Antioxidant activity of the mangiferin inclusion complex with β-cyclodextrin
Open accessAbstract
The aim of this study was to characterize the complex between mangiferin (MGN) with β-cyclodextrin (β-CD) obtained through the co-evaporation method using Differential Scanning Calorimetry (DSC) and Fourier Transform Infrared spectroscopy (FT-IR), as well as to verify the antioxidant activity of this complex by means of radical scavenging activity toward 2,2′-diphenyl-1-picrylhydrazyl radical (RSA-DPPH), with additional analysis of solvent effects, and Oxygen Radical Antioxidant Capacity-Fluorescein (ORAC-FL) assays. The protective effects of MGN and the MGN:β-CD complex against peroxyl radical-initiated membrane lipid peroxidation were also evaluated. The analysis of the solvent effects in the DPPH method demonstrated that at amounts of organic solvents lower than the ratio 50:50 (methanol–water or ethanol–water) there is a drawback, due to the hydrophobic nature of DPPH and should not be used. The antioxidant activity of the MGN:β-CD complex was higher than in its free form, as seen by both methods. The RSA-DPPH value was twofold larger for the complex while the ORAC-FL value was fifteenfold larger. Lipid peroxidation assays showed that the MGN:β-CD complex has a protective effect on the membrane that is as effective as the positive control (Trolox).
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Written from the paper’s full text.
TL;DR
Mangiferin (MGN) was complexed with β-cyclodextrin (β-CD) by co-evaporation and characterized by FT-IR and DSC. The MGN:β-CD complex showed higher antioxidant activity than free MGN in DPPH and ORAC-FL assays, and protected membrane lipids against peroxyl radical-initiated peroxidation as effectively as Trolox.
Key findings
- FT-IR and DSC indicated inclusion complex formation: MGN’s fusion endothermic peak almost disappeared in the complex, with a small peak detected at 259.5 °C; β-CD fusion temperature was reduced from 335.0 °C to 271.4 °C in the physical mixture.
- RSA-DPPH was higher for the complex than free MGN at 50 and 100 μmol L⁻¹: at 50 μmol L⁻¹, complex ≈65% vs free ≈28%; at 100 μmol L⁻¹, complex increased to 78%. At 500 μmol L⁻¹, free MGN gave RSA-DPPH similar to gallic acid at 100 μmol L⁻¹. β-CD alone showed no significant DPPH activity.
- ORAC-FL values: MGN alone had an ORAC value of 2.3 (2.3 times Trolox), while the MGN:β-CD complex showed an ORAC value fifteenfold larger.
- Lipid peroxidation assays showed MGN and MGN:β-CD complex had protective effects on the membrane as well as Trolox; inclusion in β-CD favored membrane protection.
Methods
- MGN:β-CD complex (1:1) was prepared by co-evaporation in 5 mL ethanol/100 mL water, shaken at 170 rpm at 25 °C for 24 h, protected from light, filtered, and evaporated under reduced pressure.
- Physicochemical characterization used FT-IR (4000–500 cm⁻¹, KBr pellets) and DSC (25–400 °C, 5 °C min⁻¹, dynamic nitrogen).
- Antioxidant activity was measured by RSA-DPPH (516 nm, every 5 min for 50 min, triplicate; solvent effects with methanol:water and ethanol:water), ORAC-FL (fluorescein/AAPH, Trolox calibration, 96-well microplate), and a membrane biomimetic lipid peroxidation assay using soy phosphatidylcholine unilamellar vesicles with C11-BODIPY 581/591 and AAPH.
Limitations
- The paper states no explicit limitations section. It notes that DPPH cannot be used at organic solvent ratios lower than 50:50 (methanol:water or ethanol:water) because DPPH precipitates due to its hydrophobic nature.
- The paper also states that ORAC does not show the capacity to inhibit oxidation and lipid peroxidation, which is why lipid peroxidation assays were added.
- Evident from the text: all antioxidant and membrane-protection results are in vitro; no in vivo bioavailability, release, or food/pharmaceutical application data are reported.
