491-70-3 Usage
Uses
Used in Pharmaceutical Applications:
Luteolin is used as an additive in M9 minimal medium to induce nodF gene expression, which is essential for the production of Nod factors in certain bacteria. It is also used as a reaction supplement for β-galactosidase assay, a common enzyme assay used in molecular biology.
Used in Cancer Research:
Luteolin is employed to induce and elucidate the apoptotic pathway in renal cell carcinoma 786-O cells, providing insights into the potential anti-tumor activity of this flavone against skin papilloma and other cancer conditions.
Used in Analytical Chemistry:
Luteolin serves as a reference standard for qualitatively and quantitatively analyzing luteolin using reverse phase-high performance liquid chromatography with a diode array detector (RP-HPLC-DAD), a technique used to separate, identify, and quantify components in a mixture.
Used in Anti-Inflammatory Studies:
Luteolin is used to elucidate the anti-inflammatory efficacy in pseudorabies virus-infected RAW264.7 cell lines by measuring the production of anti-inflammatory mediators, as well as assessing cell viability and cytotoxicity.
Used in Antioxidant and Radical Scavenging Applications:
As a hydroxylated flavone derivative with strong antioxidant and radical scavenging properties, luteolin is suggested to play a role in cancer prevention and is used in various applications related to oxidative stress and inflammation.
Used in the Food Industry:
Luteolin can be found in various dietary sources such as celery, broccoli, green pepper, parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano, contributing to their antioxidant and health-promoting properties.
Used in the Cosmetic Industry:
Luteolin's antioxidant and anti-inflammatory properties make it a potential candidate for use in the cosmetic industry, where it can be employed in the development of skincare products aimed at reducing inflammation and promoting skin health.
Natural Flavonoids
Luteolin is a very typical kind of natural flavonoid and belongs to weak acidic tetrahydroxy flavonoids. It is widely distributed in the plant kingdom and is mainly presented in honeysuckle, chrysanthemum, Nepeta, Herba Ajuga and some other drugs as well as many kinds of vegetables such as thyme, Brussels sprouts, cabbage, cauliflower, beets, broccoli and carrots. Moreover, it is also distributed in the form of glycosides in celery, green pepper, and basil leaves as well as the fruit shell of the legume plant Arachis hypogaea, Ajuga decumbus, Lonicera japonica Thunb, Gentianaceae plant Gentianopsis paludosa, and Valerianaceae plant Valeriana amurensis Smir. The pure product of Luteolin appears as yellow crystalline powder.
Figure 1 the pale yellow powder of luteolin and its sources of plant.
Solubility
Luteolin is a golden needles product containing a crystal water molecule that is precipitated from ethanol. It is soluble in alcohol and diethyl ether; slightly soluble in hot water, and insoluble in cold water. Its aqueous solution exhibits pleasing yellow and can be dissolved in 10% aqueous solution of sodium hydroxide and appears as dark yellow color. It is stable under normal conditions.
Extraction Method
According to the report of the literature, method for extracting the active ingredient luteolin from the peanut shell includes solvent method, ultrasonic method, microwave method and supercritical CO2 method, wherein the solvent extraction method is the most widely used with the major extraction solvents used being methanol, acetone and ethyl acetate.
The above information is edited by the lookchem of Dai Xiongfeng.
Pharmacological activity
1. Luteolin has various kinds of pharmacological activities. Plants rich in luteolin content are often used as a traditional Chinese medicine for treatment of disease. With the deepening of the study on luteolin, researchers have found that it have anti-cancer activities including inhibiting the proliferation of tumor cell, inducing the apoptosis of tumor cells as well as sensitizing anti-cancer drugs. Moreover, it also has anti-inflammatory, anti-oxidant as well as protein effect on the nervous system.
2. Luteolin is a kind of PDE4 inhibitors, phosphodiesterase inhibitors (2) and interleukin-6 inhibitor (3). It can significantly reverse the induction effect of anesthesia of mice xylazine/ ketamine induction of anesthesia. 4 Preclinical studies have shown that the pharmacological effects of luteolin might include anti-oxidant, anti-inflammatory, antibacterial and anti-cancer. Preliminary studies have found that luteolin can inhibit the apoptosis of the angiogenesis induced cell, affect the tumor growth in animal models, reduce the tumor growth and also improve the cytotoxicity of certain anti-cancer drugs on the tumor cell, indicating that luteolin could be potential cancer chemo-preventive drugs and chemotherapy drugs.
