Studies On The Chemical Constituents, Fingerprint And Bioactivities Of Purple Red Ginseng

Purple red ginseng was the ginseng deep processing products by steaming anddrying of ginseng repeatedly. In the preparation process, Maillard reaction anddegradation occcred, part of the chemical constituents have been changed. So far,there were few studies on the chemical constituents and bioactivities of this new deepprocessed products of ginseng. In this thesis, the chemical constituents, fingerprintand bioactivities of Purple red ginseng were studied for the first time, which wasexpected not to discover the different constituents but to offer scientific basis toaccelerate its further application and guarantee the quality control.Firstly, the chemical constituents of purple red ginseng were investagated.27kinds of compounds were extracted, separated and purified by various methods. Then25of them were identified according their physicochemical properties, TLC,spectrum analysis(¹³C-NMR、¹H-NMR、HMBC、HMQC) and X-ray diffraction bycrystals. The structures of them were identified as follows:20（S）-protopanaxadiol （1）;20（R）-protopanaxadiol （2）; Ginsenoside Rd （3）;20（S）-ginsenoside Rg₃（4）;20（R）-ginsenoside Rg₃（5）; Ginsenoside Rk₁（6）; Ginsenoside Rg₅（7）;20（S）-protopanaxatriol （8）;20（R）-protopanaxatriol （9）; Ginsenoside Rg₆（10）;20（S）-ginsenoside Rh₁（11）;20（R）-ginsenoside Rh1（12）;20（S）-ginsenoside Rg2（13）;20（R）-ginsenoside Rg2（14）;Ginsenoside Rf （15）; Notopanaxoside R₂（16）; Ginsenoside Ro （17）; Zingibroside R₁（18）;β-sitosterol （19）; β-daucosterol （20）;4-O-α-D-glucopyranosyl-D-Glucose （21）；palmitic acid （22）; Hexadecane （23）; n-Dodecane （24）;2-oxopropyl-α-D-glucopyranoside （25）.On the basis of extraction and separation of chemical constituents of purple redginseng, saponins and their contents of purple red ginseng and white ginseng were compared by UPLC-ESI-MS/MS method. The results showed that in the preparationprocess, Maillard reaction and degradation occcred, and the types and quantities ofginseng saponins changed, resulting in20（S）-ginsenoside Rg3,20（R）-ginsenoside Rg3,20（R）-ginsenoside Rh₁,20（R）-ginsenoside Rg₂, ginsenoside Rk₁, ginsenoside Rg5,ginsenoside Rd, ginsenoside Ro, zingibroside R₁,20（S）-protopanaxatriol,20（R）-protopanaxatriol,20（S）-protopanaxadiol,20（R）-protopanaxadiol and so on.In this paper, the fingerprints of purplish red ginseng was established andevaluated for the first time.12common peaks were found in the HPLC-PDAfingerprint. In the precision, reproducibility and stability test, RSD of each commonpeak relative retention time was less than1%, and RSD of relative peak area less than3%. Samples of10batches were of high similarity and the similiarity degree were0.885～1.000. The fingerprint of purplish red ginseng showed good reproducibility,and the method is stable and reliable, which can be used for the quality control ofpurplish red ginseng.Due to the higher content of20（S）-protopanaxatriol in purplish red ginseng, select20（S）-protopanaxatriol as raw material.22fatty acid esters of PPT，including two knownoleoy esters and other20new fatty acid esters，were synthesized using acyl chloride or fattyacid and N, N’-dicyclohexylcarbodiimide （DCC）. The structures were elucidated by thecombined analysis of NMR and ESI-MS. The antitumor activities were tested in vitro in threecell lines, HepG2, Hela and SGC-7901, using the MTT method for the first time. The structuralrelationships between fatty acid derivatives of PPT and their cytotoxic properties were alsodiscussed preliminarily in this paper. The purpose is to find and prepare antitumor compoundswith high efficiency and low toxicity, and to provide the theoretical basis for development andinnovation of ginsenoside as anticancer drugs.In this thesis, the serum pharmacochemistry of the extract of Purplish redginseng was studied. Serum was collected after oral administration of the extract ofPurplish red ginseng to rats. The sample was detected by UPLC-ESI-MS/MS, and themain compounds of the serum containing Purplish red ginseng were determined. Rat’sserum contains14transitional blood components, among which six were originalconstituents of extract of Purplish red ginseng and the other might be metabolites ofthe original constituents. The bioactive components of the purplish red ginseng after oral administration of the extracts were clarified, and the mechanisms of action ofPurplish red ginseng were illustrated, which will provide the theoretical basis for itswide application in clinic.Investigation on the effect of purplish red ginseng on the sexual aetivity of agedmale rats. The results showed that purplish red ginseng can improve sexual activity ofsenile rats evidently compared with controlled groups, improve their sexual desire andcourtship times; It can act on hypothalamic-testicular-gonadal axis and regulate sexhormone levels, so as to promote the generation of androgen and serum testosterone;purplish red ginseng can increase the sperm vigor; It also can increase the content of5-HT and DA of rats’hypothalamus. Aphrodisiac of purplish red ginseng wassignificant, and some test index even better than the positive drug. These will providetheoretical basis for the development and utilization purplish red ginseng asimpotence drug.The chemical constituents, fingerprint and bioactivities about purplish red ginsengwere made a deep investigation in the thesis for the first time. The results wouldsupply good methods for quality control and offere strong, accurate and scientifictheoretical basis to the wide application of this kind of ginseng, which might produceeven higher theoretical and economic value.