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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&ndash, 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.

Two new E/Z neo-clerodane diterpene isomers, trivially named stachaegyptin D (1) and E (2), together with known compounds, stachysolon monoacetate (3) and stachysolon diacetate (4), were isolated from an organic-solvent extract of the medicinal herb Stachys aegyptiaca. Structures were elucidated by a combination of spectroscopic methods, including HREIMS, 1H, 13C, DEPT, and 2D NMR analysis, as well as, first time X-ray analysis for stachysolone (3). All isolated metabolites showed some activity against the human hepatocellular cell line, HepG2. Compound 4 was the most active with an IC50 of 59.5 μM.

Phytochemical investigation of Stachys aegyptiaca resulted in the characterization of three new diterpenes (1-3) together with eleven known compounds including four neo-clerodane diterpenes and seven flavonoid aglycones. Structure elucidation was performed by spectroscopic analysis by HRFABMS, 1D and 2D NMR and X-ray. Isolated compounds were screened for anti-inflammatory activity using a lipopolysaccharide-induced nitric oxide inhibition assay employing murine macrophage cells. Among the assayed compounds, 13 (calycopterin) showed a concentration-dependent inhibition of LPS-induced nitric oxide release with a IC50 of 62.5 μM.

Phytochemical investigation of the methylenechloride/methanol extract of the aerial parts of Stachys aegyptiaca afforded a new neoclerodane-type diterpene with a new side chain 1, in addition to two known diterpenes 2 and 3 and a known flavonoid glycoside 4. The structures of the compounds were determined by comprehensive NMR studies including DEPT, COSY, NOESY, HMQC, HMBC and HR-MS.

Background and objectives Stachys aegyptiaca Pers. (family Lamiaceae) is a perennial aromatic wild plant collected from Saint Catherine Protectorate, Sinai. The essential oil of S. aegyptiaca was obtained using two different techniques, conventional hydrodistillation (HD) and microwave-assisted extraction (MAE). The aim of the present study was to compare the effect of the two techniques on oil yield and oil composition. MAE offered reduction in the extraction time with better oil yield compared with HD. Materials and methods Two different techniques, conventional HD and MAE, were used for the extraction of essential oil from S. aegyptiaca. The chemical composition of the essential oil was analyzed using the gas chromatography–mass spectrometry technique. Results and conclusion Gas chromatography–mass spectrometry of the essential oils obtained revealed the presence of 48 and 30 components constituting 99.31 and 99.82% of the total composition of the oils obtained using; MAE and HD, respectively. Variations in the percentage yield and chemical composition were observed. The major component found in the extracted oils was α-pinene (24.65% HD and 41.14% MAE). MAE offered reduction in the extraction time (60 min vs. 3 h) with better oil yield (1.4% w/v) when compared with HD (0.9% w/v). MAE could be used as an alternative tool for the isolation of essential oils from their natural sources.

Aerial parts of Stachys aegyptiaca contain the unique acylated flavonoid, diapigenin-7- O -(6″- trans ,6″- cis - p , p ′-dihydroxy- μ -truxinyl) glucoside , stachysetin, and the hitherto unknown, apigenin 7- O -(3″- p -coumaryl) glucoside . In addition, the known compounds, apigenin 7- O -(6″- p -coumaryl) glucoside and naringenin were also identified. Structures were established by conventional methods of analysis and confirmed by 1 H, 13 C NMR and mass spectral analysis. 2D-chemical shift correlation NMR was also used in the case of the new flavonoids.

In addition to 5,7,3′-trihydroxy-6,4′-dimethoxyflavone, 5,7,3′-trihydroxy-6,8,4′-trimethoxyflavone, isoscutellarein, luteolin, and luteolin-7-O-glucoside, the methanol extract of the aerial parts of Stachys aegyptiaca yielded a new flavone identified as luteolin 3′,4′-dimethylether-7-O-β-D-glucoside on the basis of chemical and spectroscopic methods.

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.