Minimalist Natural ORPphilin Macarangin B Delineates OSBP Biological Function.

OSBP ligands from the ORPphilin family are chemically complex natural products with promising anticancer properties. Here, we describe macarangin B, a natural racemic flavonoid selective for OSBP, which stands out from other ORPphilins due to its structural simplicity and distinct biological activity. Using a bioinspired strategy, we synthesized both (,,) and (,,)-macarangin B enantiomers, enabling us to study their interaction with OSBP based on their unique optical properties.

Secondary metabolites from marine fungus Penicillium chrysogenum VH17 and their antimicrobial and cytotoxic potential.

One new compound, methyl 3-((1-((2-carbamoylphenyl)amino)-1-oxopropan-2-yl)amino)-3-oxopropanoate (1), along with 9 known secondary metabolites (2-10) were isolated and elucidated chemical structures from the methanol extract of the marine-derived fungus Penicillium chrysogenum VH17. Subsequent bioassays showed the antimicrobial and cytotoxic potential of the isolated compounds. All compounds 1-10 displayed antimicrobial effects against at least one tested reference microorganism with MIC values ranging from 32 to 256 µg mL-1.

Antimicrobial and Cytotoxic Secondary Metabolites from a Marine-Derived Fungus Penicillium Citrinum VM6.

Investigation of an antimicrobial and cytotoxic ethyl acetate extract prepared from solid fermentation of the marine-derived fungus Penicillium citrinum VM6 led to the isolation of eight metabolites (1-8), including one citrinin dimer dicitrinone F (1). Of these, compound 7 was isolated for the first time from the Penicillium genus and compound 1 with carbon-bridged C-7/C-7' linkage is rarely reported. All compounds (1-8) exhibited selective antimicrobial activity against the tested Gram-positive bacteria and Candida albicans with MICs of 32-256 µg/mL.

Structure-Based Design of a Lead Compound Derived from Natural Schweinfurthins with Antitumor Properties That Target Oxysterol-Binding Protein.

Schweinfurthins (SWs) are naturally occurring prenylated stilbenes with promising anticancer properties. They act through a novel mechanism of action similar to that of other families of natural compounds. Their known target, oxysterol-binding protein (OSBP), plays a crucial role in controlling the intracellular distribution of cholesterol.

A Pair of Undescribed Alkaloid Enantiomers from Marine Sponge-Derived Fungus Hamigera avellanea and Their Antimicrobial and Cytotoxic Activities.

From marine sponge-associated fungus Hamigera avellanea, thirteen secondary metabolites including a pair of undescribed alkaloid enantiomers (+)-hamiavemin A (4S) (+)-1 and (-)-hamiavemin A (4R) (-)-1. Compound 1 was enantiomers resolved by the Chiralpak AS-3 column, using a hexane/isopropanol mobile phase. Their structures were determined based on extensive analyses of HR-ESI-MS, 1D and 2D NMR spectra.

A new cytotoxic compound from the leaves of Guillaumin.

New propene derivative 1-(3,4-methylenedioxyphenyl)-2-(2-hydroxy-5-(3-hydroxypropyl)-3-methoxyphenyl)prop-2-en-1-one (), along with three known triterpenoids ursolic acid (), pomolic acid (), and maslinic acid () were isolated from the leaves of species. All structures were assigned by spectroscopic analysis. Compound showed potent cytotoxicity against four cancer cell lines (KB, HepG2, Lu, and MCF7) with the IC values of 3.

Cytotoxic Prenylated Stilbenes Isolated from Macaranga tanarius.

With the aim of discovering new cytotoxic prenylated stilbenes of the schweinfurthin series, Macaranga tanarius was selected for detailed phytochemical investigation among 21 Macaranga species examined by using a molecular networking approach. From an ethanol extract of the fruits, seven new prenylated stilbenes, schweinfurthins K-Q (7-13), were isolated, along with vedelianin (1), schwenfurthins E-G (2-4), mappain (5), and methyl-mappain (6). The structures of the new compounds were established by spectroscopic data analysis.