BIOCHEMICAL AND MODEL CHEMICAL-REACTIONS FOR THE BASIS OF RED PIGMENT IN FLUE-CURED TOBACCO

被引:16
作者
WEEKS, WW
CAMPOS, MP
MOLDOVEANU, S
机构
[1] CO CIGARROS SOUZA CRUZ,RIO JANEIRO,BRAZIL
[2] BROWN & WILLIAMSON TOBACCO CO,LOUISVILLE,KY
关键词
D O I
10.1021/jf00032a030
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Polyphenol oxidase (PPO) preparations from green tobacco leaves oxidized chlorogenic and caffeic acids to o-quinones, which reacted in vitro with nornicotine to produce red color at 570 nm. Activity was not obtained when ferulic acid was used as a substrate. Variable temperature data showed PPO was stable for 1 h at 75-degrees-C. Nicotine, myosmine, pyrrolidine, asparagine, alanine, and glutamic acid failed to react with chlorogenic acid and enzyme; nor did these compounds interfere with color development between nornicotine and o-quinones. Aqueous ethanolic extracts (80%) gave similar red color from tobacco grade FR and cherry red tobacco (CR) but a brown color from orange tobacco grade F. Alkaloid analysis showed CR and FR grade tobaccos contained higher levels of nornicotine than F grade tobacco. Model chemical reactions with nornicotine showed coupling of nornicotine with o- and p-quinones by Schiff base and Michael addition reaction.
引用
收藏
页码:1321 / 1328
页数:8
相关论文
共 22 条
  • [1] ADLER E, 1971, ACTA CHEM SCAND, V13, P505
  • [2] BALOGH V, 1971, J ORG CHEM, V36, P1339
  • [3] BOWMAN DT, 1985, TOBACCO SCI, V29, P47
  • [4] BOYETTE MD, 1986, GUIDE BULK CURING TO
  • [5] N-VINYL AS N-H PROTECTING GROUP - CONVENIENT SYNTHESIS OF MYOSMINE
    BRANDANGE, S
    LINDBLOM, L
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1976, 30 (01): : 93 - 93
  • [6] CHORTYK O. T., 1967, TOBACCO SCI, V11, P137
  • [7] CUNDIFF R. H., 1964, TOBACCO SCI, V8, P136
  • [8] DYMICKY M., 1967, TOBACCO SCI, V11, P42
  • [9] MUSCARUFIN .2. 2-(4-CARBOXYBUTA-1,3-DIENYL)- 1,4-BENZOQUINONES
    EDWARDS, RL
    LEWIS, DG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1959, (NOV): : 3254 - 3258
  • [10] FIESER LF, 1975, REAGENTS ORGANIC SYN, V5