19057-60-4 Usage
Description
Dioscin is extracted from Dioscorea nipponica. Rhizoma Dioscoreae Nipponicae is
the dry rhizome of this plant. It can be orally used to treat joint pain, arthritis,
malaria, and chronic bronchitis. In addition, it can also be used externally to treat
sore carbuncle swollen. Rhizoma Dioscoreae Nipponicae is commonly used in the
northeast region, Shanxi province, and Shandong province of China.
Physical properties
Appearance: white powder. Solubility: insoluble in water, petroleum ether, and benzene; soluble in methanol, ethanol, and acetic acid; slightly soluble in acetone and
amyl alcohol. Melting point: 294–296℃. Specific optical rotation: ?115°
(c?=?0.373, ethanol).
History
Japanese scientists firstly reported and analyzed the structure of dioscin isolated
from the saponins of Japanese Dioscoreaceae. V . However, the biological activities of dioscin have not attracted the interests of scientists until the late 1990s and
the beginning of this century. It is now believed that dioscin may have therapeutic
effects on reducing blood lipids and protecting the liver, as well as antivirus, antiinflammatory, and antitumor effects. After the implementation of standardization of
traditional Chinese medicine, dioscin as the quality control specification of
Dioscorea nipponica Makino and other traditional Chinese medicine has attracted
more attentions and researches. In China, dioscin tablets have been used to treat
hyperlipidemia in the clinical practice. However, no corresponding drugs are available on the market in other countries. In addition, dioscin is also an important predecessor for synthesizing steroid hormones . Dioscorea nipponica Makino,
which is used to extract dioscin, primarily comes from wild plants, whose resources
are limited.
Uses
Different sources of media describe the Uses of 19057-60-4 differently. You can refer to the following data:
1. Dioscin, a natural steroid saponin that has been shown to promote anticancer activity against several forms of cancers. Dioscin induces cancer cell apoptosis through elevated oxidative stress mediated by downregulation of peroxiredoxins.
2. Dioscin, a natural steroid saponin that has been shown to promote anticancer activity against several forms of cancers. Dioscin induces cancer cell apoptosis through elevated oxidative stress mediated
by downregulation of peroxiredoxins.
Indications
This drug was recorded in the national standards for chemical drugs, volume 5.
Dioscin tablets, containing total dioscin, are used to treat coronary heart disease,
coronary insufficiency, as well as control hyperlipidemia.
Pharmacology
Studies showed that compound preparations containing dioscin can increase coronary blood flow, reduce myocardial oxygen consumption, and protect myocardial
ischemia and ischemia-reperfusion injury, which is beneficial for alleviating myocardial ischemia and angina. In addition, dioscin can regulate the lipid metabolism
and improve hemodynamics. Dioscin can also prevent atherosclerosis by reducing
serum total cholesterol, triglyceride, low-density lipoprotein, and oxidized lowdensity lipoprotein, reducing the whole blood viscosity and plasma viscosity at high
and low shear rates, and relieving arterial wall lipid infiltration and plaque formation. Furthermore, dioscin can reduce liver fat deposition, which may be related to
promoting cholesterol secretion metabolism.It has also been reported that dioscin can induce the apoptosis of a variety of
tumor cells, including gastric cancer cells, breast cancer cells, lung cancer cells, oral
squamous cell carcinoma, and cervical cancer cells. The mechanisms are related to
reducing the oxidative stress and inhibiting some cellular survival signaling pathways Dioscin can induce antioxidant enzymes, lower blood lipids, improve insulin
resistance, inhibit the inflammatory response, reduce the damage of alcoholic hepatitis, and decrease the hepatic injury induced by acetaminophen .
Check Digit Verification of cas no
The CAS Registry Mumber 19057-60-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,0,5 and 7 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 19057-60:
(7*1)+(6*9)+(5*0)+(4*5)+(3*7)+(2*6)+(1*0)=114
114 % 10 = 4
So 19057-60-4 is a valid CAS Registry Number.
InChI:InChI=1/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27?,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
19057-60-4Relevant articles and documents
Synthesis of novel diosgenyl saponin analogs and evaluation effects of rhamnose moeity on their cytotoxic activity
Meng, Xin,Pan, Yiwu,Liu, Tao,Luo, Chen,Man, Shuli,Zhang, Yongmin,Zhang, Yan
, (2021)
Diosgenyl saponins, as a type of natural products derived from plants, are the main active component of traditional chinese medicine. Inspiringly, a large number of natural diosgensyl saponins have been shown to exert excellent toxicity to hepatocellular cancer (HCC) cells. In order to better understand the relationship between the structures and their biological effects, a group of diosgenyl saponins (1–4 as natural products and 5 and 6 as their analogs) were efficiently synthesized. The cytotoxic activity of these compounds was evaluated on human hepatocellular carcinoma (HepG2) cells. Structure–activity relationship studies showed that the pentasaccharide or hexasaccharide saponin analogs were relatively less active than their corresponding disaccharide analogue or dioscin. The extension of 4-branched rhamnose moiety on these saponin does not exhibit significant effect on their cytotoxic activity, which disclosed that a certain number and the linkage mode of rhamnose moieties could influence the cytotoxicity of steroid saponins on HepG2 cells.
Steroidal glycoside-protodioscin from Digitalis ciliata
Gvazava,Kukoladze
, p. 614 - 615 (2006)
-
N-Pentenyl-Type Glycosides for Catalytic Glycosylation and Their Application in Single-Catalyst One-Pot Oligosaccharide Assemblies
Zu, Yujia,Cai, Chenglin,Sheng, Jingyuan,Cheng, Lili,Feng, Yingle,Zhang, Shengyong,Zhang, Qi,Chai, Yonghai
supporting information, p. 8270 - 8274 (2019/10/14)
We have developed a new type of n-pentenyl-type glycosides that can be activated by catalytic amounts of promoter, Hg(NTf2)2 or PPh3AuCl/AgNTf2, at room temperature. The mild activation conditions and outstanding stability of common protection/deprotection manipulations enable the enynyl donors to have broad applications in constructing various glycosidic bonds. Furthermore, under the Hg(NTf2)2-catalyzed conditions, the sequential activation of different types of donors was achieved, based on which a gentiotetrasaccharide was synthesized via the newly developed single-catalyst one-pot strategy.
Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity
Miyashita, Hiroyuki,Kai, Yuuki,Nohara, Toshihiro,Ikeda, Tsuyoshi
, p. 1309 - 1315 (2008/09/21)
Natural steroidal glycosides containing α-l-rhamnopyranosyl-(1→4)-[α-l-rhamnopyranosyl-(1→2)]-β-d-glucopyranose (chacotriose) at the oligosaccharide moiety exhibit anti-cancer and anti-herpes activities. To investigate the structure-activity relationships of the aglycone parts of chacotriosides, we developed a synthesis method for chacotriosyl glycosides having various aglycones. In the process, it was revealed that α-chacotriosyl glycosides could be obtained mainly by using a trichloroacetimidate donor, while β-chacotriosyl glycosides were afforded by using phosphite and phosphate donors. In cytotoxicity tests using the A549 and HepG2 cell lines, naturally occurring β-chacotriosyl diosgenin and cholestanol exhibited higher activities than the corresponding α-chacotriosyl glycosides.