Published October 31, 2022
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Aureoterrolides B-M: Eremophilane-type sesquiterpenoids isolated from Aspergillus aureoterreus and their cytotoxicity
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- 1. * & Key Laboratory of Agricultural Microbiomics and Precision Application-Ministry of Agriculture and Rural Affairs, Guangdong Provincial Key Laboratory of Microbial
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Zang, Yi, Zhou, Beiping, Wei, Mengsha, Shi, Zhengyi, Feng, Guangda, Deng, Mingrong, Zhu, Hucheng, Zhang, Yonghui, Zhu, Honghui (2022): Aureoterrolides B-M: Eremophilane-type sesquiterpenoids isolated from Aspergillus aureoterreus and their cytotoxicity. Phytochemistry (113294) 202: 1-10, DOI: 10.1016/j.phytochem.2022.113294, URL: http://dx.doi.org/10.1016/j.phytochem.2022.113294
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- urn:lsid:plazi.org:pub:383EFFA9FC4BFFB8FF8E656A3403F00E
References
- Amand, S., Vallet, M., Guedon, L., Genta-Jouve, G., Wien, F., Mann, S., Dupont, J., Prado, S., Nay, B., 2017. A reactive eremophilane and its antibacterial 2(1H)- Naphthalenone rearrangement product. Witnesses of a Microbial Chemical Warfare. Org. Lett. 19, 4038-4041. https://doi.org/10.1021/acs.orglett.7b01788.
- Bohlmann, F., Misra, L.N., Jakupovic, J., King, R.M., Robinson, H., 1984. Further eudesmanolides from Dimerostemma species. Phytochemistry 23, 1802-1804. https://doi.org/10.1016/S0031-9422(00)83500-1.
- Brock, N.L., Dickschat, J.S., 2013. PR toxin biosynthesis in Penicillium roqueforti. Chembiochem 14, 1189-1193. https://doi.org/10.1002/cbic.201300254.
- Cane, D.E., Kang, I., 2000. Aristolochene synthase: purification, molecular cloning, highlevel expression in Escherichia coli, and characterization of the Aspergillus terreus cyclase. Arch. Biochem. Biophys. 376, 354-364. https://doi.org/10.1006/ abbi.2000.1734.
- Cardona, L., Bardon, A., Garcia, B., Pedro, J.R., 1993. Eudesmane and elemane derivatives from Onopordon acaulon. Phytochemistry 33, 1457-1460. https://doi. org/10.1016/0031-9422(93)85110-D.
- Fang, W., Wang, J.J., Wang, J.F., Shi, L.Q., Li, K.L., Lin, X.P., Min, Y., Yang, B., Tang, L., Liu, Y.H., Zhou, X.F., 2018. Cytotoxic and antibacterial eremophilane sesquiterpenes from the marine-derived fungus Cochliobolus lunatus SCSIO41401. J. Nat. Prod. 81, 1405-1410. https://doi.org/10.1021/acs.jnatprod.8b00015.
- Felicetti, B., Cane, D.E., 2004. Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesis. J. Am. Chem. Soc. 126, 7212-7221. https:// doi.org/10.1021/ja0499593.
- Goyal, R., Chhabra, B.R., Kalsi, P.S., 1990. Three oxygenated alantolides from Inula racemosa. Phytochemistry 29, 2341-2343. https://doi.org/10.1016/0031-9422(90) 83069-D.
- Hou, C.J., Kulka, M., Zhang, J.Z., Li, Y.M., Guo, F.J., 2014. Occurrence and biological activities of eremophilane-type sesquiterpenes. Mini-Rev. Med. Chem. 14, 664-677. https://doi.org/10.2174/1389557514666140820105422.
- Isaka, M., Srisanoh, U., Veeranondha, S., Choowong, W., Lumyong, S., 2009. Cytotoxic eremophilane sesquiterpenoids from the saprobic fungus Berkleasmium nigroapicale BCC 8220. Tetrahedron 65, 8808-8815. https://doi.org/10.1016/j.tet.2009.08.077.
- Jakupovic, J., Jaensch, M., Bohlmann, F., Dillon, M.O., 1988. Eudesmanolides, 5,10-bisepi-eudesmanes and oplopanone derivatives from Ambrosia artemisioides. Phytochemistry 27, 3551-3556. https://doi.org/10.1016/0031-9422(88)80767-2.
- Kawahara, T., Itoh, M., Izumikawa, M., Sakata, N., Tsuchida, T., Shin-ya, K., 2013. Cytotoxic sesquiterpenoids MBJ-0009 and MBJ-0010 from a saprobic fungus Nectria sp. f26111. J. Antibiot. 66, 567-569. https://doi.org/10.1038/ja.2013.45.
- Lin, L.B., Xiao, J., Gao, Y.Q., Zhang, Q., Han, R., Qi, J.Z., Han, W.B., Xu, B., Gao, J.M., 2021. Trinor- and tetranor-eremophilane sesquiterpenoids with antineuroinflammatory activity from cultures of the fungus Septoria rudbeckiae. Phytochemistry 183, 112642. https://doi.org/10.1016/j.phytochem.2020.112642.
- Liu, J.M., Zhang, D.W., Zhang, M., Zhao, J.L., Chen, R.D., Wang, N., Zhang, D., Dai, J.G., 2016. Eremophilane sesquiterpenes from an endophytic fungus periconia species. J. Nat. Prod. 79, 2229-2235. https://doi.org/10.1021/acs.jnatprod.6b00299.
