Search

Phytochemical investigation on the whole plants of Iris japonica led to the isolation of four new aromatic glycosides. Their structures including the absolute configurations were determined by spectroscopic and chemical methods as (-)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (1), (-)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (2), (-)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7R,8R)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (3), (-)-4-hydroxy-3-methoxy acetophenone 4-O-β-d-{6-O-[4-O-(7S,8S)-(4-hydroxy-3-methoxyphenylglycerol-8-yl)-3-methoxybenzoyl]}-glucopyranoside (4), respectively.

Nine new compounds, together with 16 known analogs, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of their spectroscopic data and chemical evidence. In addition, the new compounds were tested for their hepatoprotective activities against APAP-induced HepG2 cell damage and their ability to inhibit LPS-induced nitric oxide production in the murine microglia BV2 cell line. Compounds 2 and 5 exhibited pronounced hepatoprotective activities against APAP-induced HepG2 cell damage at a concentration of 10 μM, and compounds 4 and 9 showed moderate inhibitory activity against microglial inflammation factor with IC50 values of 3.51 and 7.11 μM, respectively.

Eleven flavonol glycosides were isolated from the ethanol extract of Lysimachia clethroides by a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Their structures were identified as astragalin (1), isoquercitrin (2), isorhamnetin-3-O-β-D-glucopyranoside (3), quercetin-3-O-β-D-6"-acetylglucopyranoside (4), quercetin-7-O-β-D-glucopyranoside (5), prunin (6), 2-hydroxynaringin-5-O-β-D-glucopyranoside (7), kaempferol-3-O-rutinonoside (8), kaempferol-3-O-robinobioside (9), rutin (10) and kaempferol-3,7-di-O-β-D-glucopyranoside (11). Among them, compounds 4, 7 and 11 were obtained from the Lysimachia genus for the first time, while compounds 3, 5 and 9 were firstly reported from this plant. In the preliminary assays, compounds 2, 6 and 8 possessed significant inhibition against aldose reduc- tase, with IC50 values of 2.69, 1.00, 1.80 μmol · L(-1), respectively; none of compounds 1-11 exhibited obvious cytotoxic activity (IC50 > 10 μmol · L(-1)).

Four new ionone and ionone glycosides (1-4), and a new monoterpene (5), together with 10 known analogues (6-15), were isolated from the air-dried roots of Rehmannia glutinosa. The structures of these compounds were elucidated on the basis of spectroscopic data analysis. Furthermore, in in vitro assays, compound 3 (10 μM) exhibited moderate hepatoprotective activities against d-galactosamine-induced HL-7702 cell damage.

Eleven new iridoid glycosides, rehmaglutosides A-K (1-11), together with 20 known analogues were isolated from the air-dried roots of Rehmannia glutinosa. The structures of these compounds were elucidated on the basis of spectroscopic data analysis and chemical evidence. Furthermore, in in vitro assays, compounds 3, 7, and 9-11 (10 μM) exhibited moderate hepatoprotective activities against D-galactosamine-induced HL-7702 cell damage.

A new acylated flavonol glycoside, kaempferol-3-O-β-D-(2-feruloylglucopyranosyl) (1 → 6)-[β-D-glucopyranosyl(1 → 2)]-β-D-glucopyranoside, named tangutorumoside A (1), together with 12 known compounds, was isolated from 50% acetone extract of Cardamine tangutorum. Their structures were elucidated by NMR and MS experiments. In addition, compound 1 could promote the proliferation of splenic lymphocytes and thymic lymphocytes with ConA in vitro.

Three new flavonoid glycosides, named 7,8,4'-trihydroxy-3,5-dimethoxy-6-methylflavonol-8-O-β-D-glucopyranoside (1), 5,7,4'-trihydroxy-3-methoxy-6-methylflavonol-7-O-β-D-glucopyranoside (2), 3,5,7,4'-tetrahydroxy-6-methylflavonol-7-O-β-D-glucopyranoside (3), together with two known flavonoid glycosides were isolated from the needles of Pinus tabulaeformis Carr. Their structures were established on the basis of various spectroscopic analyses.

Abstract: Three 6H-dibenzo[b,d]pyran-6-one glycosides named lysilactones A–C (1–3) were isolated from the aerial parts of Lysimachia clethroides. Their structures were elucidated using spectroscopic analysis and chemical evidence. This is the first report of 6H-dibenzo[b,d]pyran-6-one glycosides. Furthermore, we have finished a total synthesis of lysilactone A. The key step is a Suzuki coupling used for the construction of the central biaryl bond. Lysilactone A was prepared in eight steps starting from phloroglucinic acid and orcinol, where the longest linear sequence is seven steps. [Copyright &y& Elsevier]