A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark

Malheiros, Ângela; Filho, Valdir Cechinel; Schmitt, C.; Santos, Adair R.S.; Scheidt, Cristiano; Calixto, João B.; Monachè, Franco Delle; Yunes, Rosendo A.

doi:10.1016/s0031-9422(00)00515-x

Cited by 53 publications

(31 citation statements)

References 15 publications

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“…As well, previous studies [40][41][42] indicated that a mixture of at least three sesquiterpenes, identified as being polygodial (Figure 14), 1-β-(ρ-methoxycinnamoyl polygodial and drimanial (Figure 15), appear to be the main constituents present in the park of plant D. winteri that are accountable for the marked antinociceptive, anti-inflammatory and anti-allergic effects of the crude extract. With regard to the relatively high concentrations of polygodial and to a lesser extent, drimanial in the park of D. winteri, it can be proposed that the two sesquiterpenes are the most relevant active compounds and are responsible for the major pharmacological activities of the plant.…”

Section: Polygodial Sesquiterpenessupporting

confidence: 74%

Natural Products as a Source for Novel Analgesic Compounds

Abdel-Rahman¹

2017

Pain Relief - From Analgesics to Alternative Therapies

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Natural products have an important role in the discovery of analgesic drugs along with the determining of the complex mechanisms involved in pain transmission and pain relief. Lately, several substances with antinociceptive actions have been purified from natural sources and further identified, resulting in novel structural classes and more understanding of the underlying pharmacological mechanisms of actions. Yet, natural products still hold great potential for the discovery of novel agents for treatment of pain disorders and potentially drug addictions with exciting pharmacological profiles (i.e. no side effects, no addictive potential). The aim of this chapter is to highlight some active compounds derived from natural sources that possess analgesic properties. Additionally, the identification of new compounds derived from natural sources could lead to great understanding of the underlying pharmacological mechanisms of action, which will be addressed in this chapter as well.

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Section: Polygodial Sesquiterpenessupporting

confidence: 74%

Natural Products as a Source for Novel Analgesic Compounds

Abdel-Rahman¹

2017

Pain Relief - From Analgesics to Alternative Therapies

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“…This class of sesquiterpenes occurs in a restrict group of angiosperms, such as Winteraceae, and has attracted particular interest because of their wide variety of biological activity (Jansen and Groot 1991;André et al 1999;Aranda et al 2001;Malheiros et al 2001;Malheiros et al 2005). A number of these sesquiterpenes has been reported in Drimys, especially drimenol and polygodial, whose presence have been observed in all species.…”

Section: Resultsmentioning

confidence: 99%

Chemical composition and larvicidal properties of the essential oils from Drimys brasiliensis Miers (Winteraceae) on the cattle tick Rhipicephalus (Boophilus) microplus and the brown dog tick Rhipicephalus sanguineus

et al. 2007

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The essential oil obtained from leaves and stem barks of the Southern Brazilian native Drimys brasiliensis Miers, a tree with medicinal properties, was analyzed by gas chromatography (GC) and GC/mass spectrometry (MS). The oil was characterized by sesquiterpenoids (66%), cyclocolorenone being the most abundant (30.4%), followed by bicyclogermacrene (11.8%) and alpha-gurjunene (6.0%). Laboratory tests were carried out to determine the toxicity of the essential oil on larvae of the cattle tick Rhipicephalus (Boophilus) microplus and the brown dog tick Rhipicephalus sanguineus by the larval immersion test. It was observed that the oil was lethal, killing 100% of the larvae of both ticks at the doses of 25, 12.5, and 6.25 microl/ml. The lowest dose tested, 3.125 microl/ml, was also toxic, killing 95-98% of the larvae.

