cas 118525-40-9, Icaritin | Articles data

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Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen - Cope rearrangement
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.
Mei, Qinggang,Wang, Chun,Zhao, Zhigang,Yuan, Weicheng,Zhang, Guolin
p. 1220 - 1225
(2015)
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A novel anticancer agent, icaritin, induced cell growth inhibition, G1 arrest and mitochondrial transmembrane potential drop in human prostate carcinoma PC-3 cells
Icariin and icaritin with prenyl group have been demonstrated for their selective estrogen receptor modulating activities. We screened their effects on cell growth in human prostate carcinoma PC-3 cell line (estrogen receptor positive) in vitro. PC-3 cell line was used for the measurement of anti-carcinoma activities of 0-100 μmol/l icaritin and 30 μmol/l icariin. 1 μmol/l 17-β estradiol (E2) served as the estrogen positive control, and 1 μmol/l ICI 182,780 [7 α-[9 (4,4,5,5,5-pentafluoropentyl) sulfinyl] nonyl]-estra-1,3,5(10)-triene-3,17h-diol]] served as the specific estrogen receptor antagonist. Primary cultured rat prostate basal cells used as cell growth selective control. The growth-inhibitory effects were analyzed using MTT assay, and fluorochrome staining, flow cytometry, and immunoblotting were employed to illustrate the possible mechanisms. When treated with icaritin for 24 to 72 h, cell growth was strongly inhibited (at 48 h IC50 was 10.74 ± 1.59 μmol/l, P 50 could be observed when co-incubated with ICI 182,780. Icaritin-induced growth inhibition was associated with G1 arrest (P 2-M arrest depending upon doses. Consistently with G1 arrest, icaritin increased protein expressions of pRb, p27Kip1 and p16Ink4a, while showed decrease in phosphorylated pRb, Cyclin D1 and CDK4. Comparatively, icariin has much lower effects on PC-3 cells and showed only weak G1 arrest, suggesting a possible structure-activity relationship. These findings suggested a novel anticancer efficacy of icaritin mediated selectively via induction of cell cycle arrest but not associated with estrogen receptors in PC-3 cells.
Huang, Xin,Zhu, Danyan,Lou, Yijia
p. 26 - 36
(2007)
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Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin
The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug
Fu, Xuewen,Lu, Xiaoxia,Wang, Chun,Wen, Yongju,Xiong, Wei,Zhang, Guolin,Zhang, Jichao
p. 1117 - 1124
(2022/02/16)

Phosphate ester derivative of herba epimedii as well as preparation method and application of phosphate ester derivative
The invention belongs to the technical field of medicines, and discloses a phosphate ester derivative of herba epimedii as well as a preparation method and application of the phosphate ester derivative. The chemical structural formula of the phosphate ester derivative of the herba epimedii is represented by the formula (1), wherein R1 is selected from groups defined in the specification, or R2 is selected from H or R1, and R3 is selected from H or a group defined in the specification. According to the phosphate ester derivative of the herba epimedii, the cytotoxicity of the partially modified derivative is remarkably enhanced compared with that of an unmodified derivative, and meanwhile the phosphate ester derivative of the herba epimedii has the anti-osteoporosis effect. The phosphate ester derivative of the herba epimedii can be applied to the field of preparation of drugs for prostate cancer cells, anti-osteoporosis health-care products, pharmaceutical excipients or drugs.
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Paragraph 0033-0038

(2021/06/26)

Convenient and efficient total synthesis method for icaritin and derivatives of icaritin
The invention belongs to the field of natural medicine synthesis and particularly relates to a convenient and efficient total synthesis method for icaritin and derivatives of icaritin. The specific technical scheme is as follows: 2'-hydroxyacetophenone and benzaldehyde are used as raw materials, firstly, isopentene groups are introduced in aromatic rings of raw materials under the catalysis of anorganic polyacid metal ion complex, a flavonol framework is constructed under mild and green conditions, and an isopentenyl flavone compound comprising the icaritin and derivatives of icaritin is further synthesized. The method effectively overcomes the limitation of poor substrate solubility and poor regioselectivity when flavone is constructed firstly and then isopentene groups are introduced, the problems of frequent introduction and removal of protecting groups in a conventional isopentenylation method are solved, and the synthesis route is greatly simplified; and meanwhile, the problems of complex products and more byproducts in an isopentene group rearrangement method are solved. The total synthesis method provided by the invention is mild in condition, convenient to operate, high intotal yield and suitable for mass production of the isopentenyl flavone compound.
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Paragraph 0063; 0084-0088

