Abstract
Genus Stachys, the largest genera of the family Lamiaceae, and its species are frequently used as herbal teas due to their essential oils. Tubers of some Stachys species are also consumed as important nutrients for humans and animals due to their carbohydrate contents. Three new neo-clerodane diterpene peroxides, named stachaegyptin F-H (1, 2, and 4), together with two known compounds, stachysperoxide (3) and stachaegyptin A (5), were isolated from Stachys aegyptiaca aerial parts. Their structures were determined using a combination of spectroscopic techniques, including HR-FAB-MS and extensive 1D and 2D NMR (1H, 13C NMR, DEPT, 1H-1H COSY, HMQC, HMBC and NOESY) analyses. Additionally, a biosynthetic pathway for the isolated compounds (1–5) was discussed. The chemotaxonomic significance of the isolated diterpenoids of S. aegyptiaca in comparison to the previous reported ones from other Stachys species was also studied.
Highlights
The genus Stachys has about 300 species growing wild in the temperate and tropical regions throughout the world except the continent of Australia and New Zealand [1]
Compound 1 was isolated as a colorless oil with an optical rotation of [α]25
Its molecular formula C20 H30 O4 was determined from the high-resolution FAB-MS analysis with a molecular ion peak [M + Na]+ at m/z 357.2045, indicating six degrees of unsaturation
Summary
The genus Stachys (woundwort) has about 300 species growing wild in the temperate and tropical regions throughout the world except the continent of Australia and New Zealand [1]. The genus Stachys is rich with flavonoids and phenolic [17,31,32,33,34,35,36], diterpenoids [10,21,27,37,38,39,40,41,42], iridoids [20,43,44,45], and phenylethanoid glycosides [46,47] metabolites. We report the isolation and structural determination of further three new ent-neo-clerodane diterpene peroxides, named stachaegyptin F-H (1, 2, 4), as well as two known compounds, stachysperoxide (3) and stachaegyptin A (5) (Figure 1), from the aerial parts of this species using extensive 1D and 2D NMR and HR-FAB-MS analyses.
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