Qingyangshengenin
(Synonyms: 青阳参甙元) 目录号 : GC39061Qingyanshengenin (NSC 379666; compound 2) 是一种孕烷糖苷,一种从Cychuchumot ophyllum (Asclepiadaceae) 的根中分离出的 C21 类固醇糖苷配基。Qingyanshengenin 具有抗癌活性。
Cas No.:84745-94-8
Sample solution is provided at 25 µL, 10mM.
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Qingyanshengenin (NSC 379666; compound 2), a pregnane glycoside, is a C21 steroidal aglycone isolated from the root of Cynanchumot ophyllum (Asclepiadaceae). Qingyanshengenin has anti-cancer activity[1].
[1]. Dong J, et al. C21 steroidal glycosides with cytotoxic activities from Cynanchum otophyllum. Bioorg Med Chem Lett. 2018 May 15;28(9):1520-1524.
Cas No. | 84745-94-8 | SDF | |
别名 | 青阳参甙元 | ||
Canonical SMILES | CC([C@]1(O)CC[C@]2(O)[C@]3(O)CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])C[C@@H](OC(C5=CC=C(O)C=C5)=O)[C@]12C)=O | ||
分子式 | C28H36O8 | 分子量 | 500.58 |
溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.9977 mL | 9.9884 mL | 19.9768 mL |
5 mM | 0.3995 mL | 1.9977 mL | 3.9954 mL |
10 mM | 0.1998 mL | 0.9988 mL | 1.9977 mL |
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Identification of new Qingyangshengenin and caudatin glycosides from the roots of Cynanchum otophyllum
Steroids 2011 Sep-Oct;76(10-11):1003-9.PMID:21513722DOI:10.1016/j.steroids.2011.03.019.
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-β-D-glucopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-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).
[Chemical constituents from Xanthii Fructus]
Zhongguo Zhong Yao Za Zhi 2020 Jun;45(12):2907-2915.PMID:32627466DOI:10.19540/j.cnki.cjcmm.20200228.201.
This study was carried out to investigate the chemical constituents from Xanthii Fructus(the fruits of Xanthium sibiricum). The compounds were separated and purified by silica gel column chromatography, Sephadex LH-20 and ODS chromatography and semi-preparative HPLC. Base on HR-ESI-MS, NMR and other spectral data, their structures were identified. The anti-inflammatory activity of the isolated compounds was evaluated by lipopolysaccharide(LPS)-induced macrophage RAW264.7 as a screening model. A total of twenty-one compounds were isolated from the EtOAc fraction of 95% ethanol extract and identified as uracil(1), thymine(2), uridine(3), indole-3-carbaldehyde(4), indole-3-carboxylic acid(5), 2'-O-methyluridine(6), guanosine(7), 2,4(1H,3H)-quinazolinedione(8), 3-hydroxy-3-(2-hydroxyethyl)indolin-2-one(9), nicotinamide(10), N-acetyl-L-phenylalaninol(11), heliolactam(12), terresoxazine(13), caudatin(14), Qingyangshengenin(15), caudatin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(16), caudatin-3-O-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(17), caudatin-3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside(18), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranoside(19), qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside(20), rostratamine-3-O-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside(21). Compounds 5-21 are obtained from genus Xanthium for the first time. Compounds 12 and 13 indirectly exhibited anti-inflammatory activity by suppressing LPS-induced NO production in RAW264.7 cells with IC_(50) values of(15.45±0.56) and(20.14±0.78) μmol·L~(-1), respectively.
[Excretion of Cynanchum auriculatum extract in urine and feces of normal and functional dyspepsia rats]
Zhongguo Zhong Yao Za Zhi 2022 Dec;47(23):6355-6364.PMID:36604880DOI:10.19540/j.cnki.cjcmm.20220621.202.