(2020/02/06)

ANALOGS OF THE NATURAL PRODUCT ICARIIN
Provided herein are analogs of the natural product icariin represented by Structural Formula (I) or a pharmaceutically acceptable salt thereof. The analogs can be used to modulate (e.g., inhibit, such as by competitive inhibition) PDE5 and thereby treat a wide range of PDE5- mediated diseases, including cardiovascular, gastrointestinal, pulmonary, musculoskeletal, neurological and reproductive diseases. Also provided herein are compositions and methods including compounds of Structural Formula (I).
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Paragraph 00168; 00192

(2020/03/02)

Preparation and medical application methods of icaritin derivative
The invention relates to preparation and medical application methods of an icaritin derivative. The preparation method comprises taking trihydroxyacetophenone, chloromethyl methyl ether and the like as initial raw materials to connect isopentene groups to an 8th carbon through vicinal rearrangement, then performing serial reaction of formation of a flavone framework, and lastly, performing dehydration to introduce propylene groups to synthesize the icaritin derivative. The preparation method of the icaritin derivative is low in the cost of the synthetic routes, simple in operation, high in recovery rate and applicable to industrial production. Pharmacological effect experiments prove that the icaritin derivative has the pharmacological effect of activating organism endogenous stem cells and achieves the rehabilitation function of repair traumatic pathological changes of blood vessels, nerves, endothelial cells and matrixes and can be applied to preparing drugs for repairing traumatic pathological changes of tissues, thereby having a good prospect in fields such as drugs for rehabilitation of pathological changes of erectile dysfunction.
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(2019/10/23)

Flavone derivative and preparation method and medical application of flavone derivative
The invention relates to a flavone derivative and a preparation method and medical application of the flavone derivative. The flavone derivative is prepared through a mode that anhydroicaritin is taken as a mother nucleus, and group addition and reduction are conducted. It is proved through a pharmacological experiment that the flavone derivative has the pharmacological effect of activating endogenous stem cells in the body, achieves the effects of repairing injury-type pathological changes of blood vessel cells, nerve cells, endothelial cells and the matrix and recovering functions, can be used for preparing medicines for repairing the tissue-injury pathological changes and has a good prospect in preparing medicines for conducting rehabilitation treatment on erectile dysfunction pathological changes.
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Paragraph 0084; 0093

(2019/09/05)

Exploration of icariin analog structure space reveals key features driving potent inhibition of human phosphodiesterase-5
The natural product icariin inhibits human phosphodiesterase-5 (PDE5) and represents a unique pharmacophore for treating erectile dysfunction, pulmonary hypertension, and other diseases. In this study, we explore the available icariin-derived chemical scaffolds through medicinal chemistry to develop novel icariin PDE5 inhibitors with improved potency and specificity. We synthesized six novel semi-synthetic icariin analogs as well as three naturally occurring icariin analogs, and characterized the structure-activity relationship in the context of human PDE5 inhibition using in vitro enzyme inhibition and kinetics assays and molecular modeling. Mammalian-cell-based assays and in vitro enzyme inhibition assays against human PDE6C further helped to identify the most potent and selective icariin analogs. Our results reveal the synergistic contribution of functional groups at the C3 and C7 positions of the icariin backbone towards PDE5 inhibition. Whereas a hydrophobic and flexible alkanol group at the C7 position is sufficient to enhance icariin analog potency, combining this group with a hydrophilic sugar group at the C3 position leads to further enhancement of potency and promotes specificity towards PDE5 versus PDE6C. In particular, compounds 3 and 7 exhibit Ki values of 0.036 ± 0.005 μM and 0.036 ± 0.007 μM towards PDE5 respectively, which are approaching those of commercial PDE5 inhibitors, and can effectively reduce GMP levels in cultured human BJ-hTERT cells. This study identifies novel icariin analogs as potent and selective PDE5 inhibitors poised to become lead compounds for further pharmaceutical development.
Chau, Yasmin,Li, Fu-Shuang,Levsh, Olesya,Weng, Jing-Ke
(2019/09/30)

