Two pairs of new salicylaldehyde derivative enantiomers, salicylaldehydiums A and B (1 and 2), along with five known analogues were isolated and identified from a marine-derived fungus Eurotium sp. SCSIO F452. Their structures and absolute configuration were determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. All the new optical pure enantiomers [(+)-1, (-)-1, (+)-2, (-)-2] were evaluated for their cytotoxic and antioxidative activities. Compound (-)-1 exhibited weak cytotoxic activity.
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Newman DJ, Cragg GM. Marine natural products and related compounds in clinical and advanced preclinical trials. J Nat Prod 2004;67:1216–38.
Carroll AR, Copp BR, Davis RA, Keyzers RA, Prinsep MR. Marine natural products. Nat Prod Rep. 2019;36:122–73.
Ma LF, Chen MJ, Liang DE, Shi LM, Ying YM, Shan WG, et al. Streptomyces albogriseolus SY67903 produces eunicellin diterpenoids structurally similar to terpenes of the gorgonian Muricella sibogae, the bacterial source. J Nat Prod. 2020;83:1641–5.
Liu N, Peng S, Yang J, Cong Z, Lin X, Liao S, et al. Structurally diverse sesquiterpenoids and polyketides from a sponge-associated fungus Aspergillus sydowii SCSIO41301. Fitoterapia. 2019;135:27–32.
Cipres A, O’Malley DP, Li K, Finlay D, Baran PS, Vuori K. Sceptrin, a marine natural compound, inhibits cell motility in a variety of cancer cell lines. ACS Chem Biol. 2010;5:195–202.
Wang FZ, Huang Z, Shi XF, Chen YC, Zhang WM, Tian XP, et al. Cytotoxic indole diketopiperazines from the deep sea-derived fungus Acrostalagmus luteoalbus SCSIO F457. Bioorg Med Chem Lett. 2012;22:7265–7.
Huang H, Wang F, Luo M, Chen Y, Song Y, Zhang W, et al. Halogenated anthraquinones from the marine-derived fungus Aspergillus sp. SCSIO F063. J Nat Prod. 2012;75:1346–52.
Zhong WM, Wang JF, Shi XF, Wei XY, Chen YC, Zeng Q, et al. Eurotiumins A-E, five new alkaloids from the marine-derived fungus Eurotium sp. SCSIO F452. Mar Drugs. 2018;16:136.
Zhong W-M, Wang J-F, Wei X-Y, Zeng Q, Chen X-Y, Xiang Y, et al. (+)- and (−)-Eurotone A: a pair of enantiomeric polyketide dimers from a marine-derived fungus Eurotium sp. SCSIO F452. Tetrahedron Lett. 2019;60:1600–3.
Zhong W, Wang J, Wei X, Chen Y, Fu T, Xiang Y, et al. Variecolortins A-C, three pairs of spirocyclic diketopiperazine enantiomers from the marine-derived fungus Eurotium sp. SCSIO F452. Org Lett. 2018;20:4593–6.
Zhong W, Wang J, Wei X, Fu T, Chen Y, Zeng Q, et al. Three pairs of new spirocyclic alkaloid enantiomers from the marine-derived fungus Eurotium sp. SCSIO F452. Front Chem. 2019;7:350.
Wang FZ, Huang Z, Shi XF, Chen YC, Zhang WM, Tian XP, et al. Analysis of secondary metabolites produced by Eurotium sp. SCSIO F452 isolated from the South China Sea sediment. Zhongguo Haiyang Yaowu. 2013;32:7–12.
Prado S, Janin YL, Bost PE. A simple two steps ytterbium triflate-catalysed preparation of 2,2-dimethyl-2H-chromenes from salicylaldehydes and 2-methylpropene. J Heterocycl Chem. 2006;43:1605–8.
Halpin RA, El-Naggar SF, McCombe KM, Vyas KP, Boyd DR, Jerina DM. Resolution and assignement of absolute configuration to the (+)- and (−)-cis and trans 3,4-diol metabolites of the anti-juvenile hormone precocene I. Tetrahedron Lett. 1982;23:1655–8.