Model-written summary. Check it against the paper before relying on it.
Integrity signals
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Cites
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Claims the paper makes
1 of 18 cited sources checked · 1 supported · 0 flagged
- Findingown data
FT-IR confirmed interaction between MGN and b-CD.
“The interaction between MGN and b-CD was confirmed by FT-IR spectroscopy.”
Quote in the paperSubstantial claim - Findingown data
The effect of b-CD on RSA-DPPH was more pronounced at low concentration of MGN.
“It is noticeable that the effect of b-CD on RSA-DPPH was more pronounced at a low concentration of MGN.”
Quote in the paperNot a substantial claim - Findingcitation
It is not possible to use a percentage of solvent lower than 50% because DPPH precipitates due to insolubility in water.
“It is not possible to use a percentage of solvent lower than 50%, because DPPH precipitates in the medium, due to its insolubility in water, as already described by Li, Zhang, Chao, and Shuang (2009).”
Quote in the paperSubstantial claim0 of 1 sources checked- cites Li et al., 2009
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Findingcitation
b-CD alone has no significant antioxidant activity toward DPPH.
“The same assay was performed with b-CD alone and no significant antioxidant activity toward DPPH was observed, as described by Lu et al. (2009).”
Quote in the paperSubstantial claim0 of 1 sources checked- cites Lu et al., 2009
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Findingown data
DSC confirmed MGN was included into b-CD cavity.
“which displacements confirmed that MGN was included into b-CD cavity.”
Quote in the paperSubstantial claim
- Findingown data
MGN:b-CD complex shows an ORAC value fifteenfold larger than free MGN.
“while the MGN:b-CD complex shows an ORAC value fifteenfold larger.”
Quote in the paperSubstantial claim - Findingown data
MGN:b-CD complex showed higher antioxidant activity than free MGN by RSA-DPPH at 50 and 100 μM.
“Note that the MGN:b-CD 1:1 complex showed a higher antioxidant activity when compared with its free form, for MGN concentrations of 50 and 100 mmol L À1 .”
Quote in the paperSubstantial claim - Findingown data
MGN:b-CD complex has different physicochemical characteristics compared with free MGN.
“The results of FT-IR and DSC demonstrated that the MGN:b-CD complex has different physicochemical characteristics when compared with free MGN.”
Quote in the paperSubstantial claim - Findingown data
MGN alone has an ORAC value of 2.3 (2.3 times Trolox).
“the results showed that MGN alone has an ORAC value of 2.3, it means 2.3 times better than the standard molecule, trolox”
Quote in the paperSubstantial claim - Findingown data
AAPH-induced liposomal lipid peroxidation was observed in absence of antioxidants (negative controls).
“AAPH-induced liposomal lipid peroxidation was observed in the absence of antioxidants (negative controls, Fig. 7).”
Quote in the paperNot a substantial claim - Interpretationreasoning
At 500 μM, MGN is in excess in the medium consuming all DPPH.
“At this concentration, MGN is in excess in the medium consuming all DPPH.”
Quote in the paperNot a substantial claim - Interpretationown data
MGN was efficiently complexed in b-CD cavity by co-evaporation method.
“Thus, MGN was efficiently complexed in the b-CD cavity by the co-evaporation method.”
Quote in the paperSubstantial claim - Premisecitation
MGN has low solubility in water (0.111 mg/mL).
“However this antioxidant activity does not necessarily lead to an in vivo biological effect implying poor bioavailability, due to its low solubility in water: 0.111 mg/mL (Van der Merwe et al., 2012;Wang, Deng, Li, & Wang, 2007).”
Quote in the paperSubstantial claim0 of 2 sources checked- cites Van der Merwe et al., 2012 source
- cites Wang, Deng, Li, & Wang, 2007
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Premisecitation
The capacity of free radical scavenging by antioxidants does not necessarily correlate with the capacity of inhibition of lipid peroxidation.
