Glycosides

chemical compound
Collection
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Glycosides, also known as Glycoside Glycosides , is made of sugar or sugar derivatives Terminal base carbon atom Compounds formed by connecting with another class of non sugar substances (called aglycones, ligands or aglycones). Most glycosides are colorless, odorless and bitter. Minority glycosides such as Xanthone glycoside , anthracene glycoside Anthocyanin Etc. A few have sweet taste, such as Glycyrrhizin
Chinese name
Glycosides
Foreign name
glycosides
Pinyin
gān leì
Distribution
In vivo

Characteristics

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1. Acid-base property : Most glycosides are neutral or acidic, and a few are alkaline.
2. Solubility : Most glycosides are soluble in water ethanol , some glycosides are soluble in ethyl acetate And chloroform Insoluble to Ether Petroleum ether , benzene, etc Organic solvent Glycosides in water or other solvents with high polarity solubility , usually with combined sugar Molecular number And increase with the increase of. The nature of aglycones can also affect the solubility of glycosides. Such as cyanohydrin in water Soluble and Flavonoid glycoside It is more difficult to dissolve. Aglycone Insoluble in water, soluble in organic solvents.
3. Glycosidic bond Pyrolysis of : Glycosides are easily exposed to dilute acid or Enzymatic hydrolysis Produce sugar and aglycone. However, there are several sugar molecules in the original glycosides in some plants, which are called primary glycosides. During hydrolysis, some sugar molecules can be removed first to generate secondary glycosides with fewer sugar molecules, and the secondary glycosides can be further hydrolyzed to obtain sugar and aglycones. After glycosides are hydrolyzed into glycosides, their solubility and efficacy in water are often greatly reduced. Therefore, during collection, processing, storage and manufacturing Glycosides When the ingredients of Chinese herbal medicine are used, care must be taken to prevent hydrolysis. For example, try to reduce the breakage of plant body during collection, dry it as soon as possible after collection, keep it dry during storage, and do not place it in aqueous solution or acid solution for a long time during extraction.
4. Natural glycosides generally have certain optical activity, namely optical rotation Most of them are left-handed and not reducible. After hydrolysis, due to the formation of reducing sugar , tends to become dextral and Reducibility This property can be used to identify glycosides in Chinese herbal medicine. The reducibility before and after hydrolysis is usually checked by Fehling test.
5. Identification : Some glycosides such as saponin Xanthone glycoside Equivalency Lead acetate or Basic lead acetate The reagent generates precipitation, which can be restored to the original glycosides after lead removal. This property can be used for the extraction of glycosides.

classification

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1. The most common is based on Aglycone Of structure type Divided into Cyanoside Phenolic glycoside , alcohol glycosides, anthracene glycosides, flavonoids Glycosides saponin Cardiac glycoside coumarin Glycosides and Iridoid Glycosides;
2. According to the name of sugar Glucoside , Rhamnus rhamnoides Glycoside , Triglycoside Rue Glycosides, etc;
3. According to the number of sugars qmg , disaccharides, trisaccharides, etc;
4. According to whether glycosides are primary or secondary in organisms, they can be divided into primary glycosides and secondary glycosides;
5. According to different glycoside atoms Oxyglycoside Glucosinolate Nitrogen glycoside Carboside Oxygen glycosides are the most common in the natural world.
Oxygen glycoside (O-glycoside)
(1) Alcohol glycoside (alcoholic glycosides): Aglycone Of Alcohol hydroxyl A glycoside formed by dehydration with the hydroxyl group of the sugar terminal group. Distribution in algae Ranunculus japonicus Section Salicaceae Crassulaceae And leguminous plants, such as Salidroside , Ranunculoside with antibacterial and insecticidal effects. Gentiopicrin, used for special treatment Icteric hepatitis Disease.
(2) Phenolic glycosides: glycosides in which the phenolic hydroxyl of aglycone is combined with sugar. Mainly exists in Azaleaceae Oleaceae and Paeonia Salix Populus Sedation and analgesia in plants such as pine, pine, etc., such as gastrodia elata Active ingredient Gastrodin. It is used clinically for treatment Hyperactivity of liver yang Caused by headache
(3) Cyanoside (cyanogic glycosides): mainly refers to a class with α- Hydroxynitrile Glycosides of. It is characterized by easy hydrolysis, especially with dilute acid and Enzyme catalysis When hydrolysis is faster, the generated aglycone α - hydroxynitrile is very unstable and can be immediately decomposed into aldehydes (or ketones) and Hydrocyanic acid Mainly distributed in Rosaceae Ranunculaceae Lonicera leguminous Lineaceae Euphorbiaceae and Crassulaceae And other plants. for example Rosaceae Maturity of plants fruit The bitter almond Small dosage has the effect of relieving cough and asthma, but large dosage will cause the danger of poisoning, so it should be used with caution.
(4) Ester glycosides: Aglycone with carboxyl Sugary Terminal base The glycosides formed by carbon combination are easy to be Alkali hydrolysis Such as mountain Arrowhead Glycosides, with antifungal activity.
(5) indole Indox yl glycosides: are glycosides condensed from the hydroxyl group in aglycone indolyl alcohol and sugar. For example, indosine.
S-glucoside
Hydroxyl group of sugar terminal and aglycone Mercapto group Glycosides condensed, mainly distributed in Cruciferae In plants. for example Turnip glycoside , garlic, with special smell. (Specific to sulfhydryl compounds)
N-glycoside
Glycoside terminal carbon and aglycone Nitrogen atom Connected glycosides. as Cytidine Croton glycoside
C-glycoside
sugar Terminal base Carbon is directly related to Aglycone upper carbon atom Connected glycosides. The aglycones that make up the carbon glycosides are Flavonoids anthraquinone and gallic acid Etc. The formation of carbon glycosides is activated by the phenolic hydroxyl group of aglycone Adjacency Or the para hydrogen is dehydrated and condensed with the terminal hydroxyl group of the sugar. as Vitexin and Isomangiferin

Pharmaceutical effect

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saponin Class components can reduce Liquid surface tension And produce foam, so it can be used as Emulsifier After taking orally, it can stimulate the mucous membrane of digestive tract and promote reflexively respiratory tract And digestive tract Mucous gland It has the effect of eliminating phlegm and relieving cough, such as Platycodon grandiflorum high aspiration Aster Commonly used as Expectorants Sang Jisheng elder Saponins in the herb have the function of dispelling wind and dampness. Ginsenoside It has the function of strengthening and replenishing vital energy, and can help some Pathological state The body of Bidirectional regulation Function or name Adapt to as is function Many saponins also have cholesterol lowering, anti-inflammatory, bacteriostatic Immunomodulation , excited or inhibited Central nervous system , inhibit gastric juice secretion, kill sperm Molluscs Etc. Some Steroidal saponin There is also resistance tumour , antifungal, bacteriostatic and cholesterol reducing effects, widely used for synthesis Steroid hormone Raw materials.