Derivatives of furanditerpenes from Pterodon genus: Pharmacological studies disclose their potential as chronic pain relief in mice

Spindola, Humberto M.; Grando, Rogério; Figueiredo, Mariana C.; Basting, Rosanna Tarkany; Queiroz, Nubia Cassia; Fátima, Ângelo de; Carvalho, João Ernesto de; Wang, Zaijie J.; Foglio, Mary Ann

doi:10.1016/j.ejphar.2017.03.030

Cited by 7 publications

(3 citation statements)

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“…Sucupira essential oil is obtained from the fruits of the Brazilian plants of the genus Pterodon, commonly known as "faveira", "sucupira", "sucupira-branca", "fava-de-sucupira", or "sucupira-lisa" and has been recognized as promising agent for the management of DM and its complications [17,28]. Traditional medicine has early recognized its diverse biological properties, (e.g., anti-nociceptive, anti-inflammatory, antioxidant, antimicrobial, anticancer, muscle relaxant, hypoglycemic, and lipolytic activities) [18].…”

Section: Introductionmentioning

confidence: 99%

Sucupira Oil-Loaded Nanostructured Lipid Carriers (NLC): Lipid Screening, Factorial Design, Release Profile, and Cytotoxicity

et al. 2020

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Essential oils are odorant liquid oily products consisting of a complex mixture of volatile compounds obtained from a plant raw material. They have been increasingly proven to act as potential natural agents in the treatment of several human conditions, including diabetes mellitus (DM). DM is a metabolic disorder characterized by chronic hyperglycemia closely related to carbohydrate, protein and fat metabolism disturbances. In order to explore novel approaches for the management of DM our group proposes the encapsulation of sucupira essential oil, obtained from the fruits of the Brazilian plants of the genus Pterodon, in nanostructured lipid carriers (NLCs), a second generation of lipid nanoparticles which act as new controlled drug delivery system (DDS). Encapsulation was performed by hot high-pressure homogenization (HPH) technique and the samples were then analyzed by dynamic light scattering (DLS) for mean average size and polydispersity index (PI) and by electrophoretic light scattering (ELS) for zeta potential (ZP), immediately after production and after 24 h of storage at 4 °C. An optimal sucupira-loaded NLC was found to consist of 0.5% (m/V) sucupira oil, 4.5% (m/V) of Kollivax® GMS II and 1.425% (m/V) of TPGS (formulation no. 6) characterized by a mean particle size ranging from 148.1 ± 0.9815 nm (0 h) to 159.3 ± 9.539 nm (at 24 h), a PI from 0.274 ± 0.029 (0 h) to 0.305 ± 0.028 (24 h) and a ZP from −0.00236 ± 0.147 mV (at 0 h) to 0.125 ± 0.162 (at 24 h). The encapsulation efficiency and loading capacity were 99.98% and 9.6%, respectively. The optimized formulation followed a modified release profile fitting the first order kinetics, over a period of 8 h. In vitro cytotoxicity studies were performed against Caco-2 cell lines, for which the cell viability above 90% confirmed the non-cytotoxic profile of both blank and sucupira oil-loaded NLC.

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Section: Introductionmentioning

confidence: 99%

Sucupira Oil-Loaded Nanostructured Lipid Carriers (NLC): Lipid Screening, Factorial Design, Release Profile, and Cytotoxicity

et al. 2020

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“…The literature reports that many Fabaceae species have anti-inflammatory diterpenoids whose therapeutic target may include phospholipase A2. 50 , 51 This enzyme is responsible for fatty acid cleavage, rendering arachidonic and lysophosphatidic acid, which are nonetheless involved in the metabolic signaling of inflammation. 52 As the anti-inflammatory properties of the oleoresin are well recognized in Brazilian folk medicine, 53 , 54 the significant inhibition of phospholipase A2 by this compound is a remarkable finding.…”

