Viguiera quinqueradiata

Natural methylated flavan-3-ols are extremely rare and it has only been in the past few years that most examples have been found. The first of these compounds to be reported was 4 -0-methylepigallocatechin, a compound with interesting muscle-relaxant properties (74, 182, 375). Since then, 3 -0-methylepicatechin from Symplocus (356), a 4,7,3 - (or 4 )-tri-0-methylepicatechin and 5,7-di-O-methyl-3, 4 -methylenedioxyepicatechin from Cinnamomum cassia (256) have been reported. The most recent example is the 5,7,4 -tri-0-methylcatechin, obtained from Viguiera quinqueradiata (71). Prenylated flavan-3-ols are also rare with broussinol, l,3 -prenyl-3,7,4 -trihydroxyflavan, only recently having been reported from Broussonetia papyrifera in Fusarium solaniAnkcted bark (348). This compound is a true phytoalexin, for, this and related compounds do not occur in healthy tissues. 

Delgado, G., L. Alvarez, and A. Romo de Vivar Terpenoids and a flavan-3-ol from Viguiera quinqueradiata. Phytochem. 23, 675 (1984). 

---