HPPO-Derived Meroterpenoids from the Marine-Derived Fungus Penicillium sp. SCSIO 41691.

Seven new 4-hydroxy-6-phenyl-2H-pyran-2-one (HPPO) derived meroterpenoids, 1-methyl-12a,12b-epoxyarisugacin M (1), 1-methyl-4a,12b-epoxyarisugacin M (2), 2,3-dihydroxy-3,4a-epoxy-12a-dehydroxyisoterreulactone A (3), 2-hydroxy-12a-dehydroxyisoterreulactone A (4), 3'-demethoxyterritrems B' (5), 4a-hydroxyarisugacin P (6), and 1-epi-arisugacin H (7), together with two known analogues (8 and 9), were isolated from the marine-derived fungal strain Penicillium sp. SCSIO 41691. Their structures were elucidated by spectroscopic methods, and the absolute configurations of compounds 1 and 3 were determined by single-crystal X-ray diffraction. Among them, 1 and 2 had a unique methyl migration in the basic meroterpenoid skeleton with a 12a,12b-epoxy or 4a,12b-epoxy group, and 3 was a highly oxygenated HPPO-derived meroterpenoid featuring a rare 6/5/6/6/6/6 hexacyclic system with a 3,4a-epoxy group. Biologically, 5 exhibited inhibitory activity against lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells with an IC50 value of 21 µM, more potent than the positive control indomethacin.

Biotransformation of Glaucic Acid Isolated from the Root of Lindera glauca by the Endophytic Fungi Penicillium Chrysogenum SHJ-07.

Glaucic acid isolated from the root of Lindera glauca, was investigated by the biotransformation methods via the endophytic fungi, resulting in the production of five new glausesquiterpenes A‒E (1‒5), along with a known analogue 6. Their structures were elucidated based on spectroscopic methods and electronic circular dichroism (ECD) calculations. In the bioassays, glausesquiterpene A (1) showed good inhibitory activity of NO production in LPS-activated RAW 264.7 macrophages with an IC50 value of 20.1 µM than positive control (Indomethacin, IC50 24.1 µM). Further in vitro studies demonstrated that glausesquiterpene A significantly suppressed the protein expression of iNOS and COX-2 at the concentration of 25.0 µM.

In vitro and in vivo synergistic inhibition of Malassezia furfur targeting cell membranes by Rosa rugosa Thunb. and Coptidis Rhizoma extracts.

Background: Malassezia furfur (M. furfur) is a prevalent dermatophyte that significantly impairs patients' quality of life. This study aimed to evaluate the synergistic antifungal effects of combined extracts from Rosa rugosa Thunb. (MG) and Coptidis Rhizoma (HL) against M. furfur, both in vitro and in vivo. Methods: High-performance liquid chromatography (HPLC) was used to identify the major active compounds present in MG and HL. The antifungal activity of the combined Meilian extract (ML) was assessed using the checkerboard method and time-kill curves. Microstructural alterations in the fungi were observed using scanning electron microscopy (SEM) and transmission electron microscopy (TEM). The impact of the extracts on the fungal cell membrane was investigated through propidium iodide staining, protein concentration assays, and ergosterol quantification. Transcriptomic analysis was conducted to elucidate the molecular mechanisms underlying the effects of the extracts. Furthermore, the synergistic antifungal effects of ML were evaluated in a mouse model of seborrheic dermatitis induced by M. furfur. Results: The study demonstrated that the combined application of MG and HL significantly affected the integrity of the M. furfur cell membrane and potentially modulated its formation processes. In the M. furfur-induced seborrheic dermatitis model, ML exhibited synergistic antifungal effects and effectively alleviated skin inflammation. These findings provide an important theoretical basis for understanding the antifungal mechanisms of ML and its potential application in dermatological therapy.

Glasesterterpenoids A-C: three sesterterpenoids with 7-cyclohexyldecahydronaphthalene carbon skeleton isolated from the root of Lindera glauca.

Three novel sesterterpenoids glasesterterpenoids A-C (1-3), featuring an unprecedented 7-cyclohexyldecahydronaphthalene carbon skeleton, were isolated from the root of Lindera glauca (L. glauca). Their structures were elucidated by quantum chemical calculations and spectroscopic methods. The biogenetic pathway for 1-3 is proposed. In the bioassay, glasesterterpenoid C exhibited DNA topoisomerase 1 (Top1) inhibitory activity compared with the positive control, camptothecin. These findings represent the first examples of sesterterpenoids with a 7-cyclohexyldecahydronaphthalene carbon skeleton from the root of L. glauca.

Novel 6/7/6 ring system diterpenoids and cytochalasins from the fungus Eutypella scoparia GZU-4-19Y and their anti-inflammatory activity.

Two new compounds eutyditerpenoid A (1) and seco-phenochalasin B (5), together with seven known compounds diaporthein A (2), aspergillon A (3), phenochalasin B (4), cytochalasins Z24 and Z25 (6 and 7), scoparasins A and B (8 and 9) were isolated from marine-derived Eutypella scoparia GZU-4-19Y. Among them, eutyditerpenoid A (1) with a rare 6/7/6 ring system possesing an anhydride moiety was the first example in the pimarane-type diterpenoids. Their structures were determined based on spectroscopic methods and the electronic circular dichroism (ECD) calculations. In the bioassays, all of the isolates were evaluated for their inhibitory activity against NO production induced by lipopolysaccharide in RAW 264.7 cells. Compounds 3 and 7 showed potent NO inhibition activity with IC50 values of 2.1 and 17.1 µM respectively, and the former also significantly suppressed the protein expression of iNOS and COX-2 at the concentration of 2.5 µM.