Published February 28, 2023 | Version v1
Journal article Restricted

Phytotoxic meroterpenoids with herbicidal activities from the phytopathogenic fungus Pseudopestalotiopsis theae

  • 1. Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, PR China
  • 2. , Jia-Qi Liu & , Yu-Jun Yang & , Cheng-Yao Wang & , Li Zhu & , Chen-Zhe Li & , Le Cai & * , Zhong-Tao Ding & ** & Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Characteristic Plant Extraction Laboratory, Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, PR China & ** & Dali University, Dali, 671003, PR China

Description

Gan, Dong, Liu, Jia-Qi, Yang, Yu-Jun, Wang, Cheng-Yao, Zhu, Li, Li, Chen-Zhe, Cai, Le, Ding, Zhong-Tao (2023): Phytotoxic meroterpenoids with herbicidal activities from the phytopathogenic fungus Pseudopestalotiopsis theae. Phytochemistry (113522) 206: 113522, DOI: 10.1016/j.phytochem.2022.113522, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113522

Files

Restricted

The record is publicly accessible, but files are restricted to users with access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:7563C360FF815E682573FFD2B423FFA0

References

  • Akone, S.H., Wang, H., Mouelle, E.N.M., Mandi, A., Kurtan, T., Koliye, P.R., Hartmann, R., Bhatia, S., Yang, J., Muller, W.E.G., Lai, D.W., Liu, Z., Kalscheuer, R., Proksch, P., 2022. Prenylated cyclohexene-type meroterpenoids and sulfurcontaining xanthones produced by Pseudopestalotiopsis theae. Phytochemistry 197, 8. https://doi.org/10.1016/j.phytochem.2022.113124.
  • Berestetskiy, A.O., 2008. A review of fungal phytotoxins: from basic studies to practical use. Appl. Biochem. Microbiol. 44, 453-465. https://doi.org/10.1134/ s0003683808050013.
  • Bruhn, T., Schaumloffel, A., Hemberger, Y., Bringmann, G., 2013. SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25, 243-249. https://doi.org/10.1002/chir.22138.
  • Catarino, A.D., Hanada, R.E., de Queiroz, C.A., Sousa, T.F., Lima, I.N., Gasparotto, L., da Silva, G.F., 2020. First report of Pseudopestalotiopsis dawaina causing spots in caryota mitis in Brazil. Plant Dis. 104, 989. https://doi.org/10.1094/pdis-08-19-1771-pdn, 989.
  • Cimmino, A., Masi, M., Evidente, M., Superchi, S., Evidente, A., 2015. Fungal phytotoxins with potential herbicidal activity: chemical and biological characterization. Nat. Prod. Rep. 32, 1629-1653. https://doi.org/10.1039/ c5np00081e.
  • Darapanit, A., Boonyuen, N., Leesutthiphonchai, W., Nuankaew, S., Piasai, O., 2021. Identification, pathogenicity and effects of plant extracts on Neopestalotiopsis and Pseudopestalotiopsis causing fruit diseases. Sci. Rep. 11, 11. https://doi.org/10.1038/ s41598-021-02113-5.
  • Gan, D., Wang, C.Y., Li, C.Z., Zhu, L., Zhang, X.R., Ding, H., Cai, L., Ding, Z.T., 2022a. Secondary metabolites from annulohypoxylon sp. and structural revision of emericellins A and B. J. Nat. Prod. 85, 828-837. https://doi.org/10.1021/acs. jnatprod.1c00922.
  • Gan, D., Zhu, L., Zhang, X.R., Li, C.Z., Wang, C.Y., Cai, L., Ding, Z.T., 2022b. Penaloidines A and B: two unprecedented pyridine alkaloids from Penicillium sp. KYJ-6. Org. Chem. Front. 9, 2405-2411. https://doi.org/10.1039/d1qo01879e.
  • Li, F.L., Ye, Z., Huang, Z.Y., Chen, X., Sun, W.G., Gao, W.X., Zhang, S.T., Cao, F., Wang, J. P., Hu, Z.X., Zhang, Y.H., 2021a. New alpha-pyrone derivatives with herbicidal activity from the endophytic fungus Alternaria brassicicola. Bioorg. Chem. 117, 10. https://doi.org/10.1016/j.bioorg.2021.105452.
  • Li, Y.Z., Gai, Z., Wang, C.X., Li, P.L., Li, B.H., 2021b. Identification of mellein as a pathogenic substance of Botryosphaeria dothidea by UPLC-MS/MS analysis and phytotoxic bioassay. J. Agric. Food Chem. 69, 8471-8481. https://doi.org/10.1021/ acs.jafc.1c03249.
  • Liao, H.L., Chung, K.R., 2008. Genetic dissection defines the roles of elsinochrome phytotoxin for fungal pathogenesis and conidiation of the citrus pathogen Elsinoe fawcettii. Mol. Plant-Microbe Interact. 21, 469-479. https://doi.org/10.1094/mpmi-21-4-0469.
