Skip to main content
SpringerLink
Log in

Antioxidant compounds produced by endolichenic fungus Penicillium sp.-strain 1322P isolated from Pyxine subcinerea

  • Brief Report
  • Published:
Archives of Microbiology Aims and scope Submit manuscript

Abstract

Endolichenic fungi are expecting for new bioresources of pharmacological compounds. However, the number of investigations targeting antioxidant compounds produced by endolichenic fungi remains limited. To discover new antioxidant compounds, we analyzed the antioxidant activity of the methanol extracts derived from isolated lichen mycobionts or endolichenic fungi induced from Pyxine subcinerea. We performed this analysis using the oxygen radical absorbance capacity (ORAC) method. As a result, we isolated from an endolichenic fungus identified as Penicillium sp.-stain 1322P in Pyxine subcinerea. This fungus produced a red pigment, and its chemical structure was determined to be sclerotioramine based on the analytical data obtained from NMR, LC-MS/MS, and HPLC-PDA. Sclerotioramine exhibited high antioxidant activity, and the ORAC values (mean ± SD) of sclerotioramine and sclerotiorin were 11.4 ± 0.36 and 4.86 ± 0.70 mmol TE per gram of the respective pure compound. Thus, the antioxidant activity of sclerotioramine was greater than twice that of sclerotiorin. This work represents the first report that the antioxidant activity of sclerotioramine is higher than that of the sclerotiorin.

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

Data availability

All data generated or analyzed during this study have been included in this published article.

References

  • Agrawal S, Deshmukh SK, Reddy MS, Prasad R, Goel M (2020) Endolichenic fungi: a hidden source of bioactive metabolites. S Afr J Bot 134:163–186

  • Giridharan P, Verekar SA, Khanna A, Mishra PD, Deshmukh SK (2012) Anticancer activity of sclerotiorin, isolated from an endophytic fungus Cephalotheca Faveolata Yaguchi, Nishim. & Udagawa. Indian J Exp Biol 50(7):464–468

    CAS  PubMed  Google Scholar 

  • Halliwell B, Gutteridge JMC (2015) Redox chemistry: the essentials: Free radicals in Biology and Medicine. Oxford University Press, United Kingdom, pp 30–75

    Book  Google Scholar 

  • Kawakami H, Suzuki C, Yamaguchi H et al (2019) Norlichexanthone produced by cultured endolichenic fungus induced from Pertusaria laeviganda and its antioxidant activity. Biosci Biotech Biochem 83:996–999

    Article  CAS  Google Scholar 

  • Kellogg JJ, Raja HA (2017) Endolichenic fungi: a new source of rich bioactive secondary metabolites on the horizon. Phytochem Reviews 16(2):271–293

    Article  CAS  Google Scholar 

  • Lucas EM, Castro MC, Takahashi JA (2007) Antimicrobial properties of sclerotiorin, isochromophilone VI and pencolide, metabolites from a Brazilian cerrado isolate of Penicillium Sclerotiorum Van Beyma. Brazilian J Microbiol 38:785–789

    Article  Google Scholar 

  • Minh BQ, Schmidt HA, Chernomor O, Schrempf D, Woodhams MD, Haeseler A, Lanfear R (2020) IQ-TREE 2: New models and efficient methods for phylogenetic inference in the genomic era. Mol Biol Evol 37(5):1530–1534

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Padhi S, Tayung K (2015) In vitro antimicrobial potentials of endolichenic fungi isolated from thalli of Parmelia lichen against some human pathogens. Beni-Suef Univ J Basic Appl Sci 4:299–306

    Google Scholar 

  • Rivera KG, Seifert KA (2011) A taxonomic and phylogenetic revision of the Penicillium sclerotiorum complex. Stud Mycol 70(1):139–158

  • Rozewicki J, Li S, Amada KM, Standley DM, Katoh K (2019) MAFFT-DASH: integrated protein sequence and structural alignment. Nucleic Acids Res 47(1):5–10

    Google Scholar 

  • Samanthi KAU, Wickramarachchi S, Wijeratne EMK et al (2015) Two new antioxidant active polyketides from Penicillium Citrinum, an endolichenic fungus isolated from Parmotrema species in Sri Lanka. J Natn Sci Foundation Sri Lanka 43:119–126

    Article  Google Scholar 

  • Santiago KAA, Cruz TEED, Ting ASY (2021) Diversity and bioactivity of endolichenic fungi in Usnea lichens of the Philippines. Czech Mycol 73:1–19

