| Yan Ling Cao,as a kind of medicinal materials,is the dry rhizome of Trillium tschonoskii Maxim.Due to the traditional efficacy,including invigorating the circulation of blood,hemostasis,tranquilizing and allaying excitement,Yan Ling Cao has attracted considerable attention.In order to explore the chemical constituents from Yan Ling Cao,UPLC-QTOF/MS was applied for identification of multiple common constituents in Yan Ling Cao and Paris polyphylla,respectively.It was found that the chemical constituents are rich and noval in Yan Ling Cao.Meanwhile,a simple,accurate and reliable high performance liquid chromatography coupled with the charged aerosol detector(HPLC-CAD)method was developed and then successfully applied for simultaneous quantitative analysis of three major components,including PolyphyllinVI,PolyphyllinVII and pennogenin 3-O-a-L-rhamnopyranosyl-(1?2)-[O-a-L-rhamnopyranosyl-(1?4)]-O-?-D-glucopyranoside.It displayed that the total content of PolyphyllinVI and PolyphyllinVII in Yan Ling Cao was more than the total content of index compoents in Paris polyphylla that were stangarded in Chinese Pharmacopoeia(2015 Edition).Qualitative and quantitative determination of major saponins in Yan Ling Cao and Paris polyphylla by UPLC-QTOF/MS and HPLC-CAD has showed a series of evidence for the possible activity of Yan Ling Cao.Based on the above results,chemical investigation of Yan Ling Cao was carried out for further study.As a result,49 compounds were isolated from the 50%ethanol of extract of Yan Ling Cao by column chromatographic technique,such as macroporous resin(SP825),MCI gel,silical gel,ODS and semi-preparative HPLC.44 compounds were elucidated by HR-ESI-MS,1D-NMR and 2D-NMR,including 37 steroid saponins,4 sterone(glycosides),and 3 sesquiterpenoid.Among them,26 compounds are new compounds.The structures of 26 new compounds were determined as 15-one-18-nor-(23S,24 S,25S)-spirost-5,13-diene-1?,3?,21,23-butanol-24-acetyl-1-O-?-D-apiofuranosyl-(1?3)-O-a-L-rhamnopyranosyl-(1?2)-[O-?-D-xylopyranosyl-(1?3)]-O-a-L-arabinopy-ranoside(1),15-one-18-nor-(23S,24R,25S)-spirost-5,13-diene-1 ?,3?,23,24-butanol-21-acetyl-1-O-?-D-apiofuranosyl-(1?3)-O-a-L-rhamnopyranosyl-(1?2)-[O-?-D-xylopy ranosyl-(1?3)]-O-?-L-arabinopyranoside(2),21-O-?-D-glucopyranosyl-15-one-18-no r-(23S,24S,25S)-spirost-5,13-diene-1?,3?,23-triol-21-acetyl-1-O-?-D-apiofuranosyl-(1?3)-(O-a-L-rhamnopyranosyl-(1 ?2)-O-[?-D-xylopyranosyl-(1?3)]-O-?-L-arabinop yranoside(3),15-one-18-nor-(23S,24R,25S)-spirost-5,13-diene-1?,3p,21,23,24-pentaol-1-O-?-D-apiofuranosyl-(1 ?3)-[O-a-L-rhamnopyranosy l-(1 ?2)]-O-a-L-arabinopyra noside(4),21-O-?-D-glucopyranosyl-15-one-l 8-nor-(23S,24S,25S)-spirost-5,13-diene-1?,3?,23-triol-21-acetyl-1-O-?-D-apiofuranosyl-(1?3)-[O-a-L-rhamnopyranosyl-(1?2)]-O-a-L-arabinopyranoside(5),15-one-(23S,24S,255)-spirost-5-ene-1?,3?,21,23-b utanol-24-acetyl-1-O-?-D-apiofuranosyl-(1?3)-(O-?-L-rhamnopyranosyl-(1?2)-[O-?-D-xylopyranosyl-(1?3)]-O-a-L-arabinopyranoside(6),(23S,24S,25S)-spirost-5-ene-1?,3?,15,21,23?,24a-hexanol-1-O-?-D-apiofuranosy l-(1 ?)-O-?-L-rhamnopyranosyl-(1?2)-[O-?