Catalogue Number
BF-E2012
Analysis Method
HPLC,NMR,MS
Specification
98%
Storage
2-8°C
Molecular Weight
822.8
Appearance
White crystalline powder
Botanical Source
Epimedium brevicornu,Gymnema sylvestre
Structure Type
Flavonoids
Category
Standards;Natural Pytochemical;API
SMILES
CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=C(C3=O)C(=CC(=C4CC=C(C)C)OC5C(C(C(C(O5)CO)O)O)O)O)C6=CC=C(C=C6)OC)C)O)O)O)O)O
Synonyms
4H-1-Benzopyran-4-one, 3-[[6-deoxy-2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-mannopyranosyl]oxy]-7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-/Epmedin C/3-{[6-Deoxy-2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-mannopyranosyl]oxy}-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl β-D-glucopyranoside/4H-1-Benzopyran-4-one, 3-((6-deoxy-2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-mannopyranosyl)oxy)-7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-/N1912/X1133/Epimedin C/3-{[6-Deoxy-2-O-(6-deoxy-α-L-mannopyranosyl)-α-L-mannopyranosyl]oxy}-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4-oxo-4H-chromen-7-yl β-D-glucopyranoside
IUPAC Name
3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Density
1.6±0.1 g/cm3
Solubility
Methanol
Flash Point
322.2±27.8 °C
Boiling Point
1062.1±65.0 °C at 760 mmHg
Melting Point
InChl
InChI=1S/C39H50O19/c1-14(2)6-11-19-21(54-38-32(50)29(47)26(44)22(13-40)55-38)12-20(41)23-27(45)35(33(56-34(19)23)17-7-9-18(51-5)10-8-17)57-39-36(30(48)25(43)16(4)53-39)58-37-31(49)28(46)24(42)15(3)52-37/h6-10,12,15-16,22,24-26,28-32,36-44,46-50H,11,13H2,1-5H3/t15-,16-,22+,24-,25-,26+,28+,29-,30+,31+,32+,36+,37-,38+,39-/m0/s1
InChl Key
ULZLIYVOYYQJRO-JIYCBSMMSA-N
WGK Germany
RID/ADR
HS Code Reference
2932900000
Personal Projective Equipment
Correct Usage
For Reference Standard and R&D, Not for Human Use Directly.
Meta Tag
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COA
31545266
Bone nonunion remains a challenge during the treatment of bone defect accompanied with infection. Epimedii herba is a widely used medicine in clinic to enhance bone healing. Epimedin C and icariin are the major flavonoid glycosides from Epimedii herba. Although the effects of these compounds have been reported, their different absorption and utilisation by osteoblasts remain unclear. In the present study, lipopolysaccharide (LPS)-induced osteoblast was adopted as the model cell to evaluate the effects of epimedin C and icariin. The intracellular and extracellular drug concentrations within 24 h were assayed by pipette tip solid-phase extraction and high-performance liquid chromatography, respectively. MTT, alkaline phosphatase (ALP) and calcified nodule staining were performed to identify and evaluate the effects of epimedin C and icariin on LPS-induced osteoblasts. The regulatory roles of epimedin C and icariin in the bone morphogenetic protein-2 (BMP-2)/Runt-related transcription factor 2 (Runx2) signalling pathway were investigated. The results revealed that epimedin C and icariin were not efficiently absorbed by LPS-induced osteoblasts. Nevertheless, they still had high utilisation efficiency after entering the cells. ALP activity, mineralisation and osteoblasts proliferation were enhanced by a high concentration of epimedin C and icariin. The suppressed expression of BMP-2 and Runx2 in LPS-induced osteoblasts was up-regulated significantly after treatment with epimedin C and icariin. These findings firstly illustrated the behavior of epimedin C and icariin from Epimedii herba on LPS-induced osteoblasts and the regulatory property on the expression of key genes and proteins of the BMP-2/Runx2 signalling pathway, which might be helpful for better understanding flavonoids’ mechanism to enhance bone repair and improving their future application.
Copyright © 2019 The Authors. Published by Elsevier Masson SAS.. All rights reserved.
Absorption and utilisation; Bone morphogenetic protein-2/runt-related transcription factor 2 signalling pathway; Epimedii herba; Lipopolysaccharide; Osteoblast
Absorption and utilisation of epimedin C and icariin from Epimedii herba, and the regulatory mechanism via the BMP2/ Runx2 signalling pathway.
Huang X1, Wang X1, Zhang Y1, Shen L2, Wang N1, Xiong X3, Zhang L4, Cai X5, Shou D6.
2019 Oct;
31204351
Endothelial cell injury and apoptosis induced by oxidative stress serve important roles in many vascular diseases. The repair of endothelial cell vascular injury relies on the function of local endothelial progenitor cells (EPCs). Our previous study indicated that epimedin C, a major flavonoid derived from Herba epimedii (yin yang huo), could promote vascularization by inducing endothelial-like differentiation of mesenchymal stem cells C3H/10T1/2 both in vivo and in vitro. In view of the significant cardiovascular protective effects of Herba epimedii, we detected a protective effect of epimedin C on hydrogen peroxide (H2O2)-induced peroxidation injury in human umbilical vein endothelial cells (HUVECs) and the role of EPC in this process. The results show that epimedin C increased the expression of the stem cell marker, CD34 and PROM1, and subsequently enhanced the expression and function of vascular endothelial growth factor and matrix metalloproteinase (MMP)-2 in local vascular endothelial cells. In conclusion, epimedin C protects H2O2-induced peroxidation injury by enhancing the function of endothelial progenitor HUVEC populations.
Chinese herb; Herba epimedii; endothelial progenitor cell; epimedin C; human umbilical vein endothelial cell; peroxidation injury
Epimedin C Protects H2O2-Induced Peroxidation Injury by Enhancing the Function of Endothelial Progenitor HUVEC Populations.
Wei DH1, Deng JL2, Shi RZ2, Ma L2, Shen JM2, Hoffman R2,3, Hu YH1, Wang H2, Gao JL2.
2019 Sep 1
31203178
Herba Epimedii is a traditional Chinese herbal medicine that contains a mixture of bioactive flavonoid glycosides. Among them, icariin has the most outstanding bioactive functions, while epimedin C exhibits substantial toxicity. A recombinant α-L-rhamnosidase (synAnRhaE) from Aspergillus nidulans was expressed in Escherichia coli to promote the efficient bioconversion of epimedin C to icariin. A hydrolase activity of 574.5 U L-1 was acquired via optimized fed-batch fermentation in a 5-L bioreactor. The enzyme proved to be stable in an acidulous pH range below 55 °C with an optimal pH of 4.5 and optimal temperature of 55 °C. Epimedin C (1 g L-1) was 100% converted to icariin within 90 min using recombinant cells. The resting cells proved to be selective for epimedin C and 2″-O-rhamnosylicariside II in crude extracts of the epimedium plant. This work provides an original and efficient biocatalyst system that can be applied in industrialized production of icariin.
Copyright © 2019 Elsevier Ltd. All rights reserved.
Aspergillus nidulans; Bioconversion; Epimedin C; Icariin; α-L-Rhamnosidase
Efficient bioconversion of epimedin C to icariin by a glycosidase from Aspergillus nidulans.
Lyu Y1, Zeng W1, Du G2, Chen J1, Zhou J3.
2019 Oct;
