Oleoside Dimethyl Ester Research Articles

Inhibitory Effect of LGS and ODE Isolated from the Twigs of Syringa oblata subsp. dilatata on RANKL-Induced Osteoclastogenesis in Macrophage Cells.

Osteoblasts and osteoclasts play a pivotal role in maintaining bone homeostasis, of which excessive bone resorption by osteoclasts can cause osteoporosis and various bone diseases. However, current osteoporosis treatments have many side effects, and research on new treatments that can replace these treatments is ongoing. Therefore, in this study, the roles of ligustroside (LGS) and oleoside dimethylester (ODE), a natural product-derived compound isolated from Syringa oblata subsp. dilatata as a novel, natural product-derived osteoporosis treatments were investigated. In the results of this study, LGS and ODE inhibited the differentiation of receptor activator of nuclear factor kappa-Β ligand (RANKL)-induced RAW264.7 cells into osteoclasts without cytotoxicity, and down-regulated the activity of TRAP, a specific biomarker of osteoclasts. In addition, it inhibited bone resorption and actin ring formation, which are important functions and features of osteoclasts. Also, the effects of LGS and ODE on the mitogen-activated protein kinase (MAPK) and nuclear factor kappa-light-chain-enhancer of activated B (NF-κB) and phosphoinositide 3-kinases (PI3K)/ protein kinase B (Akt)/mechanistic target of rapamycin (mTOR) signaling pathways that play important roles in osteoclast differentiation were evaluated. In the results, LGS and ODE downregulated the phosphorylation of RANKL-induced MAPK and PI3K/Akt/mTOR proteins in a concentration-dependent manner, translocation of NF-κB into the nucleus was inhibited. As a result, the compounds LGS and ODE isolated from S. oblate subsp. dilatata effectively regulated the differentiation of RANKL-induced osteoclasts and inhibited the phosphorylation of signaling pathways that play a pivotal role in osteoclast differentiation. Therefore, these results suggest the possibility of LGS and ODE as new natural product treatments for bone diseases caused by excessive osteoclasts.

Molecular modeling of non-covalent binding of Ligustrum lucidum secoiridoid glucosides to AP-1/matrix metalloproteinase pathway components.

Ligustrum lucidum secoiridoid glucosides have been demonstrated to treat various types of diseases such as inflammation, pain, hepatotoxicity and hyperlipidermic as well as tonic for liver and kidney. Matrix metalloproteinases (MMPs) play a key role upon the pathology of photoaging. The present computational study showed that among the six secoiridoid glucosides (ligustroside, lucidumoside A, lucidumoside C, neonuezhenide, oleoside dimethylester, and oleuropein), ligustroside and lucidumoside A competitively inhibit all MMP-1, MMP-3, and MMP-9 activities in the docking models. The molecular docking analysis revealed a network of interactions between MMP-1, MMP-3, and MMP-9 and the ligands; ligustroside and lucidumoside A, and oxygen-containing and hydrophobic functional groups appear to be responsible for these enhanced interactions. The effect of ligustroside and lucidumoside A on the transcription factor AP-1 action was also investigated using molecular docking and dynamics simulations. The experiments suggested that inhibition of an AP-1-DNA complex formation could be on account of the direct interference of AP-1 binding onto the DNA binding sequence by ligustroside and lucidumoside A. The results suggest that both compounds have the highest potential for application as an anti-aging agent with the MMP inhibitory and anti-transcriptional activities.

Lignans and secoiridoid glycosides from the stem barks of Jasminum tortuosum

This paper reports on the first phytochemical analysis ever performed on Jasminum tortuosum Willd. This analysis, mainly carried out by means of column chromatography separation, NMR spectroscopy and mass spectrometry, led to the isolation and the identification of four compounds, namely the lignans ginkgool (1) and olivil-4′-O-β-glucopyranoside (2) and the secoiridoids oleoside dimethyl ester (3) and oleoside 11-methyl ester (4). The presence of these compounds is significant from a chemotaxonomic point of view, confirming the correct botanical classification of the species and, from a phytochemical standpoint, may suggest its possible use in the ethno-medicinal field.