-D-xylopyranosyl-(1?3)]-O-a-L-arabinopyranoside(7),(23S,24S,25S)-spi rost-5-ene-1?,3?,15,21,23a,24a-hexanol-1-O-?-L-rhamnopyranosyl-(1?2)-[O-?-D-x ylopyranosyl-(1?3)]-O-?-L-arabinopyranoside(8),(23S,24S,?25S)-spirost-5-ene-1?,3?,15,18,21,23,24-heptanol-1-O-p-D-apiofuranosyl-(1?3)-O-?-L-rhamnopyranosyl-(1?2)-[O-?-D-xylopyranosyl-(1 ?3)]-O-?-L-arabinopyranoside(9),15-one-(23S,24S,25S)-spirost-5-ene-1?,3?,18,21,23,24-hexanol-l-O-?-D-apiofuranosyl-(1?3)-O-a-L-rhamnopyranosyl-(1?2)-[O-?-D-xylopyranosyl-(1?3)]-O-a-L-arabinopyranoside(10),(23S,24S,25S)-spirost-5-ene-1?,3?,15,18,21,23,24-heptanol-1-O-(1?3)-O-a-L-rham nopyranosyl-(1?2)-[O-?-D-xylopyranosyl-(1?3)]-(O-a-L-arabinopyranoside(11),(23 S,24S,25S)-spirost-5-ene-21-ol-1?,3?,15,21,23,24-hexanol-1-O-?-D-apiofuranosyl-(1?3)-O-a-L-rhamnopyranosyl-(1?2)-[O-?-D-xylopyranosyl-(1?3)]-O-a-L-arabinop yranoside(12),(25R)-27-ol-penogenin-3-O-a-L-rhamnopyranosyl-(1?2)-[O-?-D-gluc opyranosyl-(1 ?6)]-O-?-D-glucopyranoside(19),(25S)-27-ol-penogenin-3-O-a-L-rha mnopyranosyl-(1?2)-[O-?-D-glucopyranosyl-(1?6)]-O-?-D-glucopyranoside(20),(25S)-27-[O-(?-D-glucopyranosyl)oxy]-penogenin-3-O-a-L-rhamnopyranosyl-(1 ?4)-[a-L-rhamnopyranosyl-(1?2)]-O-?-D-glucopyranoside(21),(24R,25R)-24,27-diol-pen ogenin-3-O-?-L-rhamnopyranosyl-(1?4)-[O-?-L-rhamnopyranosyl-(1 ?2)]-O-?-D-g lucopyranoside(22),(23S,25S)-23,27-diol-penogenin-3-O-a-L-rhamnopyranosyl-(1?4)-[O-a-L-rhamnopyranosyl-(1?2)]-O-?-D-glucopyranoside(23),(24R,25S)-24,27-diol-penogenin-3-O-a-L-rhamnopyranosyl-(1?4)-[O-a-L-rhamnopyranosyl-(1?2)]-O-?-D-glucopyranoside(24),(24R,25S)-24,27-diol-penogenin-3-O-a-L-rhamnopyranosyl-(1 ?2)-O-?-D-glucopyranoside(25),(24R,25S)-24,27-diol-penogenin-3-O-a-L-rhamno pyranosyl-(1?2)-[O-?-D-glucopyranosyl-(1?6)]-O-(3-D-glucopyranoside(26),(24R,25S)-24,27-diol-penogenin-3-O-a-L-rhamnopyranosyl-(1?4)-[O-?-L-rhamnopyranosy 1-(1?2)-O-a-L-rhamnopyranosyl-(1?2)]-O-?-D-glucopyranoside(27),(25R)-26-O-?-D-glucopyranosyl--furostan-?5(6),17(20)-diene-7,16,22-trione-3?,26-diol-3-O-a-L-rham nopyranosyl-(1?4)-[O-a-L-rhamnosyl-(1?2)]-O-?-D-glucopyranoside(34),5-ol-pter osterone24-O-?-D-glucopyranoside(39),3-{3'E-7',8'-dihydroxy-4'-methyl-8'-dimeth yl-3'-octenyl-8'-O-?-D-glucopyranosyl-(1?4)-[0-?-D-glucopyranosyl-(1?4)]-O-?-D-glucopyranosyl}-2,5-dihydro-1,1-dioxo-thiophen(43),3-[3'E-7,,8'-dihydroxy-4'-m ethyl-8'-dimethyl-3'-octenyl-8'-O-?-D-glucopyranosyl(1?4)]-O-?-D-glucopyranosyl]-2,5-dihydro-1,1-dioxo-thiophen(44),3-{3'E-7',8'-dihydroxy-4'-methyl-8'-dimethyl-3'-octenyl-8'-O-?-D-6"-acetyl-glucopyranosyl-(1?4)-[O-?-D-glucopyranosyl-(1?4)]-O-?-D-glucopyranosyl}-2,5-dihydro-1,1-dioxo-thiophen(45).In addition,it is an in-depth study of Yan Ling Cao in three aspects,inclding qualitative analysis,quantitative analysis and separation and identification.Mainly,a series of steroid saponins will be provided for the activity screening of hemosatatic,antineoplastic,and the study on structure-activity relationship.And it will lay the foundation for the development of innovative drugs and comprehensive development and utilization of Trillium. |
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