The structure and synthesis of (+)-obliquin

Dean, F. M.; Parton, Brian

doi:10.1039/j39690000526

Cited by 9 publications

(4 citation statements)

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“…Class II contained a known compound, dihydroobliquin, but we only found from the literature that it is an artificially hydrogenated obliquin derivative (Dean and Parton 1969). Obliquin was isolated as a phenylated coumarin from a timber tree, Ptaeroxylon obliquum Taylor 1966, Koorbanally et al 2002), but we could not find any reports about its biological activity or that of dihydro-obliquin.…”

Section: Mode Of Action Of Ss Compoundsmentioning

confidence: 86%

Chemical Genetic Screening Identifies a Novel Inhibitor of Parallel Alignment of Cortical Microtubules and Cellulose Microfibrils

Yoneda

Higaki

Kutsuna

et al. 2007

Plant and Cell Physiology

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It is a well-known hypothesis that cortical microtubules control the direction of cellulose microfibril deposition, and that the parallel cellulose microfibrils determine anisotropic cell expansion and plant cell morphogenesis. However, the molecular mechanism by which cortical microtubules regulate the orientation of cellulose microfibrils is still unclear. To investigate this mechanism, chemical genetic screening was performed. From this screening, 'SS compounds' were identified that induced a spherical swelling phenotype in tobacco BY-2 cells. The SS compounds could be categorized into three classes: those that disrupted the cortical microtubules; those that reduced cellulose microfibril content; and thirdly those that had neither of these effects. In the last class, a chemical designated 'cobtorin' was found to induce the spherical swelling phenotype at the lowest concentration, suggesting strong binding activity to the putative target. Examining cellulose microfibril regeneration using taxol-treated protoplasts revealed that the cobtorin compound perturbed the parallel alignment of pre-existing cortical microtubules and nascent cellulose microfibrils. Thus, cobtorin could be a novel inhibitor and an attractive tool for further investigation of the mechanism that enables cortical microtubules to guide the parallel deposition of cellulose microfibrils.

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Section: Mode Of Action Of Ss Compoundsmentioning

confidence: 86%

Chemical Genetic Screening Identifies a Novel Inhibitor of Parallel Alignment of Cortical Microtubules and Cellulose Microfibrils

Yoneda

Higaki

Kutsuna

et al. 2007

Plant and Cell Physiology

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“…The spectrum of 7hydroxy-6-methoxycoumarin shows two singlets for protons at positions 5 and 8 at 6.8 and 7.25 ppm, respectively, whereas the same two protons in 6-hydroxy-7-methoxycoumarin overlap and appear as a two-proton singlet at 7.03 ppm. The UV spectra of the two isomers are also different, particularly in alkaline solvents (1,9,10). The isomers give identical UV spectra in neutral solvents (Fig.…”

Section: Downloaded Frommentioning

confidence: 96%

Novel Biotransformations of 7-Ethoxycoumarin by Streptomyces griseus

Sariaslani

Rosazza

1983

Appl Environ Microbiol

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Biotransformation of 7-ethoxycoumarin by Streptomyces griseus resulted in the accumulation of two metabolites which were isolated and identified as 7hydroxycoumarin and 7-hydroxy-6-methoxycoumarin. A novel series of biotransformation reactions is implicated in the conversion of the ethoxycoumarin substrate to these products, including 0-deethylation, 6-hydroxylation to form a 6,7-dihydroxycoumarin catechol, and subsequent 0-methylation. Either 7-hydroxycoumarin or 6,7-dihydroxycoumarin was biotransformed to 7-hydroxy-6methoxycoumarin by S. griseus. Trace amounts of the isomeric 6-hydroxy-7methoxycoumarin were detected when 6,7-dihydroxycoumarin was used as the substrate. Efforts to obtain a cell-free catechol-O-methyltransferase enzyme system from S. griseus were unsuccessful. However, [methyl-14C]methionine was used with cultures of S. griseus to form 7-hydroxy-6-[14C]methoxycoumarin. Streptomyces griseus (UT 1158, NRRL 8090) catalyzes a wide array of oxidative biotransformation reactions with simple aromatic compounds (23), alkaloids (7, 8, 16, 17, 20, 21), and terpene substrates (5). Reactions common for S. griseus include 0-and N-dealkylations, aromatic hydroxylation, epoxidation, and carbon-car