Icarisid I type compound, derivatives, pharmaceutical composition and application thereof
The invention provides an icarisid I type compound and derivatives, or a stereisomer, geometrical isomer, tautomer, nitrogen oxide, hydrate, solvate, metabolite, pharmaceutically-acceptable salt or prodrug of the compound of formula I (shown in the specification). The synthetic materials of the icarisid I type compound and derivatives are selected from quercetin, apigenin, kaempferol, scutellarein, wild scutellarein, chrysin, daidzein, genistein, isorhamnetin, myricetin, luteolin, fisetin or icaritin. By methods of chemical synthesis and bioengineering, the icarisid I type compound and derivatives with better biological effect and higher economic benefit can be synthesized by flavone compounds (such as the apigenin and the quercetin and the like) with higher existence in nature.
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(2019/03/06)

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis
Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.
Zheng, Yuanyuan,Pu, Wenchen,Li, Jiao,Shen, Xianyan,Zhou, Qiang,Fan, Xin,Yang, Sheng-Yong,Yu, Yamei,Chen, Qiang,Wang, Chun,Wu, Xin,Peng, Yong
p. 130 - 134
(2018/11/30)

Icaritin synthesis method
The invention provides an icaritin synthesis method. The method includes that kaempferol-4-oxymethyl ether serves as a raw material for preparing icaritin. The icaritin synthesis method has advantages that by adoption of a lanthanide metal lewis acid catalyst in a rearrangement reaction process, icaritin obtained according to an existing chemical synthesis method is low in impurity content and is up to 98% in purity, and the yield can exceed 30%.
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Paragraph 0116; 0117; 0118; 0120; 0121; 0122; 0145-0150

(2017/10/07)

Herba Epimedii glycoside compound and use thereof
The invention relates to an icariin compound and an application of the icariin compound in preparing medicines for preventing and treating fracture and osteoporosis. Particularly, the invention relates to the compound shown in a general formula (I) in the specification, a stereisomer, a stereomer, a tautomer, oxynitrides, hydrates, solvates, metabolites, and pharmaceutically acceptable salts or prodrugs thereof, wherein the variables are defined in the specification. The invention further relates to use of the compound, the stereisomer, the stereomer, the tautomer, oxynitrides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or salt of prodrugs thereof as medicines, particularly use in preparing medicines for preventing and treating fracture and osteoporosis.
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(2017/08/24)

A kind of icariin derivatives and their methods of use and use (by machine translation)
The invention provides an icariin derivative as shown in formula (I) or a stereisomer, a tautomer, nitrogen oxide, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, and a pharmaceutical composition. The invention further relates to a method for preparing the compounds and the pharmaceutical composition, and a use thereof in prevention or treatment of sexual dysfunction, cardiac-cerebral vascular diseases, osteoporosis or cancers. The formula is described in the description.
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Paragraph 0156-0157; 0161-0162

(2016/12/07)

Heiba boschnaloside compound and use thereof
The invention relates to a kind of icariin compounds shown in a formula (I) or stereoisomers, geometrical isomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs of the compounds shown in the formula (I). The invention also discloses a drug composition containing the compounds, a preparation method of the compounds or the drug composition and an application of the compounds or the drug composition to preparation of drugs for preventing and treating fractures and osteoporosis.
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Paragraph 0118; 0122-0125

(2020/02/08)

Total synthesis of icaritin via microwave-assistance Claisen rearrangement
The novel total synthesis of icaritin (1), naturally occurring with important bioactive 8-prenylflavonoid, was performed via a reaction sequence of 8 steps including Baker-Venkataraman reaction, chemoselective benzyl or methoxymethyl protection, dimethyldioxirane (DMDO) oxidation, O-prenylation, Claisen rearrangement and deprotection, starting from 2,4,6-trihydroxyacetophenone and 4-hydroxybenzoic acid in overall yields of 23%. The key step was Claisen rearrangement under microwave irradiation. MS, 1H and 13C NMR techniques have been used to confirm the structures of all synthetic compounds.
Nguyen, Van-Son,Shi, Ling,Li, Yue,Wang, Qiu-An
p. 677 - 681
(2015/04/14)

