青阳参苷元 | 84745-94-8

• 物质功能分类: 天然产物 - 甾体化合物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 青阳参苷元
• 中文别名: 青阳参甙元；青阳参苷元A
• 英文名称: qingyangshengenin
• 英文别名: Cynanchagenin；[(3S,8S,9R,10R,12R,13S,14R,17S)-17-acetyl-3,8,14,17-tetrahydroxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] 4-hydroxybenzoate
• CAS: 84745-94-8
• 化学式: C₂₈H₃₆O₈
• 分子量: 500.589
• InChiKey: IMRGSWAJVVVYOW-ZCARJHNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

制备方法与用途

概述

青阳参（Cynanchum otophyllum Scheid）为萝摩科鹅绒藤属植物，彝药名为肉已勃齐，汉药名为青阳参。云南亦称其为闹狗药，主要分布在云南、贵州、湖南、广西等地。秋季采根入药，临床上常用于治疗子宫肌瘤、腰痛、结核、癫痫等病症，青阳参皂苷类成分为抗癫痫的主要活性成分。

基本信息

• 规格：HPLC≥98%
• 沸点：686.4℃
• 颜色：白色
• 外观：结晶状
• 储存条件：2-8°C，干燥，避光

来源

青阳参

化学分类

甾体类

青阳参苷元的医药用途

青阳参提取物和青阳参甙（苷）均具有镇静催眠药理活性，可用于预防或治疗与镇静催眠相关疾病，尤其是用于预防和治疗各种因素引起的睡眠功能障碍性疾病。

HPLC 测定

采用HPLC法，色谱柱为Hypersil C18柱（150 mm × 4.6 mm，5 μm），流动相为甲醇-0.4%磷酸溶液（1∶1），流速0.8 mL·min−1，柱温35℃，检测波长259 nm。结果显示青阳参苷元的质量浓度在1.0～192.8 μg·mL−1之间与峰面积呈良好线性关系（r = 0.9999，n = 6），平均回收率为99.0%（n = 9）。该方法简单、快速、准确，可作为青阳参的质量控制方法。

青阳参苷元的提取 提取步骤1

• 取青阳参1 kg (Cynanchum otophyllum Schneid，山西运城青阳参种植厂出品），用95%乙醇回流提取3次，减压浓缩得到浸膏。
• 用乙酸乙酯/水溶液（1/1，v/v）萃取，将乙酸乙酯层减压浓缩得浸膏，干燥后获得约9.6 g青阳参提取物。经测定，该提取物中青阳参甙（苷）元的含量约为5% (w/w)。

提取步骤2

• 取上述所得青阳参提取物5 g，经硅胶（100-200目）柱层析（柱床：Φ=50 mm, H = 700 mm, V = 500 ml），以氯仿/甲醇梯度洗脱。
• 再经过一次柱层析，以乙腈/水 (50/50 - 60/40) 梯度洗脱，得到青阳参甙（苷）元约0.2克。

参考资料

1. 木全章，周茜兰. 青阳参的植物学、化学、药理作用和癫痫临床疗效的初步研究 [D]. 全国民族医学学术会议论文，1982.
2. 青阳参苷元. 上海诗丹德标准技术服务有限公司.[引用日期2017-09-07]
3. 李魏林, 何珺, 李洪庆, 何军. HPLC测定青阳参中的青阳参苷元 [J]. 华西药学杂志, 2009, 24(06):663-664.
4. 杨明, 李云峰, 王鲁明, 袁莉, 崔承彬, 董华进, 黄世杰, 闫根稳. 青阳参甙(苷)元和包含它的提取物的医药用途 [P]. 北京：CN101953864A, 2011-01-26.

