Published September 30, 2021 | Version v1

Five undescribed steroids from Talaromyces stipitatus and their cytotoxic activities against hepatoma cell lines

  • 1. ** & *** & * & Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan,

Description

Zhang, Mi, Deng, Yanfang, Liu, Fei, Zheng, Meijia, Liang, Yu, Sun, Weiguang, Li, Qin, Li, Xiao-Nian, Qi, Changxing, Liu, Junjun, Chen, Chunmei, Zhu, Hucheng, Zhang, Yonghui (2021): Five undescribed steroids from Talaromyces stipitatus and their cytotoxic activities against hepatoma cell lines. Phytochemistry (112816) 189: 1-10, DOI: 10.1016/j.phytochem.2021.112816, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112816

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urn:lsid:plazi.org:pub:006BFFD0FFC1FF9CFFB0FF940A5BFFF8

References

  • Amagata, T., Minoura, K., Numata, A., 1998. Gymnasterones, novel cytotoxic metabolites produced by a fungal strain from a sponge. Tetrahedron Lett. 39, 3773-3774. https://doi.org/10.1016/S0040-4039(98)00613-3.
  • Bryant, F.O., Cutler, H.G., Burla, M.C., Newton, M.G., 1995. Duclauxin ethyl acetate solvate, 2C29H22O11⋅C4H8O2. Acta Crystallogr. C51, 437-440. https://doi.org/ 10.1107/S010827019400394X.
  • Chaudhary, N.K., Crombie, A., Vuong, D., Lacey, E., Piggott, A.M., Karuso, P., 2020. Talauxins: hybrid phenalenone dimers from Talaromyces stipitatus. J. Nat. Prod. 83, 1051-1060. https://doi.org/10.1021/acs.jnatprod.9b01066.
  • Deng, C.M., Liu, S.X., Huang, C.H., Pang, J.Y., Lin, Y.C., 2013. Secondary metabolites of a mangrove endophytic fungus Aspergillus terreus (No. GX7-3B) from the South China Sea. Mar. Drugs 11, 2616-2624. https://doi.org/10.3390/md11072616.
  • Duecker, F.L., Heinze, R.C., Heretsch, P., 2020. Synthesis of swinhoeisterol A, dankasterone A and B, and periconiastone A by radical framework reconstruction. J. Am. Chem. Soc. 142, 104-108. https://doi.org/10.1021/jacs.9b12899.
  • Gao, S.S., Zhang, T., Garcia-Borras, M., Hung, Y.S., Billingsley, J.M., Houk, K.N., Hu, Y., Tang, Y., 2018. Biosynthesis of heptacyclic duclauxins requires extensive redox modifications of the phenalenone aromatic polyketide. J. Am. Chem. Soc. 140, 6991-6997. https://doi.org/10.1021/jacs.8b03705.
  • Hu, Z., He, B., Ma, L., Sun, Y., Niu, Y., Zeng, B., 2017. Recent advances in ergosterol biosynthesis and regulation mechanisms in Saccharomyces cerevisiae. Indian J. Microbiol. 57, 270-277. https://doi.org/10.1007/s12088-017-0657-1.
  • Keating, G.M., 2017. Sorafenib: a review in hepatocellular carcinoma. Targeted Oncol. 12, 243-253. https://doi.org/10.1007/s11523-017-0484-7.
  • Kikuchi, T., Isobe, M., Uno, S., In, Y., Zhang, J., Yamada, T., 2019. Strophasterols E and F: rearranged ergostane-type sterols from Pleurotus eryngii. Bioorg. Chem. 89, 103011-103019. https://doi.org/10.1016/j.bioorg.2019.103011.
  • Lin, M., Li, H., Zhao, Y., Cai, E., Zhu, H., Gao, Y., Liu, S., Yang, H., Zhang, L., Tang, G., 2017. 2-Naphthoic acid ergosterol ester, an ergosterol derivative, exhibits anti-tumor activity by promoting apoptosis and inhibiting angiogenesis. Steroids 122, 9-15. https://doi.org/10.1016/j.steroids.2017.03.007.
