Spirost-5-en-3-ol, (3β,25S)-
yamogenin
CAS: 512-06-1
Molecular Formula: C27H42O3
Spirost-5-en-3-ol, (3β,25S)- - Names and Identifiers
| Name | yamogenin |
| Synonyms | Yamogenin yamogenin Diosgenin Nsc 226132 NSC 226132 Neodiosgenin (25S)-Spirost-5-en-3β-ol Spirost-5-en-3-ol, (3β,25S)- (3beta,25S)-spirost-5-en-3-ol Spirost-5-en-3-ol, (3beta,25S)- (20Α,22R,25S)-Spirosta-5-Ene-3Β-Ol (20α,22R,25S)-Spirosta-5-ene-3β-ol |
| CAS | 512-06-1 |
| EINECS | 208-134-3 |
| InChI | InChI=1/C27H42O3/c1-16-7-12-27(29-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(28)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28H,6-15H2,1-4H3/t16-,17-,19-,20+,21-,22-,23-,24-,25-,26-,27+/m0/s1 |
Spirost-5-en-3-ol, (3β,25S)- - Physico-chemical Properties
| Molecular Formula | C27H42O3 |
| Molar Mass | 414.62 |
| Density | 1.13g/cm3 |
| Melting Point | >180°C (dec.) |
| Boling Point | 527.1°C at 760 mmHg |
| Specific Rotation(α) | -123 |
| Flash Point | 272.6°C |
| Solubility | Ethanol : 10 mg/mL (24.12 mM; Need ultrasonic) |
| Vapor Presure | 2.59E-13mmHg at 25°C |
| Appearance | Powder |
| Color | White to Pale Beige |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.564 |
| MDL | MFCD20377911 |
Spirost-5-en-3-ol, (3β,25S)- - Reference
| Reference Show more | 1. Liu, Mengshun, et al. "Folding fan mode counter-current chromatography offers fast blind screening for drug discovery. Case study: Finding anti-enterovirus 71 agents from Anemarrhena asphodeloides." Journal of Chromatography A 1368 (2014): 116-124.https:// 2. [IF=5.753] Jianghong Gao et al."Molecular Cloning and Functional Characterization of a Sterol 3-O-Glucosyltransferase Involved in Biosynthesis of Steroidal Saponins in Trigonella foenum-graecum.."Front Plant Sci. 2021 Dec;12:809579-809579 |
Spirost-5-en-3-ol, (3β,25S)- - Reference Information
| overview | diosgenin (diosgenin) is commonly known as saponin. it is a kind of steroidal saponin naturally synthesized by plants and belongs to spirostanol glycosides (fig. 1). its structural formula is C27H42O3 and its relative molecular mass is 414.63. it is widely found in legume and dioscorea plants. The main source of diosgenin is the seeds of fenugreek Trigonella foenum-graecum l, it can also be extracted from tubers of Dioscorea zingiberensis C. H. Wright of Dioscorea zingiberensis, D. nipponica Makino of Dioscorea zingiberensis, D. panthaica Prain et Burkill of Dioscorea zingiberensis, D. nipponica Makino ssp. rosthornii (Prain et Burkill) C. T. Tin and other plants by hydrolysis, fermentation, extraction and other methods [2]. diosgenin is an important basic raw material for the production of steroid hormone drugs. Steroid hormones have strong anti-infection, anti-allergy, anti-virus and anti-shock pharmacological effects. They are important for the treatment of rheumatism, cardiovascular, lymphatic leukemia, cellular encephalitis, skin diseases, anti-tumor and rescue of critically ill patients Medication. diosgenin (diosgenin), as an important natural steroidal sapogenin, has a wide range of sources and is mainly obtained from cucurbita. It is an important raw material for the synthesis of steroid hormone drugs. It has many significant pharmacological effects such as anti-tumor, anti-inflammatory and anti-oxidation, and has high medicinal value. |
