Scopoletin glucoside

Watanabe et ah (82) also observed the accumulation of scopoletin glucoside in boron-deficient tobacco leaves. The leaves from boron-deficient plants contained a 20-fold increase in the glucoside compared with normal tobacco plants. Other blue fluorescent compounds accumulating in boron-deficient tissue have also been identified (83). Boron-deficient culture medium used for sunflower stem callus and root tissue culture resulted in less lignification than in normal tissue 41). Recently,... 

Chong, J. et al. (2002) Downregulation of a pathogen-responsive tobacco UDP-Glc phenylpropanoidglucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance. Plant Cell 14, 1093-1107... 

Auxins, scopoletin, hydrocyanic acid, glucosides, glucosides, unidentified ninhydrin-positive compounds, unidentified soluble proteins, reducing compounds, ethanol, glycinebetaine, inositol and myo-inositol-like compounds, Al-induced polypeptides, dihydroquinone, sorgoleone... 

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. 

China Viburnum sargenti Koehne f. glabram Kom. Scopoletin, aesculetin, caffeic acid, citric acid, malic acid, chlorogenic acid, isochlorogenic acid, essential oil, kaempferol-3-glucoside, beta-amyrin, beta-sitosterol, paeonin.48 For blood circulation, swelling, detoxicant, relieve itchiness, arthritis. 

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... 

The whole plant of Swertia japonica Makino (Gentianaceae) is an important bitter stomachic in Japan where it is called "senburi". The plant is also claimed to be effective in the treatment of hepatitis (57). Components of this plant such as the bitter secoiridoids (58-63), phenyl glucosides (64), flavonoids (65) and xanthones (66-68) have been intensively studied mainly by Japanese researchers but, to date, there are few reports on the production of these constituents in vitro. Callus culture produced no bitter principles (secoiridoids) (69, 70), xanthones and flavones but coumarin derivatives, scopoletin and its glucoside were detected (71). 

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

The metlianolic extracts of Abrotani herba (1) and Fabiani herba (2) are characterized by the prominent blue fluorescent coumarin aglycoiie zone at R, 0.95 (scopoletin, isofraxidin and umbelliferone). They are differentiated by the violet-blue fluoresceiit isofraxidin-7-0 and scopoletin-7-O-glucosides in the range of0.4-0.45 and an additional zone at R 0.7 in sample 1 and the scopoletin-7-O-priinveroside at Rf 0.15 in extract 2. 

Treatment with KOH reagent intensifies the fluorescence of the coumarins such as scopoletin at the solvent front and scopoletin-7-O-glucoside at R, 0.45. 

The Hedera helix samples (1,3,5) are characterized by a series of prominent blue fluorescent zones of phenol carboxylic adds and coumarins in the R, range 0.45-0.95 e.g. chlorogenic acid (T2) and scopoletin-7-O-glucoside at R, 0.45-0.5, the... 

Carrots can accumulate, in response to fungal infection, the coumarins 6-methoxymellein and scopoletin alongside several p-hydroxybenzoic acid derivatives [46], In carrot leaves, apigenin 7-glucoside and luteolin 7-glucoside have been detected [47]. 

The major phenolic compound in tobacco roots (Figure 1) is chlorogenic acid (CA), correctly termed 3-O-caffeoylquinic acid (3-O-CQA). Only minor to trace amounts of the 4- and 5-O-CQA isomers are found in the roots, but occur in larger quantities in the leaves. Two coumarin derivatives are found in major amounts in root tissue scopoletin (6-methoxy-7-hydroxycoumarin) and its glucoside, scopolin. Both CA and scopolin can reach levels of 1% of the dry weight of the root. Very little scopolin or scopoletin is found in the leaves. 

The activities of scopoletin (6-methoxy-7-hydroxycoumarin) and esculetin (6,7-dihydroxycoumarin) were compared to each other and to those of their respective glucosides, scopolin and esculin (Table TV). The dihydroxy-coumarin was found to be just as active as the methoxy-hydroxy-compound. Thus, the presence of a free hydroxyl group at position-6 is not required for activity. Surprisingly, substitution of a glucose on the hydroxyls of both compounds resulted in the complete loss of activity. Gasser (3) found similar results with the activity of scopolin towards black root rot. 

Although free coumarins are known to occur in plants, most simple coumarins occur as glucosides. The involvement of such glucosides in the biosynthetic sequence is a unique feature among higher plants. The -D-glucoside of o-coumarinic acid (7) (Fig. 9.2) is found in plants such as sweet clover (Melilotus alba) and lavender Lavandula officinalis). Usually, free coumarin (1) is formed by hydrolysis of the glucoside and subsequent lactonization of the Z-o-coumarinic acid (8). A similar situation probably is true for umbelliferone and scopoletin (Haslam, 1974). 

Xanthotoxin and psoralen are phytoalexins. Scopolin (scopoletin-7-glucoside) is a fungitoxin formed in potatoes (E 5.4). Coumarin itself attracts certain specialized insects feeding on coumarin-containing plants (E 5.5.3). 

Umbelliferone (U) and aesculetin (A) were named after their discovery in species belonging to the family Umbelliferae (nowadays Apiaceae) and in Aesculus hippocastanum L., horse chestnut (Sapindaceae), respectively. Scopoletin (S) and its glucoside scopolin were named after their discovery in the roots of Scopolia japonica (Solanaceae) (Eijkman 1884 Schmidt 1890). 

De novo synthesis of umbeUiferone as well as its glucoside skimmin, scopole-tin/scopolin, and aeculetin in sweet potato (/. batatas) roots/tubers attacked by the black rot fungus, Ceratocystis fimbriata, was reported by Minamikawa et al. (1964). Thus, these coumarins are not only constitutive components of this plant but also phytoalexins. However, they play a minor role in contrast to certain ses-quiterpenoid phytoalexins which are also synthesized in such a situation (see Sect. 7.3). I. tricolor cv. heavenly blue was found to accumulate rapidly scopoletin and scopolin after interaction with a non-pathogenic isolate of the fungus Fusarium oxysporum (Shimizu et al. 2004). 

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. ... 

Bark contains condensed tannins, prunasin (d-mandelonitrile glucoside) emulsin eudesmic acid (3,4,5-trimethoxybenzoic acid) /i-couma-ric acid scopoletin sugars andothers (karrer). Fruit skin contains capulin anthocyanins. Prunasin is a cyanogenic glucoside that is hydrolyzed by the enzyme prunase into hydrocyanic acid (HCN, prussic acid). 

---