Kuo Xu

Bioactive Sesquiterpenoid and Polyacetylene Glycosides from Atractylodes lancea.

Nine new sesquiterpenoids (1-9), five new polyacetylenes (10-14), and six known compounds were isolated from the rhizomes of Atractylodes lancea. These new chemical structures were established using NMR, MS, and ECD data. Notably, compounds 3-5, the aglycone of which possesses two stereogenic centers (C-5 and C-7), exhibited similar ECD spectra to compounds 1 and 2, the aglycone of which possesses one stereogenic center (C-7). Such a difference was supported by the experimental and calculated ECD data and single-crystallographic analyses of 3a. In addition, compound 3 inhibited lipopolysaccharide-induced NO production in BV2 cells with an IC50 value of 11.39 μM (positive control curcumin, IC50 = 4.77 μM); compound 4 showed better hepatoprotective activity against N-acetyl-p-aminophenol-induced HepG2 cell injury than the positive drug (bicyclol) at a concentration of 10 μM (p < 0.001).

Direct Assignment of the Threo and Erythro Configurations in Polyacetylene Glycosides by 1H NMR Spectroscopy

An approach for discriminating the threo and erythro configurations of polyacetylene glycosides by 1H NMR spectroscopy was developed. Using acetic acid-d4/D2O as the solvent, a relatively larger 3JHH value (7.0 Hz) for the acyclic vicinal diol group was unambiguously assigned to the threo configuration, whereas the smaller value (3.5 Hz) was assigned to the erythro configuration. This convenient method requires no hydrolysis or derivatization and is suitable for micromolar concentrations of polyacetylene glycosides. The underlying mechanism is discussed via visualized conformations.

Six new compounds from Atractylodes lancea and their hepatoprotective activities

Two new phenolic glycosides with a rare β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl moiety (1, 2), one new dihydrobenzofuran derivative (3), one new pyrazine derivative (4), two new furofuran lignan glycosides (5, 6), and six known compounds (7-12) were isolated from the rhizomes of Atractylodes lancea. The structures of these compounds were elucidated by extensive spectroscopic analyses combined with the experimental and calculated electronic circular dichroism and the Rh2(OCOCF3)4-induced circular dichroism for configurational assignments. Notably, compounds 1-3 showed significant hepatoprotective activities against N-acetyl-p-aminophenol-induced HepG2 cell injury. This study is also the first Letter on the isolation of furofuran lignans and pyrazine derivatives (4-7) from the genus Atractylodes.

Four new C10-polyacetylene glycosides from the rhizomes of Atractylodes lancea

Abstract An ongoing phytochemical investigation of the rhizomes of Atractylodes lancea resulted in the isolation of four new C10-type polyacetylene glycosides (1−4). Their structures were elucidated on the basis of extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HRESIMS). The absolute configurations of compounds 2−4 were determined by comparing the specific rotations of their aglycones. Notably, compounds 2 and 3 exhibited significant hepatoprotective activities against APAP-induced HepG2 cell injury at a concentration of 10 μM. Compounds 2 and 3 showed weak anti-inflammatory effects on LPS-induced NO production in microglia BV2 cells at a concentration of 10 μM.

Eight new eudesmane- and eremophilane-type sesquiterpenoids from Atractylodes lancea

Phytochemical and pharmacological study on the rhizomes of Atractylodes lancea led to the identification of twenty-one compounds: six new eudesmane-type sesquiterpenoids (1-6), two new eremophilane-type sesquiterpenoids (7, 8), and thirteen known compounds (9-21). These new compounds were elucidated using extensive spectroscopic analyses with experimental and calculated electronic circular dichroism (ECD) for the configurational assignments. Notably, this study was the first report on the isolation of two eremophilane-type sesquiterpenoids (7, 8) from the genus Atractylodes. Compounds 5, 7, and 16 showed potent hepatoprotective activities against N-acetyl-p-aminophenol (APAP)-induced HepG2 cell injury at a concentration of 10μM (bicyclol as the positive drug).

Two new thiophene polyacetylene glycosides from Atractylodes lancea

Abstract Phytochemical investigation on the rhizomes of Atractylodes lancea led to the isolation of two new thiophene polyacetylene glycosides (1 and 2) and six known compounds (3-8). Their structures were elucidated based on the extensive spectroscopic data (UV, IR, 1D and 2D NMR, and HRESIMS). The absolute configurations of new compounds were established by calculated and experimental circular dichroism. All the compounds were assessed on the lipopolysaccharide-induced NO production in BV2 cells and compounds 3, 7, and 8 showed moderate inhibitory activities.