“It has been shown that the capacity of free radical scavenging by antioxidants does not necessarily correlate with the capacity of inhibition of lipid peroxidation.”
Quote in the paperSubstantial claim0 of 1 sources checked- cites Niki, 2010 source
- Premisecitation
MGN's antioxidant activity does not necessarily lead to an in vivo biological effect.
“However this antioxidant activity does not necessarily lead to an in vivo biological effect implying poor bioavailability, due to its low solubility in water: 0.111 mg/mL (Van der Merwe et al., 2012;Wang, Deng, Li, & Wang, 2007).”
Quote in the paperSubstantial claim0 of 2 sources checked- cites Van der Merwe et al., 2012 source
- cites Wang, Deng, Li, & Wang, 2007
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
- Interpretationown data
The inclusion of MGN in b-CD favored membrane protection.
“The protective effect herein found is relevant, since the inclusion of MGN in b-CD favored the membrane protection.”
Quote in the paperSubstantial claim- Rests on an assumption: The antioxidant ability of Trolox inhibits lipid peroxidation.
- Premisecitation
1-OH and 3-OH of MGN are likely to suffer oxidation.
“It is also worth remembering that even though the 6-OH and 7-OH are the most important groups concerning the antioxidant activity of MGN, 1-OH and 3-OH (out of the cavity) are also likely to suffer the oxidation process (Gómez-Zaleta et al., 2006).”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites Gómez-Zaleta et al., 2006 source
- Interpretationreasoning
The ORAC-FL method was more effective in evaluation of antioxidant activity of MGN in a CD complex.
“The ORAC-FL method was more effective in the evaluation of the antioxidant activity of MGN in a CD complex.”
Quote in the paperSubstantial claim - Interpretationown data
The antioxidant activity of MGN is influenced by b-CD.
“In the present work, it was observed that the antioxidant activity of MGN is influenced by b-CD.”
Quote in the paperSubstantial claim
- Classified as probably not a substantial claim. 9
- The quote only partly states this claim. 2
- May combine two claims. 9
Probably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationPositions 6 and 7 of MGN are mainly responsible for its antioxidant property.
“According to Dar et al. (2005), positions 6 and 7 (Fig. 1b) of MGN are mainly responsible for its antioxidant property.”
Quote in the paperNot a substantial claim1 of 1 sources checked- cites Dar et al., 2005 source
The quote only partly states this claim.
FindingreasoningAt 500 μM, MGN in complexed form is not more reactive toward DPPH than free form.
“MGN in complexed form is more reactive toward DPPH than its free form, except at higher concentration 500 mmol L À1 .”
Quote in the paperNot a substantial claimMay combine two claims.
Findingown dataAt 50 μM, RSA-DPPH (%) is about 65% for MGN:b-CD complex vs about 28% for free MGN.
“For the MGN:b-CD (1:1) complex at a concentration of 50 mmol L À1 , the value of RSA-DPPH (%) is about 65%, while for its free form, it is about 28%.”
Quote in the paperSubstantial claimThe quote only partly states this claim.
Findingown dataAt 100 μM, RSA-DPPH (%) for MGN:b-CD complex increased to 78%.
“In the case of the complex at 100 mmol L À1 , the value increased to 78%.”
Quote in the paperSubstantial claimMay combine two claims.
Findingown dataLipid peroxidation assays showed MGN and MGN:b-CD complex have protective effects on membrane as well as Trolox.
“Lipid peroxidation assays have shown that MGN and MGN:b-CD complex have protective effects on the membrane as well as trolox”
Quote in the paperSubstantial claim- Rests on an assumption: The antioxidant ability of Trolox inhibits lipid peroxidation.
May combine two claims.
Findingown dataThe antioxidant activity of MGN:b-CD increases as amount of methanol and ethanol increases, reaching maximum when only organic solvent is used, with increase more pronounced for ethanol.
“However, in our work, it was observed that the antioxidant activity of MGN:b-CD increases as the amount of methanol and ethanol increases, reaching a maximum when only organic solvent is used, with this increase being more pronounced for ethanol.”
