(3beta,16alpha)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl-beta-D-galactopyranoside
Saikosaponin D
CAS: 20874-52-6
Molecular Formula: C42H68O13
(3beta,16alpha)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl-beta-D-galactopyranoside - Names and Identifiers
| Name | Saikosaponin D |
| Synonyms | saikosaponin saikosaponins Saikosaponin D SAIKOSAPONIN D Saikosaponian D sailkosaponin D SAILKOSAPONINS D (3b,4a,16a)-13,28-Epoxy-16,23-dihydroxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl beta-D-galactopyranoside (3beta,16alpha)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl-beta-D-galactopyranoside beta-D-galactopyranoside, (3beta,16alpha)-13,28-epoxy-16,23-dihydroxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl- (3beta,13alpha,16alpha,17alpha)-16,23-dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl-beta-D-galactopyranoside |
| CAS | 20874-52-6 |
| InChI | InChI=1/C42H68O13/c1-21-28(46)33(55-34-31(49)30(48)29(47)22(18-43)53-34)32(50)35(52-21)54-27-10-11-37(4)23(38(27,5)19-44)8-12-39(6)24(37)9-13-42-25-16-36(2,3)14-15-41(25,20-51-42)26(45)17-40(39,42)7/h9,13,21-35,43-50H,8,10-12,14-20H2,1-7H3/t21-,22-,23-,24-,25-,26-,27+,28+,29-,30+,31-,32-,33+,34+,35+,37+,38+,39-,40+,41-,42+/m1/s1 |
(3beta,16alpha)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl-beta-D-galactopyranoside - Physico-chemical Properties
| Molecular Formula | C42H68O13 |
| Molar Mass | 780.99 |
| Density | 1.36±0.1 g/cm3(Predicted) |
| Melting Point | 212～218℃ |
| Boling Point | 893.7±65.0 °C(Predicted) |
| Specific Rotation(α) | (EtOH)+37 |
| Flash Point | 494.3°C |
| Solubility | Slightly soluble in water |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White powder |
| Color | White to Off-White |
| pKa | 12.83±0.70(Predicted) |
| Storage Condition | Hygroscopic, Refrigerator, Under inert atmosphere |
| Stability | Hygroscopic |
| Refractive Index | 1.616 |
| MDL | MFCD09028095 |
| Physical and Chemical Properties | Light yellow crystal, soluble in water, dilute alcohol, insoluble in benzene, ether, chloroform, derived from the above-ground part of Bupleurum. |
(3beta,16alpha)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl-beta-D-galactopyranoside - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| RTECS | VN3099000 |
| HS Code | 29389090 |
(3beta,16alpha)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl-beta-D-galactopyranoside - Reference
| Reference Show more | 1. Cheng Yupeng, Wang Hongyue, Gao Ning, et al. Determination of Total Saponins in Bupleurum and Endophytic Fungi Co-cultured [J]. Chemical Engineer, 2018, v.32;No.279(12):23-25. 2. Zhang Na, Yan Ni, Zhou Mengen, et al.. Effect of saikosaponin d on ROS formation and NLRP3 inflammatory body expression after oxidative stress-induced activation of human hepatic stellate cells [J]. Shi Zhen Guo Yi Guo Yao, 2020(4):805-809. 3. Xin Guo Zhao Xintong Li Wen et al. Effects of decocting Bupleurum at different times on the content and pharmacodynamics of saikosaponin in Wuchaihu Decoction [J]. Journal of Changchun University of Traditional Chinese Medicine 2018(4):641-644. 4. Ning Yanmei Yang Xiujuan Chen Hui Zhang Jinbao Yang Tao Ren Yuan. Determination and comparison of total saponins in Bupleurum products processed by different proportions of turtle blood [J]. Journal of Chinese Veterinary Medicine 2019 38(05):9-13. 