New Rare Ent-Clerodane Diterpene Peroxides from Egyptian Mountain Tea (Qourtom) and Its Chemosystem as Herbal Remedies and Phytonutrients Agents.

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.

3-Oxo-γ-costic acid fungal-transformation generates eudesmane sesquiterpenes with in vitro tumor-inhibitory activity.

While select eudesmane sesquiterpenes exhibit anti-neoplastic activity, tumor-inhibition for costic-acids has not been established. Here biological activity of 3-oxo-γ-costic acid (1), previously isolated from Chiliadenus montanus, as well as new sesquiterpenes (2-5) and the known derivative, 3-oxoeudesma-1,4,11(13)-trien-7-1061αH-l2-oic acid (6), all produced from 1 by the fungus Athelia rolfsii, are reported. Structures were elucidated using MS and NMR spectroscopy with activity-screening utilizing human colon- and lung-tumor lines, Caco-2 and A549 respectively. Compound 1 exhibited anti-proliferative activity against Caco-2 (IC50 39µM) and 2 was active against A549 (IC50 74µM) suggesting therapeutic potential for the original substrate and a bio-transformed product.

Anti-inflammatory activity of highly oxygenated terpenoids from Achillea biebersteinii Afan.

In continuation of our chemical investigation on some medicinal plants of the genus Achillea, chromatographic investigation of the methylene chloride/methanol (1:1) extract of the air-dried aerial part of Achillea biebersteinii Afan. (family Asteraceae) afforded a new natural monoterpene (2), in addition to two known sesquiterpenes (3 and 4). Compound 1 was isolated as light needle crystals. Structures were established on the basis of MS and NMR spectroscopic (1H, 13C, 1H-1H correlation spectroscopy, heteronuclear multiple-quantum coherence and heteronuclear multiple-bond correlation) data and in case of compound 1 were confirmed by X-ray analysis. All isolated compounds were examined for their anti-inflammatory activity to inhibit lipopolysaccharide-induced NO production in RAW264.7 macrophage cells. Compounds 3 and 4 produced a promising anti-inflammatory effect (76% and 80% inhibition, respectively). However, compounds 1 and 2 produced moderate inhibition of NO release recording a 41% and 36% inhibition of NO production, respectively.

A new trans-neoclerodane diterpene from Stachys aegyptiaca.

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.

Triterpenes from Euphorbia rigida.

Phytochemical studies of the aerial parts of Euphorbia rigida afforded three triterpenes: betulin (1), cycloart-23Z-ene-3, 25-diol (2) and cycloartan-3, 24, 25-triol (3), firstly isolated from this plant. The structures and relative stereochemistry were determined on the basis of extensive spectroscopic analyses, including 1D and 2D NMR experiments (1H NMR, 13C NMR, COSY, NOESY, HMQC and HMBC).