Influence de la structure de composés phénoliques sur l'inhibition du Phytophthora parasitica et d'enzymes participant aux processus parasitaires.

Ravisé, André; Kirkiacharian, B. S.

doi:10.1111/j.1439-0434.1978.tb03582.x

Cited by 13 publications

(9 citation statements)

References 20 publications

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“…During the last few decades, homo-isoflavonoids have been studied for their chemical and biochemical synthesis and medicinal application. Natural and synthetic homo-isoflavonoids have been recognized to possessvarious biological properties such as anti-fungal (Ravise & Kirkiacharian, 1978;Al Nakib et al, 1990), anti-mutagenic (Wall et al, 1989), anti-inflammatory, analgesic (Darmanaden et al, 1984;Della Loggia et al, 1989), angioprotective, anti-allergic, anti-histaminic (Kirkiacharian et al, 1989) and phosphodiesterase inhibitor (Amschler et al, 1996) activities. However, no data are available on the antiviral activity of this group of flavonoids, although their structure is closely related to known anti-picornavirus compounds such as chalcone Ro 09-0410 and flavone Ro 09-0179 (De Meyer et al, 1991;Ishitsuka et al, 1982).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Picornavirus Activity of Homo-Isoflavonoids

Desideri

Olivieri

Stein

et al. 1997

Antivir Chem Chemother

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Substituted homo-isoflavonoids were synthesized in order to study their in vitro anti-picornavirus activity. The maximum non-toxic concentration of the compounds for susceptible cells (Hela) was determined, and the ability of non-cytotoxic concentrations to interfere with plaque formation by human rhinovirus (HRV) 1Band 14 and poliovirus (PV) 2 was examined. All the tested compounds were weakly effective against PV-2, while they exhibited a variable degree of activity against HRV-1 Band-14 infection. Serotype 1B was much more sensitive than 14 to the action of the compounds, and the presence of one or more chlorine atoms increased the antiviral effect in all homoisoflavonoids tested, confirming the positive influence of this substituent on activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-Picornavirus Activity of Homo-Isoflavonoids

Desideri

Olivieri

Stein

et al. 1997

Antivir Chem Chemother

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“…For compounds 1a-i & 2a-i a) R 1 = R 2 = R 3 = R 4 = H f) R 1 = OBz, R 2 = R 3 = H, R 4 = OCH 3 b) R 1 = R 2 = R 3 = H, R 4 = OCH 3 g) R 1 = R 3 = R 4 = OCH 3, R2= H c) R 1 = R 2 = H, R 3 = R 4 = OCH 3 h) R 1 = OH, R 2 = R 3 = H, R 4 = OCH 3 d) R 1 = R 2 = R 3 = H, R 4 = Cl i) R 1 = OH, R 3 = H, R 2 = R 4 = OCH 3 e) R 1 = OCH 3, R 2 = R 3 = R 4 = H…”

Section: Resultsmentioning

confidence: 99%

New efficient synthesis and bioactivity of homoisoflavonoids

Rao¹,

Damu²,

Sudhakar³

et al. 2008

Arkivoc

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Two naturally occurring homoisoflavonoids (3h,3i) and nine analogs (2a-2i) have been synthesised from appropriately substituted phenols thorough 1-(2-hydroxyphenyl)-3-phenylpropane-1-ones (1a-1i). The anti-oxidant and anti-fungal activities were determined by superoxide (NBT) and Agar cup method respectively. The reaction of 1-(2-hydroxyphenyl)-3-phenylpropane-1-ones with triethylorthoformate and 70% perchloric acid followed by aqueous hydrolysis of the intermediate perchlorates, the corresponding homoisoflavones (2a-2i) are obtained in excellent yields. Thereafter, 2a-2i has been converted into homoisoflavanones by subjecting to catalytic hydrogenation. This methodology has been applied for the first time for the synthesis of (±)-dihydrobonducellin (3h) and (±)-2 ' -methoxydihydrobonducellin (3i), which have been isolated from Caesalpinia pulcherrima.

