Biomedical subjects

Ihsan Caliş

Publications and source records attributed to Ihsan Caliş.

At least 19 recordsLinked to original sources

PubMed2006

Antioxidant, anti-inflammatory, anti-nociceptive activities and composition of Lythrum salicaria L. extracts.

Lythrum salicaria (purple loosestrife) known as "Tibbi hevhulma" in Turkish is used for its several beneficial health effects against as diarrhea, chronic intestinal catarrh, hemorrhoid and eczema in the form of a decoction or a fluid extract and to treat varicose veins, bleeding of the gums, hemorrhoid and eczema, externally. Dried herbal parts of Lythrum salicaria L. (Lythraceae) were sequentially extracted with different solvents such as petroleum ether, ethyl acetate, methanol and 50% aqueous methanol. Water extract of Lythrum salicaria was also prepared under reflux. Antioxidant, anti-inflammatory and anti-nociceptive activities of all the extracts were investigated using in vitro and in vivo methods, respectively. Free radical scavenging activity (1,1-diphenyl-2-picrylhydrazyl, DPPH* assay), iron(III) reductive activity, capacity of the inhibition of linoleic acid peroxidation and MDA formation, anti-nociceptive activity (p-benzoquinone-induced abdominal constriction test) and anti-inflammatory activity (carrageenan-induced hind paw edema model) were used for all the extracts. In addition, the content of total phenolics, flavonoids and flavonols in all the extracts were determined with spectrophotometric methods. Results were compared with reference antioxidants via ascorbic acid, butylated hydroxytoluene, and gallic acid. Qualitative and quantitative compositions of all the extracts were analysed using a HPLC-PDA system. Polar fractions were found to be rich in flavonoids such as isovitexin and isoorientin.

Analgesics↗

PubMed2006

ent-7alpha,18-Hydroxykaur-16-ene ethanol solvate.

The ent-kaurene diterpene in the title compound, 7-epicandicandiol ethanol solvate, C20H32O2.C2H6O, was isolated from the aerial parts of Sideritis ozturkii Aytaç & Aksoy. The molecule has the usual conformation and stereochemistry found in related ent-kaurene derivatives. The methyl-substituted ring junction has a trans arrangement and the other junction is cis. The six-membered rings have chair or slightly distorted chair conformations and the five-membered ring has an envelope conformation. Intermolecular hydrogen bonds link the 7-epicandicandiol and ethanol molecules into two-dimensional networks, part of which comprise co-operative O-H...O-H...O-H... chains.

Crystallography, X-Ray↗

PubMed2006

Antitrypanosomal cycloartane glycosides from Astragalus baibutensis.

Baibutoside (5), a new cycloartane-type triterpene glycoside, has been isolated from the roots of Astragalus baibutensis along with four known glycosides, acetylastragaloside I (1), and astragalosides I, II, and IV (2-4, resp.). The structure elucidation of the compounds were achieved by a combination of one- and two-dimensional NMR techniques (DQF-COSY, HSQC, HMBC, and ROESY), and mass spectrometry (ESI-MS), where all the compounds were shown to have cycloastragenol (=(20R,24S)-3beta,6alpha,16beta,25-tetrahydroxy-20,24-epoxy-9,19-cyclolanostane) as aglycone. All compounds were tested for in vitro antiprotozoal activity. Compounds 1-4 displayed notable activity vs. Trypanosoma brucei rhodesiense, with acetylastragaloside I (1) being the most potent (IC50 9.5 microg/ml). Acetylastragaloside I (1) was also lethal to T. cruzi (IC50 5.0 microg/ml), and it is the first cycloartane-type triterpene with remarkable trypanocidal activity against both T. brucei rhodesiense and T. cruzi. However, it exhibits some cytotoxicity on mammalian cells.

Animals↗

PubMed2005

Effects of triterpene saponins from Astragalus species on in vitro cytokine release.

