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. 2017 Jun 9;15(6):169.
doi: 10.3390/md15060169.

Trichodermanins C-E, New Diterpenes with a Fused 6-5-6-6 Ring System Produced by a Marine Sponge-Derived Fungus

Takeshi Yamada  1 , Mayo Suzue  2 , Takanobu Arai  3 , Takashi Kikuchi  4 , Reiko Tanaka  5
Affiliations

Trichodermanins C-E, New Diterpenes with a Fused 6-5-6-6 Ring System Produced by a Marine Sponge-Derived Fungus

Takeshi Yamada et al. Mar Drugs. .

Abstract

Trichodermanins C-E (1-3), new diterpenes with a rare fused 6-5-6-6 ring system, have been isolated from a fungus Trichoderma harzianum OUPS-111D-4 separated from a piece of a marine sponge Halichondria okadai, and these chemical structures have been established by spectroscopic analyses using IR, MASS, HRFABMS, and NMR spectra. We established their absolute stereostructures by application of the modified Mosher's method. In addition, 1 inhibited the growth of cancer cell lines potently.

Keywords: 6-5-6-6 ring system; Halichondria okadai; Trichoderma harzianum; cytotoxicity; diterpenes; marine microorganism; trichodermanins.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of trichodermanins C–E (1–3).
Figure 2
Figure 2
The key 1H-1H COSY and HMBC correlations of 1–3.
Figure 3
Figure 3
Key NOESY correlations of 1.
Figure 4
Figure 4
1H chemical-shift differences between the (S)- and (R)-MTPA esters 1a/1b, and 2a/2b, respectively.
See this image and copyright information in PMC

References

    1. Nicoletti R., Trincone A. Bioactive compounds produced by strains of Penicillium and Talaromyces of marine origin. Mar. Drugs. 2016;14:37. doi: 10.3390/md14020037. - DOI - PMC - PubMed
    1. Imhoff J.F. Natural products from marine fungi-still anunderrepresented resource. Mar. Drugs. 2016;14:19. doi: 10.3390/md14010019. - DOI - PMC - PubMed
    1. Muroga Y., Yamada T., Numata A., Tanaka R. Chaetomugilins I–O, new potent cytotoxic metabolites from a marine-fish-derived Chaetomium species. Stereochemistry and biological activities. Tetrahedron. 2009;65:7580–7586. doi: 10.1016/j.tet.2009.06.125. - DOI
    1. Yamada T., Kitada H., Kajimoto T., Numata A., Tanaka R. The relationship between the CD cotton effect and the absolute configuration of FD-838 and its seven stereoisomers. J. Org. Chem. 2010;75:4146–4153. doi: 10.1021/jo100496f. - DOI - PubMed
    1. Yamada T., Kikuchi T., Tanaka R., Numata A. Halichoblelides B and C, potent cytotoxic macrolides from a Streptomyces species separated from a marine fish. Tetrahedron Lett. 2012;53:2842–2846. doi: 10.1016/j.tetlet.2012.03.114. - DOI

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