Antifungal activity toPhytophthora infestans of sesquiterpenoids from infected potato tubers

Engström, Karin; Widmark, Anna-Karin; Brishammar, Sture; Helmersson, Seved

doi:10.1007/bf02358390

Cited by 21 publications

(16 citation statements)

References 24 publications

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“…The elicitor was prepared according to Ayers et al (22) using fungal mycelia provided by Dr. Curtis. To increase the chances of isolating the full range of elicitorinducible mRNAs, cells were collected at several time points (4,6, and 8 h) and combined prior to RNA isolation.…”

Section: Methodsmentioning

confidence: 99%

“…First, members of this family of compounds are known to inhibit mycelial growth of Phytophthora infestans (6) and Rhizoctonia solani (7), spore germination of Fusarium oxysporum (8), and the growth of the bacteria Staphylococcus aureus and Bacillus subtilis (9). Second, the induced biosynthesis of these phytoalexins coincides with a metabolic switch at a key branch point in the isoprenoid biosynthetic pathway.…”

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confidence: 99%

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Functional Characterization of Premnaspirodiene Oxygenase, a Cytochrome P450 Catalyzing Regio- and Stereo-specific Hydroxylations of Diverse Sesquiterpene Substrates

Takahashi

Yeo

Zhao

et al. 2007

Journal of Biological Chemistry

106

105

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Solavetivone, a potent antifungal phytoalexin, is derived from a vetispirane-type sesquiterpene, premnaspirodiene, by a putative regio-and stereo-specific hydroxylation, followed by a second oxidation to yield the ␣,␤-unsaturated ketone. Mechanistically, these reactions could occur via a single, multifunctional cytochrome P450 or some combination of cytochrome P450s and a dehydrogenase. We report here the characterization of a single cytochrome P450 enzyme, Hyoscyamus muticus premnaspirodiene oxygenase (HPO), that catalyzes these successive reactions at carbon 2 (C-2) of the spirane substrate. HPO also catalyzes the equivalent regio-specific (C-2) hydroxylation of several eremophilane-type (decalin ring system) sesquiterpenes, such as with 5-epi-aristolochene. Moreover, HPO displays interesting comparisons to other sesquiterpene hydroxylases. 5-Epi-aristolochene di-hydroxylase (EAH) differs catalytically from HPO by introducing hydroxyl groups first at C-1, then C-3 of 5-epi-aristolochene. HPO and EAH also differ from one another by 91-amino acid differences, with four of these differences mapping to putative substrate recognition regions 5 and 6. These four positions were mutagenized alone and in various combinations in both HPO and EAH and the mutant enzymes were characterized for changes in substrate selectivity, reaction product specificity, and kinetic properties. These mutations did not alter the regio-or stereo-specificity of either HPO or EAH, but specific combinations of the mutations did improve the catalytic efficiencies 10 -15-fold. Molecular models and comparisons between HPO and EAH provide insights into the catalytic properties of these enzymes of specialized metabolism in plants.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Functional Characterization of Premnaspirodiene Oxygenase, a Cytochrome P450 Catalyzing Regio- and Stereo-specific Hydroxylations of Diverse Sesquiterpene Substrates

Takahashi

Yeo

Zhao

et al. 2007

Journal of Biological Chemistry

106

105

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“…This causes less cholesterol absorption in the body. Ethanolic extract also revealed an antimicrobial compound called Solavetivone (Table 5), a sesquiterpene phytoalexins members of this family of compounds are known to inhibit mycelial growth of Phytophthora infestans (Engstrom et al, 1999) and Rhizoctonia solani (Yao et al, 2003), spore germination of Fusarium oxysporum (Yokose et al, 2004), and the growth of the bacteria Staphylococcus aureus and Bacillus subtilis (Kuroyanagi et al, 1998). Finally, the decoction identified a large variety of compounds which are biologically important stating with antioxidants such as: butylated hydroxytoluene (BHT) , vitamin E and linoleic acid (Table 8); however, experiments on linoleic acid subjected to 2,2′-azobis (2-amidinopropane) dihydrochloride-induced oxidation with different combinations of phenolics show that binary mixtures can lead to either a synergetic antioxidant effect or to an antagonistic effect (Peyrat-Maillard et al, 2003).…”

Section: Resultsmentioning

confidence: 99%

Phytochemical screening chemical composition and toxicity of Euphorbia regis-jubae (Webb Berth)

Hmimid¹,

Lahlou²,

Loutfi³

et al. 2012

J. Toxicol. Environ. Health Sci.

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, an endemic Moroccan medicinal herb, and also, widely used as food for camels and goats was subjected to a phytochemical screening of increasing polarity gradient (petroleum ether, iso-hexan, chloroform, ethanol, methanol, and distilled water). Furthermore, the chemical compositions of different solvent extracts were subjected to gas chromatography-mass spectrometry (GC-MS) analysis and the aqueous extract was purchased to an acute and chronic toxicity using Wistar rats. The acute and chronic toxicity study showed no toxicity when up to 5 g/kg body weight is administered orally. Preliminary phytochemical analysis of E. regis-jubae (Webb & Berth) revealed the presence of phenol, tannin, steroids, flavonoids, alkaloids, and terpenoids. Further, the GC-MS analysis revealed some compounds which are biologically important.

