Published September 30, 2022
| Version v1
Journal article
Restricted
Proposal for structural revision of several disubstituted tricycloalternarenes
Creators
Description
Fraga, Braulio M., Díaz, Carmen E. (2022): Proposal for structural revision of several disubstituted tricycloalternarenes. Phytochemistry (113289) 201: 1-10, DOI: 10.1016/j.phytochem.2022.113289, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113289
Files
Linked records
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:6F08FF8E6B13FFD4E370FD4CFF8BBB25
References
- Bai, Z.Q., Lin, X., Wang, J., Zhou, X., Liu, J., Yang, B., Yang, X., Liao, S., Wang, L., Liu, Y., 2015. New meroterpenoids from the endophytic fungus Aspergillus flavipes AIL8 derived from the mangrove plant Acanthus ilicifolius. Mar. Drugs 13, 237-248. https://doi.org/10.3390/md13010237.
- Chen, K., Zhang, X., Sun, W., Liu, J., Yang, J., Chen, C., Liu, J., Gao, L., Wang, J., Li, H., Luo, Z., Xue, Y., Zhu, H., Zhang, Y., 2017. Manginoids A-G: seven monoterpeneshikimate-conjugated meroterpenoids with a spiro ring system from Guignardia mangiferae. Org. Lett. 19, 6956-6959. https://doi.org/10.1021/acs.orglett.7b02955.
- Chen, K., Chen, C., Guo, J., Sun, W., Liu, J., Yang, J., Liu, X., Wang, J., Luo, Z., Zhu, H., Zhang, Y., 2019. Mangiterpenes A-C, four sesquiterpene/monoterpene-shikimateconjugated spirocyclic meroterpenoids from Guignardia mangiferae. Phytochemistry 164, 236-242.
- Chen, K., Chen, C., Liu, X., Sun, W., Deng, Y., Liu, J., Wang, J., Luo, Z., Zhu, H., Zhang, Y., 2021. Terpene-shikimate conjugated meroterpenoids from the endophytic fungus Guignardia mangiferae. Phytochemistry 190, 112860. https://doi.org/ 10.1016/j.phytochem.2019.05.018.
- Duan, R.T., Zhou, H., Li, H.T., Yang, Y.B., Ding, Z.T., 2016. Chemical constituents of endophytic fungus Alternaria sp. TY2-3 associated with Gastrodia elata. Nat. Prod. Res. Dev. 28, 188-191.
- Fraga, B.M., Diaz, C.E., 2022. Proposal for structural revision of several monosubstituted tricycloalternarenes. Phytochemistry 198, 113141. https://doi.org/10.1016/j. phytochem.2022.113141.
- Geris, R., Simpson, T., 2009. Meroterpenoids produced by fungi. Nat. Prod. Rep. 26, 1063-1094. https://doi.org/10.1039/B820413F.
- Guimaraes, D., Lopes, N.P., Pupo, M., 2012. Meroterpenes isolated from the endophytic fungus Guignardia mangiferae. Phytochemistry Lett 5, 519-523. https://doi.org/ 10.1016/j.phytol.2012.05.004.
- Han, W.B., Dou1, H., Yuan, W.H., Gong, W., Hou, Y.Y., Ng, S.W., Tan, R.X., 2015. Meroterpenes with toll-like receptor 3 regulating activity from the endophytic fungus Guignardia mangiferae. Planta Med. 81, 145-151. https://doi.org/10.1055/s- 0034-1383392.
- Jiang, M., Wu, Z., Liu, L., Chen, S., 2021. The chemistry and biology of fungal meroterpenoids (2009-2019). Org. Biomol. Chem. 19, 1644-1704. https://doi.org/ 10.1039/D0OB02162H.
- Kobayashi, T., Takizawa, I., Shinobe, A., Kawamoto, Y., Abe, H., Ito, H., 2019. Asymmetric synthesis and structure revision of guignardone H and I: development of a chiral 1,3-diketone possessing C2 symmetry. Org. Lett. 21, 3008-3012. https://doi. org/10.1021/acs.orglett.9b00486.
