New labdane diterpenoids from Salvia leriifolia: Absolute configuration, antimicrobial and cytotoxic activities

Fractionation of an n-hexane extract of the aerial parts of Salvia leriifolia led to the isolation of two new (1, 2) and two known (3, 4) labdane diterpenoids, together with three other known compounds. The structures were established by a combination of 1D and 2D NMR, and HRESIMS. The structures of 1 and 3 were confirmed by single-crystal X-ray analysis. The absolute configuration of 1–4 was established by electronic circular dichroism spectroscopy. Compounds 1–4 were evaluated for their cytotoxic activities against MCF-7 human breast cancer cells. Labdanes 3 and 4 were additionally tested against MDA-MB231 human breast cancer and DU-145 human prostate cancer cell lines. Compound 4 showed IC50 values of 25, 50, and 50 µM against MCF-7, MDA-MB231, and DU-145 cells, respectively. Compounds 1–4 were tested for activity against gram-positive (Staphylococcus aureus) and gram-negative (Escherichia coli) bacteria. Compound 3 showed an MIC of 213 µM against methicillin-resistant S. aureus

Manoyloxide Sesterterpenoids from <i>Salvia mirzayanii</i>

Five new manoyloxide-type sesterterpenes were isolated from aerial parts of <i>Salvia mirzayanii,</i> a species endemic to Iran. The planar structures were established by means of 1D and 2D NMR and HRESIMS. Compounds <b>1</b>–<b>3</b> differed only in their configurations at C-13 and C-14. Assignment of relative and absolute configurations was achieved by NOESY experiments and by comparison of experimental and simulated ECD spectra of possible stereoisomers. The absolute configurations of <b>4</b> and <b>5</b> were established in a similar manner

Hydrangenone, a New Isoprenoid with an Unprecedented Skeleton from <i>Salvia hydrangea</i>

Hydrangenone, a new heptacyclic isoprenoid with a 6/7/6/5/5 membered carbon ring skeleton, was isolated from the aerial parts of <i>Salvia hydrangea.</i> The structure was established by extensive NMR spectroscopic methods. The relative and absolute configuration of <b>1</b> was assigned by NOESY and X-ray crystallographic analysis and by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound <b>1</b> showed in vitro antiplasmodial activity, with an IC₅₀ value of 1.4 μM against <i>P. falciparum</i>. A plausible biosynthetic pathway of <b>1</b> was also proposed

Antitrypanosomal triterpenoid with an ε-lactone e-ring from Salvia urmiensis

A new triterpenoid, urmiensolide (1), was isolated from Salvia urmiensis. The structure was elucidated by a combination of 1D and 2D NMR, HRESIMS, and X-ray crystallographic analyses. The absolute configuration was established by comparison of experimental and simulated ECD spectra. Urmiensolide is the first pentacyclic triterpenoid bearing a ε-lactone E-ring. The compound showed in vitro antitrypanosoal activity with an IC50 value of 5.6 μM against the Trypanosoma brucei rhodesiense STIB 900 strain and a selectivity index of 33. A possible biosynthetic pathway of 1 from α-amyrin is proposed

Hydrangenone, a New Isoprenoid with an Unprecedented Skeleton from <i>Salvia hydrangea</i>

Hydrangenone, a new heptacyclic isoprenoid with a 6/7/6/5/5 membered carbon ring skeleton, was isolated from the aerial parts of <i>Salvia hydrangea.</i> The structure was established by extensive NMR spectroscopic methods. The relative and absolute configuration of <b>1</b> was assigned by NOESY and X-ray crystallographic analysis and by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound <b>1</b> showed in vitro antiplasmodial activity, with an IC₅₀ value of 1.4 μM against <i>P. falciparum</i>. A plausible biosynthetic pathway of <b>1</b> was also proposed

Triterpenoids with rare carbon skeletons from Salvia hydrangea : antiprotozoal activity and absolute configurations

Salvadione C (1) and perovskone B (2), two new triterpenoids with rare carbon skeletons, were isolated from an antiplasmodial n-hexane extract of Salvia hydrangea . The absolute configuration was determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. In vitro activity against Plasmodium falciparum K1 strain, Trypanosoma brucei rhodesiense STIB 900 strain, and cytotoxicity in rat myoblast (L6) cells were determined. Compounds 1 and 2 showed in vitro antiplasmodial activity, with IC(50) values of 1.43 and 0.18 muM and selectivity indices (SI) of 86.2 and 69.6, respectively. IC(50) values against T. brucei rhodesiense were found to be 4.33 and 15.92 muM, respectivel