5. Pang Xue, Liao Nian, Zhou Yiqun, et al. Effects of Different Processing Methods on Saikosaponin Content in Bupleurum chinense [J]. Shi Zhen Chinese Medicine 2016(12):2906-2908. 6. Liao Nian, Pang Xue, Zhou Yiqun, et al. Optimization of Orthogonal Test Method for Bran Simmering Process of Bupleurum chinense [J]. Shi Zhen Guo Yi Guo Yao 2017(05):96-98. 7. Li Ying, Jiao Qian, Zhang Tiantian, et al. Study on Ecological Suitability Zoning of Bupleurum chinense in Hebei Province Based on Topographic Factors [J]. Chinese Journal of Traditional Chinese Medicine, 2017, 042(022):4402-4407. 8. Cao Xue, Cai Guangzhi, Zhao Ling, et al. Grade Evaluation of Beicaihu Decoction Pieces Based on Compound Mass Constant [J]. Chinese Journal of Experimental Prescription, 2018(18). 9. Liao Nian, Pang Xue, Zhou Yiqun, et al. Optimization of Beicaihu Bran Stiffing Process by Orthogonal Test [J]. Chinese Pharmacist, 2017, 020(004):738-740. 10. Zhao Xintong, Xin Guo, Xin Yu, et al. Effect of decoction time on the contents of saikosaponin A and saikosaponin D in Bupleurum [J]. Ginseng Research, 2017. 11. Yang Mengling, You Pengtao, He Lishan, etc. Analysis of Pharmacokinetics of 8 Active Components in Plasma of Gastric Ulcer Model Rats after Oral Administration of Modified Xiaochaihu Granules Based on UPLC-MS/MS [J]. Chinese Journal of Traditional Chinese Medicine, 2018, 43(18). 12. Min, Wang Mengmeng, Wu Yu, Chen Wenwen, Wang Zhitong, Zhang Leiyang, Jiang Jian. Pharmacokinetics of Six Components of Buzhong Yiqi Decoction in Rats [J]. Liaoning Journal of Traditional Chinese Medicine, 2020,47(11):159-163. 13. Tian D-D, Wang W, Wang H-N, Sze SCW, Zhang Z-J. Pharmacokinetic Evaluation of Clozapine in Concomitant Use of Radix Rehmanniae, Fructus Schisandrae, Radix Bupleuri, or Fructus Gardeniae in Rats. Molecules. 2016; 21(6):696. https://doi.org/10.3390/molecules 14. Wang, Wei, dan-Dan Tian, and Zhang-Jin Zhang. "In Vitro Effects of Concomitant Use of Herbal Preparations on Cytochrome P450s Involved in Clozapine Metabolism." Molecules 21.5 (2016): 597.https://doi.org/10.3390/molecules21050597 15. [IF = 4.411] Wei Wang et al."In Vitro Effects of Concomitant Use of Herbal Preparations on Cytochrome P450s Involved in Clozapine Metabolism." Molecules 2016 May;21(5): 597 16. [IF = 4.411] Dan-Dan Tian et al."Pharmacokinetic Evaluation of Clozapine in Concomitant Use of Radix Rehmanniae, Fructus Schisandrae, Radix Bupleuri, or Fructus Gardeniae in Rats." Molecules. 2016 Jun;21(6):696 17. [IF = 4.396] Xiaoman Chen et al."Synergetic and Antagonistic Molecular Effects Mediated by the Feedback Loop of p53 and JNK between Saikosaponin D and SP600125 on Lung Cancer A549 Cells." Mol Pharmaceut. 2018;15(11):4974-4984 18. [IF = 3.396] Shi Weiwei et al."Saikosaponin-d inhibits proliferation by up-regulating autophagy via the CaMKKβ-AMPK-mTOR pathway in ADPKD cells." Mol Cell Biochem. 2018 Dec;449(1):219-226 19. [IF = 3.205] Min He et al."Simultaneous determination of multiple bioactive components of Bu-zhong-yi-qi-tang in rat tissues by LC-MS/MS: application to a tissue distribution study." J Chromatogr B. 2017 Feb;1044-1045:177 20. [IF = 5.81] Cui Lihua et al."Chaihu Guizhi Ganjiang Decoction Ameliorates Pancreatic Fibrosis via JNK/mTOR Signaling Pathway." Front Pharmacol. 2021 Jun;0:1369 21. [IF = 4.36] Xiaojing Zhang et al."A new discovery: total Bupleurum saponin extracts can inhibit the proliferation and inuce apoptosis of colon cancer cells by regulating the PI3K/Akt/mTOR pathway." J Ethnopharmacol. 