Apiaceae furanocoumarin

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... 

Hadacek F, Mueller C, Werner A, Greger H, Proksch P, Analysis, isolation and insecticidal activity of linear furanocoumarins and other coumarin derivatives from Peuxedanum (Apiaceae Apioideae),/ Ecol 20 2035—2054, 1994. 

Stanjek, V. and Boland, W. (1998) Biosynthesis of angular furanocoumarins mechanism and stereochemistry of the oxidative dealkylation of columbianetin to an-gelicin in Heracleum mantegazzianum (Apiaceae). Helv. Chim. Acta, 81,1596-607. 

Coumarins and furanocoumarins, which serve as potent defence compounds in the Apiaceae and Rutaceae, occur in a few, mostly unrelated, species. Only in the genus Psoralea do they have a wide distribution. An-thraquinones, which are potent Na+, K+-ATPase inhibitors and strong purgatives, occur widely in the genus Cassia (Senna), but otherwise only occasionally in Andira and Abrus. 

Furanocoumarins are formed when furor ring is joined with coumarins. The plants of Rutaceae, Leguminosae and Apiaceae are rich sources of furanocoumarins. Depending upon the structure, the furanocoumarins are divided into linear and angular types. Furanocoumarin containing preparations are used externally as well as internally for treatment of leucoderma, psoriasis and skin carcinoma. 

Apiaceae roots are generally characterized by a high number of structurally similar furanocoumarins (fcs). All fcs show quenching in UV-254nm and blue, violet or brown fluorescence in UV-365 nm. 

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

Peroutka, R., V. Schulzova, P. Botek, and J. Hajslova. 2007. Analysis of furanocoumarins in vegetables (Apiaceae) and citrus fmits (Rutaceae). /. Sci. Food Agric. 87(11) 2152-2163. 

Although simple coumarins are found in many plant families, the distribution of furanocoumarins is restricted. Furanocoumarins have been reported from the Apiaceae (Umbelli-ferae), Asteraceae (Compositae), Moraceae (Brosimum, Dorstenia, Fatoua, and Ficus), Pittosporaceae, Rosaceae, Rutaceae, Solanaceae, and Thymelaeaceae (Bilia et al, 1992,1993 Murray etal., 1982 Swain and Downum, 1990). Certain precursors to this group of compounds are found in the Cneoraceae (Murray, 1978). 

Insect herbivory is an important selective force in the ecology and evolution of plants. The linear furanocoumarin, xanthotoxin (19), found in many plants of die Apiaceae and Rutaceae is toxic to the larvae of Spodoptera eridania, a generalist insect herbivore. This toxicity was shown to be increased in the presence of UV light. 

Species of Apiaceae that possess furanocoumarins typically are those of open habitats (swamps or thickets) or disturbed areas such as roadsides or old fields. This is in keeping with a role of light in the effects of these plants on herbivores (Berenbaum, 1981b). 

Butterflies of the genus Papilio (Lepidoptera) often are associated with members of the Apiaceae. Xanthotoxin (19), a linear furanocoumarin, occurs in many plants of the Apiaceae. This compound is not appreciably toxic to the larvae of Papilio polyxenes which normally feed on umbelliferous plants. Most of these insects feed only on plants that have linear furanocoumarins and, in general, do not consume plants that make angular furanocoumarins. Angelicin (30)... 

Fig. 9.6), an angular furanocoumarin found in only a few relatively advanced tribes of the Apiaceae, reduces both growth rate and fecundity in this insect. This finding suggested that, in this instance, plants that produce angular furanocoumarins may be favored over those that make only linear furanocoumarins (Berenbaum, 1983). 

Plants that contain furanocoumarins have been implicated in several problems of livestock poisoning. For example, in the western United States, Cymopterus watsoni (Apiaceae) has been involved in the poisoning of sheep (Ivie, 1978). Starved individuals of the rock hyrax, Procavia capensis syriaca, which is notable for its ability to consume toxic plants, were killed when they consumed shoots of Pitur-anthos triadiatus (Apiaceae), which contain furanocoumar-... 

Khellin (33), an antispasmodic drug that comprises approximately 1% of the dry weight of plants of Ammi visnaga (Apiaceae), has a pyrone structure reminiscent of that of many linear furanocoumarins (Fig. 9.6). This compound acts directly on smooth muscle, is a bronchial dilator, and is used in the treatment of asthma (Sneader, 1985). 

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

Coumarins are widely distributed in the plant kingdom, especially in the families Apiaceae, Rutaceae, Leguminosae, and Compositae [30,31]. Generally, the highest level of coumarins is found in the fruits, followed by roots, stems, and leaves. In Table 1 are shown the main linear furanocoumarins present in the plant kingdom and vegetable sources. On the other hand, in Table 2 are shown the main angular furanocoumarins and their presence in different plants. 

---