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Herbicidal bio-assay of isocladosporin enantiomers and determination of its plausible absolute configuration

The Journal of Antibiotics volume 74, pages 280–284 (2021)Cite this article

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Abstract

A fungal metabolite, isocladosporin was isolated from natural fungus, Cladosporium cladosporioides in the mid of 90s. Due to the lack of optical rotation of isolated natural product sample, the absolute configuration of the natural product remained undetermined for more than two decades. Herein, we demonstrated an SAR study of enantiomers of isocladosporin in herbicidal bio-assay against wheat coleoptile. Using this study as a comparative tool we further proposed the plausible absolute configuration of natural isocladosporin for the first time. The assigned configuration was also supported through biogenetic precursors.

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References

  1. Jackyno JM, Harwood JS, Cutler HG, Lee MK. Isocladosporin, a biologically active isomer of cladosporin from Cladosporium cladosporioides. J Nat Prod. 1993;56:1397–401.

    Article  Google Scholar 

  2. Scott PM, Van Walbeek W, Maclean WM. Cladosporin, a new antifungal metabolite from Cladosporium cladosporioides. J Antibiot. 1971;24:747–55.

    Article  CAS  Google Scholar 

  3. Zheng H, Zhao C, Fang B, Jing P, Yang J, Xie X, et al. Asymmetric total synthesis of cladosporin and isocladosporin. J Org Chem. 2012;77:5656–63.

    Article  CAS  Google Scholar 

  4. Reddy BVS, Reddy PJ, Reddy SC. The stereoselective total synthesis of isocladosorpin. Tetrahedron Lett. 2013;38:5185–7.

    Article  Google Scholar 

  5. Mohapatra DK, Maity S, Banoth S, Gonnade RG, Yadav JS. Total synthesis of isocladosporin and 3-epi-isocladosporin. Tetrahedron Lett. 2016;1:53–5.

    Article  Google Scholar 

  6. Das P, Babbar P, Malhotra N, Sharma M, Jachak GR, Gonnade RG, et al. Specific stereoisomeric conformations determine the drug potency of cladosporin scaffold against malarial parasite. J Med Chem. 2018;61:5664–78.

    Article  CAS  Google Scholar 

  7. Cochrane RVK, Sanichar R, Lambkin GR, Reiz B, Xu W, Tang Y, et al. Production of new cladosporin analogues by reconstitution of the polyketide synthases responsible for the biosynthesis of this antimalarial agent. Angew Chem Int Ed. 2016;55:664–8.

    Article  CAS  Google Scholar 

  8. Wang X, Radwan MM, Taráwneh AH, Gao J, Wedge DE, Rosa LH, et al. Antifungal activity against plant pathogens of metabolites from the endophytic fungus Cladosporium cladosporioides. J Agric Food Chem. 2013;61:4551–5.

    Article  CAS  Google Scholar 

  9. Gracia BF, Torres A, Macias FA. Synergy and other interactions between polymethoxyflavones from citrus byproducts. Molecules. 2015;20:20079–106.

    Article  Google Scholar 

  10. Hancock CR, Barlow HW, Lacey HJ. The behaviour of phloridzin in the coleoptile straight-growth test. J Exp Bot. 1961;12:401–8.

    Article  CAS  Google Scholar 

  11. Nitsch JP, Nitsch C. Studies on the growth of coleoptile and first internode sections. a new, sensitive, straight-growth test for auxins. Plant Physiol. 1956;31:94–111.

    Article  CAS  Google Scholar 

  12. Macías FA, Simonet AM, Pacheco PC, Barrero AF, Cabrera E, Jiménez-González D. Natural and synthetic podolactones with potential use as natural herbicide models. J Agric Food Chem. 2000;48:3003–7.

    Article  Google Scholar 

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Acknowledgements

We thank Prof. Xeugong She for useful e-mail exchanges while we are sorting out discrepancies on optical rotation. We would like to acknowledge University Grants Commission (UGC) for providing research fellowship to PD. Besides we thank Dr. Rajesh Gonnade (Center for Material Characterization, CSIR-National Chemical Laboratory, Pune) for X-ray crystallographic analysis. DSR would like to acknowledge the SERB, New Delhi, India, for funding the project titled “Hit to Lead Development of Potent Anti-Parasitic Natural Product. Scaffolds” (EMR/2016/004301).

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Author notes

  1. D. Srinivasa Reddy

    Present address: CSIR-Indian Institute of Intigrative medicine, Canal Road, Jammu, 180001, India

Authors and Affiliations

  1. Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India

    Yash Mankad, Pronay Das & D. Srinivasa Reddy

  2. Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

    Pronay Das, Ejaj Pathan, M. V. Deshpande & D. Srinivasa Reddy

  3. Biochemical Sciences Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India

    Ejaj Pathan & M. V. Deshpande

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  1. Yash Mankad
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  2. Pronay Das
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Correspondence to M. V. Deshpande or D. Srinivasa Reddy.

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Mankad, Y., Das, P., Pathan, E. et al. Herbicidal bio-assay of isocladosporin enantiomers and determination of its plausible absolute configuration. J Antibiot 74, 280–284 (2021). https://doi.org/10.1038/s41429-020-00391-1

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