Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Aug;131(2):756-767.
doi: 10.1111/jam.14995. Epub 2021 Feb 1.

Serine-glycine-betaine, a novel dipeptide from an endophyte Macrophomina phaseolina: isolation, bioactivity and biosynthesis

G Singh  1   2 , J Singh  2   3 , V Singamaneni  2   4 , S Singh  2   3 , P Gupta  2   4 , M Katoch  1   2
Affiliations

Serine-glycine-betaine, a novel dipeptide from an endophyte Macrophomina phaseolina: isolation, bioactivity and biosynthesis

G Singh et al. J Appl Microbiol. 2021 Aug.

Abstract

Aims: Endophytes are a rich source for structurally complex chemical scaffolds with interesting biological activities. Endophytes associated with Brugmansia aurea L. (family: Solanaceae), a medicinal plant, have not yet explored for the bioactive metabolites.

Method and results: Hence, Macrophomina phaseolina, a fungal endophyte, was isolated from the roots of the plant. Its methanolic extract was found active against human cancer cell lines with IC50 <20 µg ml-1 . Later, a di-peptide compound, serine-glycine-betaine, was isolated and characterized. Serine-glycine-betaine consists of a unit of an N-trimethyl glycine attached to serine. It exhibited potent activity against MIA PaCa-2 and HCT-116 cell lines with IC50 8·9 and 15·16 μmol l-1 , respectively. Furthermore, it induced apoptosis in MIA PaCa-2 cells confirmed by microscopy. The apoptotic cell death in MIA PaCa-2 cells was evidenced biochemically with the generation of intracellular reactive oxygen species level and leading to loss of mitochondrial membrane potential due to activation of the intrinsic pathway. This study describes the plausible biosynthesis of serine-glycine-betaine based on genomics (genome sequencing, annotation and genes alignment).

Conclusions: A novel di-peptide, serine-glycine-betaine isolated from M. phaseolina induced apoptosis in MIA-Pa-Ca-2 cells.

Significance and impact of the study: This study confirms that dipeptides like serine-glycine-betaine and tyrosine-betaine might be specific to fungal genera, hence being used for diagnostic purposes.

Keywords: Macrophomina phaseolina; MIA-Pa-Ca-2 cells; ROS generation; apoptosis; cytotoxicity; endophytic fungus.

PubMed Disclaimer

Similar articles

See all similar articles

Cited by

References

    1. Alvin, A., Miller, K.I. and Neilan, B.A. (2014) Exploring the potential of endophytes from medicinal plants as sources of antimycobacterial compounds. Microbiol Res 169, 483-495.
    1. Arora, D., Sharma, N., Singamaneni, V., Sharma, V., Kushwaha, M., Abrol, V., Guru, S., Sharma, S. et al. (2016) Isolation and characterization of bioactive metabolites from Xylaria psidii, an endophytic fungus of the medicinal plant Aegle marmelos and their role in mitochondrial-dependent apoptosis against pancreatic cancer cells. Phytomedicine 23, 1312-1320.
    1. Arora, N., Kumar, S., Satti, N.K., Ali, A., Gupta, P. and Katoch, M. (2018) A strain of Streptomyces sp. isolated from rhizospheric soil of Crataegus oxycantha producing nalidixic acid, a synthetic antibiotic. J Appl Microbiol 124, 1393-1400.
    1. Carollo, C.A., Calil, A.L.A., Schiave, L.A., Guaratini, T., Roberts, D.W., Lopes, N.P. and Braga, G.U. (2010) Fungal tyrosine betaine, a novel secondary metabolite from conidia of entomopathogenic Metarhizium spp. fungi. Fungal Biol 114, 473-480.
    1. Feng, X., Yu, W., Zhou, F., Chen, J. and Shen, P. (2016) A novel small molecule compound diaporine inhibits breast cancer cell proliferation via promoting ROS generation. Biomed. Pharmacother 83, 1038-1047.

MeSH terms

Supplementary concepts