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Salicylaldehyde derivatives from a marine-derived fungus Eurotium sp. SCSIO F452


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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  1. Newman DJ, Cragg GM. Marine natural products and related compounds in clinical and advanced preclinical trials. J Nat Prod 2004;67:1216–38.

    Article  CAS  Google Scholar 

  2. Carroll AR, Copp BR, Davis RA, Keyzers RA, Prinsep MR. Marine natural products. Nat Prod Rep. 2019;36:122–73.

    Article  CAS  Google Scholar 

  3. 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.

    Article  CAS  Google Scholar 

  4. 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.

    Article  CAS  Google Scholar 

  5. 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.

    Article  CAS  Google Scholar 

  6. 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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  8. 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.

    Article  Google Scholar 

  9. 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.

    Article  CAS  Google Scholar 

  10. 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.

    Article  CAS  Google Scholar 

  11. 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.

    Article  CAS  Google Scholar 

  12. 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.

    Google Scholar 

  13. 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.

    Article  CAS  Google Scholar 

  14. 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.

    Article  CAS  Google Scholar 

  15. 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.

    Article  CAS  Google Scholar 

  16. 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.

    Article  CAS  Google Scholar 

  17. 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.

    Article  CAS  Google Scholar 

  18. 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.

    Article  CAS  Google Scholar 

  19. 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.

    Article  CAS  Google Scholar 

  20. 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.

    Article  CAS  Google Scholar 

  21. Ran H, Li SM. Fungal benzene carbaldehydes: occurrence, structural diversity, activities and biosynthesis. Nat Prod Rep. 2020;

  22. 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.

    Article  CAS  Google Scholar 

  23. 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.

    Article  CAS  Google Scholar 

  24. Cho JY, Kim MS. Antibacterial benzaldehydes produced by seaweed-derived Streptomyces atrovirens PK288-21. Fish Sci. 2012;78:1065–73.

    Article  CAS  Google Scholar 

  25. 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.

    Article  Google Scholar 

  26. 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.

    Article  CAS  Google Scholar 

  27. 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.

    Article  CAS  Google Scholar 

  28. 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.

    Article  Google Scholar 

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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. [2020]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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Correspondence to Fazuo Wang or Si Zhang.

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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).

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