Two new isoflavones, fremontin and fremontone, were isolated from roots of Psorothamnus fremontii (Fabaceae), a desert plant. Compound 1 has the structure 5'-(alpha, alpha-dimethylallyl)-5,7,2',4'-tetrahydroxyisoflavone; compound 2 is similar but also contains the 3'-(gamma,gamma-dimethylallyl) substituent. The alpha,alpha-dimethylallyl substituent is rarely observed, and the combination of the alpha,alpha- and gamma,gamma-dimethylallyl substituents is unprecedented. Both 1 and 2 were nontoxic toward Salmonella typhimurium and were both highly active in the inhibition of mutagenicity of ethyl methanesulfonate (EMS) at all concentrations tested. Compound 2 was more active than 1 in the inhibition of mutagenicity of 2-aminoanthracene (2AN) and acetylaminofluorene (AAF) toward S. typhimurium.

Intricatin [1] and intricatinol [2] are new homoisoflavonoids isolated from a desert plant Hoffmanosseggia intricata, which was collected in Baja California, Mexico. The structures of the compounds were elucidated using a variety of spectroscopic techniques. The structure of 1 was shown to be 7,4'-dimethoxy-8-hydroxyhomoisoflavone, and 2 was shown to be 4'-methoxy-7,8-dihydroxyhomoisoflavone. Both compounds 1 and 2 displayed activity in the inhibition of the mutagenicity of 2AN toward Salmonella typhimurium (T98). Compound 2 was much more active than 1 in the case of the inhibition of the mutagenicity of AAF toward S. typhimurium (T98) and the inhibition of EMS towards S. typhimurium (T100). Compounds 1 and 2 are the first examples of antimutagenic activity in homoisoflavones.

Several coumarins were isolated from crude plant extracts by means of an antimutagenic assay procedure. These coumarins included psoralen from Psoralea corylifolia and imperatorin and osthol from Selinum monniere. Studies of structure-activity relationships of these and several other available coumarins were carried out with four mutagens. All of the coumarins were nontoxic and in particular showed high activity in the inhibition of the mutagenicity of benzo[a]pyrene.

Maesol, a novel dimeric phenol, was isolated from seeds of Maesa montana and Maesa indica. Maesol was shown to have the formula C28H42O4 with structure 1, a dimeric, symmetrical 1,12-bis(3,3'-dihydroxy-4,4'-dimethyl-5,5'-dimethoxyphenyl)dodecane. It is the first compound with such structure to be isolated from plant material. Structure elucidation was based largely on 1H- and 13C-nmr techniques and comparison with a known synthetic isomeric dimer 3. Although crude extracts showed strong inhibition of 2-aminoanthracene activity against Salmonella typhimurium (T-98), the pure compound was inactive when tested for inhibition of the mutagenic activity of several mutagens.

A number of known prenylated flavonoids were isolated from Psoralea corylifolia using an assay procedure based on inhibition of the mutagenic action of 2-aminoanthracene on Salmonella typhimurium (T-98). All of these compounds were toxic rather than antimutagenic or desmutagenic. Bakuchiol [17], a known prenylated phenolic terpene, was also isolated; its activity was not due to toxicity. Biochanin A [4], a known isoflavone, was similarly isolated from Cicer arientinum and was active and nontoxic. Some of the above flavonoids were studied for inhibition of the mutagenicity of several different mutagens with results depending upon the structure of the flavonoid and the mutagen.