反应信息

• 作为反应物：
  描述：

  青阳参苷元 、 4-甲氧基肉桂酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以56.8%的产率得到3-O-(4-methoxycinnamoyl)qingyangshengenin
  参考文献：
  名称：

  C 21-甾体衍生物的合成及其抗真菌活性的评价

  摘要：

  的11种C中的抗真菌活性21种从分离-steroidal化合物牛心甙，连同caudatin和qingyangshengenin的36衍生物上进行了评价菌核病等五种真菌菌株通过菌丝生长率的方法。四种衍生物1k，1y，10d和10j对S的生长表现出较强的抑制作用。硬核菌的IC 50值分别为0.0084、0.0049、0.0053和0.0034μM。

  DOI：

  10.1016/j.bmcl.2016.02.080
• 作为产物：
  描述：

  qingyangshengenin 3-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-oleandropyranosyl-(1->4)-β-D-digitoxopyranoside 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 青阳参苷元
  参考文献：
  名称：

  New pregnane glycosides from the roots of Cynanchum otophyllum

  摘要：

  Six new pregnane glycosides with an acyl at C-12 and a straight sugar chain at C-3, namely otophyllosides H-M (1-6), were isolated from the roots of Cynanchum otophyllum (Asclepiadaceae) collected from Eryuan County in Yunnan province of China. Their structures were characterized to be qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta -D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(l -> 4)-beta-D-digitoxopyranoside (1), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 - 4)-0-D-cymaropyranosyI-(1 - 4)-p-D-digitoxopyranoside (2), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)- beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-digitoxopyranoside (3), qingyangshengenin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-thevetopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl(1 -> 4)-beta-D-digitoxopyranoside (4), caudatin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 4 )-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranoside (5), caudatin 3-0-beta-D-glucopyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranoside (6), respectively, on the basis of detailed spectroscopic analysis and chemical method. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.06.001

文献信息

• Cynanauriculoside C–E, three new antidepressant pregnane glycosides from Cynanchum auriculatum
  作者：Qing-Xiong Yang、Yong-Chang Ge、Xiao-Yan Huang、Qian-Yun Sun

  DOI：10.1016/j.phytol.2011.02.009

  日期：2011.6

  on the bioactive screening results, three new pregnane glycosides named as cynanauriculoside C–E (1–3), were isolated from the roots of Cynanchum auriculatum Royle ex Wight (Asclepiadaceae), together with two known ones, otophylloside L (4) and cynauricuoside C (5). On the basis of detailed spectroscopic analysis and chemical method, the structures of new compounds were characterized to be qingyangshengenin

  基于所述生物活性筛选结果，命名为cynanauriculoside C-E（三个新孕糖苷1 - 3），从根分离白首乌茎叶（萝藦科），加上两个已知的，otophylloside L（4）和柳苦苷C（5）。在详细的光谱分析和化学方法的基础上，将新化合物的结构表征为庆阳生宁3- O- β- d-油基吡喃糖基-（1→4）-β- d-环吡喃果糖苷（1），庆阳生宁3- O -β- d-吡喃葡萄糖基- （1→4）-β- d-葡萄糖吡喃糖基-（1→4）-α- l-环吡喃糖基-（1→4）-β- d-油基吡喃糖基-（1→4）-β- d-环吡喃果糖苷（2）和caudatin 3- O- β- d -glucopyranosyl-（1→4）-β- d -glucopyranosyl-（1→4）-β- d -cymaropyranosyl-（1→4）-β- d -oleandropyranosyl-（1→4）-β-
• C21 Steroidal Glycosides from Cynanchum wilfordii
  作者：Wen-Juan Xiang、Lei Ma、Li-Hong Hu

  DOI：10.1002/hlca.200900057

  日期：2009.12

  Eight new C21 steroidal glycosides, named wilfosides A–H (1–8, resp.), along with one known compound wilfoside KIN (9), were isolated from the roots of Cynanchum wilfordii. The structures of the new glycosides were determined on the basis of spectroscopic analysis, including 1D‐ and 2D‐NMR, and ESI‐MS techniques, as well as by comparison of the spectral data with those of related compounds.