| preparation method | is obtained by hydrolysis and extraction using chuandi dragon crude medicine or turmeric as raw materials. Chinese chemist Huang Minglong and others used diosgenin as raw material and successfully synthesized cortisone with a seven-step reaction. Different preparation methods of diosgenin. Among them, the improved methods using auxiliary methods such as ultrasound, microwave or enzymatic hydrolysis have not completely separated from the process of acidolysis, causing certain pollution to the environment; and the method of preparing diosgenin by microbial fermentation has mild reaction conditions and by-products. The characteristics of less, no pollution, etc., provide a new idea for the production of diosgenin. Microbial fermentation method Microbial fermentation method has mild conditions, no acidolysis process, no pollution, and clear target product. Dong Yuesheng and others will be screened out can hydrolyze dioscorea saponin to produce aglycone Trichoderma and Aspergillus oryzae, directly connected to the raw material Dioscorea zingiberensis culture fermentation, so as to prepare diosgenin. The yield of diosgenin in this method is 1-2 times that of general acidolysis and microwave-assisted method, and acidolysis is not required. Zhang Chuan will wait for feeding. The microbial transformation of strain YM32139 and rhizome of yellow yam was studied by solid transformation. The results showed that the original components in yellow yam were mainly converted into diosgenin. Yu Dong et al. screened a strain that efficiently transforms to produce diosgenin, and carried out liquid fermentation with Dioscorea zingiberensis, and optimized the fermentation conditions. The highest conversion rate reached 85%. With the deepening of the research on diosgenase, a variety of different strains have been screened out from microorganisms. These strains can secrete proteases that are transformed into diosgenin. The reaction conditions, purification and properties of the enzymes have also been further studied. |
| Anti-tumor effect | In vitro and in vivo studies have shown that diosgenin is cytotoxic to a variety of tumor cells, including breast cancer cells, colon cancer cells, prostate cancer cells, lung cancer cells, gastric cancer cells, osteosarcoma cells, etc, it can play an anti-tumor effect by inhibiting tumor cell proliferation, inducing tumor cell apoptosis, blocking cell cycle and anti-tumor metastasis. From the anti-tumor pharmacological effects of diosgenin and its mechanism research, it can be seen that diosgenin has anti-colon cancer, prostate cancer, breast cancer, liver cancer, gastric cancer, oral cancer and skin cancer and other tumors. Summarizing the possible mechanism of diosgenin's anti-tumor effect (Figure 1), it can be seen that diosgenin plays an anti-tumor effect by adjusting a variety of cell signaling pathways, and is closely related to many important molecular targets such as growth, differentiation, apoptosis, and tumor formation. Figure 1 The possible anti-cancer mechanism of diosgenin at the cellular level |
| use | this product is an important steroidal sapogenin and an important raw material for semi-synthetic steroidal compounds. Diosgenin is subjected to ring-opening, oxidation, hydrolysis and elimination reactions to obtain pregnenone alcohol. After oximation, rearrangement and hydrolysis, dehydroepiandrosterone can be prepared. These intermediates have important value in drug production. |
| References | [1] Diosgenin. Bailian Database. [Citation Date 2017.09.09] [2] He Yan, Wang Jishuang, Zhang Peng, Hua Zichun. Research Progress on Pharmacological Effects and Mechanisms of Diosgenin [J]. Chinese Herbal Medicine, 2013,44(19):2759-2765. [2017-09-09]. [3] Zhao Min, Tan Dawei, Yu River, Kang Liping, Zhou Wenbin, Xiong Chengqi, Zhao Yang, ma Baiping. Research Progress on Preparation Methods of Diosgenin [J]. Chinese Herbal Medicine, 2013,44(13):1860-1866. [2017-09-09]. |
| Biological activity | Yamogenin (Neodiosgenin) is a diastereomer of diosgenin. Yamogenin (Neodiosgenin) antagonizes liver X receptor (LXR) activation in luciferase ligand determination. Yamogenin (Neodiosgenin) inhibits triglyceride (TG) accumulation by inhibiting gene expression of fatty acid synthesis in HepG2 hepatocytes. |
| target | IC50: TG accumulation; liver X receptor (LXR) |
Last Update：2024-04-09 20:44:15
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