Glucoside

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Chemical structure of decyl glucoside, a plant-derived glucoside used as a surfactant.

A glucoside is a

fermentation or enzymes
.

The name was originally given to plant products of this nature, in which the other part of the

cane sugar, which appear to be ethers also. Although glucose is the most common sugar present in glucosides, many are known which yield rhamnose or iso-dulcite; these may be termed pentosides. Much attention has been given to the non-sugar parts (aglyca) of the molecules; the constitutions of many have been determined, and the compounds synthesized; and in some cases the preparation of the synthetic glucoside effected.[1]

The simplest glucosides are the alkyl ethers which have been obtained by reacting hydrochloric acid on alcoholic glucose solutions. A better method of preparation is to dissolve solid anhydrous glucose in methanol containing hydrochloric acid. A mixture of alpha- and beta-methylglucoside results.[1]

The classification of glucosides is a matter of some intricacy. One method based on the chemical constitution of the non-glucose part of the molecules has been proposed that posits four groups: (I)

prussic acid. Alternate classifications follow a botanical classification, which has several advantages; in particular, plants of allied genera contain similar compounds. In this article the chemical classification will be followed, and only the more important compounds will be discussed herein.[1]

Ethylene derivatives

These are generally mustard oils, which are characterized by a burning taste; their principal occurrence is in

scammony; it hydrolyses to glucose and jalapinolic acid.[1]

Benzene derivatives

These are generally oxy and oxyaldehydic compounds.[1]

Benzoic acid derivatives

The benzoyl derivative cellotropin has been used for tuberculosis. Populin, which occurs in the leaves and bark of Populus tremula, is benzoyl salicin.[1] Benzoyl-beta-D-glucoside is a compound found in the fern Pteris ensiformis.

Phenol derivatives

There are a number of glucosides found in

emulsin convert it into glucose and saligenin, ortho-oxybenzylalcohol. Oxidation gives the aldehyde helicin.[1]

Styrolene derivatives

This group contains a benzene and also an

phloroglucin ester of meta-oxy-para-methoxycinnamic acid or isoferulic acid, C10H10O4.[3]

Anthracene derivatives

These are generally substituted anthraquinones; many have medicinal applications, being used as purgatives, while one, ruberythric acid, yields the valuable dyestuff madder, the base of which is alizarin. Chrysophanic acid, a dioxymethylanthraquinone, occurs in rhubarb, which also contains emodin, a trioxymethylanthraquinone; this substance occurs in combination with rhamnose in Frangula bark.[6]

Arguably the most important

prussic acid. Emulsin also decomposes amygdalin directly into these compounds without the intermediate formation of mandelic nitrile glucoside.[6]

Several other glucosides of this nature have been isolated. The saponins are a group of substances characterized by forming a lather with water; they occur in soap-bark. Mention may also be made of indican, the glucoside of the indigo plant; this is hydrolysed by the indigo ferment, indimulsiri, to indoxyl and indiglucin.[6]

References

  1. ^ a b c d e f g Chisholm 1911, p. 142.
  2. PMID 11330806
    .
  3. ^ Chisholm 1911, pp. 142–142.
  4. ^ Hogan, C. Michael (2008). Stromberg, N. (ed.). "Aesculus californica". Globaltwitcher.com. Archived from the original on 22 November 2012. Retrieved 22 October 2008.
  5. doi:10.1002/jps.3030371113
    .
  6. ^ a b c d Chisholm 1911, p. 143.

Further reading

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