Tayfun Ersöz

Two phenylpropanoid glycosides fromLeonurus glaucescens

Two new phenylpropanoid glycosides, leonosides A and B, and two known glycosides lavandulifolioside and verbascoside, were isolated from the aerial parts of Leonurus glaucescens. On the basis of chemical and spectral evidence, leonosides A and B were shown to be beta-(3,4-dihydroxyphenyl)-ethyl-O-alpha-L-arabinopyranosyl-(1---- 2)-alpha-L- rhamnopyranosyl-(1----3)-4-O-feruloyl-beta-D-glucopyranoside and beta-(3-hydroxy, 4-methoxyphenyl)-ethyl-O-alpha-L-arabinopyranosyl-(1----2)- alpha-L-rhamnopyranosyl-(1----3)-4-O-feruloyl-beta-D-glucopyranosi de, respectively.

In vivo anti-inflammatory and antinociceptive actions of some Lamium species

ETHNOPHARMACOLOGICAL RELEVANCE Several Lamium species have been used to relieve pain in arthritic ailments in Turkish folk medicine. AIM OF THE STUDY To evaluate the anti-inflammatory and antinociceptive activities of different extracts prepared with methanol, dichloromethane, n-butanol and water from the aerial parts of some Lamium species of Turkish origin. MATERIALS AND METHODS Lamium eriocephalum subsp. eriocephalum, Lamium garganicum subsp. laevigatum, Lamium garganicum subsp. pulchrum and Lamium purpureum var. purpureum (Lamiaceae); for the anti-inflammatory activity, carrageenan-induced hind paw edema model, PGE(2)-induced hind paw edema model, and 12-O-tetradecanoyl-13-acetate (TPA)-induced mouse ear edema model and for the antinociceptive activity p-benzoquinone (PBQ)-induced writhing test in mice were employed. RESULTS The n-butanol extracts of Lamium garganicum subsp. laevigatum (LGL-BuOH), Lamium garganicum subsp. pulchrum (LGP-BuOH), and Lamium purpureum var. purpureum (LPP-BuOH) exhibited notable inhibition (16.5-28.9, 14.5-26.9, 12.3-21.5%, resp.) in carrageenan-induced hind paw edema model at doses of 200mg/kg without inducing any gastric damage. The LGL-BuOH (7.1-30.4%) and LGP-BuOH (5.9-24.1%) extracts also displayed potent anti-inflammatory activity against PGE(2)-induced hind paw edema model. LGL-BuOH and LGP-BuOH were also found to exhibit remarkable antinociceptive activity in p-benzoquinone-induced abdominal constriction test at a dose of 200 mg/kg (25.0 and 24.3%, respectively). CONCLUSION The experimental data demonstrated that Lamium garganicum subsp. laevigatum and Lamium garganicum subsp. pulchrum displayed remarkable anti-inflammatory and antinociceptive activities.

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.

Scalbidoside and albidoside, two iridoid glycosides from Scutellaria albida subsp. colchica

Abstract Two new iridoid glycosides, scalbidoside and albidoside were isolated from the methanolic extract of the aerial parts of Scutellaria albida subsp. colchica along with the known iridoid glucosides catalpol, globularin (= scutellarioside I), scutellarioside II and mussaenosidic acid. On the basis of chemical and spectral evidence, the structures of scalbidoside and albidoside were determined as 6′-O-(α- d -glucopyranosyl)-globularin and 6′-O-coumaroylmussaenosidic acid, respectively.

Physocalycoside, a new phenylethanoid glycoside from Phlomis physocalyx Hub.-Mor.

