Studies On Chemical Constituents Of Semiaquilegia Adoxoides

The dried roots of Semiaquilegia adoxoides (DC.) Makino(Ranunculaceae) (Chinese name "Tian-Kui-Zi") were reported in ChinesePharmacopoeia as a traditional Chinese medicine for several symptoms.The roots have often been used for the treatment of tonsillitis, mastitis,scrofula and cancer since they are believed to possess antibacterial,anti-inflammatory and antineoplastic activities. However, phytochemicalstudies have been rarely conducted on Semiaquilegia probably due to thefact that it consists of only one member. Moreover, only six knowncompounds including β-sitosterol, diosgenin, griffonilide,lithospermoside, magnoflorine and one flavonoid glycoside(semiaquilinoside) were identified from the roots and aerial parts of thetitle plant.Phytochemical investigation of S. adoxoides was initiated in view ofits common usage reported in traditional Chinese medicine and itsscarcity of previous phytochemical studies. Fractionation of an ethanolextract from the roots of this plant led to the isolation and identificationof ten compounds by solvent extraction, re-crystallization and repeatedsilica gel column chromatography. On the basis of various modernspectral analysis(IR,HR-MS,FAB-MS,1HNMR,13CNMR,DEPT,~1H-~1HCOSY, HSQC, HMQC, HMBC) and acid analysis, the structuresof eight compounds were identified as β-sitosterol (SAP-1), triacontanol(SAP-2), thalifendine (SAB30-1), 4-hydroxy-1-(2-nitroethyl)benzene-4-O-(6′-O-β-D-xylopyranosyl)-β-D-glucopyranoside(SAB30-2),n-butyl-β-D-fructofuranoside(SAB30-3), n-butyl-α-D-fructofuranoside(SAB30-4),2-(β-D-glucopyranosyloxy)-4-hydroxy-benzeneacetonitrile(SAB30-5)and fructose(SAB30-6).Compounds SAB30-2 and SAB30-5 are two novel compounds. Toour best knowledge, natural products with a nitro group are rare and thereare few examples of γ-hydroxynitrile glycosides reported in naturalproduct research since most identified cyanogenic glycosides are those ofα-hydroxynitrile and β-linked with D-glucose. compounds SAP-2,SAB30-1, SAB30-3, SAB30-4 wer e is ol ate d fr om Aquilegia forthe first time. Compounds S AP-2, S A B 30-1 , S AB 30-3 , S AB3 0-4 ,S AB3 0-6 were first obtained from Semiaquilegia genus andSemiaquilegia adoxoides.In this thesis, we also present a review on the chemical and bioactivestudies of Aquilegia.