Effect of benzylic oxygen on the antioxidant activity of phenolic lignans

Journal of Natural Products

Volumn 68, Issue 10, 2005, Pages 1459-1470

  Yamauchi, Satoshi ^a   Hayashi, Yoshimasa ^a   Nakashima, Yuki ^a   Kirikihira, Takuya ^b   Yamada, Kazuki ^b   Masuda, Toshiya ^b  

^a EHIME UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(BENZOYL)(BENZYL)TETRAHYDROFURAN; (BENZYL)(HYDROXYBENZYL)TETRAHYDROFURAN DERIVATIVE; 2,3 BIS(4 HYDROXY 3 METHOXYBENZYL) 4 BUTANOLIDE; 3 (4 HYDROXY 3 METHOXYBENZOYL) 4 (4 HYDROXY 3 METHOXYBENZYL)TETRAHYDROFURAN; 3 [HYDROXY (4 HYDROXY 3 METHOXYPHENYL)METHYL] 4 [HYDROXY (4 HYDROXY 3 METHOXYPHENYL)METHYL]TETRAHYDROFURAN; 3,4 BIS(4 HYDROXY 3 METHOXYBENZOYL)TETRAHYDROFURAN; 3,4 BIS(4 HYDROXY 3 METHOXYBENZYL)TETRAHYDROFURAN; 3,4 BIS[HYDROXY (4 HYDROXY 3 METHOXYPHENYL)METHYL]TETRAHYDROFURAN; 4 [HYDROXY (4 HYDROXY 3 METHOXYPHENYL)METHYL] 3 (4 HYDROXY 3 METHOXYBENZYL)TETRAHYDROFURAN; 4 HYDROXY 3 METHOXYBENZOYL DERIVATIVE; 4 HYDROXY 3 METHOXYBENZYL DERIVATIVE; 5 HYDROXY 3 (4 HYDROXY 3 METHOXYPHENYL) 6 METHOXY 2,2A,8,8A TETRAHYDRONAPHTHALENE[2,3 C]TETRAHYDROFURAN; ANTIOXIDANT; BENZYL DERIVATIVE; BENZYLIC OXYGEN; BIS(4 HYDROXY 3 METHOXYBENZYL)TETRAHYDROFURAN LIGNAN; BIS(HYDROXYBENZYL)TETRAHYDROFURAN DERIVATIVE; DIBENZOYLTETRAHYDROFURAN; GAMMA BUTYROLACTONE DERIVATIVE; GAMMA BUTYROLACTONE LIGNAN; LIGNAN DERIVATIVE; LIOVIL DERIVATIVE; OXYGEN DERIVATIVE; PHENOL DERIVATIVE; PHENOLIC LIGNAN DERIVATIVE; SCAVENGER; TETRAHYDROFURAN DERIVATIVE; TETRAHYDRONAPHTHALENE TETRAHYDROFURAN; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALDOL REACTION; ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; CYCLIZATION; DIASTEREOISOMER; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; ETHERIFICATION; FRIEDEL CRAFTS REACTION; MICELLE; OPTICAL ROTATION; OXIDATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ANALYSIS;

ANTIOXIDANTS; BENZENE DERIVATIVES; COMBINATORIAL CHEMISTRY TECHNIQUES; FURANS; LIGNANS; MOLECULAR STRUCTURE; OXYGEN; PHENOLS; PLANTS, MEDICINAL; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 27844460576     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np050089s     Document Type: Article

References (19)

1. Osawa, T. In Phenolic Compounds in Food and Their Effects on Health II; Huang, M.-T., Ho, C.-T., Lee, C. Y., Eds.; American Chemical Society: Washington, DC, 1992; pp 135-149.
2. Yamauchi, S.; Ina, T.; Kirikihira, T.; Masuda, T. Biosci. Biotechnol. Biochem. 2004, 68, 183-192.
3. Yamauchi, S.; Hayashi, Y.; Kirikihira, T.; Masuda, T. Biosci. Biotechnol. Biochem. 2005, 69, 113-122.
4. Eklund, P. C.; Långvik, O.; Willfor, S. M.; Sjöholm, R. E. Polyphenols Commun. 2004, 581-582.
5. Hanuman, J. B.; Mishra, A. K.; Sabata, B. J. Chem. Soc., Perkin Trans. 1 1986, 1181-1185.
6. Freudenberg K.; Knof, L. Chem. Ber. 1957, 90, 2857-2869.
7. Tomioka, K.; Mizuguchi, H.; Koga, K. Chem. Pharm. Bull. 1982, 30, 4303-4313.
8. Yamauchi, S.; Machi, M.; Kinoshita, Y. Biosci. Biotechnol. Biochem. 1999, 63, 1453-1462.
9. Barton, G. M.; Gardner, J. A. F. J. Org. Chem. 1962, 27, 322-323.
10. Fonseca, S. F.; Campello, J. D. P.; Barata, L. E. S.; Rúveda, E. A. Phytochemistry 1978, 17, 499-502.
11. Pan, H.; Lundgren, L. N. Phytochemistry 1995, 39, 1423-1428.
12. Jossang, A.; Jossang, P.; Bodo, B. Phytochemistry 1994, 35, 547-549.
13. Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
14. Kraus, G. A.; Frazier, K. A.; Roth, B. D.; Taschner, M. J.; Neuenschwander, K. J. Org. Chem. 1981, 46, 2417-2419.
15. Staab, H. A.; Wendel, K. Chem. Ber. 1960, 93, 2902-2915.
16. Charruault, L.; Michelet, V.; Genet J.-P. Tetrahedron Lett. 2002, 43, 4757-4760.
17. Wang, B.-G.; Ebel, R.; Nugroho, B. W.; Prijono, D.; Frank, W.; Steube, K. G.; Hao, X.-J.; Proksch, P. J. Nat. Prod. 2001, 64, 1521-1526.
18. Masuda, T.; Oyama, Y. Inaba, Y.; Toi, Y.; Arata, T.; Takeda, Y.; Nakamoto, K.; Kuninaga, H.; Nishizato, S.; Nonaka, A. J. Jpn. Soc. Food Sci. Technol. 2002, 49, 652-661.
19. Masuda, T.; Yonemori, S.; Oyama, Y.; Takeda, Y.; Tanaka, T.; Andoh, T.; Shinohara, A.; Nakata, M. J. Agric. Food Chem. 1999, 47, 1749-1754.