Hesham S. M. Soliman

Cembranoid diterpenes and a briarane diterpene from corals

Two new cembrane diterpenes (+)-polydactylide (1) and (+)-7α,8β-dihydroxydeepoxysarcophine (2) together with (+)-sarcophine (3) and (+)-sarcophytoxide (4) have been isolated from the soft coral Sinularia polydactyla. The new cembrane diterpene (−)-7β-hydroxy-8α-methoxydeepoxysarcophine (5) has been obtained from the soft coral Sarcophyton trocheliophorum and the known briarane diterpene briaexcavatolide W (6) from the gorgonian coral Briareum sp. The structures were determined primarily by NMR spectroscopy. The assignment of NMR signals was performed by means of 1H–1H COSY, ROESY, HMQC and HMBC experiments.

Evaluation of immunomodulatory effect of three herbal plants growing in Egypt.

A group of medicinal plant including Silene (Silene nocturna), Black seed (Nigella sativa) and Chamomile (Matricaria chamomilla) growing in Egypt were examined for their immunomodulatory effect in Balb/c mice. Treatment (intraperitoneal injection) with five doses of methanolic extract for each plant was found to enhance the total white blood cells count (up to 1.2 × 104 cells/mm3). Bone marrow cellularity also increased significantly (P < 0.01) after the administration of the extract of each of three test plants. Furthermore, spleen weight of the treated groups was significantly increased (P < 0.01). Two groups of mice were immunosuppressed with cyclophosphamide, the one which pretreated with the plants extracts significantly (P < 0.01) restored their resistance against lethal infection with the predominately granulocyte-dependant Candida albicans. These results confirm the immunomodulatory activity of Silene, Black seed, and Chamomile extracts and may have therapeutical implications in prophylactic treatment of opportunistic infections and as supportive treatment in oncogenic cases.

STRUCTURE OF A FURTHER TRITERPENE SAPONIN FROM ARENARIA FILICAULIS BOISS.

A novel triterpenoid saponin, Snatzkein E, was isolated from Arenaria filicaulis Boiss. It possesses a new aglycone and a glucose moiety carrying a sulfate group at C‐2′. Its structure and conformational behaviour were investigated by one‐ and two‐dimensional 1H and 13C NMR spectroscopy.

Isolation of triterpene saponins from Gypsophila capillaris

Four novel triterpenoid saponins have been isolated from Gypsophila capillaris. Three were monodesmosidic: 3 beta-hydroxyolean-12-en-23,28-dioic acid 28-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->2)] [beta-D-galactopyranosyl(1-->6)]beta-D-glucopyranoside, 3 beta-hydroxyolean-12-en-23-oxo-28-oic acid 28-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->3)] [beta-D-glucopyranosyl(1-->6)]beta-D-galactopyranoside, 3 beta-hydroxyolean-12-en-23,28-dioic acid 28-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->3)] [beta-D-glucopyranosyl(1-->6)]beta-D-galactopyranoside. The fourth was bisdesmosidic: 3 beta-hydroxyolean-12-en-23,28-dioic acid 23-O-beta-D-glucopyranosyl-28-O-[beta-D-glucopyranosyl-(1-->2)-beta-D- galactopyranosyl-(1-->3)][beta-D-glucopyranosyl-(1-->6)]beta-D- galactopyranoside. The structures of the compounds were elucidated by 1D and 2D NMR techniques and from other spectroscopic evidence.

Structures of Two Novel Triterpene Saponins from Arenaira filicaulis Boiss.

Two novel triterpenoid saponins, Snatzkein A and B, were isolated from Arenaria filicaulis Boiss. One possesses an unusual 2′‐O‐hydroxyethylated glucose moiety. Their structure and conformational behaviour were investigated by one‐ and two‐dimensional 1H and 13H NMR spectroscopy.

