Chemistry of Natural Compounds最新文献

A new tetraazacyclododecane, 2-nonyl-1,4,7,10-tetraazacyclododecane (1), along with nine isoquinoline alkaloids, northalifoline (2), thalifoline (3), corydaldine (4), N-methylcorydaldine (5), oxyberberine (6), berberine (7), palmatine (8), jatrorrhizine (9), and columbamine (10) were isolated from the bark of Ilex latifolia (Aquifoliaceae). The structure of the new tetraazacyclododecane was elucidated by chemical and physical evidence.

A new chromone, 5-hydroxy-2-methoxy-6,7,8-trimethylchromone (1), along with ten known compounds including 5,7-dimethoxychromone (2), 5-hydroxy-7-methoxychromone (3), 5-hydroxychromone (4), 5,7-dihydroxy-2,6-dimethylchromone (5), 5,7-dihydroxy-2,8-dimethyl-chromone (6), 5,7-dihydroxy-2,6,8- trimethylchromone (7), (3S,4R)-4-hydroxymellein (8), (3S,4S)-4-hydroxymellein (9), 4-hydroxymethyl-3,5-dimethyldihydro-2-furanone (10), and 3,4-dihydroxy-3-methyldihydro-2-furanone (11), were isolated from the roots of Haworthia cooperi var. truncata (Asphodelaceae). The structure of the new chromone derivative was elucidated by chemical and physical evidence.

Progress during the period 2016–2024 on the synthesis and transformations of A-seco-triterpene derivatives is reviewed and analyzed. Information on their pharmacological potential is given.

A novel glycoside compound, 3-hydroxy-5-(β-D-glucopyranosyloxy)-hexanoic acid (1) has been isolated from the fruits of Aronia melanocarpa (Michx.) Britton, along with ten known compounds, vanillic acid 4-O-β-D-glucoside (2), (R)-4-O-β-D-glucopyranoyl-4-hydroxy-2-pentanone (3), (6R,9R)-roseoside (4), phloroacetophenone 2-O-glucoside (5), methyl (3S,5S)-5-hydroxy-3-(β-D-glucopyranosyloxy)hexanoate (6), β-D-glucopyranosyl benzoate (7), parasorboside (8), benzyl 6-O-α-L-arabinofuranosyl-β-D-glucoside (9), dihydrophasmaric acid 4′-O-β-D-glucopyranoside (10), and 4-O-β-D-glucopyranosyl-cis-p-coumaric acid (11). The structure of compound 1 was determined by NMR spectroscopic and MS analyses. Compounds 1–4 showed antibacterial activity against Staphylococcus aureus RN (4220).

The glucoarabinogalactan GAG-Sco with MM 15 kDa was obtained by fractionation of water-soluble polysaccharides from Scutellaria comosa Juz. An analysis of the monosaccharide residues showed that GAG-Sco consisted of arabinose (35.7%), glucose (25.8%), and galactose (27.7%). Chemical analyses and ¹H and ¹³C NMR spectroscopic data found that the main chain of the GAG-Sco macromolecule consisted of 1,6-bound D-galactopyranosyl residues. A side chain in the C-2 position contained glucose, arabinose, and the oligosaccharide fragment α-Araf-(5→1)-α-Araf. The water-soluble polysaccharide from S. comosa was shown to affect phagocytosis, specifically the phagocytic index of neutrophils.

A previously unreported acyclic monoterpene, zanthungeanumol A (1), and eleven known alkaloids 2–12 were isolated from the pericarps of Zanthoxylum bungeanum. The activity evaluation showed that compound 7 exhibited potent antibacterial activities against Staphylococcus aureus, while compound 8 exhibited significant antimicrobial activity against Escherichia coli 140 with a MIC value of 6.25 μg/mL, and their activities were comparable to the plant-derived antibacterial drug berberine.

N-Substituted derivatives of the alkaloid (–)-cytisine and its thioanalogue were synthesized via a two-step ‘alkylation-thionation’ chemical transformation sequence. The ability of the obtained compounds to inhibit metabolic activity of conditionally normal (HEK293, human embryonic kidney cells) and cancerous cells (A549, lung adenocarcinoma; MCF-7, breast cancer) was assessed. It was found that N-hexyl-, -nonylcytisine and N-heptyl-, -octyl-, -nonyl- and -benzyl-thiocytisine demonstrated moderate cytotoxic properties. The hit-compound (1R,5S)-3-benzyl-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocine-8- thione (22) was identified with IC₅₀ values of 12.83 ± 1.2 μM (A-549) and 35.75 ± 7.43 μM (MCF-7). It was shown that the antiproliferative properties of compound 22 might be associated with alterations of cell cycle regulation in tumor cells (A549 and MCF-7), exhibiting mainly cytostatic effect, whereas in conditionally normal cells (HEK293), 22 promotes apoptosis, thus triggering the cytotoxic mechanisms.