Records of Natural Products

A new γ-butenoid, (Z)-6-acetylsphaerodol (2), along with seven known compounds, (4E)-7-benzoyloxy-6-hydroxy-2,4-heptadien-4-olide (1), (6S)-melodorinol (3), (6S)-acetylmelodorinol (4), (Z)-sphaerodiol (5), (Z)-7-acetylsphaerodol (6), dichamanetin (7), and pinocembrin (8), were isolated and structurally elucidated from Uvaria siamensis growing in Thailand. Their chemical structures were assigned by extensive spectroscopy (NMR and HRESIMS), as well as comparisons with the previous literature. Compounds 1-8 were evaluated for the antimicrobial activity against two multidrug-resistant Staphylococcus aureus strains, 23Sa1 and SA-ATCC. Compounds 4 and 6 displayed moderate activity with inhibitory zones of 13 and 12 mm against 23Sa1 and SA-ATCC strains, respectively. Compounds 3 and 7 exhibited significant efficacy, displaying IC50 values of 157.7 and 94.2 µM, respectively, against α-glucosidase. According to the docking data, compounds 3 and 7 have a greater influence on binding contacts with the α-glucosidase active pocket, thereby affecting the inhibitory activity of the enzyme.

This study aimed to isolate a novel limonoid compound, (6R,7S, 8R, 9R, 10R, 11R, 13S, 17R)-17-(furan-3-yl) -4, 4, 8, 10, 13-pentamethyl-3-oxo-4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 16, 17-dodecahydro-3H-cyclopenta[a]phenanthrene-6,7,11-triyltriacetate (11α-acetoxydysobinin) (1), and 3 pre-existing limonoids, namely dysobinin (2), dysobinol (3), and 7-deacetylepoxyazadiradione (4) from the seeds of Chisocheton macrophyllus (Meliaceae). In addition, the structure of the isolated compounds was determined using various spectroscopic techniques, including UV, IR, HRTOFMS, 1D, and 2D NMR. The cytotoxic effects of each compound were then evaluated against breast cancer cells of the Michigan Cancer Foundation-7 (MCF-7), but no significant activity was observed.

There are seven species in the genus Nageia, a member of the Podocarpaceae family; five are found in China. They are primarily found in eastern and southern Asia, close to the equator at the 30th parallel north and south, and in coastal mountainous areas and islands in the western Pacific. These herbs are extremely valuable for medicinal purposes. The three species of Nageia that are the subject of most current research on their chemical composition and pharmacological properties are N. nagi, N. fleuryi, and N. wallichiana. There are currently 232 known chemical components, which include steroids, flavonoids, sesquiterpenoids, and diterpenoids. Of these, 86 diterpenoid dilactones comprise most of the chemical components, and only plants of the Nageia genus contain C-ring decarbonized diterpenoid dilactones. These plants exhibit promising pharmacological activities such as anti-tumor, antioxidant, antibacterial, and anti-inflammatory properties. For the first time, an in-depth and systematic evaluation of the chemical constituents and pharmacological properties of plants in the Nageia genus is presented in the this article. This theoretical framework will help in the future investigation and development of medicinal resources and active ingredients within the genus.