Bioactivity‐guided Isolation of Antiosteoporotic Compounds from Ligustrum lucidum

The fruits of Ligustrum lucidum (FLL) has long been used for the treatment of osteoporosis in China, but the antiosteoporotic compounds in FLL are still poorly understood. In this study, the alkaline phosphatase (ALP) activity-guided isolation of osteogenic components from FLL was carried out by using osteoblast-like UMR-106 cells. Eight compounds, namely tyrosol (1), tyrosyl acetate (2), hydroxytyrosol (3), salidroside (4), oleoside dimethyl ester (5), oleoside-7-ethyl-11-methyl ester (6), nuzhenide (7), and G13 (8), were isolated and identified. Further study showed that compounds 3, 4, 7, and 8 increased ALP activity in UMR-106 cells. Compounds 5, 6, and 7 promoted the proliferation of UMR-106 cells. The aqueous extract of FLL-activated ERα/β-mediated gene transcription, whereas the isolated compounds were inactive. All eight isolated compounds also exhibited antioxidative activity, with compounds 1, 2, and 3 being the most potent. These results indicate that the antiosteoporotic effect of FLL is derived from different compounds together with different mechanisms such as ER-dependent or independent pathways and antioxidative effects. Salidroside (4) and nuzhenide (7) warrant further investigation as new pharmaceutical tools for the prevention and treatment of osteoporosis.

ChemInform Abstract: Structure Elucidation of Two Secoiridoid Glucosides from Jasminum officinale L. var. grandiflorum (L.) Kobuski.

Phytochemical investigation of the dried leaves of Jasminum officinale var. grandiflorum has led to the isolation of two new secoiridoid glucosides, (2R)-2-methoxyoleuropein and (2S)-2-methoxyoleuropein, together with four known secoiridoid glucosides, oleuropein, ligstroside, demethyloleuropein and oleoside dimethyl ester, a lignan, (-)-olivil and p-hydroxyphenethyl alcohol. The structures of the new compounds were elucidated from chemical and spectroscopic evidence.

Iridoids from Fraxinus excelsior with Adipocyte Differentiation-Inhibitory and PPARα Activation Activity

Two new secoiridoid glucosides, excelsides A (1) and B (2), were isolated from the seeds of Fraxinus excelsior. Their structures were elucidated as (2S,4S,3E)-methyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-[(6-O-beta-D-glucopyranosyl-beta-d-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate and (2S,4S,3E)-methyl 3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethyl]oxy-2-oxoethyl}-2-[(6-O-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate, respectively, on the basis of NMR and MS data. Eight known compounds were identified as nuzhenide (3), GI3 (4), GI5 (5), ligstroside (6), oleoside 11-methyl ester (7), oleoside dimethyl ester (8), 1'''-O-beta-D-glucosylformoside (9), and salidroside (10). Compounds 1-9 inhibited adipocyte differentiation in 3T3-L1 cells. Dilutions of the aqueous extract of F. excelsior (1:10,000) as well as compounds 2, 3, 4, 5, and 8 activated the peroxisome proliferator-mediated receptor-alpha (PPARalpha) reporter cell system in the range of 10(-4) M, compared to 10(-7)-10(-8) M for the synthetic PPARalpha activator, WY14,643. Both biological activity profiles support the hypothesis that inhibition of adipocyte differentiation and PPARalpha-mediated mechanisms might be relevant pathways for the antidiabetic activity of F. excelsior extract.

Active compounds from Fraxinus excelsior L. seeds: Anti-diabetic and body weight control effects

Fraxinus excelsior L. seed extract (FE) is recognized as an anti-diabetic agent [1]. Two new secoiridoid glucosides, excelside A (1) and excelside B (2) were isolated and elucidated from FE: (2S, 3E, 4S) 2H-Pyran-4-acetic acid-3-ethylidene-2-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) oxy]-3,4-dihydro-5-(methoxycarbonyl) methyl ester and (2S, 3E, 4S) 2H-Pyran-4-acetic acid-3-ethylidene-2-[(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) oxy]-3,4-dihydro-5-(methoxycarbonyl) 2-(4-hydroxyphenyl) ethyl ester, respectively. Eight known isolated compounds were identified as nuzhenide (3), GI3 (4), GI5 (5), ligstroside (6), oleoside-11-methyl ester (7), oleoside dimethyl ester (8), 1'''-O-β-D-glucosylformoside (9), and salidroside (10) [2]. Compounds 1-9 showed inhibitory activity against adipocyte differentiation in 3T3-L1 cells. FE (1:10,000) as well as 1, 3, 4, 5, and 8 were activating in PPARα-reporter cell system in the range of 10-4 M comparable to 10-8 M WY14,643. Therefore, PPARα-mediated mechanism is a possible relevant pathway for FE anti-diabetic activity. We also evaluated the effects of a low-fat diet (LFD), high-fat diet (HFD), and high fat diet + 0.5% FE (FED) on C57BL/6J mice during 16-weeks. FED decreased fasting blood glucose (33.2%, P<0.001), plasma insulin level (53.4%, P<0.05), and body weight gain (32.3%, P<0.05) compared to HFD. Finally, we used a screening model against glucose (50g) to assess the effect of FE on plasma glucose and insulin levels. FE (1.0g) was used in a double blind, randomized, crossover, placebo (wheat bran) controlled study on 16 healthy volunteers. FE reduced the glycemic AUC (P=0.02), but not the insulinemic AUC. These results encourage conducting long term clinical studies to further evaluate the efficacy and safety of FE.