    Article  Google Scholar 

  • Santos PO, Ferraz CG, Ribeiro PR et al (2019) Antioxidant and antibacterial activities of the chlorine pigment sclerotiorin from Penicillium mallochii and its chemotaxonomic significance. Biochem Syst Ecol 86:103915

    Article  Google Scholar 

  • Singh BN, Upreti DK, Gupta VK et al (2017) Endolichenic fungi: a hidden reservoir of next generation biopharmaceuticals. Trends Biotech 35:808–813

    Article  CAS  Google Scholar 

  • Takenaka Y, Tanahashi T, Nagakura N, Hamada N (2000) Production of xanthones with free radical scavenging properties, emodin and sclerotiorin by the cultured lichen mycobionts of Pyrenula Japonica. Z Naturforsch C J Biosci 55(11–12):910–914

    Article  CAS  PubMed  Google Scholar 

  • Wang X, Filho JGS, Hoover AR et al (2010) Chemical epigenetics alters the secondary metabolite composition of guttate excreted by an atlantic-forest-soil-derived Penicillium citreonigrum. J Nat Prod 73:942–948

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wei MY, Wang CF, Wang KL et al (2017) Preparation, structure, and potent antifouling activity of sclerotioramine derivatives. Mar Biotech 19:372–378

    Article  CAS  Google Scholar 

  • Whalley WB (1963) The sclerotiorin group of fungal metabolites: their structure and biosynthesis. Pure Appl Chem 7:565–588

    Article  CAS  Google Scholar 

  • White PA, Oliveira RC, Oliveira AP et al (2014) Antioxidant activity and mechanisms of action of natural compounds isolated from lichens: A systematic review. Molecules 19(9):14496–14527

    Article  PubMed  PubMed Central  Google Scholar 

  • Wickramarachchi SR, Samanthi U, Wijeratne K et al (2019) A new antioxidant active compound from the endolichenic fungus, Penicillium citrinum inhabiting the lichen, Parmotrema sp. Int J Pharm Sci Res 10:3412–3420

    CAS  Google Scholar 

  • Xiao BH, She ZG, Lei XL, Chen B, Huang CH, Xu J (2011) Secondary metabolites of seaweed endophytic fungi ZJ27 in the South China Sea coast. Zhong Yao Cai 34(4):544–546

    CAS  PubMed  Google Scholar 

  • Yamamoto Y, Mizuguchi R, Yamada Y (1985) Tissue cultures of Usnea rubescens and Ramalina yasudae and production of usnic acid in their cultures. Agric Biol Chem 49:3347–3348

    CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by JSPS KAKENHI Grant Number JP19K23668. The authors report no potential conflicts of interest.

Author information

Authors and Affiliations

  1. Department of Biological Production, Akita Prefectural University, 241–438 Kaidobata-Nishi, Shimoshinjo-Nakano, Akita-shi, Akita, 010-0195, Japan

    Hiroko Kawakami, Nao Watabe, Yuko Matsubuchi, Kojiro Hara & Masashi Komine

Authors
  1. Hiroko Kawakami
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nao Watabe
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yuko Matsubuchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kojiro Hara
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Masashi Komine
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

H.K. cultured fungi, determined the chemical structure of active compounds, and descripted this report. N.W. and Y.M. isolated fungi and purified the active compounds. K.H. identified cultured fungi. M.K. provided financial support.

Corresponding author

Correspondence to Hiroko Kawakami.

Ethics declarations

Ethics approval

Not applicable.

Human and animal rights statement

The authors declare that this article does not contain any studies involving human participants or animals.

Consent to participate

Not applicable.

Consent for publication

This manuscript is original and not published elsewhere. All authors have read and approved the final manuscript, and confirm that there are no ethical issues associated with the publication of this manuscript.

Conflict of interest

We declare that we have no conflicts of interest to declare.

Additional information

Communicated by Yusuf Akhter.

Declarations.

Publisher’s Note

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

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary Material 1

Supplementary Material 2

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kawakami, H., Watabe, N., Matsubuchi, Y. et al. Antioxidant compounds produced by endolichenic fungus Penicillium sp.-strain 1322P isolated from Pyxine subcinerea. Arch Microbiol 206, 187 (2024). https://doi.org/10.1007/s00203-024-03898-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00203-024-03898-5

Keywords

Search

Navigation