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Three bioactive cyclic dipeptides from the Bacillus sp. N strain associated with entomopathogenic nematode.
Peptides. 2014 Mar; 53:59-69.P

Abstract

In continuation of our search for new bioactive secondary metabolites from Bacillus cereus associated with entomopathogenic nematode (EPN), three cyclic dipeptides (CDPs), cyclo(L-Leu-D-Arg) (1), cyclo(2-hydroxy-Pro-L-Leu) (2), and cyclo(L-Val-L-Pro) (3) were purified from the ethyl acetate extract of B. cereus. The chemical structure of the compounds was identified by 1D, 2D NMR and HR-ESI-MS. Cyclo(L-Leu-D-Arg) recorded best antifungal activity and the highest activity was recorded against Cryptococcus neoformans (1 μg/mL), which is better than the standard antifungal agent amphotericin B. MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay was used for finding cell proliferation inhibition and cyclo(L-Leu-D-Arg) recorded significant activity against breast cancer cell line (MDAM-B231) (IC50 value: 25 μM) and the three cyclic dipeptides recorded no toxicity against normal human cell (fore skin (FS) normal fibroblast) up to 50 μM except cyclo(L-Val-L-Pro). Cyclo(L-Leu-D-Arg) induced significant morphological changes and DNA fragmentation associated with apoptosis in MDAM-B231 cells by acridine orange/ethidium bromide staining and flow cytometry analysis. Out of three cyclic dipeptides tested only cyclo(2-hydroxy-Pro-L-Leu) recorded significant antioxidant activity. The hydroxyl radical scavenging activity of cyclo(2-hydroxy-Pro-L-Leu) is greater than BHA, the standard antioxidant agent. Cyclo(L-Leu-D-Arg) was isolated for the first time from a natural source with a d-arginine residue. To the best of our knowledge, this is the first time that the bioactivity of the isolated cyclic dipeptides is reported against medically important fungi and cancer cells. This study is a significant contribution to the knowledge of cyclo(L-Leu-D-Arg) from B. cereus as potential sources of new drugs in the pharmacological industry, especially as potent antifungal and anticancer agent.

Authors+Show Affiliations

Division of Crop Protection, Central Tuber Crops Research Institute, Sreekariyam, Thiruvananthapuram 695017, India. Electronic address: micronishanth@rediffmail.com.Division of Crop Protection, Central Tuber Crops Research Institute, Sreekariyam, Thiruvananthapuram 695017, India.Department of Botany, SD College, Alappuzha, Kerala, India.

Pub Type(s)

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

Language

eng

PubMed ID

24291459

Citation

Nishanth, Sasidharan Kumar, et al. "Three Bioactive Cyclic Dipeptides From the Bacillus Sp. N Strain Associated With Entomopathogenic Nematode." Peptides, vol. 53, 2014, pp. 59-69.
Nishanth SK, Nambisan B, Dileep C. Three bioactive cyclic dipeptides from the Bacillus sp. N strain associated with entomopathogenic nematode. Peptides. 2014;53:59-69.
Nishanth, S. K., Nambisan, B., & Dileep, C. (2014). Three bioactive cyclic dipeptides from the Bacillus sp. N strain associated with entomopathogenic nematode. Peptides, 53, 59-69. https://doi.org/10.1016/j.peptides.2013.11.017
Nishanth SK, Nambisan B, Dileep C. Three Bioactive Cyclic Dipeptides From the Bacillus Sp. N Strain Associated With Entomopathogenic Nematode. Peptides. 2014;53:59-69. PubMed PMID: 24291459.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Three bioactive cyclic dipeptides from the Bacillus sp. N strain associated with entomopathogenic nematode. AU - Nishanth,Sasidharan Kumar, AU - Nambisan,Bala, AU - Dileep,C, Y1 - 2013/11/28/ PY - 2013/11/12/received PY - 2013/11/15/revised PY - 2013/11/18/accepted PY - 2013/12/3/entrez PY - 2013/12/3/pubmed PY - 2014/12/19/medline KW - Antioxidant KW - Apoptosis KW - Cryptococcus neoformans KW - Cyclo(l-Leu-d-Arg) KW - Cytotoxicity SP - 59 EP - 69 JF - Peptides JO - Peptides VL - 53 N2 - In continuation of our search for new bioactive secondary metabolites from Bacillus cereus associated with entomopathogenic nematode (EPN), three cyclic dipeptides (CDPs), cyclo(L-Leu-D-Arg) (1), cyclo(2-hydroxy-Pro-L-Leu) (2), and cyclo(L-Val-L-Pro) (3) were purified from the ethyl acetate extract of B. cereus. The chemical structure of the compounds was identified by 1D, 2D NMR and HR-ESI-MS. Cyclo(L-Leu-D-Arg) recorded best antifungal activity and the highest activity was recorded against Cryptococcus neoformans (1 μg/mL), which is better than the standard antifungal agent amphotericin B. MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay was used for finding cell proliferation inhibition and cyclo(L-Leu-D-Arg) recorded significant activity against breast cancer cell line (MDAM-B231) (IC50 value: 25 μM) and the three cyclic dipeptides recorded no toxicity against normal human cell (fore skin (FS) normal fibroblast) up to 50 μM except cyclo(L-Val-L-Pro). Cyclo(L-Leu-D-Arg) induced significant morphological changes and DNA fragmentation associated with apoptosis in MDAM-B231 cells by acridine orange/ethidium bromide staining and flow cytometry analysis. Out of three cyclic dipeptides tested only cyclo(2-hydroxy-Pro-L-Leu) recorded significant antioxidant activity. The hydroxyl radical scavenging activity of cyclo(2-hydroxy-Pro-L-Leu) is greater than BHA, the standard antioxidant agent. Cyclo(L-Leu-D-Arg) was isolated for the first time from a natural source with a d-arginine residue. To the best of our knowledge, this is the first time that the bioactivity of the isolated cyclic dipeptides is reported against medically important fungi and cancer cells. This study is a significant contribution to the knowledge of cyclo(L-Leu-D-Arg) from B. cereus as potential sources of new drugs in the pharmacological industry, especially as potent antifungal and anticancer agent. SN - 1873-5169 UR - https://www.unboundmedicine.com/medline/citation/24291459/Three_bioactive_cyclic_dipeptides_from_the_Bacillus_sp__N_strain_associated_with_entomopathogenic_nematode_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0196-9781(13)00399-9 DB - PRIME DP - Unbound Medicine ER -