Apiaceae coumarins

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. 

Coumarin 162 (Structure 4.49) is a naturally occurring lactone in crystal form found in hay and tonka beans. It is one of the most used fragrance materials and is responsible for spicy green notes. Dihydrocoumarine 163 is also present in various essential oils with a characteristic sweet herbal odour. Umbellif-erone 164, scopoletin 165, bergaptene 166 and coumarin are found in Rutaceae, Apiaceae, Lamiaceae and Asteraceae oils. Nepetalactones 167 are confined to the oils of Nepeta species [1,3, 21-23, 63]. 

Coumarins occur abundantly in various plant families, e.g. Apiaceae, Asteraceae, Fabaceae, Lamiaceae, Moraceae, Poaceae, Rutaceae and Sola-naceae. However, the Apiaceae alt. Umbelliferae) and the Rutaceae are the two most important coumarin-producing plant families. 

The dried ripe fruits of Ammi visnaga (Umbelliferae/Apiaceae) have a long history of use in the Middle East as an antispasmodic and for the treatment of angina pectoris. The drug contains small amounts of coumarin derivatives, e.g. visnadin (Figure 3.40) (compare Ammi majus, a rich source of furocoumarins, page 146), but the major constituents (2-4%) are... 

Coumarins are widely distributed in plants, and are commonly found in families such as the Umbelliferae/Apiaceae and Rutaceae, both in the free form and as glycosides. Coumarin itself is... 

Umbelliferone (= Dichrin A Hydrangin 7-Hydroxycoumarin Skimmetin) (coumarin) Terpene Artemisia capillari (Asteraceae), Ammi majus, Apium, Ferula, Heracleum, Pimpinella spp. (Apiaceae), Aegk marmelos, Citrus grandis (Rutaceae), Hydrangea paniculata (Saxifragaceae), Atropa belladonna (Solanaceae) [root] AR (bovine lens) (30) 14.5t... 

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. 

Hydroxycoumarins represents another group of coumarins, which are widely distributed in Apiaceae and Gramineae. 

Simple coumarins (lactones of phenylpropanoic acids with a 2//-l-benzopyran-2-one nucleus) are widespread in plants the four most widely distributed coumarins are coumarin (1), umbelliferone (2), esculetin (aesculetin) (3), and scopo-letin (4) (Fig. 9.1) (Brown, 1979). Coumarins have not been reported from algae or mosses, although umbelliferone has been reported from a liverwort (Berenbaum, 1991). Coumarin is both the name of a specific compound and the name of a group of structurally related compounds. Variations of these basic coumarin structures are encountered commonly (especially in the Apiaceae) and at least 300 simple coumarins and a total of at least 1000 naturally occurring coumarins are known (Berenbaum, 1991 Brown, 1986, personal communication). Many coumarins, such as xanthyletin (5) and seselin (6), are prenylated. 

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). 

A mixture of volatiles from carrot Daucus carota, Apiaceae) is responsible for oviposition by females of the carrot fly Psila rosae). Among these are the phenylpropanoids. E-methyleugenol, -asarone, a prenylated coumarin, osthol (31), bergapten (18), xanthotoxin (19), and an acetylenic compound, falcarindiol (Harbome, 1986). No single component of the mixture is responsible for the behavior of the fly. 

The distribution of sesquiterpene lactones often is referred to as an indication of affinity between the Asteraceae and the Apiaceae (Hegnauer, 1977). These two families share polyacetylenes, coumarins, and flavonoids, as well as other types of compounds. The stereochemical features of the sesquiterpene lactones found in these families provide additional support for the relationship (Holub et al, 1987). 

Murphy, E.M. Nahar, L. Byres, M. Shoeh, M. Siakalima, M. Rahman, M.M. Gray, A.I. Sarker, S.D. Coumarins from the seeds of Angelica sylvestris (Apiaceae) and their distrihution within the genus Angelica. Biochem. Syst. Ecol. 2004, 32, 203-207. 

The distribution of coumarins is widespread. Originally isolated from tonka beans, they are abundant in particular plant families, for example Rubiaceae—Asperula Poaceae—Avena Fabaceae—Medic-ago, Melilotus Rutaceae—Ruta, Citrus spp., Murraya Apiaceae— Angelica, Ammi. 

Asafoetida, one of the most pungent of all spices, is obtained from the rhizomes and roots of the shrub Ferula assa-foetida (Apiaceae), native to the sonthwest Asian region. It is rich in an oleo-gum-resin made np of 6-17% volatile oils, 40-64% resin and 7-25% gum. The volatile oil contains disulfide compounds similar to those in garlic. The resin consists of farnesiferols—sesquiterpenoid coumarins— along with ferulic acid and asaresinatannols (Bradley 1992). 

Origin of Some Central Trivial Names. Some names were chosen according to the discovery of the corresponding compounds such as cinnamic acid [Cinnamomum verum Presl., cinnamon tree (Lauraceae)], coumaric acids/ coumarin [Dipterix odorata (Aubl.) Wu-ld. sub nom. Coumarouna odorata Aubl. (Fabaceae)], caf-feic acid [Coffea arabica L., coffee tree (Rubiaceae)], and ferulic add (Ferula spp., Apiaceae). Quinic acid is named according to its discovery as a constituent of cinchona bark [Cinchona L. spp. (Rubiaceae)] this compound was named according to the German Chinarinde (cinchona bark) - corrupted from quina (Spanish... 

Coumarins are naturally found in many families of plants (Apiaceae, Asteraceae, Fabiaceae, Rosaceae, Rubiaceae, Rutaceae and Solanaceae) and microorganisms. 

An example of coumarins with isoprenoid substituents is osthenol, 7-hydroxy-8-(2-hydroxy-3-methyl-3-en-l-yl)coumarin (10-132), which together with osthol, 7-methoxy-8-(3-methyl-2-en-l-yl)coumarin and auraptenol, 7-methoxy-8-(2-hydroxy-3-methyl-3-en-l-yl)coumarin, occurs in citrus fruits. In common with many other coumarins, it is found in garden angelica Angelica archangelica, Apiaceae) and other plants. 

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