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Purification, structural elucidation and bioactivity of tryptophan containing diketopiperazines, from Comamonas testosteroni associated with a rhabditid entomopathogenic nematode against major human-pathogenic bacteria.
Peptides. 2014 Mar; 53:48-58.P

Abstract

The cell free culture filtrate of a Comamonas testosteroni associated with an Entomopathogenic nematode (EPN), Rhabditis (Oscheius) sp. exhibited promising antimicrobial activity. The ethyl acetate extract of the bacterial culture filtrate was purified by silica gel column chromatography to obtain five diketopiperazines or cyclic dipeptides (DKP 1-5). The structure and absolute stereochemistry of the compounds were determined based on extensive spectroscopic analyses (HR-MS, (1)HNMR, (13)CNMR, (1)H-(1)H COSY, (1)H-(13)C HMBC) and Marfey's method. Based on the spectral data the compounds were identified as Cyclo-(L-Trp-L-Pro) (1), Cyclo-(L-Trp-L-Tyr) (2), Cyclo-(L-Trp-L-Ile) (3), Cyclo-(L-Trp-L-Leu) (4) and Cyclo-(L-Trp-L-Phe) (5), respectively. Three diketopiperazines (DKP 2, 3 and 5) were active against all the ten bacteria tested. The highest activity of 0.5μg/ml by Cyclo-(L-Trp-L-Phe) was recorded against Vibrio cholerae followed by Salmonella typhi (1 μg/ml) a human pathogen responsible for life threatening diseases like profuse watery diarrhea and typhoid or enteric fever. The activity of this compound against V. cholerae and S. typhi is more effective than ciprofloxacin and ampicillin, the standard antibiotics. Cyclo-(L-Trp-L-Phe) recorded significant antibacterial activity against all the test bacteria when compared to other compounds. Five diketopiperazines were active against all the test fungi and are more effective than bavistin the standard fungicide. Diketopiperazines recorded no cytotoxicity to FS normal fibroblast and VERO cells (African green monkey kidney) except DKP 3 and 4. To our best knowledge this is the first report of antimicrobial activity of the tryptophan containing diketopiperazines against the human pathogenic microbes. The production of cyclic dipeptides by C. testosteroni is also reported here for the first time. We conclude that the C. testosteroni is promising sources of natural bioactive secondary metabolites against human pathogenic bacteria which may receive great benefit in the field of human medicine in near future.

Authors+Show Affiliations

Division of Crop Protection, Central Tuber Crops Research Institute, Sreekariyam, Thiruvananthapuram 695017, India; Division of Crop Utilisation, Central Tuber Crops Research Institute, Sreekariyam, Thiruvananthapuram 695017, India. Electronic address: nishanthctcri@gmail.com.Division of Crop Protection, Central Tuber Crops Research Institute, Sreekariyam, Thiruvananthapuram 695017, India; Division of Crop Utilisation, Central Tuber Crops Research Institute, Sreekariyam, Thiruvananthapuram 695017, India.Division of Crop Protection, Central Tuber Crops Research Institute, Sreekariyam, Thiruvananthapuram 695017, India; Division of Crop Utilisation, Central Tuber Crops Research Institute, Sreekariyam, Thiruvananthapuram 695017, India.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24120705

