Determination of aqueous stability and degradation products of series of coumarin dimers

Dragojević, Snježana; Šunjić, Vitomir; Bencetić-Mihaljević, Vlatka; Ralić, Jovica; Mesić, Milan; Elenkov, Ivaylo; Sučić, Anita Filipović; Klonkay, Andreja Čempuh; Lerman, Lidija; Ilijaš, Marina; Gabelica-Marković, Vesna; Malnar, Ivica

doi:10.1016/j.jpba.2010.08.002

Cited by 6 publications

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“…The first report dates back to 1957 and has been based merely on the isolation and structure characterization (elemental analysis and mixed melting point) of these compounds . HPLC-supported stability studies (thermal, chemical, and photochemical) were performed using a UV detector at two wavelengths and subsequently an HPLC/photodiode array detector alone or in combination with a fluorescence one. , Despite its therapeutic potential, studies on the chemical stability of umbelliprenin and prenyloxycoumarins in general have not been systematically explored and still represent a field of current interest. Herein, a detailed investigation on the chemical stability of umbelliprenin under thermal, photochemical, oxidative, and hydrolytic stress conditions both in solution (e.g., EtOH) and in the solid form using TLC and HPLC-UV/vis for analysis is described.…”

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Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species

et al. 2017

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Umbelliprenin is a secondary plant metabolite that displays promising chemopreventive, anti-inflammatory, and antigenotoxic properties. It possesses potential for applications to human welfare notably to prevent the emergence of cancer. For this purpose, stability studies are needed to define proper storage conditions and adapted formulations for this drug candidate. The identification of degradative products is a major concern for the preclinical development of umbelliprenin, providing also interesting information related to potential original phytochemicals formed in plants exposed to stressors. The stability profile of umbelliprenin under various stress conditions including exposure to heat, light, oxidation, and hydrolytic medium was assessed via HPLC/UV data. The data support that umbelliprenin undergoes inter- and intramolecular [2+2] cycloaddition under light exposure, leading respectively to a cyclobutane-umbelliprenin dimer and a 16-membered macrocycle. Their structures were characterized via MS and NMR data. It was shown that UV-A filters prevent this process, whereas UV-B filters and antioxidants are not or weakly effective. The study provides useful information for the preclinical development of umbelliprenin as an original chemopreventive agent.

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Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species

et al. 2017

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“…Further, hemiacetals 2 proved to be the most active ones, regarding the in vitro activity, but during evaluation were proven to be chemically unstable and because of that were not fully investigated. 48 Acetals 3 and rearranged compounds 4 are equally potent inhibitors of mast cell (RBL-2H3) degranulation (Fctriggered).…”

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Synthesis and Anti-inflammatory Activity of Novel Furochromenes

et al. 2013

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Abstract. A series of variously substituted furochromenes, hemiacetals 2, acetals 3, and rearranged compounds 4, were synthesized from variously substituted 4-hydroxycoumarins and evaluated in several in vitro assays, inhibition of mast cell degranulation induced by the activation of Fcε receptor type I or calcium ionophore and leukotriene B 4 (LTB 4 ) inhibition. The most active derivatives, 3p and 4p (8-iso-propyl substitution in coumarin ring) and 3r (5-methyl-8-chloro substitution), showed significant inhibition of mast cell degranulation (Fctriggered) and LTB 4 , and exhibited significant local anti-inflammatory activity in PMA induced ear edema in CD1 mice, with potency equal (compounds 3p and 4p) or better (compound 3r) in comparison with zileuton, a reference drug used. It might be a promising direction for developing novel drugs as potential agents for the treatment of allergies and other inflammatory diseases.(doi: 10.5562/cca2240)

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Systematic Exploration of Indolizine-Based Small Fluorescent Molecules

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Determination of aqueous stability and degradation products of series of coumarin dimers

Cited by 6 publications

References 31 publications

Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species

Characterization of the Degradation Profile of Umbelliprenin, a Bioactive Prenylated Coumarin of a Ferulago Species

Synthesis and Anti-inflammatory Activity of Novel Furochromenes

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