Thermal behavior and thermal degradation kinetic parameters of triterpene α, β amyrin

Júnior, Walter Ferreira da Silva; Pinheiro, Jonas Gabriel de Oliveira; Moreira, Carlos Demócedes Luís de França Almeida; Rüdiger, André Luis; Barbosa, Euzébio Guimarães; Lima, Émerson Silva; Júnior, Valdir Florêncio da Veiga; Júnior, Arnóbio Antônio da Silva; Aragão, Cícero Flávio Soares; Lima, Ádley Antonini Neves de

doi:10.1007/s10973-016-6046-x

Cited by 13 publications

(8 citation statements)

References 39 publications

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“…The band at the 3250–3400 cm −1 region is attributed to the hydroxyl group (O-H) attached to a cycloalkane chain and that of the 1031–1100 cm −1 region is associated with C-O bond vibration. Finally, another characteristic band is found in the 1400–1350 cm −1 region, which is due to the angular deformation of the dimethyl and methyl duplet [19].…”

Section: Resultsmentioning

confidence: 99%

“…The surface morphology of each individual compound and their respective ICs are presented in Figure 2. The ABAM’s surface is characterized by well-defined acicular structures with regular shapes and a three-dimensional appearance, which are characteristic of a crystalline compound [19]. βCD presents particles with crystalline structure in parallelogram format, as observed by Bulani [30].…”

Section: Resultsmentioning

confidence: 99%

“…ABAM was obtained following the protocol described by Silva-Júnior et al [19], from commercially available Burseraceae oi-resin from Manaus, Central Amazon (Brazil), where Protium heptaphyllum is the endemic species. The sample of ABAM used at this study is the same one that was previously purified, isolated and characterized by gas chromatography coupled with mass spectrometry (GCMS) and 1 H and 13 C nuclear magnetic ressonance (NMR), which presents more than 99% of purity and a correlation between the isomers α and β amyrin (as determined by NMR and confirmed by GCMS) of 2.64:1. βCD and HPβCD were purchased from Sigma-Aldrich ® (St. Louis, MO, USA).…”

Section: Methodsmentioning

confidence: 99%

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Inclusion Complexes of β and HPβ-Cyclodextrin with α, β Amyrin and In Vitro Anti-Inflammatory Activity

et al. 2019

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α, β amyrin (ABAM) is a natural mixture of pentacyclic triterpenes that has a wide range of biological activities. ABAM is isolated from the species of the Burseraceae family, in which the species Protium is commonly found in the Amazon region of Brazil. The aim of this work was to develop inclusion complexes (ICs) of ABAM and β-cyclodextrin (βCD) and hydroxypropyl-β-cyclodextrin (HPβCD) by physical mixing (PM) and kneading (KN) methods. Interactions between ABAM and the CD’s as well as the formation of ICs were confirmed by physicochemical characterization in the solid state by Fourier transform infrared (FTIR), scanning electron microscopy (SEM), X-ray diffraction (XRD), thermogravimetry (TG) and differential scanning calorimetry (DSC). Physicochemical characterization indicated the formation of ICs with both βCD and HPβCD. Such ICs were able to induce changes in the physicochemical properties of ABAM. In addition, the formation of ICs with cyclodextrins showed to be an effective and promising alternative to enhance the anti-inflammatory activity and safety of ABAM.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Inclusion Complexes of β and HPβ-Cyclodextrin with α, β Amyrin and In Vitro Anti-Inflammatory Activity

et al. 2019

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“…It is noted that the resin (Δm 1 = 9.18%) presents a higher variation in mass loss than the adhesive (Δm 1 = 4.10%), which may be due to the thermal processes of heating at 100 °C until liquefaction and curing at 60 °C used for preparing the adhesive. The second thermal event is observed between 201 and 435 °C and is related to the loss of the main components (amyrins and diols) of the Protium heptaphyllum resin, as reported by Silva Junior et al [20] and Vieira Junior et al [17] . Silva Junior et al [20] showed that the isomers α-and β-amyrins, the major components of Protium heptaphyllum resin are degraded in the range of 210 to 380 ºC.…”