Citation

Kumar, S Nishanth, et al. "Purification, Structural Elucidation and Bioactivity of Tryptophan Containing Diketopiperazines, From Comamonas Testosteroni Associated With a Rhabditid Entomopathogenic Nematode Against Major Human-pathogenic Bacteria." Peptides, vol. 53, 2014, pp. 48-58.
Kumar SN, Mohandas C, Nambisan B. Purification, structural elucidation and bioactivity of tryptophan containing diketopiperazines, from Comamonas testosteroni associated with a rhabditid entomopathogenic nematode against major human-pathogenic bacteria. Peptides. 2014;53:48-58.
Kumar, S. N., Mohandas, C., & Nambisan, B. (2014). Purification, structural elucidation and bioactivity of tryptophan containing diketopiperazines, from Comamonas testosteroni associated with a rhabditid entomopathogenic nematode against major human-pathogenic bacteria. Peptides, 53, 48-58. https://doi.org/10.1016/j.peptides.2013.09.019
Kumar SN, Mohandas C, Nambisan B. Purification, Structural Elucidation and Bioactivity of Tryptophan Containing Diketopiperazines, From Comamonas Testosteroni Associated With a Rhabditid Entomopathogenic Nematode Against Major Human-pathogenic Bacteria. Peptides. 2014;53:48-58. PubMed PMID: 24120705.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Purification, structural elucidation and bioactivity of tryptophan containing diketopiperazines, from Comamonas testosteroni associated with a rhabditid entomopathogenic nematode against major human-pathogenic bacteria. AU - Kumar,S Nishanth, AU - Mohandas,C, AU - Nambisan,Bala, Y1 - 2013/10/10/ PY - 2013/08/29/received PY - 2013/09/28/revised PY - 2013/09/30/accepted PY - 2013/10/15/entrez PY - 2013/10/15/pubmed PY - 2014/12/19/medline KW - Antibacterial KW - Comamonas testosteroni KW - Cyclic dipeptide KW - Tryptophan KW - Vibrio cholerae SP - 48 EP - 58 JF - Peptides JO - Peptides VL - 53 N2 - The cell free culture filtrate of a Comamonas testosteroni associated with an Entomopathogenic nematode (EPN), Rhabditis (Oscheius) sp. exhibited promising antimicrobial activity. The ethyl acetate extract of the bacterial culture filtrate was purified by silica gel column chromatography to obtain five diketopiperazines or cyclic dipeptides (DKP 1-5). The structure and absolute stereochemistry of the compounds were determined based on extensive spectroscopic analyses (HR-MS, (1)HNMR, (13)CNMR, (1)H-(1)H COSY, (1)H-(13)C HMBC) and Marfey's method. Based on the spectral data the compounds were identified as Cyclo-(L-Trp-L-Pro) (1), Cyclo-(L-Trp-L-Tyr) (2), Cyclo-(L-Trp-L-Ile) (3), Cyclo-(L-Trp-L-Leu) (4) and Cyclo-(L-Trp-L-Phe) (5), respectively. Three diketopiperazines (DKP 2, 3 and 5) were active against all the ten bacteria tested. The highest activity of 0.5μg/ml by Cyclo-(L-Trp-L-Phe) was recorded against Vibrio cholerae followed by Salmonella typhi (1 μg/ml) a human pathogen responsible for life threatening diseases like profuse watery diarrhea and typhoid or enteric fever. The activity of this compound against V. cholerae and S. typhi is more effective than ciprofloxacin and ampicillin, the standard antibiotics. Cyclo-(L-Trp-L-Phe) recorded significant antibacterial activity against all the test bacteria when compared to other compounds. Five diketopiperazines were active against all the test fungi and are more effective than bavistin the standard fungicide. Diketopiperazines recorded no cytotoxicity to FS normal fibroblast and VERO cells (African green monkey kidney) except DKP 3 and 4. To our best knowledge this is the first report of antimicrobial activity of the tryptophan containing diketopiperazines against the human pathogenic microbes. The production of cyclic dipeptides by C. testosteroni is also reported here for the first time. We conclude that the C. testosteroni is promising sources of natural bioactive secondary metabolites against human pathogenic bacteria which may receive great benefit in the field of human medicine in near future. SN - 1873-5169 UR - https://www.unboundmedicine.com/medline/citation/24120705/Purification_structural_elucidation_and_bioactivity_of_tryptophan_containing_diketopiperazines_from_Comamonas_testosteroni_associated_with_a_rhabditid_entomopathogenic_nematode_against_major_human_pathogenic_bacteria_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0196-9781(13)00332-X DB - PRIME DP - Unbound Medicine ER -