Four new unsaturated aliphatic acid amides, named zanthoamides A–D (1–4), and eight known ones—tetrahydrobungeanool (5), ZP-amide A (6), ZP-amide B (7), ZP-amide C (8), ZP-amide D (9), ZP-amide E (10), bugeanumamide A (11), and (2E,7E,9E)-N-(2-hydroxy-2-methylpropyl)-6,11-dioxo-2,7,9-dodecatrienamide (12)—were isolated from the pericarps of Zanthoxylum bungeanum. The structures of these compounds were elucidated by extensive use of spectroscopic methods, including HRESIMS, 1D and 2D NMR analyses and comparison with previously reported data. Compound 4 contained a rare C6 fatty acid unit with an acetal group. Results revealed that compounds 1, 5, 6, and 12 showed inhibitory effects on nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages, with IC50values of 48.7 ± 0.32, 27.1 ± 1.15, 49.8 ± 0.38, and 39.4 ± 0.63 µM, respectively, while the other compounds were inactive (IC50 > 60 μM). They could contribute to the anti-inflammatory effects of Z. bungeanum by suppression of NO production.
Three undescribed cassane-type diterpenoids (CAs), caesalpulcherrins K-M (1–3), together with three known ones (4–6) were isolated from the aerial parts of Caesalpinia pulcherrima (L.) Sw (Fabaceae). Their structures were elucidated via analysis of NMR (1 D and 2 D) and HRESIMS data. The character for caesalpulcherrin K possessing the olefin bond at C-11 and C-12 in its cassane skeleton was observed, which belonged to a small group among more than 450 CAs. That is, only fifteen derivatives have been reported up to now, to our knowledge. Biological evaluation revealed that compounds 1–6 exhibited moderate anti-inflammatory activity, with an IC50 value from 6.04 ± 0.34 to 8.92 ± 0.65 μM. Furthermore, compounds 5 and 6 exhibited significant α-glucosidase inhibitory activity at 10 μM. Graphical Abstract
Bacillus cereus, a Gram-positive bacterium, is a food contaminant that threatens the health of thousands of people around the world. Because of the continuous emergence of drug-resistant strains, the development of new classes of bactericides from natural products is of high priority. In this study, two novel cassane diterpenoids (pulchins A and B) and three known ones (3–5) were elucidated from the medicinal plant Caesaplinia pulcherrima (L.) Sw. Pulchin A, with a rare “6/6/6/3” carbon skeleton, showed significant antibacterial activity against B. cereus and Staphylococcus aureus, with MIC values of 3.13 and 6.25 μM, respectively. Further investigation of its mechanism of antibacterial activity against B. cereus is also discussed in detail. The results revealed that the antibacterial activity of pulchin A against B. cereus may be caused by pulchin A interfering with bacterial cell membrane proteins, affecting membrane permeability and causing cell damage or death. Thus, pulchin A may have a potential application as an antibacterial agent in the food and agricultural industries.
Three new grayanane diterpenoids, pierisoids C‒E (1–3), as well as 10 known ones (4–13), were evaluated from the flowers of Pieris formosa, which is used as an insecticide in rural areas of China. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analyses. Significant antifeedant activity of 1, 3 and 10 against the beet armyworm (Spodoptera exigua) was found, indicating that these diterpenoids might also be involved in the plant defense against insect herbivores.