The quantitative isolation and antimicrobial activity of the aglycone of aucubin

doi:10.1016/S0031-9422(00)81711-2

Phytochemistry

Volume 25, Issue 10, 1986, Pages 2420-2422

https://doi.org/10.1016/S0031-9422(00)81711-2 Get rights and content

Abstract

Despite the reported instability of iridoid aglycones, a new procedure was developed for the quantitative extraction of aucubigenin from an enzymatic hydrolysate of aucubin. The aglycone was obtained in crystalline form and was for the first time spectroscopically characterized (¹H and ¹³C NMR spectra). Its antimicrobial activity against yeasts, bacteria and moulds was also accurately tested.

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Cited by (70)

Determination of aucubin by supramolecular solvent-based dispersive liquid-liquid microextraction and UPLC-MS/MS: Application to a pharmacokinetic study in rats with type 1 diabetes
2020, Journal of Pharmaceutical and Biomedical Analysis
Citation Excerpt :
Aucubin is an iridoid glycoside found in traditional Chinese medicines, such as Eucommia ulmoides [8,9] or Plantago lanceolata [10]. Aucubin has been proven to have many beneficial health effects, such as anticancer activity [11,12], hepatoprotective effects [13], neuroprotective effects [14], and antimicrobial activity [15]. Interestingly, aucubin was found to lower blood glucose levels in diabetic rats [16].
A novel method was developed for the determination of aucubin in rat serum by ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) with supramolecular solvent (SUPRAS)-based dispersive liquid-liquid microextraction (DLLME). The SUPRAS was prepared with pentanol as extraction solvent and tetrahydrofuran as dispersing agent. Based on single factor test and response surface methodology, critical parameters were optimized as: 1 mL of pentanol as extraction solvent, 4 mL of tetrahydrofuran as dispersing agent, 200 μL of SUPRAS, and vortex duration of 2.5 min. The established method was validated in terms of selectivity, linearity, accuracy, precision, recovery, stability, and applied to a pharmacokinetic study on type 1 diabetes model rats intraperitoneally administered with aucubin. The experimental results showed that the maximum concentration in serum (C_max) and area under the serum concentration versus time curve (AUC) of aucubin in type 1 diabetic rats were higher than those in normal rats. Such pharmacokinetic alterations might presumably result from the pathological state of type 1 diabetes. The current study may provide scientific evidence and inspiring insights for clinical application of aucubin for the treatment of diabetes.
A review of the pharmacology and toxicology of aucubin
2020, Fitoterapia
Citation Excerpt :
The glycosidic bond of AU is cleaved under acidic conditions to produce aglycones, glucose and other products. The hemiacetal structure in the aglycon is spontaneously opened in aqueous solution to form a dialdehyde structure [109]. The aglycon can also undergo intramolecular rearrangement and be converted into a stable isomer (1,10-anhydro-6-deoxy-7,8-dihydro- 7,8-dihydroxyaucubigenin) [110], the possible degradation process of AU is shown in Fig. 2.
Aucubin is an iridoid glycoside that is widely prevalent in traditional medicinal herbs, such as Eucommia ulmoides Oliv., Aucuba japonica Thunb. and Plantago asiatica L. This review aims to provide a comprehensive summary of the source, biological activity, pharmacokinetics and toxicology of aucubin with the ultimate objective of providing a guide for future drug development and potential clinical applications of aucubin. Aucubin is a highly active compound possessing extensive biological effects including antioxidant, anti-aging, anti-inflammatory, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective properties. Although aucubin has been shown to have poor oral bioavailability in rats, aucubin is widely distributed in multiple organs including kidney, liver, heart, spleen and lung, and there is a sex difference in the absorption of aucubin. Tolerance of aucubin is good and no serious adverse reactions have been observed to date. In short, aucubin is a compound with abundant potential sources, good safety and numerous beneficial biological activities, which exhibits high potential value for use in health care products and pharmaceuticals. In order to accelerate the development and utilization of aucubin-related products, in-depth studies should be focused on the following questions of interest. First, it is necessary to introduce advanced separation and formulation technologies to improve the yield and stability of aucubin products. Second, studies should focus on the specific pharmacological activities of aucubin to determine the structure-activity relationship so as to improve the efficacy and reduce side effects. Finally, clinical studies are needed to confirm the efficacy of aucubin in specific diseases.
The efficacy of Plantago lanceolata for mitigating nitrous oxide emissions from cattle urine patches
2019, Science of the Total Environment
Urine deposited by grazing animals is the main source of nitrous oxide (N₂O) emissions in New Zealand. Recent studies have suggested that certain pasture plants, for example plantain (Plantago lanceolata), can curb N₂O emissions from livestock systems. This study aimed to i) evaluate the potential of plantain for reducing N₂O emissions from cattle urine patches; ii) determine the effect of including plantain in animal diets on urine-N loading and its influence on N₂O emissions; and, iii) evaluate whether any effects on N₂O emissions reduction could be attributed to a ‘urine’ or a ‘plant’ effect. A static chamber method was used to measure N₂O fluxes from urine collected from cows fed a 0, 15, 30 or 45% plantain mixed with “standard” ryegrass/clover (Lolium perenne/Trifolium repens) diet and applied to plots with the corresponding percentage of plantain in the sward. In addition, we measured N₂O emissions from different proportions of plantain in the sward (0, 30, 60 and 100%) that received urine collected from cows fed on ryegrass/clover. The urine N loading rates of animals fed plantain, significantly reduced with increasing proportions of plantain in the diet (r² = 0.987, P < 0.01). There was a trend of lower N₂O emissions with an increasing proportion of plantain in the diet (r² = 0.830, P < 0.08). However, there was no significantly difference in the N₂O emission factors (P > 0.10). Following applications of standard urine, total N₂O emissions and emission factor reduced linearly as the proportion of plantain in the sward increased (r² = 0.969, P < 0.05 and 0.974, P < 0.05, respectively). The results suggest that the efficacy of plantain as a N₂O mitigation option is due to both a reduction in urinary N excretion and a plant effect. The latter could be due to biological nitrification inhibition (BNI) caused by the release of root exudates and/or changes in the soil microclimate.
