Published April 30, 2022
| Version v1
Journal article
Restricted
(+)- and ()-trichodermatrione A: a pair of enantiomers with a cyclobutane-containing skeleton from the endophytic fungus Trichoderma sp. EFT2
Authors/Creators
- 1. * & State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, College of Plant Protection, Nanjing Agricultural University, Nanjing & * & Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing 210095, PR China
Description
Yan, Wei, Ji, Wenxia, Ping, Chuan, Zhang, Tianyi, Li, Yu, Wang, Biao, Chen, Tianyu, He, Bo, Ye, Yonghao (2022): (+)- and ()-trichodermatrione A: a pair of enantiomers with a cyclobutane-containing skeleton from the endophytic fungus Trichoderma sp. EFT2. Phytochemistry (113087) 196: 1-5, DOI: 10.1016/j.phytochem.2022.113087, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113087
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:5D3DFF9C1D3A2045C438FF97731AB95E
References
- Barra, L., Dickschat, J.S., 2017. Harzianone biosynthesis by the biocontrol fungus Trichoderma. ChemBioChem 18, 2358-2365. https://doi.org/10.1002/ cbic.201700462.
- Gutekunst, W.R., Baran, P.S., 2011. Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation. J. Am. Chem. Soc. 133, 19076-19079. https://doi.org/10.1021/ja209205x.
- Huang, J., Gu, Y.Q., Guo, K., Zhu, L., Lan, Y., Gong, J.X., Yang, Z., 2017. Bioinspired total synthesis of homodimericin A. Angew Chem. Int. Ed. Engl. 56, 7890-7894. https:// doi.org/10.1002/ange.201702768.
- Khan, B., Zhao, S.S., Wang, Z.Y., Ye, Y.H., Ahmed Rajput, N., Yan, W., 2021. Eremophilane sesquiterpenes and benzene derivatives from the endophyte Microdiplodia sp. WGHS5. Chem. Biodivers., e2000949 https://doi.org/10.1002/ cbdv.202000949.
- Kuang, G.-K., Wang, L., Yang, L.-L., Zhang, Y.-B., Luo, D., Zhou, Y.-D., Chen, N.-H., Wu, Z.-N., Wang, G.-C., Li, Y.-L., 2020. One new sesquiterpene pyridine alkaloid from the stems and leaves of Euonymus fortunei. J. Asian Nat. Prod. Res. 23, 399-406. https://doi.org/10.1080/10286020.2020.1755272.
- Li, J., Gao, K., Bian, M., Ding, H., 2020. Recent advances in the total synthesis of cyclobutane-containing natural products. Org. Chem. Front. 7, 136-154. https://doi. org/10.1039/c9qo01178a.
- Liang, L.-F., Kurtan, T., Mandi, A., Yao, L.-G., Li, J., Zhang, W., Guo, Y.-W., 2013. Unprecedented diterpenoids as a PTP1B inhibitor from the Hainan soft coral Sarcophyton trocheliophorum Marenzeller. Org. Lett. 15, 274-277. https://doi.org/ 10.1021/ol303110d.
- Liao, H.B., Lei, C., Gao, L.X., Li, J.Y., Li, J., Hou, A.J., 2015. Two enantiomeric pairs of meroterpenoids from Rhododendron capitatum. Org. Lett. 17, 5040-5043. https:// doi.org/10.1021/acs.orglett.5b02515.
- Liu, J.Y., Song, Y.C., Zhang, Z., Wang, L., Guo, Z.J., Zou, W.X., Tan, R.X., 2004. Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites. J. Biotechnol. 114, 279-287. https://doi. org/10.1016/j.jbiotec.2004.07.008.
- Long, H.L., Cheng, Z.B., Huang, W., Wu, Q., Li, X.D., Cui, J.G., Proksch, P., Lin, W.H., 2016. Diasteltoxins A-C, asteltoxin-based dimers from a mutant of the spongeassociated Emericella variecolor Fungus. Org. Lett. 18, 4678-4681. https://doi.org/ 10.1021/acs.orglett.6b02313.
- Luque, A., Paternoga, J., Opatz, T., 2021. Strain release chemistry of photogenerated small-ring Intermediates. Chem. Eur J. 27, 4500-4516. https://doi.org/10.1002/ chem.202004178.
- Mevers, E., Sauri, J., Liu, Y.Z., Moser, A., Ramadhar, T.R., Varlan, M., Williamson, R.T., Martin, G.E., Clardy, J., 2016. Homodimericin A: a complex hexacyclic fungal metabolite. J. Am. Chem. Soc. 138, 12324-12327. https://doi.org/10.1021/ jacs.6b07588.
