"oxidation Alkaline Solution" The Preparation Of The Original And The Original Ginsenosides Of Ginseng Diol Structure Modification Research

A study of preparation of protopanaxogenines from the total panaxosides of leaves and stems of Panax quinquefolium L. by oxidative alkaline-degradation was undertaked and six compounds were isolated from the products.On the basis of spectroscopic analysis and physico-chemical characters, the structures of them were identified as following, three protopanaxogenines:20(S)-protopanaxadiol (PPD) (1), 20(S)-protopanaxatriol (PPT) (2),24(R)-ocotillol (3); two dammarane type triterpenes with cyclization at the side chain:(20S,24R)-20,24-epoxydammarane-3β,12β,25-triol (4),(12R,20S,24R)-20,24; 12,24-diepoxy-24-deisopropyldammarane-3β-ol (5), as well as 20(S)-ginsenoside-Rh2 (6).Among them, compound 5 was a new compound.Chemical synthesis of oleoyl PPD by oleoyl chloride was performed. Meanwhile, esterified PPDs with five kinds of fatty acids using DCC method were prepared. Seven derivates (7-13)were obtained and the structures were identified by spectroscopic data analysis, as:20(S)-protopanaxadiol-12β-oleate (7), 20(S)-protopanaxadiol-3β,12β-dioleate (8),20(5)-protopanaxadiol-3β-hexanoate (9), 20(S)-protopanaxadiol-3β-enantate (10),20(S)-protopanaxadiol-3β-caprylate (11), 20(S)-protopanaxadiol-3β-pelargonate (12),20(5)-protopanaxadiol-3β-laurate (13). Compounds 7-13 were all new compounds.The antineoplastic activity of the derivates of 20(S)-protopanaxadiol were determined by MTT. The preliminary tests showed that, compounds 8,10,11,12 displayed better inhibitory activity than PPD against human adenocarcinoma of lung cell A549, compounds 7,8,13 displayed better inhibitory activity than PPD against human heptacellular carcinoma cell HepG2, compounds 8,11,12 displayed better inhibitory activity than PPD against human lung carcinoma cell H1703.