Furanocoumarins prenylated

Stanjek V, Piel J, Boland W (1999) Biosynthesis of furanocoumarins melvalonate-independent prenylation of umbelliferone in Apium graveolens (Apiaceae). Phytochemistry 50 1141-1146 Steinberg PD (1992) Geographical variation in the interaction between marine herbivores and brown algal secondary metabolites. In Paul V (ed) Ecological roles of marine natural products. Comstock, Ithaca, pp 51-92... 

The furanocoumarins xanthotoxin (77) and isopimpinellim (78) from roots of A. acutiloba displayed significant AChE inhibitory activity with IC50 values of 0.58 xM and 0.32 xM respectively." Prenylated coumarins itom. Angelica spp. had only weak activity, with decursinol (79) giving the highest activity (IC50 value 28 xM)." ... 

Abegaz, B.M. et al., Prenylated flavonoids, monoterpenoid furanocoumarins and other constituents from the twigs of Dorstenia elliptica (Moraceae), Phytochemistry, 65, 221, 2004. 

Hydroxylation of p-coumaric acid, followed by photocatalyzed isomerization of the double bond and lactonization, affords 7-hydroxy coumarin (umbel-liferone). Prenylation at the 6-position, epoxidation, cyclization, and a retro-aldol reaction afford the furanocoumarins (Fig. 14) some (psoralen, bergapten)... 

Volker, S., P. Joem, and W. Boland (1999). Biosynthesis of furanocoumarins Mevalonate independent prenylation of umbelliferone in Apiunt graveolens (Apiaceae) Phytochemistry SO, 1141-1145. 

Angular furanocoumarins are derived by prenylation at the 8-position of umbelliferone followed by cyclization via similar intermediates, although experimental evidence is not as good as for linear furanocoumarin biosynthesis. Columbi-anetin (28) (derived by 8-prenylation) is involved in the biosynthesis of angelicin and derived angular furanocoumarins (Fig. 9.3). 

Many quinolone alkaloids are subject to prenylation and give rise to the furoquinoline or pyranoquinoline alkaloids. The furan rings of furoquinoline alkaloids arise by a similar process to thos of furanocoumarins that have been previously discussed (Fig. 31.8). see also Chapter 9) (Geissman and Crout, 1969 Grundon, 1979, 1983). 

Stanjek, V., Piel, J. and Boland, W. (1999b) Biosynthesis of furanocoumarins mevalonate-independent prenylation of umbeUiferone in Apium graveolens (Apiaceae). Phytochemistry, 50, 1141-1145. 

Umbelliferone is considered the precursor of furanocoumarins [16]. It is first prenylated in the 6- (for linear furanocoumarins) or 8-position (for angular furanocoumarins) to yield demethylsuberosin and osthenol, respectively. Dimethy-lallyl diphosphate is required for the 6-prenylation [17]. Demethylsuberosin is... 

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