Skip to main content

Advertisement

SpringerLink
Log in

Bioactive potential evaluation and purification of compounds from an endophytic fungus Diaporthe longicolla, a resident of Saraca asoca (Roxb.) Willd.

  • Original Paper
  • Published:
Archives of Microbiology Aims and scope Submit manuscript

Abstract

An endophytic fungus (L3), isolated from the leaf tissues of Saraca asoca was identified as D. longicolla by microscopic and molecular methods. The crude extracts of D. longicolla revealed to harbor seven compounds in GC–MS analysis which was subjected to a thin layer chromatography (TLC) for purification and separation of bioactive ingredients. The partially purified fraction from TLC displayed the presence of 2-tridecene (Z) (RT-14.50), 5-tridecene (E) (RT-16.65) and 2,4-di-tert-butylphenol (RT-13.92) in GC–MS. High-performance liquid chromatography (HPLC) was performed to further purify the constituents which led to the collection of 2,4-di-tert-butyl phenol (RT-2.34) with excellent antioxidant activity and antibacterial activity against methicillin resistance Staphylococcus aureus (MRSA).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

Data availability

All data associated with the work were mentioned in the manuscript.

References

  • Agusta A, Ohashi K, Shibuya H (2006) Bisanthraquinone metabolites produced by the endophytic fungus Diaporthe sp. Chem Pharm Bull 54(4):579–582. https://doi.org/10.1248/cpb.54.579

    Article  CAS  Google Scholar 

  • Aissaoui N, Mahjoubi M, Nas F, Mghirbi O, Arab M, Souissi Y, Klouche-Khelil N (2019) Antibacterial potential of 2, 4-di-tert-butylphenol and calixarene-based prodrugs from thermophilic Bacillus licheniformis isolated in Algerian hot spring. Geomicrobiol J 36(1):53–62

    Article  CAS  Google Scholar 

  • Botella L, Diez JJ (2011) Phylogenic diversity of fungal endophytes in Spanish stands of Pinus halepensis. Fungal Divers 47(1):9–18

    Article  Google Scholar 

  • Bubák F (1905) Vierter Beitrag zur Pilzflora von Tirol. Öst. Bot Z 55:73–79

    Article  Google Scholar 

  • Bungihan ME, Tan MA, Kitajima M, Kogure N, Franzblau SG, Dela Cruz TEE, Nonato MG (2011) Bioactive metabolites of Diaporthe sp. P133, an endophytic fungus isolated from Pandanus amaryllifolius. J Nat Med 65(3–4):606–609

    Article  CAS  Google Scholar 

  • Calcul L, Waterman C, Ma WS, Lebar MD, Harter C, Mutka T, Vrijmoed L (2013) Screening mangrove endophytic fungi for antimalarial natural products. Mar Drugs 11(12):5036–5050

    Article  CAS  Google Scholar 

  • Carballira NM, Maldonado ME (1988) 6-methyl-8-hexadecenoic acid: a novel fatty acid from the marine sponge Desmapsama anchorata. Lipids 23(7):690–693

    Article  Google Scholar 

  • Chen Z, Bertin R, Froldi G (2013) EC50 estimation of antioxidant activity in DPPH assay using several statistical programs. Food Chem 138(1):414–420. https://doi.org/10.1016/j.foodchem.2012.11.001

    Article  CAS  PubMed  Google Scholar 

  • Chepkirui C, Stadler M (2017) The genus Diaporthe: a rich source of diverse and bioactive metabolites. Mycol Prog 16(5):477–494

    Article  Google Scholar 

  • Farooq S, Qayum A, Nalli Y, Lauro G, Chini MG, Bifulco G, Ali A (2020) Discovery of a secalonic acid derivative from Aspergillus aculeatus, an endophyte of Rosa damascena Mill., triggers apoptosis in MDA-MB-231 triple negative breast cancer cells. ACS Omega. https://doi.org/10.1021/acsomega.0c02505

    Article  PubMed  PubMed Central  Google Scholar 

  • Feng J, Surup F, Hauser M, Miller A, Wennrich JP, Stadler M, Kuhnert E (2020) Biosynthesis of oxygenated brasilane terpene glycosides involves a promiscuous N-acetylglucosamine transferase. Chem Comm. https://doi.org/10.1039/D0CC03950K

    Article  PubMed  Google Scholar 

  • Gomes J, Damasceno A, Carrilho C, Lobo V, Lopes H, Madede T, Lunet N (2013) Determinants of early case-fatality among stroke patients in M aputo, M ozambique and impact of in hospital complications. Int J Stroke 8:69–75

