Six New Secoiridoids from the Dried Fruits of Ligustrum lucidum

Aoki, Syota; Honda, Yurika; Kikuchi, Tomoyuki; Miura, T.; Sugawara, Ryo; Yaoita, Yasunori; Kikuchi, Masao; Machida, Koichi

doi:10.1248/cpb.60.251

Cited by 22 publications

(11 citation statements)

References 6 publications

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“…Nuezhenidic acid ( 6 ) is a reported secoiridiod glucoside in LLF [ 20 ], the content of which was demonstrated to have a significant increase after the LLF being processed with wine [ 47 ]. Nuezhenal A ( 8 ) and the 6′- O -cinnamoyl-8-epikingisidic acid isomers 36 and 40 are three recently discovered secoiridiod glucosides from LLF [ 21 ], and there are no references about them. These compounds were just tentatively identified base on the high mass accuracy (ppm < 5).…”

Section: Resultsmentioning

confidence: 99%

Application of UHPLC-ESI-Q-TOF-MS to Identify Multiple Constituents in Processed Products of the Herbal Medicine Ligustri Lucidi Fructus

Yao

Liu

et al. 2017

Molecules

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Ligustri Lucidi Fructus (LLF), the fruit of Ligustrum lucidum Ait. (Oleaceae), has been used as a common herbal medicine in clinical practice in China for nearly 2000 years. In most cases, LLF is prescribed in decoctions in the form of processed products rather than crude drugs. In this study, an ultra-high performance liquid chromatography coupled with electrospray ionization-quadrupole-time of flight-mass spectrometry (UHPLC-ESI-Q-TOF-MS) method was established for rapid separation and identification of multiple constituents in the 80% methanol extract of processed-LLF. A total of 50 compounds (one phenylethanoid, seven phenylethanoid glycosides, seven flavonoids, 25 iridoids, nine triterpenoids and one cyclohexanecarboxylic acid) were either unambiguously identified or tentatively characterized with the aid of authentic standards or published data. Luteolin-7-O-rutinoside, oleoside and secologanoside were detected in LLF for the first time. This study enriches the chemical profiling of processed-LLF and could provide valuable information for the quality control and further investigation of processed-LLF and crude LLF.

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Section: Resultsmentioning

confidence: 99%

Application of UHPLC-ESI-Q-TOF-MS to Identify Multiple Constituents in Processed Products of the Herbal Medicine Ligustri Lucidi Fructus

Yao

Liu

et al. 2017

Molecules

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“…Chemical structures of these compounds were readily determined by a combination of spectroscopic analysis and comparison with data described in the literature (Figure 1). Their NMR spectral data (available in the Supplementary Material) were well matched with those reported in the same NMR solvent [24].…”

Section: Resultsmentioning

confidence: 56%

Evaluation of MMP Inhibitors Isolated from Ligustrum japonicum Fructus

et al. 2019

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The current study investigated the ability of two secoiridoids, GL-3 (1) and oleonuezhenide (2), isolated from the fruits of Ligustrum japonicum to inhibit MMP-2 and -9 activity in phorbol 12-myristate 13-acetate (PMA)-induced HT-1080 human fibrosarcoma cells. Both compounds 1 and 2 were able to exert lowered gelatin digestion activity for MMP-2 and -9 tested by gelatin zymography via suppressing the release of MMPs to culture medium according to ELISA results. Treatment with compounds was also able to suppress the expression of both mRNA and protein levels of MMP-2 and -9. Action mechanism behind the MMP inhibitory effect of the compounds was suggested to be via MAPK pathway indicated by decreased levels of phosphorylated p38, ERK and JNK proteins evaluated employing immunoblotting. Compound 1 was shown to be slightly more active to inhibit MMP-2 and -9, however, compound 2 showed more regular dose-dependency during inhibition. In conclusion, this study suggested that GL-3 and oleonuezhenide were notable natural origin potent MMP inhibitors and could serve as lead compounds for development of anti-invasive MMP inhibitors against tumor metastasis.

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“…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

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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.

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Six New Secoiridoids from the Dried Fruits of Ligustrum lucidum

Cited by 22 publications

References 6 publications

Application of UHPLC-ESI-Q-TOF-MS to Identify Multiple Constituents in Processed Products of the Herbal Medicine Ligustri Lucidi Fructus

Application of UHPLC-ESI-Q-TOF-MS to Identify Multiple Constituents in Processed Products of the Herbal Medicine Ligustri Lucidi Fructus

Evaluation of MMP Inhibitors Isolated from Ligustrum japonicum Fructus

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

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