桑多斯虎眼万年青化学成分及药理活性研究

发布时间：2020-06-10 23:08

【摘要】：桑多斯虎眼万年青(Ornithogalum saundersiae Baker),为天门冬科(Asparagaceae)虎眼万年青属球根状植物,原产于南欧和南非地区,近年来,被广泛培育为花园植物。从该种植物已发表的科学研究中发现,以OSW-1为代表的胆甾烷型留体皂苷类化合物具有显著的药理活性,我们从中得到启发对该种植物进行进一步的植物化学方面研究,因此本硕士学位论文主要开展了采用多种不同的色谱分离手段相结合对桑多斯虎眼万年青乙醇提取物的正丁醇萃取液中的甾体皂苷类化合物进行了分离纯化和结构鉴定,并在人体肿瘤细胞毒性药理模型和LPS诱导原代小鼠腹腔巨噬细胞炎症因子NO生成模型上,对已经分离鉴定的化合物进行了初步的药理活性筛选。结果表明,从桑多斯虎眼万年青(O.saundersiae Baker)乙醇提取物的正丁醇部分已经分离并鉴定了 26个化合物(1-26),其中19个新化合物(1-19)。这26个化合物分别为:(22S)-3β-[(β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl)oxy]-1 1α22-dihydroxycholest-5,24-dien-16β-yl α-L-rhamnopyranoside(1),(22S)-3β-[(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl)oxy]-1 1α,22-dihydroxycholest-5,24-dien-16β-yl α-L-rhamnopyranoside(2),(22S)-3β-[(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-22-hydroxycholest-5,24-dien-1 6β-yl α-L-rhamnopyranoside(3),(22S)-3β-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-22-hydroxycholest-5,24-dien-16β-ylα-L-rhamnopyranoside(4),(22S)-3β-[(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl)oxy]-1 1α,22-dihydroxycholest-5-en-16β-yl α-L-rhamnopyranoside(5),(22S)-3β-[β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-1 1α,22-dihydroxycholest-5-en-16β-yl α-L-rhamnopyranoside(6),(22S)-1β-[(α-L-rhamnopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-22-hydroxycholest-5,24-dien-16β-yl α-L-rhamnopyranoside(7),(22S)-1β-[β-D-glucopyranosyl)oxy]-3β-[(β-D-glucopyranosyl)oxy]-22-hydroxycholest-5,24-dien-16β-yl α-L-rhamnopyranoside(8),3-[(α-L-rhamnopyranosyl-(1→2)-β-D-gluc opyranosyl-(1→2)-β-D-glucopyranosyl)oxy]-16,23-epoxy-1 1α,22-dihydroxy-23-(2-methyl-1-propenyl)-(3β,16β,22R,23S)-yl cholestane triglycoside(9),3-[(β-D-glucopyranosyl-(1→2)-β-D-glucopyranosy 1)oxy]-1623-epoxy-22-hydroxy-23-(2-methyl-1-propenyl)-(3β,16β,22R,23S)-yl cholestane diglycoside(10),3-[(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1-→6)-β-D-glucopyranosyl)oxy]-16,23-epoxy-23-hydroxy-22-(2-methyl-1-propenyl)-(3β,16β,22S,23R)-24-norchol-5-en-18-al(11),3-[(α-L-rhamnopyranosy l-(1→2)-β-D-glue opyranosyl→2)-β-D-glue opyranosy 1)oxy]-16,23-e poxy-23-hydroxy-22-(2-methyl-1-propenyl)-(3β,16β,22S,23R)-24-norc ho l-5-en-18-oic acid(12),(23E)-cholest-5523-dien-1β,3β,16β25-tetrol 1-O-ββ-D-glucopyranoside 16-O-α-L-arabinopyranoside(13),(23E)-cholest-5,23-dien-1β,3β,16β,25-tetrol 1-O-β-D-glucopyranos ide 16-0-(3-0-3,4,5-trimethoxy benzoy l-α-L-arabinopyranoside)(14),(23E)-cholest-5,23-dien-1β,3β,16β,25-tetrol 1-O-β-D-gluc opyranos y l-(1→6)-)β-D-glucopyranos ide 16-0-(3-0-3,4,5-tr imethoxybe nzoy 1-α-L-arabinopyranoside)(15),(23E)-cholest-5,23-dien-1β,3β,16β-trio 1-25-O-n-butyl 1-O-β-D-glucopyranosyl-(1→6)-)β-D-glucopyranoside 16-0-(3-0-3,4,5-trimethoxybenzoy l-α-L-arabinopyranos ide)(16),22-[(β-D-glucopyranosyl)oxy]-16,23-epoxy-1,3,1 1-trihydroxy-23-(2-methyl-1-propenyl)-(1α,3α,11α,16β,22R,23S)-yl cholestane glycoside(17),3β-[(β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl)oxy]-16β-[(β-D-glucopyranosyl-(1→6)-D-gluc opyranosy l-(1→4)-β-D-xylopyranosy l-(1 3)-2-O-acety l-α-L-arabinopyranosy l)oxy]-17α-hydroxy-cholest-5-en-22-one(18),cholest-5-en-16,18-epoxy-20-[5',5'-dimethylfuran-2'(5'H-one]-3β,18α-dihydroxy 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(12)-β-D-glucopyranoside(19),(22S)-3β,11α,22-trihydroxycholest-5,24-dien-16β-ylα-L-rhamnopyranoside(20),(22S)-3β-[(β-D-glucopyranosyl)oxyl]-11α,22-dihydroxycholest-5,24-dien-116-yl α-L-rhamnopyranoside(21),(22S)-3β-[(β-D-glucopyranosyl)oxyl]-11α,22-dihydroxycholest-5-en-16β-yl α-L-rhamnopyranoside(22),3-[(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosylDoxy]-16,23-epoxy-22-hydroxy-23-(2-methyl-1-propenyl)-(3β,16β,22R,23S)-yl cholestane triglycoside(23),3-[(α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl)oxy]-16,23-epoxy-23-hydroxy-22-(2-methy l-1-propenyl)-(3β,16β,22S,23R)-24-norchol-5-en-18-al(24),3,4,5-0-trioxymethyl benzoate(25),N-butyl phthalate(26)。以上化合物的药理活性筛选结果显示,化合物3在剂量为1×10-5M时对人乳腺癌细胞MCF-7有一定的细胞毒作用(IC50值为0.20μM,阳性对照药紫杉醇的IC50值为19.9 nM)。化合物12在剂量为1 X 10-5 M时对LPS诱导原代小鼠腹腔巨噬细胞释放的炎症因子NO具有良好的抑制作用(抑制率为56.81%,阳性对照药为地塞米松的抑制率为95.74%)。
【学位授予单位】：北京协和医学院
【学位级别】：硕士
【学位授予年份】：2019
【分类号】：R284.1;R285
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本文编号：2706997