Simple prenylated hydroquinone derivatives from the marine urochordate aplidiumcalifornicum. Natural anticancer and antimutagenic agents.

The structures and syntheses of prenylhydroquinone ($\text{1}$), 6-hydroxy-2,2-dimethylchromeme ($\text{2}$), and prenylquinone ($\text{3}$), which are natural products isolated from the marine colonial tunicate $\text{Aplidium}$$\text{californicum}$, are described. Prenylhydroquinone shows $\text{in}$$\text{vivo}$ activity against P388 lymphocytic leukemia (T/C=138). Both $\text{1}$ and $\text{2}$ significantly inhibit the mutagenic effects of benzo(a)pyrene, aflatoxin B₁ and ultraviolet light on $\text{Salmonella}$$\text{typhimurium}$, and may be cancer protective agents.