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. 2021 Jun 10;19(6):333.
doi: 10.3390/md19060333.

Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete Aspergillus oryzae

Raha Orfali  1 , Shagufta Perveen  1 , Muhammad Farooq Khan  2 , Atallah F Ahmed  1   3 , Mohammad A Wadaan  2 , Areej Mohammad Al-Taweel  1 , Ali S Alqahtani  1   4 , Fahd A Nasr  4 , Sobia Tabassum  5 , Paolo Luciano  6 , Giuseppina Chianese  6 , Jyh-Horng Sheu  7   8 , Orazio Taglialatela-Scafati  6
Affiliations

Antiproliferative Illudalane Sesquiterpenes from the Marine Sediment Ascomycete Aspergillus oryzae

Raha Orfali et al. Mar Drugs. .

Abstract

The new asperorlactone (1), along with the known illudalane sesquiterpene echinolactone D (2), two known pyrones, 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (3) and its acetate 4, and 4-hydroxybenzaldehyde (5), were isolated from a culture of Aspergillus oryzae, collected from Red Sea marine sediments. The structure of asperorlactone (1) was elucidated by HR-ESIMS, 1D, and 2D NMR, and a comparison between experimental and DFT calculated electronic circular dichroism (ECD) spectra. This is the first report of illudalane sesquiterpenoids from Aspergillus fungi and, more in general, from ascomycetes. Asperorlactone (1) exhibited antiproliferative activity against human lung, liver, and breast carcinoma cell lines, with IC50 values < 100 µM. All the isolated compounds were also evaluated for their toxicity using the zebrafish embryo model.

Keywords: Aspergillus oryzae; antiproliferative activity; illudalane sesquiterpenes; marine fungus; zebrafish toxicity.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of metabolites isolated from A. oryzae.
Figure 2
Figure 2
COSY (blue) and key HMBC (red arrows) correlations for compound 1.
Figure 3
Figure 3
The reasonably populated conformers 1a–1c of 1 and their calculated Boltzmann population.
Figure 4
Figure 4
Experimental ECD curve of asperorlactone (red) and calculated ECD curves for R-1 (black) and S-1 (green).
Figure 5
Figure 5
Postulated biosynthesis of asperorlactone (1).
Figure 6
Figure 6
In vivo screening of compounds 1–5 in zebrafish embryos. Representative micrograph of embryos at 3 days poster fertilization, which were treated with compounds 1–5. The zebrafish embryos treated with compounds 2, 3, and 5 developed normally, and there were no obvious differences in morphology and growth between control and treated embryos. The zebrafish embryos treated with >200 µM of 1, however, had cardiac edema and cardiac hypertrophy (black arrow). The zebrafish embryos treated with compound 4 developed normally but were found dead on day 2. All the images are in same magnification, scale is 200 µm.
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