489-32-7 Usage
Uses
Used in Pharmaceutical Applications:
Icariin is used as a hepatoprotective agent, demonstrating its potential in protecting the liver from damage and supporting overall liver health.
Used in Wound Healing Applications:
Icariin is used as a component in the preparation of topical treatments to determine its effects on the improvement of cutaneous wound healing in rats, showcasing its potential in accelerating the healing process and promoting tissue regeneration.
Used in Pain Management Applications:
Icariin has been utilized to test its analgesic effects on lower back pain (LBP) in rats, indicating its potential as a natural pain reliever for various types of pain, including musculoskeletal disorders.
Used in Osteoporosis Treatment:
Icariin is used as a potential treatment in osteoporosis conditions in rats, highlighting its role in strengthening bones and preventing bone loss associated with the disease.
Used in Insulin Resistance Studies:
Icariin has been used to study its effects on palmitate (PA)-induced insulin resistance in skeletal muscle C2C12 myotubes, suggesting its potential in managing and treating insulin resistance and related metabolic disorders.
Used in Neuroprotection Applications:
Icariin serves as a neuroprotective agent to study its effects on amyloid-β (Aβ)-induced neuronal insulin resistance in human neuroblastoma SK-N-MC cells, indicating its potential in protecting neurons and improving cognitive function in neurodegenerative diseases.
Used in Hair Growth Promotion:
Icariin has been used as a test material to investigate its in vitro effect in promoting mouse hair follicle growth, assessed by the vibrissae hair follicle (VHF) organ-culture model, suggesting its potential in developing treatments for hair loss and promoting hair growth.
References
[1] K. M. Chen, B. F. Ge, H. P. Ma, X. Y. Liu, M. H. Bai, Y, Wang (2005) Icariin, a flavonoid from the herb Epimedium enhances the osteogenic differentiation of rat primary bone marrow stromal cells, 60, 939-942
[2] Patent CN 1199647C “Application of icariin in preparation of medicine for preventing and treating sexual dysfunction”
[3] Patent CN 104739851 A “New application of icariin, or icariin derivatives or icariin salt”
Biological Activity
icariin exhibits inhibitory effects on cgmp-specific phosphodiesterase pde5 and camp-specific phosphodiesterase pde4 activities. phosphodiesterase (pde) is a crucial regulator of camp/pka signaling. pdes are encoded by 21 genes which can be sdivided into 11 families according to the substrate specificities and subcellular localization. pdes are widely expressed in neurons. pde5 has been implicated in regulating some physiological processes such as smooth muscle relaxation and neuronal survival. pde4 has been associated with the darpp-32 signaling pathway and dopaminergic neurotransmission [1].
Biochem/physiol Actions
Icariin is a potent neuroprotective agent in neurodegenerative disorders and other disorders affecting the nervous system. It elicits anti-aging properties in unfertilized oocytes against age-related damage. Icariin exerts anti-inflammatory and antifibrotic properties aiding protection in chronic kidney disease (CKD)-associated renal fibrosis in mouse model. It also serves as an excellent antidiabetic and anti-atherosclerotic agent. Icariin is an excellent anti-cancer agent.
in vitro
icariin inhibited the activity of pde5 and pde4 in a dose- andconcentration-dependent manner. the ic50of icariin on pde5 was 0.43 μm and the ic50 on pde4 was 73.50 μm. icariin showed a selective inhibitory effect on cgmp-specific pde5 compared to camp-specific pde4 [2].icariincould also enhance the osteogenic differentiation of rat primary bone marrow stromal cells [3].
in vivo
in castrated rats, a 4-week oral administration of icariinat 1 mg/kg/day and 5 mg/kg/day improved the erectile function and increased nnos and inos expression [4].icariin also showed its effect on stimulating angiogenesis in human endothelial cells [5].
references
nishi a, kuroiwa m, miller d b, et al. distinct roles of pde4 and pde10a in the regulation of camp/pka signaling in the striatum[j]. the journal of neuroscience, 2008, 28(42): 10460-10471.xin z c, kim e k, lin c s, et al. effects of icariin on cgmp-specific pde5 and camp-specific pde4 activities[j]. asian journal of andrology, 2003, 5(1): 15-18.chen k m, ge b f, ma h p, et al. icariin, a flavonoid from the herb epimedium enhances the osteogenic differentiation of rat primary bone marrow stromal cells[j]. die pharmazie-an international journal of pharmaceutical sciences, 2005, 60(12): 939-942.liu w j, xin z c, xin h, et al. effects of icariin on erectile function and expression of nitric oxide synthase isoforms in castrated rats[j]. asian journal of andrology, 2005, 7(4): 381-388.chung b h, kim j d, kim c k, et al. icariin stimulates angiogenesis by activating the mek/erk-and pi3k/akt/enos-dependent signal pathways in human endothelial cells[j]. biochemical and biophysical research communications, 2008, 376(2): 404-408.
