SOME DERIVATIVES OF COUMARIN.1

Francis D. Dodge

doi:10.1021/ja02259a030

Isolation and HPLC quantitation of kaurane-type diterpenes and cinnamic acid derivatives of long-term stored leaves of Mikania laevigata and Mikania glomerata

Anais da Academia Brasileira de Ciências ◽

10.1590/s0001-37652013005000029 ◽

2013 ◽

Vol 85 (2) ◽

pp. 473-486 ◽

Cited By ~ 5

Author(s):

SUZAN K.V. BERTOLUCCI ◽

ANA B.D. PEREIRA ◽

JOSE E.B.P. PINTO ◽

ALAIDE B. OLIVEIRA ◽

FERNAO C. BRAGA

Keyword(s):

Spectral Purity ◽

Chemical Markers ◽

Cinnamic Acid Derivatives ◽

Mikania Laevigata ◽

Coumarin 1 ◽

Derivatives Of ◽

Mikania Glomerata ◽

Dark Room ◽

Chromatographic Profiles

The leaves of Mikania laevigata and Mikania glomerata are used in Brazil to treat respiratory affections, being kaurane-type diterpenes and coumarin considered as the bioactive compounds. The present study reports an investigation on the HPLC-DAD profiles and contents of coumarin (1), trans-o-coumaric (2), kaurenoic (3), benzoylgrandifloric (4) and cinnamoylgrandifloric (5) acids in dried leaves of Mikania species stored in dark room under controlled conditions. Excepting 2, the constituents were isolated and purified to be employed as reference compounds. The samples were analyzed at three monthly intervals up to 18 months for M. laevigata and 12 months for M. glomerata. trans-o-Coumaric was not detected in both, whereas 1 occurred only in M. laevigata. The concentrations of the assayed constituents did not vary significantly within the evaluated period (p < 0.05), for both species. In contrast, changes in the chromatographic profiles and spectral purity of peaks from 3, 4 and 5 were detected in samples of both Mikania stored for three months, while the coumarin profile in M. laevigata modified after six months of storage. The evaluation of chromatographic profiles based on spectral purity analyses of selected peaks was shown to be a more robust tool to access chemical stability of Mikania samples than the quantitation of chemical markers' contents.

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Spectroscopy and electronic structure of coumarins with fixed amine and 3-substitution derivatives of coumarin 1

Soviet Physics Journal ◽

10.1007/bf00898583 ◽

1991 ◽

Vol 34 (10) ◽

pp. 877-884

Author(s):

N. Yu. Vasil'eva ◽

I. V. Sokolova ◽

N. F. Vasil'ev

Keyword(s):

Electronic Structure ◽

Coumarin 1 ◽

Derivatives Of

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On the Structure of Peuarenarine, a New Coumarin from Peucedanum Arenarium

Zeitschrift für Naturforschung B ◽

10.1515/znb-1971-0211 ◽

1971 ◽

Vol 26 (2) ◽

pp. 113-114 ◽

Cited By ~ 6

Author(s):

A. Zheleva ◽

L. Bubeva-Ivanova ◽

S. L. Spassov

Keyword(s):

Spectral Data ◽

Nmr Spectra ◽

Ir And Nmr Spectra ◽

Natural Coumarin ◽

Coumarin 1 ◽

Derivatives Of

Three new natural coumarin substances 1, 2 and 3 (derivatives of 2′,2′-dimethyl-3′,4′-dihydroxydihydropyrano-5′,6′:6,7-coumarin) were isolated from the roots and fruits of Peucedanum arenarium W.K.On the basis of the spectral data from UV, IR, and NMR spectra of coumarin 1, named peuarenarine, it was assumed, that, it is an ester of 2′,2′-dimethyl-3′,4′-dihydroxy-dihydropyrano-5′,6′:6,7-coumarin and of angelic and 2,3-epoxy-2-methylbutyric acids.

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Applicability of 1,6-Diphenylquinolin-2-one Derivatives as Fluorescent Sensors for Monitoring the Progress of Photopolymerisation Processes and as Photosensitisers for Bimolecular Photoinitiating Systems

Polymers ◽

10.3390/polym11111756 ◽

2019 ◽

Vol 11 (11) ◽

pp. 1756 ◽

Cited By ~ 4

Author(s):

Monika Topa ◽

Filip Petko ◽

Mariusz Galek ◽

Kamil Machowski ◽

Maciej Pilch ◽

...

Keyword(s):

Fluorescence Probe ◽

Emission Spectra ◽

Triethylene Glycol ◽

Fluorescent Sensors ◽

Fluorescence Sensors ◽

Molecular Sensors ◽

Trimethylolpropane Triacrylate ◽

Molecular Fluorescence ◽

Coumarin 1 ◽

Derivatives Of

The applicability of new 1,6-diphenylquinolin-2-oneas derivatives as fluorescent molecular sensors for monitoring the progress of photopolymerisation processes by Fluorescence Probe Technique (FPT) has been tested. The progress of cationic, free-radical and thiol-ene photopolymerisation for commercially available monomers: triethylene glycol divinyl ether (TEGDVE), trimethylolpropane triacrylate (TMPTA) and trimethylpropane tris(3-mercaptopropropionate) (MERCAPTO) was monitored. It was found that new derivatives of 1,6-diphenylquinolin-2-one shifted their fluorescence spectra towards shorter wavelengths with the progress of polymerisation, which enabled monitoring the progress in terms of fluorescence intensity ratios as the progress indicator. Derivatives of 1,6-diphenylquinolin-2-one show sensitivity to changes in both polarity and viscosity in the surrounding microenvironment during photopolymerisation processes. Therefore, it was shown that they are good candidates to act as fluorescent sensors for monitoring the kinetics of very quick processes, such as photopolymerisation processes. Furthermore, the effect of the nature of substituents attached to the 1,6-diphenylquinolin-2-one ring on the characteristics of emission spectra was identified. Moreover, the sensitivity of fluorescent sensors was compared with commercially available model sensors, such as 7-diethylamino-4-methylcoumarin (Coumarin 1) and trans-2-(2′,5′-dimethoxyphenyl)ethenyl-2,3,4,5,6-pentafluorobenzene (25ST). Moreover, it was also proven that selected derivatives of 1,6-diphenylquinolin-2-one exhibit an accelerating effect on the progress of cationic photopolymerisation of vinyl monomers (TEGDVE). Thus, the new 1,6-diphenylquinolin-2-one derivatives can be successfully used both as molecular fluorescence sensors to monitor the progress of photopolymerisation processes and as diaryliodonium salt photosensitisers to initiate cationic photopolymerisation processes in a UV-A range of 365 nm.

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