Ihsan Calis

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

Abstract Two new (6 S )-hydroxy-3-oxo-α-ionol glucosides, together with corchoionoside C ((6 S ,9 S )-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 13 C-resonance of C-9 was found to be of particular diagnostic value in assigning the absolute configuration at that center in ionol glycosides. The α-ionol derivatives are metabolites of (+)-( S )-abscisic acid.

Isomartynoside, a phenylpropanoid glycoside from Galeopsis pubescens

Abstract The structure of isomartynoside, a new phenylpropanoid glycoside, isolated along with the known martynoside from Galeopsis pubescens, has been elucidated on the basis of chemical and spectral data as 3-hydroxy-4-methoxy-β-phenylethoxy-O-α- L -rhamnopyranosyl-(1 → 3)-6-O-feruloyl-β- D -glucopyranoside.

Secoiridoid glucosides from Lonicera periclymenum

Abstract The stems of Lonicera periclymenum have been investigated for secoiridoid glycosides. In addition to two well-known glucosides, secologanin and morroniside, two rare secoiridoids, secoxyloganin and secologanoside, have been isolated and characterized by chemical and spectroscopic means. Secologanoside has been isolated for the first time as a genuine, non-derivatized compound.

PHENYLPROPANOID GLYCOSIDES FROM MARRUBIUM ALYSSON

From the aerial parts of Marrubium alysson a new phenylpropanoid glycoside, alyssonoside, and five known glycosides, verbascoside (= acteoside), leucosceptoside A, martynoside, forsythoside B and leucosceptoside B were isolated. On the basis of spectral data, the structure of the new compound was elucidated as beta-(3,4-dihydroxyphenyl)ethyl-O-[alpha-L-rhamnopyranosyl-(1-->3)]-O- [beta-D-apiopyranosyl-(1-->6)]-4-O-feruloyl-beta-D-glucopyra noside.

1H-Indole-3 acetonitrile glycosides from Capparis spinosa fruits

Abstract Two new glucose-containing 1 H -indole-3-acetonitrile compounds, capparilosides A and B, were isolated from mature fruits of Capparis spinosa . On the basis of spectral and chemical evidence, they were shown to be 1 H -indole-3-acetonitrile 4- O - β -glucopyranoside and 1 H -indole-3-acetonitrile 4- O - β - (6′- O - β -glucopyranosyl)-glucopyranoside, respectively.

Neo-clerodane diterpenoids from Teucrium polium

Two new neo-clerodane type diterpenoids, teulolin A (15,16-epoxy-6,7,18,19-tetrahydroxy-neo-cleroda-3(4),13(16),14-trien-20, 12(S)-olide, 1) and teulolin B (15,16-epoxy-3α, 6,7,18,19-tetrahydroxy-neo-cleroda-4(18),13(16),14- trien-20,12(S)-olide, 2) were isolated from the aerial parts of Teucrium polium. The structures of 1-2 were proposed on the basis of extensive NMR experiments and molecular modeling studies

Bioassay-guided isolation of anti-inflammatory and antinociceptive principles from a folk remedy, Rhododendron ponticum L. leaves

ETHNOPHARMACOLOGICAL RELEVANCE Rhododendron ponticum L. (Ericaceae) is used for the treatment of inflammatory diseases and to alleviate rheumatic pain and against toothache in Turkish traditional medicine. AIM OF THE STUDY To evaluate the anti-inflammatory and antinociceptive effects of Rhododendron ponticum leaves using in vivo models, and isolation and chemical characterization of the biologically active constituents through bioassay-guided fractionation procedures. MATERIAL AND METHODS Carrageenan-induced hind paw edema model was used for anti-inflammatory activity and p-benzoquinone induced abdominal contractions model for the antinociceptive activity assessment. RESULTS The ethylacetate fraction displayed marked anti-inflammatory (28.4-40.7% inhibition) and antinociceptive (50.7% inhibition) effects as compared to reference compounds. Through bioassay-guided fractionation and isolation procedures flavonol glycosides [a mixture of hyperoside and isoquercitrin (1) and quercitrin (2)] along with one flavanone glycoside [6-C-glycosylnaringenin (3)] were isolated as the active ingredients of ethylacetate extract against carrageenan-induced edema and p-benzoquinone-induced writhes and their structures were elucidated by spectral techniques. 1 and 2 also showed a significant anti-inflammatory activity against 12-O-tetradecanoyl-13-acetate (TPA)- induced mouse ear edema model. CONCLUSION Results of the present study supported the utilization of the plant in Turkish folk medicine and revealed that flavones are the major anti-inflammatory and antinociceptive principles of the leaves.

