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New naphthyl derivatives from Aspergillus californicus


Two new naphthyl-products calinaphthyltriol A (1) and calinaphthalenone A (2) were isolated from Aspergillus californicus IBT 16748 together with one known compound ophiobolin X (3). Their structures were elucidated by extensive spectroscopic analyses. The absolute configuration of 2 was solved by comparing its optical rotation with data for the known compounds 4, 5, and 6 as well as theoretical calculations. The antibacterial and cytotoxic activities of 1 and 3 were evaluated. Both compounds did not show antibacterial activity (MIC > 96 µg·ml−1) against a few selected clinically relevant Gram positive and Gram negative bacterial strains. However, they showed moderate cytotoxicity against HL-60 cell line with IC50 values of 18 and 24 µg·ml−1, respectively.

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  1. Frisvad JC, Larsen TO. Chemodiversity in the genus Aspergillus. Appl Microbiol Biotechnol. 2015;99:7859–77.

    Article  CAS  Google Scholar 

  2. Alburae NA, Mohammed AE, Alorfi HS, Jamanturki A, Asfour HZ, Alarif WM, et al. Nidulantes of Aspergillus (Formerly Emericella): A treasure trove of chemical diversity and biological activities. Metabolites. 2020;10:1–28.

    Article  Google Scholar 

  3. Sanchez JF, Somoza AD, Keller NP, Wang CCC. Advances in Aspergillus secondary metabolite research in the post-genomic era. Nat Prod Rep. 2012;29:351–71.

    Article  CAS  Google Scholar 

  4. Samson RA, Varga J, Meijer M, Frisvad JC. New taxa in Aspergillus section Usti. Stud Mycol. 2011;69:81–97.

    Article  CAS  Google Scholar 

  5. Chen AJ, Frisvad JC, Sun BD, Varga J, Kocsubé S, Dijksterhuis J, et al. Aspergillus section Nidulantes (formerly Emericella): Polyphasic taxonomy, chemistry and biology. Stud Mycol. 2012;84:1–118.

    Article  Google Scholar 

  6. Zhu T, Lu Z, Fan J, Wang L, Zhu G, Wang Y, et al. Ophiobolins from the mangrove fungus Aspergillus ustus. J Nat Prod. 2018;81:2–9.

    Article  CAS  Google Scholar 

  7. Tsukamoto H, Sato M, Kondo Y. Palladium(0)-catalyzed direct cross-coupling reaction of allyl alcohols with aryl- and vinyl-boronic acids. Chem Commun. 2004;10:1200–1.

    Article  Google Scholar 

  8. Zhou YH, Zhang M, Zhu RX, Zhang JZ, Xie F, Bin LiX, et al. Heptaketides from an endolichenic fungus Biatriospora sp. and their antifungal activity. J Nat Prod. 2016;79:2149–57.

    Article  CAS  Google Scholar 

  9. Quideau S, Lyvinec G, Marguerit M, Bathany K, Ozanne-Beaudenon A, Buffeteau T, et al. Asymmetrie hydroxylative phenol dearomatization through in situ generation of iodanes from chiral iodoarenes and m-CPBA. Angew Chem - Int Ed. 2009;48:4605–9.

    Article  CAS  Google Scholar 

  10. Cacho RA, Jiang W, Chooi YH, Walsh CT, Tang Y. Identification and characterization of the echinocandin b biosynthetic gene cluster from Emericella rugulosa NRRL 11440. J Am Chem Soc. 2012;134:16781–90.

    Article  CAS  Google Scholar 

  11. Wavefunction Inc. Spartan. Irvine, CA: Wavefunction Inc. 2020.

  12. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 16. Wallingford CT: Gaussian, Inc. 2016.

  13. Mennucci B, Tomasi J, Cammi R, Cheeseman JR, Frisch MJ, Devlin FJ, et al. Polarizable Continuum Model (PCM) calculations of solvent effects on optical rotations of chiral molecules. J Phys Chem A. 2002;106:6102–13.

    Article  CAS  Google Scholar 

  14. Rossi D, Nasti R, Collina S, Mazzeo G, Ghidinelli S, Longhi G, et al. The role of chirality in a set of key intermediates of pharmaceutical interest, 3-aryl-substituted-γ-butyrolactones, evidenced by chiral HPLC separation and by chiroptical spectroscopies. J Pharm Biomed Anal. 2017;10:41–51.

    Article  Google Scholar 

  15. Mazzeo G, Cimmino A, Masi M, Longhi G, Maddau L, Memo M, et al. Importance and difficulties in the use of chiroptical methods to assign the absolute configuration of natural products: the case of phytotoxic pyrones and furanones produced by diplodia corticola. J Nat Prod. 2017;80:2406–15.

    Article  CAS  Google Scholar 

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The authors thank Dr. Kasper Enemark-Rasmussen and Associate Professor René Wugt Larsen from Department of Chemistry at the Technical University of Denmark for acquiring NMR and IR data, respectively. YG is financially supported by the China Scholarship Council and Department of Biotechnology and Biomedicine at the Technical University of Denmark.

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Correspondence to Thomas O. Larsen.

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Guo, Y., Ghidinelli, S., de la Cruz, M. et al. New naphthyl derivatives from Aspergillus californicus. J Antibiot 74, 111–114 (2021).

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