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Chemical Structure| 156713-10-9

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Enrico M. Cabutaje ; Kotomi Ueno ; Kumiko Osaki-Oka ; Kazutaka Kido ; Thomas Edison E. dela Cruz ; Atsushi Ishihara

Abstract: The excessive use of chemical pesticides in agricultural fields for controlling plant pathogenic microorganisms harms human health, the environment, and other beneficial microorganisms in the soil and plants. To address this challenge, it is essential to isolate and discover bioactive compounds from biological resources that could inhibit plant pathogenic microorganisms. In this study, the culture filtrate of the edible mushroom Pleurotus ostreatus was subjected to bioassay-guided isolation, and two phthalide derivatives—4,6-dimethoxyphthalide (1) and 5,7-dimethoxyphthalide (2)—were identified, along with an oxindole compound—3-hydroxy-3-methyloxindole (3). The inhibitory activities of the three compounds were evaluated against four fungal and five bacterial pathogens. Remarkably, 1 and 2 exhibited the lowest IC50 values against the conidial germination and germ tube elongation of the rice blast fungus Pyricularia oryzae. However, their effectiveness against bacterial pathogens was relatively low. The (S) and (R)-enantiomers of 3-hydroxy-3-methyloxindole showed different activities against plant fungal pathogens and bacterial plant pathogens.

Keywords: edible mushroom ; oxindole ; phthalide ; Pleurotus ostreatus ; plant pathogenic microorganism

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Coady, Zeke ; Smith, Jordan N. ; Wilson, Katie A. ; White, Nicholas G. ;

Abstract: Two macrocycles were synthesized through cyclization reactions of 1-(2,5-diethoxyphenyl)ethan-1-ol and 1-(2,5-dimethoxyphenyl)ethan-1-ol giving pillar [6]arenes with a Me substituent at each belt position. These macrocycles form stereospecifically with the only observed isomer being the rtctct isomer with alternating up and down orientations of the belt Me groups. Isolated yields were modest (7 and 9%) but the macrocycles are prepared in a single step from either a com.-available alc. or very readily-prepared precursor. X-ray crystal structures of the macrocycles indicate they have a capsule-like structure, which is far from the conventional pillar shape. D. functional theory calculations reveal that the energy barrier required to obtain the pillar conformation is significantly higher for these belt-functionalized macrocycles than for the conventional belt-unfunctionalized pillar[6]arenes.

Keywords: pillararenes ; supramolecular chemistry ; synthesis ; macrocycles

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Product Details of [ 156713-10-9 ]

CAS No. :156713-10-9
Formula : C10H14O3
M.W : 182.22
SMILES Code : C[C@@H](C1=CC(OC)=CC=C1OC)O
MDL No. :MFCD09863681

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