Published June 30, 2022
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Polyketides, diketopiperazines and an isochromanone from the marine-derived fungal strain Fusarium graminearum FM1010 from Hawaii
Authors/Creators
- 1. * & Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, HI, 96720, United States
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Zaman, Kh Ahammad Uz, Sarotti, Ariel M., Wu, Xiaohua, DeVine, Lela, Cao, Shugeng (2022): Polyketides, diketopiperazines and an isochromanone from the marine-derived fungal strain Fusarium graminearum FM1010 from Hawaii. Phytochemistry (113138) 198: 1-8, DOI: 10.1016/j.phytochem.2022.113138, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113138
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- urn:lsid:plazi.org:pub:FFACFF8CCA32B74FFFDCFF9756436E74
References
- Aly, A.H., Debbab, A., Proksch, P., 2011. Fungal endophytes: unique plant inhabitants with great promises. Appl. Microbiol. Biotechnol. 90, 1829-1845. https://doi.org/ 10.1007/s00253-011-3270-y.
- Chen, D., Liu, L., Lu, Y., Chen, S., 2021. Identification of fusarielin M as a novel inhibitor of Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB). Bioorg.
- Fei-Zhang, D.J., Li, C., Cao, S., 2016. Hawaii natural compounds are promising to reduce ovarian cancer deaths. Cancer Biol. Ther. 17, 709-712. https://doi.org/10.1080/ 15384047.2016.1178428.
- Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J., 2009. Gaussian 09. Gaussian, Inc., Wallingford, CT.
- Grimblat, N., Zanardi, M.M., Sarotti, A.M., 2015. Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts. J. Org. Chem. 80, 12526-12534. https://doi.org/ 10.1021/acs.joc.5b02396.
- Hallock, Y.F., Clardy, J., Kenfield, D.S., Strobel, G., 1988. De-O-methyldiaporthin, a phytotoxin from Drechslera siccans. Phytochemistry 27, 3123. https://doi.org/ 10.1016/0031-9422(88)80012-8.
- Hess, S., 2019. A universal HPLC-MS method to determine the stereochemistry of common and unusual amino acids. Amino Acid Analysis 263-275. https://doi.org/ 10.1007/978-1-61779-445-2_7.
- Huang, P., Li, C., Sarotti, A.M., Turkson, J., Cao, S., 2017. Sphaerialactonam, a γ- lactam-isochromanone from the Hawaiian endophytic fungus Paraphaeosphaeria sp. FT462. Tetrahedron Lett. 58, 1330-1333. https://doi.org/10.1016/j.
- Ichihara, A., Hashimoto, M., Hirai, T., 1989. Structure, synthesis, and stereochemistry of (+ )-Orthosporin, a phytotoxic metabolite of rhynchosporium orthosporum. Chem. Lett. 18, 1495. https://doi.org/10.1246/cl.1989.1495.
- Li, C., Ding, Y., Yang, B., Hoffman, N., Yin, H.-Q., Mahmud, T., Turkson, J., Cao, S., 2016a. Eremophilane sesquiterpenes from Hawaiian endophytic fungus Chaetoconis sp. FT087. Phytochemistry 126, 41-46. https://doi.org/10.1016/j.
- Li, C., Ding, Y., Yang, B., Miklossy, G., Yin, H., Walker, L.A., Turkson, J., Cao, S., 2015a. A new metabolite with a unique 4-pyranone γ- lactam-1,4-thiazine moiety from a Hawaiian-plant associated fungus. Org. Lett. 17, 3556-3559. https://doi.org/ 10.1021/acs.orglett.5b01650.
- Li, C., Hu, Z., Liu, Q., Wu, X., Cao, S., 2018a. Two new tricycloalternarenes from Hawaiian endophytic fungus Didymella sp. FT433. Tetrahedron Lett. 59, 3381-3383. https://doi.org/10.1016/j.tetlet.2018.07.061.
- Li, C., Ren, G., Yang, B., Miklossy, G., Turkson, J., Fei, P., Ding, Y., Walker, L.A., Cao, S., 2016b. Meroterpenoids with antiproliferative activity from a Hawaiian-plant associated fungus Peyronellaea coffeae-arabicae FT238. Org. Lett. 18, 2335-2338. https://doi.org/10.1021/acs.orglett.6b00685.
