icariside II
None found
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5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one (Click)
CAS Number: 113558-15-9Picture of molecule
Nikkaji Web: J370.001A
MDL: MFCD15071140
XlogP3-AA: 3.50 (est)
Molecular Weight: 514.52810000
Formula: C27 H30 O10
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidant, bleaching agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 1.181 mg/L @ 25 °C (est)
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Organoleptic Properties:
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
bleaching agents
skin conditioning
skin protecting agents
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BOC Sciences
For experimental / research use only.
Icariside II
Odor: characteristic
Use: A regulator of CXCR4 expression
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Safety Information:
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antioxidant, bleaching agents
Recommendation for icariside II usage levels up to:
 not for fragrance use.
Recommendation for icariside II flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5488822
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0113558159
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NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5488822
Pubchem (sid): 135116385
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
None Found
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 epimedium davidii
Search Trop  Picture
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 baohuoside I
4H-1-benzopyran-4-one, 3-[(6-deoxy-a-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-
 icarlin II
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Google Patents: Use of icariside II in manufacture of products for preventing or treating male or female sexual dysfunction
PubMed: Icariside II, a novel phosphodiesterase-5 inhibitor, attenuates streptozotocin-induced cognitive deficits in rats.
PubMed: Icariside II, a natural mTOR inhibitor, disrupts aberrant energy homeostasis via suppressing mTORC1-4E-BP1 axis in sarcoma cells.
PubMed: Preparation and evaluation of icariside II-loaded binary mixed micelles using Solutol HS15 and Pluronic F127 as carriers.
PubMed: Optimized Biotransformation of Icariin into Icariside II by β-Glucosidase from Trichoderma viride Using Central Composite Design Method.
PubMed: Icariside II protects against cerebral ischemia-reperfusion injury in rats via nuclear factor-κB inhibition and peroxisome proliferator-activated receptor up-regulation.
PubMed: Icariside II inhibits the EMT of NSCLC cells in inflammatory microenvironment via down-regulation of Akt/NF-κB signaling pathway.
PubMed: Beneficial Effects of a Flavonoid Fraction of Herba Epimedii on Bone Metabolism in Ovariectomized Rats.
PubMed: Metabolite Profiles of Icariin in Rat Feces, Bile and Urine by Ultraperformance Liquid-Chromatography/Quadrupole-Time-of-Flight Mass Spectrometry.
PubMed: [HPLC-PDA-CAD Fingerprints of Salt Anemarrhenae Rhizoma].
PubMed: [Quality Analysis and Evaluation of Anemarrhena asphodeloides Rhizome from Different Habitats].
PubMed: Optimization and anticancer activity in vitro and in vivo of baohuoside I incorporated into mixed micelles based on lecithin and Solutol HS 15.
PubMed: Comparative Pharmacokinetics Study of Icariin and Icariside II in Rats.
PubMed: Evaluation of medicinal value of Epimedium elatum on the basis of pharmacologically active constituents, Icariin and Icariside-II.
PubMed: Icariside II ameliorates diabetic nephropathy in streptozotocin-induced diabetic rats.
PubMed: [Optimization of extraction technology of compatibility of couplet medicines Epimedium brevicornu and Ligusticum chuanxiong by orthogonal design].
PubMed: TPGS/Phospholipids Mixed Micelles for Delivery of Icariside II to Multidrug-Resistant Breast Cancer.
PubMed: Targeting Apoptosis and Multiple Signaling Pathways with Icariside II in Cancer Cells.
PubMed: Icariside II promotes osteogenic differentiation of bone marrow stromal cells in beagle canine.
PubMed: Icariside II-induced mitochondrion and lysosome mediated apoptosis is counterbalanced by an autophagic salvage response in hepatoblastoma.
PubMed: Regio-selective deglycosylation of icariin by cell suspension cultures of Glycyrrhiza uralensis and Morus alba.
