Studies on the Interaction of Surangin B with Insect Mitochondria, Insect Synaptosomes, and Rat Cortical Neurones in Primary Culture

Zheng, Jian; Leong, Dennis; Lees, George; Nicholson, Russell A.

doi:10.1006/pest.1998.2349

Cited by 11 publications

(11 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The coumarin surangin B acts as an inhibitor of mitochondrial electron transport, probably, targeting the cytochrome c oxidoreductase (complex III) and cytochrome b. This mechanism is similar to the beta-methoxyacrylates, which bind to the cytochrome bc 1 complex, at a site distinct from antimycin, the classical blocker of electron flow between cytochrome b and c (Zheng et al, 1998). In addition, coumarin and mainly furanocoumarins can also alter the detoxication capability of an organism, by reversibly or irreversibly inhibiting cytochrome P450 detoxication enzymes (Letteron et al, 1986;Neal & Wu, 1994).…”

Section: Resultsmentioning

confidence: 99%

“…The surangin B has the potential to release the neurotransmitter centrally in insects (Nicholson & Zhang, 1995). The enhanced release of the neurotransmitter from insect synaptosomes, and the substantial increase in miniature excitatory postsynaptic currents (EPSC) frequency, which precedes a loss of neural activity, are the result of intraterminal mitochondria failing to buffer Ca 2+ effectively, and maintain ATP (Zheng et al, 1998). Zheng et al (1998) showed that surangin B has the potential to cause substantial functional disturbances in both muscle mitochondria and nervous system mitochondria in vitro.…”

Section: Resultsmentioning

confidence: 99%

“…The enhanced release of the neurotransmitter from insect synaptosomes, and the substantial increase in miniature excitatory postsynaptic currents (EPSC) frequency, which precedes a loss of neural activity, are the result of intraterminal mitochondria failing to buffer Ca 2+ effectively, and maintain ATP (Zheng et al, 1998). Zheng et al (1998) showed that surangin B has the potential to cause substantial functional disturbances in both muscle mitochondria and nervous system mitochondria in vitro. The state 3 of respiration was blocked by surangin B, in cricket Acheta domesticus (Linnaeus) (Orthoptera: Gryllidae) and blowfly Phaenicia sericata (Meigen) (Diptera: Calliphoridae) flight muscle mitochondria.…”

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Plant compounds insecticide activity against Coleoptera pests of stored products

Moreira

Picanço

Barbosa³

et al. 2007

Pesq. agropec. bras.

