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. 2015 Jun 5;13(6):3567-80.
doi: 10.3390/md13063567.

Drimane Sesquiterpene-Conjugated Amino Acids from a Marine Isolate of the Fungus Talaromyces minioluteus (Penicillium Minioluteum)

Affiliations

Drimane Sesquiterpene-Conjugated Amino Acids from a Marine Isolate of the Fungus Talaromyces minioluteus (Penicillium Minioluteum)

Suthatip Ngokpol et al. Mar Drugs. .

Abstract

Four new sesquiterpene lactones (3, 4, 6 and 7) and three known compounds, purpuride (1), berkedrimane B (2) and purpuride B (5), were isolated from the marine fungus, Talaromyces minioluteus (Penicillium minioluteum). New compounds were drimane sesquiterpenes conjugated with N-acetyl-l-valine, and their structures were elucidated by analysis of spectroscopic data, as well as by single crystal X-ray analysis. The isolated compounds could not inhibit the apoptosis-regulating enzyme, caspase-3, while three of the compounds (2, 3 and 7) exhibited weak cytotoxic activity.

Keywords: Penicillium minioluteum; Talaromyces minioluteus; caspase-3; cytotoxic activity; drimane; fungal metabolites; marine fungi; sesquiterpene.

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Figures

Figure 1
Figure 1
Structure of fungal metabolites 17.
Figure 2
Figure 2
ORTEP plot (20% probability level) of 3 (color codes: C = cyan, O = red, N = purple, Cl = green, H = white). The molecule is stabilized by an intermolecular O–H···O hydrogen bond (magenta) with a disordered water molecule (occupancy factor 0.25).
Figure 3
Figure 3
Effect of compounds 17 on caspase-3 enzymatic activity. Apoptotic HepG2 cell lysates were individually incubated with various concentrations (12.5–200 μM) of purpuride (1) and 200 µM of compounds 27. A caspase-3 inhibitor (5 µM), Z-DEVD-fmk, was used as a positive control. Data are mean + SD of three independent experiments. Ctl = A control without compounds.

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