PubMed: Anti-Androgenic Activity of Icarisid II from Epimedium Herb in Prostate Cancer LNCaP Cells.
PubMed: [Optimization of process of icraiin be hydrolyzed to Baohuoside I by cellulase based on Plackett-Burman design combined with CCD response surface methodology].
PubMed: Antioxidant icariside II combined with insulin restores erectile function in streptozotocin-induced type 1 diabetic rats.
PubMed: Icariside II prevents high-glucose-induced injury on human cavernous endothelial cells through Akt-eNOS signaling pathway.
PubMed: Bu-Shen-Yi-Qi formulae suppress chronic airway inflammation and regulate Th17/Treg imbalance in the murine ovalbumin asthma model.
PubMed: Effects of Icariside II on corpus cavernosum and major pelvic ganglion neuropathy in streptozotocin-induced diabetic rats.
PubMed: Synergistic inhibitory effect of Icariside II with Icaritin from Herba Epimedii on pre-osteoclastic RAW264.7 cell growth.
PubMed: Baohuoside I suppresses invasion of cervical and breast cancer cells through the downregulation of CXCR4 chemokine receptor expression.
PubMed: Implications for differentiation of endogenous stem cells: therapeutic effect from icariside II on a rat model of postprostatectomy erectile dysfunction.
PubMed: Icariside II inhibits cell proliferation and induces cell cycle arrest through the ROS-p38-p53 signaling pathway in A375 human melanoma cells.
PubMed: Prophylactic protective effects and its potential mechanisms of IcarisideII on streptozotocin induced spermatogenic dysfunction.
PubMed: Rapid characterization and determination of multiple components in Bu-Shen-Yi-Qi-Fang by high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry.
PubMed: [Two-dimensional zebrafish model combined with hyphenated chromatographic techniques for evaluation anti-osteoporosis activity of epimendin A and its metabolite baohuoside I].
PubMed: Blockade of epidermal growth factor receptor/mammalian target of rapamycin pathway by Icariside II results in reduced cell proliferation of osteosarcoma cells.
PubMed: Ultra-performance liquid chromatography/quadrupole-time-of-flight mass spectrometry analysis of icariside II metabolites in rats.
PubMed: Icariside II improves cerebral microcirculatory disturbance and alleviates hippocampal injury in gerbils after ischemia-reperfusion.
PubMed: [Analysis on biotransformation of Epimedium brevicornu flavonoids].
PubMed: BuShenYiQi Formula strengthens Th1 response and suppresses Th2-Th17 responses in RSV-induced asthma exacerbated mice.
PubMed: Flavonoids from Herba epimedii selectively activate estrogen receptor alpha (ERα) and stimulate ER-dependent osteoblastic functions in UMR-106 cells.
PubMed: [Study on different factors affecting the bionic enzymatic hydrolysis of icariin].
PubMed: A comparative study on the metabolism of Epimedium koreanum Nakai-prenylated flavonoids in rats by an intestinal enzyme (lactase phlorizin hydrolase) and intestinal flora.
PubMed: [Flavonoids from leaves of Epimedium pubescens].
PubMed: Icariside II induces apoptosis via inhibition of the EGFR pathways in A431 human epidermoid carcinoma cells.
PubMed: Pharmacokinetic study of icariside II after a single dose administration of YiGu capsule in healthy Chinese volunteers.
PubMed: [Effects of four kinds of Chinese medicine monomer on growth of PANC-1 xenograft tumor and studying of molecular mechanism].
PubMed: Effect of β-cyclodextrin complexation on solubility and enzymatic hydrolysis rate of icariin.
PubMed: Icariside II reduces testosterone production by inducing necrosis in rat Leydig cells.
PubMed: A new strategy for the discovery of epimedium metabolites using high-performance liquid chromatography with high resolution mass spectrometry.
PubMed: [Affect regularity of medicinal species and heating time on flavonoids contents in Epimedium cut crude drug].
PubMed: Icariside II induces apoptosis of melanoma cells through the downregulation of survival pathways.