Roots of Astragalus species are used to treat leukemia and for wound healing in Turkish folk medicine. In order to evaluate this information, the effect of 13 cycloartane- and 1 oleanan-type triterpene saponins isolated from Turkish species (Astragalus brachypterus, Astragalus cephalotes, Astragalus microcephalus, and Astragalus trojanus), as well as methanol extracts from the roots of three Astragalus species (Astragalus cephalotes, Astragalus oleifolius and Astragalus trojanus) were studied. Cytokine concentrations of interleukins IL-1beta, IL-8 and TNF-alpha after bacterial lipopolysaccharide (LPS) and IL-2, IL-4 and INF-gamma after phorbolacetate (PHA) stimulation were determined using commercial enzyme-linked immunosorbent assay (ELISA) kits. All triterpene saponins tested in the present study showed a prominent IL-2 inducing activity between 35.9% and 139.6%. Among the extracts the highest score was obtained for Astragalus oleifolius (141.2%). Glycosides of 20,24-epoxy and 20,25-epoxy cycloartanes showed higher IL-2 inducing activity than those of acyclic-cycloartane derivatives as well as aglycone of 20,24-epoxy cycloartanes, cycloastrogenol. Especially the activity of Astragaloside VII, a tridesmosidic glycoside of cycloastrogenol, was the most remarkable. The oleanan-type triterpene saponin also showed a prominent IL-2 inducing activity. IL-2 is a cytokine produced by activated T cells, which has shown powerful immunostimulatory and antineoplastic properties. Accordingly, the IL-2 inducing activity of the triterpene saponins might be the mechanism involved in order to explain the immunomodulatory and anticancer effects of Astragalus species.

Adjuvants, Immunologic↗

PubMed2005

Leishmanicidal cycloartane-type triterpene glycosides from Astragalus oleifolius.

Two new cycloartane-type glycosides oleifoliosides A (1) and B (2) were isolated from the lower stem parts of Astragalus oleifolius. Their structures were identified as 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-xylopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane and 3-O-[beta-xylopyranosyl-(1 --> 2)-alpha-arabinopyranosyl]-6-O-beta-glucopyranosyl-3beta,6alpha,16beta,24(S),25-pentahydroxycycloartane, respectively, by means of spectroscopic methods (IR, 1D and 2D NMR, ESI-MS). Three known cycloartane glycosides cyclocanthoside E (3), astragaloside II (4) and astragaloside IV (5) were also isolated and characterized. All five compounds were evaluated for in vitro trypanocidal, leishmanicidal and antiplasmodial activities as well as their cytotoxic potential on primary mammalian (L6) cells. Except for the compound 5, all compounds showed notable growth inhibitory activity against Leishmania donovani with IC50 values ranging from 13.2 to 21.3 microg/ml. Only weak activity against Trypanosoma brucei rhodesiense was observed with the known compounds astragaloside II (4, IC50 66.6 microg/ml) and cyclocanthoside E (3, IC50 85.2 microg/ml), while all compounds were inactive against Trypanosoma cruzi and Plasmodium falciparum. None of the compounds were toxic to mammalian cells (IC50's > 90 microg/ml). This is the first report of leishmanicidal and trypanocidal activity of cycloartane-type triterpene glycosides.

Animals↗

PubMed2005

Secondary metabolites from Phlomis oppositiflora.

In addition to rare phenylethanoid triglycosides, myricoside and its dimetylether derivative serratumoside A {3-hydroxy,4-methoxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-4-O-feruloyl-beta-D-glucopyranoside}, a new phenylethanoid glycoside, myricoside-3""-O-methylether {3,4-dihydroxy-beta-phenylethoxy-O-beta-D-apiofuranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-4-O-feruloyl-beta-D-glucopyranoside} along with a new neolignan glucoside, (7S, 8R)-dehydroconiferyl alcohol-8-5'-dehydroconiferyl aldehyde 4-O-beta-D-glucopyranoside were isolated from the aerial parts of Phlomis oppositiflora. The structures of the new compounds were identified by means of spectroscopic (UV, IR, 1D- and 2D-NMR, and LC-ESIMS) methods.

Glycosides↗

PubMed2004

Three acylated flavone glycosides from Sideritis ozturkii Aytac & Aksoy.

