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Published March 31, 2022 | Version v1
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Sesquiterpenes with diverse skeletons from histone deacetylase inhibitor modified cultures of the basidiomycete Cyathus stercoreus (Schwein.) De Toni HFG134

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Liu, Shui-Lin, Zhou, Lin, Chen, He-Ping, Liu, Ji-Kai (2022): Sesquiterpenes with diverse skeletons from histone deacetylase inhibitor modified cultures of the basidiomycete Cyathus stercoreus (Schwein.) De Toni HFG134. Phytochemistry (113048) 195: 1-9, DOI: 10.1016/j.phytochem.2021.113048, URL: http://dx.doi.org/10.1016/j.phytochem.2021.113048

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urn:lsid:plazi.org:pub:DD6FDC063E7C354A236BFFB7AF27FFB2

Cites
Publication: 10.1139/v81-310 (DOI)
Publication: 10.1002/chir.22138 (DOI)
Publication: 10.14480/JM.2016.14.4.142 (DOI)
Publication: 10.1007/s13659-020-00239-z (DOI)
Publication: 10.1007/978-3-319-59542-9_1 (DOI)
Publication: 10.1016/j.phytol.2018.07.006 (DOI)
Publication: 10.1007/s13659-020-00288-4 (DOI)
Publication: 10.1002/anie.202000710 (DOI)
Publication: 10.1039/C0NP00006J (DOI)
Publication: 10.1016/j.phytochem.2020.112647 (DOI)
Publication: 10.1016/j.bioorg.2019.103503 (DOI)
Publication: 10.1038/s41467-021-24133-5 (DOI)
Publication: 10.3389/fphar.2020.00537 (DOI)
Publication: 10.1038/s41559-017-0347-8 (DOI)
Publication: 10.1016/j.phytochem.2020.112580 (DOI)
Publication: 10.1016/j.phytochem.2019.02.017 (DOI)
Publication: 10.1021/acs (DOI)
Publication: 10.1021/acs.jnatprod.7b00845 (DOI)
Publication: 10.1016/j (DOI)
Publication: 10.1021/acs.jnatprod.9b01177 (DOI)
Publication: 10.1515/znc-2006-9-1009 (DOI)
Publication: 10.1038/sj (DOI)
Publication: 10.1002/anie.201510928 (DOI)
Publication: 10.1016/j.fitote.2019.02.013 (DOI)
Publication: 10.1021/np068006a (DOI)
Publication: 10.1016/j.phytochem.2020.112625 (DOI)
Publication: 10.1002/anie.201208182 (DOI)
Publication: 10.1016/j.phytochem.2017.12.015 (DOI)
Publication: 10.1021/ol8024549 (DOI)
Publication: 10.1039/C004593D (DOI)
Publication: 10.1002/anie.201106502 (DOI)
Has part
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Figure: 10.5281/zenodo.8234784 (DOI)
Figure: 10.5281/zenodo.8234786 (DOI)
Figure: 10.5281/zenodo.8234788 (DOI)

