A new isoquinoline and ceramide from the stem barks of Discoglypremna caloneura (Pax) Prain (Euphorbiaceae) with antiproteinase and cytotoxic activities

Abstract

Two new compounds, an isoquinoline (1) and caloneuramide (2), a ceramide were isolated from the stem bark of Discoglypremna caloneura together with seven known compounds namely aurantiamide acetate (3), acetylaleuritolic acid (4), 3α-hydroxylaleuritolic acid 2 α-phydroxybenzoate (5), mixture of stigmasterol (6) and β-sitosterol (7), mixture of 7-oxo-stigmasterol (8) and 7-oxo-β-sitosterol (9). Their structures were determined based on data from literature and spectroscopic methods. Derivatization reactions on the isoquinoline led to two new compounds, the methylated (10) and acetylated (11) derivatives. Some compounds and extracts were evaluated for their cytotoxic and antiproteinase activity. Antiproteinase effect of compounds 1, 10 and 11 exhibited IC50 values of 10.77, 1.19 and 3.61 µg/mL respectively; significantly low compared to the standard drug, acetyl salicylic acid (IC50 = 20.28 µg/mL). Ethyl acetate and methanol extract exhibited moderate cytotoxicity activity on Chang liver cells with CC50 values of 167.90±2.20 and 106.30 ±2.03 µg/mL compared to the reference drug cucurmin (CC50 = 11.05 ± 1.04 µg/mL).

SARS-CoV-2 main protease inhibitors from the stem barks of Discoglypremna caloneura (Pax) Prain (Euphorbiaceae) and Pterocarpus erinaceus Poir (Fabaceae) and their molecular docking investigation

“…A total of twelve compounds (1, 4-14) were previously isolated and characterised from stem barks of P. erinaceus [12] and D. caloneura [13]. Compound 1 was reduced and acetylated to furnish respectively racemic mixtures of friedelan-3-ol (2) and friedelan-3-acetoxy (3).…”

“…Compounds were isolated using chromatographic techniques such as TLC, column chromatography (normal and reversed phase) over silica gel and sephadex LH-20 with gradient and isocratic solvent systems. Compounds 1 and 4-7 were isolated from the stem bark of P. erinaceus [12], and 8-14 were isolated from the stem bark of D. caloneura [13].…”

“…Researchers also found that M pro can indirectly affect cytokine expression; therefore, anti-inflammatory molecules as inhibitors of this enzyme may have double benefit on coronavirus patients [11]. Hence, the present study evaluated the inhibition potential of anti-inflammatory compounds previously isolated [12,13] from Pterocarpus erinaceus (Poir) and Discoglypremna caloneura (Prain) on M pro and evaluated the molecular docking potential of three compounds in order to speculate on the structure activity relationship observed.…”

New Spirostane from a Fungus Neohelicomyces hyalosporus and Its Bioactivity

“…At our previous work, the Neohelicomyces hyalosporus PF11-1 exhibited better antitumor activity by solid fermentation culture of oat. A new spirostane neohelicomyine B (1), together with six known compounds, (25R)-spirost-5-en-3β,7α,12β,25α-tetrol (2), [10] nuatigenin (3), [11] cerevisterol (4), [12] ergosterol (5), [13] βsitosterol (6), [14] citrostadienol (7) [15] were isolated via tracking activity (Figure 1). Herein, we reported the structure elucidation and inhibitory effects of all compounds on A2780, MDA-MB-231, HepG2 and A549/DDP cell lines.…”