Abstract
A new compound classified as one new azaphilone derivative, nigirpexin E (1), was obtained from the soil-derived fungus Trichoderma afroharzianum LTR-2, together with seven known compounds (2–8). The structures of 1–8 were determined by their HRESIMS, optical rotation, and NMR spectroscopic data. The absolute configuration of nigirpexin E (1) was determined on the basis of comparisons of experimental and theoretically calculated ECD spectra. Compound 3 was firstly isolated from Trichoderma. Bioactivities of the isolated compounds were assayed their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compound 1 exhibited significant inactivation effect against TMV with an inhibition rate of 67.25% (0.5 mg ml−1), which was higher than that of positive control ribavirin (56.74%). This is the first report of the anti-TMV activity of azaphilone derivatives.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 12 print issues and online access
$259.00 per year
only $21.58 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
References
Savary S, Willocquet L, Pethybridge SJ, Esker P, McRoberts N, Nelson A. The global burden of pathogens and pests on major food crops. Nat Ecol Evol. 2019;3:430–9.
Nicaise V. Crop immunity against viruses: outcomes and future challenges. Front Plant Sci. 2014;5:660.
Butler PJG. The current picture of the structure and assembly of tobacco mosaic virus. J Gen Virol. 1984;65:253–79.
Lu A, Wang TN, Hui H, Wei XY, Chui WH, Zhou CL, et al. Natural products for drug discovery: discovery of gramines as novel agents against a plant virus. J Agric Food Chem. 2019;67:2148–56.
Zhao L, Feng CH, Wu K, Chen WB, Chen YJ, Hao XG, et al. Advances and prospects in biogenic substances against plant virus: a review. Pestic Biochem Physiol. 2017;135:15–26.
Zeng ZQ, Zhuang WY. Two new species and a new Chinese record of Hypocreaceae as evidenced by morphological and molecular data. Mycobiology. 2019;47:280–91.
Li MF, Li GH, Zhang KQ. Non-volatile metabolites from Trichoderma spp. Metabolites. 2019;9:58.
Zhou QY, Yang XQ, Zhang ZX, Wang BY, Hu M, Yang YB, et al. New azaphilones and tremulane sesquiterpene from endophytic Nigrospora oryzae cocultured with Irpex lacteus. Fitoterapia. 2018;130:26–30.
Amagata T, Usami Y, Minoura K, Ito T, Numata A. Cytotoxic substances produced by a fungal strain from a sponge: physico-chemical properties and structures. J Antibiot. 1998;51:33–40.
Guo J, Ran HM, Zeng J, Liu D, Xin ZH. Tafuketide, a phylogeny-guided discovery of a new polyketide from Talaromyces funiculosus Salicorn 58. Appl Microbiol Biotechnol. 2016;100:5323–38.
Wang B, Park EM, King JB, Mattes AO, Nimmo SL, Clendinen C, et al. Transferring fungi to a deuterium-enriched medium results in assorted, conditional changes in secondary metabolite production. J Nat Prod. 2015;78:1415–21.
Chen SL, Zhang D, Chen MX, Zhang ZZ, Lian XY. A rare diketopiperazine glycoside from marine-sourced Streptomyces sp. ZZ446. Nat Prod Res. 2020;34:1046–50.
Liu C, Yang XQ, Ding ZT, Zhao LX, Cao YR, Xu LH, et al. Cyclodipeptides from the secondary metabolites of two novel actinomycetes. Chin J Nat Med. 2011;9:78–80.
Zhang Y, Zhu HL, Su LR. Phenolic acids from the roots of Salvia miltiorrhiza var. alba. J Chin Med Mater. 2017;40:854–7.
Wei N, Wang Y, Wei Q, Zhang XG, Zhang JQ, Huang Y. Chemical constituents from n-butanol fraction of Alpinia officinarum. Mod Chin Med. 2018;20:26–8.
Chen CM, Tao HM, Chen WH, Yang B, Zhou XF, Luo XW, et al. Recent advances in the chemistry and biology of azaphilones. RSC Adv. 2020;10:10197–220.
Pavesi C, Flon V, Mann S, Leleu S, Prado S, Franck X. Biosynthesis of azaphilones: a review. Nat Prod Rep. 2021;38:1058–71.
Autschbach J. Time-dependent density functional theory for calculating origin-independent optical rotation and rotatory strength tensors. Chem Phys Chem. 2011;12:3224–35.
Bruhn T, Schaumloffel A, Hemberger Y, Bringmann G. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality. 2013;25:243–9.
Frisch MJ. Gaussian 09, Revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
Gooding GV, Hebert TT. A simple technique for purification of tobacco mosaic virus in large quantities. Phytopathology. 1967;57:1285.
Yan Y, Yuan CM, Di YT, Huang T, Fan YM, Ma Y, et al. Limonoids from Munronia henryi and their anti-tobacco mosaic virus activity. Fitoterapia. 2015;107:29–35.
Acknowledgements
Young Scientists Partner Project between Shenyang Branch of Chinese Academy of Sciences and Shandong Academy of Sciences (5th) and the National Natural Science Foundation of China (41776178).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare no competing interests..
Additional information
Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
41429_2021_485_MOESM1_ESM.docx
Nigirpexin E, a new azaphilone derivative with anti-tobacco mosaic virus activity from soil-derived fungus Trichoderma afroharzianum LTR-2
Rights and permissions
About this article
Cite this article
Xie, X., Zhao, Z., Yang, H. et al. Nigirpexin E, a new azaphilone derivative with anti-tobacco mosaic virus activity from soil-derived fungus Trichoderma afroharzianum LTR-2. J Antibiot 75, 117–121 (2022). https://doi.org/10.1038/s41429-021-00485-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1038/s41429-021-00485-4
This article is cited by
-
Unveiling the biocontrol potential of Trichoderma
European Journal of Plant Pathology (2023)