Two new compounds, ardisiapunine B (1) and ardisiapunine C (2), were isolated from Ardisia lindleyana D. Dietr. Their structures were examined using HR–ESI–MS, IR, (1D, 2D) NMR spectroscopic analyses, single–crystal X–ray diffraction, and ECD calculation. It was found that the two new compounds belong to unusual oleanane-type triterpenes, with compound 1 bearing an acetal unit and a C–13–C–18 double bond, and compound 2 bearing a C–28 aldehyde group and a C–18–C–19 double bond. The anti-inflammatory properties of compounds 1 and 2 were tested on NO production and cellular morphology using RAW264.7 cells, and their anti-tumor properties were tested on cytotoxic activities, cellular morphology, cell apoptosis, and cell cycle. The results showed that compound 1 exhibited a potent cytotoxicity against HepG2 cell lines with an IC50 of 12.40 μM. Furthermore, it is possible that compound 1 inhibits cell proliferation by blocking the cell G2/M phase and promoting cell apoptosis. Compound 2 exhibited a potential anti-inflammatory activity by decreasing the production of NO in LPS–stimulated RAW264.7 cells. Comparative analysis of the structures of compounds 1 and 2 revealed that the acetal structure and double bond positions were the main differences between them, and these are presumed to be the main reasons for the extreme differences in their cytotoxicity and anti-inflammatory activities. From these new findings, two promising lead compounds were identified for the future development of potential anti–inflammatory or anti–tumor agents.
Two new sulfur glycosides, bursapastoris A–B (3–4), were extracted and isolated from shepherd’s purse seed, along with two new natural products, 11-(methylsulfinyl)undecanoic acid (2) and 10-(methylsulfinyl)decanoic acid (1). Their structures were determined though infrared spectroscopy, one-dimensional nuclear magnetic resonance (1H and 13C), and electrospray ionization mass spectrometry. Additionally, the structures of 3–4 were further identified by two-dimensional nuclear magnetic resonance (HMBC, HSQC, 1H-1H COSY, and NOESY). Compounds 1–4 showed relatively favorable docking to NF-κB. Unfortunately, we only discovered that compound 1–4 had weak anti-radiation activity at present. Therefore, further research regarding the biological activity of these organosulfur compounds is required at a later stage.
Alkaloids are a material treasure bestowed on humans by nature owing to their numerous biological activities. Orychophragine D, an alkaloid isolated from the seeds of Orychophragmus violaceus was identified as bearing a novel skeleton and proved to have an excellent radioprotective effect. Different from the common alkaloid structure, the main block of orychophragine D is constructed of an oxotriazine and an oxopiperazine, which are connected in parallel by a C-N bond. In this paper, a preparation method for the novel heterocycle skeleton of orychophragine D is proposed for the first time. N-Boc-L-serine was utilized as the original material to complete the preparation with 11 steps in a 13% overall yield. A hydroxyl group was established on the side chain of the skeleton as the reaction site for researchers to conduct further structural modification or derivatization.
Compounds containing sulfur are the primary components of anti-radiation drugs and represent a key focus in the innovative design and discovery of pharmaceuticals. The adverse effects of synthetic sulfur-containing radiation protective agents are significant concerns that cannot be overlooked. It is imperative to identify natural sulfur compounds that exhibit low toxicity and high efficacy as radiation protection agents. Cruciferous plants demonstrate notable resistance to ionizing radiation. The literature review revealed that Lepidii semen and Descurainiae semen, both of which are rich in sulfur compounds and the PI3K/AKT signaling pathway regulates radiation-induced oxidative stress, inflammation, and apoptosis. We speculate that the sulfur compounds of the Lepidii semen and Descurainiae semen may exert radiation protection by regulating the PI3K/AKT signaling pathway, and this hypothesis was supported by molecular docking analysis. The sulfur compounds (glucotropaeolin, gluconapin, glucoiberverin, glucocappasalin, tropeolin, etc.) demonstrate greater potential.