Coumarins glucoside

Elgamal, M.H.A., Shalaby, N.M.M., Duddeck, H. and Hiegemann, M. (1993) Coumarins and coumarin glucosides from the fruits of Ammi majus. Phytochemistry, 34, 819-23. 

Extraction of the dried and well ground plant material was carried out with hot ethanol. The extract was concentrated to a small volume and the deposited solid (a mixture of the coumarin glucosides 1 and 3) filtered. The mother liquor was concentrated to obtain the total ethanol extract 1 (TE1). In some cases the ethanolic extract was concentrated without removal of the deposited solid to give the total ethanol extract 2 (TE2). TE1 and TE2 were further used in the biological studies and for isolation of pure components. 

Kuwajima, H., Morita, M., Takaishi, K., Inoue, K., Fujita, T., He, Z.D., Yang, C.R. Secoiridoid, coumarin and secoiridoid-coumarin glucosides from Fraxinus chinensis. Phytochemistry 31(4), 1277-1280 (1992)... 

The AChE inhibitory properties of the coumarins scopoletin (75) and scopolin (76) were discovered by an interesting in silico approach. A model 3-dimensional pharmacophore was constructed, using a database of known inhibitors and their interaction with the AChE from Torpedo californica. The model was then used to predict likely inhibitors from a large database of those whose molecular coordinates were known. (75) and (76) were predicted and then isolated from Scopolia carniolica and tested in the Ellman assay. Results showed that (75) was much more active than the glucoside (76) but it was 2.5 orders of magnitude weaker than galantamine. Scopoletin also showed activity in vivo when given to rats. 

OE072 Tsukamoto, H., S. Hisada, and S. OE084 Nishibe. Coumarin and secoiridoid glucosides from bark of Olea europaea and Olea capensis. Chem Pharm Bull 1985 33(1) 396-399. 

A broad spectrum of coumarin derivatives (present both in the free state and as glucosides) have also been found in many plants to date at least 1300 have been identified, principally as secondary metabolites in green plants (Hoult Payd, 1996). 

The biosynthesis of coumarins begins with traw5 -4-cinnamic acid, which is oxidized to ort/io-coumaric acid (2-hydroxy cinnamic acid) followed by formation of the glucoside. This glucoside isomerizes to the corresponding cA-compound, which finally through ring closure forms... 

Achillea alpina L. A. millefolium L. Shi Cao (Siberian yarrow) (aerial part) Alkaloids, essential oils, achillin, flavonoides, betonicine, achilleine, d-camphor, oxalic acids, ether oils, hydroxycinnamic acids, hydrocyanic acids, hydroxybenzoic acids, anthocyanidines, anthraquinones, phytosterines, carotene, coumarins, monoterpene, sesquiterpene glucosides, desacetylmatricarin.33-222-450 Antibacterial, treat menopause, abdominal pain, acute intestinal disorder, wound infection, snakebite. 

Hierochloe odorata (L.) Beauv. Mao Xian (root, flower head) Coumarin, coumarinic acid-P-glucoside.48 Relieve internal bleeding, kidney infection. 

Polygonum bistorta L. Cao He Che (Snakeweed, bistort) (stem, root) Iodine, oxalic acids, coumarins, hydroxycinnamic acids, ether oil, hydroxybenzoic acids, hydrocyanic acids, anthocyanidines, carotenes, anthraquinones, phytosterines, monoterpene, sesquiterpene glucoside, caffeic acid, quercimeritrin, avicularin, gallic acid, protocatechuic acid 50.221.222,223,224 Diuretic, laxative, hemostatic, antifebrile. 

Taraxacum officinale G. H. Weber ex Wigg. Western Pu Gong Ying (Dandelion) (root) Inulin, essential oils, choline, hydroxycinnamic acids, carotenes, ether oils, monoterpene, oxalic acids, hydrocyanic acids, sesquiterpene glucosides, flavonoids, hydroxybenzoic acid, coumarins, anthocyanidines, anthraquinones, phytosterines, squalene, cerylic alcohol, arabinose, vitamins , , C.88-222-450 Sudorific, stomachic, tonic, a remedy for sores, boils, ulcers, abscesses, snakebites. 

Phloroglucinol (42) is a colorless and odorless solid which is only sparingly soluble in cold water (82). It was discovered in 1855 in the hydrolysis products of the glucoside phloretin, which was obtained from the bark of fruit trees. Phloroglucinol occurs in many other natural products in the form of derivatives such as flavones, catechins, coumarin derivatives, anthocyanidins, xanthins, and glucosides. 

Either the aglycone resulting from the action of a P-glucosidase or the glucoside, or possibly both, undergo cis-trans isomerization under influence of UV-light or possibly mediated by a dimethylallyl transferase. The last step of the biosynthetic pathway is an intramolecular esterification reaction, which can occur spontaneously, to yield coumarin (3.96). The enzymes that involved in these reactions have not been purified. 

Coumarins and their glucosides are ubiquitous and widely distributed secondary metabolites in the plant kingdom. Among them, scopoletin (54), umbelliferone (55), and esculetin (56) are representative allelochemicals. They exhibit various biological activities. In general, these compounds inhibit growth of plants but some display growth promotion at lower concentrations.36... 

---