From the aerial parts of Sideritis ozturkii, three new flavonoids, chrysoeriol 7-O-[2'''-O-caffeoyl-O-acetyl-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside], chrysoeriol 7-O[2'''-O-caffeoyl-beta-D-glucopyranosyl-(1 -->2)-beta-D-glucopyranoside] and chrysoeriol 7-O[2'''-O-p-coumaroyl-6'''-beta-O-acetyl-D-glucopyranosyl-(1-->2)-beta-D-glucopyranoside] named as ozturkosides A, B and C, respectively, were isolated, along with three known phenylethanoid glycosides, verbascoside, leucoseptoside A, martynoside and five known diterpenoids, 7-epicandicandiol, linearol, sidol, sideroxol, epoxyisolinearol. The structures were elucidated mainly by spectroscopic methods.

Chromatography, Liquid↗

PubMed2004

Glycosides from Phlomis lunariifolia.

An aliphatic alcohol glycoside, lunaroside 1-octen-3-yl [O-beta-apiofuranosyl-(1-->6)-O-[beta-glucopyranosyl-(1-->2)]-beta-glucopyranoside, a phenylethanoid glycoside, lunariifolioside 2-(3,4-dihydroxyphenyl)ethylO-beta-apiofuranosyl-(1-->6)-O-[O-beta-apiofuranosyl-(1-->4)-alpha-rhamnopyranosyl-(1-->3)]-4-O-(E)-caffeoyl-beta-glucopyranoside and a flavone glycoside, luteolin 7-O-[4-O-acetyl-alpha-rhamnopyranosyl-(1-->2)]-beta-glucuronopyranoside, were isolated from the aerial parts of Phlomis lunariifolia, in addition to 15 known glycosides. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical degradation.

Caffeic Acids↗

PubMed2003

Wiedemanniosides A-E: new phenylethanoid glycosides from the roots of Verbascum wiedemannianum.

From the aerial parts of Verbascum wiedemannianum Fisch. & Mey. four new phenylethanoid glycosides (wiedemanniosides B - E) were isolated along with four known compounds; 6- O-acetylmartynoside (= wiedemanniosides A), verbascoside, martynoside, echinacoside and leucosceptoside B. The structures of the new compounds were elucidated by employing spectroscopic techniques (NMR, HR-ESIMS, IR, and UV).

Antioxidants↗

PubMed2002

Effects of Gentiana lutea ssp. symphyandra on the central nervous system in mice.

A methanolic extact of Gentiana lutea ssp. symphyandra roots has been investigated for its possible effects on the central nervous system of mice. At doses of 250 and 500 mg/kg (i.p.), the methanol extract of Gentiana roots caused a significant increase in the swimming endurance test and exhibited slight analgesic activity, but no lethality in mice suggesting some activity on the central nervous system. However, there was no indication of sedation or muscular fatigue at the doses employed. HPLC analysis showed that three secoiridoid compounds, gentiopicroside, swertiamarine and sweroside were present and may have been responsible for the CNS effects of the methanol extract of Gentiana lutea ssp. symphyandra roots.

Analgesics↗

PubMed2002

(6S)-Hydroxy-3-oxo-alpha-ionol glucosides from Capparis spinosa fruits.

Two new (6S)-hydroxy-3-oxo-alpha-ionol glucosides, together with corchoionoside C ((6S,9S)-roseoside) and a prenyl glucoside, were isolated from mature fruits of Capparis spinosa. The structures were established on the basis of spectroscopic, chiroptic and chemical evidence. In addition, the 13C-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The alpha-ionol derivatives are metabolites of (+)-(S)-abscisic acid.

Fruit↗

PubMed2002

Coumarin glucosides from Cruciata taurica.

Two new coumarin glycosides (1 and 2) along with two known coumarin glucosides, daphnin (3) and daphnetin glucoside (4) were isolated from the aerial parts of Cruciata taurica. The structures of the new compounds were elucidated by spectral methods and chemical means as 7-O-(6' -acetoxy-beta-D-glucopyranosyl)-8-hydroxycoumarin (1) and 7-O-[6 '-O-(3'',4''-dihydroxycinnamoyl)-beta-D-glucopyranosyl]-8-hydroxycoumarin (2). The phylogenetic significance of coumarins in C. taurica was discussed.

Coumarins↗

PubMed2002

Iridoid glycosides from Globularia davisiana.