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“…L'extrait CthCropitrolique contient des carbures et alcools aliphatiques, dont l'ttude n'a pas Ctt poursuivie, des terpenes et stCrols en quantitC notable, et de petites quantitts de coumarines; la plus grande partie de cellesci est extraite par le benztne. La chromatographie sur colonne de silice de l'extrait tthtropttrolique pernlet d'isoler et de characttriser, par examen de leurs constantes et donntes spectrales (F, UV, IR, RMN, SIM), un triterpine pentacyclique, le luptol 1 (teneur: 0,3 glkg) [ [ 2 ] ; la position 7 portant un oxygkne, comme l'indique le spectre UV, la chaPne dimCthylallyle est donc fix6 en 8.…”

Section: Leurs Structures Sont Celles De La (3'3'-dimethyl-2'3'-epounclassified

PRODUITS NEUTRES DEMYRTOPSIS SELLINGII:ISOLEMENT DE DEUX NOUVELLES COUMARINES, LA MYRSELLINE ET LE MYRSELLINOL¹

Ms¹,

Vaquette²,

Jl³

et al. 1977

Planta Med

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A triterpene, lupeol, a sterol, sitosterol and four coumarins, bergapten, phellopterin, myrsellin and myrsellinol have been isolated from M y r t o p s i s s e 11 i n g i i ; myrsellin and myrsellinol are new; their structures have been established as (3',3'-dimeth y1-2',3'-epoxy-buty1oxy)-7-(3",3"-dimethy1a11y1)-8-coumarin for myrsellin, and (3',3'-dimethyl-2'3'-dihydroxy-butyloxy)-7-(3",3"-dimethyl-ally1)-8-coumarin for myrsellinol. Un triterptne, le lupe'ol, un ste'rol, le P-sitosterol, et quatre coumarines, le bergaptkne, la phelloptkrine, la myrselline et le myrsellinol, ont e'te' isole's des tiges feuille'es de M y r t o p s i s sell i n g i i ; la myrselline et le myrsellinol sont nouveazrx;

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The structure and synthesis of (+)-obliquin

Cited by 9 publications

References 0 publications

Chemical Genetic Screening Identifies a Novel Inhibitor of Parallel Alignment of Cortical Microtubules and Cellulose Microfibrils

Chemical Genetic Screening Identifies a Novel Inhibitor of Parallel Alignment of Cortical Microtubules and Cellulose Microfibrils

Novel Biotransformations of 7-Ethoxycoumarin by Streptomyces griseus

PRODUITS NEUTRES DEMYRTOPSIS SELLINGII:ISOLEMENT DE DEUX NOUVELLES COUMARINES, LA MYRSELLINE ET LE MYRSELLINOL¹

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The structure and synthesis of (+)-obliquin

Cited by 9 publications

References 0 publications

Chemical Genetic Screening Identifies a Novel Inhibitor of Parallel Alignment of Cortical Microtubules and Cellulose Microfibrils

Chemical Genetic Screening Identifies a Novel Inhibitor of Parallel Alignment of Cortical Microtubules and Cellulose Microfibrils

Novel Biotransformations of 7-Ethoxycoumarin by Streptomyces griseus

PRODUITS NEUTRES DEMYRTOPSIS SELLINGII:ISOLEMENT DE DEUX NOUVELLES COUMARINES, LA MYRSELLINE ET LE MYRSELLINOL1

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PRODUITS NEUTRES DEMYRTOPSIS SELLINGII:ISOLEMENT DE DEUX NOUVELLES COUMARINES, LA MYRSELLINE ET LE MYRSELLINOL¹