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. 2013 Dec 27;76(12):2330-6.
doi: 10.1021/np400762k. Epub 2013 Nov 19.

Secoemestrin D, a cytotoxic epitetrathiodioxopiperizine, and emericellenes A-E, five sesterterpenoids from Emericella sp. AST0036, a fungal endophyte of Astragalus lentiginosus1

Ya-Ming Xu  1 , Patricia Espinosa-Artiles, Mangping X Liu, A Elizabeth Arnold, A A Leslie Gunatilaka
Affiliations

Secoemestrin D, a cytotoxic epitetrathiodioxopiperizine, and emericellenes A-E, five sesterterpenoids from Emericella sp. AST0036, a fungal endophyte of Astragalus lentiginosus1

Ya-Ming Xu et al. J Nat Prod. .

Abstract

A new epitetrathiodioxopiperizine, secoemestrin D (1), and five sesterterpenoids bearing a new carbon skeleton, emericellenes A-E (2-6), together with previously known fungal metabolites, sterigmatocystin (7), arugosin C (8), and epiisoshamixanthone (9), were obtained from the endophytic fungal strain Emericella sp. AST0036 isolated from a healthy leaf tissue of Astragalus lentiginosus. The planar structures and relative configurations of the new metabolites 1-6 were elucidated using MS and 1D and 2D NMR spectroscopic data. All compounds were evaluated for their potential anticancer activity using a panel of six tumor cell lines and normal human fibroblast cells. Only metabolites 1 and 7 showed cytotoxic activity. More importantly, secoemestrin D (1) exhibited significant cytotoxicity with IC50 values ranging from 0.06 to 0.24 μM and moderate selectivity to human glioma (SF-268) and metastatic breast adenocarcinoma (MDA-MB-231) cell lines.

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Figures

Figure 1
Figure 1
Structures of metabolites 1–9 from Emericella sp. AST0036
Figure 2
Figure 2
Key HMBC correlations for secoemestrin D (1)
Figure 3
Figure 3
Significant HMBC and TOCSY correlations for emericellene A (2)
Figure 4
Figure 4
Key NOE correlations for emericellene A (2)
Figure 5
Figure 5
Possible biosynthetic pathway to emericellane-type sesterterpenoids
See this image and copyright information in PMC

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