Studies On Chemical Constituents Of Paris Vietnamensis And Paris Mairei

The genus Paris(Trilliaceae or Liliaceae)has been used for a traditional medicine in Indian and China.Up to now,26 species have been identified and mainly discovered in Europe and Eastern Asia.In southwest China,the wild Paris was abundant.And the extensive bioactivities of the genus Paris has been reported in recent years,such as antitumor,antimicrobial,hemostasis and so on.However,illegal and immoderate exploitation coupled with environment pollution resulted in the the production of Paris was not enough.In order to alleviate resource pressure,Paris vietnamensis and Paris mairei were selected to investigate the constituents.As a result,61 compounds have been isolated and identified,including 17 new compounds and 4 aglycones of them reported for the first time.The U251,U87 MG and SHG44 cell lines were chosen to evaluate for their cytotoxicity.The research achievement was as follows:1.Studies on chemical constituents of Paris vietnamensis:The research exhibited 34 nature products,including 9 new compounds,isolated from the rhizomes of Paris vietnamensis(2 kg)extracted by 70% alcohol and water-saturated nBu OH.The structures were established as benzyl alcohol glucoside(N-1),(2S)-3-OOctadeca-9Z,12 Z,15Z-trienoylglyceryl-O-?-D-galactopyranoside(N-2),(2?,3?,5?,22R)-2,3,5,14,20,22,25-hephydroxycholest-7-en-6-one(N-3),(2?,3?,5?,22R)-2,3,14,20,22,25-hexahydroxycholest-7-en-6-one(N-4),threo-guaiacylglycerol-3-O-[6-O-(E)-p-coumaro yl]-?-D-glucopyranoside(N-5),7,11-dimethyl-3-methylene-1,6-dodecadien-10,11 anosyl-(1?2)-?-D-glucopyranoside(N-23),25(R)-spirost-5-en-3?-ol-3-O-?-L-rhamnopyr amnopyranosyl-(1?3)]-a-L-arabinopyranoside(N-34),respectively.Compounds N-9,N-10,N-18,N-27~N-29,N-32~N-34 were determined as new compounds.It's notable that the aglycones of compounds N-10,N-27,N-29 were discovered for the first time.2.Studies on chemical constituents of Paris mairei:Phytochemical studies showed 22 nature products,including 8 new compounds,as the same methods for extraction and isolation of Paris vietnamensis.The structures were characterized as 25(R)-spirost-5-en-1?,3?-diol-1-O-?-D-apiofuranosyl-(1?4)-?-D-xylopy ranosyl-(1?4)-[?-L-rhamnopyranosyl-(1?3)]-a-L-arabinopyranoside(M-1),25(R)-spiro st-5-en-3?,17?,27-triol-3-O-?-L-rhamnopyranosyl-(1?4)-?-L-rhamnopyranosyl-(1?2)-[?-L-rhamnopyranosyl-(1?3)]-?-D-glucopyranoside(M-2),25(S)-24-O-?-L-fucopyran osyl-spirost-5-en-1?,3?,21,23?,24?-pentol-1-O-?-L-rhamnopyranosyl-(1?2)-[?-D-xylopy ranosyl-(1?3)]-?-D-glucopyranoside(M-3),25(R)-spirost-5-en-1?,3?,21,23?,24?-pentol-1-O-?-D-apiofuranosyl-(1?3)-?-L-rhamnopyranosyl-(1?2)-?-D-xylopyranosyl-(1?3)-a-L-arabinopyranoside(M-4),15-oxo-18-nor-25(R)-spirost-5,13-diene-1?,3?,21,23?,24?--3-O-?-L-rhamnopyranosyl-(1?4)-?-D-glucopyranoside(M-15),25(R)-26-O-?-D-gluco pyranosyl-furost-5-en-22-methoxyl-3?,26-diol-3-O-?-L-rhamnopyranosyl-(1?2)-?-D-glu copyranoside(M-16),3?-O-[?-L-rhamnopyranosyl-(1?4)-?-L-arabinopyranosyl]-28-O-[?-L-rhamnopyranosyl-(1?6)-?-D-glucopyranosyl-(1?6)-?-D-glucopyranosyl-(1?2)-?-L-arabinopyranosyl-(1?4)-?-L-rhamnopyranosyl-(1?4)-?-D-glucopyranosyl]-oleanolate respectively.Compounds M-23~M-27 owned same structures with compounds N-10,14,15,23,31,respectively.Compounds M-2,M-4,M-6,M-9,M-10,M-15,M-17,M-18 were determined as new compounds,and the aglycone of compound M-10 was never reported.Cytotoxicity experiment:Three neuroglioma cell lines U87 MG,U251MG and SHG44 were selected to test the cytotoxicities of saponins.Compounds N-14,15,16,17,22,24~26,M-1 showed significant cytotoxicities and the structure-activity relationship was researched.The results showed that the oligosaccharide chain of trisaccharide substituted at C-3 of aglycone offered the best cytotoxicity.Innovations and significants1.61 compounds were identified from the rhizomes of Paris vietnamensis and Paris mairei,including 47 steroidal saponins,6 triterpenoid saponins and 8 non-saponins.2.17 compounds were characterized as new compounds and the aglycones of N-10,N-27,N-29 and M-10 were never reported.Furthermore,9 compounds were isolated from the genus Paris for the first time.3.By in vitro experiments,the meaningful structure-activity relationship was discussed,the theoretical basis of structural modification was provided and the clinical application prospect of the steroidal saponins was promoted.4.This research established a homebase for the further development of the genus Paris,provided a basis for effective lead compounds and owned proprietary intellectual property rights,which possessed the potential social and economic benefits.