr), a 2,5-diketopiperazine with toxic activity against sporangia of Phytophthora infestans and Plasmopara viticola. J Appl Microbiol. 117(4):1168–1180.
  • Puopolo G, Tomada S, Pertot I. 2018. The impact of the omics era on the knowledge and use of Lysobacter species to control phytopathogenic micro-organisms. J Appl Microbiol. 124(1):15–27.
  • Riguera R, Fdhila F, Vazquez V, Sanchez JL. 2003. DD-Diketopiperazines: Antibiotics active against Vibrio anguillarum isolated from marine bacteria associated with cultures of Pecten maximus. J Nat Prod. 66:1299–1301.
  • Raaijmakers JM, Mazzola M. 2012. Diversity and natural functions of antibiotics produced by beneficial and plant pathogenic bacteria. Annu Rev Phytopathol. 50(1):403–424.
  • Segarra G, Puopolo G, Giovannini O, Pertot I. 2015. Stepwise flow diagram for the development of formulations of non spore-forming bacteria against foliar pathogens: the case of Lysobacter capsici AZ78. J Biotechnol. 216:56–64.
  • Stierle A, Cardellina JH, Strobel GA. 1988. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Proc Natl Acad Sci. 85(21):8008–8013.
  • Tatsuno T, Sato M, Kubota Y, Kubota Y, Tsunoda H. 1971. Toxicological investigations of metabolic substances of Fusarium nivale. Chem Pharm Bull. 19(7):1498–1500.
  • Thajudeen H, Park K, Moon S-S, Hong IS. 2010. An efficient green synthesis of proline-based cyclic dipeptides under water-mediated catalyst-freee conditions. Tetrahedron Lett. 51(9):1303–1305.
  • Wattana-Amorn P, Charoenwongsa W, Williams C, Crump MP, Apichaisataienchote B. 2016. Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria. Nat Prod Res. 30(17):1980–1983.
  • Yu F, Zaleta-Rivera K, Zhu X, Huffman J, Millet JC, Harris SD, Yuen G, Li XC, Du L. 2007. Structure and biosynthesis of heat-stable antifungal factor (HSAF), a broad-spectrum antimycotic with a novel mode of action. AAC. 51(1):64–72.
  • Zhang W, Li Y, Qian G, Wang Y, Chen H, Li YZ, Liu F, Shen Y, Du L. 2011. Identification and characterization of the anti-methicillin-resistant Staphylococcus aureus WAP-8294A2 biosynthetic gene cluster from Lysobacter enzymogenes OH11. Antimicrob Agents Chemother. 55(12):5581–5589.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.