  • Maharachchikumbura, S.S.N., Guo, L.D., Liu, Z.Y., Hyde, K.D., 2016. Pseudopestalotiopsis ignota and Ps. camelliae spp. nov associated with grey blight disease of tea in China. Mycol. Prog. 15, 7. https://doi.org/10.1007/s11557-016-1162-3.
  • Masi, M., Pannacci, E., Santoro, E., Nadjia, Z., Superchi, S., Evidente, A., 2020. Stoechanones A and B, phytotoxic copaane sesquiterpenoids isolated from Lavandula stoechas with potential herbicidal activity against Amaranthus retroflexus. J. Nat. Prod. 83, 1658-1665. https://doi.org/10.1021/acs.jnatprod.0c00182.
  • Reveglia, P., Savocchia, S., Billones-Baaijens, R., Masi, M., Cimmino, A., Evidente, A., 2018. Diploquinones A and B, two new phytotoxic tetrasubstituted 1,4-naphthoquinones from Diplodia mutila, a causal agent of grapevine trunk disease. J. Agric. Food Chem. 66, 11968-11973. https://doi.org/10.1021/acs.jafc.8b05004.
  • Shahriar, S.A., Nur-Shakirah, A.O., Mohd, M.H., 2022. Neopestalotiopsis clavispora and Pseudopestalotiopsis camelliae-sinensis causing grey blight disease of tea (Camellia sinensis) in Malaysia. Eur. J. Plant Pathol. 162, 709-724. https://doi.org/10.1007/ s00425-020-03353-x.
  • Tsai, I., Maharachchikumbura, S.S.N., Hyde, K.D., Ariyawansa, H.A., 2018. Molecular phylogeny, morphology and pathogenicity of Pseudopestalotiopsis species on Ixora in Taiwan. Mycol. Prog. 17, 941-952. https://doi.org/10.1007/s11557-018-1404-7.
  • Wang, S.S., Liu, S.R., Liu, L., Li, R., Guo, R., Xia, X.B., Wei, C.L., 2020. miR477 targets the phenylalanine ammonia-lyase gene and enhances the susceptibility of the tea plant (Camellia sinensis) to disease during Pseudopestalotiopsis species infection. Planta 251, 12. https://doi.org/10.1007/s00425-020-03353-x.
  • Wang, Z.F., Sun, Z.C., Xiao, L., Zhou, Y.M., Du, F.Y., 2019. Herbicidal polyketides and diketopiperazine derivatives from Penicillium viridicatum. J. Agric. Food Chem. 67, 14102-14109. https://doi.org/10.1021/acs.jafc.9b06116.
  • Xu, J., Ji, F.F., Kang, J., Wang, H., Li, S., Jin, D.Q., Zhang, Q., Sun, H.W., Guo, Y.Q., 2015. Absolute configurations and NO inhibitory activities of terpenoids from Curcuma longa. J. Agric. Food Chem. 63, 5805-5812. https://doi.org/10.1021/acs. jafc.5b01584.
  • Yang, R., Jiang, S.L., Wen, X.D., Song, X.C., Wang, X., Li, D.X., Yin, Q.X., Wu, X., Wang, D.L., Chen, Z., 2021. Antifungal activity and possible mode of action of ningnanmycin against tea gray blight disease pathogen Pseudopestalotiopsis camelliae-sinensis. Phytopathology 111, 1735-1742. https://doi.org/10.1094/phyto-09-20- 0382-r.
  • Yu, X.Q., Muller, W.E.G., Meier, D., Kalscheuer, R., Guo, Z.Y., Zou, K., Umeokoli, B.O., Liu, Z., Proksch, P., 2020. Polyketide derivatives from mangrove derived endophytic fungus Pseudopestalotiopsis theae. Mar. Drugs 18, 15. https://doi.org/10.3390/ md18020129.
  • Zhao, D.L., Han, X.B., Wang, M., Zeng, Y.T., Li, Y.Q., Ma, G.Y., Liu, J., Zheng, C.J., Wen, M.X., Zhang, Z.F., Zhang, P., Zhang, C.S., 2020. Herbicidal and antifungal xanthone derivatives from the alga-derived fungus Aspergillus versicolor D5. J. Agric. Food Chem. 68, 11207-11214. https://doi.org/10.1021/acs.jafc.0c04265.
  • Zhao, H., Chen, G.D., Zou, J., He, R.R., Qin, S.Y., Hu, D., Li, G.Q., Guo, L.D., Yao, X.S., Gao, H., 2017. Dimericbiscognienyne A: a meroterpenoid dimer from biscogniauxia sp with new skeleton and its activity. Org. Lett. 19, 38-41. https://doi.org/10.1021/ acs.orglett.6b03264.
  • Zheng, S.Q., Chen, R.Q., Wang, Z., Liu, J., Cai, Y., Peng, M.H., Zhang, T., Li, Y.X., Wang, B.H., Bao, J.D., Zhang, D.M., Wang, Z.H., Hu, H.L., 2021. High-quality genome assembly of Pseudopestalotiopsis theae, the pathogenic fungus causing tea gray blight. Plant Dis. 105, 3723-3726. https://doi.org/10.1094/pdis-02-21-0318-a.