Bitter sesquiterpene lactones from chicory roots

Beek, van T.A.; Maas, P.; King, Bonnie M.; Leclercq, E.; Voragen, A.G.J.; Groot, de Ae.

doi:10.1021/jf00094a026

Cited by 118 publications

(97 citation statements)

References 10 publications

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“…the 11(S),13-stereoisomer of dihydrocostunolide. This compound has the same stereochemistry that is present in the 11,13-dihydro sesquiterpene lactones (4-6 and 8) of chicory (Seto et al, 1988;van Beek et al, 1990). This notwithstanding, some plant species do contain C 11 -epimers, like achillin, which is the 11(R)-epimer of leucodin (Martínez et al, 1988;Ho et al, 1998), indicating that a stereoselective enzyme that synthesizes these C 11 -epimers should also exist.…”

Section: Germacranolides Guaianolides and Eudesmanolidesmentioning

confidence: 91%

“…Interestingly, leucodin is only one hydroxylation away from 11(S),13-dihydro-8-deoxylactucin (5; Fig. 10), a minor sesquiterpene lactone of chicory (van Beek et al, 1990). The conversion of (ϩ)-costunolide into leucodin most likely involves more than one enzyme, but whether leucodin originates from 11(S),13-dihydrocostunolide (17) was not investigated.…”

Section: Germacranolides Guaianolides and Eudesmanolidesmentioning

confidence: 99%

“…Notably,leucodin (19) is only one hydroxylation away from 11(S),13-dihydro-8-deoxylactucin (5), a minor sesquiterpene lactone of chicory. ever, in the major sesquiterpene lactones of chicory, the guaianolides 1 and 3 (van Beek et al, 1990), the C 11 -C 13 bond is unsaturated and these compounds are most likely formed from (ϩ)-costunolide without the intermediacy of 11(S),13-dihydrocostunolide. Perhaps some of these sesquiterpene lactones were already formed during the experiments, but unfortunately these compounds cannot be detected in GC-MS measurement because of their polarity and reduced volatility.…”

Section: Germacranolides Guaianolides and Eudesmanolidesmentioning

confidence: 99%

“…Also the sesquiterpene lactones of chicory belong either to the guaianolides, eudesmanolides, or germacranolides ( Fig. 1; Seto et al, 1988;van Beek et al, 1990). (ϩ)-Costunolide (Fig.…”

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confidence: 99%

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Biosynthesis of Costunolide, Dihydrocostunolide, and Leucodin. Demonstration of Cytochrome P450-Catalyzed Formation of the Lactone Ring Present in Sesquiterpene Lactones of Chicory

et al. 2002

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Chicory (Cichorium intybus) is known to contain guaianolides, eudesmanolides, and germacranolides. These sesquiterpene lactones are postulated to originate from a common germacranolide, namely (ϩ)-costunolide. Whereas a pathway for the formation of germacra-1(10),4,11(13)-trien-12-oic acid from farnesyl diphosphate had previously been established, we now report the isolation of an enzyme activity from chicory roots that converts the germacrene acid into (ϩ)-costunolide. This (ϩ)-costunolide synthase catalyzes the last step in the formation of the lactone ring present in sesquiterpene lactones and is dependent on NADPH and molecular oxygen. Incubation of the germacrene acid in the presence of 18 O 2 resulted in the incorporation of one atom of 18 O into (ϩ)-costunolide. The label was situated at the ring oxygen atom. Hence, formation of the lactone ring most likely occurs via C 6 -hydroxylation of the germacrene acid and subsequent attack of this hydroxyl group at the C 12 -atom of the carboxyl group. Blue light-reversible CO inhibition and experiments with cytochrome P450 inhibitors demonstrated that the (ϩ)-costunolide synthase is a cytochrome P450 enzyme. In addition, enzymatic conversion of (ϩ)-costunolide into 11(S),13-dihydrocostunolide and leucodin, a guaianolide, was detected. The first-mentioned reaction involves an enoate reductase, whereas the formation of leucodin from (ϩ)-costunolide probably involves more than one enzyme, including a cytochrome P450 enzyme.Chicory (Cichorium intybus), also known as French endive, Witloof, and succory is probably a native of Europe and Asia. At present, this composite plant is mainly cultivated for its roots (C. intybus var sativum) that contain high amounts of inulin (a Fru polymer) or for its sprouts (C. intybus var foliosum Hegi) that are a well-known salad crop (Vogel et al., 1994;Kruistum, 1997;Westerdijk, 2000). The white sprouts, which are grown in the dark, have a slightly bitter taste that is associated with the presence of sesquiterpene lactones. These compounds occur throughout the plant, though at highest levels in the roots (0.42% dry weight), and act as deterrents toward insects (Rees and Harborne, 1985;Price et al., 1990).Sesquiterpene lactones are a major class of plant secondary metabolites that are mainly found in the Asteraceae but also occur infrequently in other high plant families and lower plants (Seigler, 1998). The majority of the more than 4,000 known different structures has a guaiane, eudesmane, or germacrane framework. Also the sesquiterpene lactones of chicory belong either to the guaianolides, eudesmanolides, or germacranolides ( Fig. 1; Seto et al., 1988;van Beek et al., 1990). (ϩ)-Costunolide (Fig. 2, 15) is structurally the simplest of all germacranolides and is generally accepted as the parent compound of the three mentioned types of sesquiterpene lactones (Geissman, 1973; Fischer et al., 1979;Seaman, 1982; Fischer, 1990).Our studies with chicory roots have made it apparent that its sesquiterpene lactones are derived from (ϩ)-germa...