View full text Add to dashboard Cite

-The objective of this work was to screen plants with insecticide activity, in order to isolate, identify and assess the bioactivity of insecticide compounds present in these plants, against Coleoptera pests of stored products: Oryzaephilus surinamensis L. (Silvanidae), Rhyzopertha dominica F. (Bostrichidae) and Sitophilus zeamais Mots. (Curculionidae). The plant species used were: basil (Ocimum selloi Benth.), rue (Ruta graveolens L.), lion's ear (Leonotis nepetifolia (L.) R.Br.), jimson weed (Datura stramonium L.), baleeira herb (Cordia verbenacea L.), mint (Mentha piperita L.), wild balsam apple (Mormodica charantia L.), and billy goat weed or mentrasto (Ageratum conyzoides L.). The insecticide activity of hexane and ethanol extracts from those plants on R. dominica was evaluated. Among them, only hexane extract of A. conyzoides showed insecticide activity; the hexane extract of this species was successively fractionated by silica gel column chromatography, for isolation and purification of the active compounds. Compounds 5,6,7,8,3',4', 5,6,7,8,3'-pentamethoxy-4',5'-methilenedioxyflavone and coumarin were identified. However, only coumarin showed insecticide activity against three insect pests (LD 50 from 2.72 to 39.71 mg g -1 a.i.). The increasing order of insects susceptibility to coumarin was R. dominica, S. zeamais and O. surinamensis.Index terms: natural insecticide, pest management, alternative control, secondary metabolites. Compostos de plantas com atividade inseticida a coleópteros-praga de produtos armazenadosResumo -O objetivo deste trabalho foi selecionar plantas com atividade inseticida, para isolar, identificar e avaliar a bioatividade de compostos inseticidas presentes nessas plantas, contra as seguintes pragas de produtos armazenados da ordem Coleoptera: Sitophilus zeamais Mots. (Curculionidae), Rhyzopertha dominica F. (Bostrichidae) e Oryzaephilus surinamensis L. (Silvanidae). As espécies de plantas usadas foram: anis (Ocimum selloi Benth), arruda (Ruta graveolens L.), cordão-de-frade (Leonotis nepetifolia L.), datura (Datura stramonium L.), erva baleeira (Cordia verbenacea L.), hortelã (Mentha piperita L.), melão-de-são-caetano (Mormodica charantia L.) e mentrasto (Ageratum conyzoides L.). Avaliou-se a toxicidade dos extratos hexânico e etanólico dessas plantas sobre R. dominica. Somente o extrato hexânico de A. conyzoides apresentou atividade inseticida. O extrato hexânico desta planta foi fracionado, sucessivamente, por cromatografia de coluna de sílica gel, para isolamento e purificação dos compostos ativos. Os compostos 5,6,7,8,3',4', 5,6,7,8,5'-metilenodioxiflavona e cumarina foram identificados. Entretanto, somente a cumarina apresentou atividade inseticida às três espécies de insetos (DL 50 de 2,72 a 39,71 mg g -1 de i.a.). A ordem crescente de suscetibilidade à cumarina foi R. dominica, S. zeamais e O. surinamensis.Termos para indexação: inseticida natural, manejo de pragas, controle alternativo, metabolito secundário.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Plant compounds insecticide activity against Coleoptera pests of stored products

Moreira

Picanço

Barbosa³

et al. 2007

Pesq. agropec. bras.

View full text Add to dashboard Cite

show abstract

“…Although information is still scanty on the mode of action of osthol against insects, in rats, it is reported to interfere with the binding of thyrotropin releasing hormone to its receptor, and thus alters receptor‐evoked intracellular signals (Ojala, 2001). Many coumarins caused insect immobilization by inhibition of mitochondria electron transport and neurotoxic action (Nicholson & Zhang, 1995; Zhen et al ., 1998), while some others caused a reversible or irreversible inhibition of cytochrome P450 activity in Manduca friday (L.) (Lepidoptera: Sphingidae) (Neal & Wu, 1994).…”

Section: Discussionmentioning

confidence: 99%

Identification, isolation and characterization of the antifeedant constituent of Clausena anisata against Helicoverpa armigera (Lepidoptera: Noctuidae)

et al. 2009

View full text Add to dashboard Cite

Hexane, petroleum ether, chloroform, ethyl acetate, methanol and water extracts of Clausena anisata [(Willd.) Hook F. Ex Benth] leaves and roots were evaluated against Helicoverpa armigera (Hübner) for antifeedant activities. Antifeedant activity was confirmed, and was found to be higher in root extracts than those of the leaf. Chloroform and petroleum ether extracts of the root showed strongest antifeedant activities (DC 50 s [concentration (C) causing 50% deterrence compared with the control] 0.014% and 0.016% respectively), and root extracts were fractionated using silica gel column chromatography. One fraction of the chloroform and one of the petroleum ether root extracts was active; and on the basis of mass spectroscopy and 1 H and 13 C nuclear magnetic resonance spectral data, the active compounds in the two fractions were confirmed to be identical, and identified as osthol [2H-1-Benzopyran-2-one, 7-methoxy-8-(3-methyl-2-butenyl)]. The highest concentration of osthol was found in the chloroform root extract. Antifeedant activities of the root extracts, as measured by DC 50 values, were highly correlated with their osthol contents. Approximately 99% of the variation in bioactivity of the root extracts could be accounted for by variation in osthol content; osthol therefore, appeared to be an antifeedant component of C. anisata to H. armigera. This may provide a new approach to managing this pest.

