(3β,12β)-12,20-Dihydroxydammar-24-en-3-yl-β-D-glucopyranoside
Ginsenoside Rh2
CAS: 78214-33-2
Molecular Formula: C36H62O8
(3β,12β)-12,20-Dihydroxydammar-24-en-3-yl-β-D-glucopyranoside - Names and Identifiers
| Name | Ginsenoside Rh2 |
| Synonyms | GINSENOSIDE RH2 Ginsenoside Rh2 R-form-Ginsenoside Rh2 Ginsenoside Rh2, 20(S)- dihydroxydammar-24-en-3-yl β-D-Glucopyranoside, (3β,12β)-12,20- (3β,12β)-12,20-Dihydroxydammar-24-en-3-yl-β-D-glucopyranoside b-D-Glucopyranoside, (3b,12b)-12,20-dihydroxydaMMar-24-en-3-yl (3beta,12beta)-12,20-dihydroxydammar-24-en-3-yl beta-d-glucopyranoside (3beta,12beta)-12,20-Dihydroxydammar-24-en-3-yl beta-D-glucopyranoside |
| CAS | 78214-33-2 |
| InChI | InChI=1/C36H62O8/c1-20(2)10-9-14-36(8,42)21-11-16-35(7)27(21)22(38)18-25-33(5)15-13-26(32(3,4)24(33)12-17-34(25,35)6)44-31-30(41)29(40)28(39)23(19-37)43-31/h10,21-31,37-42H,9,11-19H2,1-8H3/t21-,22+,23+,24-,25+,26-,27-,28+,29-,30+,31-,33-,34+,35+,36-/m0/s1 |
| InChIKey | CKUVNOCSBYYHIS-IRFFNABBSA-N |
(3β,12β)-12,20-Dihydroxydammar-24-en-3-yl-β-D-glucopyranoside - Physico-chemical Properties
| Molecular Formula | C36H62O8 |
| Molar Mass | 622.88 |
| Density | 1.19±0.1 g/cm3(Predicted) |
| Melting Point | 139-144 °C |
| Boling Point | 726.4±60.0 °C(Predicted) |
| Specific Rotation(α) | +23°（c0.65，methanol） |
| Flash Point | 393.1°C |
| Solubility | DMSO : ≥ 100 mg/mL (160.55 mM) |
| Vapor Presure | 2.31E-24mmHg at 25°C |
| Appearance | Colorless needle crystal |
| pKa | 12.91±0.70(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.571 |
| MDL | MFCD00800712 |
| Physical and Chemical Properties | White powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from ginseng. |
| In vitro study | Ginsenoside Rh2 induces the activation of two initiator caspases, caspase-8 and caspase-9 in human cancer cells. Ginsenoside Rh2 induces cancer cell apoptosis in a multi-path manner and is therefore a promising candidate for anti-tumor drug development. Ginsenoside Rh2 triggers p53-dependent Fas expression and consequent activation of caspase-8 and p53-independent caspase-9-mediated intrinsic pathway to cause cancer cell death.The cytotoxic activity of Ginsenoside Rh2 in the human tumor cell lines HeLa, SK-HEP-1, SW480, and PC-3 is assessed by MTT. The cell viability of HeLa cells is remarkably inhibited by Ginsenoside Rh2, with an IC 50 value of 2.52 μg/mL, whereas SK-HEP-1 and SW480 cells are less sensitive to Ginsenoside Rh2, with IC 50 values of 3.15 μg/mL and 4.06 μg/mL, respectively. PC-3 cells are the least vulnerable to Ginsenoside Rh2, with an IC 50 value of 7.85 μg/mL, 3-fold higher than HeLa cells. |
| In vivo study | A total of 15 days following B16-F10 cell injection, tumor sizes from the 3 tumor bearing groups are measured. The tumor sizes in the G-L group and G-H group (G-L and G-H refer to a low or high dose of ginsenoside Rh2 injection) are reduced compared with the tumor group (P<0.05). The survival analysis reveals that the Ginsenoside Rh2 treated groups survive longer than the untreated tumor group and the effect is dose-dependent (P<0.05). |
(3β,12β)-12,20-Dihydroxydammar-24-en-3-yl-β-D-glucopyranoside - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | LZ5776539 |
| HS Code | 29389090 |
(3β,12β)-12,20-Dihydroxydammar-24-en-3-yl-β-D-glucopyranoside - Reference
