New Meroterpenoids from <i>Aspergillus terreus</i> with Inhibition of Cyclooxygenase‑2 Expression

Two novel meroterpenoids, yaminterritrems A (<b>1</b>) and B (<b>2</b>), were isolated from <i>Aspergillus terreus</i> collected from hot spring zones in Yang-Ming Mountain, Taiwan, and cultured at 40 °C. The structures of <b>1</b> and <b>2</b> were elucidated by NMR, MS spectral and X-ray crystallographic analyses. The biosynthetic route for <b>1</b> and <b>2</b> involving the conversion of the sesquiterpene with phenyl-α-pyrone is proposed. Besides, <b>2</b> exhibited a dose-dependent inhibitory effect on COX-2 expression in LPS-stimulated RAW264.7 macrophages

Anti-inflammatory Flavonoids from the Rhizomes of <i>Helminthostachys zeylanica</i>

Eight new prenylated flavonoids, ugonins M−T (1-8), together with five known compounds, ugonins J−L (9−11), 5,4′-dihydroxy-4′′,4′′-dimethyl-5′′-methyl-5′′H-dihydrofurano[2′′,3′′:6,7]flavanone, and quercetin, were isolated and purified from the rhizomes of Helminthostachys zeylanica. The structures of the new isolates were elucidated by spectroscopic and chemical methods. Compounds 1, 3, 5, 7, 8, and 11 showed inhibition of superoxide anion generation and elastase release by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (FMLP/CB)

Anti-inflammatory Flavonoids from the Rhizomes of <i>Helminthostachys zeylanica</i>

Eight new prenylated flavonoids, ugonins M−T (1-8), together with five known compounds, ugonins J−L (9−11), 5,4′-dihydroxy-4′′,4′′-dimethyl-5′′-methyl-5′′H-dihydrofurano[2′′,3′′:6,7]flavanone, and quercetin, were isolated and purified from the rhizomes of Helminthostachys zeylanica. The structures of the new isolates were elucidated by spectroscopic and chemical methods. Compounds 1, 3, 5, 7, 8, and 11 showed inhibition of superoxide anion generation and elastase release by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (FMLP/CB)

Asperjinone, a Nor-Neolignan, and Terrein, a Suppressor of ABCG2-Expressing Breast Cancer Cells, from Thermophilic <i>Aspergillus terreus</i>

Breast cancer cells express ABCG2 transporters, which mediate multidrug resistance. Discovering a novel compound that can suppress ABCG2 expression and restore drug sensitivity could be the key to improving breast cancer therapeutics. In the current work, one new nor-neolignan, asperjinone (<b>1</b>), as well as 12 other known compounds, was isolated from <i>Aspergillus terreus</i>. The structure of the new isolate was determined by spectroscopic methods. Among these isolates, terrein (<b>2</b>) displayed strong cytotoxicity against breast cancer MCF-7 cells. Treatment with terrein (<b>2</b>) significantly suppressed growth of ABCG2-expressing breast cancer cells. This suppressive effect was achieved by inducing apoptosis via activating the caspase-7 pathway and inhibiting the Akt signaling pathway, which led to a decrease in ABCG2-expressing cells and a reduction in the side-population phenotype