Comparison of the fungicidal activities of (E)-4-hydroxylated stilbenes and related bibenzyls

Schultz, Tor P.; Cheng, Qiang; Boldin, W.D.; Hubbard, Tom F.; Jin, Li; Fisher, Thomas H.; Nicholas, Darrel D.

doi:10.1016/s0031-9422(00)98228-1

Cited by 32 publications

(22 citation statements)

References 22 publications

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“…Stilbenes have been suggested to be inactive against white-rot fungi (Hart 1981;Lyr 1961). However, we previously found (Schultz et al 1992) 3-stilbenols to be moderately active against T. versicolor while 4-stilbenols had little or no activity at 300ppm (Schultz et al 1990(Schultz et al , 1991(Schultz et al , 1992. All other stilbenes examined in this study (all 4-stilbenols) had T. versicolor IC 50 values above 400ppm (low activity).…”

Section: Bioactivitiescontrasting

confidence: 45%

“…Based on our prior QSAR studies (Schultz et al 1991), a low IC 50 activity of about 300 ppm was anticipated, which is approximately the activity found (197 ppm). Several assumptions were made, however, when using our prior studies to predict resveratrols's low activity against G. trabeum.…”

Section: Bioactivitiesmentioning

confidence: 72%

“…Several assumptions were made, however, when using our prior studies to predict resveratrols's low activity against G. trabeum. These assumptions are: 1) that 5' substituents will act in a similar manner as 3' substituents, because previously only the 3' and/or 4' positions were examined (Schultz et al 1990(Schultz et al , 1991; and 2) our prior QSAR hydrophobic relationship could be extrapolated to a more hydrophylic stilbene. ' f We had previously found that the substitution pattern of the "A" ring in the 3, 4 and 5 positions did not affect brown-rot activity (Schultz et al 1992).…”

Section: Bioactivitiesmentioning

confidence: 99%

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Durability of Angiosperm Heartwood: The Importance of Extractives

Schultz¹,

Harms²,

Fisher³

et al. 1995

HFSG

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Section: Bioactivitiescontrasting

confidence: 45%

Section: Bioactivitiesmentioning

confidence: 72%

Section: Bioactivitiesmentioning

confidence: 99%

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Durability of Angiosperm Heartwood: The Importance of Extractives

Schultz¹,

Harms²,

Fisher³

et al. 1995

HFSG

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“…These groups may serve as essential, regulating, or enhancing moieties in such compounds (8, 10–13). For example, a 4′-hydroxy group was demonstrated to be essential for the cytogenetic and estrogenic activities of stilbenoids (1, 11).…”

Section: Introductionmentioning

confidence: 99%

Biological Activity of Peanut (Arachis hypogaea) Phytoalexins and Selected Natural and Synthetic Stilbenoids

Соболев

Khan

Tabanca

et al. 2011

J. Agric. Food Chem.

102

110

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The peanut plant (Arachis hypogaea L.), when infected by a microbial pathogen, is capable of producing stilbene-derived compounds that are considered antifungal phytoalexins. In addition, the potential health benefits of other stilbenoids from peanuts, including resveratrol and pterostilbene, have been acknowledged by several investigators. Despite considerable progress in peanut research, relatively little is known about the biological activity of the stilbenoid phytoalexins. This study investigated the activities of some of these compounds in a broad spectrum of biological assays. Since peanut stilbenoids appear to play roles in plant defense mechanisms, they were evaluated for their effects on economically important plant pathogenic fungi of the genera Colletotrichum, Botrytis, Fusarium, and Phomopsis. We further investigated these peanut phytoalexins, together with some related natural and synthetic stilbenoids (a total of 24 compounds) in a panel of bioassays to determine their anti-inflammatory, cytotoxic, and antioxidant activities in mammalian cells. Several of these compounds were also evaluated as mammalian opioid receptor competitive antagonists. Assays for adult mosquito and larvae toxicity were also performed. The results of these studies reveal that peanut stilbenoids, as well as related natural and synthetic stilbene derivatives, display a diverse range of biological activities.

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“…These signals were correlated with the 13 C chemical shifts at δ C 32.95-33.98, respectively, in the 1 H-13 C HETCOR spectrum. In the NMR spectra of (E)-4-bis-(stilbenylthio)alkanes (7)(8)(9)(10)(11), the triplet at δ 2.98-3.21 ppm corresponding to the S-CH 2 protons integrating for 4 protons fully supported the respective structures. These signals showed coupling to carbons at δ 32.20-32.44 ppm.…”

Section: Resultsmentioning

confidence: 79%