Coumarins scopoletin

Lactones. Physiologically active lactones such as parasorbic acid, coumarin, scopoletin, and protoanemonin occur in many plant families (Figure 2). The lactones may perform a regulatory function in the plant, and have been shown to inhibit germination and to repress root growth [reviewed in detail by Hemberg 61), Evenari 36,37), and Borner 12)]. 

Tenerife and La Palma, revealed the existence of luteolin and an array of simple phenolic derivatives as well as three known phytosterols, B-amyrin, sitosterol, and stigmasterol. The phenols identified comprised a set of phenylpropanoids myristicin [566] (see Fig. 6.16 for structures 566-573), methyleugenol [567], todadiol [568], todatriol [569], crocatone [570], elemicin [571], apiole [572], and the coumarin scopoletin [573]. The occurrence of these compounds is recorded in Table 6.5. The differences between the two profiles were taken by Gonzalez and his co-workers... 

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. 

N.A. Picrasma exeelsa (Sw.) Planch. Quassinoid (quassin), alkaloids, coumarin (scopoletin), vitamin B,.09 Strengthen digestive systems, increase bile flow, secretion of salivary juices, and stomach acid production. 

The continuous search for germination inductors to control parasitic weeds has led to testing a great variety of natural products. Some positive results have been obtained for Striga with compounds such as the coumarin scopoletin (11), the... 

Olson, M.M. and Roseland, C.R., Induction of the coumarins scopoletin and ayapin in sunflower by insectfeeding stress and effects of coumarins on the feeding of sunflower beetle (Coleoptera Chrysomel-idae), Environ. Entomol., 20, 1166-1172, 1991. 

In the banana Musa acuminata (Musaceae), a series of novel phenalenone-type compounds, including irenolone and 2-(4 -hydroxyphenyl)-l,8-naphthalenedicarboxylic anhydride, have been identified (Figure 29) 279,280 In the Compositae, acetophenone derivatives in yacon (Polymnia sonchifolia)114 and the coumarins scopoletin and ayapin in sunflower (Helianthus annuus f81 have been reported (Figure 29). 

Coumarins scopoletin, and -7-0-glucoside Alkaloids hyo.scyamine (see Fig. 27,28 Chap. 1 AUcaloid Drugs)... 

The Solanaceae root extracts (1-3) are characterized not only by the alkaloids hyos-cyamine and scopolamine (see Chapter 1. Figs. 27, 28), but also by the coumarins scopoletin (Tl) and the scopoletin-7-O-glucoiiide ( scopolin"). The alkaloid content dominates in BeJladonnae radix, while Scopoliae radix has a high coumarin content. 

Other secondary metabolites isolated from Hedyotis (Table 8) include coumarins, scopoletin and fraxin (77-78) from H. dichotoma [33] and arbutin (79), a hydroquinone monoglucoside, from H. herbacea [7],... 

The coumarins, scopoletin and aesculetin, were present in celery roots in amounts smaller than 0.5 mg/kg f.w. [51]. The coumarin concentration was five to ten times higher in the peel of the tuber than in the edible portion. When celery tubers were coated with pectin gels and stored for 6 months at 4°C and 95% relative humidity, the furanocoumarin concentration increased considerably [53]. 

The coumarins, scopoletin and scoparone, are also found in some cultivars. 

Sweet potato also contains the coumarins scopoletin (3, / =H), aesculetin (3, i =OH), and umbelliferone (3, J =OMe) compounds, which have anticoagulation properties and are postulated to inhibit HIV replication (Weiss and Finkelmann, 2000). The sweet potato could be considered as an excellent novel source of natural health-promoting compounds, such as anthocyanins, for the functional food market. Ultimately, this could increase utilization and demand for the crop by consumers, and the food industry. 

Phytochemistry The aboveground parts contain lactones (artemisinin and arteannuin), coumarins (scopoletin), 0.12-0.65 % essential oil, tannins, alkaloids, resins, sugars, and vitamin C. Maximum essential oil content was observed during the flowering period. Plants collected near Bishkek (Kyrgyzstan) contained 0.21 % essential oil and 2.44 % tannins (Khahnatov 1964 Khodzhimatov 1989). 

Phytochemistry The whole plant contains alkaloids, with the main alkaloids being hyoscyamine, atropine, and scopolamine (Khalmatov et al. 1984). The leaves and stems also contain coumarins (scopoletin, esculetin, and esculin), tannins, essential oils, and carotene. Seeds contain up to 25 % fatty oil, containing linoleic, oleic, palmatic, stearic, and lignoceric acids (Khodzhimatov 1989). 

Minor constituents - Coumarins (scopoletin, isoscopoletin, trans-O-coumaric acid), glycosides, polyacetylenes, steroids/sterols, sesquiterpene, ketones (moxartenolide, moxartenone), fatty acids (13-0X0-9 (Z),ll (E)-octadecadienoic acid 13-oxo-9 (E),ll (E)-octadecadienoic acid 9-oxo-lO (E),12 (E)-octadecadienoic acid) [5.10.15,18,21]... 

Miscellaneous constituents of the plant include inulobiose (an oligofructoside), coumarins (scopoletin, umbelliferone), phenolic acids, flavonoids, amino acids, tannins (4.0-7.7%), ° lignans (3,7-dioxabicy-clo[3,3,0]-octanes), pipecolic acid, and sterols, including an antipyretic sterol (24 -ethylcholesta-7,22-dien-3P-ol). ... 

Viburnum prunifolium contains coumarins (scopoletin, scopolin, aesculetin), alkaloids, P-sitosterin, arbutin, triterpenes (a- and P-amyrin, ursolic acid, oleanolic acid), amento-flavone, and iridoid glucosides Valeriana type)." Other constituents include malic, citric, oxalic, and valeric acids) tannin bitter resin and others (merck). 1 -Methyl-2,3-dibutyl hemi-mellitate was isolated from the stem bark. ... 

Other constituents present include the coumarin scopoletin (also called gelsemic acid and P-methylesculetin), an iridoid compound, volatile oil (0.5%), pregnane-type steroids (12-P-hydroxypregna-4,16-diene-3,20-dione and 12-(3-hydroxy-5-a-pregn-16-ene-3,20-dione), fatty acids (palmitic, stearic, oleic, and linoleic acids), n-pentatria-contane, and tannins (karrer list and hOrhammer). 

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