Irilone

CAS# 41653-81-0

Irilone

Catalog No. BCN8188----Order now to get a substantial discount!

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Quality Control of Irilone

Number of papers citing our products

Chemical structure

Irilone

3D structure

Chemical Properties of Irilone

Cas No. 41653-81-0 SDF Download SDF
PubChem ID 5281779 Appearance Powder
Formula C16H10O6 M.Wt 298.25
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 9-hydroxy-7-(4-hydroxyphenyl)-[1,3]dioxolo[4,5-g]chromen-8-one
SMILES C1OC2=C(O1)C(=C3C(=C2)OC=C(C3=O)C4=CC=C(C=C4)O)O
Standard InChIKey NUGRQNBDTZWXTP-UHFFFAOYSA-N
Standard InChI InChI=1S/C16H10O6/c17-9-3-1-8(2-4-9)10-6-20-11-5-12-16(22-7-21-12)15(19)13(11)14(10)18/h1-6,17,19H,7H2
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Irilone

The herbs of Red Clover ( Trifolium pratense)

Biological Activity of Irilone

DescriptionIrilone has immunomodulatory, and α-amylase inhibitory activities, it exhibits the selective inhibition toward CYP3 A4 rather than other major human CYPs. Irilone exhibited prominent antioxidant activities with the IC50 value of 10.46μM. Irilone potentiated the effect of progesterone in both endometrial and ovarian cancer cell lines, it protected dopaminergic neurons against LPS-induced injury through inhibition of microglia activation and proinflammatory factors generation.
TargetsCYP3 A4 | IL Recepter | IFN-γ
In vitro

Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.[Pubmed: 30199256 ]

J Nat Prod. 2018 Sep 28;81(9):1962-1967.

The use of botanical dietary supplements is becoming increasingly popular for the alleviation of hormonal-based conditions such as hot flashes, premenstrual syndrome, and fertility. Estrogen and progesterone receptors (ER and PR) play an essential role in these processes. However, despite the fact that many therapies used to alleviate gynecological conditions act through PR-mediated mechanisms, few studies have investigated or identified any herbal natural product components that act on this receptor.
METHODS AND RESULTS:
In the current study, we used a progesterone response element (PRE)-luciferase (Luc) reporter assay to identify four phytoprogestins present in a standardized red clover ( Trifolium pratense) extract. We found that the component Irilone (1) potentiated the effect of progesterone in both endometrial and ovarian cancer cell lines. In these cancers, progesterone action is generally associated with positive outcomes; thus the potentiating effect of 1 may provide entirely new strategies for enhancing progesterone signaling as a means of mitigating conditions such as fibroids and endometriosis. Formononetin (3) and biochanin A (4) exhibited mixed agonist activity, while prunetin (2) acted only as an antagonist.
CONCLUSIONS:
Collectively, these results suggest that the effects of red clover extract repeatedly observed in cultured cells and the inverse correlation between risk of various cancers and flavonoid intake may be due, in part, to altered progesterone signaling.

8-Hydroxyirilone 5-methyl ether and 8-hydroxyirilone, new antioxidant and α-amylase inhibitors isoflavonoids from Iris germanica rhizomes.[Pubmed: 28069265 ]

Bioorg Chem. 2017 Feb;70:192-198.

Iris species are well recognized as wealthy sources of isoflavonoids.
METHODS AND RESULTS:
In the present study, phytochemical investigation of the rhizomes of Iris germanica (Iridaceae) procure the isolation of two new isoflavonoids namely, 8-hydroxyIrilone 5-methyl ether (2) and 8-hydroxyIrilone (3), along with eight known isoflavonoids: Irilone 4'-methyl ether (1), Irilone (4), irisolidone (5), irigenin S (6), irigenin (7), Irilone 4'-O-β-d-glucopyranoside (8), iridin S (9), and iridin (10). The isolated flavonoids were structurally characterized with the assist of comprehensive spectroscopic analyses (UV, IR, 1D and 2D NMR, and HRMS) and comparing with the published data. They were estimated for their antioxidant and antidaibetic capacities using DPPH and α-amylase inhibition assays, respectively.
CONCLUSIONS:
Compounds 2, 3, and 4 exhibited prominent antioxidant activities with IC50 values of 12.92, 9.23, and 10.46μM, respectively compared to propyl gallate (IC50 7.11μM). Moreover, 2-5 possessed highest α-amylase inhibitory activity with % inhibition 66.1, 78.3, 67.3, and 70.1, respectively in comparison to acarbose (reference α-amylase inhibitor). Additionally, their structure-activity relationship has been discussed.