- Li, C., Sarotti, A.M., Huang, P., Dang, U.T., Hurdle, J.G., Kondratyuk, T.P., Pezzuto, J.M., Turkson, J., Cao, S., 2017a. NF-κB inhibitors, unique γ- pyranol-γ- lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462. Sci. Rep. 7, 10424. https://doi.org/ 10.1038/s41598-017-10537-1.
- Li, C., Sarotti, A.M., Turkson, J., Cao, S., 2017b. Verbenanone, an octahydro-5Hchromen-5-one from a Hawaiian-plant associated fungus FT431. Tetrahedron Lett. 58, 2290-2293. https://doi.org/10.1016/j.tetlet.2017.04.096.
- Li, C., Sarotti, A.M., Wu, X., Yang, B., Turkson, J., Chen, Y., Liu, Q., Cao, S., 2019. An unusual benzoisoquinoline-9-one derivative and other related compounds with antiproliferative activity from Hawaiian endophytic fungus Peyronellaea sp. FT431. Molecules 24. https://doi.org/10.3390/molecules24010196 pii:E196.
- Li, C., Sarotti, A.M., Yang, B., Turkson, J., Cao, S., 2017c. A new N-methoxypyridone from the Co-cultivation of Hawaiian endophytic fungi Camporesia sambuci FT1061 and epicoccum sorghinum FT1062. Molecules 22. https://doi.org/10.3390/ molecules22071166 pii:E1166.
- Li, C., Sarotti, A.M., Yoshida, W., Cao, S., 2018b. Two new polyketides from Hawaiian endophytic fungus Pestalotiopsis sp. FT172. Tetrahedron Lett. 59, 42-45. https://doi. org/10.1016/j.tetlet.2017.11.045.
- Li, C., Yang, B., Fenstemacher, R., Turkson, J., Cao, S., 2015b. Lycopodiellactone, an unusual δ- lactone-isochromanone from a Hawaiian plant-associated fungus Paraphaeosphaeria neglecta FT462. Tetrahedron Lett. 56, 1724-1727. https://doi. org/10.1016/j.tetlet.2015.02.076.
- Li, C., Yang, B., Turkson, J., Cao, S., 2017d. Anti-proliferative ambuic acid derivatives from Hawaiian endophytic fungus Pestalotiopsis sp. FT172. Phytochemistry 140, 77-82. https://doi.org/10.1016/j.phytochem.2017.04.017.
- MacroModel Schrodinger Release 2018-3, 2018. Schrodinger LLC, New York.
- Manzoni, M., Rollini, M., 2002. Biosynthesis and biotechnological production of statins by filamentous fungi and application of these cholesterol-lowering drugs. Appl. Microbiol. Biotechnol. 58, 555-564. https://doi.org/10.1007/s00253-002-0932-9.
- Marcarino, M.O., Cicetti, S., Zanardi, M.M., Sarotti, A.M., 2022. A critical review on the use of DP4+ in the structural elucidation of natural products: the good, the bad and the ugly. A practical guide. Nat. Prod. Rep. 39 (1), 58-76. https://doi.org/10.1039/ D1NP00030F.
- Pescitelli, G., Bruhn, T., 2016. Good computational practice in the assignment of absolute configurations by TDDFT calculations of ECD spectra. Chirality 28, 466-474. https://doi.org/10.1002/chir.22600.
- Song, D., Zhou, X., Peng, Q., Chen, T., Zhang, F., Huang, T., Zhang, T., Li, A., Huang, D., Wu, Q., He, H., Tang, Y., 2015. Newly emerged porcine deltacoronavirus associated with diarrhoea in swine in China: identification, prevalence and full-length genome sequence analysis. Trans. Emerg. Dis. 62 (6), 575-580. https://doi.org/10.1111/ tbed.12399.
- Sorensen, J.L., Hansen, F.T., Sondergaard, T.E., Straek, D., Lee, T.V., Wimmer, R., Klitgaard, L.G., Purup, S., Giese, H., Frandsen, R.J.N., 2012. Production of novel fusarielins by ectopic activation of the polyketide synthase 9 cluster in Fusarium graminearum. Environ. Microbiol. 14 (5), 1159-1170. https://doi.org/10.1111/ j.1462-2920.2011.02696.x.
