Pinostrobin and Cajanus lactone isolated from Cajanus cajan (L.) leaves inhibits TNF-α and IL-1β production: In vitro and in vivo experimentation

Simirgiotis

et al. 2015

J. Chil. Chem. Soc.

The bioactive compound 5-hydroxy-7-methoxy-2-phenylchroman-4-one (pinostrobin, I), was isolated from aerial parts of Nolana ramossisima I.M. Johnst., a Chilean endemic species, using a combination of medium pressure column chromatography and high speed countercurrent liquid-liquid chromatography (HSCCC). The compound crystallized as a non-centrosymmetric polymorph in the orthorhombic chiral space group P2 1 2 1 2 1 . Its structure had been previously reported by Shoja (Acta Cryst. C45, 828, 1989) and Yamovoi et al. (Khim. Prir. Soedin (5), 361, 2001) in the centrosymmetric space groups Pbca and P21/c, respectively.

Section: Introductionmentioning

confidence: 99%

A Non-Centrosymmetric Polymorph of 5-Hydroxy-7-Methoxy-2-Phenylchroman-4-One

Simirgiotis

et al. 2015

J. Chil. Chem. Soc.

“…Flavonoids exhibit a several biological activities, as anti-bacterial, anti-inflamatory and anti-oxidant [7][8][9][10]. One of these flavonoids, pinostrobin (5-hydroxy-7-methoxyflavanone) had been identified and studied for about six decades for his potential therapeutic properties in various diseases such as cancer, considered as a good candidate for a leukemia chemopreventic agent or in the treatment of human mammary carcinoma [4,[11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Electronic and Structural Properties of 5-Hydroxy-7-Metoxyflavanone: A Theoretical Approach

Padilla-Campos

Zárate

2016

J. Chil. Chem. Soc.

Electronic and structural properties of two polymorphic modifications of 5-hydroxy-7-methoxyflavanone (pinostrobin) were theoretically investigated and compared with experimental crystallographic data. In the literature, four polymorphic modifications of pinostrobin had been reported. The present study has established that only two of them are relevant as they differ only in the position of the methoxy group whereas other structures are derived from the rotation of the phenyl group. Both structures differ in about 1.5 kJ/mol, but the activation energy of methoxy torsion was greater than 16 kJ/mol. In addition, both have similar electronic structures but it was established with slight differences in reactivity.

“…The range of available flavanones includes (±)-pinostrobin (1), isolated from balsam poplar Populus balsamifera L. 1 The compound 1 has been shown to possess antiproliferative, 2 antimicrobial, 3 neuroprotective, 4 and anti-inflammatory 5 proper-ties. The development of methods for chemical modification of pinostrobin (1) opens new possibilities for creating new compounds with specific biological activity.…”

mentioning

confidence: 99%

The flavanone pinostrobin in the synthesis of coumarin-chalcone hybrids with a triazole linker

Lipeeva

Жанымханова²,

Шульц

et al. 2015

Chem Heterocycl Comp

Flavonoids, including flavones, flavanones, flavanols, and isoflavones, are an important type of plant polyphenols. The range of available flavanones includes (±)-pinostrobin (1), isolated from balsam poplar Populus balsamifera L. 1 The compound 1 has been shown to possess antiproliferative, 2 antimicrobial, 3 neuroprotective, 4 and anti-inflammatory 5 proper-ties. The development of methods for chemical modification of pinostrobin (1) opens new possibilities for creating new compounds with specific biological activity. Our attention was drawn to the possibility to obtain functionalized chalcones from pinostrobin (1) and to perform subsequent transforma-tions in order to build hybrid structures, in particular com-pounds that would combine both chalcone and coumarin fragments.Modified chalcones are of interest for the creation of new drugs against various types of oncological and viral diseases, as well as diabetes. 6 Coumarin-chalcone hybrids have been previously characterized with regard to antimicrobial, 7 antitumor, 8 and anti-inflammatory 9 activity. Structure-activity studies have provided data about the effect of substituents in the chalcone and coumarin fragments on the selectivity of cytotoxic activity with regard to human tumor cells. 8 The analysis of a library of coumarin derivatives, conjugated with 1,2,3-triazole ring at positions 3, 10 4, or 7 11,12 of the coumarin system, showed that triazole ring is an important structural feature for the creation of selective antitumor agents -inducers of tumor cell apoptosis and specific inhibitors of the G2 phase in cell division. Besides that, 1,2,3-triazoles were characterized as potential inhibitors of PDE4В phosphodiesterase, which reduced the proliferation of lung cancer cells and inhibited their angiogenesis. 13 For these reasons, we were interested in the synthesis and study of coumarin-chalcone hybrids containing a 1,2,3-triazole linker. Our objective was to develop a method for the preparation of 2-(bromoalkoxy)-and related 2-(azidoalkoxy)chalcones from pinostrobin (1) and to investigate the possibilities for using these new azides in the synthesis of coumarin-chalcone hybrids.The reaction of pinostrobin (1) with dihaloalkanes (1,4-dibromobutane (2), 1,5-dibromopentane (3), or 1,6-dibromoThe reaction of flavanone pinostrobin with dibromoalkanes in acetone in the presence of potassium carbonate followed the path of retroMichael addition -О-alkylation and resulted in the formation of the respective 2-(bromoalkoxy)chalcones. Treatment of the latter with sodium azide gave the respective azides, which were highly active in the Сu-catalyzed 1,3-dipolar cycloaddition reaction. The reaction of these azides with 6-substituted 7-ethynylcoumarins gave coumarin-chalcone hybrids containing a 1,2,3-triazole linker.