2022 Jan;283:114742 22. [IF = 3.375] Tian Gao et al."Use of Saikosaponin D and JNK inhibitor SP600125, alone or in combination, inhibits malignant properties of human osteosarcoma U2 cells." Am J Transl Res. 2019; 11(4): 2070-2080 23. [IF = 3.337] Mengru Lai et al."Saikosaponin D Inhibits Proliferation and Promotes Apoptosis Through Activation of MKK4-JNK Signaling Pathway in Pancreatic Cancer Cells." Oncotargets Ther. 2020; 13: 9465-9479 24. [IF = 3.205] Jie Tang et al."Metabolite profiling of Shuganzhi tablets in rats and pharmacokinetics study of four bioactive compounds with liquid chromatography combined with electrospray ionization tandem mass spectrometry." J Chromatogr B. 2021 Aug;1179:122827 25. [IF = 3] Qu Lala et al."Phenotypic assessment and screening of ETA/ETB receptors with label-free dynamic mass redistribution say." N-S Arch Pharmacol. 2020 Jun;393(6):937-950 26. [IF = 2.45] Li Shengyun et al." Establishment and Application of a Method for the Determination of Ganoderic Acid A."J Food Quality. 2020;2020:6621853 27. [IF=3.911] Du Jikun et al."Saikosaponin-D Mitigates Oxidation in SH-SY5Y Cells Stimulated by Glutamate Through Activation of Nrf2 Pathway: Involvement of PI3K."Neurotox Res. 2022 Jan;:1-11 |
(3beta,16alpha)-16,23-Dihydroxy-13,28-epoxyolean-11-en-3-yl 6-deoxy-3-O-beta-D-glucopyranosyl-beta-D-galactopyranoside - Reference Information
| overview | saikosaponin d(Saikosaponind,SSd) is BupleurumChineseDC from Bupleurum, a plant of Umbelliferae. And Bupleurum angustifolia BupleurumscozonerifoliumWilld. A class of saponin monomer components mentioned in dried roots are one of the main chemical indicators and bioactive components of Bupleurum. Now studies have shown that saikosaponin d has the strongest pharmacological activity, with antipyretic, sedative, anti-inflammatory, antibacterial, hepatoprotective, anti-nephritis, immune regulation and other pharmacological effects. Although Bupleurum is listed as the top grade in the "Benjing", it has not been listed as a toxic product in the past dynasties, but with the increasing number of reports of adverse reactions in clinical application in recent years, especially the poisoning of Bupleurum in Japan is the most serious. |
| pharmacokinetics | saikosaponin d belongs to epoxy ether type pentacyclic triterpenoid oleanane derivative, its molecular formula is C42H68013, molecular weight is 780.96. Some studies have shown that after intraperitoneal injection of SSd in mice, it is distributed in blood and important tissues and organs, and the blood concentration reaches the peak after 2 hours. And there is a certain selectivity in the distribution of heart, brain, spleen and other organs, but the stability is poor, mostly in other forms. |
| target | TargetValue SERCA () |
| Target | Value |
| chemical properties | light yellow crystal, soluble in water, dilute alcohol, insoluble in benzene, ether, chloroform, derived from the above-ground part of Bupleurum. |
| use | saikosaponin d has sedative, antiviral, anti-inflammatory, immune regulation, liver and kidney protection and anti-tumor effects. used for content determination/identification/pharmacological experiment, etc. Pharmacological effects: cytotoxic activity, enhanced immune response, antibacterial effect, liver protection effect, antiviral and anti-inflammatory effects. |
Last Update：2024-04-09 20:52:54
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