Quote in the paperSubstantial claimMay combine two claims.
InterpretationcitationORAC method was adequate to measure antioxidant activity of MGN:b-CD complex, but does not show capacity to inhibit oxidation and lipid peroxidation.
“The ORAC method was adequate to measure the antioxidant activity of MGN:b-CD complex, but does not show the capacity to inhibit oxidation and lipid peroxidation (Niki, 2010).”
Quote in the paperSubstantial claim0 of 1 sources checked- cites Niki, 2010 source
Probably not a substantial claim: may not pass S3 (load-bearing).
PremisecitationComplexation between substrate and CD can decrease antioxidant ability, as observed for carotenoids.
“which is different from other results in the literature that have shown that the complexation between the substrate and CD can decrease antioxidant ability, as observed for carotenoids (Polyakov, Leshina, Konovalova, Hand, & Kispert, 2004).”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites Polyakov et al., 2004 source
May combine two claims.
PremisecitationNMR signals for H-5 and H-8 of MGN in complexed form undergo downfield shifts, indicating aromatic hydrogen signals are influenced by b-CD.
“Ferreira et al. (2010) showed that the NMR signals for H-5 and H-8 (Fig. 1b) of MGN in the complexed form underwent downfield shifts from 6.8 to 6.9 d and from 7.4 to 7.6 d, respectively, indicating that its aromatic hydrogen signals are influenced by the presence of b-CD in the medium, increasing the antioxidant activity of the MGN:b-CD complex.”
Quote in the paperSubstantial claim0 of 1 sources checked- cites Ferreira et al., 2010 source
Classified as probably not a substantial claim. May combine two claims.
PremisecitationCyclodextrins can complex with a variety of guest molecules, enabling their solubility, stability, bioavailability, protection against light-induced decomposition, etc.
“This problem can be minimized by using cyclodextrins (CDs), that present special ability to complex with a variety of guest molecules, which enables their solubility, stability, bioavailability, protection against light-induced decomposition, to suppress unpleasant odors or tastes and achieve a controlled release of certain”
Quote in the paperSubstantial claim0 of 1 sources checked- cites Astray et al., 2009 source
Probably not a substantial claim: may not pass S3 (load-bearing).
Study design and conductnone givenThe temperature scale was calibrated using a-alumina powder.
“The temperature scale was calibrated using a-alumina powder.”
Quote in the paperNot a substantial claimMay combine two claims.
PremisecitationInclusion of MGN in CDs cavity increases its solubility and bioavailability.
“Other studies (Huang, He, Lu, Ge, & Guo, 2011;Teng, Yu, Zhai, Li, & Liu, 2007;Zhang et al., 2010) also show that the inclusion of MGN on the CDs cavity increases its solubility and bioavailability.”
Quote in the paperNot a substantial claim0 of 3 sources checkedProbably not a substantial claim: may not pass S3 (load-bearing). May combine two claims.
Study design and conductown dataA blank with FL and AAPH and five calibration solutions using Trolox were used in each ORAC assay.
“A blank with FL and AAPH, using water and ethanol instead of the antioxidant solution, and five calibration solutions using Trolox (0.5, 1.0, 1.5, 2.0 and 2.5 mmol L À1 ) were also used in each assay.”
Quote in the paperNot a substantial claimClassified as probably not a substantial claim.
PremisecitationCyclodextrins increase the antioxidant activity of many compounds.
“and still increase the antioxidant activity of many compounds (Lu, Cheng, Hub, Zhang, & Zou, 2009).”
Quote in the paperSubstantial claim0 of 1 sources checked- cites Lu et al., 2009
Couldn’t be matched to a paper in Crossref, so it can’t be checked.
Probably not a substantial claim: may not pass S3 (load-bearing).
Study design and conductown dataThe particle size of unilamellar vesicles was confirmed to be around 100 nm.
