The word "saponin" is a free translation of the English name Saponin, which is derived fromLatinSapo means soap.Saponins areGlycosidesCompounds with more complex structures.They exist widely in plants, with a wide variety and complex composition.The international research on saponins is very active, and it has entered a new climax in the 1980s.Not only the structure of some saponins with complex structure has been confirmed, but also some errors in previous structural identification have been correctedsystem study There are many saponins in important Chinese herbal medicines.
1. Its appearance is white to light yellowish brown powder, or tea brown to brownish black paste (60% solids).
2. Some of the powder is easily soluble in water, while the undissolved part is soluble inethanolAqueous solution.pH4.5～5.5。
4. The best quality is produced fromChile、Peru、boliviaOfRosaceaeOfEvergreen treeSaponins bark of triterpenoids obtained from Quillaja saponariaSaponin, better than those obtained from other raw materials.yesFDAThe only food saponin recognized.
The saponins whose aglycones are triterpenoids are calledTriterpene saponin, mainly exists inAcanthopanaceae、leguminous、PolygalaceaeandCucurbitaceaeIt has more species than steroidal saponins and is more widely distributed.Most triterpene saponins are acidic, and a few are neutral.Saponins are connected according to aglyconesugar chainIt can be divided into monosaccharide chain saponinsdisaccharideChain saponins and trisaccharide chain saponins.On the sugar chain of some saponins, other groups are also linked by ester bonds.
2. SaponinicHemolysisThe strength of is related to the sugar part,monosaccharideChain saponins have significant effect, somedisaccharideThe chain saponin has no hemolysis, but it has hemolysis after being converted into monosaccharide chain saponin by enzyme.
Most saponins can reduce thesurface tension, with foaming property andEmulsifierFunction, can be used asCleaning agentAnd hemolysis andVenomous fishRole of.There are many Chinese medicines containing saponins, such as Polygala tenuifolia and Platycodon grandiflorum, which have the effect of expectorant and cough relieving;Some saponins also have antibacterial activity or are valuable in antipyretic, sedative, anti-cancer, etcbiological activity。Some saponins have special physiological activities, for example, ginsenosides can enhanceDNAandproteinOfbiosynthesisImprove the immune ability of the body.glycyrrhizic acidWith promotionAdrenocortical hormoneIt has the effect of relieving cough and treatmentgastric ulcerThe efficacy of disease.
Saponins are a group of naturally occurring compounds with diverse structures. It is mainly found that in plants, these saponins exude a bitter taste and are easy to foam in aqueous solutions.Saponins are considered toxic to cold-blooded animalsMammalsHowever, its oral toxicity is very low.Saponins naturally present in food are non-toxic and may even be beneficial to human diet.
A kind of complex glycoside compound, which can be generated when shaking with waterpersistenceIt looks like soap foam.stayFloraIt is widely distributed. Many traditional Chinese medicines, such as ginseng, panax notoginseng, anemarrhena, polygala tenuifolia, liquorice, platycodon grandiflorum, and bupleurum root, contain saponins;Formerly used in ChinaGleditsia sinensisWashing clothes is because it contains saponin compounds.Saponins are composed of saponin ligands and sugars, uronic acids or other organic acids.The common sugars that make up saponins areD-glucose、L-Rhamnose、D-galactose、L-arabinose、L-Xylose 。Common uronic acids areGlucuronic acid、Galacturonic acidThese sugars or uronic acids are often first synthesized into oligosaccharidessugar chain, and then C in the saponin ligand moleculethree—OHPhase condensation, or condensation of two sugar chains with OH at two different positions in the saponin ligand molecule, and - COOH in the saponin ligand molecule may also be linked with sugar to form esterGlycosidic bond。
Main categories
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SaponinLigandsThe structure of is divided into two categories:
1、Ultraviolet spectrum: After reacting with sulfuric acid, it can reach the maximum value in the range of 270~275 nmabsorption peak。Including C-12carbonylOfSteroidal saponinThe maximum absorption peak of 350 nm was found in all the samples.