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“…21, No. 9, 2010 including antibacterial, 2 anti-inflammatory, 3 anti-allergic, 3 antifungal, [4][5][6] antinociceptive, [7][8][9] anti-hyperalgesic, 10 and antibacterial. 11 Nevertheless, there are only two works about the chemical composition of D. brasiliensis, in which the same type of drimane sesquiterpenes have been found, such as confertifolin, drimanial, valdiviolide, polygodial, 1-b-(pmethoxycinnamoyl)polygodial and 1-b-(p-cumaroyloxy) polygodial.…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, the biological activities of the crude oils were compared to that evaluated to sesquiterpene polygodial, which is the main constituent from the stem bark of Drimys species and responsible from the pharmacological effects for the extracts prepared from these plants. 3,7,16,17 However, the potential observed to the analyzed oils could contribute to explain the popular use of bark infusion of D. brasiliensis to the pain treatment, since the components of the essential oils also showed anti-inflammatory effects. …”

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confidence: 99%

Chemical composition and anti-inflammatory evaluation of essential oils from leaves and stem barks from Drimys brasiliensis Miers (Winteraceae)

Lago¹,

Carvalho²,

Silva³

et al. 2010

J. Braz. Chem. Soc.

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Os óleos essenciais das folhas e das cascas do tronco de Drimys brasiliensis Miers (Winteraceae) foram obtidos individualmente por hidrodestilação e suas composições químicas foram determinadas através de análise por CG/DIC e CG/EM. Os principais constituintes identificados foram monoterpenos (folhas 4,31% e cascas do tronco 90,02%) e sesquiterpenos (folhas 52,31% e cascas do tronco 6,35%). Adicionalmente, o sesquiterpeno poligodial foi isolado do extrato em hexano das cascas do tronco de D. brasiliensis após fracionamento cromatográfico e caracterizado por métodos espectroscópicos. Visando a avaliação do potencial anti-inflamatório, os óleos essenciais brutos e o sesquiterpeno poligodial foram submetidos à bioensaios para avaliação da toxicidade aguda destes compostos bem como das atividades anti-inflamatória e antinociceptiva induzidas por carragenina e formalina em ratos. Nossos resultados mostraram que o óleo essencial bruto obtido das cascas do tronco reduziu significativamente o edema induzido por carragenina. O efeito anti-inflamatório induzido pelo óleo das cascas do tronco (a 200 mg kg -1 ) foi similar ao observado para indometacina (a 10 mg kg -1 ) e superior ao poligodial (a 200 mg kg -1 ) em 30 e em 60 min após administração. A resposta inflamatória induzida pela formalina foi efetiva para o óleo das cascas do tronco (62,5%) em comparação ao poligodial (50,0%).The essential oils from leaves and stem barks from Drimys brasiliensis Miers (Winteraceae) were individually obtained by hydrodistillation and their compounds characterized by use of GC/FID and GC/MS. The main identified derivatives were monoterpenes (leaves 4.31% and stem barks 90.02%) and sesquiterpenes (leaves 52.31% and stem barks 6.35%). Additionally, the sesquiterpene polygodial was isolated from hexane extract from stem barks of D. brasiliensis after chromatographic steps and characterized by spectroscopic means, mainly NMR. Aiming the evaluation of anti-inflammatory potential, the crude essential oils and the sesquiterpene polygodial were subjected to bioassays to evaluate the acute toxicity of these compounds as well as the anti-inflammatory and antinociceptive activities induced by carrageenan and formalin in mices. Ours results showed that essential oil obtained from the stem barks significantly reduced the oedema induced by carrageenan. The anti-inflammatory effect induced by stem barks oil (at 200 mg kg -1 ) was similar to observed for indomethacin (at 10 mg kg -1 ) and superior for polygodial (at 200 mg kg -1 ) in 30 and 60 min after the administration of essential oils. The inflammatory response induced by formalin was effective to the stem barks oil (62.5%) in comparison to polygodial (50.0%).Keywords: Drimys brasiliensis Miers, essential oil composition, antinociceptive, antiinflammatory, acute toxicity IntroductionDrimys brasiliensis Miers belongs to Winteraceae family, whose occurrence is restrict to South America. This species is known in Brazil with a vernacular name "cascad'anta" and has been used in folk medicine as analg...

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A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark

Cited by 53 publications

References 15 publications

Natural Products as a Source for Novel Analgesic Compounds

Natural Products as a Source for Novel Analgesic Compounds

Chemical composition and larvicidal properties of the essential oils from Drimys brasiliensis Miers (Winteraceae) on the cattle tick Rhipicephalus (Boophilus) microplus and the brown dog tick Rhipicephalus sanguineus

Chemical composition and anti-inflammatory evaluation of essential oils from leaves and stem barks from Drimys brasiliensis Miers (Winteraceae)

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