Chemistry of Natural Compounds最新文献

A series of abietic acid derivatives modified with a triazole moiety at the C-18 position were synthesized using Huisgen 1,3-dipolar cycloaddition reaction of 18-azidoabietane with alkynes. The antitumor activity of the synthesized compounds was investigated through human cervical cancer cells (HeLa), human breast cancer cells (MCF-7) and human renal epithelial cells (HEK-293T). The outcome indicated that compounds 5e, 5f, 5j exhibited positive inhibitory activity against the tested tumor cell lines. In particular, the IC₅₀ value for the inhibitory activity of compound 5e against human breast cancer cells (MCF-7) was 11.2 μmol/L.

Studies of two Anthriscus (Apiaceae) species, A. sylvestris (L.) Hoffm. and A. nemorosa Spreng. [syn. A. sylvestris subsp. nemorosa (M. Bieb.) C. Y. Wu & F. T. Pu] led to the isolation of 11 compounds, including three new flavonoids 1–3. The structures of the new compounds were established as apigenin 7-(2′′-O-caffeyl-6′′-O-p-coumaroyl)-O-β-D-glucopyranoside (anthriscoside A, 1), apigenin 7-(4′′-O-caffeyl-6′′-O-p-coumaroyl)-O-β-D-glucopyranoside (anthriscoside B, 2), and luteolin 7-(2′′,6′′-di-O-malonyl)-O-β-D-glucopyranoside (anthriscoside C, 3). Compounds 1–3 possessed antiradical activity.

Trichoderma spirale is an endophytic fungus with diverse biological activities, including bioherbicidal effects through photosynthesis inhibition in weeds. This study investigated the metabolome of T. spirale using mass spectrometry data dereplication via a molecular networking approach. The metabolites identified include isolongifolol, curcumol, L-leucyl-L-proline lactam, azelaic acid, and 2-hydroxyisocaproic acid. Thus, this work represents a significant contribution to the study of the T. spirale metabolome, revealing for the first time the presence of 27 metabolites in this species, including eight previously known metabolites of the Trichoderma genus.

New derivatives of maleopimaric acid containing phenylthioureide fragments were synthesized. The antioxidant activity of 24 maleopimaric acid derivatives in the 2- and 6-positions was studied in three in vitro models, i.e., FRAP, reduction of DPPH radical, and reduction of ABTS radical. Methyl-, 2-isonicotinoyl-, and 2-(pyridin-3-ylcarbonyl)hydrazinocarbonothioyl derivatives of 2-allylmaleopimarimide showed antioxidant activity in vitro in the ABTS model comparable to the reference drug ascorbic acid and superior than that of Trolox.

A method for modifying ring A of isoalantolactone to produce 4(R)-hydroxy-15-triazolyl derivatives was developed. The key steps in the transformation included sequential azidolysis of 13-methoxy-4,15-epoxy- 11,13-dihydroisoalantolactones and Cu-catalyzed azide-alkyne cycloaddition with various alkynes. A retro-Michael reaction of (11R)- and (11S)-stereoisomeric (4R)-hydroxy-13-methoxy-15-triazolyl-11,13- dihydroisoalantolactones using cesium carbonate in DMF formed isoalantolactone derivatives. The structures of three compounds were established by X-ray crystal structure analyses.

Reactions of the alkaloid anabasine with benzene-, p-toluene-, o-methoxyphenyl-, 3,4-dimethylbenzene-, 2,4,6-trimethylbenzene-, and m-nitrophenylsulfonyl chlorides under relatively mild conditions afforded the corresponding N-arylsulfonyl anabasines in good yields. Results of in vitro antimicrobial tests showed that the compounds did not exhibit antibacterial effects against microorganism strains.