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. 2014 May 28;12(6):3190-202.
doi: 10.3390/md12063190.

New prenylxanthones from the deep-sea derived fungus Emericella sp. SCSIO 05240

Mangaladoss Fredimoses  1 , Xuefeng Zhou  2 , Xiuping Lin  3 , Xinpeng Tian  4 , Wen Ai  5 , Junfeng Wang  6 , Shengrong Liao  7 , Juan Liu  8 , Bin Yang  9 , Xianwen Yang  10 , Yonghong Liu  11
Affiliations

New prenylxanthones from the deep-sea derived fungus Emericella sp. SCSIO 05240

Mangaladoss Fredimoses et al. Mar Drugs. .

Abstract

Four new prenylxanthones, emerixanthones A-D (1-4), together with six known analogues (5-10), were isolated from the culture of the deep-sea sediment derived fungus Emericella sp. SCSIO 05240, which was identified on the basis of morphology and ITS sequence analysis. The newstructures were determined by NMR (1H, 13C NMR, HSQC, HMBC, and 1H-1H COSY), MS, CD, and optical rotation analysis. The absolute configuration of prenylxanthone skeleton was also confirmed by the X-ray crystallographic analysis. Compounds 1and 3 showed weak antibacterial activities, and 4 displayed mild antifungal activities against agricultural pathogens.

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Figures

Figure 1
Figure 1
Colony appearance and micromorphology of strain SCSIO 05240. (a) Colony appearance after 7 days at 25 °C (PDA); (b) Conidiophores under SEM; (c) Conidia under SEM; (d) Cleistothecia as seening using SEM. Bars: 15 μM (b), 5 μM (c), and 50 μM (d).
Figure 2
Figure 2
Neighbor-joining tree based on sequences of ITS region, showing phylogenetic relationships between Emericella sp. SCSIO 05240 and related Emericella species. Numbers at nodes indicate bootstrap values from 1000 replicates. GenBank accession numbers are given in parentheses. Bar, 0.2% sequence divergence.
Figure 3
Figure 3
Chemical structures of compounds 1–10.
Figure 4
Figure 4
X-ray structure of compound 8.
Figure 5
Figure 5
Key HMBC and COSY correlations of compound 1.
Figure 6
Figure 6
Circular dichroism spectra of compounds 1–3.
Figure 7
Figure 7
Proposed biosynthetic pathway of compounds 1–10.
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