Adjuvant effects of Astragalus saponins macrophyllosaponin B and astragaloside VII.

AIM OF THE STUDY The present study was undertaken to evaluate the hemolytic activities of two immunomodulator Astragalus saponins [Macrophyllosaponin B (MacB) from Astragalus oleifolius DC. and Astragaloside VII (Ast VII) from Astragalus trojanus Stev.], and their adjuvant potentials on the cellular and humoral immune responses of Swiss albino mice against BSA. MATERIALS AND METHODS The hemolytic activity of Mac B and Ast VII was determined using 0.5% rabbit red blood cell. For adjuvant activity, Swiss albino mice were immunized subcutaneously with BSA 100 μg alone or with BSA 100 μg dissolved in saline containing Ast VII (30, 60, 120 and 240 μg), Mac B (30, 60, 90 and 120 μg) or Freunds adjuvant on Days 1 and 15. Sera and splenocytes were collected 2 weeks after the last immunization for concanavalin A (Con A)-, lipopolysaccharide (LPS)- and BSA-stimulated splenocyte proliferation assay and measurement of BSA-specific antibodies in serum. RESULTS Mac B and Ast VII showed a slight hemolytic effect, with 0.42% and 0.54% values, respectively, at the highest concentration of 500 μg/ml. Mac B and Ast VII significantly enhanced the Con A-, LPS-, and BSA-induced splenocyte proliferation in the BSA-immunized mice especially at 120 and 240 μg (P<0.001), and 60, 90 and 120 μg (P<0.05, P<0.01 or P<0.001) doses, respectively. BSA-specific IgG, IgG1 and IgG2b antibody titers in serum were also significantly enhanced by Ast VII (120 μg), Mac B (90 μg) and Freunds as compared to the control group (P<0.01 or P<0.001). Moreover, the IFN-γ and IL-4 levels in the sera were detected using ELISA two weeks after the last immunization. Ast VII and Mac B were also found to stimulate IFN-γ production such as Freunds, two weeks after the last immunization at doses of 120 μg and 90 μg, respectively, as compared to the control. CONCLUSION Results show that Ast VII and Mac B generate important specific antibody and cellular response against BSA in mice, proving their potentials as a new class saponin adjuvant.

Trojanoside H: a cycloartane-type glycoside from the aerial parts of Astragalus trojanus

Abstract A novel cycloartane-type glycoside was isolated from the aerial parts of Astragalus trojanus along with the known glycosides astragaloside II, astragaloside IV, astragaloside VII, brachyoside B, brachyoside C and the pterocarpan derivative maackiain. The structure of 1 was determined by spectral methods (1-D and 2-D NMR, and FABMS) and established as 3- O -β-[α- l -arabinopyranosyl(1→2)β- d -xylopyranosyl]-6- O -β- d -glucopyranosyl-20( R ),24( S )-epoxy-3β,6α,16β,25-tetrahydroxycycloartane.

Triterpene saponins from the fruits of Hedera helix.

Six triterpene saponins, including two new compounds, were isolated from the fruits of Hedera helix L. (Araliaceae). The structures of the new compounds, named helixosides A and B, were established as 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl hederagenin 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, and 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, respectively, on the basis of chemical and spectral data.