Abdelsamed I. Elshamy

Microbial biotransformation as a tool for drug development based on natural products from mevalonic acid pathway: A review

Graphical abstract

Molecular Architecture and Biomedical Leads of Terpenes from Red Sea Marine Invertebrates

Marine invertebrates including sponges, soft coral, tunicates, mollusks and bryozoan have proved to be a prolific source of bioactive natural products. Among marine-derived metabolites, terpenoids have provided a vast array of molecular architectures. These isoprenoid-derived metabolites also exhibit highly specialized biological activities ranging from nerve regeneration to blood-sugar regulation. As a result, intense research activity has been devoted to characterizing invertebrate terpenes from both a chemical and biological standpoint. This review focuses on the chemistry and biology of terpene metabolites isolated from the Red Sea ecosystem, a unique marine biome with one of the highest levels of biodiversity and specifically rich in invertebrate species.

Chemical constituents and anti-ulcerogenic potential of the scales of Cynara scolymus (artichoke) heads

BACKGROUND Cynara scolymus L. (Asteraseae) (artichoke) is commonly eaten as a vegetable; its leaves are frequently used in folk medicine in the treatment of hepatitis, hyperlipidaemia, obesity and dyspeptic disorders. The purpose of this study is to determine the chemical composition of the volatile oil and alcoholic extract of artichoke head scales. In addition, the role of the methanol extract as an anti-ulcer agent against ethanol-induced gastric ulcer in rats was evaluated. RESULTS Six flavonoids and one phenolic acid were obtained from the methanol extract. Also, 37 compounds were identified in the volatile oil, the majority including mono- and sesquiterpenes. The artichoke extracts (200 and 400 mg kg(-1)) significantly (P < 0.05) reduced the ulcer index (55.33% and 72.14% inhibition). Histopathological examination of rat stomachs demonstrated that artichoke induced an increase in gastric mucus production, and a reduction of the depth and severity of mucosal lesions. Artichoke dose-dependently reduced the elevated ethanol gastric malonylaldehyde, and reduced glutathione levels and catalase activity. These results suggest that the head scales of artichoke possess potential anti-ulcer activity. CONCLUSIONS The present paper describes the identification of volatile oil for the first time along with the isolation and identification of the constituents of the methanol extract. Moreover, the high anti-ulcerogenic potential of scales of C. scolymus heads was established here for the first time.

A new steroid from the Red Sea soft coral Lobophytum lobophytum

Chemical investigation of the soft coral Lobophytum lobophytum collected from the Red Sea led to the isolation of a new compound gorgostan-5,25-dien-3β-ol (1), and two known compounds gorgosterol (2), and alismol (3). Structures were elucidated by employing extensive NMR and HR-ESI-MS experiments.

A new gorgostane derivative from the Egyptian Red Sea soft coral Heteroxenia ghardaqensis

Chemical investigation of the chloroform extract of the Egyptian Red Sea soft coral, Heteroxenia ghardaqensis (Family Xeniidae), led to the isolation of three gorgostane derivatives, namely gorgosten-5(E)-3β-ol (1), gorgostan-3β,5α,6β, 11α-tetraol (sarcoaldosterol A) (2) and gorgostan-3β,5α,6β-triol-11α-acetate (3). To our knowledge, sterol 3 is reported in this article for the first time. The structure elucidation of these compounds was deduced by 1-D and 2-D NMR as well as ESIMS. Sterol 1 showed moderate activity as growth inhibitor of human colon tumour cell lines.

Casbane Diterpenes from Red Sea Coral Sinularia polydactyla

The soft coral genus Sinularia is a rich source of bioactive metabolites containing a diverse array of chemical structures. A solvent extract of Sinularia polydactyla resulted in the isolation of three new casbane diterpenes: sinularcasbane M (1), sinularcasbane N (2) and sinularcasbane O (3); in addition, known metabolites (4–5) were isolated. Compounds were elucidated on the basis of spectroscopic analyses; the absolute configuration was confirmed by X-ray analysis.The soft coral genus Sinularia is a rich source of bioactive metabolites containing a diverse array of chemical structures. A solvent extract of Sinularia polydactyla resulted in the isolation of three new casbane diterpenes: sinularcasbane M (1), sinularcasbane N (2) and sinularcasbane O (3); in addition, known metabolites (4-5) were isolated. Compounds were elucidated on the basis of spectroscopic analyses; the absolute configuration was confirmed by X-ray analysis.The soft coral genus Sinularia is a rich source of bioactive metabolites containing a diverse array of chemical structures. A solvent extract of Sinularia polydactyla resulted in the isolation of three new casbane diterpenes: sinularcasbane M (1), sinularcasbane N (2) and sinularcasbane O (3); in addition, known metabolites (4-5) were isolated. Compounds were elucidated on the basis of spectroscopic analyses; the absolute configuration was confirmed by X-ray analysis.

