Seven flavonoids have been isolated from the aerial parts of Halostachys caspica C. A. Mey. (Chenopodiaceae) for the first time. By means of physicochemical and spectrometric analysis, they were identified as luteolin (1), chrysin (2), chrysin 7-O-β-D-glucopyranoside (3), quercetin (4), quercetin 3-O-β-D-glucopyranoside (5), isorhamentin-3-O-β-D-glucopyranoside (6), and isorhamentin-3-O-β-D-rutinoside (7). All flavonoids were evaluated to show a broad antimicrobial spectrum of activity on microorganisms including seven bacterial and one fungal species as well as pronounced antioxidant activity. Among them, the aglycones with relatively low polarity had stronger bioactivity than their glycosides. The results suggested that the isolated flavonoids could be used for future development of antimicrobial and antioxidant agents, and also provided additional data for supporting the use of H. caspica as forage.
Three steroids and one nordammarane triterpenoid were isolated for the first time from the endophytic fungus Pichia guilliermondii Ppf9 derived from the medicinal plant Paris polyphylla var. yunnanensis. By means of physicochemical and spectrometric analysis, they were identified as ergosta-5,7,22-trienol (1), 5α,8α-epidioxyergosta-6,22-dien-3β-ol (2), ergosta-7,22-dien-3β,5α,6β-triol (3), and helvolic acid (4). Both micro-dilution-colorimetric and spore germination assays were employed to evaluate their antimicrobial activity. Among them, helvolic acid (4) exhibited the strongest antibacterial activity against all test bacteria, with MIC values ranging from 1.56 µg/mL to 50 µg/mL, and IC50 values from 0.98 µg/mL to 33.19 µg/mL. It also showed strong inhibitory activity on the spore germination of Magnaporthe oryzae with an IC50 value of 7.20 µg/mL. Among the three steroids, 5α,8α-epidioxyergosta-6,22-dien-3β-ol (2) exhibited relatively strong antimicrobial activity. The results suggest that the endophytic fungus Pichia guillermondii Ppf9 could be a candidate for producing helvolic acid, and the metabolites from this fungus could be potentially developed as antimicrobial agents in the future.
Nine new spirobisnaphthalenes, palmarumycins B1-B9 (1-9), along with 13 known compounds (10-22), were isolated from cultures of the fungus Berkleasmium sp., an endophyte isolated from the medicinal plant Dioscorea zingiberensis C. H. Wright. The structures of the new compounds were elucidated by analysis of the 1D and 2D NMR and HRESIMS spectra and by comparison with known compounds. Compounds 7-9 contain an uncommon 2,3-dihydro-1H-inden-1-one unit. All isolated compounds were evaluated for their antibacterial activities against Bacillus subtilis, Staphylococcus hemolyticus, Agrobacterium tumefaciens, Pseudomonas lachrymans, Ralstonia solanacearum, and Xanthomonas vesicatoria and for their antifungal effects against the spore germination of Magnaporthe oryzae. Palmarumycin C8 (22) exhibited the best antibacterial and antifungal effects. In addition, diepoxin δ (11) and palmarumycin C8 (22) showed pronounced cytotoxic activities against five human cancer cell lines (HCT-8, Bel-7402, BGC-823, A 549, A 2780) with IC50 values of 1.28-5.83 μM.
Five new sesquiterpene polyol esters were isolated from the root bark of Celastrus angulatus by bioassay-guided fractionation. Their structures were determined by spectral data interpretation as 1alpha,2alpha,6beta,8beta,13-pentaacetoxy-9beta-benzoyloxy-4beta-hydroxy-beta-dihydroagarofuran (1), 1alpha,2alpha,6beta-triacetoxy-8alpha-(beta-furancarbonyloxy)-9beta-benzoyloxy-13-isobutanoyloxy-4beta-hydroxy-beta-dihydroagarofuran (2), 1alpha,2alpha,6beta-triacetoxy-8beta-isobutanoyloxy-9beta-(beta-furancarbonyloxy)-13-(alpha-methyl)butanoyloxy-4beta-hydroxy-beta-dihydroagarofuran (3), 1alpha,2alpha,6beta-triacetoxy-8alpha,13-diisobutanoyloxy-9beta-benzoyloxy-4beta-hydroxy-beta-dihydroagarofuran (4), and 1alpha,2alpha,6beta-triacetoxy-8alpha-isobutanoyloxy-9beta-benzoyloxy-13-(alpha-methyl)butanoyloxy-4beta-hydroxy-beta-dihydroagarofuran (5). Compounds 1-5 exhibited insecticidal activity against the larval of Mythimna separata.
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