    Article  Google Scholar 

  • Kavitha A, Prabhakar P, Vijayalakshmi M, Venkateswarlu Y (2010) Purification and biological evaluation of the metabolites produced by Streptomyces sp. TK-VL_333. Res Microbiol 161(5):335–345

    Article  CAS  Google Scholar 

  • Khamthong N, Rukachaisirikul V, Phongpaichit S, Preedanon S, Sakayaroj J (2014) An antibacterial cytochalasin derivative from the marine-derived fungus Diaporthaceae sp. PSU-SP2/4. Phytochem Lett 10:5–9

    Article  CAS  Google Scholar 

  • Kharwar RN, Mishra A, Gond SK, Stierle A, Stierle D (2011) Anticancer compounds derived from fungal endophytes: their importance and future challenges. Nat Prod Rep 28(7):1208–1228. https://doi.org/10.1039/C1NP00008J

    Article  CAS  PubMed  Google Scholar 

  • Kharwar RN, Sharma VK, Mishra A, Kumar J, Singh DK, Verma SK, Kusari S (2020) Harnessing the phytotherapeutic treasure troves of the ancient medicinal plant Azadirachta indica (neem) and associated endophytic microorganisms. Planta Med 86:906–940. https://doi.org/10.1055/a-1107-9370

    Article  CAS  PubMed  Google Scholar 

  • Kusch P, Deininger S, Specht S, Maniako R, Haubrich S, Pommerening T, Kaiser A (2011) In vitro and in vivo antimalarial activity assays of seeds from Balanites aegyptiaca: compounds of the extract show growth inhibition and activity against plasmodial aminopeptidase. J Parasitol Res. https://doi.org/10.1155/2011/368692

    Article  PubMed  PubMed Central  Google Scholar 

  • Mansouri H, Yagoubi N, Ferrier D (1998) Extraction of polypropylene additives and their analysis by HPLC. Chromatographia 48(7–8):491

    Article  Google Scholar 

  • Monggoot S, Popluechai S, Gentekaki E, Pripdeevech P (2017) Fungal endophytes: an alternative source forproduction of volatile compounds from agarwood oil of Aquilaria subintegra. Microb Ecol 74(1):54–61. https://doi.org/10.1007/s00248-016-0908-4

    Article  CAS  PubMed  Google Scholar 

  • Nuthan BR, Rakshith D, Marulasiddaswamy KM, Rao HY, Ramesha KP, Mohana NC, Satish S (2020) Application of optimized and validated agar overlay TLC–bioautography assay for detecting the antimicrobial metabolites of pharmaceutical interest. J Chromatogr Sci 58(8):737–746. https://doi.org/10.1093/chromsci/bmaa045

    Article  CAS  PubMed  Google Scholar 

  • Ola AR, Debbab A, Kurtán T, Brötz-Oesterhelt H, Aly AH, Proksch P (2014) Dihydroanthracenone metabolites from the endophytic fungus Diaporthe melonis isolated from Annona squamosa. Tetrahed Lett 55(20):3147–3150. https://doi.org/10.1016/j.tetlet.2014.03.110

    Article  CAS  Google Scholar 

  • Petrini O, Fisher PJ, Petrini LE (1992) Fungal endophytes of bracken (Pteridium aquilinum) with some reflections on their use in biological control. Petrini1, PJ Fisher2 and LE PetrinP1. Sydowia 44:282–293

    Google Scholar 

  • Pourmand MR, Memariani M, Hoseini M, Yazdchi SB (2009) High prevalence of sea gene among clinical isolates of Staphylococcus aureus in Tehran. Acta Med Iran 47(5):357–361

    CAS  Google Scholar 

  • Saikarthik J, Ilango S, Vijayakumar J, Vijayaraghavan R (2017) Phytochemical nalysis of methanolic extract of seeds of Mucuna pruriens by gas chromatography mass spectrometry. Int J Pharm Sci Res 8(7):2916–2921. https://doi.org/10.13040/IJPSR.0975-8232.8(7).2916-21

    Article  CAS  Google Scholar 

  • Sharma VK, Kumar J, Singh DK, Mishra A, Verma SK, Gond SK, Kharwar RN (2017) Induction of cryptic and bioactive metabolites through natural dietary components in an endophytic fungus Colletotrichum gloeosporioides (Penz.) Sacc. Front Microbiol 8:1126. https://doi.org/10.3389/fmicb.2017.01126

    Article  PubMed  PubMed Central  Google Scholar 

  • Shen Q, Zhang B, Xu R, Wang Y, Ding X, Li P (2010) Antioxidant activity in vitro of the selenium-contained protein from the Se-enriched Bifidobacterium animalis 01. Anaerobe 16(4):380–386. https://doi.org/10.1016/j.anaerobe.2010.06.006

