Three New Iridoid Glucosides from the Roots of Patrinia scabra

Di, Lijun; Li, Ning; Zu, Ling-Bo; Wang, Kai‐Jin; Zhao, You‐Xing; Wang, Zhi

doi:10.5012/bkcs.2011.32.9.3251

Cited by 15 publications

(17 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The chemical structures of isolates were elucidated to be loganic acid ( 1 ), swertiamarin ( 2 ), gentiopicroside ( 3 ), macrophylloside D ( 4 ) and 2‐methoxyanofinic acid ( 5 ). The 1 H NMR, 13 C NMR and MS spectroscopic data were in good agreement with those of previously reported values .…”

Section: Resultssupporting

confidence: 91%

Efficient methods for isolating five phytochemicals from Gentiana macrophylla using high‐performance countercurrent chromatography

Rho

Jung

Lee

et al. 2016

J of Separation Science

View full text Add to dashboard Cite

Efficient high-performance countercurrent chromatography methods were developed to isolate five typical compounds from the extracts of Gentiana macrophylla. n-Butanol-soluble extract of G. macrophylla contained three hydrophilic iridoids, loganic acid (1), swertiamarin (2) and gentiopicroside (3), and a chromene derivative, macrophylloside D (4) which were successfully isolated by flow rate gradient (1.5 mL/min in 0-60 min, 5.0 mL/min in 60-120 min), and consecutive flow rate gradient HPCCC using n-butanol/0.1% aqueous trifluoroacetic acid (1:1, v/v, normal phase mode) system. The yields of 1-4 were 22, 16, 122, and 6 mg, respectively, with purities over 97% in a flow rate gradient high-performance countercurrent chromatography, and consecutive flow rate gradient high-performance countercurrent chromatography gave 1, 2, 3 (54, 41, 348 mg, respectively, purities over 97%) and 4 (13 mg, purity at 95%) from 750 mg of sample. The main compound in methylene chloride soluble extract, 2-methoxyanofinic acid, was successfully separated by n-hexane/ethyl acetate/methanol/water (4:6:4:6, v/v/v/v, flow-rate: 4 mL/min, reversed phase mode) condition. The structures of five isolates were elucidated by H, C NMR and ESI-Q-TOF-MS spectroscopic data which were compared with previously reported values.

show abstract

Section: Resultssupporting

confidence: 91%

Efficient methods for isolating five phytochemicals from Gentiana macrophylla using high‐performance countercurrent chromatography

Rho

Jung

Lee

et al. 2016

J of Separation Science

View full text Add to dashboard Cite

show abstract

“…Among these isolates, only compound 10 showed cytotoxicity against the HeLa cell line, with an IC 50 value of 24.5 μM. Compounds 1,[4][5][6]8,and 18 showed cytotoxic activities against the MNK-45 cell line with respective IC 50 values of 15.6, 8.7, 9.4, 30.9, 23.8, and 11.2 μM, whereas the other compounds were inactive. As can be seen from the cytotoxicity results in comparison with the inactive compounds (2, 3, 7, 9−17, and 19), glycosylation at the C-1 position plays an important role in cytotoxicity against MNK-45 cells.…”

Section: ■ Results and Discussionmentioning

confidence: 93%

Cytotoxic Iridoids from the Roots of Patrinia scabra

Gao

et al. 2012

J. Nat. Prod.

Self Cite

View full text Add to dashboard Cite

Six new iridoid glucosides, patriridosides D-I (1-6), and one new iridoid, scabrol A (7), along with 12 known non-glycosidic and glycosidic iridoids (8-19), have been isolated from an ethanolic extract of the roots of Patrinia scabra. The cytotoxic activity of the isolated compounds against human cervical carcinoma HeLa cells and gastric carcinoma MNK-45 cells was evaluated using the MTT assay. Compounds 1, 4-6, 8, and 18 showed cytotoxic activities against the MNK-45 cell line with respective IC₅₀ values of 15.6, 8.7, 9.4, 30.9, 23.8, and 11.2 μM, while only compound 10 showed cytotoxicity against the HeLa cell line, with an IC₅₀ value of 24.5 μM.

show abstract

“…To identify the main constituent of the GL-B-03 sub-fraction, it was subjected to RP-18 column chromatography and was eluted with acetonitrile in H 2 O (0.05% trifluoroacetic acid) in a step-gradient manner (10% to 40%) to produce the bioactive component, which was identified as a single compound, loganic acid, whose molecular formula is C 16 H 24 O 10 . The identification was accomplished by the analysis of 1D and 2D nuclear magnetic resonance and mass spectrometry data, along with a comparison being made with those in the literature [ 19 ] ( Figure 2 ).…”

Section: Resultsmentioning

confidence: 99%

Antiadipogenic Effects of Loganic Acid in 3T3-L1 Preadipocytes and Ovariectomized Mice

et al. 2018

View full text Add to dashboard Cite

Obesity is caused by an excess storage of body fat, resulting from a chronic imbalance between energy intake and expenditure. Gentiana lutea L. (GL) root has been reported to reduce lipid accumulation in the aortic wall of diabetic rats. Here, we performed fractionation and isolation of the bioactive constituent(s) that may be responsible for the antiadipogenic effects of the GL root extract. A single compound, loganic acid, was identified as a candidate component in the 30% ethanol extract of GL. Loganic acid treatment significantly decreased the adipocyte differentiation of 3T3-L1 preadipocytes in a dose-dependent manner. The expression of key adipogenesis-related genes such as adiponectin (Adipoq), peroxisome proliferator-activated receptor gamma (Pparg), lipoprotein lipase (Lpl), perilipin1 (Plin1), fatty acid binding protein 4 (Fabp4), glucose transporter type 4 (Slc2a4), CCAAT/enhancer-binding protein alpha (Cebpa), and tumor necrosis factor-alpha (Tnf) were significantly reduced following treatment with loganic acid. In vivo experiments in an ovariectomy-induced obesity mouse model showed that loganic acid (oral administration with 10 and 50 mg/kg/day) significantly inhibited body weight gain, total fat increase, fatty hepatocyte deposition in the liver, and adipocyte enlargement in the abdominal visceral fat tissues. These results suggest that loganic acid in the GL root extract has antiadipogenic effects in vitro and in vivo. Loganic acid may be beneficial for the prevention and treatment of obesity, particularly in menopausal obese women.

show abstract

Three New Iridoid Glucosides from the Roots of Patrinia scabra

Cited by 15 publications

References 8 publications

Efficient methods for isolating five phytochemicals from Gentiana macrophylla using high‐performance countercurrent chromatography

Efficient methods for isolating five phytochemicals from Gentiana macrophylla using high‐performance countercurrent chromatography

Cytotoxic Iridoids from the Roots of Patrinia scabra

Antiadipogenic Effects of Loganic Acid in 3T3-L1 Preadipocytes and Ovariectomized Mice

Contact Info

Product

Resources

About