“The particle size was confirmed by Nanotrac-Zetatrac, NPA151-31A-0000-D30-10M model being around 100 nm.”
Quote in the paperNot a substantial claimMay combine two claims.
PremisecitationThe complexation of MGN in b-CD has been described, with stoichiometry 1:1 and apparent formation constant calculated.
“The complexation of MGN in b-cyclodextrin (b-CD) has been described by our group, its stoichiometry determined as 1:1 and its apparent formation constant (K F ) was calculated using the Benesie Hildebrand method and by cyclic voltammetry (Ferreira et al., 2010).”
Quote in the paperNot a substantial claim0 of 1 sources checked- cites Ferreira et al., 2010 source
Probably not a substantial claim: may not pass S3 (load-bearing).
Study design and conductnone givenThe b-CD aqueous solution and buffer were used as negative controls.
“The b-CD aqueous solution and buffer were used as negative controls.”
Quote in the paperNot a substantial claimProbably not a substantial claim: may not pass S3 (load-bearing).
Study design and conductnone givenAll measurements were performed in triplicate.
“All measurements were performed in triplicate.”
Quote in the paperNot a substantial claim
The paper relies on this without support.
It is still unknown whether entrapment in the internal cavity of CDs affects the antioxidant activity of MGN.
“However, it is still unknown whether entrapment in the internal cavity of CDs affects the antioxidant activity of MGN.”
The paper relies on this without support.
The antioxidant ability of Trolox inhibits lipid peroxidation.
“The antioxidant ability of trolox is well-known and it inhibits lipid peroxidation.”
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
Each contradiction between two passages listed here was confirmed by an independent check.
β-CD melting point is given as both 295 °C and 335 °C
MinorThe paper identifies the β-CD melting peak as close to 295 °C and the effect at 335 °C as thermal degradation. It later treats 335.0 °C as the original fusion temperature when describing the physical mixture.
“A sharp endothermic signal was observed close to 295 C corresponding to the melting point of b-CD, followed by endo-exo effects that are related to thermal degradation in 335 C.”
“the fusion temperature of b-CD experimented a reduction from 335.0 C to 271.4 C.”
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- Authors
- Ferreira, F. D. R., Valentim, I. B., Ramones, E. L. C., Trevisan, M. T. S., Olea-Azar, C., Perez-Cruz, F., de Abreu, F. C., & Goulart, M. O. F.
- Affiliations
- Universidade Federal de Alagoas (BR)
- Universidade Federal do Ceará (BR)
- Corresponding author
- Goulart, Marília Oliveira Fonseca
- Venue
- LWT - Food Science and Technology
- Publisher
- Elsevier BV
- Published
- 2013-04
- Volume
- 51
- Issue
- 1
- Pages
- 129-134
- ISSN
- 0023-6438 (ISSN-L)
- OpenAlex
- W2007704143
- Semantic Scholar
- 91eb1b0b8d86f1f662423c87a3324f01695ffc23
- Cited by
- 73
- References
- 30
- Citations by year
- 2026: 2 · 2025: 5 · 2024: 2 · 2023: 8 · 2022: 5 · 2021: 7 · 2020: 7 · 2019: 11 · 2018: 6 · 2017: 7 · 2016: 8 · 2015: 1 · 2014: 2 · 2013: 2
- FWCI
- 3.57
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- Locations
- LWT (publishedVersion)
- Universidad de Chile (submittedVersion, cc-by-nc-nd)
- Funders
- CNPq/PROSUL
- CAPES
- CAPES/PNPD
- FAPEAL
- BNB (Banco do Nordeste do Brasil)
- CNPq/PNPD
- INCT-Bioanalítica
- RENORBIO
- Topics
- Health Sciences › Medicine › Complementary and alternative medicine › Mangiferin and Mango Extracts
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Drug Solubulity and Delivery Systems
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Keywords
- mangiferin, β-cyclodextrin, inclusion complexes, antioxidant activity, free radical scavenging, DPPH radical, lipid peroxidation, membrane protection, solvent effects, co-evaporation
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