- Li, T.X., Yang, M.H., Wang, X.B., Wang, Y., Kong, L.Y., 2015. Synergistic antifungal meroterpenes and dioxolanone derivatives from the endophytic fungus Guignardia sp. J. Nat. Prod. 78, 2511-2520. https://doi.org/10.1021/acs.jnatprod.5b00008.
- Liang, F.L., Li, D.L., Chen, Y.C., Tao, M.H., Zhang, W.M., Zhang, D.Z., 2012. Secondary metabolites of endophytic Guignardia mangiferae from Smilax glabra and their antitumor activities. Chin. Tradit. Herb. Drugs 43, 856-860.
- Liebermann, B., Nussbaum, R.P., Gunther, W., Teuscher, J.M., 2001. Biosynthesis of the bicycloalternarenes, mixed terpenoids of Alternaria alternata. Phytochemistry 56, 551-557. https://doi.org/10.1016/S0031-9422(00)00459-3.
- Ma, K.L., Wei, W.J., Li, H.Y., Son, Q.Y., Dong, S.H., 2019. Meroditerpenoids with diverse ring systems and dioxolanone-type secondary metabolites from Phyllosticta capitalensis and their phytotoxic activities. Tetrahedron 75, 4611-4619. https://doi. org/10.1016/j.tet.2019.07.003.
- Masi, M., Sautua, F., Zatout, R., Castaldi, S., Arrico, L., Isticato, R., Pescitelli, G., Carmona, M.A., Evidente, A., 2021. Phaseocyclopentenones A and B, phytotoxic penta- and tetra-substituted cyclopentenones produced by Macrophomina phaseolina, the causal agent of charcoal rot of soybean in Argentina. J. Nat. Prod. 84, 459-465. https://doi.org/10.1021/acs.jnatprod.0c01287.
- Matsuda, Y., Abe, I., 2016. Biosynthesis of fungal meroterpenoids. Nat. Prod. Rep. 33, 26-53. https://doi.org/10.1039/C5NP00090D.
- Mei, W.L., Zheng, B., Zhao, Y.X., Zhong, H.M., Chen, X.L.W., Zeng, Y.B., Dong, W.H., Huang, J.L., Proksch, P., Dai, H.F., 2012. Meroterpenes from endophytic fungus A1 of mangrove plant Scyphiphora hydrophyllacea. Mar. Drugs 10, 1993-2001. https:// doi.org/10.3390/md10091993.
- Molinar, E., Rios, N., Spadafora, C., Arnold, A.E., Coley, P.D., Kursar, T.A., Gerwick, W. H., Cubilla-Rios, L., 2012. Coibanoles, a new class of meroterpenoids produced by Pycnoporus sanguineus. Tetrahedron Lett. 53, 919-922. https://doi.org/10.1016/j. tetlet.2011.12.021.
- Shen, L., Tian, S.J., Song, H.L., Chen, X., Guo, H., Wan, D., Wang, Y.R., Wang, F.W., Liu, L.J., 2018. Cytotoxic tricycloalternarene compounds from endophyte Alternaria sp. W-1 associated with Laminaria japonica. Mar. Drugs 16, 402. https://doi.org/ 10.3390/md16110402.
- Shi, X., Wei, W., Zhang, W.J., Hua, C.P., Chen, C.J., Ge, H.M., Tan, R.X., Jiao, R.H., 2015. New tricycloalternarenes from fungus Alternaria sp. J. Asian Nat. Prod. Res. 17, 143-148. https://doi.org/10.1080/10286020.2014.970536.
- Sommart, U., Rukachaisirikul, V., Trisuwan, K., Tadpetch, K., Phongpaichit, S., Preedanon, S., Sakayaroj, J., 2012. Tricycloalternarene derivatives from the endophytic fungus Guignardia bidwellii PSU-G11. Phytochemistry Lett 5, 139-143. https://doi.org/10.1016/j.phytol.2011.11.010.