Cembrene Diterpenoids with Ether Linkages from Sarcophyton ehrenbergi: An Anti-Proliferation and Molecular-Docking Assessment

Three new cembrene diterpenoids, sarcoehrenbergilid A–C (1–3), along with four known diterpenoids, sarcophine (4), (+)-7α,8β-dihydroxydeepoxysarcophine (5), sinulolide A (6), and sinulolide B (7), and one steroid, sardisterol (8), were isolated and characterized from a solvent extract of the Red Sea soft coral Sarcophyton ehrenbergi. Chemical structures were elucidated by NMR and MS analyses with absolute stereochemistry determined by X-ray analysis. Since these isolated cembrene diterpenes contained 10 or more carbons in a large flexible ring, conformer stabilities were examined based on density functional theory calculations. Anti-proliferative activities for 1–8 were evaluated against three human tumor cell lines of different origins including the: lung (A549), colon (Caco-2), and liver (HepG2). Sardisterol (8) was the most potent of the metabolites isolated with an IC50 of 27.3 µM against the A549 cell line. Since an elevated human-cancer occurrence is associated with an aberrant receptor function for the epidermal growth factor receptor (EGFR), molecular docking studies were used to examine preferential metabolite interactions/binding and probe the mode-of-action for metabolite-anti tumor activity.

Essential Oil and Antimicrobial Activity of Aerial Parts of Cyperus leavigatus L. (Family: Cyperaceae)

Abstract The essential oil of the aerial parts of Cyperus leavigatus L. was obtained by hydro-distillation and analyzed by gas chromatography/mass spectrometry (GC-MS). Sixty Six compounds were identified in the essential oil representing 92.92 % of the total mass. Terpenes represent the major constituents (77.78 %), including monoterpenes (47.63 %), sesquiterpenes (21.49 %), and diterpenes (8.36 %). The major chemical constituents of the oil were found to be hexahydrofarnesyl acetone (19.13 %), Z-myroxide (8.14 %), phytol (6.96 %), limonene (6.74 %), E-myroxide (M) (6.72 %), and cis-carveol (5.56 %). The essential oil, the total and n-butanol extracts showed moderate antimicrobial activity in vitro against gram positive bacteria and yeast with MIC ranging from 100-250 µg/disc. Additionally, the ethyl acetate and dichloromethane extracts revealed strong antimicrobial activities against gram positive bacteria Staphylococcus aureus, Bacillus subtilis and the yeast, Candida albicans (10-20 µg/disc), along with a moderate antimicrobial activity against the gram negative bacteria Escherichia coli and Pseudomonas aeruginosa (MIC 100-500 µg/disc) in comparison with the positive controls thiamphenicol and nystatin.

Anti-inflammatory, Antipyretic, and Antinociceptive Effects of a Cressa cretica Aqueous Extract

Cressa cretica is a widely grown halophytic plant traditionally used for the treatment of different ailments. Previous investigations reported its biological activity on a wide spectrum of diseases. In this study, in vivo antinociceptive, anti-inflammatory, and antipyretic activities of C. cretica aqueous extract whole plant were evaluated. In addition, the total polyphenol content, the total flavonoid content, and the chemical characterization of the extract were performed. C. cretica showed writhing inhibition in acetic acid-induced peripheral nociception of 43 and 48 % at doses of 50 and 100 mg/kg, respectively. The same doses increased latency time in a hot plate model of central analgesia by 66 and 78 % compared to the control group, respectively. The acute anti-inflammatory effect of the extract was explored in the carrageenan-induced rat hind paw test. The inhibition of paw volume was better than that of the standard drug indomethacin. C. cretica significantly decreased rectal temperature in the rats injected with Brewers yeast. C. cretica aqueous extract showed both central and peripheral antinociceptive activities and was effective as an anti-inflammatory and antipyretic. Phenolic compounds, including chlorogenic acids and flavonol glycosides, were identified by HPLC-PDA-ESI-MS techniques. These findings indicate the medicinal importance of this traditionally used plant as a therapeutic remedy for different ailments.

Lobophylins F-H: three new cembrene diterpenoids from soft coral Lobophytum crassum

Abstract Three new cembrenoids, lobophylins F-H (1–3), along with three known ones, lobophylins A-C (4–6), were isolated from the ethyl acetate extract of the Taiwan water soft coral Lobophytum crassum. The structures of isolated cembrenoids were elucidated on the basis of extensive spectroscopic methods such as IR, 1D, 2D NMR and HR–ESI–MS.