Two unusual rotenoid derivatives, 7a-O-methyl-12a-hydroxydeguelol and spiro-13-homo-13-oxaelliptone, from the seeds of Derris trifoliata

Yenesew, Abiy; Kiplagat, John T.; Derese, Solomon; Midiwo, Jacob O.; Kabaru, J. M.; Heydenreich, Matthias; Peter, Martin G.

doi:10.1016/j.phytochem.2006.01.002

Cited by 31 publications

(28 citation statements)

References 8 publications

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“…Species of this genus are known by their larvicidal, antiviral, anticancer, hepatoprotective and antioxidant activities (Andel et al, 2000;Andrei et al, 1997Andrei et al, , 2000Jang et al, 2003;Khatri et al, 2009;Niassy et al, 2005;Pezzuto et al, 1999;Saleem et al, 2001;Vasconcelos et al, 2009;Yenesew et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

Tephrosia sinapouethyl acetate extract inhibits inflammatory pain in mice: Opioid receptor dependent inhibition of TNFαand IL-1βproduction

Martínez¹,

Zarpelon²,

Cardoso³

et al. 2013

Pharmaceutical Biology

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Context: Tephrosia toxicaria is currently known as Tephrosia sinapou (Buc'hoz) A. Chev. (Fabaceae) and is a source of compounds such as flavonoids that inhibit inflammatory pain. Objective: To investigate the analgesic effect and mechanisms of the ethyl acetate extract of T. sinapou in inflammatory pain in mice. Materials and methods: Behavioral responses were evaluated using mechanical (1-24 h) and thermal hyperalgesia (0.5-5 h), writhing response (20 min) and rota-rod (1-5 h) tests. Neutrophil recruitment (myeloperoxidase activity), cytokines (tumor necrosis factor [TNF]a and interleukin [IL]-1b), aspartate aminotransferase (AST) and alanine aminotransferase (ALT) serum levels were determined by colorimetric assays. Pharmacological treatments were opioid receptor antagonist (naloxone, 0.1-1 mg/kg) and control opioid (morphine, 5 mg/kg). Inflammatory stimuli were carrageenin (100 mg/paw), complete Freund's adjuvant (CFA, 10 ml/paw), prostaglandin E 2 (PGE 2 , 100 ng/paw) and acetic acid (0.8%). Results: The intraperitoneal pre-treatment with extract inhibited in a dose-dependent (30-300 mg/kg) dependent manner the mechanical hyperalgesia induced by carrageenin (up to 93% inhibition). The post-treatment (100 mg/kg) inhibited CFA-induced hyperalgesia (up to 63% inhibition). Naloxone (1 mg/kg) prevented the inhibitory effect of the extract over carrageenin-induced mechanical (100%) and thermal (100%) hyperalgesia, neutrophil recruitment (52%) and TNFa (63%) and IL-1b (98%) production, thermal threshold in naïve mice (99%), PGE 2 -induced mechanical hyperalgesia (88%) and acetic acid-induced writhing response (49%). There was no significant alteration in the rota-rod test, and AST and ALT serum levels by extract treatment. Discussion and conclusion: Tephrosia sinapou ethyl acetate extract reduces inflammatory pain by activating an opioid receptor-dependent mechanism.

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Section: Introductionmentioning

confidence: 99%

Tephrosia sinapouethyl acetate extract inhibits inflammatory pain in mice: Opioid receptor dependent inhibition of TNFαand IL-1βproduction

Martínez¹,

Zarpelon²,

Cardoso³

et al. 2013

Pharmaceutical Biology

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“…Species of this genus are known by the presence of compounds with larvicidal, antiviral, anti-cancer and antioxidant activities (Andel, 2000;Andrei et al, 1997;Andrei et al, 2000;Jang et al, 2003;Niassy et al, 2005;Pezzuto et al, 1999;Saleem et al, 2001;Vasconcelos et al, 2009;Yenesew et al, 2006). Preliminary data on the composition analysis of ethyl acetate extract of T. sinapou, also known as T. toxicaria, revealed the presence of flavonoids, including novel compounds.…”

Section: Introductionmentioning

confidence: 99%

Tephrosia sinapou extract reduces inflammatory leukocyte recruitment in mice: effect on oxidative stress, nitric oxide and cytokine production

Martínez

Zarpelon

Zimermann

et al. 2012

Rev. bras. farmacogn.

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Abstract:Tephrosia toxicaria (Sw.) Pers., which is currently known as T. sinapou (Buc'hoz) A. Chev., Fabaceae, is a source of compounds such as fl avonoids, however, few studies addressed the anti-infl ammatory and antioxidant effects of T. sinapou. Therefore, we evaluated the antioxidant mechanisms of the T. sinapou ethyl acetate extract in vitro, and whether the extract affects leukocyte recruitment in four models of infl ammation and the involvement of nitric oxide and cytokines in its mechanism. In vitro, it was observed that the extract presented hydrogen donating ability to 2,2-diphenyl-1-picryl-hydrazyl radical (DPPH • ), 2,2'-azino-di-(3-ethylbenzthiazoline-6-sulphonic acid) radical (ABTS + ), and also effi ciently inhibited iron-dependent and independent lipid peroxidation and iron chelation assays. In vivo, it inhibited the recruitment of total leukocytes and neutrophil induced by carrageenin, zymosan, glycogen and lipopolysaccharide in the peritoneal cavity of mice. Two mechanisms were detected: 1) T. sinapou effect on leukocyte recruitment depends on nitric oxide since was dose-dependently inhibited by treatment with L-NAME (nitric oxide synthase inhibitor), and 2) the extract also inhibited the production of crucial cytokines for the leukocyte recruitment; tumor necrosis factor α and interleukin-1β. Concluding, T. sinapou ethyl acetate extract reduces oxidative stress in vitro, and infl ammatory leukocyte recruitment by a mechanism related to inhibition of cytokine production, and in a nitric oxide dependent manner in vivo.

