Self-assembling and antioxidant activity of some vitamin C derivatives

Nostro, Pierandrea Lo; Capuzzi, Giulia; Pinelli, Patrizia; Mulinacci, Nádia; Romani, Annalisa; Vincieri, Franco Francesco

doi:10.1016/s0927-7757(99)00465-3

Cited by 53 publications

(48 citation statements)

References 16 publications

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“…In this context, Lo Nostro et al [32,33] reported that the addition of an acyl chain to the L-ascorbic acid in the 6-position, retained or even enhanced its physiological and antioxidant activity measured by DPPH (a,a-diphenyl-bpicrylhydrazyl) method. Song et al [33] demonstrated that 6-O-ascorbyl oleate had a better protective effect on human umbilical cord vein endothelial cells than other ascorbyl derivatives.…”

Section: Antioxidant Activitymentioning

confidence: 99%

Synthesis and Properties of Ascorbyl Esters Catalyzed by Lipozyme TL IM using Triglycerides as Acyl Donors

Reyes‐Duarte

López-Cortés

Torres

et al. 2010

J Americ Oil Chem Soc

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Esters of L-ascorbic acid with long-chain fatty acids (E-304) are employed as antioxidants in foods rich in lipids. Although their enzymatic synthesis offers some advantages compared with the current chemical processes, most of the reported methods employ the immobilized lipase from Candida antarctica as biocatalyst and free fatty acids or activated esters as acyl donors. In order to diminish the cost of the process, we have investigated the synthesis of ascorbyl oleate and ascorbyl palmitate esters with the immobilized Thermomyces lanuginosus lipase Lipozyme TL IM-which is significantly less expensive than Novozym 435-and triglycerides as source of fatty acids. Lipozyme TL IM gave rise to a lower yield of 6-O-ascorbyl oleate than Novozym 435 when using triolein (64 vs. 84%) and olive oil (27 vs. 33%) as acyl donors. Both 6-O-ascorbyl oleate and 6-O-ascorbyl palmitate displayed excellent surfactant and antioxidant properties. The Trolox Equivalent Antioxidant Capability values for the oleate and palmitate were 71 and 84%, respectively, of those obtained with L-ascorbic acid; however, both derivatives were able to stabilize soybean oil towards peroxide formation.

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Section: Antioxidant Activitymentioning

confidence: 99%

Synthesis and Properties of Ascorbyl Esters Catalyzed by Lipozyme TL IM using Triglycerides as Acyl Donors

Reyes‐Duarte

López-Cortés

Torres

et al. 2010

J Americ Oil Chem Soc

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“…It has been shown that ASC n conserve part of the radical scavenging activity in aggregates such as micelles. For example, ASC 10 micelles retain about half of the antioxidant performance for oxygen uptake [1], whilst ASC 12 and ASC 14 only retain $40 and $34% of the antioxidant activity [7,9] compared to unmodified L-ascorbic acid. It is well known that L-ascorbic acid is stable in solid form, but it is susceptible to oxidation when in solution.…”

Section: Introductionmentioning

confidence: 99%

Alkyl esters of l-ascorbic acid: Stability, surface behaviour and interaction with phospholipid monolayers

Mottola

Vico

Villanueva

et al. 2015

Journal of Colloid and Interface Science

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“…This result suggests that the ASC-containing compound should be integrated into the lipid membrane in order to be effectively able to reduce membrane components. Since the reduction power of the ASCn studied are similar [9,26] the differences in fluorescence intensity decay may be a direct measurement of the ability for membrane incorporation of the compounds. Then, ASC12…”

Section: Direct Observation Of Ascn-membrane Interactionmentioning

confidence: 99%

The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

Giudice

Ambroggio

Mottola

et al. 2016

Biochimica et Biophysica Acta (BBA) - Biomembranes

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l-ascorbic acid alkyl esters (ASCn) are lipophilic forms of vitamin C, which maintain some of its antioxidant power. Those properties make this drug family attractive to be used in pharmacological preparations protecting other redox-sensible drugs or designed to reduce possible toxic oxidative processes. In this work, we tested the ability of l-ascorbic acid alkyl esters (ASCn) to modulate the structure, permeability, and rheological properties of phospholipid bilayers. The ASCn studied here (ASC16, ASC14, and ASC12) alter the structural integrity as well as the rheological properties of phospholipid membranes without showing any evident detergent activity. ASC14 appeared as the most efficient drug in destabilize the membrane structure of nano- and micro-size phospholipid liposomes inducing vesicle content leakage and shape elongation on giant unilamellar vesicles. It also was the most potent enhancer of membrane microviscosity and surface water structuring. Only ASC16 induced the formation of drug-enriched condensed domains after its incorporation into the lipid bilayer, while ASC12 appeared as the less membrane-disturbing compound, likely because of its poor, and more superficial, partition into the membrane. We also found that incorporation of ASCn into the lipid bilayers enhanced the reduction of membrane components, compared with soluble vitamin C. Our study shows that ASCn compounds, which vary in the length of the acyl chain, show different effects on phospholipid vesicles used as biomembrane models. Those variances may account for subtly differences in the effectiveness on their pharmacological applications.

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Self-assembling and antioxidant activity of some vitamin C derivatives

Cited by 53 publications

References 16 publications

Synthesis and Properties of Ascorbyl Esters Catalyzed by Lipozyme TL IM using Triglycerides as Acyl Donors

Synthesis and Properties of Ascorbyl Esters Catalyzed by Lipozyme TL IM using Triglycerides as Acyl Donors

Alkyl esters of l-ascorbic acid: Stability, surface behaviour and interaction with phospholipid monolayers

The amphiphilic alkyl ester derivatives of l -ascorbic acid induce reorganization of phospholipid vesicles

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