Conversion of procyanidin B-type (catechin dimer) to A-type: Evidence for abstraction of C-2 hydrogen in catechin during radical oxidation

Tetrahedron Letters

Volumn 41, Issue 4, 2000, Pages 485-488

  Kondo, Kazunari ^a   Kurihara, Masaaki ^a   Fukuhara, Kiyoshi ^a   Tanaka, Takashi ^b   Suzuki, Takashi ^a   Miyata, Naoki ^a   Toyoda, Masatake ^a  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^b NAGASAKI UNIVERSITY   (Japan)

Author keywords

Antioxidant; Bond dissociation enthalpy; Polyphenols; Radicals

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ANTIOXIDANT; CATECHIN; HYDROGEN; POLYPHENOL; PROCYANIDIN DERIVATIVE; QUERCETIN;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION; DISSOCIATION; DRUG STRUCTURE; ELECTRON TRANSPORT; ENTHALPY; LIPID PEROXIDATION; OXIDATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0034700824     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02097-3     Document Type: Article

References (13)

1. Brown, J. P. A. A. Mutat. Res. 1980, 75, 243.
2. Sano, M.; Suzuki, M.; Miyase, T.; Yoshino, K.; Maeda-Yamamoto, M. J. Agric. Food Chem. 1999, 47, 1906.
3. Ariga, T.; Hamamoto, M. Fragrance J. 1994, 22, 52.
4. Kondo, K.; Kurihara, M.; Miyata, N.; Suzuki, T.; Toyoda, M. Arch. Biochem. Biophys. 1999, 362, 79.
5. Kondo, K.; Kurihara, M.; Miyata, N.; Suzuki, T.; Toyoda, M. Free Radical Biol. Med. 1999, 27, 855.
6. Although the BDE for the C-2 hydrogen in EC (69.1 kcal/mol) was lower than that for the phenolic OH (ca. 75 kcal/mol), the first abstraction (an electron and then hydrogen) from EC probably occurred at the phenolic OH.
7. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Free Radical Biol. Med. 1996, 20, 933.
8. Satoshi, M.; Nanaka, G.; Nishioka, I. Chem. Pharm. Bull. 1987, 35, 4717.
9. To 200 μM of PB-1, DPPH (2 mM) was added and the mixture stood at 40°C. In LC/MS analysis, ODS column was used and MeOH/1% AcOH was used as an eluent. The flow rate was 0.2 ml/min.
10. ® version 6.5, Schrödinger Inc. Jersey City, NJ; MonteCarlo method, MM2* force field) and then the bond dissociation enthalpies (BDEs) were calculated using the semiempirical AM1 method. The BDEs at the phenolic OH were ca. 75 kcal/mol.
11. The ion peak (m/z 425) by fragmentation and the ion peak (m/z 287) by retro-Diels-Alder fission were observed as reported by Karchesy et al. in: Anal. Chem. 1986, 58, 2563.
12. Procyanidin A-types (PA-1 and PA-2) are natural products found in plants such as peanut skins.
13. Saint-Cricq de Gaulejac, N.; Provost, C.; Vivas, N. J. Agric. Food Chem. 1999, 47, 425.