Secoiridoid glucosides from Fraxinus malacophylla

He, Zheng-Dan; Ueda, Shinichi; Inoue, Ken‐ichiro; Akaji, Masako; Fujita, Tetsuro; Yang, Chong‐Ren

doi:10.1016/s0031-9422(00)90529-6

Cited by 8 publications

(3 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The structures of these secoiridoids were established by MS, 1 H- and 13 C-NMR and verified by comparing the NMR data (see the Supplementary Materials ) with values reported in the literature. They were thus identified as GI3 ( 1 ) [ 26 ], nuzhenide ( 3 ) [ 27 ], ligstroside ( 4 ) [ 28 ], oleoside-11-methyl ester ( 5 ) [ 29 ], oleuricine A ( 6 ) [ 30 ], nicotiflorine ( 7 ) [ 31 , 32 ], jaspolyanoside ( 8 ) [ 33 ], oleopolynuzhenide A ( 9 ) [ 34 ], safghanoside G ( 10 ) [ 35 ], excelside B ( 11 ) [ 21 ], isooleonuezhenide ( 12 ) [ 36 ], lucidumoside A ( 13 ) [ 37 ], safghanoside A ( 14 ) [ 38 ], jaspolyoleoside B ( 15 ) [ 38 ], 10-hydroxoleoside-7,11-dimethyl ester ( 16 ) [ 39 ], GI5 ( 29 ) [ 40 ], oleoside-7,11-dimethyl ester ( 31 ) [ 41 ], isolignstroside ( 35 ) [ 42 ], 10-hydroxyligstroside ( 36 ) [ 43 ]. All the secoiridoids were found in F. mandshurica seeds in the form of glycosides.…”

Section: Resultsmentioning

confidence: 99%

Anti-Obesity and Gut Microbiota Modulation Effect of Secoiridoid-Enriched Extract from Fraxinus mandshurica Seeds on High-Fat Diet-Fed Mice

Guo

Zhao

et al. 2020

Molecules

View full text Add to dashboard Cite

Previously we conducted a phytochemical study on the seeds of Fraxinus excelsior and isolated nine secoiridoid compounds with adipocyte differentiation inhibitory activity and peroxisome proliferator activated receptor alpha (PPARα) activation effects. However, the bioactive constituents and functions of Fraxinus mandshurica seeds have not been studied. In the present study, we investigated the secoiridoid compounds in F. mandshurica seed extract (FM) using column chromatography, 1H-NMR, 13C-NMR and HPLC-DAD methods. The pancreatic lipase inhibitory activities of isolated compounds were evaluated in vitro. Additionally, the anti-obesity and gut microbiota modulation effect of FM on high-fat diet-induced obesity in C57BL/6 mice were also studied in vivo. The results showed that 19 secoiridoids were isolated from FM and identified. The total content of secoiridoids in FM reached 181.35 mg/g and the highest content was nuzhenide (88.21 mg/g). All these secoiridoid compounds exhibited good pancreatic lipase inhibitory activity with inhibition rate ranged from 33.77% to 70.25% at the concentration of 100 μM. After obese mice were administrated with FM at 400 mg/kg.bw for 8 weeks, body weight was decreased by 15.81%. Moreover, FM could attenuate the lipid accumulation in serum and liver, relieve the damage in liver and kidney, and extenuate oxidative stress injury and inflammation caused by obesity in mice. FM could also modulate the structural alteration of gut microbiota in obese mice, increasing the proportion of anti-obesity gut microbiota (Bacteroidetes, Bacteroidia, S24-7 and Allobaculum), and reducing the proportion of obesogenic gut microbiota (Firmicutes and Dorea). This study suggests that F. mandshurica seeds or their secoiridoids may have potential for use as a dietary supplement for obesity management.

show abstract

Section: Resultsmentioning

confidence: 99%

Anti-Obesity and Gut Microbiota Modulation Effect of Secoiridoid-Enriched Extract from Fraxinus mandshurica Seeds on High-Fat Diet-Fed Mice