Anti-HIV Agents From Nature: Natural Compounds From Hypericum hircinum and Carbocyclic Nucleosides From Iridoids
2018, Studies in Natural Products Chemistry
Citation Excerpt :
Capillary electrophoresis is a fast technique in comparison with other techniques used to isolate a mixture of nine or less iridoids. Despite this interesting method of resolution of mixtures of iridoids and the pharmaceutical interest addressed to iridoids, there are few scientific papers which face this kind of purification way [97–158]. In the last 30 years, occasionally, iridoids were employed as starting synthons for the partial synthesis of new carbocyclic nucleoside analogues.
The presence of antiviral compounds in the Guttiferae family as medicinal plants and the long traditional use of species of the genus Hypericum for the treatment of many viral infections have developed a strong interest. Among the natural products of plant origin, the ones from Hypericum genus were cited as promising anti-HIV agents. This chapter will report an updated review of carbocyclic nucleoside analogues as anti-HIV agents from iridoids. Moreover, the partial synthesis of antiviral agents from iridoid glucosides to carbocyclic nucleosides as new anti-HIV agents is reviewed.
Bioactive compounds, aucubin and acteoside, in plantain (Plantago lanceolata L.) and their effect on in vitro rumen fermentation
2016, Animal Feed Science and Technology
Plantain (Plantago lanceolata L.) contains bioactive compounds with antimicrobial activity that can potentially influence ruminal fermentation. This study aimed to identify the concentration of the bioactive compounds catalpol, aucubin, and acteoside in plantain cv. ‘Ceres Tonic’ through two consecutive growing seasons (2011–2012 and 2012–2013). Then the herbage with highest levels of bioactive compounds was used to evaluate their effect on rumen in vitro fermentation. Plantain cv. ‘Ceres Tonic’ had almost nil concentration of catalpol. Both aucubin and acteoside concentrations increased (P < 0.05) through the growing season. Aucubin increased from 1.78 to 3.80 mg/g DM in the first and from 0.44 to 6.87 mg/g DM in the second growing season; while, acteoside increased from 23.6 to 35.4 mg/g DM and from 0.5 to 41.7 mg/g DM, respectively. The in vitro experiment evaluated the effect of aucubin and acteoside on ammonia (NH₃), volatile fatty acids (VFA) and gas production (GP) parameters. Aucubin and acteoside were added to chicory (Cichorium intybus L.) as negative and to plantain as positive controls. The treatments were (i) chicory (CH); (ii) chicory + 10 mg aucubin/g DM (C+au); (iii) chicory + 20 mg aucubin/g DM (C+2au); (iv) chicory + 40 mg acteoside/g DM (C+ac); (v) plantain naturally containing 7 mg/g DM of aucubin and 36 mg/g DM of acteoside (PL); (vi) plantain + extra 10 mg aucubin/g DM (P+au); and (vii) plantain + extra 36 mg acteoside/g DM (P+ac). Plantain with natural concentrations of bioactives produced 40% less NH₃ than chicory over 24 h. The exogenous addition of both bioactive compounds reduced net NH₃ production by CH and PL. The increase in potential GP from acteoside fermentation suggested its use as an energy source. Whereas, the addition of aucubin reduced the rate of GP at dose level, potentially due to its bactericide activity. Therefore, acteoside would have a greater positive effect than aucubin on ruminant animals.
Aucubin, a naturally occurring iridoid glycoside inhibits TNF-α-induced inflammatory responses through suppression of NF-κB activation in 3T3-L1 adipocytes
2013, Cytokine
Obesity is closely associated with a state of chronic, low-grade inflammation characterized by abnormal cytokine production and activation of inflammatory signaling pathways in adipose tissue. Tumor necrosis factor (TNF)-α is chronically elevated in adipose tissues of obese rodents and humans. Increased levels of TNF-α are implicated in the induction of atherogenic adipokines, such as plasminogen activator inhibitor (PAI)-1, adipose-tissue-derived monocyte chemoattractant protein (MCP)-1, and interleukin (IL)-6. Aucubin, an iridoid glycoside existing in medicinal plants, has been reported to show an anti-inflammatory activity by suppression of TNF-α production in murine macrophages. The present study is aimed to investigate the effects of aucubin on TNF-α-induced atherogenic changes of the adipokines in differentiated 3T3-L1 cells. Aucubin significantly inhibited TNF-α-induced secretion and mRNA synthesis of the atherogenic adipokines including PAI-1, MCP-1, and IL-6. Further investigation of the molecular mechanism revealed that pretreatment with aucubin suppressed extracellular signal-regulated kinase (ERK) activation, inhibitory kappa Bα (IκBα) degradation, and subsequent nuclear factor kappa B (NF-κB) activation. These findings suggest that aucubin may improve obesity-induced atherosclerosis by attenuating TNF-α-induced inflammatory responses.

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The quantitative isolation and antimicrobial activity of the aglycone of aucubin

Abstract

Tetrahedron Lett.

Tetrahedron Lett.

Phytochemistry

Tetrahedron

Tetrahedron

Phytochemistry

Phytochemistry

Tetrahedron Lett.

J. Org. Chem.

Heterocycles