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“…4 Outras atividades biológicas importantes, como anti-tumoral e antiviral, aparecem também descritas na literatura.…”

Section: Introductionunclassified

“…2 Estes últimos são conhecidos por apresentarem as atividades ictiotóxica 3 e larvicida. 4 Outras atividades biológicas importantes, como anti-tumoral e antiviral, aparecem também descritas na literatura. 5,6 Tephrosia toxicaria Pers., popularmente conhecida por "timbó de caiena" ou "anil", é utilizada para capturar peixes 7 e o extrato aquoso de suas raízes é aplicado como defensivo agrícola em hortas orgânicas na localidade de Guaraciaba do Norte -CE.…”

Section: Introductionunclassified

Estudo químico e biológico de Tephrosia toxicaria Pers.

Vasconcelos¹,

Lima²,

Lemos³

et al. 2009

Quím. Nova

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Recebido em 27/3/08; aceito em 23/9/08; publicado na web em 2/2/09 CHEMICAL AND BIOLOGICAL STUDY OF THE Tephrosia toxicaria Pers. The ethanol extracts from leaves, stems, pods and roots were assayed against the 3 rd instar Aedes aegypti larvae and the highest activity was observed in the roots extracts (LC 50 47.86 ppm). This extract was submitted to partition with hexane, chloroform, ethyl acetate and methanol. The respective fractions were bioassayed and the best larvicidal activities were identified in the hexane (LC 50 23.99 ppm) and chloroform (LC 50 13.80 ppm) fractions. Antioxidant activity (DDPH method) was observed in the ethanol extract (IC 50 276 µg/mL) from roots of T. toxicaria. Fractions from this extract were also tested and the highest antioxidant activity (IC 50 89 µg/mL) was found in the methanol fraction. The flavonoids iso-obovatin (1), obovatin (2), 6a,12a-dehydro-β-toxicarol (3), 6a,12a-dehydro-α-toxicarol (4) and α-toxicarol (5) were isolated and bioassayed against A. aegypti. The flavonoid 5 showed the best larvicidal activity (LC 50 24.55 ppm). The antioxidant activity of 2 was investigated and showed IC 50 3.370 µg/mL. The antioxidant and larvicidal activities of Tephrosia toxicaria are reported for the first time.Keywords: Tephrosia toxicaria; flavonoids; biological activity. iNtRoduÇÃoO gênero Tephrosia, família Leguminoseae Papilionoideae (Fabaceae), possui aproximadamente trezentas espécies, distribuídas em regiões tropicais e subtropicais.1 Espécies deste gênero apresentam capacidade biogenética para produzir substâncias com grande diversidade estrutural, tais como esteróides, aminoácidos e flavonóides, incluindo os isoflavonóides rotenóides.2 Estes últimos são conhecidos por apresentarem as atividades ictiotóxica 3 e larvicida. 4 Outras atividades biológicas importantes, como anti-tumoral e antiviral, aparecem também descritas na literatura. 5,6Tephrosia toxicaria Pers., popularmente conhecida por "timbó de caiena" ou "anil", é utilizada para capturar peixes 7 e o extrato aquoso de suas raízes é aplicado como defensivo agrícola em hortas orgânicas na localidade de Guaraciaba do Norte -CE. A literatura relata o isolamento e atividade anticâncer de compostos isolados de T. toxicaria, 8,9 bem como a composição química e atividade larvicida de seu óleo essencial. 10A busca por substitutos para os inseticidas sintéticos tem produzido muitos trabalhos científicos, contemplando inclusive a utilização de extratos ou constituintes ativos provenientes de plantas.10-15 Esta procura pode ser justificada pela fácil degradação destes constituintes, menor toxicidade ao homem e, conseqüen-temente, representa uma alternativa mais segura para o meio ambiente.15 Estas observações, aliadas à crescente incidência da febre dengue -endêmica nas Américas, 16 sendo diagnosticados de 50 a 100 milhões de casos por ano 17 -nos estimularam adicionalmente para uma prospecção química em T. toxicaria, com o objetivo de encontrar compostos sucedâneos aos larvicidas sintéticos utilizados no combate ao Aedes aegypt...

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Two unusual rotenoid derivatives, 7a-O-methyl-12a-hydroxydeguelol and spiro-13-homo-13-oxaelliptone, from the seeds of Derris trifoliata

Cited by 31 publications

References 8 publications

Tephrosia sinapouethyl acetate extract inhibits inflammatory pain in mice: Opioid receptor dependent inhibition of TNFαand IL-1βproduction

Tephrosia sinapouethyl acetate extract inhibits inflammatory pain in mice: Opioid receptor dependent inhibition of TNFαand IL-1βproduction

Tephrosia sinapou extract reduces inflammatory leukocyte recruitment in mice: effect on oxidative stress, nitric oxide and cytokine production

Estudo químico e biológico de Tephrosia toxicaria Pers.

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