3. The mechanism of biological activity of luteolin may be regulating the level of ROS, inhibition of topoisomerase I and topoisomerase II, reducing the transcription factor NF-κB and AP-1, and stabilizing p53 and inhibition of phosphatidylinositol 3-kinase, signal transduction and activator of transcription 3 (STAT3), insulin-like growth factor 1 receptor (IGF1R) and human epidermal growth factor receptor II activity.
Pharmacological effects
1, anti-tumor: the inhibitory effect of luteolin on tumor cell proliferation is mainly through inhibiting certain intracellular kinase activity and causing cell cycle arrest.
2. Antioxidant: the antioxidant effect of luteolin itself mainly exhibits as a reducing agent involved in the oxidation reaction as well as enhancing the activity of the biological antioxidant system.
3, Anti-inflammatory: the anti-inflammatory activity of luteolin is mainly manifested that it can reduce the activity of inflammatory cytokine transcription factor and production of the pro-inflammatory cytokines and inflammatory mediators.
4, the neuro-protective effect: luteolin has protective effect on the learning and memory ability of the nervous system.
5, anti-fibrosis: luteolin can reduce the extent of liver fibrosis, reduce the hydroxyproline (HYP) in the liver tissue, the content of malondialdehyde (MDA) and the mRNA expression of type I pro-collagen mRNA. In vitro, it can inhibit the proliferation of hepatic star like cells (HSC) and collagen synthesis. It can also alleviate the bleomycin-induced pulmonary fibrosis and histopathological changes, reduce the lung weight index, significantly suppress the increase of MDA, HYP and inhibit the expression of transforming growth factor-β1 (TGF-β1) mRNA in the lung tissue. In vitro, it can inhibit the proliferation of human embryo lung fibroblasts, induce the apoptosis.
6, anti-fertility and hormonal effects: luteolin has a significant dose-dependent anti-implantation activity. After oral administration, it can significantly increase the weight, diameter of uterine, the thickness of endometrium and the height of epithelial cells. Single administration has estrogenic effect while its combination with ethinyloestradiol exhibits anti-estrogenic effect.
7, other functions: luteolin can inhibit various kinds of bacteria and viruses, such as Staphylococcus aureus, Escherichia coli, herpes simplex virus, polio virus, Coxsackie B3 virus. It can inhibit the activity of integrase of AIDS virus HIV-1 and therefore has potential anti-HIV effect. Luteolin is able to bind to the s2 protein of the severe acute respiratory syndrome (SARS) corona virus, thus inhibiting viral for entry into host cells. Luteolin also has inhibitory effect on the Leishmania donovani. Through inhibiting the action of the topoisomerase I and topoisomerase II of Leishmania donovani and inhibit their growth. Additionally, luteolin also has immunomodulatory effects and so on.
Pharmacokinetics
The pharmacokinetic experiment of rat has shown that after the oral administration of luteolin by rats, the in vivo plasma concentration is significantly higher than that after acid hydrolysis which demonstrating it is mostly presented in the glucuronic acid-bound form. The biliary study have found that the level of luteolin in the biliary sample is undetectable using HPLC method at each time after the administration if without the hydrolysis treatment, demonstrating that luteolin is mainly presented in the bound form in the bile.
Indications
This product has antitussive, expectorant effect. The antitussive effect is through suppressing the cough center; the expectorant effect of this product is related to its ability of promoting the secretion of the respiratory tract gland and dissolving the acidic mucopolysaccharides in the sputum. It also has anti-inflammatory, anti-allergic and immune enhancement effect. It also has inhibitory effect on Staphylococcus aureus, Streptococcus pneumoniae and Pseudomonas aeruginosa. It can also be used for the treatment of chronic bronchitis and other respiratory diseases sputum.
Indications
Luteolin compound prescription is mainly used for relieving cough, eliminating
phlegm, diminishing inflammation, treating cardiovascular diseases, and treating amyotrophic
lateral sclerosis, severe acute respiratory syndrome (SARS), hepatitis, etc.
