(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside
CAS: 29838-67-3
Molecular Formula: C21H22O11
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside - Names and Identifiers
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside - Physico-chemical Properties
| Molecular Formula | C21H22O11 |
| Molar Mass | 450.4 |
| Density | 1.74 |
| Melting Point | 180 °C (decomp) |
| Boling Point | 801.1±65.0 °C(Predicted) |
| Flash Point | 282.9°C |
| Solubility | Easily soluble in boiling water, almost insoluble in ether |
| Vapor Presure | 4.42E-27mmHg at 25°C |
| Appearance | Colorless crystal |
| pKa | 7.34±0.60(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.748 |
| MDL | MFCD20274680 |
| Physical and Chemical Properties | White crystalline powder, soluble in boiling water, almost insoluble in ether, from Smilax, Smilax, Huangqi Engelhardtia roxburghiana Wall. |
| In vitro study | Astilbin is a common dietary flavonoid that can be found in various kinds of herbs and foods such as Smilax Glabra , Sarcandra glabra , grape and red wine. Astilbin markedly inhibits cisplatin-induced cell apoptosis and recovers cell growth. Astilbin significantly decreases reactive oxygen species (ROS) accumulation and alleviates ROS-induced activation of p53, MAPKs and AKT signaling cascades, which in turn attenuates cisplatin-induced HEK-293 cell apoptosis. Astilbin effectively enhances NRF2 activation and transcription of its targeting antioxidant genes to reduce ROS accumulation in cisplatin-induced HEK-293 cells. Astilbin obviously suppresses tumor necrosis factor alpha (TNF-α) expression and NF-κB activation, and also inhibits the expression of induced nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). To measure the effects of Astilbin on the growth of CDDP-treated renal cells, HEK-293 cells are treated with CDDP (100 μM) and/or Astilbin (200 μM). Astilbin treatment significantly improvescell growth in CDDP-induced HEK-293 cells. |
| In vivo study | To explore whether Astilbin improves CDDP-induced nephrotoxicity in vivo, an acute cisplatin nephrotoxic mouse model is established. Single injection of CDDP with 8 mg/kg dose results in notable weight loss compared with control group. However, the phenomenon is significantly alleviated by Astilbin at dose of 50 mg/kg. The mice fed Astilbin alone do not show any obvious alteration in body weight. Similarly, serum creatinine (SCr) and blood urea nitrogen (BUN) are higher in CDDP-treated mice than in control group. Treatment with Astilbin also decreases SCr and BUN levels. To examine the protective effect of Astilbin on CDDP-induced renal histopathological damage, the mouse kidney sections are stained with H&E. The mice in control group and Astilbin treated group have normal kidney morphology, while kidneys in CDDP group show severe damage with tubular degeneration, necrosis and cystic dilatation of the tubules with focal hemorrhages. Administration of Astilbin mitigated kidney injury, resulting in lower histopathological score compared to CDDP group. The apoptosis of renal cells is also detected using TUNEL staining to determine whether Astilbin treatment decreased renal cell apoptosis in CDDP-induced acute nephrotoxic mice. |
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside - Risk and Safety
| Hazard Symbols | N - Dangerous for the environment |
| Risk Codes | 50 - Very Toxic to aquatic organisms |
| Safety Description | 61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 3 |
| HS Code | 29389090 |
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside - Reference
