Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei.

Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon.
Phytochemistry (Impact Factor: 3.35). 02/2008; 69(1):258-63. DOI: 10.1016/j.phytochem.2007.05.038
Source: PubMed

ABSTRACT Three prenylated rotenoids, elliptol, 12-deoxo-12alpha-methoxyelliptone and 6-methoxy-6a,12a-dehydrodeguelin were isolated from the twigs of Millettia duchesnei, together with the known compounds, 6a,12a-dehydrodeguelin, 6-hydroxy-6a,12a-dehydrodeguelin, 6-oxo-6a,12a-dehydrodeguelin, elliptone, 12a-hydroxyelliptone and eriodictyol. Their structures were elucidated on the basis of spectral data and comparison with information reported in the literature and with authentic specimens for some known compounds. The full NMR data of 6-oxo-6a,12a-dehydrodeguelin and 6-hydroxy-6a,12a-dehydrodeguelin are reported here for the first time.

  • [Show abstract] [Hide abstract]
    ABSTRACT: 3-Formylchromone reacts with cyclohexyl isocyanide to produce pyrano[3,4-b]chromone, which rearranges to 1-benzopyrano[2,3-c]pyridine when heated with HCl in ethanol.
    Synlett 08/2010; 2010(13):1909-1914. DOI:10.1055/s-0030-1258496 · 2.66 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Semiochemicals are natural products occurring in plants, bacteria or animals which function as carriers of a special message. Depending on the mode of function of the semiochemicals, they are divided into pheromones that trigger a response in members of the same species and allelochemicals (kairomones, allomones) that act between individuals of different species. Semiochemicals are very important compounds that influence the behavior of plants and animals and their adaption to a changing environment. As their importance for plants, animals and the ecological system itself is huge, the synthetic access to these chemicals, their precursors and derivatives is of high interest. Beyond novel strategies for the construction of semiochemical skeletons, combinatorial methods have been implemented to synthesize medium-sized and large-sized libraries that enable diverse modifications of the active compounds. These combinatorial approaches allow the screening for more active compounds and they elucidate the mode of action of the semiochemical or of the biological target. This review summarizes the state of the art procedures for the synthesis of important skeletons appearing in semiochemicals and gives special synthetic procedures for selected examples if the procedure is suitable for a general transfer to the synthesis of derivatives. The synthetic examples are given in the context of known active phytochemicals and their function that allows an evaluation of the given procedures with respect to the fulfillment of the common structural requirements (the structural diversity and flexibility) and the importance for the regulation of biological systems. Parts of this review were given in a lecture at the BioCom 12 in Cadiz, 2012.
    Phytochemistry Reviews 12/2013; 12(4). DOI:10.1007/s11101-013-9298-0 · 2.89 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: The phytochemical examination of chloroform soluble fraction (FX2) of methanolic extract of bark of Millettia ovalifolia yielded a new flavonoid; 7-(4-methoxyphenyl)-9H-furo [2,3-f]chromen-9-one (1). Compound 1 is characterized by spectroscopic analytical techniques such as UV, IR, 1D, 2D NMR spectroscopy, and mass spectrometry. A theoretical model is also developed for obtaining geometric, electronic and spectroscopic properties of 1. The geometry optimization and harmonic vibration simulations have been carried out at B3LYP/6-31G(d,p). The vibrational spectrum of compound 1 shows nice correlation with the experimental IR spectrum, through a scaling factor of 0.9613. (1)H and (13)C NMR chemical shifts are simulated using Cramer's re-parameterized function WP04 at 6-31G(d,p) basis set, and correlate nicely with the experimental chemical shifts. Copyright © 2015 Elsevier B.V. All rights reserved.
    Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 03/2015; 146. DOI:10.1016/j.saa.2015.03.061 · 2.13 Impact Factor