Synthesis and antimultidrug resistance evaluation of icariin and its derivatives
A series of icariin derivatives were synthesized. Their multidrug resistance (MDR) reversal activities were evaluated by MTT assay and the results indicated that the derivatives were the potent modulators of MDR. It was showed that the derivatives signifi
Liu, Dong-Fang,Li, Yan-Ping,Ou, Tian-Miao,Huang, Shi-Liang,Gu, Lian-Quan,Huang, Min,Huang, Zhi-Shu
supporting information; experimental part
p. 4237 - 4240
(2010/04/26)

Potent inhibition of human phosphodiesterase-5 by icariin derivatives
Plant extracts traditionally used for male impotence (Tribulus terrestris, Ferula hermonis, Epimedium brevicornum, Cinnamomum cassia), and the individual compounds cinnamaldehyde, ferutinin, and icariin, were screened against phosphodiesterase-5A1 (PDE5A1) activity. Human recombinant PDE5A1 was used as the enzyme source. Only E. brevicornum extract (80% inhibition at 50 μg/mL) and its active principle icariin (1) (IC50 5.9 μM) were active. To improve its inhibitory activity, 1 was subjected to various structural modifications. Thus, 3,7-bis(2-hydroxyethyl)icaritin (5), where both sugars in 1 were replaced with hydroxyethyl residues, potently inhibited PDE5A1 with an IC50 very close to that of sildenafil (IC50 75 vs 74 nM). Thus, 5 was 80 times more potent than 1, and its selectivity versus phosphodiesterase-6 (PDE6) and cyclic adenosine monophosphate-phosphodiesterase (cAMP-PDE) was much higher in comparison with sildenafil. The improved pharmacodynamic profile and lack of cytotoxicity on human fibroblasts make compound 5 a promising candidate for further development.
Dell'Agli, Mario,Galli, Germana V.,Dal Cero, Esther,Belluti, Federica,Matera, Riccardo,Zironi, Elisa,Pagliuca, Giampiero,Bosisio, Enrica
experimental part
p. 1513 - 1517
(2009/09/29)

Icaritin and desmethylicaritin as anti-cancer agents
The antiproliferative effects of Icaritin or Desmethylicaritin on cancer cell lines, both in vitro, and in vivo, are disclosed. Experimental data show that Icaritin and Desmethylicaritin dramatically inhibit the growth of most malignant cells. In addition, both Icaritin and Desmethylicaritin have significant Anti-agiogenesis properties, inhibiting or eliminating entirely the development of new malignant cells. Further, no obvious side effects including nausea, hair loss or body weight loss were found in the animals treated with Icaritin or Desmethylicaritin, making both highly effective anti cancer drugs.
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Page/Page column 2

(2008/12/08)

COSMETIC COMPOSITION CONTAINING HYDROLYSATES OF ICARIIN
The present invention relates to a cosmetic composition containing hydrolysates of icariin, and more particularly, a cosmetic composition containing hydrolysates of icariin including icaritin, icariside I and icariside II. The hydrolysates of icariin is prepared by a method comprising the steps of: (a) obtaining an extract from a plant containing icariin using water or an organic solvent; and (b) hydrolyzing the plant extract with an acid, a base, an enzyme or a microorganism producing the enzyme. The cosmetic composition according to the present invention is employed for anti-oxidant, anti-aging, whitening or anti-wrinkling effects.
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Page/Page column 12-13

(2008/06/13)

EPIMEDINS A, B AND C, FLAVONOID GLYCOSIDES OF EPIMEDIUM KOREANUM HERBS
Three new flavonoid glycosides, epimedins A, B and C, have been isolated from Epimedium koreanum herbs, the structures of which have been elucidated on the basis of chemical and spectroscopic data as shown in formulas I, II and III, respectively.
Oshima, Yoshiteru,Okamoto, Maki,Hikino, Hiroshi
p. 935 - 938
(2007/10/02)