Studies On The Chemical Constituents And Their Anti-timor Activity In Paris Polyphylla Var. Pubescends, Paris Verticillata M. Bieb ＆ Paris Axialis H. Li

Paris L. belongs to a genus of Liliaceae family. The genus Paris is a complex genus with approximately 24 species, which grow primarily in the temperate areas and tropical regions of Europe and Asia continent. There are 19 species in our country, especially in Guangxi, Yunnan and Guizhou province. It is pungent in taste and cold in nature. It shows antitumor, hemostasis, immunity adjustment, analgesia, antibacterial and anti-inflammation. In order to discover the bioactive constituents from Paris polyphylla var. pubescends, the systemic chemical investigation had been carried out and 17 compounds are isolated and elucidated on the basis of spectroscopic and chemical methods. Among them, quercetin is obtained from the Paris genus for the first time. The other 16 compounds obtained from this plant for the first time are determined as follows: diosgenin(1), Paris saponinⅤ(2), Paris saponinⅥ(3), diosgenin-3-O-α-L-arabinofuranosyl(1→4)-β-D-glycopyranoside(4), pennogenin-3-O-α-L-arabinofuranosyl(1→4)-β-D-glycopyranoside(5), Paris saponinⅠ(6), Paris saponin H(7), Paris saponinⅢ(8), Paris saponinⅡ(9), Paris saponinⅦ(10),β-Sitosterol(11), stigmasterol (12), daucosterol (13),β-ecdysterone (14), Kaempferol (15), quercetin(16), stigmasterol-3-O-β-D-glycopyranoside(17).11 compounds are isolated and elucidated on the basis of spectroscopic and chemical methods from the herbs of Paris verticillata. Among them, 4-hydroxymethyl-γ-butyrolactone(11) are obatained from the Paris genus for the first time. Paris saponinⅤ(1), Paris saponinⅥ(2), Paris saponinⅠ(3), Paris saponin H(4), Paris saponinⅡ(5), Paris saponinⅦ(6),β-Sitosterol(7), stigmasterol (8), daucosterol (9) are isolated from this plant for the first time.26 compounds are isolated and elucidated on the basis of spectroscopic and chemical methods from the rhizomes of Paris axialis H. Li. Among them, luteolin(8), luteoloside(9), naringenin(10), quercetin-3-O-β-D-galactopyranoside (13), Myrincitrin(15), 4,2',4'-trihydroxychalcone(16), Rutin(18), Kayaflavone (20), Amentoflavone(21) are obtained from the Paris genus for the first time. Diosgenin(1), pennogenin-3-O-α-L-arabinofuranosyl(1→4)-β-D-glycopyranoside(5), Kaempferol(11), quercetin(12), isorhamnetin-3-O-β-D-glycopyranosyl(1→6) glycopyranoside(14), isorhamnetin-3-O-β-D-glycopyranoside(17), isorhamnetin- 3-O-α- L-rhamnopyranosyl(1→2)-β-D-glycopyranoside(19),β-Sitosterol(22), stigmasterol (23), daucosterol (24), stigmasterol-3-O-β-D-glycopyranoside(25),β-ecdysterone (26) are isolated from this plant for the first time.Moreover, cytotoxicity of P. polyphylla var. pubescends, P. verticillata and P. axialis to B16 were determined by MTT assay in vitro. The results of the antitumor experiments showed that EtOAc and n-BuOH extracts of these three plants had strong activity. The steroidal saponins from P. polyphylla var. pubescends revealed significant activity to B16, with IC50 value below or near 50μg/mL. Diosgenyl saponins generally showed stronger cytotoxicity than pennogenyl saponins, which indicated that 17-hydoxyl reduced the cytotoxicity of the diosgenyl saponins. In addition, the more the number of the saccharide groups is, the stronger the cytotoxicity of diosgenyl or pennogenyl saponins is, especially for the rhamnose and arabinose.In addition, we investiged the relationship of the Paris genus plants and the biosynthetic pathways of steroidal saponins in Paris plants.