Maleimide and Maleic Anhydride Derivatives from the Mycelia of Antrodia cinnamomea and Their Nitric Oxide Inhibitory Activities in Macrophages

Abstract

On cultivation of the fungus Antrodia cinnamomea (BCRC 36799) on a medium, the mycelium was extracted and evaluated for nitric oxide (NO) inhibitory activity. Bioactivity-directed fractionation led to the isolation of two new maleimide derivatives, antrocinnamomins A (1) and B (2), and two new maleic anhydride derivatives, antrocinnamomins C (3) and D (4), along with three known compounds, 3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]furan-2,5-dione (5), 3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]-1H-pyrrole-2,5-dione (6), and 3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]-1H-pyrrol-1-ol-2,5-dione (7). Structural elucidation of compounds 1-4 was carried out by spectroscopic data. Compound 1 displayed significant inhibitory effect on nitric oxide (NO) production.

Microwave-promoted synthesis of cyclic imides

“…The activity of maleimides as antifungal, antimicrobial and insecticide compounds has been reported. 2,[20][21][22][23][24] These compounds have also proved to have analgesic and antispasmodic activities. 2 They can also form conjugates with peptides and antibodies and act as enzyme inhibitors.…”

“…2 They can also form conjugates with peptides and antibodies and act as enzyme inhibitors. [21][22][23][24][25] The maleimide moiety can be used as a versatile synthesis platform due to its Michael accepting [26][27][28][29] and dienophilic nature, as well as its dipolarophile characteristic in 1,3-dipolar cycloadditions. [30][31][32][33] A recent review shows the importance of maleimides as building blocks for the synthesis of polymers.…”

Rapid Evaluation of Antrodia camphorata Natural Products and Derivatives in Tumourigenic Liver Progenitor Cells with a Novel Cell Proliferation Assay

“…[5] A yellow oil, 72 % yield; General Suzuki cross-coupling procedure A: A magnetically stirred solution of PdCl 2 A C H T U N G T R E N N U N G (dppf) (11 mol %), tetramethyldioxaborolane or phenylbronic acid (1-1.5 mol equiv) in THF (5.0 mL mmol À1 ) was treated with NaOH (3 mol equiv in H 2 O) and chloromaleimide 7 (1 mol equiv in THF, 0.5 mL mmol À1 ) at room temperature. The ensuing mixture was degassed, and then stirred at 45 8C for approximately 16 h. The reaction mixture was cooled to room temperature before being fused to silica (~300 mg mmol…”

“…More recently, Yuan and colleagues isolated an additional series of related compounds (phenols 4 and 5) from the same fungal species and reported their nitric oxide inhibitory activity. [5] Surprisingly, there has been no additional studies to our knowledge on the direct effect of these compounds in liver cell lines to accompany early reports that the natural source was used to treat related complications in indigenous practice.…”

Antifungal activity of simple compounds with maleic anhydride or dimethylmaleimide structure against <i>Botrytis cinerea</i>

“…Natural products with a maleimide structure also have high biological activities, such as showdomycin 9, 19,20) aqabamycins 10, 21) and arcyria avins 11, 22) also have high biological activities (Fig. 2).…”