| Reference Show more | 1. Jiang Xuanyu, Wang Siwei, Lou Lijun, etc. Effect of astilbin, an active molecule of Smilax glabra, on apoptosis of human renal tubular epithelial cells induced by cisplatin [J]. Zhejiang Journal of Integrated Traditional Chinese and Western medicine, 2018, 28(09):735-738. 2. Wang Siwei, Zhang Feng, Zheng Xiaoyan, etc. Effect of astilbin combined with cisplatin on apoptosis of human lung cancer A549 cells [J]. Chinese herbal medicine, 2017, 26 (12). 3. Zhao Ruizhi, Shi changcan, Liu Lijuan, etc. Pharmacokinetics evaluation of sustained-release tablets of Shiling Xiaoyin in Beagle dogs [J]. Chinese Journal of Hospital Pharmacy, 2017, 11(v.37):17-19. 4. Huang Huihui, Zhang Xiaoyan, Shen Juan, etc. Absorption characteristics of anti-inflammatory active fractions of Smilax China L. In rat intestinal eversion test [J]. Chinese Journal of Experimental prescriptions, 2016, v.22(08):96-99. 5. Xu Ping, Zhang Miao, Xu Yubin, Mao Xunan, Zhang Peijian. Effects of astilbin preconditioning on hepatic ischemia-reperfusion injury and expression of Bcl-2 and Bax in rats [J]. China pharmacist, 2016,19(11):2055-2058. 6. Wang Yinjie, Zhao Ruizhi, Lu Chuanjian. Comparison of pharmacokinetics of astilbin in rats between yinxieling and Smilax glabra [J]. Chinese Journal of Traditional Chinese Medicine, 2012, 37(12):1859-1861. 7. Zhou, Jing, Chen, Hui, Peng, et al. Simultaneous determination of seven components in Jiawei ermiao granules by HPLC and establishment of fingerprint [J]. Chinese patent medicine 2018 v.40(02):99-104. 8. Feng Limin, Zhao Ruizhi, Lu Chuanjian. Simultaneous determination of paeoniflorin, astilbin, chlorogenic acid, rosmarinic acid and glycyrrhizic acid in Shiling Xiaoyin tablets by HPLC [J]. Chinese Journal of Modern Applied Pharmacy, 2014 031(009):1097-1101. 9. Pan, Xin, Xin, Lin, Qing, Zhou Chuchu, etc. Simultaneous determination of nine effective components in sarcandra glabra by HPLC [J]. Journal of Pharmaceutical Analysis, 2017, 037(007):1207-1214. 10. Yang Junjie, Huang Ziyan, Li Lin, et al. Optimization of integrated processing technology for Smilax glabra [J]. Shi Zhen, National Medicine, 2018, 29(09):2165-2168. 11. Yang Junjie, Zhang Yanling, Wang Xiaotao, Lu Jiulin. Analysis on the rationality of peeling in the processing of Smilax glabra [J]. Chinese Journal of Experimental prescriptions, 2017,23(03):1-5. 12. Zhao Ruizhi, Wang Yinjie, Feng Limin, Lu Chuanjian. Pharmacokinetics of paeoniflorin, astilbin, rosmarinic acid, isoazepidine and liquiritin in rats after oral administration of Shiling Xiaoyin tablets [J]. Chinese Journal of Traditional Chinese Medicine, 2014,39(13):2559-2563. 13. Feng Limin, Zhao Ruizhi, Wang Yinjie, etc. Optimization of extraction process for the effective components of sarcandra glabra in yinxieling tablets by orthogonal design [J]. Shi-zhen, National Medicine, 2011(08):1860-1861. 14. Wang Mengxue, Dai Hanpeng, Li Jinming, Su Ya, Han Xinran, Li Li. Inhibition of CYP3A4 activity by Smilax glabra [J]. Journal of Changchun Normal University, 2020,39(08):60-63. 15. Sun, Xiaoqi, et al. "Caspase-dependent mitochondrial apoptotic pathway is involved in astilbin-mediated cytotoxicity in breast carcinoma cells." Oncology reports 40.4 (2018): 2278-2286.https://doi.org/10.3892/or.2018.6602 16. Yang, Mao, et al. "Astilbin influences the progression of osteoarthritis in rats by down-regulation of PGE-2 expression via the NF-κB pathway." Annals of Translational Medicine 8.12 (2020).https://dx.doi.org/10.21037/atm-20-4485 17. Wang, Si-wei, et al." Astilbin ameliorates cisplatin-induced nephrotoxicity through reducing oxidative stress and inflammation." Food and chemical toxicology 114 (2018): 227-236.https://doi.org/10.1016/j.fct.2018.02.041 18. Hui Bi, Zhen Sun, Qiubo Chu, Lanzhou Li, Xin Guan, Yulin Zhou & Zhiwen Li (2019) Analgesic effects of astilbin partially via calcium channels through regulation on CaMKII Food and Agricultural Immunology, 30:1, 309-319, DOI: 10.1080/09540105.2019.1580677 19. Duan, Qianni, et al. "Antiviral effect of Chinese herbal prescription JieZe-1 on adhesion and penetration of VK2/E6E7 with herpes simplex viruses type 2." Journal of ethnopharmacology 249 (2020): 112405.https://doi.org/10.1016/j.jep.2019.112405 20. [IF=4.36] Yueqin Cai et al."Medicinal effect and its JP2/RyR2-based mechanism of Smilax glabra flavonoids on angiotensin II-induced hypertrophy model of cardiomyocytes."J Ethnopharmacol. 