Synthesis, structural revision, and antioxidant activities of antimutagenic homoisoflavonoids from Hoffmanosseggia intricata

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 5, 2007, Pages 1288-1290

  Siddaiah, Vidavalur ^a   Maheswara, Muchchintala ^a   Venkata Rao, Chunduri ^a   Venkateswarlu, Somepalli ^b   Subbaraju, Gottumukkala V ^b  

^a SRI VENKATESWARA UNIVERSITY   (India)

^b Laila Research Centre   (India)

Author keywords

Antioxidant activity; Homoisoflavonoids; Revised structure; Synthesis

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; HOFFMANOSSEGGIA INTRICATA EXTRACT; HOMOISOFLAVONE DERIVATIVE; NATURAL PRODUCT; PLANT EXTRACT; PYROGALLOL; SCAVENGER; SUPEROXIDE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HOFFMANOSSEGGIA INTRICATA; MEDICINAL PLANT;

ANTIMUTAGENIC AGENTS; ANTIOXIDANTS; CHROMONES; FREE RADICAL SCAVENGERS; ISOFLAVONES; MOLECULAR STRUCTURE; PYROGALLOL; STRUCTURE-ACTIVITY RELATIONSHIP; SUPEROXIDES;

CAESALPINIA PULCHERRIMA;

EID: 33846913943     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.12.008     Document Type: Article

References (17)

1. Lockhart I.M. In: Ellis G.P. (Ed). The Chemistry of Heterocylic Compounds: Chromenes, chromanones and chromones (1977), John Wiley & Sons, New York
2. A1 Nakib T., Bezjak V., Meegan M.J., and Chandy R. Eur. J. Med. Chem. 25 (1990) 455
3. Kirkiacharian S., Gomis M., and Koutsourakis P. Eur. J. Med. Chem. 24 (1989) 309
4. Desideri N., Olivieri S., Stein M.L., Sgro R., Orsi N., and Conti C. Antiviral Chem. Chemother. 8 (1997) 545
5. Wall M.E., Wani M.C., Manikumar H.T., Taylor H., and McGivney R. J. Nat. Prod. 52 (1989) 774
6. Siddaiah V., Venkata Rao C., Venkateswarlu S., and Subbaraju G.V. Tetrahedron 62 (2006) 841
7. Siddaiah V., Venkata Rao C., Venkateswarlu S., Krishnaraju A.V., and Subbaraju G.V. Bioorg. Med. Chem. 14 (2006) 2545
8. General procedure for the preparation of E-homoisoflavonoids: A mixture of chroman-4-one 8 (1.22 mmol), substituted benzaldehyde (1.76 mmol), and piperidine (five drops) was heated at 70-80 °C for 2 h. The cooled reaction mixture was diluted with water (50 mL), acidified with dil HCl, and extracted with ethyl acetate (3× 50 mL). The combined EtOAc layer was washed with water (30 mL), brine (30 mL) and dried over sodium sulfate. The residue obtained after evaporation of the solvent was chromatographed over silica gel column using mixtures of petroleum ether and ethyl acetate as eluents to give homoisoflavonoids.
9. 6: C, 64.00; H, 4.03. Found: C, 63.97; H, 4.06.
10. Bohler P., and Tamm Ch. Tetrahedron Lett. (1967) 3479
11. McPherson D.D., Cordell G.A., Soejarto D.D., Pezzuto J.M., and Fong H.H.S. Phytochemistry 22 (1983) 2835
12. Namikoshi M., Nakata H., and Saitoh T. Phytochemistry 26 (1987) 1831
13. McCord J.M., and Fridovich I. J. Biol. Chem. 244 (1969) 6049
14. Venkateswarlu S., Ramachandra M.S., and Subbaraju G.V. Bioorg. Med. Chem. 13 (2005) 6374
15. Wang M., Jin Y., and Ho C.-T. J. Agric. Food Chem. 47 (1999) 3974
16. Lamaison J.L., Petitjean-Freyter C., and Carnat A. Pharm. Acta Helv. 66 (1997) 185
17. Matsuda H., Wang T., Managi H., and Yoshikawa M. Bioorg. Med. Chem. 11 (2003) 5317