Li DL, Li XM, Li TG, Dang HY, Proksch P, Wang BG. Benzaldehydes from Eurotium rubrum, an endophytic fungus derived from the mangrove plant Hibiscus tiliaceus. Chem Pharm Bull. 2008;56:1282–5.
Miyake Y, Ito C, Itoigawa M, Osawa T. Antioxidants produced by Eurotium herbariorum of filamentous fungi used for the manufacture of karebushi, dried bonito (Katsuobushi). Biosci Biotech Bioch. 2009;73:1323–7.
Shi YN, Yang L, Zhao JH, Shi YM, Qu Y, Zhu HT, et al. Chemical constituents from Piper wallichii. Nat Prod Res. 2015;29:1372–5.
Kwon J, Lee H, Ko W, Kim D-C, Kim K-W, Kwon HC, et al. Chemical constituents isolated from Antarctic marine-derived Aspergillus sp. SF-5976 and their anti-inflammatory effects in LPS-stimulated RAW 264.7 and BV2 cells. Tetrahedron. 2017;73:3905–12.
Nies J, Ran H, Wohlgemuth V, Yin WB, Li SM. Biosynthesis of the prenylated salicylaldehyde flavoglaucin requires temporary reduction to salicyl alcohol for decoration before reoxidation to the final product. Org Lett. 2020;22:2256–60.
Gould BS, Raistrick H. Studies in the biochemistry of micro-organisms: the crystalline pigments of species in the Aspergillus glaucus series. Biochem J. 1934;28:1640–56.
Ran H, Li SM. Fungal benzene carbaldehydes: occurrence, structural diversity, activities and biosynthesis. Nat Prod Rep. 2020;https://doi.org/10.1039/d0np00026d.
Shi J, Liu J, Kang D, Huang Y, Kong W, Xiang Y, et al. Isolation and characterization of benzaldehyde derivatives with anti-inflammatory activities from Eurotium cristatum, the dominant fungi species in Fuzhuan brick tea. ACS Omega. 2019;4:6630–6.
Chen M, Shao C-L, Wang K-L, Xu Y, She Z-G, Wang C-Y. Dihydroisocoumarin derivatives with antifouling activities from a gorgonian-derived Eurotium sp. fungus. Tetrahedron. 2014;70:9132–8.
Cho JY, Kim MS. Antibacterial benzaldehydes produced by seaweed-derived Streptomyces atrovirens PK288-21. Fish Sci. 2012;78:1065–73.
Zhong W, Chen Y, Mai Z, Wei X, Wang J, Zeng Q, et al. Euroticins A and B, two pairs of highly constructed salicylaldehyde derivative enantiomers from a marine-derived fungus Eurotium sp. SCSIO F452. J Org Chem. 2020;85:12754–9.
Chen M, Zhao Q, Hao J-D, Wang C-Y. Two benzaldehyde derivatives and their artefacts from a gorgonian-derived Eurotium sp. fungus. Nat Prod Res. 2017;31:268–74.
Dou M, Di L, Zhou LL, Yan YM, Wang XL, Zhou FJ, et al. Cochlearols A and B, polycyclic meroterpenoids from the fungus Ganoderma cochlear that have renoprotective activities. Org Lett. 2014;16:6064–7.
Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst. 1990;85:1107–12.
This work was financially supported by the National Key Research and Development Program of China (2019YFC0312503, 2017YFC0506300), National Natural Science Foundation of China (41476136, 41890853, 41776169), Guangdong Provincial Special Fund for Marine Economic Development Project (Yue Natural Resources Contract No. 042), and the Pearl River S&T Nova Program of Guangzhou (201710010136). We gratefully acknowledge help from the equipment public service center (Dr Xiao, Ms Sun, Ms Zhang, and Dr Zheng) in SCSIO for measuring spectroscopic data and support from the Guangzhou Branch of the Supercomputing Center of Chinese Academy of Sciences.
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Zhong, W., Chen, Y., Wei, X. et al. Salicylaldehyde derivatives from a marine-derived fungus Eurotium sp. SCSIO F452. J Antibiot 74, 273–279 (2021). https://doi.org/10.1038/s41429-020-00395-x