Novel Secoiridoid Glucosides inOlea europaeaLeaves Suffering from Boron Deficiency

From the methanol extract of boron deficient Olea europaea leaves, two secoiridoid glycosides, not detected in leaf extracts of untreated plants, 6'-E-p-coumaroyl-secologanoside and 6'-O-[(2E)-2,6-dimethyl-8-hydroxy-2-octenoyloxy]-secologanoside, were isolated together with three known secoiridoid glycosides, oleuropein, oleoside dimethyl ester, and secologanoside. The structures of the isolated compounds were established by means of NMR and MS spectral analyses. The above novel secoiridoids were synthesized by the plant as a physiological response to nutrient stress.

Storage Behavior of Chionanthus retusus Seed and Asynchronous Development of the Radicle and Shoot Apex during Germination in Relation to Germination Inhibitors, Including Abscisic Acid and Four Phenolic Glucosides

Studies on seed storage of Chionanthus retusus Lindl. & Paxt. revealed an orthodox behavior, one which showed both desiccation and freezing tolerance. An epicotyl after-ripening dormancy was expressed in C. retusus seeds by slow growth of the shoot apex relative to more rapid growth of the radicle when seeds were germinated at 30/20 degrees C. Although these seeds exhibit radicle protrusion, they must be after-ripened for another 8-10 weeks at 30/20 degrees C in order to obtain normal shoot growth. Removal of the endosperm, however, quickly stimulated cotyledon and shoot emergence without the additional after-ripening. Water-soluble glucoside phenolics, GL-3, Nuzhenide, ligustroside and oleoside dimethyl ester are present at relatively high levels in endosperm of freshly harvested seeds. These glucoside phenolics are excreted from the endosperm during subsequent after-ripening. Embryo and endosperm tissue from seed germinating at 30/20 degrees C (germination being defined by protrusion of the radicle) had a 10 times lower abscisic acid (ABA) content than similar tissues from freshly harvested mature seed. However, no shoot growth occurred even with the 10-fold reduction in ABA and a concomitant increase in endogenous gibberellins A1, A4 and A20. Thus, epicotyl dormancy during the first 8 weeks of after-ripening at 30/20 degrees C may be controlled by factors other than high ABA, i.e., the slow development of the shoot apex following radicle protrusion may be controlled more by high levels of glucoside phenolics than by diminished ABA and elevated GA levels.

Analysis by liquid chromatography‐tandem mass spectrometry of biophenolic compounds in olives and vegetation waters, Part I

AbstractBiophenolic compounds constitute a complex mixture in olives and derived products. In this work, ion‐spray tandem mass spectrometry coupled with liquid chromatography is applied to the identification and quantification of biophenols present in complex matrices such as olives and vegetation waters. The extraction and purification method for the biophenol present in both the matrices is reported. Using this approach the main biophenols found, in three different variety of olives, were: tyrosol, hydroxytyrosol, oleoside methyl ester, oleoside dimethyl ester, and oleuropein. In vegetation water the biophenols are present in lower amounts than in olives.

Secoiridoid constituents from the fruits of Ligustrum lucidum

Two secoiridoid glucosides, lucidumosides A and B, as well as six known glucosides, oleoside dimethyl ester, ligustroside, oleuropein, nuezhenide, isonuezhenide, and neonuezhenide, were isolated from the fruits of Ligustrum lucidum. Their structures were elucidated by spectroscopic methods.

Antioxidative glucosides from the fruits of Ligustrum lucidum.

The ethanol extract of the fruits of Ligustrum lucidum was shown to have inhibitory effects on the hemolysis of red blood cells induced by 2,2'-azo-bis-(2-amidinopropane) dihydrochloride. Bioassay-guided analysis led to the isolation of ten secoiridoid glucosides. Two of them were new, lucidumosides C and D. Their structures were elucidated by spectroscopic methods. The other eight compounds were identified as oleoside dimethyl ester, ligustroside, oleuropein, nuezhenide, isonuezhenide, neonuezhenide, lucidumoside A and lucidumoside B. Five compounds, oleoside dimethyl ester, oleuropein, neonuezhenide, lucidumoside B and lucidumoside C, exhibited strong antioxidant effect against hemolysis of red blood cells induced by free radicals.