- Sun, Z.H., Liang, F.L., Wu, W., Chen, Y.C., Pan, Q.L., Li, H.H., Ye, W., Liu, H.X., Li, S.N., Tan, G.H., Zhang, W.M., 2015. Guignardones P-S, new meroterpenoids from the endophytic fungus Guignardia mangiferae A348 derived from the medicinal plant Smilax glabra. Molecules 20, 22900-22907. https://doi.org/10.3390/ molecules201219890.
- Xu, Z., Xiong, B., Xu, J., 2021. Chemical investigation of secondary metabolites produced by mangrove endophytic fungus Phyllosticta capitalensis. Nat. Prod. Res. 1561-1565 https://doi.org/10.1080/14786419.2019.1656624.
- Yan, C., Liu, W., Li, J., Deng, Y., Chen, S., Liu, H., 2018. Bioactive terpenoids from Santalum album derived endophytic fungus Fusarium sp. YD-2. RSC Adv. 8, 14823-14828. https://doi.org/10.1039/C8RA02430H.
- Yan, Z., Zhao, C., Gong, J., Yang, Z., 2020. Asymmetric total synthesis of guignardones A and B. Org. Lett. 22, 1644-1647. https://doi.org/10.1021/acs.orglett.0c00241.
- Yan, W., Zhao, S., Gu, C., Tian, K., Wang, Z., Liu, F., Ye, Y., 2021. 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.
- Yang, H.G., Zhao, H., Li, J.J., Chen, S.M., Mou, L.M., Zou, J., Chen, G.D., Qin, S.Y., Wang, C.X., Hu, D., Dao, X.S., Gao, H., 2017. Phyllomeroterpenoids A-C, multibiosynthetic pathway derived meroterpenoids from the TCM endophytic fungus Phyllosticta sp. and their antimicrobial activities. Sci. Rep. 7, 12925 https://doi.org/ 10.1038/s41598-017-13407-y.
- Yuan, W.H., Liu, M., Jiang, N., Guo, Z.K., Ma, J., Zhang, J., Song, Y.C., Tan, R.X., 2010. Guignardones A-C: three meroterpenes from Guignardia mangiferae. Eur. J. Org. Chem. 6348-6353 https://doi.org/10.1002/ejoc.201000916.
- Zhang, G., Wu, G., Zhu, T., Kurtari, T., Mandi, A., Jiao, K., Li, J., Qi, X., Gu, Q., Li, D., 2013. Meroterpenoids with diverse ring system from the sponge-associated fungus Alternaria sp. JJY-32. J. Nat. Prod. 76, 1946-1957. https://doi.org/10.1021/ np4005757.
- Zhang, Y.A., Milkovits, A., Agarawal, V., Taylor, C.A., Snyder, S.A., 2021. Total synthesis of the meroterpenoid manginoid A as fueled by a challenging pinacol coupling and bicycle-forming etherification. Angew. Chem. Int. Ed. 60, 11127-11132. https://doi. org/10.1002/ange.202016178.
- Zheng, B., Zeng, Y.B., Dai, H.F., Zuo, W.J., Guo, Z.K., Yang, T., Zhong, H.M., Mei, W.L., 2012. Two new meroterpenes from endophytic fungus A1 of Scyphiphora hydrophyllacea. J. Asian Nat. Prod. Res. 14, 776-779. https://doi.org/10.1080/ 10286020.2012.693078.
- Zong, Y., Xu, Z.J., Zhu, R.X., Su, A.H., Liu, X.Y., Zhu, M.Z., Han, J.J., Zhang, J.Z., Xu, Y. L., Lou, H.X., 2021. Enantioselective total syntheses of manginoids A and C and guignardones A and C. Angew. Chem. Int. Ed. 60, 15286-15290. https://doi.org/ 10.1002/ange.202104182.