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Section: Germacranolides Guaianolides and Eudesmanolidesmentioning

confidence: 91%

Section: Germacranolides Guaianolides and Eudesmanolidesmentioning

confidence: 99%

Section: Germacranolides Guaianolides and Eudesmanolidesmentioning

confidence: 99%

“…Also the sesquiterpene lactones of chicory belong either to the guaianolides, eudesmanolides, or germacranolides ( Fig. 1; Seto et al, 1988;van Beek et al, 1990). (ϩ)-Costunolide (Fig.…”

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confidence: 99%

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Biosynthesis of Costunolide, Dihydrocostunolide, and Leucodin. Demonstration of Cytochrome P450-Catalyzed Formation of the Lactone Ring Present in Sesquiterpene Lactones of Chicory

et al. 2002

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“…The leaves are rich source of vitamins, vitamin-A, vitamin-C, vitamin-K, niacin & folate, minerals particularly calcium, iron, phosphrous, sodium, potassium (USDA Nutrient database). The latex from Lactuca sativa contain 15 oxalyl and 8 sulfate conjugates of the guaianolide sesquiterpene lactones, lactucin, deoxylactucin and lactucopicrin 14,15 . The guaianolide sesquiterpene lactones (Fig.…”

Section: Chemical Composition and Active Compoundsmentioning

confidence: 99%

Lettuce: a promising leafy vegetable with functional properties

Harsha¹,

Mallesha²,

Sharma³

2017

Def. Life. Sc. Jl.

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Lactuca sativa (lettuce) belongs to Asteraceae family important leafy vegetable known for its medicinal properties. The lettuce is a food that should not lack in our meals, we should keep in mind that its low fat and carbohydrate contents and its high contents of water, it provides caloric power of only 13 Kcal /100 gm are very appropriate for weight loss diets. It is rich in minerals, especially potassium that is very necessary to maintain appropriate levels of liquids in the body, together with calcium and phosphorus makes it especially for the correct well being of the bones. It contains selenium, an antioxidant that has a medicinal property in prevention of certain type of cancers, colon, prostrate and lungs. It contains many necessary amino acids for the formation of the proteins, alanine, and necessary for the construction of muscular and nervous tissues, glycine for the correct operation of immunological system. The most of therapeutic properties of this plant is due to sesquiterpene lactones-lactucin, lactucopicrin the most bioactive compound of Lactuca sativa. This review mainly focuses on the pharmacological action of the Lettuce and active constituents for the wide spectrum biological properties, such as anti-oxidant, anti-inflammatory, anti-microbial, analgesic, neuroprotective and sedative properties, etc. Since Lettuce has medicinal therapeutic potential its usage in dietary supplementation can be exploited. Lettuce has also acquired a folk reputation. More clinical studies are needed to further asses the efficiency and safety in therapeutic application.

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Biochemistry of Vegetables: Major Classes of Primary (Carbohydrates, Amino Acids, Fatty Acids, Vitamins, and Organic Acids) and Secondary Metabolites (Terpenoids, Phenolics, Alkaloids, and Sulfur‐Containing Compounds) in Vegetables

Hounsome¹,

Hounsome²

2010

Handbook of Vegetables and Vegetable Processing

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Bitter sesquiterpene lactones from chicory roots

Cited by 118 publications

References 10 publications

Biosynthesis of Costunolide, Dihydrocostunolide, and Leucodin. Demonstration of Cytochrome P450-Catalyzed Formation of the Lactone Ring Present in Sesquiterpene Lactones of Chicory

Biosynthesis of Costunolide, Dihydrocostunolide, and Leucodin. Demonstration of Cytochrome P450-Catalyzed Formation of the Lactone Ring Present in Sesquiterpene Lactones of Chicory

Lettuce: a promising leafy vegetable with functional properties

Biochemistry of Vegetables: Major Classes of Primary (Carbohydrates, Amino Acids, Fatty Acids, Vitamins, and Organic Acids) and Secondary Metabolites (Terpenoids, Phenolics, Alkaloids, and Sulfur‐Containing Compounds) in Vegetables

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