- Mitsui, T., Hayashi, K.I., Kawai, M., Kido, M., Tani, H., Takaoka, D., Matsuura, N., Nozaki, H., 2013. Culcitiolides E-J, six new eremophilane-type sesquiterpene derivatives from Senecio culcitioids. Chem. Pharm. Bull. 61, 816-822. https://doi. org/10.1248/cpb.c13-00243.
- Neese, F., 2012. The ORCA program system. Wiley Interdiscip. Rev. Comput. Mol. Sci. 2, 73-78. https://doi.org/10.1002/wcms.81.
- Neese, F., 2017. Software update: the ORCA program system, version 4.0. Wiley Interdiscip. Rev. Comput. Mol. Sci. 8, e1327. https://doi.org/10.1002/wcms.1327.
- Samson, R.A., Peterson, S.W., Frisvad, J.C., Varga, J., 2011. New species in Aspergillus section Terrei. Stud. Mycol. 69, 39-55. https://doi.org/10.3114/sim.2011.69.04.
- Smith, C.J., Morin, N.R., Bills, G.F., Dombrowski, A.W., Salituro, G.M., Smith, S.K., Zhao, A., MacNeil, D.J., 2002. Novel sesquiterpenoids from the fermentation of xylaria persicaria are sel ective Ligands for the NPYY5 receptor. J. Org. Chem. 67, 5001-5004. https://doi.org/10.1021/jo011054+.
- Stephens, P.J., Harada, N., 2010. ECD cotton effect approximated by the Gaussian curve and other methods. Chirality 22, 229-233. https://doi.org/10.1002/chir.20733.
- Sybyl Software, 2013. Tripos Associates Inc., St. Louis, MO, USA version X 2.0.
- Tabata, Y., Hatsu, M., Kurata, Y., Miyajima, K., Tani, M., Sasaki, T., Kodama, Y., Tsuruoka, T., Omoto, S., 1997a. PF1092A, B and C, new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum I. Taxonomy of producing strain, fermentation, produced and biological activities. J. Antibiot. 50, 304-308. https:// doi.org/10.7164/antibiotics.50.304.
- Tabata, Y., Hatsu, M., Kurata, Y., Miyajima, K., Tani, M., Sasaki, T., Kodama, Y., Tsuruoka, T., Omoto, S., 1997b. PF1092A, B and C, new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum II. Physico-Chemical properties and structure elucidation. J. Antibiot. 50, 309-313. https://doi.org/10.7164/ antibiotics.50.309.
- Triana, J., Eiroa, J.L., Morales, M., Perez, F.J., Brouard, I., Marrero, M.T., Estevez, S., Quintana, J., Estevez, F., Castillo, Q.A., Leon, F., 2013. A chemotaxonomic study of endemic species of genus Tanacetum from the Canary Islands. Phytochemistry 92, 87-104. https://doi.org/10.1016/j.phytochem.2013.04.015.
- Wang, L.Y., Li, M.J., Tang, J.Q., Li, X.F., 2016. Eremophilane sesquiterpenes from a deep marine-derived fungus, Aspergillus sp. SCSIOW2, cultivated in the presence of epigenetic modifying agents. Molecules 21, 473. https://doi.org/10.3390/ molecules21040473.
- Xu, F.M., Morikawa, T., Matsuda, H., Ninomiya, K., Yoshikawa, M., 2004. Structures of new sesquiterpenes and hepatoprotective constituents from the Egyptian herbal medicine Cyperus longus. J. Nat. Prod. 67, 569-576. https://doi.org/10.1021/ np030368k.
- Yuyama, K.T., Fortkamp, D., Abraham, W.R., 2017. Eremophilane-type sesquiterpenes from fungi and their medicinal potential. Biol. Chem. 399, 13-28. https://doi.org/ 10.1515/hsz-2017-0171.
- Zang, Y., Gong, Y.H., Gong, J.J., Liu, J.J., Chen, C.M., Gu, L.H., Zhou, Y., Wang, J.P., Zhu, H.C., Zhang, Y.H., 2020. Fungal polyketides with three distinctive ring skeletons from the fungus Penicillium canescens uncovered by OSMAC and molecular networking strategies. J. Org. Chem. 85, 4973-4980. https://doi.org/10.1021/acs. joc.0c00147.
- Zang, Y., Zhu, H.H., Feng, G.D., Zhou, B.P., 2021. Sesquiterpenoid as Antitumor Agents and Preparation Thereof. Faming Zhuanli Shenqing. Institute of Microbiology, Guangdong Academy of Sciences, China. CN 113603594.
- Zheng, X.Q., Wu, Z., Xu, J., Zhang, X.X., Tu, Y.Z., Lei, J.C., Yuan, R.Y., Cheng, H.T., Wang, Q., Yu, J.Q., 2021. Bioactive sesquiterpenes from Inula helenium. Bioorg. Chem. 114, 105066 https://doi.org/10.1016/j.bioorg.2021.105066.
- Zhou, M., Duan, F.F., Gao, Y., Peng, X.G., Meng, X.G., Ruan, H.L., 2021. Eremophilane sesquiterpenoids from the whole plant of Parasenecio albus with immunosuppressive activity. Bioorg. Chem. 115, 105247 https://doi.org/10.1016/j. bioorg.2021.105247.