NMR spectra of natural coumarin derivatives

Perel'son, M. E.; Sheinker, Yu. N.; Syrova, G. P.; Turchin, K. F.

doi:10.1007/bf00564146

Cited by 13 publications

(7 citation statements)

References 6 publications

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“…The yellowbrown extract obtained was subjected to repeated column chromatography on silica gel, eluting with hexane followed by ethyl acetate in hexane with increasing polarity as mobile phase to obtain compounds 1-5 ( Figure 1). These compounds were in agreement with data reported previously, identifying them as marmin 1 (HEN1), imperatorin 2 (HEN2) (Muller et al, 2004), xanthoxyletin 3 (HEN3), 6,7-Dimethoxycoumarin 4 (HEN4) (Perel'son et al, 1970) and 1-hydroxy-3-methoxy-acridone 5 (HEN5) (Spatafora and Tringaliw, 1997).…”

Section: Resultssupporting

confidence: 92%

Anti-toxoplasma gondii activity of constituents from Balsamocitrus camerunensis L (Rutaceae)

Happi¹,

Mbosso²,

Nguemfo³

et al. 2014

Afr. J. Biotechnol.

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Section: Resultssupporting

confidence: 92%

Anti-toxoplasma gondii activity of constituents from Balsamocitrus camerunensis L (Rutaceae)

Happi¹,

Mbosso²,

Nguemfo³

et al. 2014

Afr. J. Biotechnol.

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“…Unlike U‐a , which bears one proton in position III and one in position IV observed as doublets at 6.23 and 7.59 ppm (see Experimental section), MU‐a contains a single proton in position III observed as a singlet at 6.11 ppm and a methyl group at position IV observed as a singlet at 2.36 ppm. As in other reported coumarins substituted in position VII, the absence of a singlet in the entire aromatic region on the spectrum of MU‐a indicates that only one isomer shown in Scheme and Figure was obtained following the synthesis procedure herein described.…”

Section: Resultssupporting

confidence: 70%

Tailor-made and chemically designed synthesis of coumarin-containing benzoxazines and their reactivity study toward their thermosets

Froimowicz

Arza²,

Ohashi³

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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Coumarins are used as a natural renewable resource to synthesize coumarin-containing benzoxazine resins. The coumarin-containing benzoxazines are fully characterized in terms of their chemical structure by Fourier-transform infrared spectroscopy and proton nuclear magnetic resonance spectroscopy. The influence of electronic effects caused by the substituents on the polymerization temperature is also evaluated. Thermal properties of the resulting thermosets are characterized by differential scanning calorimetry and thermogravimetric analysis, showing good stability and char yields higher than 50%.The coumarin-containing polybenzoxazine thermosets show T g values in the range between 160 and 190 8C. Thus, the herein presented coumarin-containing benzoxazine resins are proven to be competitive monomers when compared with other petroleum-based benzoxazine resins toward the generation of high-performance thermoset.

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“…The metabolite was soluble in methanol and hot water. The interpretation of 1 H data of metabolite X (Table 2) showed the absence of H-4 signals resonating at δ H 7.76 ppm, which is consistent with the ortho effect of introduced hydroxyl group (Sothers, 1972) at C-67.45 and 7.76 ppm in coumarin (Perel`son et al, 1970). H-3 for metabolite X revealed an upfield shift of 0.85 ppm.…”

Section: H Andsupporting

confidence: 67%

“…1 H and 13 C NMR data of metabolite (VII) are shown in Table 2, which lacked the H-6, H-7 signals resonating at δ H 7.19, 7.45 in coumarin (Perel`son et al, 1970). Furthermore, H-5 signal for this metabolite underwent an upfield shift of 0.51 ppm, which is consistent with the ortho effect of introduced hydroxyl group (Sothers, 1972) at C-6.…”

Section: Resultsmentioning

confidence: 59%

Biotransformation of coumarins by Cunninghamella elegans

Attia¹,

Abou-El-seoud²,

Ibrahim³

2016

Afr. J. Pharm. Pharmacol.

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Microbial biotransformation of coumarin (I) was undertaken using a battery of twenty five microorganisms. Among them, the fungus Cunninghamella elegans NRRL 1392 was the sole microbe that efficiently metabolized coumarin (I) into umbelliferone (II), 3, 4-dihydrocoumarin (V) and transcinnamic acid (VI). Umbelliferone was also biotransformed into 6, 7-dihydroxycoumarin (aesculetin, VII) and p-coumaric acid (VIII). On the other hand, warfarin (III) was biotransformed into 4`hydroxywarfarin (IX) and also dicoumarol (IV) was transformed into 4-hydroxycoumarin (X) by the same microorganism. The structures of the metabolites were established using only one property and spectroscopic techniques including melting points, 1 H NMR, 13 C NMR and mass spectroscopy. The cytotoxic effect of coumarin substrates and their metabolites was also investigated.

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NMR spectra of natural coumarin derivatives

Cited by 13 publications

References 6 publications

Anti-toxoplasma gondii activity of constituents from Balsamocitrus camerunensis L (Rutaceae)

Anti-toxoplasma gondii activity of constituents from Balsamocitrus camerunensis L (Rutaceae)

Tailor-made and chemically designed synthesis of coumarin-containing benzoxazines and their reactivity study toward their thermosets

Biotransformation of coumarins by Cunninghamella elegans

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