PubMed: [Screening of bioactive components in epimedium for osteoporosis treatment by model population analysis].
PubMed: Drug-Drug Interactions Potential of Icariin and Its Intestinal Metabolites via Inhibition of Intestinal UDP-Glucuronosyltransferases.
PubMed: A novel drug-phospholipid complex loaded micelle for baohuoside I enhanced oral absorption: in vivo and in vivo evaluations.
PubMed: Preparation of a nanoscale baohuoside I-phospholipid complex and determination of its absorption: in vivo and in vitro evaluations.
PubMed: [Comparative study on chemical quality of main species of epimedium].
PubMed: Herba epimedii flavonoids suppress osteoclastic differentiation and bone resorption by inducing G2/M arrest and apoptosis.
PubMed: Induction of apoptosis by Icariside II through extrinsic and intrinsic signaling pathways in human breast cancer MCF7 cells.
PubMed: Functions and action mechanisms of flavonoids genistein and icariin in regulating bone remodeling.
PubMed: Icariside II potentiates paclitaxel-induced apoptosis in human melanoma A375 cells by inhibiting TLR4 signaling pathway.
PubMed: Effect of icarisid II on diabetic rats with erectile dysfunction and its potential mechanism via assessment of AGEs, autophagy, mTOR and the NO-cGMP pathway.
PubMed: Reactive oxygen species-mediated mitochondrial pathway is involved in Baohuoside I-induced apoptosis in human non-small cell lung cancer.
PubMed: Preparation of icariside II-phospholipid complex and its absorption across Caco-2 cell monolayers.
PubMed: Metabolite profiles of icariin in rat plasma by ultra-fast liquid chromatography coupled to triple-quadrupole/time-of-flight mass spectrometry.
PubMed: Icariside II induces apoptosis in U937 acute myeloid leukemia cells: role of inactivation of STAT3-related signaling.
PubMed: Effects of icariside II on improving erectile function in rats with streptozotocin-induced diabetes.
PubMed: Influence of vitamin E tocopherol polyethylene glycol succinate 1000 on intestinal absorption of icariside II.
PubMed: Metabolite profiling of four major flavonoids of Herba Epimedii in zebrafish.
PubMed: Icariin and its derivative icariside II extend healthspan via insulin/IGF-1 pathway in C. elegans.
PubMed: Icariside II enhances Nrf2 nuclear translocation to upregulate phase II detoxifying enzyme expression coupled with the ERK, Akt and JNK signaling pathways.
PubMed: [Effects of icariin and icariside II on eNOS expression and NOS activity in porcine aorta endothelial cells].
PubMed: The flavonoid Baohuoside-I inhibits cell growth and downregulates survivin and cyclin D1 expression in esophageal carcinoma via β-catenin-dependent signaling.
PubMed: [The changes of iNOS and NO in the osteogenic differentiation process of rat bone marrow stromal cells promoted by icariside II].
PubMed: Icarisid II, a PDE5 inhibitor from Epimedium wanshanense, increases cellular cGMP by enhancing NOS in diabetic ED rats corpus cavernosum tissue.
PubMed: [Comparative study on the osteogenic differentiation of rat bone marrow stromal cells effected by icariin and icariside II].
PubMed: Role of intestinal hydrolase in the absorption of prenylated flavonoids present in Yinyanghuo.
PubMed: Janus activated kinase 2/signal transducer and activator of transcription 3 pathway mediates icariside II-induced apoptosis in U266 multiple myeloma cells.
PubMed: [Quality research on Epimedium cut crude drug processed with oil].
PubMed: Simultaneous determination of seven flavonoids in dog plasma by ultra-performance liquid chromatography-tandem mass spectrometry and its application to a bioequivalence study of bioactive components in Herba Epimedii and Er-Xian Decoction.
PubMed: Liquid chromatography-tandem mass spectrometry analysis of metabolites in rats after administration of prenylflavonoids from Epimediums.
