Studies On Chemical Constituents Of Paris Delavayi Franchet

The rhizomes of the plants of genus Paris are widely used as folk medicine in China for heat-clearing and detoxifying, relieving swelling and pain, sore throat, snake bites and traumatic injure.Paris delavayi Franchet belongs to the Paris.Paris delavayi Franchet is mainly grown in Yuannan, Guizhou, Hubei and Hunan province. The appropriate altitude for the living of Paris delavayi Franchet is about 1300 to 2000 meters.At present the study of Paris delavayi Franchet reported less, this topic mainly research the rhizomes,combining modern spectrum analysis technique for structural identification and biological activity test in order to clarify the main chemical composition, and discover new compounds with anti-tumor activities.In this way,we may provide new theoretical basis and application prospect for Paris delavayi Franchet.To investigate saponins in the rhizomes of Paris delavayi Franchet, the rhizomes of Paris delavayi Franchet were extracted with 70% Et OH, and then the crude extraction was purified by silica gel, ODS, and Sephadex LH-20 chromatography columns. The structures of the isolated compounds were determined on the basis of chemical and spectroscopic methods. From the rhizomes of Paris delavayi Franchet 16 saponins were isolated and identified as paris saponin II(1), 25(R)-pennogenin-3-O-α-L-arabinofuranosyl-(1â†'4)-[α-L-rhamnopyranosyl-(1â†'2)]-β-D-glucopyranoside(2),chikusetsusaponin IV a methyl ester(3),3-O-(6′-butyl ester)-β-D-glucuropyranosyl-oleanolic acid-28-O-β-Dglucopyranoside(4),pregna-5,16-diene-3β-ol-20-one-3-O-α-L-rhamnopyranosyl-(1â†'2)-[α-L-rhamnopyranosyl-(1â†'4)]-α-L-rhamnopyranosyl-(1â†'2)-β-D-glucopyranoside(5),26-O-β-D-glucopyranosyl-3β,20α,26-triol-25(R)-Δ5,22-dienofurostan-3-O-α-L-rhamnopyranosyl-(1â†'4)-α-L-rhamnopyranosyl(1â†'4)-α-L-rhamnopyranosyl(â†'4)-β-D-glucopyranoside(6),16β-[[(4S)-5-(β-D-gluco-pyranosyloxy)-4-methyl-1-oxopenty]oxy]-3β-[(O-α-L-rhamno pyranosyl-(1â†'4)-α-L-rhamnopyranosyl-(1â†'4)-α-L-rhamnopyranosyl-(1â†'4)-β-D-glucopy ranosyl)oxy]-pregn-5-en-20-one(7), 26-O-β-D-glucopyranosyl-3β,26-dihydroxy-25(R)-furosta-5,20(22)-dien-3-O-α-L-rhamnopyranosyl-(1â†'4)-α-L-rhamnopyranosyl-(1â†'4)-α-L-rhamnopyranosyl-(1â†'4)-β-D-glucopyranoside(8), diosgenin-3-O-β-D-glucopyrano-(1â†'2)-β-D-glucopyranoside(9), diosgenin-3-O-β-D-glucopyranoside(10), 25(R)-pennogenin-3-O-α-L-rhamnopyranosy-(1â†'4)-α-L-rhamnopyranosyl-(1â†'4)-β-D-glucopyranoside(11),25(R)-pennogenin-3-O-α-L-rhamnopyranosyl-(1â†'4)-[α-L-rhamnopyranosyl-(1â†'2)]-β-D-glucopyranoside(12), 25(R)-pennogenin-3-O-α-L-rhamnopyranosy-(1â†'4)-β-D-glucopyranoside(13),(25S)-27-hydroxypennogenin-3-O-α-L-rhamnopyranosyl-(1â†'2)-β-Dglucopyranoside(14),(25S)-27-hydroxypennogenin-3-O-α-L-rhamnopyranosyl-(1â†'4)-[α-L-rhamnopyranosyl-(1â†'2)]-β-D-glucopyranoside(15),(25S)-27-hydroxypennogenin-3-O-α-L-rhamnopyranosyl-(1â†'4)-α-L-rhamnopyranosyl-(1â†'4)-[α-L-rhamnopyranosyl-(1â†'2)]-β-D-glucopyranoside(16).Compounds 6-8 are new compounds.Compounds 3, 4, 5, 9,10, 11 have been obtained from Paris delavayi Franchet for the first time.The cytotoxic activities of the 16 steroidal saponins against several human tumor cell lines were evaluated by MTT colorimetric assay. The results showed that compounds1,3-10,13,14 showed inactive to the Hep G2 and U87 MG cell lines, however, compounds2,11,12,15,16 showed notable cytotoxic activity against the two kinds of tested cell lines.And the preliminary structure-activity relationship of compounds are discussed.Innovations and significance:1. The systematic study of the chemical constituents of Paris delavayi Franchet was carried out for the first time, and 18 compounds were isolated and identified,including two triterpenoid saponins, two pregnane saponins, ten steroidal saponins and two furos tanol saponins.The preliminary constituents of the plant were explicited by large through the studies.2. Chemical novelty: Three new steroidal saponins were identified and six compounds were firstly obtained from this plants.Three compounds were firstly obtained fromthis genus.The aglycone moieties of the three new compounds were rare, the aglycone of oleanolic acid and pregnane were firstly discovered from this plant. The structures of the 3-O-sugar moieties of compounds 6-8 were very rare.The glucuronic acid of compounds 4 and 5 were firstly obtained from this genus.3. With the in vitro anti-tumor experiments, we found that several steroidal saponins exited significant cytotoxic activities against several tumor cell lines.4. My study focused on constituents of the rhizome of Paris delavayi Franchet have established a homebase for the further rational utilization and development of the plant resources.