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“…So, all these results seem to corroborate an involvement of the fungal glucosidases in apigenin formation and, during P. capsici-C. annuum interactions, jS-glucosidasic Many authors have observed a release of agiycons, irt vitro, under the action of either /J-glucosidases from the pathogen (Oku, 1959;Flood and Kirkham, 1960;Olah and Sherwood, 1973) or /J-glucosidases frotn the host (Noveroske et al, 1964). Although these agiycons often have a greater toxicity than their glucosides, Ravise and Chopin (1981) showed that, at concentrations of 7.5 x lO^'M/land 10"'M/1, luteolin and apigenin are less toxic for Phytophthora parasitica than their glycosides (luteolin 7-glucoside, iso-orientin, schaftoside). In the material in this study, at these concentrations, the inhibition of the P. capsici growth by apigenin and its glucoside apiin presented similar high differences.…”

Section: Leaf Zonementioning

confidence: 99%

“…Phenolics themselves are well-known as fungitoxic, antibacterial and antiviral. They can inhibit fungal-spore germination (Gayed and Rosa, 1975), myceliai growth (le Tourneau et al,, 1957;Ravise and Chopin, 5981;Bazzalo et al,, 1985), enzyme production (Patil and Dimond, 1968), and can also inactive the enzymes produced by pathogens (Vidhyasekaran, 1975: Ravise andChopin, 1981), and either detoxify the toxins (Sridhar and Mahadevan, 1979) or suppress their production by the pathogen (Chet et al,, 1978).…”

Section: Introductionmentioning

confidence: 99%

Behaviour of the Phenolic Compounds on Capsicum annuum Leaves Infected with Phytophthora capsici

Lizzi¹,

Roggero²,

Coulomb³

1995

Journal of Phytopathology

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In Capsicum annuum leaves, some phenolic compounds, such as chlorogenic acid and various apigenin or luteolin glycosides, can be separated by HPLC technique. During infection with Phytophthora capsici (the agent of pepper mildew), the concentrations of these compounds decreased. A fungal glucosidasic activity may be implicated, producing apigenin aglycon in the necrotic areas. Some of the phenolic compounds were only present in intercellular spaces, where their concentration increased during fungal infection, mostly in ihe resistant pepper cultivar.The Involvement of phenolics in C. annuum resistance is discussed in relation to oxidative metabolism. Zusaramenfassung Verhalten der phenolischen Verbidiingen in mit Phytophlhora capsici infizierten Capsicum aJuiuvrn-BIMernDurch die HPLC-Technik lassen sich einige in Blattem von Paprika (Capsicum annuum) enthaltene phenohsche Verhindungen trennen, wie Chlorogensaure und verschiedene Apigenin-bzw. LuteolingWkoside, Wahrend der Infektion mit Phytophthora capsici (dem Erreger des PapHkamehltaus) gingen die Konzentrationen dieser Verbindungen zurUck. Eine Glukosidaseaktivitat des Pilzes konnte zur Bildung von Apigenin-Aglykon in den nekrotischen Flachen fuhren, Einige der phenolischen Verbindungen kamen nur in den Interzellularraumen vor, wo ihre Konzentration vor allem hei der resistenten Paprikasorte wahrend der Pilzinfektion zunahm.Die Beteiligung phenolischer Verbindungen an der Resistenz von C. annuum wird unter Bezug auf den oxidativen Metabolismus diskutiert.

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Influence de la structure de composés phénoliques sur l'inhibition du Phytophthora parasitica et d'enzymes participant aux processus parasitaires.

Cited by 13 publications

References 20 publications

Synthesis and Anti-Picornavirus Activity of Homo-Isoflavonoids

Synthesis and Anti-Picornavirus Activity of Homo-Isoflavonoids

New efficient synthesis and bioactivity of homoisoflavonoids

Behaviour of the Phenolic Compounds on Capsicum annuum Leaves Infected with Phytophthora capsici

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