Advanced SearchSearch Tips
Synthesis and the Absolute Configurations of Isoflavanone Enantiomers
facebook(new window)  Pirnt(new window) E-mail(new window) Excel Download
 Title & Authors
Synthesis and the Absolute Configurations of Isoflavanone Enantiomers
Won, Dong-Ho; Shin, Bok-Kyu; Han, Jae-Hong;
  PDF(new window)
Isoflavanone has been synthesized from the reduction of isoflavone in nearly quantitative yield. Isoflavone with seven equivalents of ammonium formate in the presence of Pd/C in ethanol under atmosphere exclusively produced the two-electron reduced product in two hours. It was characterized by various spectroscopic methods, including UV-VIS, EI-MS, -NMR, -NMR and , -COSY. The racemic mixture was separated by Sumi-Chiral column chromatography and the absolute configurations of the enantiomers were characterized by circular dichroism spectroscopy.
absolute configuration;circular dichroism (CD);flavonoids;isoflavanone;palladium on activated carbon (Pd/C);
 Cited by
Axial Conformation of 3-Methyl-2-butenoyl Group in Pyranocoumarin Ring Endows Biological Activity of (+)-Decursin,;;;;

Bulletin of the Korean Chemical Society, 2008. vol.29. 8, pp.1572-1574 crossref(new window)
Fermentation Characteristics of Wild Grape (Vitis amurensis) Wine Prepared with Reed (Phragmites communis) Root, Journal of the Korea Academia-Industrial cooperation Society, 2010, 11, 4, 1528  crossref(new windwow)
Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides, Applied Microbiology and Biotechnology, 2011, 91, 4, 1173  crossref(new windwow)
, Journal of Asian Natural Products Research, 2013, 15, 3, 286  crossref(new windwow)
Amino acid substitutions in naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4 result in regio- and stereo-specific hydroxylation of flavanone and isoflavanone, Applied Microbiology and Biotechnology, 2013, 97, 2, 693  crossref(new windwow)
Enantioselective Synthesis of Isoflavanones by Catalytic Dynamic Kinetic Resolution, Organic Letters, 2017, 19, 11, 2981  crossref(new windwow)
Ibrahim A-R and Abul-Hajj YJ (1990) Microbiological transformation of ($\pm$)-flavanone and ($\pm$)-isoflavanone. J Nat Prod 53, 644-656 crossref(new window)

Jung S-H, Cho S-H, Dang TH, Lee J-H, Ju J-H, Kim M-K, Lee S-H, Ryu J-C, and Kim Y (2003) Structural requirement of isoflavanones for the inhibitory activity of inter-leukin- 5. Eur J Med Chem 38, 537-545 crossref(new window)

Kim M, Shin B-K, Won D, and Han J (2007) Synthesis of 2'-hydroxydihydrochalcone from flavone. J Appl Biol Chem 50, 85-87

Lozovaya VV, Lygin AV, Zernova OV, Li S, Hartman GL, and Widholm JM (2004) Isoflavonoid accumulation in soybean hairy roots upon treatment with Fusarium solani. Plant Physiol Biochem 42, 671-679 crossref(new window)

Marais JPJ, Deavours B, Dixon RA, and Efrreira D (2006) The stereochemistry of flavonoids. In The Science of Flavonoids, Grotewold E pp. 1-46, Springer, New York, USA

Moffitt M, Woodward RB, Klyne MW, and Djerassi C (1961) Structure and the optical rotatory dispersion of saturated ketones. J Am Chem Soc 83, 4013-4018 crossref(new window)

Salakka AK, Jokela TH, and Wahala K (2006) Mutiple hydride reduction pathways in isoflavonoids. Beilstein J Org Chem 2, 16-24 crossref(new window)

Slade D, Ferreira D, and Marais JPJ (2005) Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry 66, 2177-2215 crossref(new window)

Szabo V and Antal E (1973) The selective reduction of isoflavone. Tetrahed Lett 14, 1659-1662 crossref(new window)

Wang X-L, Hur H-G, Lee JH, Kim KT, and Kim S-I (2005) Enantioselective synthesis of S-equol from dihydrodaidzein by an newly isolated anaerobic human intestinal bacterium. Appl Environ Microbiol 71, 214-219 crossref(new window)