Protective effect of isoflavones from Trifolium pratense on dopaminergic neurons.[Pubmed: 18675857 ]

Neurosci Res. 2008 Oct;62(2):123-30.

In the present study, protective effect of five isoflavones (formononetin, daidzein, pratensein, calycosin and Irilone) from Trifolium pratense on lipopolysaccharide-induced dopaminergic neurodegeneration was studied for the first time.
METHODS AND RESULTS:
The results showed that all five isoflavones attenuated LPS-induced decrease in dopamine uptake and the number of dopaminergic neurons in a dose-dependent manner in rat mesencephalic neuron-glia cultures. Moreover, they also significantly inhibited LPS-induced activation of microglia and production of tumor necrosis factor-alpha, nitric oxide and superoxide in mesencephalic neuron-glia cultures and microglia-enriched cultures. In addition, the rank order of protective potency of five isoflavones was: pratensein>daidzein>calycosin>formononetin>Irilone.
CONCLUSIONS:
This study suggested that all five isoflavones protected dopaminergic neurons against LPS-induced injury through inhibition of microglia activation and proinflammatory factors generation.

In vivo

Immunomodulatory activity of isoflavones isolated from Iris germanica (Iridaceae) on T-lymphocytes and cytokines.[Pubmed: 19003948 ]

Phytother Res. 2009 Mar;23(3):428-33

The immunomodulatory activities of two isoflavones, 5,7-dihydroxy-6,4'-dimethoxyisoflavone (irisolidone) (1) and 5,4'-dihydroxy-6,7-methylenedioxyisoflavone (Irilone) (2) isolated from Iris germanica (Iridaceae) is reported.
METHODS AND RESULTS:
Their influence on production of T-lymphocytes (CD4+ and CD8+ cells) and T-cell cytokines, namely Th1: IL-2, IFN-gamma and Th2: IL-4 and IL-5 in a dose-dependent manner was studied by flow cytometric method in Balb/c mice. Oral administration of drugs at doses of 0.1-0.8 mg/kg per oral dose showed 1 to possess stimulatory activity on T-cells and Th1 cytokine production, while as 2 acted as an immunosuppressant for both cells and cytokines.
CONCLUSIONS:
The methylated products of 1 and 2 showed a similar trend to that of their parent compounds but their activity was drastically decreased revealing the importance of free phenolic groups for their immunomodulating activities.

Protocol of Irilone

Kinase Assay

Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects.[Pubmed: 29753067 ]

Toxicol Lett. 2018 Sep 15;294:27-36.

The high risk of herb-drug interactions (HDIs) mediated by the herbal medicines and dietary supplements which containing abundant flavonoids had become more and more frequent in our daily life. In our study, the inhibition activities of 44 different structures of flavonoids toward human CYPs were systemically evaluated for the first time.
METHODS AND RESULTS:
According to our results, a remarkable structure-dependent inhibition behavior toward CYP3A4 was observed in vitro. Some flavonoids such as licoflavone (12) and Irilone (30) exhibited the selective inhibition toward CYP3 A4 rather than other major human CYPs. To illustrate the interaction mechanism, the inhibition kinetics of various compounds was further performed. Sophoranone (1), apigenin (10), baicalein (11), 5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone (15), myricetin (23) and kushenol K (38) remarkably inhibited the CYP3 A4-catalyzed bufalin 5'-hydroxylation reaction, with Ki values of 2.17 ± 0.29, 6.15 ± 0.39, 9.18 ± 3.40, 2.30 ± 0.36, 5.00 ± 2.77 and 1.35 ± 0.25 μM, respectively. Importantly, compounds 1, 11, 15, 23 and 38 could significantly inhibit the metabolism of some clinical drugs in vitro, and these drug-drug interactions (DDIs) of myricetin (23) or kushenol K (38) with clinical drug diazepam were further verified in human primary hepatocytes, respectively. Finally, a quantitative structure-activity relationship (QSAR) of flavonoids with their inhibitory effects toward CYP3 A4 was established using computational methods.
CONCLUSIONS:
Our findings illustrated the high risk of herb-drug interactions (HDIs) caused by flavonoids and revealed the vital structures requirement of natural flavonoids for the HDIs with clinical drugs eliminated by CYP3 A4. Our research provided the useful guidance to safely and rationally use herbal medicines and dietary supplements containing rich natural flavonoids components.