Abstract A new phenylethanoid tetraglycoside, physocalycoside (2), was isolated from the aerial parts of Phlomis physocalyx. Its structure was identified as 3-hydroxy-4-methoxy-β-phenyl-ethoxy-O-[α-ʟ-rhamnopyranosyl-(1→2)-α-ʟ-rhamnopyranosyl-(1→3)]-4-O-feruloyl-[β-ᴅ- glucopyranosyl-(1→6)]-|β-ᴅ-glucopyranoside, on the basis of spectroscopic evidence. In addition, one known iridoid glucoside, lamiide (1) and five known phenylethanoid glycosides, wiedemannioside C (3), verbascoside (= acteoside) (4). leucosceptoside A (5), martynoside (6), and forsythoside B (7) were also characterized. Compounds 2-7 demonstrated radical scavenging properties towards the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.

Iridoid and Phenylethanoid Glycosides from Phlomis tuberosa L.

Abstract A new iridoid glucoside, 8-O-acetylshanzhiside (1), was isolated from the aerial parts of Phlomis tuberosa, together with two known iridoid glucosides, shanzhiside methyl ester and lamalbide. The known phenylethanoid glycosides acteoside and forsythoside B were also obtained and characterized. The structure of 1 was determined by means of 1D - and 2DNMR spectroscopic evidence.

Iridoid and Phenylethanoid Glycosides from Phlomis longifolia var. longifolia

Abstract From the aerial parts of Phlomis longifolia var. longifolia four iridoid glucosides, shanzhiside methyl ester (1), 5-deoxypulchelloside I (2), lamalbide (3), phlomiol (4) and three phenylethanoid glycosides, verbascoside (5), forsythoside B (6). leucosceptoside A (7) along with the caffeic acid ester, chlorogenic acid (8) were isolated. The structures of the isolated compounds were established by spectroscopic (UV, IR, ID- and 2D-NMR, FABMS) and chemical evidence. The structure elucidation of the iridoid compounds 2 and 3 are discussed in detail.

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-β-ᴅ-glucopyranoside (1) was characterized along with the known neolignan glucosides, (D)-4-O-methyldehydrodiconiferyl alcohol-9′-O-β-ᴅ-glucopyranoside (= longifloroside A) (2) and (-)-dihydrodehydrodiconiferyl alcohol-9-O-β-ᴅ-glucopyranoside (3). The structure of the new compound was established on the basis of spectroscopic evidence

Secondary metabolites from Phlomis oppositiflora

In addition to rare phenylethanoid triglycosides, myricoside and its dimetylether derivative serratumoside A {3-hydroxy,4-methoxy-β-phenylethoxy-O-β-D-apiofuranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 3)-4-O-feruloyl-β-D-glucopyranoside}, a new phenylethanoid glycoside, myricoside-3′′′′-O-methylether {3,4-dihydroxy-β-phenylethoxy-O-β-D-apiofuranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 3)-4-O-feruloyl-β-D-glucopyranoside} along with a new neolignan glucoside, (7S, 8R)-dehydroconiferyl alcohol-8-5′-dehydroconiferyl aldehyde 4-O-β-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.

Iridoid Glucosides from Turkish Phlomis tuberosa

From the aerial parts of Phlomis tuberosa a new iridoid glucoside, chlorotuberoside was isolated together with five known iridoid glucosides, lamalbide, shanzhiside methyl ester, 7-epi-phlomiol (= phloyoside I), sesamoside and 5-deoxysesamoside. Two known phenylethanoid glycosides, forsythoside B, and decaffeoylacteoside, three known neolignan glycosides, dehydrodiconiferyl alcohol 9’-O-β -D-glucopyranoside, dihydrodehydrodiconiferyl alcohol 9-O-β -D-glucopyranoside and dihydrodehydrodiconiferyl alcohol 9’-O-β -D-glucopyranoside, one flavone glycoside, luteolin 7-O-β - D-glucopyranoside, as well as β -sitosterol 3-O-β -D-glucopyranoside and 1-methyl-O-β -D-glucopyranoside were also obtained and characterized. The structures of the isolates were elucidated on the basis of spectroscopic data. The three known phenylethanoid glycosides, verbascoside, leucosceptoside A and martynoside were identified by TLC comparison with authentic compounds.