Cytotoxic and Antimicrobial Secondary Metabolites from Penicillium hetheringtonii IMBC-NMTP04

Tran Hong Quang, Le Ngoc Anh, Ninh Thi Ngoc, Le Thi Vien, Do Hoang Anh, Nguyen Thi Huong, Tran Thi Hong Hanh, Nguyen Xuan Cuong, Nguyen Thi Thanh Ngan, Nguyen Quang Trung, Nguyen Hoai Nam

Article Sidebar

pdf
Published Sep 7, 2023
DOI: https://doi.org/10.25073/2588-1140/vnunst.5439

Article Details

How to Cite
QUANG, Tran Hong et al. Cytotoxic and Antimicrobial Secondary Metabolites from Penicillium hetheringtonii IMBC-NMTP04. VNU Journal of Science: Natural Sciences and Technology, [S.l.], v. 39, n. 3, sep. 2023. ISSN 2588-1140. Available at: <https://js.vnu.edu.vn/NST/article/view/5439>. Date accessed: 22 dec. 2024. doi: https://doi.org/10.25073/2588-1140/vnunst.5439.
ABNT APA BibTeX CBE EndNote - EndNote format (Macintosh & Windows) MLA ProCite - RIS format (Macintosh & Windows) RefWorks Reference Manager - RIS format (Windows only) Turabian
Issue
Vol 39 No 3
Section
Original Articles

Main Article Content

Abstract

Chemical investigation of the sesame-associated fungal strain Penicillium hetheringtonii IMBC-NMTP04 resulted in isolation of five compounds, penicitrinone A (1), dihydrocitrinin (2), janthinone (3), coniochaetone B (4), and 9-oxo-10(E),12(E)-octadecadienoic acid (5). Their chemical structures were elucidated by spectroscopic methods, including 1D and 2D NMR and mass spectra in comparison with the literature data. Compound 1 showed modest cytotoxicity toward LNCaP, HepG2, MCF-7, KB, SK-Mel-2, and HL-60 human cancer cell lines, with IC50 values ranging from 60.1 to 84.2 mM while 5 was cytotoxic toward only HL-60 cell line (IC50 = 71.6 mM). All the compounds significantly inhibited E. faecalis, S. enterica, and C. albicans growth, with MIC values ranging from 12.5 to 50.0 mM. Compounds 2, 4, and 5 suppressed the growth of B. cereus, while both 1 and 2 showed antimicrobial effect against E. coli, with the same MIC value of 200 mM. This is the first time to report the chemical constituents of Penicillium hetheringtonii and the antimicrobial effect of 2–4.

Keywords: Penicillium hetheringtonii, secondary metabolites, cytotoxic; antimicrobial.

References

[1] J.A.M.P. Houbraken, J.C. Frisvad, R.A. Samson, Taxonomy of Penicillium citrinum and related species, Fungal Divers. Vol. 44, No. 1, 2010, pp. 117-133, https://doi.org/10.1007/s13225-010-0047-z.
[2] A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell, J. Mayo, M. Boyd, Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines, J. Natl. Cancer Inst. Vol. 83, No. 11, 1991, pp. 757-766, https://doi.org/10.1093/jnci/83.11.757.
[3] N.T.T. Ngan, N.H. Hoang, N.T. Hien, N.N. Lan, N.T.K. Lien, T.H. Quang, N.X. Cuong, N.H. Nam, C.V. Minh, Cytotoxic phenanthrenes and phenolic constituents from the tubers of Dioscorea persimilis, Phytochem. Lett. Vol. 40, 2020, pp. 139-143, https://doi.org/10.1016/j.phytol.2020.10.005.
[4] T.H. Quang, N.V. Phong, L.N. Anh, T.T.H. Hanh, N.X. Cuong, N.T.T. Ngan, N.Q. Trung, N.H. Nam, C.V. Minh, Secondary metabolites from a peanut-associated fungus Aspergillus niger IMBC-NMTP01 with cytotoxic, anti-inflammatory, and antimicrobial activities, Nat. Prod. Res. 2020, https://doi.org/doi.org/10.1080/14786419.2020.1868462.
[5] D. Wakana, T. Hosoe, T. Itabashi, K. Okada, G. de Campos Takaki, T. Yaguchi, K. Fukushima, K.-i. Kawai, New citrinin derivatives isolated from Penicillium citrinum, J. Nat. Med. Vol. 60, No. 4, 2006, pp. 279-284, https://doi.org/10.1007/s11418-006-0001-2.
[6] J. Deruiter, J.M. Jacyno, R.A. Davis, H.G. Cutler, Studies on aldose reductase inhibitors from fungi. I. Citrinin and related benzopyran derivatives, J. Enzyme Inhib. Vol. 6, No. 3, 1992, pp. 201-210, https://doi.org/10.3109/14756369209020170.
[7] Z. Guo, F. Cheng, K. Zou, J. Wang, Z. She, Y. Lin, Secondary metabolites from the mangrove endophytic fungus Penicillium sp. (SBE-8), Nat. Prod. Commun. Vol. 4, No. 11, 2009, pp. 1934578X0900401108, https://doi.org/10.1177/1934578X0900401108.
[8] H.-j. Wang, J.B. Gloer, J.A. Scott, D. Malloch, Coniochaetones A and B: New antifungal benzopyranones from the coprophilous fungus Coniochaeta saccardoi, Tetrahedron Lett. Vol. 36, No. 33, 1995, pp. 5847-5850, https://doi.org/10.1016/0040-4039(95)01174-G.
[9] X. Wei, C. Feng, X.-H. Li, X.-X. Mao, H.-B. Luo, D.-M. Zhang, L. Rong, Z.-Y. Xie, X. Yu, J. Li, W.-C. Ye, X.-J. Huang, C.-X. Zhang, Enantiomeric Polyketides from the Starfish-Derived Symbiotic Fungus Penicillium sp. GGF16-1-2, Chem. Biodivers. Vol. 16, No. 6, 2019, pp. e1900052, https://doi.org/10.1002/cbdv.201900052.
[10] B. Clark, R.J. Capon, E. Lacey, S. Tennant, J.H. Gill, Quinolactacins revisited: from lactams to imide and beyond, Org. Biomol. Chem. Vol. 4, No. 8, 2006, pp. 1512-1519, https://doi.org/10.1039/B600959J.
[11] M. Yoshikawa, H. Shimada, H. Matsuda, J. Yamahara, N. Murakami, Bioactive constituents of Chinese natural medicines. I. New sesquiterpene ketones with vasorelaxant effect from Chinese moxa, the processed leaves of Artemisia argyi LEVL. et VANT. : Moxartenone and moxartenolide, Chem. Pharm. Bull. Vol. 44, No. 9, 1996, pp. 1656-1662, https://doi.org/10.1248/cpb.44.1656.