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3-((6-deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, icariin

No.	Title	Href
1	Icariin-mediated inhibition of NF-κB activity enhances the in vitro and in vivo antitumour effect of 5-fluorouracil in colorectal cancer. Cell Biochem Biophys. 2014 Jul;69(3):523-30. doi: 10.1007/s12013-014-9827-5.	`Click`
2	Arsenic Trioxide and Icariin Show Synergistic Anti-leukemic Activity. Cell Biochem Biophys. 2015 Sep;73(1):213-9. doi: 10.1007/s12013-015-0660-2.	`Click`
3	Icariin potentiates the antitumor activity of gemcitabine in gallbladder cancer by suppressing NF-κB. Acta Pharmacol Sin. 2013 Feb;34(2):301-8. doi: 10.1038/aps.2012.162.	`Click`

No.

Title

Href

Icariin-mediated inhibition of NF-κB activity enhances the in vitro and in vivo antitumour effect of 5-fluorouracil in colorectal cancer. Cell Biochem Biophys. 2014 Jul;69(3):523-30. doi: 10.1007/s12013-014-9827-5.

Click

Arsenic Trioxide and Icariin Show Synergistic Anti-leukemic Activity. Cell Biochem Biophys. 2015 Sep;73(1):213-9. doi: 10.1007/s12013-015-0660-2.

Click

Icariin potentiates the antitumor activity of gemcitabine in gallbladder cancer by suppressing NF-κB. Acta Pharmacol Sin. 2013 Feb;34(2):301-8. doi: 10.1038/aps.2012.162.

Click

Name	Icariin
PubChem CID	5318997
Molecular Weight	676.7g/mol
Synonyms	3-((6-deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, icariin
Formula	C₃₃H₄₀O₁₅
SMILES	CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
InChI	1S/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
InChIKey	TZJALUIVHRYQQB-XLRXWWTNSA-N
CAS Number	489-32-7
ChEMBL ID	CHEMBL553204
ChEBI ID	CHEBI:78420
Herb ID	HBIN029922
Drug Bank ID	DB12052
KEGG ID	C17555
Structure		Download 2D MOL 3D MOL

Chineses Pinyin	WuShanYinYangHuo
Use Part	Aerial Parts
Habitat	ZheJiang, AnHui, HuNan, HuBei
Flavor	Pungent, Sweet
Meridian Tropism	Liver, Kidney
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Ranunculales 　　　　-->Family: Berberidaceae 　　　　　-->Genus: Epimedium 　　　　　　-->Species: Epimedium wushanense

Chineses Pinyin	YinYangHuo
Use Part	Leaf
Habitat	HeiLongJiang, JiLin, LiaoNing, ShanDong, JiangSu, JiangXi, HuNan, GuangXi, SiChuan, GuiZhou, Shaanxi, GanSu
Flavor	Pungent, Sweet
Meridian Tropism	Liver, Kidney
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Ranunculales 　　　　-->Family: Berberidaceae 　　　　　-->Genus: Epimedium 　　　　　　-->Species: Epimedium brevicornu

Chineses Pinyin	ChaoXianYinYangHuo
Use Part	Aerial Parts
Habitat	North Korea, Japan , JiLin, LiaoNing, ZheJiang, AnHui
Flavor	Pungent
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Ranunculales 　　　　-->Family: Berberidaceae 　　　　　-->Genus: Epimedium 　　　　　　-->Species: Epimedium koreanum

Pair Name	Icariin, Fluorouracil
Partner Name	Fluorouracil
Disease Info	[ICD-11: 2B91]	Colorectal cancer		Investigative
Biological Phenomena	Induction-->Apoptosis
Gene Regulation	Up-regulation	Expression	BAX	hsa581
	Down-regulation	Expression	BCL-xL	hsa598
	Up-regulation	Cleavage	CASP3	hsa836
	Up-regulation	Cleavage	CASP8	hsa841
	Up-regulation	Cleavage	CASP9	hsa842
	Down-regulation	Expression	CCND1	hsa595
	Down-regulation	Expression	NFKB1	hsa4790
	Up-regulation	Cleavage	PARP1	hsa142
In Vitro Model	HT-29	Colon adenocarcinoma	Homo sapiens (Human)	CVCL_0320
In Vitro Model	HCT 116	Colon carcinoma	Homo sapiens (Human)	CVCL_0291
In Vivo Model	HCT116 cells were injected into nude mice, tumour appearance was inspected twice a week.
Result	We suggest that combination of icariin with 5-FU might offer a therapeutic benefit to the patients with CRC; however, further studies are required to ascertain this proposition.

Pair Name	Icariin, Arsenic oxide (As2O3)
Partner Name	Arsenic oxide (As2O3)
Disease Info	[ICD-11: XH1A50]	Acute promyelocytic leukemia		Investigative
Gene Regulation	Up-regulation	Cleavage	CASP3	hsa836
	Up-regulation	Cleavage	PARP1	hsa142
	Up-regulation	Expression	ROS1	hsa6098
In Vitro Model	HL-60	Adult acute myeloid leukemia	Homo sapiens (Human)	CVCL_0002
In Vitro Model	NB4	Acute promyelocytic leukemia	Homo sapiens (Human)	CVCL_0005
Result	Our results showed that Icariin, by increasing intracellular ROS, exhibited antitumor activity and potentiated the antitumor activity of ATO against APL. Therefore, combination treatment with Icariin and ATO might offer a novel therapeutic option for patients with APL, although further studies are needed.

Pair Name	Icariin, Gemcitabine
Partner Name	Gemcitabine
Disease Info	[ICD-11: 2C94]	Bladder cancer		Investigative
Biological Phenomena	Induction-->Blockade of cell cycle in G0/G1 phase
Gene Regulation	Down-regulation	Expression	BCL2	hsa596
	Down-regulation	Expression	BCL-xL	hsa598
	Down-regulation	Expression	BIRC5	hsa332
	Down-regulation	Expression	CASP3	hsa836
	Down-regulation	Activity	NFKB1	hsa4790
	Up-regulation	Expression	PARP1	hsa142
In Vitro Model	GBC-SD	Gallbladder carcinoma	Homo sapiens (Human)	CVCL_6903
In Vitro Model	SGC-996	Gallbladder carcinoma	Homo sapiens (Human)	CVCL_M737
In Vivo Model	1×10⁵ GBC-SD cells were injected subcutaneously into the right and left abdominal regions with a gauge needle.
Result	Icariin, by suppressing NF-κB activity, exerts antitumor activity, and potentiates the antitumor activity of gemcitabine in gallbladder cancer. Combined administration of gemcitabine and icariin may offer a better therapeutic option for the patients with gallbladder cancer.