In the present study, the excretion of four active components(Qingyangshengenin, deacylmetaplexigenin, baishouwu benzophenone, and scopoletin) in Cynanchum auriculatum extract in the urine and feces of normal and functional dyspepsia(FD) rats was investigated. Rats were divided into a normal group and an FD model group. The FD model was induced by oral administration of ice hydrochloric acid combined with irregular feeding. The C. auriculatum extract was administered orally at a dose of 1 g·kg~(-1). The rat urine and feces were collected at 4, 8, 12, 24, 36, 48, 60, 72, and 84 h for UPLC-ESI-MS/MS analysis. The differences in excretion of the four components were compared between normal and FD rats. The results showed that except for the baishouwu benzophenone in the feces, the components such as Qingyangshengenin in the urine and feces did not reach the plateau value within 84 h. Qingyangshengenin was mainly excreted through defecation, and the cumulative excretion rates in the normal state and FD were 0.32% and 0.66%, respectively. Deacylmetaplexigenin was mainly excreted through urination, and the cumulative excretion rates in the normal state and FD were 6.70% and 7.56%, respectively. Baishouwu benzophenone was mainly excreted through defecation in the normal state, but mainly excreted through urination in the FD state, with cumulative excretion rates of 0.41% and 0.52%, respectively. Scopoletin was mainly excreted through urination, with cumulative excretion rates of 0.83% and 2.13% in the normal state and FD, respectively. In general, the components were mainly excreted in the urine in the FD state. Compared with the normal group, the FD group showed decreased cumulative excretion rates of Qingyangshengenin, baishouwu benzophenone, and scopoletin in the urine(P<0.05). Therefore, FD had a certain influence on the excretion of the main components of C. auriculatum extract, and the excretion of each component through urination and defecation was low, suggesting that there might be a wide range of metabolic pathways after oral administration and components were mainly excreted in the form of metabolites. This experiment provides a reference for the new drug development and clinical application of C. auriculatum.
Pregnane glycosides from the antidepressant active fraction of cultivated Cynanchum otophyllum
Fitoterapia 2016 Apr;110:96-102.PMID:26944766DOI:10.1016/j.fitote.2016.02.014.
Based on the bioactive screening results, four new pregnane glycosides, namely cynanotophyllosides A-D (1-4) were isolated from the anti-depressant active fraction of cultivated Cynanchum otophyllum, along with thirteen known compounds (5-17). The new compounds were characterized as Qingyangshengenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (1), qingyangshengenin-3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (2), caudatin-3-O-β-D-glucopyranosyl-(1→4)-β-D-thevetopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-digitoxopyranoside (3) caudatin-3-O-β-D-glucopyranosyl -(1→4)-β-D-thevetopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (4), by detailed spectroscopic analysis and acidic hydrolysis.
[Intestinal absorption characteristics of root tuber of Cynanchum auriculatum extract in normal and functional dyspepsia model rats via everted intestine sac model]
Zhongguo Zhong Yao Za Zhi 2022 Jul;47(14):3915-3922.PMID:35850850DOI:10.19540/j.cnki.cjcmm.20220215.201.
The study investigated the difference of intestinal absorption characteristics of root tuber of Cynanchum auriculatum extract between normal and functional dyspepsia(FD) model rats with everted intestine sac model.The content of syringic acid, scopoletin, caudatin, baishouwu benzophenone, Qingyangshengenin and deacyhmetaplexigenin in the C.auriculatum extract in different intestinal segments was detected by UPLC-MS/MS.The cumulative absorption amount(Q) and absorption rate constant(K_a) of the six chemical constituents were calculated.The results showed that the six components could be absorbed into the intestinal sac and were unsaturated, which indicated that the absorption mechanism of scopoletin was active transport in the intestine, while that of the other five components were passive diffusion.For normal group, the syringic acid and baishouwu benzophenone in ileum, Qingyangshengenin and deacyhmetaplexigenin in ileum and duodenum, and caudatin in colon were well absorbed and scopoletin at low, medium and high concentrations was found excellent absorption in jejunum, ileum, and colon, respectively.Whereas the best absorption site of each component was ileum in model group.The absorption characteristics of each component between normal group and model group were complex at different concentrations, showing inconsistent tendency of absorption, which suggested that the components of root tuber of C.auriculatum extract were selectively absorbed in small intestine, and the absorption characteristics of the six components could be changed under FD status.This study provided theoretical basis for the clinical drug application and development of root tuber of C.auriculatum.