delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol
Solasodine
CAS: 126-17-0
Molecular Formula: C27H43NO2
delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol - Names and Identifiers
| Name | Solasodine |
| Synonyms | HSDB 3538 Solasodin Salasdine SOLASODINE Solasodine Salasodine NSC 178260 NSC 179187 BRN 0094578 Solanidine-S PURAPURIDINE Purapuridine Solancarpidine SOLANCARPIDINE Solanum nigrum L. spirosol-5-en-3-ol Solasod-5-en-3beta-ol SOLASOD-5-EN-3BETA-OL Solasod-5-en-3-beta-ol (3beta)-spirosol-5-en-3-ol Solasodine HYDROCHLORIDE BASE (3beta,25R)-spirosol-5-en-3-ol (3beta,22alpha,25r)-spirosol-5-en-3-o (3beta,22alpha,25R)-spirosol-5-en-3-ol Spirosol-5-en-3-ol, (3beta,22alpha,25R)- 4-27-00-02000 (Beilstein Handbook Reference) (3beta,8xi,9xi,17xi,22alpha,25R)-spirosol-5-en-3-ol delta5-20betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol |
| CAS | 126-17-0 |
| EINECS | 204-774-2 |
| InChI | InChI=1/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17+,19+,20?,21?,22+,23+,24?,25+,26+,27-/m1/s1 |
| InChIKey | KOZCINYDCJVLDW-GCGBSLFCSA-N |
delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol - Physico-chemical Properties
| Molecular Formula | C27H43NO2 |
| Molar Mass | 413.64 |
| Density | 1.0159 (rough estimate) |
| Melting Point | 200-202° |
| Boling Point | 532.75°C (rough estimate) |
| Specific Rotation(α) | D25 -98° (c = 0.14 in methanol); D -113° (CHCl3) |
| Flash Point | 279.1°C |
| Solubility | Soluble in benzene, pyridine and chloroform, soluble in ethanol, methanol and acetone, slightly soluble in water, insoluble in ether. |
| Vapor Presure | 8.21E-14mmHg at 25°C |
| Appearance | Flake crystallization |
| Color | white to beige |
| pKa | pKb 6.30(at 25℃) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.6400 (estimate) |
| MDL | MFCD00037844 |
| Physical and Chemical Properties | Soluble in benzene, pyridine and chloroform, soluble in ethanol, methanol and acetone, slightly soluble in water, insoluble in ether from Solanum Solanum aviculare Forst. Fruit; Solanum nigrum L. Fruit; Solanum Solanum lyratum Thunb. Whole grass; Capsicum annuum seeds. |
delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| RTECS | WF1300000 |
delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol - Reference
| Reference Show more | 1. He Ziqian, Peng Qing, Cai Daolin, et al. Antioxidant and Anti-inflammatory Activities of Alcohol Extracts of Urtica angustifolia in Vitro [J]. Modern Food Science and Technology, 2018, v.34;No.228(08):42-49 135. 2. [IF = 2.289] Zhou Shun et al."Anthelmintic efficacy of natural saponins against Gyrodactylus kobayashii in goldfish (Carassius auratus) and their 3D-QSAR analysis." Parasitol Res. 2021 Mar;120(3):1143-1150 |
delta5-20Betaf,22alphaf,25alphaf,27-azaspirosten-3beta-ol - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| overview | Australian solanide (solasodine) is an important steroidal alkaloid extracted from the green fruits of Solanum (Solanum sodomeum). Australian solanine can combine with different glycosides and different numbers of glycosides to form various glycoside alkaloids. The two glycoside alkaloids of Australian solanine (solamargine) and Australian solanine (solasonine) are the main forms of Australian solanine in plants. Pharmacological activity, especially strong anti-tumor activity. SBP002(Coramsine) is an equivalent mixture of solanine and solanine. It was developed by Solbec Australia. As a drug for the treatment of mesothelioma and melanoma, it has completed Phase II B clinical practice in Australia and the United States. In addition, macadamine is an important precursor for the synthesis of a variety of steroid hormones, such as the synthesis of cortisone, progesterone, and pregnancy dienolone acetate. Figure 1: Australian Solanamine |
| Source | Australian solanamine is found in the leaves and fruits of about 250 species of Solanum plants. In my country, Australian solanamine is mainly found in the fruits of Australian solanum, bitter solanum, white English and Solanum nigrum. Among them, Solanum nigrum is also a traditional anti-tumor Chinese medicine. It is widely distributed in my country. The plant is rich in various steroids. Alkaloids, such as solanine, solanine, etc., these steroid alkaloids exist in the form of glycosides in its stems, leaves, roots, and fruits, alycone is macadamia. |
| Pharmacological activity | Solanine is a potential steroid and hormone precursor, usually found in Solanaceae plants. It also has powerful cytotoxic and anti-inflammatory effects. Anti-tumor: Studies have found that macadamine has anti-tumor, antibacterial, anti-inflammatory and other pharmacological activities. At present, its anti-tumor activity is the most studied. When solanamine is incubated with tumor cells for 48 hours, solanamine can obviously inhibit the proliferation of tumor cells. When solanamine with a concentration of 500 μmol • L- 1 is incubated for 24 hours, most tumor cells stagnate in G0/G1 phase, and the number of cells in sub-G1 phase is very small. Therefore, it is believed that solanamine does not achieve anti-cancer effect by inducing apoptosis of cancer cells, instead, it exerts its activity by inhibiting cell proliferation. However, it is also found that macadamine can not only inhibit the proliferation of human osteosarcoma cells, but also induce tumor cell apoptosis. In addition, the glycoside alkaloids of solanamine can inhibit the growth of human skin cancer and solanamine hydrochloride (SBHL) HeLa cells, and with the increase of its concentration and the extension of the action time, the inhibitory effect is enhanced. SBHL may have dual effects of inhibiting DNA synthesis in HeLa cells and inducing apoptosis in HeLa cells. Because of its small toxicity, stable nature and good solubility, it has been developed as a class of anticancer drugs. Antifungal: It has been found that solanamine has significant inhibitory activity on Staphylococcus aureus, with MIC of 62.5mg • L- 1, which is stronger than the positive control drug streptomycin, while it has weak inhibitory activity on Bacillus subtilis, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa, with MIC greater than 1,000 mg • L- 1. Ketoconazole can inhibit the biosynthesis of ergosterol, an essential component of fungal cell membrane, and has antifungal activity similar. Anti-inflammatory and analgesic: BHL also has strong anti-inflammatory activity. The macadamine extracted and isolated from Solanum nigrum was prepared into hydrochloride, and it was found that it can inhibit the swelling of mouse feet induced by carrageenan and can significantly resist the granuloma of rats caused by cotton balls. In addition, the salts of macadamine organic acids (such as formic acid, acetic acid, gallic acid, etc.) also show anti-inflammatory activity. The macadamine organic acid salts are made into injections, capsules and tablets for pneumonia, tuberculosis, mastitis, and tonsillitis. Patients with inflammation, pharyngitis, and tracheitis also showed significant effects. Scavenging free radicals in the body: Excessive production of free radicals or decreased ability to scavenge free radicals are closely related to the occurrence of inflammation, tumors, aging, blood diseases, and various diseases such as the heart, liver, lungs, and skin. The role of free radicals may reduce the risk of these diseases. The antioxidant activity of macadamine isolated from berries was found to have scavenging rates of DPPH and ABTS radicals of 55.7% and 85.72% respectively. |
| Toxicology | Studies have found that macadalamine is teratogenic and can cause spina bifida, craniofacial deformities, brain exposure, and no eyes. And the toxic side effects of rabbit lips. The reason may be that the 5,6 unsaturated double bond in the structure of maladine is beneficial for maladine to bind more stably to the receptor or the α,β-unsaturated ketones produced by the metabolism of unsaturated double bonds can make maladine It is easier to bind to the corresponding receptor. In addition, it has been found that macadamines can reversibly cause the adverse effects of liver enlargement in mice. |
| Synthesis | The research on the chemical synthesis of macadamine began in the 50s, and there have been many reports on its chemical synthesis methods. Uhle et al. used lily of the valley sapogenin (kryptogenin) as raw material, and synthesized macadamine in a total yield of 4.8% through a 7-step reaction. The synthesis route is shown in the figure. The yield of macadamine prepared by this route is low, and the sapogenin of lily of the valley as a raw material is expensive. A new method for the synthesis of macadamine was reported later. They used diosgenin as the raw material, and the pseudo-diosgenin was used to prepare macadamine in a 5-step reaction with a yield of 24%. The synthesis route is shown in the figure. The route of this method is simple and the yield is high. More importantly, this synthetic route can also be used for structural modification and modification of macadamine, which is of great significance for subsequent research on biological activity and mechanism of action. figure 2: roadmap for synthesis of macadamine figure 3: new roadmap for synthesis of macadamine |
| analysis method | Solanum nigrum alkaloids mainly exist in the form of alkaloid glycosides. Due to the corresponding relationship between aglycones and alkaloid glycosides, it is a common analysis method to quantify Solanum nigrum alkaloids by aglycones. Solanine (solasonine) and solanine (solamargine) are the main active ingredients of Solanum nigrum, and their hydrolyzed aglycones are solanum. The determination of macadamine is often used to quantify Solanum nigrum alkaloids, including gravimetric method, potentiometric titration, colorimetric method and thin layer scanning method [. However, these methods are cumbersome to operate and have poor accuracy. In recent years, high performance liquid chromatography (HPLC) has become a powerful analytical tool for the complex system of traditional Chinese medicine by virtue of its excellent separation ability. Based on the analysis of macadamine, a high performance liquid chromatography method for the determination of total alkaloids of steroidal organisms in Solanum nigrum was proposed. figure 4: analysis test |
| summary | macadamine has a variety of pharmacological activities, especially has the effect of inhibiting cell proliferation on a variety of tumor cells, and has great clinical research value. Solanamine hydrochloride has small side effects, high bioavailability and stable properties, and has clinical application value. |
| references | [1] Chen lei, cha Xiaoming, Jiang zhenzhou, et al. research progress of steroidal alkaloid macadamine [J]. pharmaceutical progress, 2011, 35(6):257-264. [2] Cui Changzhi. Design, Synthesis and Preliminary Activity of Solanamine Derivatives [D]. Shandong University, 2012. [3] Luo Xizhen, Chen Lai, Liu Jianjun, et al. Determination of Solanum in Solanum nigrum by High Performance Liquid Chromatography [J]. Shi Zhen Guo Yi Guo Yao, 2009, 20(2):273-274. [4] Jin Dezhong. Study on the Inhibitory Effect of Solanum nigrum Extract on Lung Cancer Cells [D]. Nanchang University, 2014. [5] Zhuang Yuwen, Zhou Jinyong, Wu Jian, et al. Experimental Study on Apoptosis of Colorectal Cancer HCT-116 Induced by Solanum nigrum [J]. Journal of Nanjing University of Traditional Chinese Medicine, 2017, 33(1):69-73. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: antipyretic and anti-inflammatory effects. A neuroprotective antioxidant glycoalkaloid can increase the levels of superoxide dismutase (SOD), catalase (CAT) and glutathione (GSH) in brain tissue and reduce the levels of lipid peroxidation (LPO) and nitric oxide (NO) in cerebral ischemia-reperfusion (I/R) injury model in rats. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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