Antibacterial anthraquinone derivatives isolated from a mangrove-derived endophytic fungus Aspergillus nidulans by ethanol stress strategy.

Three new natural products, including a new anthraquinone derivative isoversicolorin C (1), a new xanthone analog isosecosterigmatocystin (2), and a new amino acid derivative, glulisine A (3), along with six related metabolites (4-9) were isolated from the culture broth and mycelia extracts of the mangrove-derived endophytic fungus Aspergillus nidulans MA-143 under 0.1% ethanol stress. Their structures were elucidated by detailed analysis of their NMR spectra, ECD spectrum, and X-ray crystallographic experiments. Compounds 1 and 4 showed potent antibacterial activity against some of the tested microbes.

How does curcumin work with poor bioavailability? Clues from experimental and theoretical studies.

Curcumin is a natural product with multiple biological activities and numerous potential therapeutic applications. However, its poor systemic bioavailability fails to explain the potent pharmacological effects and hinders its clinical application. Using experimental and theoretical approaches, we compared curcumin and its degradation products for its biological activities against Alzheimer's disease (AD), including the superoxide anion radical (O2(.-))-scavenging activity, Aß fibrils (fAß) formation-inhibiting activity, and enzymatic inhibition activity. We showed that compared to the parent compound curcumin, the degradation products mixture possessed higher O2(.-)-scavenging activity and stronger inhibition against fAß formation. The docking simulations revealed that the bioactive degradation products should make important contribution to the experimentally observed enzymatic inhibition activities of curcumin. Given that curcumin is readily degraded under physiological condition, our findings strongly suggested that the degradation products should make important contribution to the diverse biological activities of curcumin. Our novel findings not only provide novel insights into the complex pharmacology of curcumin due to its poor bioavailability, but also open new avenues for developing therapeutic applications of this natural product.

Prenylated indolediketopiperazine peroxides and related homologues from the marine sediment-derived fungus Penicillium brefeldianum SD-273.

Three new indolediketopiperazine peroxides, namely, 24-hydroxyverruculogen (1), 26-hydroxyverruculogen (2), and 13-O-prenyl-26-hydroxyverruculogen (3), along with four known homologues (4-7), were isolated and identified from the culture extract of the marine sediment-derived fungus Penicillium brefeldianum SD-273. Their structures were determined based on the extensive spectroscopic analysis and compound 1 was confirmed by X-ray crystallographic analysis. The absolute configuration of compounds 1-3 was determined using chiral HPLC analysis of their acidic hydrolysates. Each of the isolated compounds was evaluated for antibacterial and cytotoxic activity as well as brine shrimp (Artemia salina) lethality.

4-Phenyl-3,4-dihydroquinolone derivatives from Aspergillus nidulans MA-143, an endophytic fungus isolated from the mangrove plant Rhizophora stylosa.

Six new 4-phenyl-3,4-dihydroquinolone derivatives (1-6) along with the related aflaquinolone A (7) were isolated and identified from the cultures of Aspergillus nidulans MA-143, an endophytic fungus obtained from the fresh leaves of the marine mangrove plant Rhizophora stylosa. Their structures including absolute configurations were determined by spectroscopic analysis and electronic circular dichroism experiments, and the structure of compound 1 was confirmed by single-crystal X-ray crystallographic analysis. In bioscreening experiments, none of the isolated compounds showed potent antibacterial or cytotoxic activity. However, compounds 2, 3, and 7 exhibited lethality against brine shrimp (Artemia salina), with LD50 values of 7.1, 4.5, and 5.5 µM, respectively.

Aniquinazolines A-D, four new quinazolinone alkaloids from marine-derived endophytic fungus Aspergillus nidulans.

Four new quinazolinone alkaloids, namely, aniquinazolines A-D (1-4), were isolated and identified from the culture of Aspergillus nidulans MA-143, an endophytic fungus obtained from the leaves of marine mangrove plant Rhizophora stylosa. The structures of the new compounds were elucidated by spectroscopic analysis, and their absolute configurations were determined on the basis of chiral HPLC analysis of the acidic hydrolysates. The structure for 1 was confirmed by single-crystal X-ray diffraction analysis. All these compounds were examined for antibacterial and cytotoxic activity as well as brine shrimp (Artemia salina) lethality.

Triazole and dihydroimidazole alkaloids from the marine sediment-derived fungus Penicillium paneum SD-44.

A novel triazole carboxylic acid, penipanoid A (1), two new quinazolinone alkaloids, penipanoids B (2) and C (3), and a very recently reported quinazolinone derivative (4) were isolated from the marine sediment-derived fungus Penicillium paneum SD-44. Their structures were elucidated by spectroscopic analysis, and the structure for 1 was confirmed by X-ray crystallographic analysis. Compound 1 represents the first example of a triazole derivative from marine sediment-derived fungi, and compound 2 is a rare quinazolinone derivative having a dihydroimidazole ring system. The cytotoxicity of compounds 1 and 4 and the antimicrobial activity of 1-4 were evaluated.