Side effects
Some patients may get dry mouth, upset stomach, dizziness, nausea and other side effects. After prolonged administration, the symptom may gradually disappear.
History
At present, luteolin does not have the application of the proprietary medicine, but as
one of the main active ingredients of medicinal plants, there is a long history of
application. In northern and southern dynasties, honeysuckle with sweet taste, nontoxic, can treat swelling, lose weight, and prolong life under long-term use. In Tang dynasty, honeysuckle was used for treatment of abdominal distension, hot toxic blood dysentery, and water dysentery. It was showed that the clinical application of honeysuckle had made significant progress. During the Song and Yuan dynasties, honeysuckle was widely used for the treatment of diseases such as sore and ulcer. To the Ming dynasty, there were many treatises about honeysuckle. For example, it is said in Compendium of Materia Medica: honeysuckle cure all rheumatism QI and all sorts of swollen poison, ulcer,scab, and heat dissipation detoxify. The prescription has also expanded its scope of application. Up to the Qing dynasty, the application of honeysuckle can not only inherit the theory of the predecessors but also put forward some original ideas and innovation in some respects. In recent years, through the in-depth study of pharmacological effects, it is found that luteolin has significant effects on antitumor, cardioprotection, neuroprotection,respiratory system, immune regulation, anti-inflammatory, spasmolysis, expectorant, anti-allergic, enzyme activities, antioxidant, diuretic, and other aspects.
Biological Activity
Anti-inflammatory, antioxidant and free radical scavenger. Inhibits LPS-induced TNF- α , IL-6 and inducible nitric oxide production and blocks NF- κ B and AP-1 activation. Antiproliferative; inhibits proliferation of Lewis lung carcinoma cells in vivo .
Biochem/physiol Actions
Hydroxylated flavone derivative, a strong antioxidant and radical scavenger. Suggested to play a role in prevention of cancer, possibly via the inhibition of fatty acid synthase activity.
Pharmacology
Luteolin can selectively inhibit the fatty acid synthase activity in prostate cancer and breast cancer cells, which is related to the inhibitory effect of luteolin on tumor cell growth and apoptosis. Luteolin can significantly reduce the incidence of colon cancer and the size of tumor caused by dimethylhydrazine, which may be related to the
regulation of lipid peroxidation, antioxidation, and antiproliferative effect. The anti-inflammatory activity of luteolin is related to the inhibition of nitric oxide (NO) and other inflammatory cytokines such as tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6) generation and inhibition of protein tyrosine phosphorylation and nuclear transcription factor KB (NF-KB)-mediated gene expression. Luteolin can enhance the transfer of synapses in the hippocampus dentate gyrus, causing long-term potentiation. Moreover, in chronic hypoperfusion injury caused by vascular occlusion, luteolin can still protect synapses, causing long-term potentiation, and reduce the escape latency in the Morris water maze test in rats. Luteolin can reduce the degree of hepatic fibrosis, hydroxyproline level in liver tissues (HYP), malondialdehyde (MDA) content, and mRNA expression of procollagen type I and inhibit hepatic stellate cell (HSC) proliferation and collagen synthesis in vitro. Luteolin can also improve the histological changes of pulmonary fibrosis induced by bleomycin, reduce the lung weight index, significantly reduce the increase in MDA and HYP, and inhibit the level of mRNA of transforming
growth factor beta 1 (TGF-β1) in lung tissue. Luteolin in vitro can inhibit the proliferation of human embryonic lung fibroblast cells and promote apoptosis .
Anticancer Research
It is a flavone with yellow crystalline appearance. Dietary sources of luteolin includeoregano, celery, orange, broccoli, rosemary, green pepper, peppermint, parsley,olive oil, thyme, carrot, dandelion, chamomile tea, and perilla. It is found to obstructepithelial-mesenchymal transition (Singh et al. 2016b). It is inhibiting the cancercell proliferation, angiogenesis, and metastasis. In addition, it suppresses thepathways like PI3K/AKT, NF-κB, and X-linked inhibitor of apoptosis protein(XIAP) which enhances the cell growth and function. It also induces apoptosis andtumor suppressor p53. Hence, luteolin can be used as a potential antineoplasticagent in different cancers (Lin et al. 2008).