In vitro evaluation of secoiridoid glucosides from the fruits of Ligustrum lucidum as antiviral agents.

Six secoiridoid glucosides, lucidumoside C (1), oleoside dimethylester (2), neonuezhenide (3), oleuropein (4), ligustroside (5) and lucidumoside A (6), isolated from the fruits of Ligustrum lucidum (Oleaceae), were examined in vitro for their activities against four strains of pathogenic viruses, namely herpes simplex type I virus (HSV-1), influenza type A virus (Flu A), respiratory syncytial virus (RSV) and parainfluenza type 3 virus (Para 3). Antiviral activities were evaluated by the cytopathic effect (CPE) inhibitory assay. The purpose was to check if the antioxidative potency of these glucosides correlated with their antiviral potency. Results showed that none of the glucosides had any significant activity against HSV-1 and Flu A. Oleuropein, however, showed significant antiviral activities against RSV and Para 3 with IC50 value of 23.4 and 11.7 microg/ml, respectively. Lucidumoside C, oleoside dimethylester and ligustroside showed potent or moderate antiviral activities against Para 3 with IC50 values of 15.6-20.8 microg/ml. These results also documented that the anti-oxidative potency of these secoiriodoid glucosides was not directly related to their antiviral effects.

Secoiridoid Glucosides and Iridoids From Jasminum Odoratissimum

Two new secoiridoid glucosides, trans- 10-(cinnamoyloxy) oleoside dimethylester (methyl jasminoside) and cis-10-(cinnamoyloxy) oleoside monomethyl ester, and two new iridoids, 1α-and 1β-, 7-dehydrologanetin, together with the known iridoid jasminoside were isolated from leaves of Jasminum odoratissimum. the structures of these compounds have been characterised on the basis of spectroscopic evidence.

Structure Elucidation of Two Secoiridoid Glucosides from Jasminum officinale L. var. grandiflorum (L.) KOBUSKI.

Phytochemical investigation of the dried leaves of Jasminum officinale var. grandiflorum has led to the isolation of two new secoiridoid glucosides, (2R)-2-methoxyoleuropein and (2S)-2-methoxyoleuropein, together with four known secoiridoid glucosides, oleuropein, ligstroside, demethyloleuropein and oleoside dimethyl ester, a lignan, (-)-olivil and p-hydroxyphenethyl alcohol. The structures of the new compounds were elucidated from chemical and spectroscopic evidence.

Secoiridoids from Jasminum odoratissimum

Five new secoiridoids, trans- and cis-6‘-O-p-coumaroyl-8-epikingiside (1a) and (1b), trans- and cis-10-(p-coumaroyloxy)oleoside dimethyl ester (2a) and (2b), and 6‘-O-acetyl-10-acetoxyoleoside (2e), were isolated from J. odoratissimum and their structures determined by spectroscopic means. Compounds 1a and 1b and 2a and 2b were characterized as their peracetylated derivatives (1c and 1d and 2c and 2d, respectively).

Jaspolyside, a secoiridoid glycoside from Jasminum polyanthum

A new secoiridoid glucoside, jaspolyside was isolated from the leaves of Jasminum polyanthum along with nine known secoiridoid glycosides: oleoside dimethyl ester, 10-hydroxyoleoside dimethyl ester, oleoside 11-methyl ester, methyl-glucooleoside, 8-epi-kingiside, ligustroside, angustifolioside B, oleuropein, and oleoacetoside. The structure of the new compound has been established on the basis of spectral and chemical methods.

Secoiridoid Glycosides from Jasminum Polyanthum

AbstractChemical investigation of the ethanolic extract of Jasminum polyanthum Franch has resulted in the isolation of verbascoside (10) and 9 secoiridoid glycosides including oleoside dimethyl ester (1), 10‐hydroxy oleoside dimethyl ester (2), oleoside 11 methyl ester (3), methyl‐glucooleoside (4), 8‐epikingiside (5), ligustroside (6), angustifolioside B (7), oleuropein (8), and oleoacetoside (9). The structures of 1‐10 were established primarily on the basis of NMR analysis.

A secoiridoid glycoside from Osmanthus asiaticus

A new secoiridoid glycoside, secologanoside 7-methyl ester, was isolated together with 10 known secoiridoid glycosides, 8-epikingiside, oleuropein, 10-hydroxyoleuropein, 10-acetoxyoleuropein, ligstroside, 10- hydroxyligstroside, 10-acetoxyligstroside, oleoside dimethyl ester, 10-hydroxyoleoside dimethyl ester, 10-hydroxyoleoside 11-methyl ester, from the bark of Osmanthus asiaticus. The structure of the new compound has been characterized on the basis of spectroscopic evidence.