Check Digit Verification of cas no
The CAS Registry Mumber 489-32-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 9 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 489-32:
(5*4)+(4*8)+(3*9)+(2*3)+(1*2)=87
87 % 10 = 7
So 489-32-7 is a valid CAS Registry Number.
InChI:InChI=1/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1
489-32-7Relevant articles and documents
Novel isopentenyl flavonoid compound and preparation method and application thereof
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Paragraph 0037-0040, (2020/11/10)
The invention discloses a novel isopentenyl flavonoid compound which is prepared by the following steps: (1) taking herba epimedii, crushing or not crushing, extracting with a solvent for 1-3 times, extracting for 0.2-3 hours each time, combining extracting solutions obtained by two times, and concentrating the extracting solutions under reduced pressure to obtain extract, and (2) adding water into the extract to prepare a suspension, carrying out gradient elution separation on the suspension by using macroporous resin, carrying out gradient elution separation by using an ODS column, and finally purifying the isopentenyl flavonoid compound by using an efficient preparative liquid phase. The isopentenyl flavonoid compound can be converted into icariin under the conditions of heating, acid treatment, enzyme treatment, alkali treatment and the like. The method is simple and convenient to operate, and the prepared compound has high purity.
Ep7GT, a glycosyltransferase with sugar donor flexibility from: Epimedium pseudowushanense, catalyzes the 7- O -glycosylation of baohuoside
Feng, Keping,Chen, Ridao,Xie, Kebo,Chen, Dawei,Liu, Jimei,Du, Wenyu,Yang, Lin,Dai, Jungui
supporting information, p. 8106 - 8114 (2019/09/19)
Icariin (1a), a 7-O-glycosylated flavonoid glycoside, is recognized as the major pharmacologically active ingredient of Epimedium plants, which have been used in traditional Chinese medicine for thousands of years. However, no glycosyltransferase (GT) responsible for the 7-O-glycosylation of flavonoids has been identified from Epimedium plants to date. Herein, a GT, Ep7GT, was identified from E. pseudowushanense B. L. Guo, which can regiospecifically transfer a glucose moiety to baohuoside (1) at 7-OH to form icariin (1a). Ep7GT showed a rare broad donor substrate spectrum, including UDP-glucose, UDP-xylose, UDP-N-acetylglucosamine, UDP-rhamnose, UDP-galactose, UDP-glucuronic acid and TDP-glucose. Moreover, two new derivatives of icariin (1a), 7-O-β-d-[2-(acetylamino)-2-deoxy-glucopyranosyl]-baohuoside (1b) and 7-O-β-d-xylosyl-baohuoside (1c), were biosynthesized by using Ep7GT in vitro. Engineered Escherichia coli harbouring Ep7GT was constructed, and 10.1 μg mL-1 icariin (1a) was yielded by whole-cell biotransformation with baohuoside (1) as the substrate. The present work not only characterizes the GT responsible for the 7-O-glycosylation in the biosynthesis of icariin in Epimedium plants, but also indicates the significant potential of an enzymatic approach for the production of glycosylated baohuoside derivatives with different sugar moieties. What's more, these findings also provide a promising alternative for producing natural/unnatural bioactive flavonoid glycosides by metabolic engineering.
Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen - Cope rearrangement
Mei, Qinggang,Wang, Chun,Zhao, Zhigang,Yuan, Weicheng,Zhang, Guolin
, p. 1220 - 1225 (2015/08/18)
The hemisynthesis of the naturally occurring bioactive flavonoid glycoside icariin (1) has been accomplished in eleven steps with 7% overall yield from kaempferol. The 4?-OH methylation of kaempferol, the 8-prenylation of 3-O-methoxymethyl-4?-O-methyl-5- O-prenyl-7-O-benzylkaempferol (8) via para-Claisen-Cope rearrangement catalyzed by Eu(fod)3 in the presence of NaHCO3 , and the glycosylation of icaritin (3) are the key steps.