| Reference Show more | 1. Chen Yuquan, Liu Yuting, Qiu Jie, et al. Comparison of different colorimetric methods for determination of total triterpenoid saponins from plants [J]. Heilongjiang Agricultural Sciences 2018 000(003):108-112. 2. Ma Xiaowei in Mongolia, Jin, Xinghua, etc. Determination of saponin content in crude drug of ginsenoside H dropping pills and screening of effective components by cell membrane chromatography [J]. Chinese herbal medicine 2018 v.49;No.622(11):62-67. 3. Nieliu, penhanming. Effect and mechanism of Ginsenoside Rh2 on inducing apoptosis of human T-cell acute lymphoblastic leukemia Jurkat cells [J]. Chinese Journal of Experimental Hematology, 2019, 27(04):1111-1117. 4. Zhang Cai Hua Li Li Li Hua Jun et al. Effects of Ginsenoside Rh2 on the expression and growth of lung cancer A549 cells miR-16 and Bcl-2 [J]. Chinese Journal of microecology, 2015, 27(009):1027-1030. 5. Cui Yong, Li Shiming, Jin Yan, et al. Ginsenoside Rh2 inhibits airway remodeling in asthmatic mice via VEGF/MMP-9 signaling pathway [J]. Chinese Journal of Traditional Chinese Medicine 2017(08):14-17. 6. Zhang Lei, Hao Yiwei, Jing Yunrong, etc. Effect of perilla leaf on hyperuricemia model mice. 7. Miao Rui, Wu Dongxue, Wang Qiuying, etc. Rapid separation of ginsenosides based on multi-walled carbon nanotubes [J]. Journal of Chemistry of universities, 2018. 8. Li Xueqing, Li Li, Liu Xuefeng, etc. Study on the metabolism of Panax notoginseng saponins in human intestinal flora [J]. Pharmaceutical Biotechnology, 2017(03):34-39. 9. Xu, Xiang, et al. "Ginsenoside Rh2 attenuates microglial activation against toxoplasmic encephalitis via TLR4/NF-κB signaling pathway." Journal of Ginseng Research 44.5 (2020): 704-716.https://doi.org/10.1016/j.jgr.2019.06.002 10. Wang, Zhihua, et al. "Comprehensive TCM molecular networking based on MS/MS in silico spectra with integration of virtual screening and affinity MS screening for discovering functional ligands from natural herbs." Analytical and bioanalytical chemistry 411 11. Zhang, Hong-Mei, et al. "Holistic quality evaluation of commercial white and red ginseng using a UPLC-QTOF-MS/MS-based metabolomics approach ." Journal of pharmaceutical and biomedical analysis 62 (2012): 258-273.https://doi.org/10.1016/j.jpba.2012.01.010 12. Hong Zhang, Jia-Ming Jiang, Dan Zheng, Ming Yuan, Zhi-Ying Wang, Hong-Mei Zhang, Chang-Wu Zheng, Lian-Bo Xiao, Hong-Xi Xu,A multidimensional analytical approach based on time-decoupled online comprehensive two-dimensional liquid chromatography coupled wit 13. Hong Zhang, Jia-Ming Jiang, Dan Zheng Ming Yuan, Zhi-Ying Wang, Hong-Mei Zhang, Chang-Wu Zheng, Lian-Bo Xiao, Hong-Xi Xu,A multidimensional analytical approach based on time-decoupled online comprehensive two-dimensional liquid chromatography coupled wit 14. Hong Zhang, Jia-Ming Jiang, Dan Zheng, Ming Yuan, Zhi-Ying Wang, Hong-Mei Zhang, Chang-Wu Zheng, Lian-Bo Xiao Hong-Xi Xu,A multidimensional analytical approach based on time-decoupled online comprehensive two-dimensional liquid chromatography coupled wit 15. Joo, Kyung-Mi, et al. "Pharmacokinetic study of ginsenoside Re with pure ginsenoside Re and ginseng berry extracts in mouse using ultra performance liquid chromatography/mass spectrometric method." Journal of pharmaceutical and biomedical analysis 51.1 (20 16. [IF=3.935] Hong-Mei Zhang et al."Holistic quality evaluation of commercial white and red ginseng using a UPLC-QTOF-MS/MS-based metabolomics approach."J Pharmaceut Biomed. 