Clinical Use
The natural extract containing luteolin has been used in clinical treatment of many
diseases. Lamiophlomis rotata Kudo capsule is made from traditional Chinese medicine
Lamiophlomis rotata Kudo, which consists of the medicinal components such as flavonoids, saponins, sterols, amino acids, and many trace elements. Among these components, luteolin content is not less than 0.80 mg/g. This capsule is mainly used for a variety of surgical incision pain, postoperative bleeding, fracture, sprain of muscles, rheumatic pain, dysmenorrhea, uterine bleeding, gingival swelling, and bleeding.
Check Digit Verification of cas no
The CAS Registry Mumber 491-70-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 1 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 491-70:
(5*4)+(4*9)+(3*1)+(2*7)+(1*0)=73
73 % 10 = 3
So 491-70-3 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-6,16-19H
491-70-3Relevant articles and documents
Total synthesis of luteolin
Zhang, Ji,Liu, Man,Cui, Wei,Yang, Jian,Yang, Bo
, p. 60 - 61 (2014)
Luteolin is a naturally-occurring polyphenolic flavonoid compound which has received considerable attention because of its wide range of biological and pharmacological properties. Efficient methods are reported for preparing luteolin, based on the acylation of 1,3,5-trimethoxybenzene and condensation with 3,4-dimethoxybenzaldehyde or the reaction of 3,4-dimethoxycinnamic acid with 1,3,5-trimethoxybenzene. The first of these is the better method.
Ovipositional deterrent in the sweet pepper, Capsicum annuum, at the mature stage against Liriomyza trifolii (Burgess)
Kashiwagi, Takehiro,Horibata, Yoh,Mekuria, Daniel Bisrat,Tebayashi, Shin-Ich,Kim, Chul-Sa
, p. 1831 - 1835 (2005)
Liriomyza trifolii (Burgess), the American serpentine leafminer fly, is well known as a serious pest throughout the world. This insect attack over 21 different plant families including solanaceae plants. The mature sweet pepper, Capsicum annuum (Solanaceae), however, shows resistance to this leafminer fly. This resistance is based on the ovipositional deterrent in the sweet pepper leaf against the fly species. Based on bioassay-guided fractionation, luteolin 7-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside was isolated and identified as the ovipositional deterrent against this insect species. This compound completely deterred L. trifolii females from laying their eggs on a host plant leaf treated at 4.90 μg/cm2.
Anti-inflammatory effect of luteolin is related to the changes in the gut microbiota and contributes to preventing the progression from simple steatosis to nonalcoholic steatohepatitis
Sun, Wen-Long,Yang, Jing-Wen,Dou, Hao-Yue,Li, Gu-Qing,Li, Xin-Yu,Shen, Liang,Ji, Hong-Fang
, (2021)
Increasing intestinal barrier function is one of the basic methods to suppress inflammation in the progression from simple steatosis (SS) to nonalcoholic steatohepatitis (NASH). Luteolin exists widely in vegetables, fruits and natural herbs and has various biological activities, including benefits on nonalcoholic fatty liver disease (NAFLD). However, its regulatory effects on the gut microbiota and involvement in its biological activities remain to be investigated. We fed rats a high-fat diet containing 0.5% luteolin for 12 weeks and determined the effects of luteolin on lipid metabolism, inflammation, and the gut microbiota. Supplementation with luteolin for 12 weeks significantly reduced blood lipids and hepatic lipid levels and improved liver fat accumulation and inflammation. Moreover, supplementation with luteolin led to the significant enrichment of more than 10% of gut bacterial species, which contributed to increase the abundance of ZO-1, reduce intestinal permeability, reduce plasma lipopolysaccharide, and inhibit the TLR4/NF-κB pathway. In summary, the anti-inflammatory effect of luteolin might be related to changes in the gut microbiota and contribute to preventing the progression from SS to NASH. Our research provides new insights into the anti-inflammatory mechanism of luteolin and supports its use as a dietary supplement for NAFLD patients.
