Eleven New Triterpenoid Glycosides from the Roots of Ilex asprella.

Asprellosides A-K, nine new ursane-type triterpenoid glycosides (1-9), and two new oleanane-type triterpenoid glycosides (10 and 11), including six rare sulfated triterpenoid glycosides, were isolated from the roots of Ilex asprella. Their structures were determined on the basis of comprehensive spectroscopic analysis and chemical methods. Among these compounds, asprelloside B (2) and asprelloside C (3) are the first examples of triterpenoid glycosides bearing a rare 3,4-O-disulfo-xylopyranosyl residue. All the saponins isolated showed no significant effects against respiratory syncytial virus (RSV) and lipopolysaccharide-induced nitric oxide production in Raw264.7 macrophages.

[A new oleanane-type triterpenoid glycoside from roots of Ilex asprella].

A new δ-oleanane-type triterpenoid glycoside, 3-O-(3-O-sulfo)-ß-D-glucopyranosiduronic acid 3ß-hydroxy-13(18)-oleanen- 28-oic acid 28-ß-D-glucopyranosyl ester (1), along with ten known triterpenoid glycosides, rotundinoside A (2), oblonganoside M (3), 3-O-ß-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl 3ß,19α-dihydroxy-20α- urs-12-en-28-oic acid 28-O-ß-D- glucopyranosyl ester (4), ilexsaponin B2 (5), ilexside Ⅱ (6), rotundinoside B (7), ilekudinoside B (8), ilexpublesnin E (9), ilekudinoside D (10) and ilexpernoside D (11), was isolated from the 75% ethanol extract of the roots of Ilex asprella by various chromatographic separation. Their structures were identified on the basis of MS, NMR spectroscopic analysis and chemical methods. In addition, 2-11 were isolated from I. asprella for the first time.

[A new flavonoid glycoside from leaves of Eucalyptus robusta].

A new flavonoid glycoside, (-)-2S-8-methyl-5,7,4'-trihydroxyflavanone-7-O-ß-D-glucopyranoside (1), along with five known ones, quercetin-3-O-(2"-galloyl)-α-L-arabinoside (2), kaempferol-3-O-α-L-arabinoside (3), guaijaverin (4), trifolin (5) and hyperin (6), was isolated from the leaves of Eucalyptus robusta. Their structures with absolute configurations were elucidated by NMR, HR-ESI-MS, CD spectra data and physicochemical methods. In addition, 2-6 were isolated from E. robusta for the first time.

Crude triterpenoid saponins from Anemone flaccida (Di Wu) exert anti-arthritic effects on type II collagen-induced arthritis in rats.

BACKGROUND: Anemone flaccida Fr . Schmidt (Ranunculaceae) (Di Wu in Chinese) is used to treat punch injury and rheumatoid arthritis (RA). However, the active compounds and underlying mechanism of action mediating the anti-arthritic effects of A. flaccida remain unclear. This study aims to evaluate the underlying action mechanism of A. flaccida crude triterpenoid saponins (AFS) on RA using a type II collagen (CII)-induced arthritis (CIA) rat model, and to assess the anti-inflammatory effects of the main active compounds of AFS, namely flaccidoside II, anhuienoside E, glycoside St-I4a, hemsgiganoside B, hederasaponin B, and 3-O-α-l-rhamnopyranosyl (1 â†’ 2)-ß-d-glucopyranosyl oleanolic acid 28-O-ß-d-glucopyranosyl (1 â†’ 6)-ß-d-glucopyranosyl ester. METHODS: Male Wistar rats (n = 50) were randomly separated into five groups (n = 10) and immunized by CII injection. AFS (200 or 400 mg/kg) and dexamethasone were orally administered for 30 days after establishing the model. The arthritis severity was assessed by paw volume using a plethysmometer. After 30 days of treatment, the right hind paws of the rats were obtained. Paw histology was analyzed by hematoxylin and eosin staining, and radiologic imaging was performed by micro-computed tomography. MTT assays were used to evaluate the cytotoxicity of AFS and its main compounds in RAW264.7 cells. Enzyme-linked immunosorbent assay kits were used to measure interleukin (IL)-6 and tumor necrosis factor (TNF)-α in serum and supernatants from AFS- and main AFS compound-treated RAW264.7 cells stimulated by lipopolysaccharide (LPS). RESULTS: Anemone flaccida crude triterpenoid saponins inhibited redness and swelling of the right hind paw in the CIA model. Radiological and histological examinations indicated that inflammatory responses were reduced by AFS treatment. Moreover, comparing with untreated rats, serum TNF-α (P = 0.0035 and P < 0.001) and IL-6 (P = 0.0058 and P = 0.0087) were lower in AFS-treated CIA rats at the dose of 200 and 400 mg/kg/day. AFS and its main compounds, including hederasaponin B, flaccidoside II, and hemsgiganoside B, significantly inhibited TNF-α (P = 0.0022, P = 0.013, P = 0.0015, and P = 0.016) and IL-6 (P = 0.0175, P < 0.001, P < 0.001, and P < 0.001) production in LPS-treated RAW264.7 cells, respectively. CONCLUSIONS: Anemone flaccida crude triterpenoid saponins and its main bioactive components, including hederasaponin B, flaccidoside II, and hemsgiganoside B, decreased pro-inflammatory cytokine levels in a CIA rat model and LPS-induced RAW264.7 cells.