A phytochemical investigation to obtain new NO inhibitors resulted in the identification of six new (1-6) and four known (7-10) terpenoids from Salvia plebeia. Compounds 1 and 2 are new diterpenoids, 3-5 are new meroditerpenoids, 6-9 are sesquiterpenoids, and 10 is a known meroditerpenoid. The structures of these isolates were determined by routine NMR experiments and X-ray diffraction, as well as the electronic circular dichroism spectra. Compounds 1-4 are diterpenoids carrying an oxygen bridge, and 6 is a rare copane-type sesquiterpenoid with a bridged tricyclic framework. The isolates inhibited NO generation induced by lipopolysaccharide in BV-2 cells. The possible mechanism of NO inhibition of some bioactive compounds was also investigated using molecular docking, which revealed interactions of bioactive compounds with the iNOS protein.
A phytochemical investigation of the leaves of Callicarpa macrophylla led to the isolation of five new diterpenoids (1-5), macrophypenes A-E, and nine known analogues (6-14). The structures of 1-5 were established on the basis of extensive analysis of NMR spectroscopic data, X-ray diffraction data, and experimental and calculated electronic circular dichroism spectra. Compound 1 is a spiroditerpenoid with a novel skeleton, and compound 5 is a rare ent-abietane diterpenoid possessing a peroxide bridge. Compounds 1, 5-7, and 11-14 stimulate nerve growth factor mediated neurite outgrowth from PC12 cells.
Euphorbia prolifera is a poisonous plant belonging to the Euphorbiaceae family. In this survey on plant secondary metabolites to obtain bioactive substances for the development of new antifungal agents for agriculture, the chemical constituents of the plant E. prolifera were investigated. This procedure led to the isolation of six new and two known diterpenes. Their structures, including absolute configurations, were elucidated on the basis of extensive NMR spectroscopic data analyses and time-dependent density functional theory ECD calculations. Biological screenings revealed that these diterpenes possessed antifungal activities against three phytopathogenic fungi. The results of the phytochemical investigation further revealed the chemical components of the poisonous plant E. prolifera, and biological screenings implied the extract or bioactive diterpenes from this plant may be regarded as candidate agents of antifungal agrochemicals for crop protection products.
Inula japonica belongs to the family Asteraceae, and its flowers have been used as dietary supplements and health tea in China. The study aimed to identify the bioactive components with the antiproliferative property. Ten 1,10-seco-eudesmanolide derivatives, including four new compounds (1-4), were isolated from the flowers of I. japonica. Their structures were established on the basis of the interpretation of spectroscopic data and electronic circular dichroism (ECD) calculations. All of these isolates were evaluated for their antiproliferative activities against MCF-7 and MDA-MB-231 human breast cancer cells. Compound 4 possessed the most potent effects, with the IC50 values of 0.20 ± 0.04 and 6.22 ± 1.30 μM against MCF-7 and MDA-MB-231 cells, respectively. The present investigation indicated that eudesmanolide derivatives from the flowers of I. japonica, especially compound 4, might be used as potential antitumor chemotherapy agent candidates.
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