Name | baohuoside I |
Synonyms | Icariin II Icarisid II Baohuoside-1 BAOHUOSIDE I baohuoside I Baohuoside I ICARISIDE II ANHYDROICARITIN Baohuoside I(Icariside II) 3,5,7-Trihydroxy-4'-methoxyl-8-prenylflavone-3-O-rhamnopyranoside 5,7-Dihydroxy-4'-methoxy-8-prenyl-3-(α-L-rhamnopyranosyloxy)flavone 3-(α-L-Rhamnopyranosyloxy)-4'-methoxy-5,7-dihydroxy-8-prenylflavone 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)- |
CAS | 113558-15-9 |
InChI | InChI=1/C27H30O10/c1-12(2)5-10-16-17(28)11-18(29)19-21(31)26(37-27-23(33)22(32)20(30)13(3)35-27)24(36-25(16)19)14-6-8-15(34-4)9-7-14/h5-9,11,13,20,22-23,27-30,32-33H,10H2,1-4H3/t13-,20-,22+,23+,27-/m0/s1 |
Molecular Formula | C27 H30 O10 |
Molar Mass | 514.52 |
Density | 1.46 |
Melting Point | 202-203 °C |
Boling Point | 759.4±60.0 °C(Predicted) |
Specific Rotation(α) | (c, 0.09 in MeOH)-121 |
Flash Point | 253.8°C |
Solubility | DMSO : ≥ 32 mg/mL (62.19 mM) |
Vapor Presure | 3.07E-24mmHg at 25°C |
Appearance | Yellow needle crystal |
Color | Light Yellow |
pKa | 6.29±0.40(Predicted) |
Storage Condition | Inert atmosphere,Room Temperature |
Refractive Index | 1.666 |
MDL | MFCD15071140 |
Physical and Chemical Properties | Yellow needle-like crystals, soluble in methanol, derived from the whole herb of epimedium. |
In vitro study | Baohuoside I is an inhibitor of CXCR4, and downregulates CXCR4 expression at 12-25 μM. Baohuoside I (0-25 μM) suppresses NF-κB activation in a dose-dependent manner, suppresses CXCL12 induced the invasion of cervical cancer cells. Baohuoside I also inhibits invasion of breast cancer cells. Baohuoside I inhibits A549 cell viability, with IC 50 s of 25.1 μM at 24 h, 11.5 μM and 9.6 μM at 48 h and 72 h, respectively. Baohuoside I ((25 μM) suppresses the caspase cascade in A549 cells, elevates ROS levels and activates JNK and p38 MAPK signaling cascade. Baohuoside I (3.125, 6.25, 12.5, 25.0 and 50.0 µg/mL) significantly and dose-dependently blocks the growth of esophageal squamous cell carcinoma Eca109 cells, with an IC 50 of 4.8 µg/mL at 48 h. |
In vivo study | Baohuoside I (25 mg/kg) decreases β-catenin protein levels, cyclin D1 and survivin expression in nude mice. |
HS Code | 29329990 |
Reference Show more | 1. Yang Yishun, Zhang Tong, Ding Yue et al. Preparation and HPLC Determination of Three Secondary Icariin Products [J]. Chinese Patent Medicine 2020 042(003):779-782. 2. Li Ruiyun, Liu Congyan, Xu Ting et al. Preparation and Characterization of Cross-linked Nano-SiO_2 Immobilized Snail Enzyme and Study on Transformation of Icariin [J]. Chinese Herbal Medicine 2019 v.50;No.655(20):57-63. 3. Gao Xia, chen Yan, Wang Ying, et al. Multivariate Investigation on Bionic Enzymatic Hydrolysis of Icariin [J]. Journal of Pharmacy, 2013(11):1716-1721. 4. Liu Yuping, Ding Xuefang, Huang Mengmeng, et al. Study on Intestinal Absorption and Metabolism of Icariin in Different Osteoporosis Rat Models [J]. Chinese Journal of Traditional Chinese Medicine, 2016(13):2532-2537. 5. Gu Huimin, Sun E, Li Jie, et al. Effect of processing excipient suet oil on formation and absorption of self-assembled micelles of baogouin I-cholate [J]. Chinese Journal of Traditional Chinese Medicine, 2019, v.44(23):133-140. 6. Yang Ru, Liu Congyan, Xu Ting, et al.. Adsorption Characteristics of Five Macroporous Adsorption Resins on Total Flavonoids of Epimedium [J]. Chinese Journal of Experimental Presentation 2020 v.26(06):121-128. 7. Wang Ying, Gao Xia, Chen Yan, et al.. Effect of Carbomer on Enzymatic Hydrolysis of Total Flavonoids of Epimedium [J]. Chinese Journal of Experimental Presentation 2014 20(009):1-5. 8. Liu Cong Yan Gao Xia Chen Yan et al. Feasibility Study on Improving Oral Bioavailability of Epimedium Total Flavonoids by Biomimetic Enzymatic Hydrolysis Enteric-coated Capsules [J]. chinese journal of pharmaceutical industry 2016(9):1158-1164. 