Vouacapane diterpenoids isolated from Pterodon and their biological activities

Oliveira, Leandra A. R. de; Oliveira, Gerlon de Almeida Ribeiro; Borges, Leonardo Luiz; Bara, Maria Teresa Freitas; Silveira, Dâmaris

doi:10.1016/j.bjp.2017.05.014

Cited by 18 publications

(15 citation statements)

References 89 publications

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“…Moreover, 6α,7β‐dihydroxyvouacapan‐17β‐oic acid, methyl 6α,7β‐dihydroxyvouacapan‐17β‐oate, and 6α‐hydroxyvouacapan‐7β,17β‐lactone isolated from the herb Pterodon sp . showed larvicidal effects against this dengue vector with LC 50 values of 14.69, 21.76, and 50.08 μg/ml, respectively) (Oliveira, Oliveira, Borges, Bara, & Silveira, ). Recently, diterpenes‐containing essential oils of Stachys tmolea subsp.…”

Section: Review Findingsmentioning

confidence: 99%

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Diterpenes and their derivatives as promising agents against dengue virus and dengue vectors: A literature‐based review

Islam

Mubarak

2019

Phytotherapy Research

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Dengue, a mosquito‐borne viral disease, causes about 100 million cases of infection annually. It is a major public concern, and if left untreated or improperly diagnosed, may cause serious health problems or even death. Historically, dengue has not considered priorities for pharmaceutical companies made the available treatment options. Therefore, medicinal scientists are revealing new insights and enabling novel interventions and approaches to dengue prevention and control. Diterpenes, a class of terpenes have gained much attention due to their diverse biological effects. This review aimed at summarizing available evidences of diterpenes and their derivatives acting against dengue virus and their vectors. For this, an updated search was made in the databases: PubMed and ScienceDirect by using specific keywords. Among the 117 published reports, a total of 30 articles was included in this review. Findings suggest that a number of diterpenes and/or their derivatives act against dengue virus and their two potential vectors namely Aedes aegypti and Ae. albopictus. In conclusion, diterpenes and their derivatives may have the potential alternative therapeutic tools for the management of dengue virus and some associated diseases transmitted by Aedes mosquito.

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Section: Review Findingsmentioning

confidence: 99%

“…showed larvicidal effects against this dengue vector with LC 50 values of 14.69, 21.76, and 50.08 μg/ml, respectively) (Oliveira, Oliveira, Borges, Bara, & Silveira, 2017). Recently, diterpenes-containing essential oils of Stachys tmolea subsp.…”

Section: Along This Line the Chlorophyll-derived Diterpenoid Phytol mentioning

confidence: 99%

Diterpenes and their derivatives as promising agents against dengue virus and dengue vectors: A literature‐based review

Islam

Mubarak

2019

Phytotherapy Research

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“…Isoflavones and diterpenes (vouacapane-type) are the main components of oleoresin. [28][29][30][31][32][33][34] Vouacapane diterpenoids are low-tomedium polarity secondary metabolites. Studies suggested the vouacapane skeleton as the main pharmacophore, supported by pharmacological investigations of isolated compounds, as well as P. emarginatus oleoresin-derived vouacapane diterpenoids.…”

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confidence: 99%

“…Studies suggested the vouacapane skeleton as the main pharmacophore, supported by pharmacological investigations of isolated compounds, as well as P. emarginatus oleoresin-derived vouacapane diterpenoids. 32 Chemoinformatic and in vivo investigations suggested the thermodynamic feasibility of P. emarginatus-derived vouacapane diterpenoid docking in both human and murine cyclooxygenase-2 (COX-2), 28 as well as a possible impairment of pro-inflammatory mediators from the prostaglandin E2 (PGE2) pathway, 35 which might indicate the involvement of diterpenoid derivatives in the reported P. emarginatus oleoresin antinociceptive and anti-inflammatory action. 36 Given the importance of elucidating the pharmacodynamics of P. emarginatus products, the anti-inflammatory actions of oleoresin and vouacapanes 6α,19β-diacetoxy-7β,14β-A c c e p t e d M a n u s c r i p t dihydroxyvouacapan (V1), 6α-acetoxy-7β,14β-dihydroxyvouacapan (V2), and methyl 6α-acetoxy-7βhydroxyvouacapan-17β-oate (V3) (Figure 1) were evaluated in HaCaT human keratinocytes exposed to UVA radiation or 5-fluorouracil (5-FU).…”