2、infrared spectrum: can be used to distinguish C-25Stereoisomer。25D steroidal saponins range from 866 cm to 863 cm-1、899～894cm-1、920～951cm-1And 982cm-1FourSpectral band, 899-894cm-1Absorption ratio at 920-915cm-125 L steroidal saponin is 857 ～ 852 cm-1、899～894cm-1、920～915cm-1And 986cm-1There is also absorption at the place, of which 920-915cm-1Absorption ratio at 899-894cm-1The local strength is 3-4 times.
3. Mass spectrum: a strong m/z139Base peakM/z 115 fragment peak and a weak m/z 126 auxiliary ion peak.
4. NMR spectrum: the C-22 signal of the spiral sterol saponin appears at δ 109.5 in most cases.
1. Mass spectrometry: for triterpene saponins with C-12CycloethyleneStructure, easy to cause RDA cracking, according to the generated fragment ion peak, AB ringAnd D, E ringsSubstituentNature, number, location, etc.
2. NMR spectrum: pentacyclic triterpene oleanane type (β - aromatic resin alcohol type) contains 6 spthreeHybrid quaternary carbon atoms,thirteenThere are six quarterly carbon signals in the CNMR spectrum, namely, ursorane type (α - aromatic resin alcohol type)thirteenThere are five seasonal carbon signals in the CNMR spectrum.LupinethirteenIn CNMR spectrumIsopropylSignal.
The most common color identification reaction isAcetic anhydride-concentrated sulfuric acid(Liebermann Burchard) reaction, that is, a small amount of sample is dissolved inacetic anhydride, and then add concentrated sulfuric acid along the tube wall, yellow red purple blue green and other changes can occur, and finally fade.Steroidal saponinColor changeFaster, last displayTurquoise。Triterpene saponins can only show red or purple, but not green.Steroidal saponins and triterpenoid saponins can be preliminarily distinguished by this method.[1]
Steroidal saponins and bilesterol GeneratibleInsolubleMolecular complex, and separate accordingly. ①Where there is 3 β-OH，A/B ringTrans fused (5 α - H) or △ δ flat structure sterols, such asβ - sitosterol、Stigmasterol、CholesterolandErgosterolAnd molecular complexes formed with steroidal saponinsSolubility productMinimum. ②Any sterol with 3 α - OH or 3 β - OH esterified or glycosylated cannot form insoluble molecular complexes with steroidal saponins. ③Triterpene saponins can not form stable molecular complexes with sterols, so the separation of steroidal saponins and triterpene saponins can be realized.
Lead salt precipitation method
It can be used to separate acidic saponins and neutral saponins.
Chromatographic separation
①Adsorption chromatography: CommonAdsorbentyessilica gel、aluminaandInverted silica gelMixed solvent is generally used as eluent.For example, in the method of separating mixed steroidal saponins, first dissolve the sample in the solution containing 2%chloroformIn the benzene containing 20% chloroform, the monohydroxy sapogenin is washed out with this solvent after loading the column, and then the monohydroxy sapogenin is washed out with benzene containing 20% chloroformKeto groupFinally, the dihydroxy sapogenin was eluted with benzene containing 10% methanol.
②Distribution chromatography: Since saponins have large polarity, they can be separated by distribution chromatography.Generally, aluminum oxide or silica gel with low activity is used as adsorbent, and chloroform methanol water or other polar materials with different proportions are usedOrganic solventconductgradient elution。
Plants containing saponins include Leguminosae, Rosaceae, CucurbitaceaeAmaranthaceaeThe animals include sea cucumbers andStarfish。Ginsenosides are the most effective medicinal ingredients in ginseng ingredients. There are nearly 30 kinds of ginsenosides, each of which has its specific pharmacological function.[2]