Glycosides from Bougainvillea glabra

Three glycosides were isolated from Bougainvillea glabra and their structures were determined by extensive use of 1D and 2D NMR spectroscopy (1H and 13C). Compound 1 was identical to momordin IIc (quinoside D) [β-D-glucopyranosyl 3-O-[β-D-xylopyranosyl-(1 → 3)-O-(β-D-glucopyranosyluronic acid)] oleanolate], compound 2 was quercetin 3-O-α-L-(rhamnopyranosyl)(1 → 6)-[α-L-rhamnopy-ranosyl(1 → 2)]-β-D-galactopyranoside and compound 3 was its derivative quercetin 3-O-α-L-(4-caffeoylrhamnopyranosyl)(1 → 6)-[α-L-rhamnopyranosyl (1 → 2)]-β-D-galactopyranoside, a new natural product.

Iridoid and lignan glycosides from Citharexylum spinosum L.

From the aerial parts of Citharexylum spinosum L., one new iridoid glucoside, the 7-β-O-acetate (1) of lamiide, along with four known iridoid glucosides, lamiide (2), lamiidoside (3), duranterectoside C (4), 8-epiloganin (5) and one known lignan glucoside (+)-lyonirenisol-3a-O-β-D-glucopyranoside (6) were isolated. The compound structures were established by one- and two-dimensional 1H- and 13C-NMR as well as by ESI-MS spectra.

Structure of a Novel Triterpene Saponin from Gypsophila capillaris (Forssk.)

A novel triterpenoid saponin was isolated from Gypsophila capillaris (Forssk.) and its structure and conformational behaviour were investigated by one‐ and two‐dimensional 1H and 13C NMR spectroscopy.

Two triterpene saponins from Arenaria filicaulis.

Two novel triterpenoid saponins, Snatzkein C, (3beta, 20-dihydroxylupan-28-oic acid 3-O-[beta-D-galactopyranosyl-(1-->2)-beta-D-glucopyranosyl-28- O-beta-D-glucopyranoside) and Snatzkein D, (3beta, 20-dihydroxylupan-28-oic acid 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]-28-O-beta-D-++ +glucopyranoside), have been isolated from Arenaria filicaulis. Their structure and conformational behaviour were elucidated by one- and two-dimensional 1H NMR and 13C NMR spectroscopy.

Immunomodulation of RAW 264.7 Murine Macrophage Functions and Antioxidant Activities of 11 Plant Extracts

A group of 11 medicinal plants, including Lavandula pubescens, Trigonella foenugricium, Salsola schweinforthi, Calligonum comosum, Silene succulenta, Silene villosa, Bogonvillea glabra, Cakile maritime, Gomphrene celesoids, Mirabilis jalaba, and Silene nocturna growing in Egypt, were extracted and examined for their immunomodulatory and antioxidant activities. RAW 264.7 cells were recruited to investigate the immunomodulatory effect through multiple parameters analysis. First, the proliferation index of macrophages cells was evaluated revealing that Trigonella foenugricium, Silene succulenta and Silene villosa have a significant cytotoxic effect on RAW cells. Interestingly, we observed enhancement of macrophages phagocytic function of by all extracts except Cakile maritime, Gomphrena celosioides and Silene nocturna. Afterwards, macrophages were challenged by incubation with LPS and the effect of various extracts on inflammatory responses was investigated; the generation of NO from activated macrophage was substantially suppressed by 7 extracts namely, Trigonella foenugricium, Calligonum comosum, Silene succulenta, Bougainvillea glabra, Mirabilis jalaba, Gomphrena celosioides and Silene nocturna. TNF-α was decreased by percentage range from 3.8 to 85.8% and Trigonella foenugricium extract showed the highest inhibition of TNF-α release. All extracts except Trigonella foenugricium, Salsola schweinforthi, Silene succulenta and Mirabilis jalaba significantly inhibited COX-2 production from stimulated macrophage. Moreover, evaluating the potential antioxidant activity of these extracts showed that Trigonella foenugricium, Salsola schweinforthi, Calligonum comosum, Bogonvillea glabra and Mirabilis jalaba exhibited some antioxidant activities. Taken together, our results suggest that some of these extracts may have a considerable antinflammatory and antioxidant effects and may be a potential therapeutic choice in the treatment of inflammatory diseases.