Section: Characterization Of Precursor Materials and Bioadhesivementioning

confidence: 65%

Development of a bio-based adhesive from Protium heptaphyllum resin

et al. 2021

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In this work, a bio-based adhesive is prepared from Protium heptaphyllum resin. The resin is first characterized by 1 H and 13 C nuclear magnetic resonance spectroscopy and the bioadhesive is then prepared using a simple mixture of the resin with linseed oil, catalyzed by cobalt octanoate, to induce crosslinking. The precursors and bioadhesive obtained are characterized by thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and Fourier transform infrared spectroscopy (FTIR). The NMR analysis shows the presence of groups of triterpenes, such as α-and β-amyrins, and diols, such as brein and maniladiol. Thermogravimetric analysis reveals that the resin has less thermal stability than the bioadhesive. Mechanical tests indicate that the bioadhesive has greater adhesion strength compared to the commercial adhesive, reaching an average stress at break of 7.66 and 0.113 MPa for the wood and carbon steel substrates, respectively. In conclusion, the bioadhesive can be used for the production of composites.

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“…Amyrins, hydroxylated monounsaturated alcohols obtained from several triterpenic skeletons, mainly from ursane and oleanane, are commonly observed in apolar extracts of plants and abundantly available in oil resins that is produced by Burseraceae species, well-known incense, frankincense or breu. [22][23][24][25] This study evaluated the antiprotozoal activities of twelve triterpenoid and combinatorial effects, as well as the cytotoxicity against mammalian cells. The structure-activity relationship (SAR) between the chemical structure and biological properties of the compounds was also suggested.…”

Section: Introductionmentioning

confidence: 99%

Anti-Trypanosoma Activity and Synergistic Effects of Natural and Semi-Synthetic Triterpenes and Predominant Cell Death through Autophagy in Amastigote Forms

Bossolani

Ueda-Nakamura

Silva

et al. 2017

J. Braz. Chem. Soc.

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Chagas' disease is a parasitic disease with unsatisfactory treatment, mainly in chronic stage. This study aimed to evaluate the trypanocidal activity and action mechanisms of α/β-amyrin and its semisynthetic derivatives, together with four isolated natural triterpenes, tested against trypomastigote and amastigote forms. The structure-activity relationship was suggested and cytotoxicity was measured. In general, greater polar compounds may have improved the selectivity to the protozoan. Action mechanisms were only performed for the amastigotes of Trypanosoma cruzi by evaluating the ultrastructural alterations, membrane permeability, mitochondrial membrane potential and cell volume, since the majority of compounds displayed promising antiamastigote activities. Triterpenes promoted changes on mitochondrial membrane potential and ultrastructural features that suggest autophagy processes. Both combinations between α/β-amyrin and 3-O-acetyl-11-oxo-α/β-amyrin and 3-O-acetyl-α/β-amyrin with benznidazole displayed synergistic effects against amastigotes and antagonistic effects on LLCMK 2 cells. The antiamastigote activities, chemical derivatization, drug combinations and action mechanisms revealed to be crucial approaches toward this chronic disease.

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Thermal behavior and thermal degradation kinetic parameters of triterpene α, β amyrin

Cited by 13 publications

References 39 publications

Inclusion Complexes of β and HPβ-Cyclodextrin with α, β Amyrin and In Vitro Anti-Inflammatory Activity

Inclusion Complexes of β and HPβ-Cyclodextrin with α, β Amyrin and In Vitro Anti-Inflammatory Activity

Development of a bio-based adhesive from Protium heptaphyllum resin

Anti-Trypanosoma Activity and Synergistic Effects of Natural and Semi-Synthetic Triterpenes and Predominant Cell Death through Autophagy in Amastigote Forms

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