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. 2023 Dec 18;13(12):1202.
doi: 10.3390/metabo13121202.

Tetraenone A: A New β-Ionone Derivative from Tetraena aegyptia

Ahmed Ashour  1   2 , Asmaa E Sherif  1   2 , Selwan M El-Sayed  3 , Ji-Young Kim  4 , Dae Sik Jang  4 , Abtin Anvari  5 , Abdelbasset A Farahat  5   6 , Sabrin R M Ibrahim  7   8 , Gamal A Mohamed  9 , Bayan E Ainousah  10 , Raghad F Aljohani  11 , Razan R Al-Hejaili  11 , Rahaf H Khoja  11 , Ahmed H E Hassan  3 , Ahmed A Zaki  2   12
Affiliations

Tetraenone A: A New β-Ionone Derivative from Tetraena aegyptia

Ahmed Ashour et al. Metabolites. .

Abstract

In this study, the chemical investigation of Tetraena aegyptia (Zygophyllaceae) led to the identification of a new megastigmene derivative, tetraenone A ((2S, 5R, 6R, 7E)-2-hydroxy-5,6-dihydro-β-ionone) (1), along with (3S, 5R, 6S, 7E)-3-hydroxy-5,6-epoxy-5,6-dihydro-β-ionone- (2), 3,4-dihydroxy-cinnamyl alcohol-4-glucoside (3), 3β,19α-dihydroxy-ursan-28-oic acid (4), quinovic acid (5), p-coumaric acid (6), and ferulic acid (7), for the first time. The chemical structures of 1-7 were confirmed by analysis of their 1D and 2D NMR and HRESIMS spectra and by their comparison with the relevant literature. The absolute configurations of 1 and 2 were assigned based on NOESY interactions and ECD spectra. Conformational analysis showed that 1 existed exclusively in one of the two theoretically possible chair conformers with a predominant s-trans configuration for the 3-oxobut-1-en-1-yl group with the ring, while the half-chair conformer had a pseudo-axial hydroxy group that was predominant over the other half-chair conformation. Boat conformations were not among the most stable conformations, and the s-trans isomerism was in favor of s-cis configuration. In silico investigation revealed that 1 and 2 had more favorable binding interactions with Mpro rather than with TMPRSS2. Accordingly, molecular dynamic simulations were performed on the complexes of compounds 1 and 2 with Mpro to explore the stability of their interaction with the target protein structure. Compounds 1 and 2 might offer a possible starting point for developing covalent inhibitors of Mpro of SARS-CoV-2.

Keywords: SARS-CoV-2; Tetraena aegyptia; drug discovery; health and wellbeing; life on land; megastigmene; tetraenone A.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of compounds 1–7.
Figure 2
Figure 2
CD spectra of compounds 1 and 2.
Figure 3
Figure 3
CD and ECD spectra of compounds 1 and 2.
Figure 4
Figure 4
Compound 1 covalently docked into the active site of Mpro of SARS-CoV-2.
Figure 5
Figure 5
Compound 2 covalently docked into the active site of Mpro of SARS-CoV-2.
Figure 6
Figure 6
Compound 1 covalently docked into the active site of TMPRSS2.
Figure 7
Figure 7
Compound 2 covalently docked into the active site of TMPRSS2.
Figure 8
Figure 8
The ligand–protein RMSD plot of compounds 1 and 2 complexed with Mpro of SARS-CoV2: (A) compound 1; (B) compound 2. Left and right Y-axes represent the RMSD values of protein and ligand in molecular distance unit Angstrom (Å). X-axis demonstrates the time in picoseconds (ps).
Figure 9
Figure 9
The timeline plot of hydrogen bonding interactions between compounds 1 and 2 and Mpro of SARS-CoV2: (A) compound 1; (B) compound 2. Y-axis represents the number of hydrogen bonds, and X-axis demonstrates the time in picoseconds (ps).
Scheme 1
Scheme 1
Extraction of T. aegyptia and isolation of compounds 1–7.
See this image and copyright information in PMC

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