2012 Mar;62:258 17. [IF=6.558] Qingqing Song et al."Binary code, a flexible tool for diagnostic metabolite sequencing of medicinal plants."Anal Chim Acta. 2019 Dec;1088:89 18. [IF=6.06] Xiang Xu et al."Ginsenoside Rh2 reduces depression in offspring of mice with maternal toxoplasma infection during pregnancy by inhibiting microglial activation via the HMGB1/TLR4/NF-κB signaling pathway."J Ginseng Res. 2021 Apr;: 19. [IF=6.06] Zhenzhuo Li et al."Ginsenosides repair UVB-induced skin barrier damage in BALB/c hairless mice and HaCaT keratinocytes."J Ginseng Res. 2021 May;: 20. [IF=5.396] Hui Wang et al."Ginsenoside extract from ginseng extends lifespan and health span in Caenorhabditis elegans."Food Funct. 2021 Aug;12(15):6793-6808 21. [IF=4.411] Jianbo Chen et al."Neuroprotective Effects of Red Ginseng Saponins in Scopolamine-Treated Rats and Activity Screening Based on Pharmacokinetics."Molecules. 2019 Jan;24(11):2136 22. [IF=4.142] Wang Chenxi et al."Rapid discovery of potential ADR compounds from injection of total saponins from Panax notoginseng using data-independent acquisition untargeted metabolomics."Analytical And Bioanalytical Chemistry. 2021 Oct 26 23. [IF=4.029] Xiang Xu et al."Ginsenoside Rh2 attenuates microglial activation against toxoplasmic encephalitis via TLR4/NF-κB signaling pathway."J Ginseng Res. 2020 Sep;44:704 24. [IF=3.935] Ruimei Lin et al."Global identification and determination of the major constituents in Kai-Xin-San by ultra-performance liquid chromatography-quadrupole-Orbitrap mass spectrometry and gas chromatography-mass spectrometry."J Pharmaceut Biomed. 2021 Nov;206 25. [IF=2.547] Zhongyi Cong et al."Ginsenoside Rh3 Inhibits Proliferation and Induces Apoptosis of Colorectal Cancer Cells."Pharmacology. 2020;105(5-6):329-338 26. [IF=6.543] Liang Yuan et al."Identification of 20(S)-Ginsenoside Rh2 as a Potential EGFR Tyrosine Kinase Inhibitor."Oxid Med Cell Longev. 2022;2022:6119737 |
(3β,12β)-12,20-Dihydroxydammar-24-en-3-yl-β-D-glucopyranoside - Reference Information
| Plant Source: | ginseng |
| Overview | Ginsenoside Rh2 is an anticancer active plant ingredient extracted from ginseng, at present has been recognized by more and more cancer patients, improve the quality of life of patients, prolong life has a very good effect, so enjoy the "Protection of Life" reputation. Specific performance for the adjuvant treatment of cancer, chemical name of protopanaxadiol -3-oxygen-B-D-glucopyranoside, namely ginsenoside Rh2. |
| biological activity | Ginsenoside Rh2 was isolated from ginsen root. Ginsenoside Rh2 induced caspase-8 and caspase-9 activation. Ginsenoside Rh2 induces apoptosis of cancer cells in a multi-pathway manner. |
| Use | for content determination/identification/pharmacological experiments. Pharmacological Efficacy: 1. At 1.0mg/mL, for ccl4-induced liver poisoning in rats have a significant protective effect. 2. Inhibit the proliferation of melanoma B16 nuclear human ovarian cancer cells. 3. Cytotoxic activity against MT-4 cells. (20s)-Ginsenoside Rh2 is a triterpene saponin isolated from Panax ginseng, which has high anti-inflammatory and anti-cancer activities. |
Last Update：2024-04-09 15:16:52
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