- Tchoukoua, A., Hasegawa, R., Hendracipta, K.A., Sato, S., Koseki, T., Shiono, Y., 2018. Structure elucidation of new fusarielins from Fusarium sp. and their antimicrobial activity. Magn. Reson. Chem. 56, 32-36. https://doi.org/10.1002/mrc.4662.
- Vesonder, R.F., 1996. (all trans)-2,4,6,8,10,12-Tetradecahexene-1,14-dial, a New Pigment from Conidiobolus paulus. J. Nat. Prod. 59, 441-442. https://doi.org/ 10.1021/np9602271.
- Wang, C., Wu, X., Bai, H., Zaman, K.A., Hou, S., Saito, J., Wongwiwatthananukit, S., Kim, K.S., Cao, S., 2020. Antibacterial and NF-κB inhibitory lumazine peptides, aspochalasin, γ- butyrolactone derivatives, and cyclic peptides from a Hawaiian Aspergillus flavipes. J. Nat. Prod. 83, 2233-2240. https://doi.org/10.1021/acs. jnatprod.0c00344.
- Wang, F., Hu, Z., Li, C., Wu, X., Cao, S., 2019. Circumdatin M, a new benzodiazepine alkaloid with a unique pyrimidone-4-pyrone moiety from a Hawaiian marine fungus Aspergillus sp. FM242. Tetrahedron Lett. 60, 1724-1726. https://doi.org/10.1016/j. tetlet.2019.05.061.
- Wang, Q., Bao, L., Yang, X., Guo, H., Yang, R., Ren, B., Zhang, L., Dai, H., Guo, L., Liu, H., 2012. Polyketides with antimicrobial activity from the solid culture of an endolichenic fungus Ulocladium sp. Fitoterapia 83, 209-214. https://doi.org/ 10.1016/j.fitote.2011.10.013.
- Wei, J., Wu, B., 2020. Chemistry and bioactivities of secondary metabolites from the genus Fusarium. Fitoterapia 146, 104638. https://doi.org/10.1016/j. fitote.2020.104638.
- Wolinski, K., Hinton, J.F., Pulay, P., 1990. Efficient implementation of the gaugeindependent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 112, 8251. https://doi.org/10.1021/ja00179a005.
- Zaman, K.A., Park, J.H., Devine, L., Hu, Z., Wu, X., Kim, H.S., Cao, S., 2021a. Secondary metabolites from the leather coral-derived fungal strain xylaria sp. FM1005 and their glycoprotein IIb/IIIa inhibitory activity. J. Nat. Prod. 84 (2), 466-473. https://doi. org/10.1021/acs.jnatprod.0c01330.
- Zaman, K.A., Wu, X., Hu, Z., Cao, S., 2020a. Tryptoquivalines W and X, two new compounds from a Hawaiian fungal strain and their biological activities. Tetrahedron Lett. 61 (14), e151730 https://doi.org/10.1016/j.tetlet.2020.151730.
- Zaman, K.A., Wu, X., Hu, Z., Cao, S., 2021b. Antibacterial kaneoheoic acids AF from a Hawaiian fungus Fusarium sp. FM701. Phytochemistry 181, 112545. https://doi. org/10.1016/j.phytochem.2020.112545.
- Zaman, K.A., Wu, X., Hu, Z., Hou, S., Saito, J., Kondratyuk, T.P., Pezzuto, J.M., Cao, S., 2020b. NF-κB inhibitory and antibacterial helvolic and fumagillin derivatives from Aspergillus terreus. J. Nat. Prod. 83, 730-737. https://doi.org/10.1021/acs. jnatprod.9b01190.
- Zanardi, M.M., Marcarino, M.O., Sarotti, A.M., 2020. Redefining the impact of Boltzmann analysis in the stereochemical assignment of polar and flexible molecules by NMR calculations. Org. Lett. 22, 52-56. https://doi.org/10.1021/acs. orglett.9b03866.
- Zhou, H., Yang, X., Li, F., Yi, X., Yu, L., Gao, C., Huang, R., 2017. A new diketopiperazine of nocardiopsis alba isolated from Anthogorgia caerulea. Chem. Nat. Compd. 53, 338-340. https://link.springer.com/article/10.1007/s10600-017-1983-6.