Section: Resultsmentioning

confidence: 99%

The Potential of Vouacapanes from Pterodon Emarginatus Vogel against COVID-19 Cytokine Storm

et al. 2021

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Purpose: The emergence of the COVID-19 pandemic has led to the search for potential therapeutic responses for various aspects of this disease. Fruits of Pterodon emarginatus Vogel (Fabaceae), sucupira, have been used in Brazilian traditional medicine because of their anti-inflammatory properties, which have been proven in vivo, in vitro, and in silico. Therefore, the aim of this work is to evaluate P. emarginatus oleoresin and isolated diterpenes by in vitro anti-inflammatory models. Methods: In this study, the mechanisms underlying the anti-inflammatory activity of Pterodon emarginatus oleoresin and vouacapanes 6α,19β-diacetoxy-7β,14β-dihydroxyvouacapan (V1), 6α-acetoxy-7β,14β-dihydroxyvouacapan (V2), and methyl 6α-acetoxy-7β-hydroxyvouacapan-17β-oate (V3) were investigated in HaCaT cells. Results: Oleoresin, V2, and V3 inhibited phospholipase A2 (30.78%, 24.96%, and 77.64%, respectively). Both vouacapanes also inhibited the expression of COX-2 (28.3% and 33.17%, respectively). The production of interleukin IL-6 was inhibited by oleoresin by 35.47%. However, oleoresin did not interfere with Nrf-2 expression or IL-8 production. Conclusion: The results support the ethnomedicinal use of P. emarginatus oleoresin as an anti-inflammatory herbal medicine, and also highlight Pterodon emarginatus oleoresin and isolated vouacapanes as an attractive therapeutic approach for COVID-19 through the reduction or chronological control of the inflammatory mediators IL-6, COX-2, phospholipase A2, and INF-y (indirectly) during the SARS-CoV-2 infection process.

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“…fruits (Fabaceae), known in Brazil as sucupira, is used in folk medicine for their analgesic and anti-inflammatory properties as well as for the treatment of rheumatism [1]. The anti-inflammatory and anti-edematogenic pharmacological activities are reported [2,3]. Furthermore, compounds isolated from Pterodon extract with a vouacapan moiety have been reported as a source with pharmacological activity against inflammatory and nociceptive processes and antiproliferative activities in tumor cells [4,5].…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative Effects of Pterodon pubescens Extract and Isolated Diterpenes in HaCaT Cells

et al. 2020

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Pterodon pubescens fruits are popularly used because of their analgesic and anti-inflammatory actions, which are attributed to the isolated compounds with a vouacapan skeleton. This work aimed to evaluate the antiproliferative and anti-inflammatory effects of a P. pubescens fruit dichloromethane extract and the vouacapan diterpene furan isomerʼs mixture (1 : 1) (6α-hydroxy-7β-acetoxy-vouacapan-17β-oate methyl ester and 6α-acetoxy-7β-hydroxy-vouacapan-17β-oate methyl ester isomers) in HaCaT cells using the cell migration and the BrDU incorporation assay. Levels of IL-8 were measured by ELISA after TNF-α stimulation. HPLC/DAD analysis of the extract revealed the expressive presence of vouacapan diterpene furan isomerʼs mixture. P. pubescens extract (1.5625 – 25 µg/mL) and vouacapan diterpene furan isomerʼs mixture (3.125 – 50 µM) inhibited cell proliferation as indicated by a decreased BrdU-incorporation. For the evaluation of cell migration, time-lapse microscopy was used. P. pubescens presented inhibition on cell migration at all concentrations tested (3.125 – 12.5 µg/mL), whereas for the VDFI mixture, the inhibition was only observed at the highest concentrations (12.5 and 25 µM) tested. Furthermore P. pubescens extract and vouacapan diterpene furan isomerʼs mixture significantly decreased IL-8 levels. Our results showed antiproliferative and anti-inflammatory effects on HaCaT cells treated with the extract and the vouacapan isomerʼs mixture, without affecting cell viability. These activities could be attributed to the voucapan molecular structures. In conclusion, topical products developed of P. pubescens extract or the voucapan isomerʼs mixture should be further studied as a potential product for local treatment against hyperproliferative lesions as in psoriasis vulgaris, representing an alternative treatment approach.

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Derivatives of furanditerpenes from Pterodon genus: Pharmacological studies disclose their potential as chronic pain relief in mice

Cited by 7 publications

References 50 publications

Sucupira Oil-Loaded Nanostructured Lipid Carriers (NLC): Lipid Screening, Factorial Design, Release Profile, and Cytotoxicity

Sucupira Oil-Loaded Nanostructured Lipid Carriers (NLC): Lipid Screening, Factorial Design, Release Profile, and Cytotoxicity

The Potential of Vouacapanes from Pterodon Emarginatus Vogel against COVID-19 Cytokine Storm

Antiproliferative Effects of Pterodon pubescens Extract and Isolated Diterpenes in HaCaT Cells

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