show abstract

“…A rise in cytosolic free [Ca 2+ ] is a critical event associated with neurotransmitter vesicle depletion, and resin acids appear to initiate this through intraterminal discharge of Ca 2+ , although significant dependence on extracellular Ca 2+ was also observed ( Zheng & Nicholson, 1998 ). The three resin acids we have studied to date include abietic acid, dehydroabietic acid (see Morales et al ., 1992 for structures), and 12,14‐Cl 2 DHA (see Figure 1 for structure), and of these, 12,14‐Cl 2 DHA is the most potent, increasing cytosolic free [Ca 2+ ] and stimulating transmitter release in the low micromolar range ( Zheng & Nicholson, 1996 ; 1998 ).…”

Section: Introductionmentioning

confidence: 99%

Inhibition of GABA‐gated chloride channels by 12,14‐dichlorodehydroabietic acid in mammalian brain

Nicholson¹,

Lees²,

Zheng³

et al. 1999

British J Pharmacology

Self Cite

View full text Add to dashboard Cite

12,14‐dichlorodehydroabietic acid (12,14‐Cl2DHA) reduced GABA‐stimulated uptake of 36Cl− into mouse brain synaptoneurosomes suggesting inhibition of mammalian GABAA receptor function. 12,14‐Cl2DHA did not affect the binding of [3H]‐muscimol to brain membranes but displaced specifically bound [3H]‐EBOB. The inhibitory effect on [3H]‐EBOB binding was not reversible. 12,14‐Cl2DHA reduced the availability of [3H]‐EBOB binding sites (Bmax) without changing the KD of the radioligand for remaining sites. 12,14‐Cl2DHA did not affect the rate of association of [3H]‐EBOB with its chloride channel receptor, but increased the initial rate of [3H]‐EBOB dissociation. 12,14‐Cl2DHA enhanced the incidence of EPSCs when rapidly applied to cultured rat cortical neurones. Longer exposures produced block of IPSCs with marked increases in the frequency of EPSCs and min EPSCs. 12,14‐Cl2DHA also irreversibly suppressed chloride currents evoked by pulses of exogenous GABA in these cells. Ultimately, 12,14‐Cl2DHA inhibited all synaptic traffic and action currents in current clamped cells indicating that, in contrast to picrotoxinin (which causes paroxysmal bursting), it is not fully selective for the GABAA receptor‐chloride channel complex. The depolarizing block seen with 12,14‐Cl2DHA in amphotericin‐perforated preparations implicates loss of Ca2+ buffering in the polarity change and this may account for inhibition of spontaneous action potentials. Our investigation demonstrates that 12,14‐Cl2DHA blocks GABA‐dependent chloride entry in mammalian brain and operates as a non‐competitive insurmountable GABAA antagonist. The mechanism likely involves either irreversible binding of 12,14‐Cl2DHA to the trioxabicyclooctane recognition site or a site that is allosterically coupled to it. We cannot exclude, however, the possibility that 12,14‐Cl2DHA causes localized proteolysis or more extensive conformational change within a critical subunit of the chloride channel. British Journal of Pharmacology (1999) 126, 1123–1132; doi:

show abstract

Studies on the Interaction of Surangin B with Insect Mitochondria, Insect Synaptosomes, and Rat Cortical Neurones in Primary Culture

Cited by 11 publications

References 27 publications

Plant compounds insecticide activity against Coleoptera pests of stored products

Plant compounds insecticide activity against Coleoptera pests of stored products

Identification, isolation and characterization of the antifeedant constituent of Clausena anisata against Helicoverpa armigera (Lepidoptera: Noctuidae)

Inhibition of GABA‐gated chloride channels by 12,14‐dichlorodehydroabietic acid in mammalian brain

Contact Info

Product

Resources

About