Epimedins A, B and C, Flavonoid Glycosides of Epimedium koreanum Herbs

Hikino, Hiroshi; Oshima, Yoshiteru; Okamoto, Maki

doi:10.3987/r-1987-04-0935

Cited by 45 publications

(3 citation statements)

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“…Identification of prenyl flavone glycosides 1 (icariin) [13], 2 (epimedin A), 3 (epimedin B), and 4 (epimedin C) [14] was performed by spectral comparison with literature data.…”

Section: Identificationmentioning

confidence: 99%

Inhibitory Effects of the Aerial Parts of Epimedium koreanum on TPA-Induced Inflammation and Promotion in Two-Stage Carcinogenesis in Mouse Skin

Yasukawa

Whang

2016

J. Pharm. Nutr. Sci.

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Cancer prevention by supplements offers the most cost-effective long-term health strategy. Methanol extracts from the aerial parts of Epimedium koreanum were previously found to inhibit 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammatory ear oedema and tumour promotion by TPA in the two-stage mouse skin carcinogenesis model. Four prenyl flavonol glycosides (1 4) were isolated from the active fraction of this extract, and were identified. The isolated compounds showed inhibitory activity against TPA-induced ear inflammatory ear oedema. The 50% inhibitory dose (ID50) of icariin (1), epimedin A (2), epimedin B (3) and epimedin C (4) for TPA-induced inflammation ranged from 114 to 255 nmol/ear, suggesting greater potency than indomethacin (ID50: 908 nmol/ear), an antiinflammatory drug. Thus, the epimedium herb may be useful in cancer prevention.

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“…Identification of prenyl flavone glycosides 1 (icariin) [13], 2 (epimedin A), 3 (epimedin B), and 4 (epimedin C) [14] was performed by spectral comparison with literature data.…”

Section: Identificationmentioning

confidence: 99%

Inhibitory Effects of the Aerial Parts of Epimedium koreanum on TPA-Induced Inflammation and Promotion in Two-Stage Carcinogenesis in Mouse Skin

Yasukawa

Whang

2016

J. Pharm. Nutr. Sci.

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“…Compounds 7, 8, and 9 were related to icariin, and their terminal sugar moieties attached to the C-2 of rhamnose were glucose, rhamnose, and xylose, respectively. These were called epimedins A (7), B (8), and C (9) (Oshima et al, 1987;Mizuno et al, 1988). Compound 10 was identified as epimedin I (10) (Sun et al, 1998;Zhao et al, 2007), which had glucose attached to the C-3 of rhamnose in icariin.…”

Section: Isolation and Determination Of New Compounds (1-3) From Ehmentioning

confidence: 99%

Prenylflavonoids isolated from Epimedii Herba show inhibition activity against advanced glycation end-products

Nakashima,

Miyashita,

Yoshimitsu

et al. 2024

Front. Chem.

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Introduction: As inhibitors of advanced glycation end products (AGEs), such as pyridoxamine, significantly inhibit the development of retinopathy and neuropathy in rats with streptozotocin-induced diabetes, treatment with AGE inhibitors is believed to be a potential strategy for the prevention of aging, age-related diseases, and lifestyle-related diseases, including diabetic complications. In the present study, the MeOH extract of Epimedii Herba (EH; aerial parts of Epimedium spp.) was found to inhibit the formation of Nε-(carboxymethyl)lysine (CML) and Nω-(carboxymethyl) arginine (CMA) during the incubation of collagen-derived gelatin with ribose.Materials and methods: EH was purchased from Uchida Wakan-yaku Co., and a MeOH extract was prepared. Several steps of column chromatography purified the extract. Each fraction was tested for inhibitory activity by ELISA using monoclonal antibodies for CML and CMA.Results: After activity-guided fractionation and purification by column chromatography, three new prenylflavonoids [named Koreanoside L (1), Koreanoside E1 (2), and Koreanoside E2 (3)] and 40 known compounds (4–43) were isolated from EH, and their inhibitory effects against CML and CMA formation were tested. Among these, epimedokoreanin B (8), epimedonin E (21), epicornunin B (22), and epicornunin F (24) inhibited the formation of both CML and CMA, with epimedokoreanin B (8) having the most potent inhibitory effect among the isolated compounds. To obtain the structure–activity relationships of 8, the phenolic hydroxy groups of 8 were methylated by trimethylsilyl-diazomethane to afford the partially and completely methylated compounds of 8. Prenyl derivatives of propolis (artepillin C, baccharin, and drupanin) were used in the assay.Discussion: As only 8 showed significant activity among these compounds, the catechol group of the B ring and the two prenyl groups attached to the flavanone skeleton were essential for activity. These data suggest that 8 could prevent the clinical complications of diabetes and age-related diseases by inhibiting AGEs.

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“…Tongkat Ali (Radix Eurycomae longifoliae) and Horney Goat weed (Herba Epimedii) are two popular traditional medicine for supporting and treating sexual dysfunction. These medicinal herbs have been reported their abilities to increase the testosterone contents and improve the quantity and quality of sperm (Susumu et al 1985;Oshima et al 1987;Morita et al 1992;Mitsunaga et al 1994;Khari et al 2014;Naseer et al 2015). Consequently, the EE tablet containing 25 mg of Radix Eurycomae longifoliae extract and 200 mg of Herba Epimedii extract (EE tablet) had been developed for these treatments.…”

Section: Introductionmentioning

confidence: 99%

Simultaneous quantification of eurycomanone, epimedin C and icariin in film coated tablets containing Radix Eurycomae longifoliae extract and Herba Epimedii extract using HPLC – DAD

Dung¹,

Thac²,

Thạch³

et al. 2021

PHAR

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Introduction. This study aimed at developing an HPLC-DAD method for simultaneous determination of eurycomanone (EU), epimedin C (EC) and icariin (IC) in EE tablets containing Radix Eurycomae longifoliae extract and Herba Epimedii extract (EE tablets). Methods. Several HPLC conditions (detection wavelength, mobile phase) and sample preparation conditions (type of solvent, ratios of tablet powder and solvent) were investigated. Results. The optimized HPLC condition employed a Shim-Pack RP18 column and a detection wavelength of 254 nm. The mobile phase consisted of acetonitrile and water containing 0.1% H3PO4 in gradient elution. The method was selective, linear, precise (RSD < 2%) and accurate with recoveries in the range of 98.51–104.58% for EU, 96.22–104.80% for EC and 97.50–104.96% for IC. Conclusion. The method for simultaneous quantification of EU, EC and IC in EE tablets by HPLC – DAD was developed and validated for the first time and could be applied for quality control of EE tablets.

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Epimedins A, B and C, Flavonoid Glycosides of Epimedium koreanum Herbs

Cited by 45 publications

References 0 publications

Inhibitory Effects of the Aerial Parts of Epimedium koreanum on TPA-Induced Inflammation and Promotion in Two-Stage Carcinogenesis in Mouse Skin

Inhibitory Effects of the Aerial Parts of Epimedium koreanum on TPA-Induced Inflammation and Promotion in Two-Stage Carcinogenesis in Mouse Skin

Prenylflavonoids isolated from Epimedii Herba show inhibition activity against advanced glycation end-products

Simultaneous quantification of eurycomanone, epimedin C and icariin in film coated tablets containing Radix Eurycomae longifoliae extract and Herba Epimedii extract using HPLC – DAD

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