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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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“…TEIXEIRA, 1990;SANTOS et al, 2010;ARRAIS-SILVA et al, 2014;DONATI et al, 2015). Na oleorresina obtida a partir dos frutos, também foi encontrada uma grande variedade de substâncias como terpenóides do tipo furanoditerpenos (esqueleto vouacapânico) (ARRIAGA et al, 2000;SPINDOLA et al, 2009;HOSCHEID et al, 2012;CABRAL et al, 2013;NUCCI-MARTINS et al, 2015;OLIVEIRA et al, 2017;NETO, 1976;NUNAN et al, 1982apud OLIVEIRA, 2016. Na casca também foram encontrados triterpenóides envolvidos no efeito anti-inflamatório (DE MORAES et al, 2012).…”

Section: Pterodon Pubescens Benth (Sucupira)unclassified

Extração supercrítica, caracterização e avaliação da ação antiproliferativa em célulastumorais in vitro de compostos bioativos da Sucupira (Pterodon pubescens Benth).

Brasil¹

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RESUMOO presente trabalho tem como objetivo o estudo da extração supercrítica dos compostos bioativos dos frutos da Sucupira (Pterodon pubescens Benth), utilizando dióxido de carbono supercrítico como solvente. Proveniente do Cerrado brasileiro, a Sucupira é popularmente conhecida como analgésico e anti-inflamatório natural. Para o estudo, foi realizado um delineamento experimental 2 3 para análise da influência da temperatura (32 ºC a 52 ºC), pressão (200 bar a 300 bar) e da razão S/F (30 a 90) no rendimento do processo. Esses dados foram comparados com a extração em aparelho Soxhlet, utilizando hexano como solvente durante 8 h, que apresentou rendimento mássico de 13,05 ± 0,29%. A extração supercrítica apresentou rendimento ótimo de 20,9% (temperatura de 52 ºC, pressão de 300 bar e S/F= 90), sendo a temperatura a variável independente de maior efeito no rendimento mássico. A análise em HPLC demonstrou, quantitativamente, que as amostras resultantes da extração supercrítica apresentaram maior concentração do diterpeno 404 (6α-acetoxi-7β-hydroxi-vouacapan-17βoato e 6α-hidroxi-7β-acetoxi-vouacapan-17β-oato) e do diterpeno 362 (éster 6α-7β-dihidroxivouacapan-17β-oato de metila), quando comparadas ao extrato hexânico. O ensaio 8, de maior rendimento, apresentou uma concentração de 0,14 mg do diterpeno 404 por mg de droga vegetal e de 0,02 mg do diterpeno 362 por mg de droga vegetal. Em todas as amostras foi identificada a presença do sesquiterpeno β-cariofileno, presente em óleos essenciais, evidenciando que o extrato obtido é uma mistura de óleo essencial e óleo fixo. Por fim, o teste antiproliferativo realizado em células tumorais humanas in vitro indicaram maior seletividade do extrato supercrítico para a linhagem 786-0 (Rim), sendo que os ensaios 2 (T=52 ºC, P=200 bar e S/F=30), 7 (T=32 ºC, P= 300 bar e S/F= 90), 8 (T=52 ºC, P=300 bar e S/F=90) e 9 (T=42 ºC, P=250 bar e S/F= 60) também mostraram-se seletivos e dependentes da concentração para as linhagens PC-3 (Próstata), MCF-7 (Mama) e NCI/ADR (Ovário). O ensaio 2 (T=52 ºC, P=200 bar e S/F= 30), apresentou atividade antiproliferativa moderada para a linhagem 786-0 (Rim), com TGI (Total Growth Inhibition) igual a 14 µg/mL. Dessa forma, evidenciou-se que o extrato supercrítico da Sucupira apresentou maior concentração de diterpenos vouacapanos quando comparado ao extrato hexânico, juntamente com uma seletividade diferenciada no teste antiproliferativo in vitro para a linhagem 786-0 (Rim), quando comparado aos estudos reportados na literatura que utilizaram métodos convencionais de extração.Palavras-chave: Extração supercrítica, Pterodon pubescens Benth, Ação antiproliferativa in vitro, Biocompostos.

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Vouacapane diterpenoids isolated from Pterodon and their biological activities

Cited by 18 publications

References 89 publications

Diterpenes and their derivatives as promising agents against dengue virus and dengue vectors: A literature‐based review

Diterpenes and their derivatives as promising agents against dengue virus and dengue vectors: A literature‐based review

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

Extração supercrítica, caracterização e avaliação da ação antiproliferativa em célulastumorais in vitro de compostos bioativos da Sucupira (Pterodon pubescens Benth).

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