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“…Sci. 67 (2010) 504 the whole extract, has been reported to possess fungicidal and fungistatic properties (Aleu et al, 2001;Engstrom et al, 1999) and is therefore believed to be responsible in great part to the cypress natural durability. Other components like bornyl acetate, α-cedrene or β-cedrene have been reported to be present in the composition of essential oils and possessing antimicrobial or antifungal properties (Jasicka-Misiaka et al, 2004;Jeong et al, 2007;Kordali et al, 2008;Kuźma et al, 2009;Rançić, et al, 2005).…”

Section: Gc-ms Analysismentioning

confidence: 99%

Effect of extractives on conferred and natural durability of Cupressus lusitanica heartwood

Mohareb

Sirmah

Desharnais³

et al. 2010

Ann. For. Sci.

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Abstract• Identification of extractives present in Cupressus lusitanica heartwood has been conducted using GC-MS analyses. The chromatogram of toluene/ethanol extracts indicated the presence of large amounts of benzaldehyde and numerous terpenic compounds such as cedrol, agathadiol, epimanool, bornyl acetate, α-cedrene and β-cedrene.• The effect of these extractives on the natural durability of cypress wood was investigated on heart wood blocks exposed to pure culture of Poria placenta before or after solvent extraction. Weight losses revealed severe fungal degradations on the extracted blocks compared to unextracted ones.• Efficiency of heartwood extractives as inhibitors of the growth of Poria placenta on malt/agar test confirms their contribution to cypress natural durability.• Cypress blocks were treated at 240 • C for different times to reach different levels of thermodegradation to evaluate effect of heat treatment on fungal durability. Results indicate that evaporation of volatile extractives during the first few minutes of heat treatment contribute to decreased wood durability, while longer treatment times lead to the expected improvement of durability.• This study suggests that the content of extractives, which may be modified during wood drying or weathering processes, could be the origin of the conflicting data described in the literature concerning cypress natural durability. Mots-clés :Cupressus lusitanica / durabilité / extractibles / traitement thermique / pourriture Résumé -Effet des extractibles sur la durabilité naturelle du duramen de cyprès.• Les extractibles présents dans le duramen de Cupressus lusitanica ont été analysés par GC-MS. Le chromatogramme des extraits obtenus à l'aide d'un mélange toluène/éthanol met en évidence des quantités importantes de benzaldéhyde et de nombreux composés terpéniques comme le cédrol, l'agathadiol, l'épimanool, l'acétate de bornyl, l'α-cédrène et le β-cédrène.• L'effet des extractibles sur la durabilité naturelle du cyprès a été évalué à l'aide d'essais réalisés sur des blocs préalablement extraits ou non puis exposés à Poria placenta. Les pertes de masse mettent en évidence une dégradation importante des échantillons extraits comparativement aux témoins non extraits.• L'efficacité des extractibles comme inhibiteur de croissance de Poria placenta a été évaluée. Les résultats indiquent une forte inhibition du développement fongique.• Des blocs de cyprès ont été traités à 240 • C pendant des temps variables pour atteindre différents niveaux de thermo-dégradation. L'évaporation des extractibles volatils durant la première phase du traitement thermique conduit à une diminution de la durabilité du bois aux agents de pourriture, alors que des traitements plus longs conduisent à l'augmentation de durabilité attendue.• Cette étude suggère que la teneur en extractibles, susceptible de varier suite au séchage ou aux intempéries, peut être à l'origine des observations contradictoires rapportées dans la littérature concernant la durabilité naturelle du cyprès.

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Antifungal activity toPhytophthora infestans of sesquiterpenoids from infected potato tubers

Cited by 21 publications

References 24 publications

Functional Characterization of Premnaspirodiene Oxygenase, a Cytochrome P450 Catalyzing Regio- and Stereo-specific Hydroxylations of Diverse Sesquiterpene Substrates

Functional Characterization of Premnaspirodiene Oxygenase, a Cytochrome P450 Catalyzing Regio- and Stereo-specific Hydroxylations of Diverse Sesquiterpene Substrates

Phytochemical screening chemical composition and toxicity of Euphorbia regis-jubae (Webb Berth)

Effect of extractives on conferred and natural durability of Cupressus lusitanica heartwood

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