From the ethanolic extract of the aerial parts of Globularia davisiana, a new iridoid glycoside, davisioside (1), was isolated. Davisioside (1) comprises a rare iridoid aglycone structure with a saturated double bond between C-3 and C-4. Nine known iridoid glycosides, asperuloside (2), alpinoside (3), geniposide (4), globularin (5), globularicisin (6), 10-O-benzoylcatalpol (7), lytanthosalin (8), melampyroside (9), agnuside (10), and three known phenylethanoid glycosides, verbascoside, isoacteoside and leucosceptoside A were also isolated and characterized. The structures of the isolates were established by spectroscopic methods (one-dimensional (1D)- and two-dimensional (2D)-NMR, MS).

Biphenyl Compounds↗

PubMed2002

Lucidin type anthraquinone glycosides from Putoria calabrica.

Two new lucidin type anthraquinone glycosides, putorinoside A (1) and putorinoside B (2) were isolated from Putoria calabrica, in addition to two known anthraquinone glycosides, lucidin 3-O-beta-glucopyranoside (3) and lucidin 3-O-primeveroside (4). Based on spectroscopic data, putorinosides A and B were identified as 2-hydroxymethyl-1-methoxy-3,5,6-trihydroxyanthraquinone 3-O-beta-glucopyranoside and 2-hydroxymethyl-1-methoxy-3,6-dihydroxyanthraquinone 3-O-beta-glucopyranoside, respectively.

Anthraquinones↗

PubMedDate not supplied

Identification by HPLC-PAD-MS and quantification by HPLC-PAD of phenylethanoid glycosides of five Phlomis species.

The qualitative and quantitative determination of phenylethanoid glycosides in methanolic extracts of five species of the genus Phlomis (Lamiaceae) has been investigated using a new reversed-phase HPLC method combined with photodiode-array detection and electrospray/MS analysis. Forsythoside B, verbascoside, samioside, alyssonoside, isoverbascoside, leucosceptosides A and B and martynoside were detected. The quantification of the above constituents was performed using echinacoside as internal standard. Knowledge of the content of phenylethanoid glycosides contributes to the chemotaxonomy of the genus.

Chromatography, High Pressure Liquid↗

PubMedDate not supplied

Neolignan glucosides from Phlomis chimerae Boiss.

From the aerial parts of the plant Phlomis chimerae, a new neolignan glucoside, (-)-4-O-methyldihydrodehydrodiconiferyl alcohol-9'-O-beta-D-glucopyranoside (1) was characterized along with the known neolignan glucosides, (-)-4-O-methyldehydrodiconiferyl alcohol-9'-O-beta-D-glucopyranoside (= longifloroside A) (2) and (-)-dihydrodehydrodiconiferyl alcohol-9-O-beta-D-glucopyranoside (3). The structure of the new compound was established on the basis of spectroscopic evidence.

Asteraceae↗

PubMedDate not supplied

Composition of lipophylic extracts from two Tinicates, Styela sp. and Phallusia sp. from the Eastern Mediterranean.

Sterols, volatiles and lipids were isolated and identified from lipophylic extracts from two tunicates, Styela sp. and Phallusia sp., occurring in the Eastern Mediterranean. Seventeen sterols were identified. The sterol composition of the two organisms appeared to be similar except for the concentrations of 5alpha-stanols. Both tunicates were characterized by the presence of sterols with a (22Z)-double bond. In the volatiles significant amounts of chlorinated compounds were found (phenols in Styela sp. and hydrocarbons in Phallusia sp.). The fatty acid composition of triacylglycerols and phospholipids of the two tunicates showed significant differences.

Animals↗

PubMedDate not supplied

Chemical composition of Cystoseira crinita Bory from the Eastern Mediterranean.

The chemical composition of the brown alga Cystoseira crinita Bory from the Eastern Mediterranean was investigated. Fourteen sterols have been identified, five of them for the first time in algae. The structure of one new sterol was established. The origin of seven sterols with short side chains was discussed. In the volatile fraction 19 compounds and in the polar fraction 15 compounds were identified. The main lipid classes were isolated and their fatty acid composition was established.

Alcohols↗