- Miao, F.-P., Liang, X.-R., Yin, X.-L., Wang, G., Ji, N.-Y., 2012. Absolute configurations of unique harziane diterpenes from Trichoderma Species. Org. Lett. 14, 3815-3817. https://doi.org/10.1021/ol3014717.
- Ouyang, X.L., Fang, X.M., Pan, Y.M., Wei, L.X., Wang, H.S., 2012. Development of HPLC fingerprint for the quality control of Euonymus fortunei and distinguishing it from related species. Acta Chromatogr. 24, 301-316. https://doi.org/10.1556/ AChrom.22.2010.4.10.
- Pan, X., Xu, S., Wu, J., Luo, J., Duan, Y., Wang, J., Zhang, F., Zhou, M., 2018. Screening and characterization, of Xanthomonas oryzae pv. oryzae strains with resistance to pheazine-1-carboxylic acid. Pestic. Biochem. Physiol. 145, 8-14. https://doi.org/ 10.1016/j.pestbp.2017.12.003.
- Ruider, S.A., Sandmeier, T., Carreira, E.M., 2015. Total synthesis of (+/-)-hippolachnin A. Angew Chem. Int. Ed. Engl. 54, 2378-2382. https://doi.org/10.1055/s-0036- 1591428.
- Wang, P., Wang, D.Y., Zhang, R.X., Wang, Y., Kong, F.D., Fu, P., Zhu, W.M., 2020. Novel macrolactams from a deep-sea-derived Streptomyces species. Mar. Drugs 19, 13. https://doi.org/10.3390/md19010013.
- Yan, B.C., Zhou, M., Li, J., Li, X.N., He, S.J., Zuo, J.P., Sun, H.D., Li, A., Puno, P.T., 2021. (-)-Isoscopariusin A, a naturally occurring immunosuppressive meroditerpenoid: structure elucidation and scalable chemical synthesis. Angew Chem. Int. Ed. Engl. 60, 12859-12867. https://doi.org/10.1002/ange.202100288.
- Yan, L.H., Liu, X.Q., Zhu, H., Xu, Q.R., Wang, W.M., Zhang, S.M., Zhang, Q.W., Zhang, S. S., Wang, Z.M., 2015. Chemical constituents of Euonymus fortunei. J. Asian Nat. Prod. Res. 17, 952-958. https://doi.org/10.1080/10286020.2015.1030401.
- Yan, W., Wuringege, Li, S.J., Guo, Z.K., Zhang, W.J., Wei, W., Tan, R.X., Jiao, R.H., 2017. New p -terphenyls from the endophytic fungus Aspergillus sp YXf3. Bioorg. Med. Chem. Lett 27, 51-54. https://doi.org/10.1016/j.bmcl.2016.11.033.
- Yan, W., Zhao, S.S., Gu, C.G., Tian, K.L., Wang, Z.Y., Liu, F., Ye, Y.H., 2020. Antifungal meroterpenes and dioxolanone derivatives from plant-associated endophytic fungus Phyllosticta sp. WGHL2. Fitoterapia 148, 104778. https://doi.org/10.1016/j. fitote.2020.104778.
- Zhang, S.X., Sun, F.F., Liu, L.J., Bao, L.Y., Fang, W., Yin, C.P., Zhang, Y.L., 2020. Dragonfly-associated Trichoderma harzianum QTYC77 Is not only a potential biological control agent of Fusarium oxysporum f. sp. cucumerinum but also a source of new antibacterial agents. J. Agric. Food Chem. 68, 14161-14167. https://doi.org/ 10.1021/acs.jafc.0c05760.
- Zhao, S.S., Tian, K.L., Li, Y., Ji, W.X., Liu, F., Khan, B., Yan, W., Ye, Y.H., 2020. Enantiomeric dibenzo-alpha-pyrone derivatives from Alternaria alternata ZHJG5 and their potential as agrochemicals. J. Agric. Food Chem. 68, 15115-15122. https:// doi.org/10.1021/acs.jafc.0c04106.
- Zhao, S.S., Wang, B., Tian, K.L., Ji, W.X., Zhang, T.Y., Ping, C., Yan, W., Ye, Y.H., 2021. Novel metabolites from the Cercis chinensis derived endophytic fungus Alternaria alternata ZHJG5 and their antibacterial activities. Pest Manag. Sci. 77, 2264-2271. https://doi.org/10.1002/ps.6251.
- Zhou, M., Zhang, H.B., Wang, W.G., Gong, N.B., Zhan, R., Li, X.N., Du, X., Li, L.M., Li, Y., Lu, Y., Pu, J.X., Sun, H.D., 2013. Scopariusic acid, a new meroditerpenoid with a unique cyclobutane ring isolated from Isodon scoparius. Org. Lett. 15, 4446-4449. https://doi.org/10.1021/ol401991u.