References

  • Ayer, W.A., McCaskill, R.H., 1981. The cybrodins, a new class of sesquiterpenes. Can. J. Chem. 59, 2150-2158. https://doi.org/10.1139/v81-310.
  • Bruhn, T., A, S., Y, H., G, P., 2017. SpecDis Version 1.71. Berlin, Germany, 2017. https ://specdis-software.jimdo.com.
  • Bruhn, T., Schauml¨offel, 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.
  • Chang, S.-T., 2006. The world mushroom industry: trends and technological development. Int. J. Med. Mushrooms 8, 297-314. https://doi.org/10.14480/ JM.2016.14.4.142.
  • Chen, H.-P., Ji, X., Li, Z.-H., Feng, T., Liu, J.-K., 2020. Irlactane and tremulane sesquiterpenes from the cultures of the medicinal fungus Irpex lacteus HFG1102. Nat. Prod. Bioprospect. 10, 89-100. https://doi.org/10.1007/s13659-020-00239-z.
  • Chen, H.-P., Liu, J.-K., 2017. Secondary metabolites from higher fungi. In: Kinghorn, A. D., Falk, H., Gibbons, S., Kobayashi, J.i. (Eds.), Prog. Chem. Org. Nat. Prod. 106. Springer International Publishing, Cham, pp. 1-201. https://doi.org/10.1007/978- 3-319-59542-9_1.
  • Chen, L., Yao, J.-N., Chen, H.-P., Zhao, Z.-Z., Li, Z.-H., Feng, T., Liu, J.-K., 2018. Hericinoids A-C, cyathane diterpenoids from culture of mushroom Hericium erinaceus. Phytochem. Lett. 27, 94-100. https://doi.org/10.1016/j. phytol.2018.07.006.
  • Chen, M., Cao, J.-Q., Wang, W.-J., Li, N.-P., Wu, Y., Wang, L., Ye, W.-C., 2021. Four new phloroglucinol-terpene adducts from the leaves of Myrciaria cauliflora. Nat. Prod. Bioprospect. 11, 111-118. https://doi.org/10.1007/s13659-020-00288-4.
  • Feng, K.-N., Yang, Y.-L., Xu, Y.-X., Zhang, Y., Feng, T., Huang, S.-X., Liu, J.-K., Zeng, Y., 2020. A hydrolase-catalyzed cyclization forms the fused bicyclic β- lactone in vibralactone. Angew. Chem. Int. Ed. 59, 7209-7213. https://doi.org/10.1002/ anie.202000710.
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., Nakatsuji, H., Li, X., Caricato, M., Marenich, A.V., Bloino, J., Janesko, B.G., Gomperts, R., Mennucci, B., Hratchian, H. P., Ortiz, J.V., Izmaylov, A.F., Sonnenberg, J.L., Williams-Young, D., Ding, F., Lipparini, F., Egidi, F., Goings, J., Peng, B., Petrone, A., Henderson, T., Ranasinghe, D., Zakrzewski, V.G., Gao, J., Rega, N., Zheng, G., Liang, W., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Throssell, K., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M.J., Heyd, J.J., Brothers, E.N., Kudin, K.N., Staroverov, V.N., Keith, T.A., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A.P., Burant, J. C., Iyengar, S.S., Tomasi, J., Cossi, M., Millam, J.M., Klene, M., Adamo, C., Cammi, R., Ochterski, J.W., Martin, R.L., Morokuma, K., Farkas, O., Foresman, J.B., Fox, D.J., 2016. Gaussian 16, Revision C.01. Gaussian, Inc., Wallingford CT.
  • Jiang, M.-Y., Feng, T., Liu, J.-K., 2011. N-Containing compounds of macromycetes. Nat. Prod. Rep. 28, 783-808. https://doi.org/10.1039/C0NP00006J.
  • Kou, R.-W., Han, R., Gao, Y.-Q., Li, D., Yin, X., Gao, J.-M., 2021. Anti-neuroinflammatory polyoxygenated lanostanoids from Chaga mushroom Inonotus obliquus. Phytochemistry 184, 112647. https://doi.org/10.1016/j.phytochem.2020.112647.
  • Li, H.-T., Tang, L.-H., Liu, T., Yang, R.-N., Yang, Y.-B., Zhou, H., Ding, Z.-T., 2020. Protoilludane-type sesquiterpenoids from Armillaria sp. by co-culture with the endophytic fungus Epicoccum sp. associated with Gastrodia elata. Bioorg. Chem. 95, 103503. https://doi.org/10.1016/j.bioorg.2019.103503.
  • Scherlach, K., Hertweck, C., 2021. Mining and unearthing hidden biosynthetic potential. Nat. Commun. 12, 3864. https://doi.org/10.1038/s41467-021-24133-5.
  • Shukla, S., Tekwani, B.L., 2020. Histone deacetylases inhibitors in neurodegenerative diseases, neuroprotection and neuronal differentiation. Front. Pharmacol. 11, 537. https://doi.org/10.3389/fphar.2020.00537.
  • Sipos, G., Prasanna, A.N., Walter, M.C., O' Connor, E., B´alint, B., Krizsan ´, K., Kiss, B., Hess, J., Varga, T., Slot, J., Riley, R., B´oka, B., Rigling, D., Barry, K., Lee, J., Mihaltcheva, S., LaButti, K., Lipzen, A., Waldron, R., Moloney, N.M., Sperisen, C., Kredics, L., V´agv¨olgyi, C., Patrignani, A., Fitzpatrick, D., Nagy, I., Doyle, S., Anderson, J.B., Grigoriev, I.V., Guldener, U., Munsterkotter ¨, M., Nagy, L.G., 2017. Genome expansion and lineage-specific genetic innovations in the forest pathogenic fungi Armillaria. Nat. Ecol. Evol. 1, 1931-1941. https://doi.org/10.1038/s41559- 017-0347-8.