    Article  CAS  PubMed  Google Scholar 

  • Shpakovsky DB, Shtil AA, Kharitonashvili EV, Tyurin VY, Antonenko TA, Nazarov AA, Ott I (2018) The antioxidant 2, 6-di-tert-butylphenol moiety attenuates the pro-oxidant properties of the auranofin analogue. Metallomics 10(3):406–413. https://doi.org/10.1039/C7MT00286F

    Article  CAS  PubMed  Google Scholar 

  • Stierle A, Strobel G, Stierle D (1993) Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of Pacific yew. Sci 260(5105):214–216. https://doi.org/10.1126/science.8097061

    Article  CAS  Google Scholar 

  • Verma VC, Kharwar RN, Strobel GA (2009) Chemical and functional diversity of natural products from plant associated endophytic fungi. Nat Prod Comm 4(11):1511–1532. https://doi.org/10.1177/1934578X0900401114

    Article  CAS  Google Scholar 

  • Viszwapriya D, Prithika U, Deebika S, Balamurugan K, Pandian SK (2016) In vitro and in vivo antibiofilm potential of 2, 4-di-tert-butylphenol from seaweed surface associated bacterium Bacillus subtilis against group A streptococcus. Microbiol Res 191:19–31. https://doi.org/10.1016/j.micres.2016.05.010

    Article  CAS  PubMed  Google Scholar 

  • Wiley Registry 8th Edition with NIST 05 MS Spectra, Revision (2005) D.06.00, (2007). Agilent Technologies.

  • Yang Y, Zhang N, Xue M, Tao S (2010) Impact of soil organic matters on the distribution of polycyclic aromatic hydrocarbons (PAHs) in soils. Environ Pollut 158(6):2170–2174. https://doi.org/10.1016/j.envpol.2010.02.019

    Article  CAS  PubMed  Google Scholar 

  • Zhu J, Unelius RC, Park KC, Ochieng SA, Obrycki JJ, Baker TC (2000) Identification of (Z)-4-tridecene from defensive secretion of green lacewing Chrysoperla carnea. J Chem Ecol 26(10):2421–2434. https://doi.org/10.1023/A:1005587113469

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Authors are thankful to the Head and Coordinator, CAS and DST-FIST in Botany, Institute of Science, BHU, Varanasi, India, for providing essential research facilities. Authors (JN, AS, VSG, JK, MY), are thankful to DBT, UGC, CSIR, respectively for providing the JRFs and SRFs. RNK appreciates the SERB, DST, New Delhi, for the financial help in form of project (EEQ/2020/000549). Authors appreciably acknowledge the helps of ISLS, IOE and DST-PURSE, BHU, Varanasi, India for HPLC and GC-MS analysis and Prof. Gopal Nath, Institute of Medical Sciences, BHU, Varanasi, India for antibacterial assay facility.

Funding

JN wish to thank Department of Biotechnology (DBT) (award no.: DBT/JRF/BET-16/I/2016/AL/135), New Delhi, India for financial support. RNK appreciates the SERB, DST, New Delhi, for the financial help (EEQ/2020/000549).

Author information

Authors and Affiliations

  1. Mycopathology and Microbial Technology Laboratory, Centre of Advanced Study (CAS) in Botany, Institute of Science, Banaras Hindu University, Varanasi, 221005, India

    Jay Hind Nishad, Arti Singh, Veer Singh Gautam, Puja Kumari, Jitendra Kumar, Monika Yadav & Ravindra Nath Kharwar

Authors
  1. Jay Hind Nishad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Arti Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Veer Singh Gautam
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Puja Kumari
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jitendra Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Monika Yadav
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ravindra Nath Kharwar
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

JN, AS—conceived the research, wrote the manuscript, analyzed the data, and acquired the funding. VG, PK and JK—performed the research. MK—analyzed the data. RNK—wrote the manuscript and supervised the research.

Corresponding author

Correspondence to Ravindra Nath Kharwar.

Ethics declarations

Conflict of interest

Authors declare that they have no conflicts of interest.

Consent to participate

All authors participated in the experiment.

Consent for publication

All authors read and aware of publishing the manuscript in journal Archives of Microbiology.

Additional information

Communicated by Erko Stackebrandt.

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nishad, J.H., Singh, A., Gautam, V.S. et al. Bioactive potential evaluation and purification of compounds from an endophytic fungus Diaporthe longicolla, a resident of Saraca asoca (Roxb.) Willd.. Arch Microbiol 203, 4179–4188 (2021). https://doi.org/10.1007/s00203-021-02390-8

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00203-021-02390-8

Keywords

Search

Navigation