Guo

Zhao

et al. 2020

Molecules

View full text Add to dashboard Cite

show abstract

“…Compound (Shen et al, 1996) (He et al, 1994). These compounds are more soluble in methanol and DMSO, but insoluble in several medium and less polar organic solvents (petroleum ether, dichloromethane and ethyl acetate).…”

Section: Discussionmentioning

confidence: 99%

Chemical characterization, multivariate analysis and comparison of biological activities of different parts of Fraxinus mandshurica

Guo,

Liu,

Guo

et al. 2024

Biomedical Chromatography

View full text Add to dashboard Cite

Fraxinus mandshurica (Oleaceae) is used as a traditional medicinal plant for the treatment of red eyes, menstrual disorders, excessive leucorrhea, chronic bronchitis and psoriasis. To perform chemical characterization of the secondary metabolites of F. mandshurica roots, bark, stems and leaves, 32 samples were collected from eight provinces in this study. A total of 64 chemical components were detected from four different parts of F. mandshurica by ultra‐performance liquid chromatography–quadrupole time‐of‐flight mass spectrometry. Meanwhile, a total of nine secoiridoids were obtained by natural product chemical extraction, isolation and identification methods. Quantitative analysis by high‐performance liquid chromatography–diode array detection–mass spectrometry showed the highest total content of secoiridoids in the bark, which is also consistent with the traditional medicinal parts. The results of methodological validation showed that the correlation coefficient (R2) values were all >0.9993, indicating a good linear range of the standard curve, while the relative standard deviations of precision, reproducibility and stability were <3%, and the spiked recoveries ranged from 98.22 to 102.27%, indicating that the experimental method was reliable and stable. In addition, fingerprinting and a heatmap were established to demonstrate the content trends of F. mandshurica more visually from different origins. Multivariate analysis, including principal component analysis and partial least squares discriminant analysis, was performed to determine the chemical characteristics of different parts of F. mandshurica, and six characteristic secoiridoids that could be used to distinguish different origins were screened. Finally, the inhibition of tyrosinase, α‐glucosidase, acetylcholinesterase and pancreatic lipase activities by the nine characteristic compounds and extracts from different parts were investigated, and the results showed that they all exhibited different degrees of enzyme activity inhibition and thus have potential applications in whitening and blemish removal, hypoglycemia, anti‐Alzheimer's disease and anti‐obesity as a new source of natural enzyme activity inhibitors. This study establishes an identification and evaluation method applicable to phytochemistry of different origins, which is a guideline for quality control, origin evaluation and clinical application of traditional medicinal plants. This is also an unprecedented study on the identification of the chemical composition of different parts of F. mandshurica, characteristic compounds and the inhibition of enzyme activity of extracts from different parts.

show abstract

“…Secoiridoids arouse general interest especially due to repeated discoveries of new structures. A number of new compounds of this type have also been found in plants from the family Oleaceae (Inoue et al 1991;Kuwajima et al 1992;Calis et al 1993;Shen et al 1993;Zheng-Dan He et al 1994;Damtoft et al 1994). A number of new compounds of this type have also been found in plants from the family Oleaceae (Inoue et al 1991;Kuwajima et al 1992;Calis et al 1993;Shen et al 1993;Zheng-Dan He et al 1994;Damtoft et al 1994).…”

Section: Secondary Metabolitesmentioning

confidence: 99%

Medicinal and Aromatic Plants IX

Bajaj¹

1996

Biotechnology in Agriculture and Forestry

View full text Add to dashboard Cite

Secoiridoid glucosides from Fraxinus malacophylla

Cited by 8 publications

References 3 publications

Anti-Obesity and Gut Microbiota Modulation Effect of Secoiridoid-Enriched Extract from Fraxinus mandshurica Seeds on High-Fat Diet-Fed Mice

Anti-Obesity and Gut Microbiota Modulation Effect of Secoiridoid-Enriched Extract from Fraxinus mandshurica Seeds on High-Fat Diet-Fed Mice

Chemical characterization, multivariate analysis and comparison of biological activities of different parts of Fraxinus mandshurica

Medicinal and Aromatic Plants IX

Contact Info

Product

Resources

About