  八新的C 21甾体糖苷，命名wilfosides A-H（1 - 8，RESP），与一种已知化合物wilfoside KIN（沿9），从根分离牛心甙。在光谱分析的基础上确定了新糖苷的结构，包括1D和2D-NMR，ESI-MS技术以及将光谱数据与相关化合物的光谱数据进行了比较。
• Design, synthesis and anticancer activity of naturally occurring C21-steroidal aglycone 3β-nitrogenous heterocyclic ester derivatives
  作者：Xiao-San Li、Rui Xing、Ming-Shang Liu、Xiao-Yan Liang、Mei-Fang Chen、Zhen-Dong Liang、Jing-Fen Nie、Hui Luo、Yong-Mei Huang、Xue-Mei Yang

  DOI：10.1016/j.molstruc.2023.135778

  日期：2023.9

  To investigate the effect of introduction of the nitrogenous heterocyclic ester group on the antitumor activities of naturally occurring C21-steroidal aglycone, a series of novel 3β-nitrogenous heterocyclic ester derivatives of caudatin, kidjoranin, qingyangshengenin, and rostratamin were synthesized. The results showed that most of synthetic derivatives showed moderate to significant cytotoxic activities

  为了研究引入含氮杂环酯基团对天然存在的C 21 -甾体糖苷配基抗肿瘤活性的影响，合成了一系列新的3 β-含氮杂环酯衍生物，包括牛尾草素、kidjoranin、青羊神根素和rostratamin。结果表明，大多数合成衍生物对四种人类癌细胞（MCF-7、HCT-116、HeLa 和 HepG2）表现出中等至显着的细胞毒活性，其中具有 piperidine-4-acetyl 取代基的化合物 1s 和 2c 表现出最高的细胞毒活性对四种人类癌细胞的细胞毒活性，IC 50值范围分别为 3.30 至 6.73 μM 和 3.07 至 6.37 μM。进一步的抗肿瘤机制研究表明，化合物2c在体外以剂量依赖的方式有效诱导细胞凋亡，使细胞周期停滞在S期。总的来说，这些目前的研究表明，将含氮杂环酯基团引入 C-3 位是提高天然存在的 C 21 -甾体糖苷配基抗癌活性的有效策略之一，值得进一步研究。
• Cytotoxicity of pregnane glycosides of Cynanchum otophyllum
  作者：Mi Zhang、Xiang Li、Cheng Xiang、Yi Qin、Jing He、Bao-Cai Li、Peng Li

  DOI：10.1016/j.steroids.2015.08.010

  日期：2015.12

  Fourteen new pregnane glycosides, including nine caudatin glycosides (1-9), three qinyangshengenin glycosides (10-12), one kidjoranin glycosides (13) and one gagaminin glycosides (14), along with twelve known analogs (15-26) were isolated from roots of Cynanchum otophyllum Schneid. Their structures were deduced by detailed analysis of 1D and 2D NMR spectra, as well as HRESIMS. In this study, all pregnane glycosides obtained (1-26) were evaluated for their cytotoxic activities using three cancer cell lines (HepG2, Hela, U251). As results, except 6 and 10, other twenty-four pregnane glycosides showed cytotoxicities at different degrees against three cell lines. (C) 2015 Elsevier Inc. All rights reserved.
• Identification of new qingyangshengenin and caudatin glycosides from the roots of Cynanchum otophyllum
  作者：Xiao-Xia Ma、Dong Wang、Ying-Jun Zhang、Chong-Ren Yang

  DOI：10.1016/j.steroids.2011.03.019

  日期：2011.9

  HPLC analysis of the roots of Cynanchum otophyllum Scheind (Asclepiadaceae) led to the isolation of six new pregnane glycosides, specifically otophyllosides N-P (2-4) and otophyllosides Q-S (7-9), in addition to the identification of three known C-21 steroidal glycosides, otophylloside A (1), otophylloside B (5) and caudatin 3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl-(1 -> 4)-beta-D-cymaropyranoside (6). The structure of each glycoside was determined by detailed spectroscopic analysis and chemical methods. All compounds contain qingyangshengenin or caudatin aglycones and a straight sugar chain consisting of 4-7 hexosyl moieties with the mode of 1 -> 4 linkage. The optically isomeric monosaccharides, D- and L-cymarose, coexisted in both otophyllosides R (8) and S (9). (C) 2011 Elsevier Inc. All rights reserved.