Flavonoids from the aerial part of Vicia subvillosa
Yuldashev,Muminova,Drenin,Botirov
, p. 34 - 36 (2007)
The new flavone glucoside viscioside, luteolin-4-O-β-D- galactopyranoside, in addition to the known flavonoids apigenin, luteolin, quercetin, cinaroside, luteolin-4-O-β-D-glucoside, and isoquercitrin were isolated from the aerial part of Vicia subvillosa. Springer Science+Business Media, Inc. 2007.
Flavonoids of carthamus tinctorius flowers
Kurkin,Kharisova
, p. 446 - 448 (2014)
The known flavonoids luteolin, cinaroside, 5-O-methylluteolin, azaleatin (3,7,3′,4′-tetrahydroxy-5-methoxyflavone), and the new natural product 3,7,3′,4′-tetrahydroxy-5-methoxyflavone 7-O-β- Dglucopyranoside (safloroside) were isolated from Carthamus tinctorius flowers and characterized by PMR and UV spectroscopy and mass spectrometry.
COSMETIC COMPOSITION FOR SKIN IMPROVEMENT COMPRISING GREEN BARLEY EXTRACT
-
, (2022/02/05)
Provided is a cosmetic composition for skin improvement including a green barley extract.
Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer
Long, Huan,Hu, Xiaolong,Wang, Baolin,Wang, Quan,Wang, Rong,Liu, Shumeng,Xiong, Fei,Jiang, Zhenzhou,Zhang, Xiao-Qi,Ye, Wen-Cai,Wang, Hao
, p. 12089 - 12108 (2021/09/06)
Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.
Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature
Tamuli, Kashyap J.,Sahoo, Ranjan K.,Bordoloi, Manobjyoti
supporting information, p. 20956 - 20965 (2020/12/31)
Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.
New Flavonoids and Turkesterone-2-O-Cinnamate from Leaves of Rhaponticum uniflorum
Olennikov,Kashchenko
, p. 256 - 264 (2019/05/06)
Leaves of Rhaponticum uniflorum (L.) DC. (Asteraceae) afforded 46 compounds including seven new flavonoids that were identified using UV, IR, and NMR spectroscopy and mass spectrometry as 6-hydroxyluteolin-7-O-(2′-O-caffeoyl)-β-D-glucopyranoside (rhaunoside A, 1), 6-hydroxyluteolin-7-O-(6″-O-cinnamoyl)-β-D-glucopyranoside (rhaunoside B, 2), 6-hydroxyluteolin-4′-O-β-D-glucopyranoside (rhaunoside C, 3), nepetin-7-O-(6″-O-caffeoyl)-β-D-glucopyranoside (rhaunoside D, 4), nepetin-7-O-(6″-O-cinnamoyl)-β-D-glucopyranoside (rhaunoside E, 5), nepetin-3′-O-β-D-glucopyranoside (rhaunoside F, 6), and luteolin-7-O-(2″-O-caffeoyl)-β-D-glucopyranoside (rhaunoside G, 7) and the new ecdysteroid turkesterone-2-O-cinnamate (8).
Enhanced antioxidant activity, antibacterial activity and hypoglycemic effect of luteolin by complexation with manganese(II) and its inhibition kinetics on xanthine oxidase
Dong, Hao,Yang, Xiaocui,He, Jiapeng,Cai, Sheng,Xiao, Kaijun,Zhu, Liang
, p. 53385 - 53395 (2017/12/02)
The present study aims to improve the biological activities of luteolin by complexation with manganese(ii). UV-visible spectroscopy, infrared spectroscopy, thermogravimetric analysis and elemental analysis were adopted to assess the relevant interaction of luteolin and manganese(ii) ions and the chelation sites. The antioxidant activity, hypoglycemic effect and antimicrobial activity of luteolin-manganese(ii) complex with respect to its parent luteolin and the inhibition effect of which on xanthine oxidase were investigated and compared. The spectroscopic data indicated that luteolin reacts with manganese(ii) cations through the chelation sites of 5-hydroxy and 4-carbonyl in two luteolin molecules. Antioxidant and antibacterial activity were enhanced after the complexation of manganese(ii) cations with luteolin. An inhibition effect assay found that luteolin and luteolin-manganese(ii) complex reversibly inhibited xanthine oxidase in a competitive manner. Luteolin-manganese(ii) complex had a more remarkable hypoglycemic effect than luteolin by increasing the glucose consumption in liver tissue.
