Brevianamides with Antitubercular Potential from a Marine-Derived Isolate of Aspergillus versicolor

Abstract

An Aspergillus versicolor isolated from sediment collected from the Bohai Sea, China, yielded the new dimeric diketopiperazine brevianamide S (1), together with three new monomeric cometabolites, brevianamides T (2), U (3), and V (4). Structures were determined by detailed spectroscopic analysis. Brevianamide S exhibited selective antibacterial activity against Bacille Calmette-Guérin (BCG), suggestive of a new mechanism of action that could inform the development of next-generation antitubercular drugs.

Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

“…9). 115 Two new alkaloids, calophyline A (295) and N-methylaspidodasycarpine (296), were isolated from the trunk bark of Winchia calophylla, growing in Yunnan Province and Hainan island, China. The compounds were evaluated for cytotoxicity against a small panel of human cancer cell lines (Fig.…”

“…49). 295 Investigation of the chemical constituents of the deep-seaderived Streptomyces sp. SCSIO 03032, taking advantage of a PCR-based screening approach, led to the isolation of four new bisindole alkaloids, spiroindimicins A (938), B (939), C (940), and D (941).…”

Bulky α,β-dehydroamino acids: their occurrence in nature, synthesis, and applications

“…24) is a dimeric diketopiperazine with antitubercular activity that was isolated from this fungus by Zhang, Capon, and coworkers. 71 The structure of brevianamide J (32b), the oxygenbridged congener of 32a, was established by X-ray crystallographic studies conducted by Zhang and co-workers. 72 Cristatumins A (33, Fig.…”

Antimicrobial Secondary Metabolites—Extraction, Isolation, Identification, and Bioassay

“…Citreamicin A, citreamicin B, and citreaglycon A revealed strong activities against MRSA ATCC 43300 with MIC values of 0.25, 0.25, and 8.0 mg/mL, respectively [97]. A dimeric diketopiperazine, brevianamide S ( Figure 23.10), isolated from Aspergillus versicolor (collected from the Bohai Sea, China), exhibited selective antibacterial activity [98] against Bacille Calmette-Guérin, suggesting a new mechanism of action that could be considered as a new lead for antitubercular drugs. Isorhodoptilometrin -1-methyl ether, emodin, 1-methyl emodin, siderin, arugosin C, and variculanol obtained from the marine fungus A. versicolor were reported to exhibit antimicrobial activity, anticancer activity, and inhibition of Hepatitis C virus protease [99].…”