9. Zhang Yan. Separation and Purification of Epimedium EF5 Flavonoids by Macroporous Adsorption Resin [J]. Northern Pharmacy, 2015, 000(011):11-13. 10. Liu congyan, Gao Xia, Huang mengmeng, et al. preparation and evaluation of epimedium total flavonoids biomimetic enzymatic enteric-coated capsules [J]. Chinese herbal medicine, 2016(20). 11. Liu congyan, Gao Xia, Chen Yan, et al. pharmacokinetic behavior of epimedium total flavonoids in osteoporotic rats [J]. Chinese patent medicine, 2017, 39(008):1595-1600. 12. Gao Xia, Liu Xuan, Chen Yan, et al. Biotransformation Process Analysis of Total Flavonoids of Epimedium [J]. Chinese Journal of Traditional Chinese Medicine, 2013, 38(23):4079. 13. Gao Xia, Chen Yan, Wang Ying, et al. Effect of Dextrin Wet Granulation on Enzymatic Hydrolysis of Total Flavonoids of Epimedium [J]. Chinese Patent Medicine, 2014, 36(007):1392-1397. 14. Peng Jing, Ma Yihua, Chen Yan, et al. Simultaneous Biotransformation of Four Flavonoid Glycosides in Epimedium by Immobilized Snail Enzyme [J]. Chinese Patent Medicine, 2016, 38(9):1984-1990. 15. Liu Congyan, Li Ruiyun, Ma Chengyao, Liu Yuping, Qu Ding, Li Xiaoqi, Chen Yan. Biotransformation of icariin by β-glucosidase immobilized on chitosan crosslinked mesoporous silica [J]. Chinese herbal medicine, 2021,52(03):685-691. 16. Xu Ting, Huang Mengmeng, Li Ruiyun, Yang Ru, Liu Lifang, Chen Yan. Study on Quality Evaluation of Different Parts of Multi-base Primary Epimedium [J]. Chinese herbal medicine, 2020,51(01):190-196. 17. Yang, Jing, et al. "Icariside II induces cell cycle arrest and differentiation via TLR8/MyD88/p38 pathway in acute myeloid leukemia cells." European journal of pharmacology 846 (2019): 12-22.https://doi.org/10.1016/j.ejphar. 2018.12.026 18. Liu, Congyan, et al. "Icariin combined with snailase shows improved intestinal hydrolysis and absorption in osteoporosis rats." Biomedicine & Pharmacotherapy 94 (2017): 1048-1056.https://doi.org/10.1016/j.biopha. 2017.07.163 19. [IF=6.529] Congyan Liu et al."Icariin combined with snailase shows improved intestinal hydrolysis and absorption in osteoporosis rats."Biomed Pharmacother. 2017 Oct;94:1048 20. [IF=3.263] Jing Yang et al."Icariside II induces cell cycle arrest and differentiation via TLR8/MyD88/p38 pathway in acute myeloid leukemia cells."Eur J Pharmacol. 2019 Mar;846:12 21. [IF=4.411] Zhenxian Qin et al."A Widely Metabolomic Analysis Revealed Metabolic Alterations of Epimedium Pubescens Leaves at Different Growth Stages."Molecules. 2020 Jan;25(1):137 22. [IF=4.36] Kun Shi et al."Epimedii Folium and Curculiginis Rhizoma ameliorate lipopolysaccharides-induced cognitive impairment by regulating the TREM2 signaling pathway."J Ethnopharmacol. 2022 Feb;284:114766 23. [IF=3.757] Congyan Liu et al."Enhanced hydrolysis and antitumor efficacy of Epimedium flavonoids mediated by immobilized snailase on silica."Process Biochem. 2019 Nov;86:80 24. [IF=3.645] Hongmin Zhang et al."Simultaneous determination of five isoflavones in rat plasma by LC-MS/MS: Comparative pharmacokinetic characteristics of Puerariae lobatae radix in normal and type 2 diabetic rats."J Sep Sci. 2019 Aug;42(16):2592-2601 25. [IF=2.886] Fubiao Ni et al."Baohuoside I Inhibits the Proliferation of Pancreatic Cancer Cells via mTOR/S6K1-Caspases/Bcl2/Bax Apoptotic Signaling."Cancer Manag Res. 2019; 11: 10609-10621 26. [IF=2.886] Yangyang Guo et al."Baohuoside I via mTOR Apoptotic Signaling to Inhibit Glioma Cell Growth."Cancer Manag Res. 2020; 12: 11435-11444 27. [IF=1.902] Ting Zhang et al."The influence of essential oils from ZhaLi NuSi Prescription on the pharmacokinetics of its non-volatile components in normal rats."Biomedical Chromatography. 2021 Oct 21 |