Hüseyin Anil

Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells

Malaria and cancer cause the death of millions of people every year. To combat these two diseases, it is important that new pharmaceutically active compounds have the ability to overcome multidrug resistance in cancer and Plasmodium falciparum strains. In search of effective anti-cancer and anti-malaria hybrids that possess improved properties compared to their parent compounds, a series of novel 1,2,4-trioxane-based hybrids incorporating egonol and/or ferrocene fragments were synthesized and tested in vitro against P. falciparum strains, CCRF-CEM cells and the multidrug-resistant P-glycoprotein-over-expressing CEM/ADR5000 cells. The most active compounds against P. falciparum strains were artesunic acid homodimers 12 and 13 (IC50 of 0.32 and 0.30 nM, respectively), whereas novel hybrids 7 (1,2,4-trioxane-ferrocene-egonol), 9 (1,2,4-trioxane-ferrocene) and 11 (artesunic acid-egonol) showed a remarkable cytotoxicity toward CCRF-CEM cells (IC50 of 0.07, 0.25 and 0.18 μM, respectively). A cooperative and synergistic effect of the three moieties 1,2,4-trioxane, ferrocene and egonol in hybrid molecule 7 is significant and is obviously stronger than in hybrids 9 (1,2,4-trioxane-ferrocene) and 11 (artesunic acid-egonol), which comprises of only two of the three considered parent compounds. Interestingly, hybrid 9 containing a 1,2,4-trioxane and a ferrocene fragment has shown to be the most effective among the studied hybrids against the tested multidrug-resistant leukemia CEM/ADR5000 cells (IC50 of 0.57 μM) and possesses a degree of cross-resistance of 2.34.

Four terpenoids from Cedrus libanotica

Abstract Structures are proposed for four new terpenoids, α-torosol,β-torosol, andirolactone and trans -atlanton-6-ol, isolated from the neutral fraction of the petroleum ether extract of Cedrus libanotica wood.

Synthesis of egonol derivatives and their antimicrobial activities.

Eighteen derivatives of egonol (A-R) were synthesized and evaluated for their antimicrobial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC 6633, Candida albicans ATCC 10231 and Escherichia coli ATCC 8739 microorganisms comparing with egonol. The obtained data reported that compound B exhibited improved activities against all tested bacteria than egonol, others have shown different range of activities.

Antimicrobial and Antifungal Activities of Three New Triterpenoid Glycosides

The antimicrobial and antifungal activities of the MeOH extract of the flowers of Cephalaria transsylvanica and three triterpenic acid glycosides, transsylvanoside A–C from the flowers of the plant were assayed using an agar‐disc diffusion method. The results showed that both the MeOH extract and the glycosides possess antimicrobial and antifungal activities against Staphylococcus aureus, Escherichia coli, Proteus vulgaris, Pseudomonas aeruginosa, Corynebacterium xerosis, Klebsiella pneumoniae, Candida utilis, Kluyveromyces fragilis, Aspergillus oryzae and Aspergillus flavus respectively.

Triterpenoid glycosides from Cephalaria transsylvanica

On the basis of spectroscopic and chemical methods, the structures of two new triterpenoid glycosides, transsylvanoside E and F, isolated from Cephalaria transsylvanica have been established as 3-O-[beta-D-xylopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->2)-beta-D-xylopyranosyl]-3 beta,23- dihydroxy delta 12-oleanen-28-carboxylic acid and 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L-rhamnopyranosyl (1-->4)-beta-D-xylopyranosyl]-28-O-[beta- D-glucopyranosyl (1-->4)-beta-D-glucopyranosyl]-3 beta,23-dihydroxy delta 12-oleanen- 28-carboxylic acid, respectively. A new proglycoside was isolated from the cleavage of the ester-glycoside linkage and its structure characterized as 3-O-[beta-D-glucopyranosyl (1-->3)-alpha-L- rhamnopyranosyl (1-->4)-beta-D-xylopyranosyl]-3 beta,23-dihydroxy delta 12-oleanen-28-carboxylic acid.

Saponins from Styrax officinalis

Three triterpene saponins named Styrax-saponin A-C (1-3) were found in pericarps of Styrax officinalis together with the deacylsaponin (4). Structural determinations were achieved using 1D-, 2D-NMR and mass spectrometry.

AN ACIDIC TRITERPENE GLYCOSIDE FROM CEPHALARIA TRANSSYLVANICA

Transsylvanoside B, which is a new acidic triterpene glycoside, was isolated from dried flowers of Cephalaria transsylvanica. The structure was determined as 3-O-[beta-D- glucopyranosyl(1-->2)-beta-D-xylopyranosyl(1-->4)-alpha-L-rhamnopyran osy l (1-->4)-beta-D-xylopyranosyl]-3 beta,23-dihydroxy delta 12-oleanen-28-carboxylic acid.

A furostanol saponin and phytoecdysteroid from roots of Helleborus orientalis

A furostanol saponin mixture and a known phytoecdysteroid were isolated from the roots of Helleborus orientalis Lam. Their structures were established as 26-[(β-D-glucopyranosyl)oxy]-22α-hidroxyfurosta-5,25(27)-dien-1β,3β,11α-triol (1a), 26-[(β-D-glucopyranosyl)oxy]-22α-methoxyfurosta-5,25(27)-dien-1β,3β,11α-triol (1b), and 20-hydroxy-β-ecdyson-3-O-β-D-glycoside (2). Acid hydrolysis of 1a,b gave (1β,3β,11α,22α)-22,26-dimethoxyfurosta-5,25(27)-dien-1,3,11-triol (aglycone 1) and of 2 gave 20-hydroxy-β-ecdyson (aglycone 2). Their structures were elucidated by spectral analysis.

Terpene acids from Cedrus libani

Abstract Structures are proposed for three new terpene acids, atlantonic acid, dihydroatlantonic acid and libanotic acid, isolated from the acidic fraction of the petrol extract of Cedrus libani wood. In addition, three resin acids, abietic acid, dehydroabietic acid and isodextropimaric acid were isolated from the same source.

Transsylvanoside a, an acidic triterpene glycoside from Cephalaria transsylvanica

A new acidic triterpene glycoside, transsylvanoside A, was isolated from dried flowers of Cephalaria transsylvanica. The structure was determined to be 3-O-[beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl(1-->4)-al pha-L-rhamnopyranosyl(1-->4)-beta-D-xylopyranosyl]-3beta,23-dihydroxy delta(12)-oleanen-28-carboxylic acid.