Abstract
To obtain new bioactive natural products, the effect of acidic stress on the metabolites of an aciduric fungus was investigated. This fungus, Penicillium sp. OUCMDZ-4736, which was isolated from the sediment around roots of mangrove (Acanthus ilicifolius), produced different compounds and higher yields under pH 2.5 than under neutral conditions. Using spectroscopic analyses and calculations, three new anthraquinone derivatives (1–3) were isolated and identified from the acidic fermentation broth (pH 2.5) of OUCMDZ-4736. Compound 1 showed much stronger anti-hepatitis B virus activity than that of the positive control, lamivudine, strongly inhibiting HBsAg and HBeAg secretion from HepG2.2.15 cells. These results show that extremophiles are a valuable resource of bioactive compounds, and that pH regulation is an effective strategy to induce metabolite production in aciduric fungi.
Similar content being viewed by others
References
Brakhage AA (2013) Regulation of fungal secondary metabolism. Nat Rev Microbiol 11:21–32
Fan YQ, Wang Y, Liu PP, Fu P, Zhu TH, Wang W, Zhu WM (2013) Indole-diterpenoids with anti-h1n1 activity from the aciduric fungus Penicillium camemberti OUCMDZ-1492. J Nat Prod 76:1328–1336
Figueroa M, Jarmusch AK, Raja HA, El-Elimat T, Kavanaugh JS, Horswill AR, Cooks RG, Cech NB, Oberlies NH (2014) Polyhydroxyanthraquinones as quorum sensing inhibitors from the guttates of Penicillium restrictum and their analysis by desorption electrospray ionization mass spectrometry. J Nat Prod 77:1351–1358
Johnson DB (1998) Biodiversity and ecology of acidophilic microorganisms. FEMS Microbiol Ecol 27:307–317
Krohn K, Kouam SF, Kuigoua GM, Hussain H, Cludius BS, Flörke U, Kurtán T, Pescitelli G, Di Bari L, Draeger S, Schulz B (2009) Xanthones and oxepino[2, 3-b]chromones from three endophytic fungi. Chemistry 15:12121–12132
Li J, Zhang YX, Chen LX, Dong ZH, Di X, Qiu F (2010) A new xanthone from Penicillium oxalicum. Chem Nat Compd 46:216–218
Lin YW, Wang LP, Wang Y, Wang W, Hao JJ, Zhu WM (2015) Bioactive natural products of Aspergillus sp. OUCMDZ-1914, an aciduric fungus from the mangrove soils. Chin J Org Chem 35:1955–1960
Qin SD, Wang Y, Wang W, Zhu WM (2016) Anti-H1N1-virus secondary metabolites from mangrove-derived aciduric fungus Penicillium sp. OUCMDZ-4736. Chin J Mar Drug 35:21–28
Redman RS, Litvintseva A, Sheehan KB, Henson JM, Rodriguez R (1999) Fungi from geothermal soils in Yellowstone National Park. Appl Environ Microbiol 65:5193–5197
Stierle AA, Stierle DB (2005) Bioprospecting in the Berkeley pit: bioactive metabolites from acid mine waste extremophiles. Stud Nat Prod Chem 32(Part L):1123–1175
Stierle AA, Stierle DB (2014) Bioactive secondary metabolites from acid mine waste extremophiles. Nat Prod Commun 9:1037–1044
Wang H, Wang Y, Wang W, Fu P, Liu PP, Zhu WM (2011) Anti-influenza virus polyketides from the acid-tolerant fungus Penicillium purpurogenum JS03-21. J Nat Prod 74:2014–2018
Wang H, Wang Y, Liu P, Wang W, Fan YQ, Zhu WM (2013) Purpurides B and C, two new sesquiterpene esters from the aciduric fungus Penicillium purpurogenum JS03-21. Chem Biodivers 10:1185–1192
Wang Y, Fan YQ, Wang YN, Zhu WM (2017) Research progress of natural products from aciduric microbes. Chin J Antibiot 42:255–260
Zettler LAA, Gómez F, Zettler E, Keenan BG, Amils R, Sogin ML (2002) Eukaryotic diversity in Spain’s River of Fire—this ancient and hostile ecosystem hosts a surprising variety of microbial organisms. Nature 417:137
Acknowledgements
This work was supported by Grants from the National Natural Science Foundation of China (nos. 81373298, U1501221 and 81561148012).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Additional information
Communicated by S. Albers.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Jin, Y., Qin, S., Gao, H. et al. An anti-HBV anthraquinone from aciduric fungus Penicillium sp. OUCMDZ-4736 under low pH stress. Extremophiles 22, 39–45 (2018). https://doi.org/10.1007/s00792-017-0975-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00792-017-0975-6