Bitterness sesquiterpene lactone

Dekraker, J.W., Franssen, M.C.R., Degroot, A., Konig, W.A. and Bouwmeester, H.J. (1998) (-F)-Germacrene A biosynthesis the committed step in the biosynthesis of bitter sesquiterpene lactones in chicory. Plant Physiol., 117,1381-92. 

Main components 0.5-1.3% essential oil, bitter sesquiterpene lactones (artabsin, ab-sinthin, anabsinthin), flavonoids for further constituents see [300[. 

Bitter sesquiterpene lactones in the root increase bile secretion in rats by more than 40% and increases gastric secretion (escop 3). 

Effects of Sesquiterpene Lactones on Seed Germination. Sesquiterpene lactones are common constituents of the Asteraceae but are also found in other angiosperm families and in certain liverworts (31,32). These highly bitter substances exhibit a wide spectrum of biological activities (J 3) which include cytotoxicity, anti-tumor, anti-microbial, insecticidal (34) and molluscicidal (35) properties. Furthermore, they are known causes for livestock poisoning and contact dermatitis in humans (33). Structure-activity relationship studies on sesquiterpene lactones have demonstrated that biological activity frequently depend on the presence of the cr... 

Main actives Sesquiterpene lactones, which are bitter flavoured, triterpenes, steroids, flavonoids, mucilages and an inulin content that varies from 2 to 40% in the autumn. Benefits The bitter components were used to promote the flow of digestive juices in the upper intestinal tract. 

Main components Bitter constituents like the sesquiterpene lactone cnicin (0.2-0.7%) and lactonic lignans [31 [ as well as polyacetylenes and traces of essential oil. 

Brockhoff A, Behrens M, Massarotti A, Appendino G, Meyerhof W (2007) Broad tuning of the human bitter taste receptor hTAS2R46 to various sesquiterpene lactones, clerodane and lab-dane diterpenoids, strychnine, and denatonium. J Agric Food Chem 55 6236-6243 Brouwer JN, Hellekant G, Kasahara Y, van der Wei H, Zotterman Y (1973) Electrophysiological study of the gustatory effects of the sweet proteins monellin and thaumatin in monkey, guinea pig and rat. Acta Physiol Scand 89 550-557... 

The bitter substances include the sesquiterpene lactones millefolide and... 

Phytochemistry The plant contains alkaloids, flavonoids, sesquiterpene lactones, essential oils, vitamins C and K, resin, carotene, phytoncides, and bitter and astringent substances (Plant Resources of the USSR 1993 Glasl et al. 2001). 

Phytochemistry The plant contains traces of saponins, tannins and bitter substances, 4 % glycoalkaloids, 0.06 % essential oils and sesquiterpene lactones (Ogolevitz 1951 Stevens et al. 1990). The main constituent of volatile oil isolated from the aboveground parts was caryophyllene oxide (36.6 % Norouzi-Arasi et al. 2006). 

Phytochemistry Leaves contain alkaloids, glycosides, bitter substances, sesquiterpene lactones (arctiopicrin and onopor-dopicrin), vitamin C and K, resins, titratable acids, sugars, tannins, terpenoids (taraxasteryl acetate), etc. Seeds contain alkaloids, acetates of lupeol and amyrin, and drying fatty oil (Khalmatov et al. 1984 Ul chenko et al. 1993 Khalilova etal.2004). 

Sesquiterpene lactones from Parthenium species were strongly inhibitory to growth of larvae of Helicoverpa zea and Spodoptera exigua (Isman and Rodriguez, 1983). Tenu-lin (111), the major sesquiterpene lactone of Helenium amarum, imparts a bitter taste to milk and is toxic to livestock. Helenalin (112) from Helenium microcephalum is toxic to several mammalian species in oral doses as low as 85 fjLg/kg. Hymenoxys odorata, from which a toxin, hymenovin... 

Sesquiterpene lactones have been isolated from all plant parts. However, most commonly they are obtained from glandular trichomes in leaves. They are bitter... 

Many sesquiterpenes contain a pentacyclic lactone group and are therefore referred to as sesquiterpene lactones. These compounds occur abundantly in the family Asteraceae. Because of their bitter taste sesquiterpene lactones presumably serve as feeding deterrents of herbivores (Heinrich et al., 1998). Pharmacologically active sesquiterpene lactones often show anti-inflammatory effects due to inhibition of the transcription factor NF-kB that mediates immunological responses and inflammation (LyB et al., 1998). Sesquiterpenes with such activities occur, for example, in chamomile Matricaria recutita), one ofthe most popular medicinal plants. Antimigraine action of some sesquiterpene lactones, e.g., par-thenolide from feverfew (Tanacetum parthenium), is mediated by inhibition of platelet aggregation... 

Plants of the family Asteraceae, which are used as a spice and for the production of bitter liqueurs and vermouths (aroma-tised fortified wine flavoured with various botanicals), contain sesquiterpenic lactones derived from guaiane (8-226), eudesmane (8-250) and germacrane (8-251). Eudesmane (also known as selinene) has the systematic name (JS,4aJ ,7 R,8aS)-7-isopropyl-l,4a-dimethyldecahydronaphthalene, germacrane is (lJ ,4S,7S)-4-isopropyl-l,7-dimethylcyclodecane. 

The main bitter component of wormwood Artemisia absinthium) is a dimeric sesquiterpenic lactone absinthin (8-252), which is produced by intramolecular cycloaddition (Diels-Alder reaction) probably of two molecules of astabisin (8-253), which is derived from guaiane. In wormwood extracts, absinthin is transformed into isomeric anabsinthin (8-254). The bitter taste of mugwort (A. vulgaris) is derived primarily from the related compounds estafiatin (8-255) and balchanin (8-256), which are... 

The diterpenes are discussed in connection with the mono- and sesquiterpene derivatives with which they are closely related according to modern ideas of biosynthesis. Brieskorn s team [24, 24 a] has studied the bitter tasting picrosalvin in Salvia species. It is a diterpene-o-diphenol lactone [24 a] which occurs also in other Labiatae. Nicholas [180] has worked likewise on Salvia sclarea and utilised successfully two-dimensional TLC on sihea gel G layers. He used ethyl acetate as solvent and was able to justify the hypothesis about the incorporation of into sclareol. 

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