Irilone Dilution Calculator

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Preparing Stock Solutions of Irilone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3529 mL 16.7645 mL 33.5289 mL 67.0578 mL 83.8223 mL
5 mM 0.6706 mL 3.3529 mL 6.7058 mL 13.4116 mL 16.7645 mL
10 mM 0.3353 mL 1.6764 mL 3.3529 mL 6.7058 mL 8.3822 mL
50 mM 0.0671 mL 0.3353 mL 0.6706 mL 1.3412 mL 1.6764 mL
100 mM 0.0335 mL 0.1676 mL 0.3353 mL 0.6706 mL 0.8382 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Irilone

Irilone from Red Clover ( Trifolium pratense) Potentiates Progesterone Signaling.[Pubmed:30199256]

J Nat Prod. 2018 Sep 28;81(9):1962-1967.

The use of botanical dietary supplements is becoming increasingly popular for the alleviation of hormonal-based conditions such as hot flashes, premenstrual syndrome, and fertility. Estrogen and progesterone receptors (ER and PR) play an essential role in these processes. However, despite the fact that many therapies used to alleviate gynecological conditions act through PR-mediated mechanisms, few studies have investigated or identified any herbal natural product components that act on this receptor. In the current study, we used a progesterone response element (PRE)-luciferase (Luc) reporter assay to identify four phytoprogestins present in a standardized red clover ( Trifolium pratense) extract. We found that the component Irilone (1) potentiated the effect of progesterone in both endometrial and ovarian cancer cell lines. In these cancers, progesterone action is generally associated with positive outcomes; thus the potentiating effect of 1 may provide entirely new strategies for enhancing progesterone signaling as a means of mitigating conditions such as fibroids and endometriosis. Formononetin (3) and biochanin A (4) exhibited mixed agonist activity, while prunetin (2) acted only as an antagonist. Collectively, these results suggest that the effects of red clover extract repeatedly observed in cultured cells and the inverse correlation between risk of various cancers and flavonoid intake may be due, in part, to altered progesterone signaling.

The isoflavone irilone contributes to the estrogenic potential of dietary supplements containing red clover.[Pubmed:23982890]

Arch Toxicol. 2014 Feb;88(2):309-21.

A recent intervention study demonstrated the occurrence of Irilone as second most abundant isoflavone next to daidzein in human plasma after consumption of a red clover-based dietary supplement (RCDS) containing predominately formononetin >> biochanin A > Irilone (12 % of these isoflavones). To elucidate the relevance of this finding, in the present study (1) the representativeness of the isoflavone composition of the RCDS and (2) the estrogenic activity of Irilone were investigated. Thus, major isoflavones were quantified in eight commercially available RCDS. Furthermore, the estrogenic activities of Irilone and other isoflavones were determined by marker gene expression in Ishikawa and cell proliferation in MCF-7 cells. Irilone amounted to 1.8-10.9 mg/g capsule content and 5-18 % of the three major isoflavones, respectively, demonstrating the general occurrence of Irilone in RCDS. Moreover, Irilone significantly induced the activity of alkaline phosphatase (AlP) as well as AlP, progesterone receptor, and androgen receptor mRNA levels in Ishikawa cells. Furthermore, Irilone significantly induced MCF-7 cell proliferation. Neither 17beta-estradiol (E2)-induced AlP activity nor E2-induced MCF-7 cell proliferation was affected by Irilone. ICI182,780 antagonized IRI-induced effects on both AlP activity and cell proliferation, suggesting an estrogen receptor agonistic mode of action. Taking into account the estrogenic activity of red clover isoflavones (formononetin, biochanin A, prunetin, glycitein) and their biotransformation products (daidzein, genistein, ethylphenol) as well as published plasma levels of isoflavones after consumption of RCDS, Irilone could contribute approximately 50 % of the E2 equivalents estimated for daidzein.

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