  • Luo, Q., Yang, Z.L., Yan, Y.M., Cheng, Y.X., 2017. Ganotheaecolin A, a neurotrophic conjugated ergosterol with a naphtho[1,8-ef]azulene scaffold from ganoderma theaecolum. Org. Lett. 19, 718-721. https://doi.org/10.1021/acs.orglett.7b00012.
  • Ma, G., Chong, L., Li, Z., Cheung, A.H., Tattersall, M.H., 2009. Anticancer activities of sesquiterpene lactones from Cyathocline purpurea in vitro. Canc. Chemother. Pharmacol. 64, 143-152. https://doi.org/10.1007/s00280-008-0863-y.
  • Noinart, J., Buttachon, S., Dethoup, T., Gales, L., Pereira, J.A., Urbatzka, R., Freitas, S., Lee, M., Silva, A.M.S., Pinto, M.M.M., Vasconcelos, V., Kijjoa, A., 2017. A new ergosterol analog, a new bis-anthraquinone and anti-obesity activity of anthraquinones from the marine sponge-associated fungus Talaromyces stipitatus KUFA 0207. Mar. Drugs 15, 139-151. https://doi.org/10.3390/md15050139.
  • Ohnishi, T., Yokota, T., Mizutani, M., 2009. Insights into the function and evolution of P450s in plant steroid metabolism. Phytochemistry 70, 1918-1929. https://doi.org/ 10.1016/j.phytochem.2009.09.015.
  • Qiao, M.-F., Yi, Y.-W., Deng, J., 2017. Steroids from an endophytic Eurotium rubrum strain. Chem. Nat. Compd. 53, 678-681. https://doi.org/10.1007/s10600-017- 2089-x.
  • Qin, X.-D., Liu, J.-K., 2004. Natural aromatic steroids as potential molecular fossils from the fruiting bodies of the ascomycete daldinia concentrica. J. Nat. Prod. 67, 2133-2135. https://doi.org/10.1021/np049793j.
  • Shi, Q., Huang, Y., Su, H., Gao, Y., Peng, X., Zhou, L., Li, X., Qiu, M., 2019. C28 steroids from the fruiting bodies of Ganoderma resinaceum with potential anti-inflammatory activity. Phytochemistry 168, 112109-121117. https://doi.org/10.1016/j. phytochem.2019.112109.
  • Sokolov, S.S., Trushina, N.I., Severin, F.F., Knorre, D.A., 2019. Ergosterol turnover in yeast: an interplay between biosynthesis and transport. Biochemistry (Mosc.) 84, 346-357. https://doi.org/10.1134/S0006297919040023.
  • Tanaka, R., Kasubuchi, K., Kita, S., Tokuda, H., Nishino, H., Matsunaga, S., 2000.
  • Taro, A., Mitsunobu, D., Makiko, T., Katsuhiko, M., Atsushi, N., 1999. Dankasterone, a new class of cytotoxic steroid produced by a Gymnascella species from a marine sponge. Chem. Commun. 1321-1322. https://doi.org/10.1039/A903840J.
  • Wang, S., Zhang, L., Liu, L.-Y., Dong, Z.-J., Li, Z.-H., Liu, J.-K., 2012. Six novel steroids from culture of basidiomycete Polyporus ellisii. Natur. Prod. & Bioprosp. 2, 240-244. https://doi.org/10.1007/s13659-012-0058-4.
  • Wang, W., Li, F., Park, Y., Hong, J., Lee, C.-O., Kong, J.Y., Shin, S., Im, K.S., Jung, J.H., 2003. Bioactive sterols from the starfish certonardoa semiregularis. J. Nat. Prod. 66, 384-391. https://doi.org/10.1021/np020507i.
  • Weng, Y., Xiang, L., Matsuura, A., Zhang, Y., Huang, Q., Qi, J., 2010. Ganodermasides A and B, two novel anti-aging ergosterols from spores of a medicinal mushroom