Novel Conjugates of 1,3-Diacylglycerol and Lipoic Acid: Synthesis, DPPH Assay, and RP-LC-MS-APCI Analysis

Madawala, Samanthi R. P.; Andersson, Ronnie; Jastrebova, Jelena; Almeida, Sidalina; Dutta, Paresh C.

doi:10.1155/2011/419809

Cited by 18 publications

(18 citation statements)

References 34 publications

(54 reference statements)

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“…• in this study is in agreement as it was observed in LA derivatives of 1,3-diolein [Madawala et al, 2011]. In a previous study, LA and several coumarin derivatives of LA dissolved in ethanol at 0.5 mmol/L concentration of the fi nal mixture measured after 20 and 60 min have also • dependent on concentration.…”

Section: Discussionsupporting

confidence: 90%

“…Mass spectra recorded in negative mode for all individual PSLA derivatives, showed the dominant fragment ion at m/z 205, derived from the LA moiety dissociated at the esterifi ed position. A fragment ion at m/z 171 correspond to a loss at m/z 34, due to the elimination of H 2 S from m/z 205 fragment concur with the previously published report [Schupke et al, 2001;Madawala et al, 2011].…”

Section: H]supporting

confidence: 92%

“…According to the results from the DPPH test, PSDHLA showed very high free radical scavenging capacity ( Figure 4b) compared with PSLA (Figure 4a). Similar interaction and kinetic behaviour was observed for pure DHLA and 1, 3-diolein derivative of DHLA by the DPPH test [Madawala et al, 2011]. In that study LA was also included in the test and showed very low free radical scavenging activity compared with DHLA.…”

Section: Discussionsupporting

confidence: 75%

“…This fragment ion can be due to dehydrogenation of DHLA moiety while cleaving from the PSDHLA. Similar dehydrogenated fragment ion at m/z 205 was observed for pure DHLA and 1,3diolein dihydrolipoate in a previous study [Madawala et al, 2011]. We have suggested that this might be due to high vaporizer and drying gas temperatures used during the ionisation in APCI mode.…”

Section: H]supporting

confidence: 83%

“…Data of RP-HPLC-APCI-MS for LA and DHLA have been published recently [Madawala et al, 2011]. The chromatographic conditions were different in the present study but the mass spectra of these compounds were similar (MS data are not shown).…”

Section: Continued On the Next Pagementioning

confidence: 55%

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Phytosterol and α-Lipoic Acid Conjugates: Synthesis, Free Radical Scavenging Capacity and RP-LC-MS-APCI Analysis

Madawala¹,

Andersson²,

Jastrebova³

et al. 2012

Pol. J. Food Nutr. Sci.

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Plant sterols (PS) are bioactive compounds effective in reducing plasma cholesterol. Fatty acid esters of PS have improved solubility and blending properties when utilized in various food products. Naturally occurring α-lipoic acid (LA) and its reduced form dihydrolipoic acid (DHLA) are known for their antioxidant activity. In addition, they have shown an array of health benefi cial properties against obesity, diabetes, cancer, cardiovascular and infl ammatory diseases etc. Different LA conjugates have been reported to have increased bioactivity compared to the parent compounds. The objective of this study was to synthesize PS esters of LA (PSLA) and DHLA (PSDHLA) in order to increase their cholesterol lowering effect and reducing the risk of atherosclerosis with additional health benefi ts e.g. against oxidative stress.Synthesis of PSLA and PSDHLA was performed with a pure PS mixture of β-sitosterol, stigmasterol, campesterol and brassicasterol. The free radical scavenging capacity of the conjugates was assessed by the DPPH method. Remaining percentage of DPPH free radicals was measured at the steady state for different concentrations of PSLA and PSDHLA. High free radical scavenging capacity was observed for PSDHLA compared with PSLA. Effi cient concentration EC 50 as a molar ratio for PSDHLA was 0.43. The derivatives were analyzed by RP-HPLC-MS-APCI. The order of the elution times of the compounds observed in HPLC-MS analysis was PS< PSDHLA< PSLA. Baseline separation was not achieved between campesterol and stigmasterol and their derivatives. These compounds could be identifi ed by their characteristic fragment ions from the mass spectral data.