PubMed: [Absorption and metabolism of flavonoids in Herba Epimedii via rat intestinal perfusion model].
PubMed: [Research on variation regularity of five main flavonoids contents in Epimedium and processed Epimedium].
PubMed: Preparation of icariside II from icariin by enzymatic hydrolysis method.
PubMed: [Sampling in quality control of medicinal materials-A case of Epimedium].
PubMed: Pharmacokinetics of prenylflavonoids and correlations with the dynamics of estrogen action in sera following ingestion of a standardized Epimedium extract.
PubMed: Cyclooxygenase-2/prostaglandin E2 pathway mediates icariside II induced apoptosis in human PC-3 prostate cancer cells.
PubMed: Effect of stability of internal standard on quantification of 15 flavonoids in Epimedium using CZE.
PubMed: Simple and sensitive liquid chromatography-tandem mass spectrometry assay for simultaneous measurement of five Epimedium prenylflavonoids in rat sera.
PubMed: Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula.
PubMed: Intestinal absorption mechanisms of prenylated flavonoids present in the heat-processed Epimedium koreanum Nakai (Yin Yanghuo).
PubMed: Statistically designed enzymatic hydrolysis for optimized production of icariside II as a novel melanogenesis inhibitor.
PubMed: Simultaneous determination of nine flavonoids and qualitative evaluation of Herba Epimedii by high performance liquid chromatography with ultraviolet detection.
PubMed: Simultaneous determination of icariin, icariside II and osthole in rat plasma after oral administration of the extract of Gushudan (a Chinese compound formulation) by LC-MS/MS.
PubMed: Icariside II from Epimedium koreanum inhibits hypoxia-inducible factor-1alpha in human osteosarcoma cells.
PubMed: A rapid method for simultaneous determination of 15 flavonoids in Epimedium using pressurized liquid extraction and ultra-performance liquid chromatography.
PubMed: Icaritin and its glycosides enhance osteoblastic, but suppress osteoclastic, differentiation and activity in vitro.
PubMed: LC-MS/MS method for the simultaneous determination of icariin and its major metabolites in rat plasma.
PubMed: [Comparison of antioxidative and antitumor activities of six flavonoids from Epimedium koreanum].
PubMed: Simultaneous determination of 15 flavonoids in Epimedium using pressurized liquid extraction and high-performance liquid chromatography.
PubMed: Effect of Baohuoside-1 aglycone and tacrolimus monotherapy and combination therapy on prevention of acute heart allograft rejection in the rat.
PubMed: Multiple conformations of phosphodiesterase-5: implications for enzyme function and drug development.
PubMed: Baohuoside-1 inhibits activated T cell proliferation at G(1)-S phase transition.
PubMed: Determination of rat urinary metabolites of icariin in vivo and estrogenic activities of its metabolites on MCF-7 cells.
PubMed: Preparative isolation and purification of three flavonoids from the Chinese medicinal plant Epimedium koreamum Nakai by high-speed counter-current chromatography.
PubMed: Baohuoside-1, a novel immunosuppressive molecule, inhibits lymphocyte activation in vitro and in vivo.
PubMed: [Chemical constituents of the root of Epimedium acumiantum Franch].
PubMed: Isolation and immunomodulatory effect of flavonol glycosides from Epimedium hunanense.
PubMed: Flavonoids from Epimedium wanshanense.
PubMed: [Chemical constituents from the aerial part of Epimedium brevicornum Maxim].
PubMed: Immunopharmacology and toxicology of the plant flavonoid baohuoside-1 in mice.
PubMed: [Studies on the chemical constituents of Epimedium acuminatum Franch].
PubMed: In vitro immunopharmacological profile of the plant flavonoid baohuoside-1.
PubMed: Effects of the plant flavonoid baohuoside-1 on cancer cells in vitro.
PubMed: [Studies on the isolations and structures of baohuosides-I, VI, VII and baohuosu].
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