2015 Jul;169:435 21. [IF=3.906] Xiaoqi Sun et al."Caspase-dependent mitochondrial apoptotic pathway is involved in astilbin-mediated cytotoxicity in breast carcinoma cells."Oncol Rep. 2018 Oct;40(4):2278-2286 22. [IF=3.775] Si-wei Wang et al."Astilbin ameliorates cisplatin-induced nephrotoxicity through reducing oxidative stress and inflammation."Food Chem Toxicol. 2018 Apr;114:227 23. [IF=2.398] Hui Bi et al."Analgesic effects of astilbin partially via calcium channels through regulation on CaMKII."Food Agr Immunol. 2019;30(1):309-319 24. [IF=6.529] Xue Chen et al."Dendrobium officinalis six nostrum ameliorates urate under-excretion and protects renal dysfunction in lipid emulsion-induced hyperuricemic rats."Biomed Pharmacother. 2020 Dec;132:110765 25. [IF=4.225] Wen Xianghui et al."Qu-Zhuo-Tong-Bi Decoction Alleviates Gouty Arthritis by Regulating Butyrate-Producing Bacteria in Mice."Front Pharmacol. 2021 Feb;11:2508 26. [IF=3.69] Qianni Duan et al."Antiviral effect of Chinese herbal prescription JieZe-1 on adhesion and penetration of VK2/E6E7 with herpes simplex viruses type 2."J Ethnopharmacol. 2020 Mar;249:112405 27. [IF=3.297] Mao Yang et al."Astilbin influences the progression of osteoarthritis in rats by down-regulation of PGE-2 expression via the NF-κB pathway."Ann Transl Med. 2020 Jun; 8(12): 766 28. [IF=1.216] Han Yan et al."Studies on the Anti-Gouty Arthritis and Anti-hyperuricemia Properties of Astilbin in Animal Models."Open Chem. 2020 Jan;18(1):207-214 29. [IF=5.396] Tingwei Wang et al."Astilbin from Smilax glabra Roxb. alleviates high-fat diet-induced metabolic dysfunction."Food Funct. 2022 Apr ;: |
(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside - Reference Information
| physiological effects | Smilax glabra Roxb., a Liliaceae plant, is a dried rhizome of Smilax glabra Roxb., which is a commonly used Chinese herbal medicine and has the effects of dehumidification and detoxification. Taxus leaf 3-O rhamnoth methyl ester (astilbin) is a flavonoid compound isolated from Smilax glabra. It has insecticidal, coenzyme A reductase, aldose reductase, hepatoprotective, analgesic, anti-edema, antioxidant and other active effects. Taxus leaf 3-O rhamnyl methyl ester can also significantly improve immune liver injury, induce apoptosis of PHA-activated Jurkat cells, inhibit delayed hypersensitivity and treat collagen arthritis in mice by inhibiting the function of activated T lymphocytes. |
| biological activity | Astilbin is a flavonoid compound that can be separated from the rhizome of Smilax glabra. Astilbin enhanced NRF2 activation. Astilbin also inhibited TNF-α expression and NF-κB activation. |
| use | astiloside has the effects of protecting liver, analgesia and anti-edema. used for content determination/identification/pharmacological experiment, etc. Pharmacological effects: It can inhibit coenzyme A reductase, inhibit aldose reductase, protect liver, relieve pain, anti-edema, etc. In recent years, it has been reported that astilin has a significant selective immunosuppressive effect, and its selective effect has obvious advantages compared with previous immunosuppressants, so it can be used as a new immunosuppressant for the treatment of immune-related diseases. |
Last Update：2024-04-09 02:00:08
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Product Name: Astilbin Visit Supplier Webpage Request for quotationCAS: 29838-67-3
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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Product Name: Astilbin Visit Supplier Webpage Request for quotationCAS: 29838-67-3
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
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