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Section: Discussionsupporting

confidence: 90%

Section: H]supporting

confidence: 92%

Section: Discussionsupporting

confidence: 75%

Section: H]supporting

confidence: 83%

Section: Continued On the Next Pagementioning

confidence: 55%

See 3 more Smart Citations

Phytosterol and α-Lipoic Acid Conjugates: Synthesis, Free Radical Scavenging Capacity and RP-LC-MS-APCI Analysis

Madawala¹,

Andersson²,

Jastrebova³

et al. 2012

Pol. J. Food Nutr. Sci.

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Aza‐CGP37157‐lipoic hybrids designed as novel Nrf2‐inducers and antioxidants exert neuroprotection against oxidative stress and show neuroinflammation inhibitory properties

Michalska

Tenti

Satriani

et al. 2019

Drug Development Research

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Two multitarget hybrids, derived from an aza-analogue of CGP37157, a mitochondrial Na + /Ca 2+ exchanger antagonist, and lipoic acid were designed in order to combine in a single molecule the antioxidant and Nrf2 induction properties of lipoic acid and the neuroprotective activity of CGP37157. The hybrid derivatives showed Nrf2 induction and radical scavenging properties, leading to a good neuroprotective profile against oxidative stress, together with an interesting antineuroinflammatory activity.The results obtained show differences in activity depending on the configuration of the chiral center of LA. K E Y W O R D Santi-inflammatory activity, neuroprotection, Nrf2 induction, radical scavenging

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Enzymatic synthesis and characterization of 1‐lipoyl‐2‐palmitoyl phosphatidylcholine: A novel phospholipid containing lipoic acid

Kaki

Balakrishna

2014

Euro J Lipid Sci & Tech

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Bioorganic synthesis of a novel phospholipid, 1-lipoyl-2-palmitoyl phosphatidylcholine (LPPC) was carried out using dipalmitoylphosphotidylcholine (DPPC) and lipoic acid as substrates via lipase catalyzed transesterification reaction at controlled water activity. A high lipoic acid concentration and low water activity were necessary for the enzymatic acidolysis reaction in an organic solvent medium at ambient temperature. Four immobilized lipases were examined for the incorporation of lipoic acid into DPPC. The transesterification reaction resulted in formation of the desired product along with the lyso PC as a by-product at controlled water activity of 0.11 in 96 h using Lipozyme RM IM lipase. The composition of the modified PC showed that 41.07 mol% of lipoic acid was incorporated into DPPC. The transesterification was regioselective with nearly 91% incorporation of lipoic acid in the sn-1 position with about 4% incorporation in the sn-2 position in the product PC. The prepared LPPC can have applications as a lipid based prodrug of lipoic acid and also can have potential applications in drug solubilization and release studies.Practical applications: Novel phospholipid bearing lipoic acid as an active ingredient is synthesized via enzymatic route. It is a smart combination of two biologically active molecules with proven activities. The prepared phospholipid can have potential applications in nutraceuticals, cosmetics, and biomedical fields. This molecule can help to address the bioavailability issues of lipoic acid. The product can have applications in controlled release of lipoic acid due to incorporation into a phospholipid.

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Novel Conjugates of 1,3-Diacylglycerol and Lipoic Acid: Synthesis, DPPH Assay, and RP-LC-MS-APCI Analysis

Cited by 18 publications

References 34 publications

Phytosterol and α-Lipoic Acid Conjugates: Synthesis, Free Radical Scavenging Capacity and RP-LC-MS-APCI Analysis

Phytosterol and α-Lipoic Acid Conjugates: Synthesis, Free Radical Scavenging Capacity and RP-LC-MS-APCI Analysis

Aza‐CGP37157‐lipoic hybrids designed as novel Nrf2‐inducers and antioxidants exert neuroprotection against oxidative stress and show neuroinflammation inhibitory properties

Enzymatic synthesis and characterization of 1‐lipoyl‐2‐palmitoyl phosphatidylcholine: A novel phospholipid containing lipoic acid

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