Pedunculoside

Inhibitory activity of chemical constituents from Arenaria serpyllifolia on nitric oxide production.[Pubmed: 23670630]

Planta Med. 2013 May;79(8):687-92.

Five new compounds, including one new xanthone, 1-hydroxy-5-methoxyxanthone 6-O-β-D-glucopyranoside (1), one new lignan, 3-(β-D-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-acetoxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (2), and three new γ-pyrones, japonicumone A 4'-O-β-D-glucopyranoside (3), japonicumone B 3'-O-β-D-glucopyranoside (4), and japonicumone B 4'-O-β-D-glucopyranoside (5), together with eight known compounds (6-13) were isolated from the whole plants of Arenaria serpyllifolia.
METHODS AND RESULTS:
Their structures were elucidated on the basis of extensive spectroscopic analysis (UV, IR, HRESIMS, 1D- and 2D-NMR, and CD) as well as chemical methods. The isolated compounds were evaluated for their inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW 264.7 macrophages. Compounds 1-5, sacranoside A (9), and Pedunculoside (13) showed potential nitric oxide inhibitory activities with IC50 values ranging from 14.92 µM to 52.23 µM.

Hypolipidemic Activity of Pedunculoside, A Constituent of Ilex doniana.[Reference: WebLink]

Pharm. Biol.,1999, 37(1):37- 41.

Pedunculoside, an ester glucoside of 3ß, 19a, 23-trihydroxyurs-12-en-28-oic acid, was isolated from the leaves of Ilex doniana DC. On dietary administration to hyperlipidemic albino rats, it showed significant hypocholesterolemic activity.

PLoS One. 2014 Jul 11;9(7):e101761.

A water-soluble inclusion complex of pedunculoside with the polymer β-cyclodextrin: a novel anti-inflammation agent with low toxicity.[Pubmed: 25013908]

More than 50% of new drug candidates in drug discovery are lipophilic and exhibit poor aqueous solubility, which results in poor bioavailability and a lack of dose proportionality.
METHODS AND RESULTS:
Here, we improved the solubility of Pedunculoside (PE) by generating a water-soluble inclusion complex composed of PE and the polymer β-cyclodextrin (CDP). We characterized this novel complex by 1H NMR, FT-IR, UV-vis spectroscopy, powder X-ray diffractometry and thermogravimetric analysis. The ratio of β-cyclodextrin (β-CD) units in CDP to PE was determined to be 2∶1. The KD value of the inclusion complex was determined to be 4.29×10(-3) mol•L(-1). In contrast to the low solubility of PE, the water-solubility of the PE-CDP complex was greatly enhanced. A preclinical toxicological study indicated that PE-CDP was well tolerated for a single administration. Importantly, the anti-inflammation potency of the PE-CDP complex was higher than that of PE.
CONCLUSIONS:
As a result, the formation of inclusion complexes by water-soluble CDP opens up possible aqueous applications of insoluble drug candidates in drug delivery.

J Liq Chromatogr Relat Technol. 2014 Feb 1;37(4):572-587.

Enrichment and purification of pedunculoside and syringin from the barks of Ilex rotunda with macroporous resins.[Pubmed: 25104900]

Jiubiying, the dried barks of Ilex rotunda Thunb. (Aquifoliaceae), has been used as herbal tea and traditional Chinese medicine for heat-clearing, detoxifying, dehumidification, and odynolysis. Pedunculoside and syringin are two main bioactive components.
METHODS AND RESULTS:
For the new drug development, we tried to isolate and purify several chemical constituents from Jiubiying by high-speed counter-current chromatography (HSCCC). The two-phase solvent system used was composed of ethyl acetate-n-butanol-water (1:6:7, v/v/v). From 1.0 g of Jiubiying extracts syringaresinol 4',4″-bis-O-β-D- glucopyranoside (I, 20.2 mg), syringin (II, 56.8 mg), sinapaldehyde glucoside (III, 26.2 mg), syringaresinol 4'-O-β-D-glucopyranoside (IV, 20.4 mg), and Pedunculoside (V, 45.1 mg) were obtained by one run of TBE-1000A HSCCC machine with 1000 mL of column volume.
CONCLUSIONS:
Their structures were identified by IR, MS, and extensive NMR studies. Syringaresinol 4',4″-bis-O-β-D-glucopyranoside (I) was isolated from this plant for the first time.