Dihydroguaiaretic acid

Isogai et al. (1973) isolated five phenyl pro-panoids from the seed kernel of nutmeg. Park et al. (1998) isolated dihydroguaiaretic acid from mace. 

Park, S., Fee, D.K. and Yang, C.H. (1998) Inhibition of fos-jun-DNA complex formation by dihydroguaiaretic acid and in vitro cytotoxic effects on cancer cells. Cancer Letters 1 27, 23-28. 

AP = ascorbyl palmitate, BHA = butylated hydroxyanisole, BHT = butylated hydroxytoluene, TDPA = thiodipropionic acid, PG = propyl gallate, NDGA = nor-dihydroguaiaretic acid, TBHQ 2- er -butylhydroquinone. 

The antioxidant activity of a series of lignans was studied by Faure et al. [232] in a rat brain homogenate autoxidation test, and lipid peroxidation was evaluated from the luminescence intensity and thiobarbituric reactive product accumulation. Isopregomisin (0.7 pM) was the most active lignan, followed by guayacasin (1.1 pM) and dihydroguaiaretic acid (2.8 pM). The difference in the effect can be explained by the degree of methylation, which increases the activity. 

Evan, A.R, and K.D. Gardner. 1979. Nephron obstruction in nor-dihydroguaiaretic acid-induced renal cystic disease. Kidney Int. 15(1) 7-19. 

Siddique, Y.H., T. Beg, and M. Afzal. 2006. Protective effect of nor-dihydroguaiaretic acid (NDGA) against norgestrel induced genotoxic damage. Toxicol. In Vitro 20(2) 227-233. 

Anisomelic acid, A-60275 Citlalitrione, C-80135 Cynajapogenin A, C-70257 Dtsoxyarticulin, in A-60307 Dihydroguaiaretic acid, in G-70033... 

Totally synthetic nor-dihydroguaiaretic acid (1.3b) became available in 1934 (75). When NDGA began to be required in quantity (see Section XIII), this and subsequently published syntheses 30, 60, 78,... 

Subsequent to the isolation of partially 0-demethylated dihydro-guaiaretic acid (1.3c), it was proposed to call this compound or-dihydro-guaiaretic acid, and 1.3b ftwwor-dihydroguaiaretic acid (63). Adoption of this proposal would lead to confusion, in view of the voluminous literature on NDGA (1.3b) (see Section XIII). 

An additional technique which yielded structural and stereochemical information in this series involves reduction with sodium in liquid ammonia. This also leads, accordihg to the conditions used, to two types of product, 28, a dihydroguaiaretic acid, and 29, again an aryl-tetralin. Chart 7 exemplifies the reaction sequence for veraguensin (47). 

Burk, D., and M. Woods Hydrogen Peroxide, Catalase, Glutathione Peroxidase, Quinones, Nor-dihydroguaiaretic Acid, and Phosphopyridine Nucleotides in Relation to X-Ray Action on Cancer Cells. Radiation Res. Suppl. 3, 212 (1963) apud Chem. Abstr. 59, 1934 (1963). 

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