Formononetin

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Formononetin
Category Enzyme inhibitors
Catalog number BBF-03884
CAS 485-72-3
Molecular Weight 268.26
Molecular Formula C16H12O4
Purity >98%

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BBF-03884 5 g $269 In stock

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Description

Formononetin is a phytoestrogen from the root of Astragalus membranaceus and an O-methylated isoflavone. It displays a wide variety of biological activityes, including decreasing expression of pro-imflammatory cytokines, inducing apoptosis in prostate cancer cells, lowering systolic blood pressure and inhibiting attachment and motility of Giardia.

Specification

Synonyms Formononetol, Biochanin B; Formononetol Formononetin; NSC 93360; NSC93360; NSC-93360
Storage Store at -20°C
IUPAC Name 7-hydroxy-3-(4-methoxyphenyl)chromen-4-one
Canonical SMILES COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)O
InChI InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
InChI Key HKQYGTCOTHHOMP-UHFFFAOYSA-N

Properties

Appearance Off-white Solid
Application estrogenic; antigiardial; sialidase inhibitor
Boiling Point 479.4°C at 760 mmHg
Melting Point 256-260°C
Density 1.329 g/cm3
Solubility Soluble in DMSO
LogP 3.17420

Reference Reading

1.Low concentration of formononetin stimulates the proliferation of nasopharyngeal carcinoma cell line CNE2 by upregulating bcl-2 and p-ERK1/2 expression.
Guo YH1, Wang Y1, Xin M1. Pharm Biol. 2016 Feb 26:1-6. [Epub ahead of print]
Context Formononetin is a typical phytoestrogen, which is a bioactive component found in red clover plants. Previous studies have shown that formononetin inhibits the proliferation of several types of cancer cells, including prostate cancer and osteosarcoma. However, how formononetin affects the proliferation of CNE2 is not clear. Objective The objective of this study is to investigate the effects of formononetin on nasopharyngeal carcinoma cells in vitro, along with the underlying mechanism. Materials and methods CNE2 cells were incubated with various concentrations of formononetin (0, 0.1, 0.2, 0.3 and 1 μM) for 48 h. Cell proliferation was measured by [3-(4,5-dimethylthiazol-2-yl)]-2,5-diphenyltetrazolium bromide (MTT) assay, while the rate of apoptosis was measured by flow cytometry. Bcl-2 and bax mRNA expression levels were determined by real time polymerase chain reaction (RT-PCR), while p-ERK1/2 and bcl-2 protein expression levels were quantified by Western blotting.
2.Low concentration of formononetin stimulates the proliferation of nasopharyngeal carcinoma cell line CNE2 by upregulating bcl-2 and p-ERK1/2 expression.
Guo YH1, Wang Y1, Xin M1. Pharm Biol. 2016 Feb 26:1-6. [Epub ahead of print]
Context Formononetin is a typical phytoestrogen, which is a bioactive component found in red clover plants. Previous studies have shown that formononetin inhibits the proliferation of several types of cancer cells, including prostate cancer and osteosarcoma. However, how formononetin affects the proliferation of CNE2 is not clear. Objective The objective of this study is to investigate the effects of formononetin on nasopharyngeal carcinoma cells in vitro, along with the underlying mechanism. Materials and methods CNE2 cells were incubated with various concentrations of formononetin (0, 0.1, 0.2, 0.3 and 1 μM) for 48 h. Cell proliferation was measured by [3-(4,5-dimethylthiazol-2-yl)]-2,5-diphenyltetrazolium bromide (MTT) assay, while the rate of apoptosis was measured by flow cytometry. Bcl-2 and bax mRNA expression levels were determined by real time polymerase chain reaction (RT-PCR), while p-ERK1/2 and bcl-2 protein expression levels were quantified by Western blotting.
3.Methoxyisoflavones formononetin and isoformononetin inhibit the differentiation of Th17 cells and B-cell lymphopoesis to promote osteogenesis in estrogen-deficient bone loss conditions.
Mansoori MN1, Tyagi AM, Shukla P, Srivastava K, Dev K, Chillara R, Maurya R, Singh D. Menopause. 2016 May;23(5):565-76. doi: 10.1097/GME.0000000000000646.
OBJECTIVE: Recent studies have shown that immune system plays a major role in pathophysiology of postmenopausal osteoporosis. Previously we have shown that phytoestrogens like daidzein and medicarpin exhibit immunoprotective effects, by virtue of which they alleviate bone loss. With this background, methoxyisoflavones like formononetin (formo) and isoformononetin (isoformo) that have been studied for preventing bone loss in ovariectomized rats were tested for their immunomodulatory effects in estrogen-deficient bone loss mice model.

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