  • Sofreni´c, I., Andelkovic ´, B., Todorovi´c, N., Stanojkovi´c, T., Vujisi´c, L., Novakovi´c, M., Milosavljevi´c, S., Teˇsevi´c, V., 2021. Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina. Phytochemistry 181, 112580. https://doi.org/10.1016/j.phytochem.2020.112580.
  • Tang, Y., Zhao, Z.-Z., Feng, T., Li, Z.-H., Chen, H.-P., Liu, J.-K., 2019a. Triterpenes with unusual modifications from the fruiting bodies of the medicinal fungus Irpex lacteus. Phytochemistry 162, 21-28. https://doi.org/10.1016/j.phytochem.2019.02.017.
  • Tang, Y., Zhao, Z.-Z., Hu, K., Feng, T., Li, Z.-H., Chen, H.-P., Liu, J.-K., 2019b. Irpexolidal represents a class of triterpenoid from the fruiting bodies of the medicinal fungus Irpex lacteus. J. Org. Chem. 84, 1845-1852. https://doi.org/10.1021/acs.
  • Tang, Y., Zhao, Z.-Z., Yao, J.-N., Feng, T., Li, Z.-H., Chen, H.-P., Liu, J.-K., 2018. Irpeksins A-E, 1,10-seco-eburicane-type triterpenoids from the medicinal fungus Irpex lacteus and their anti-NO activity. J. Nat. Prod. 81, 2163-2168. https://doi.org/10.1021/ acs.jnatprod.7b00845.
  • Toghueo, R.M.K., Sahal, D., Boyom, F.F., 2020. Recent advances in inducing endophytic fungal specialized metabolites using small molecule elicitors including epigenetic modifiers. Phytochemistry 174, 112338. https://doi.org/10.1016/j.
  • Wang, M., Du, J.-X., Hui-Xiang, Y., Dai, Q., Liu, Y.-P., He, J., Wang, Y., Li, Z.-H., Feng, T., Liu, J.-K., 2020. Sesquiterpenoids from cultures of the basidiomycetes Irpex lacteus. J. Nat. Prod. 83, 1524-1531. https://doi.org/10.1021/acs.jnatprod.9b01177.
  • Weber, D., Erosa, G., Sterner, O., Anke, T., 2006. New bioactive sesquiterpenes from Ripartites metrodii and R. tricholoma. Z. Naturforsch. C Biosci. 61, 663-669. https:// doi.org/10.1515/znc-2006-9-1009.
  • Wu, H., Yang, H.-X., Li, Z.-H., Feng, T., Liu, J.-K., 2021. Psathyrellins A-E, antibacterial guanacastane diterpenoids from mushroom Psathyrella candolleana. Nat. Prod.
  • Xu, W.S., Parmigiani, R.B., Marks, P.A., 2007. Histone deacetylase inhibitors: molecular mechanisms of action. Oncogene 26, 5541-5552. https://doi.org/10.1038/sj.
  • Yang, Y.-L., Zhou, H., Du, G., Feng, K.-N., Feng, T., Fu, X.-L., Liu, J.-K., Zeng, Y., 2016. A monooxygenase from Boreostereum vibrans catalyzes oxidative decarboxylation in a divergent vibralactone biosynthesis pathway. Angew. Chem. Int. Ed. 55, 5463-5466. https://doi.org/10.1002/anie.201510928.
  • Yin, X., Wei, J., Wang, W.-W., Gao, Y.-Q., Stadler, M., Kou, R.-W., Gao, J.-M., 2019. New cyathane diterpenoids with neurotrophic and anti-neuroinflammatory activity from the bird' s nest fungus Cyathus africanus. Fitoterapia 134, 201-209. https://doi.org/ 10.1016/j.fitote.2019.02.013.
  • Yoshikawa, K., Kaneko, A., Matsumoto, Y., Hama, H., Arihara, S., 2006. Russujaponols A F, illudoid sesquiterpenes from the fruiting body of Russula japonica. J. Nat. Prod. 69, 1267-1270. https://doi.org/10.1021/np068006a.
  • Zhang, F.-L., Shi, C., Sun, L.-T., Yang, H.-X., He, J., Li, Z.-H., Feng, T., Liu, J.-K., 2021. Chemical constituents and their biological activities from the mushroom Pyropolyporus fomentarius. Phytochemistry 183, 112625. https://doi.org/10.1016/j. phytochem.2020.112625.
  • Zhang, F.-L., Yang, H.-X., Wu, X., Li, J.-Y., Wang, S.-Q., He, J., Li, Z.-H., Feng, T., Liu, J.- K., 2020. Chemical constituents and their cytotoxicities from mushroom Tricholoma imbricatum. Phytochemistry 177, 112431. https://doi.org/10.1016/j.
  • Zhao, P.-J., Yang, Y.-L., Du, L., Liu, J.-K., Zeng, Y., 2013. Elucidating the biosynthetic pathway for vibralactone: a pancreatic lipase inhibitor with a fused bicyclic β- lactone. Angew. Chem. Int. Ed. 52, 2298-2302. https://doi.org/10.1002/ anie.201208182.
  • Zhao, Z.-Z., Zhao, K., Chen, H.-P., Bai, X., Zhang, L., Liu, J.-K., 2018. Terpenoids from the mushroom-associated fungus Montagnula donacina. Phytochemistry 147, 21-29. https://doi.org/10.1016/j.phytochem.2017.12.015.
  • Zheng, Y., Shen, Y., 2009. Clavicorolides A and B, sesquiterpenoids from the fermentation products of edible fungus Clavicorona pyxidata. Org. Lett. 11, 109-112. https://doi.org/10.1021/ol8024549.
  • Zhou, Z.-Y., Liu, J.-K., 2010. Pigments of fungi (macromycetes). Nat. Prod. Rep. 27, 1531-1570. https://doi.org/10.1039/C004593D.
  • Zhou, Z.-Y., Shi, G.-Q., Fontaine, R., Wei, K., Feng, T., Wang, F., Wang, G.-Q., Qu, Y., Li, Z.-H., Dong, Z.-J., Zhu, H.-J., Yang, Z.-L., Zeng, G., Liu, J.-K., 2012. Evidence for the natural toxins from the mushroom Trogia venenata as a cause of sudden unexpected death in Yunnan Province, China. Angew. Chem. Int. Ed. 51, 2368-2370. https://doi.org/10.1002/anie.201106502.