Secoemestrin D, a cytotoxic epitetrathiodioxopiperizine, and emericellenes a-e, five sesterterpenoids from emericella sp. AST0036, a fungal endophyte of astragalus lentiginosus 1

Ya Ming Xu, Patricia Espinosa-Artiles, Mangping X. Liu, Anne E Arnold, Leslie Gunatilaka

Research output: Contribution to journalArticle

22 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)2330-2336
Number of pages7
JournalJournal of Natural Products
Volume76
Issue number12
DOIs
StatePublished - Dec 27 2013

Fingerprint

Emericella
Endophytes
Metabolites
Sterigmatocystin
Cells
Bearings (structural)
Tumor Cell Line
Skeleton
Glioma
Inhibitory Concentration 50
Adenocarcinoma
Breast
Carbon
Fibroblasts
Cytotoxicity
Cell Line
Tumors
Nuclear magnetic resonance
Tissue
secoemestrin D

ASJC Scopus subject areas

  • Complementary and alternative medicine
  • Molecular Medicine
  • Organic Chemistry
  • Analytical Chemistry
  • Pharmaceutical Science
  • Pharmacology
  • Drug Discovery

Cite this

Secoemestrin D, a cytotoxic epitetrathiodioxopiperizine, and emericellenes a-e, five sesterterpenoids from emericella sp. AST0036, a fungal endophyte of astragalus lentiginosus 1. / Xu, Ya Ming; Espinosa-Artiles, Patricia; Liu, Mangping X.; Arnold, Anne E; Gunatilaka, Leslie.

In: Journal of Natural Products, Vol. 76, No. 12, 27.12.2013, p. 2330-2336.

Research output: Contribution to journalArticle

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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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