Characterization of plant coumarins by combined gas chromatography, ultraviolet absorption spectroscopy, and nuclear magnetic resonance analysis

Steck, Warren; Bailey, B. K.

doi:10.1139/v69-591

Cited by 44 publications

(25 citation statements)

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“…Psoralen compounds such as xanthotoxin have been found in an array of plants (17,19,22,23) including the family Leguminosae (to date, these compounds have not been isolated from peas) (1 2The term "inducer" in this paper will refer to an agent which can cause an increase in extractable PAL and pisatin.…”

Section: Methodsmentioning

confidence: 99%

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Hadwiger

1972

Plant Physiol.

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Section: Methodsmentioning

confidence: 99%

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Hadwiger

1972

Plant Physiol.

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“…In their n.m.r. spectra doublets could be discerned at 6 6.2,7.7,6.9, and 7.4, indicating they were 8-alkyl coumarins (5). Both showed 7-methoxyl at 6 3.9 but the aliphatic end of the spectrum was obscured by instrument noise: in one derivative signals (3H?)…”

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confidence: 99%

“…and n.m.r. spectroscopy (5) and by co-chromatography with an authentic standard, and two other 8-isopentenyl-type derivatives present only in trace amounts were partly characterized. These, isolated by gas chromatography, had the same fluorescence and U.V.…”

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confidence: 99%

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Paniculatin, a New Coumarin from Murraya paniculata (L.) Jack

Steck¹

1972

Can. J. Chem.

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The coumarin derivatives osthol and coumurrayin were isolated from foliage of Murrayapaniculata (Rutaceae). In addition, a new coumarin, paniculatin, was obtained. By means of chemical degradation and u.v., n.m.r., and mass spectroscopy, the new compound was identified as 7-methoxy-8-(isovaleryloxy-2-keto-3-methylbutyl)coumarin.L'osthol et la coumurrayine des derivb de la coumarine, ont ete iso1i.s i partir du Murrayapaniculata (Rutaceae). En plus, une nouvelle coumarine, la paniculatine, a ete obtenue. En utilisant la degradation chimique et la spectroscopie u.v., r.m.n., et de masse, le nouveau compose a etb identifib comme btant le methoxy-7 (isovaleryloxyc~to-2 mbthyl-3 buty1)-8 coumarine.Canadian Journal of Chemistry, 50, 443 (1972) The plant Murraya paniculata (L.) Jack (M. exotica L.), family Rutaceae, is known to contain coumarin derivatives. Bose and Mookerjee (1) Gas chromatographic examination of foliage extracts of this plant have now revealed the presence of coumurrayin and several other coumarins. Osthol (7-methoxy-8-(3-methyl-2-buteny1)coumarin) was identified by U.V. and n.m.r. spectroscopy (5) and by co-chromatography with an authentic standard, and two other 8-isopentenyl-type derivatives present only in trace amounts were partly characterized. These, isolated by gas chromatography, had the same fluorescence and U.V. absorption characteristics as osthol. In their n.m.r. spectra doublets could be discerned at 6 6.2,7.7,6.9, and 7.4, indicating they were 8-alkyl coumarins (5). Both showed 7-methoxyl at 6 3.9 but the aliphatic end of the spectrum was obscured by instrument noise: in one derivative signals (3H?) could be seen at 6 1.23, 1.31 and 1.70, in the other at 6 1.78 and 2.42. In addition, a new coumarin for which the name paniculatin is suggested, was isolated in reasonable quantities and identified as 7-methoxy-8-( 1-isovaleryloxy-2-keto-3-methylbu- 'NRCC No. 12275. ty1)coumarin (1) on the basis of the following evidence. The compound had a molecular formula C2,H2,06, determined by mass spectroscopy (calcd. and found m/e 360.1573), and fluoresced violet under U.V. excitation in the same way as osthol. The U.V. spectrum, A, , , (EtOH) 247, 256, and 320 nm, unchanged by the addition of NaOH or AlCl,, was typical of 7-alkoxycoumarins. This was confirmed by the ['H]n.m.r. spectrum in DCCl, (Fig.

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“…265 nm, which was attributed to the absorption of nucleobase. Meanwhile, little difference in the peak intensity caused by coumarin [30] at ca. 320 nm was observed.…”

Section: Absorption Titrationmentioning

confidence: 99%

Synthesis, DNA Binding, and Cleavage Studies of Novel PNA Binding Cyclen Complexes

Wang

Zhang

et al. 2011

Chemistry & Biodiversity

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A novel coumarin-appended PNA binding cyclen derivative ligand, C1, and its copper(II) complex, C2, have been synthesized and characterized. The interaction of these compounds with DNA was systematically investigated by absorption, fluorescence, and viscometric titration, and DNA-melting and gel-electrophoresis experiments. DNA Melting and viscometric titration experiments indicate that the binding mode of C1 is a groove binding, and C2 is a multiple binding mode that involves groove binding and electrostatic binding. From the absorption-titration data, we can state that the primary interaction between CT DNA and the two compounds may be H-bonds between nucleobases. Fluorescence studies indicate that the binding ability of C1 to d(A)(9) is as twice or thrice as that of other oligodeoxynucleotides. Agarose gel-electrophoresis experiments demonstrate that C2 is an excellent chemical nuclease, which can cleave plasmid DNA completely within 24 h.

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Characterization of plant coumarins by combined gas chromatography, ultraviolet absorption spectroscopy, and nuclear magnetic resonance analysis

Cited by 44 publications

References 3 publications

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Paniculatin, a New Coumarin from Murraya paniculata (L.) Jack

Synthesis, DNA Binding, and Cleavage Studies of Novel PNA Binding Cyclen Complexes

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