Isolation and synthesis of new antioxidants from sunflower seeds

Natural Product Letters

Volumn 9, Issue 3, 1997, Pages 161-165

  Kato, Tadahiro ^a   Takahashi, Wataru ^a   Suzuki, Yoshiaki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Antioxidants; Arylindane skeleton; Helianthus annuus L.; Isolation; Structure determination; Synthesis

Indexed keywords

ANTIOXIDANT; BETA CAROTENE; PHENOL DERIVATIVE;

ARTICLE; PHOTOOXIDATION; PLANT SEED; SUNFLOWER;

EID: 0030902616     PISSN: 10575634     EISSN: None     Source Type: Journal    
DOI: 10.1080/10575639708048310     Document Type: Article

References (12)

1. a) A. Lanzani, M. Cardillo, and E. Fedeli (1979) Study on the antioxidant ability of chlorogenic acid isolated from sunflower seed. Riv. Ital. Sostanze Grasse, 57(7), 273-275.
2. b) In addition to (1) and (2), an antioxidant having a chromene skeleton was isolated, the result being published in Heterocycles.
3. The detailed NOE difference spectra(NOEDS) were applied for NOE experiments. Usual NOESY experiments seem not suitable for the elucidation of stereochemistry of indane skeletons since our preliminary NOESY experiments and reported evidence3,4 as well showed a positive NOE between trans protons.
4. E. Al-Farhan, P. M. Keehn, and R. Stevenson (1992) Arylpropene Cyclization and Structure of the Arylindane Product from Acorus calamus. J. Chem. Res. (S), 36-37.
5. E. Al-Farhan, P. M. Keehn, and R. Stevenson (1992) Dimerization of 3,4-Disubstituted Cinnamic Acids and Esters. Synthesis, 959-961.
6. The yield is not optimized.
7. a) see ref. 4.
8. b) B. Botta, P. Iacomacci, V. Vinciguerra, G. D. Monache, E. Gacs-Baitz, M. Botta, and D. Misiti (1990) Non-oxidative Dimerization of 3,4-Dioxygenated Cinnamates to Aryltetralin Lignans. Chem. Pharm. Bull., 38(12), 3238-3241.
9. The values(%) show the remaining β-carotene after irradiation of the β-carotene solution with a 20 W fluorescent lamp in the absence(control) or presence of the examined materials. 100% means the complete inhibition of the photooxidation.
10. A. L. Branen (1975) Toxicology and Biochemistry of Butylated Hydroxyanisole and Butylated Hydroxytoluene. J. Am. Oil. Chem. Soc., 52, 59-63.
11. For an example of recent reviews, M. H. Gordon (1996) Dietary Antioxidants in Disease Prevention. Natural Product Reports, 265-272.
12. Although irradiation at δ 3.67 of (1) corresponding to both H1 and 9-OMe caused a positive NOE with H2, the NOE may be due to the correlation between 9-OMe and H2.