Hesperidin

  • CAT Number: I003886
  • CAS Number: 520-26-3
  • Purity: ≥95%
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Hesperidin (CAT: I003886) is a flavonoid glycoside found abundantly in citrus fruits, particularly in the peels and pulp. It has been studied for its various pharmacological properties and potential health benefits. Hesperidin exhibits antioxidant activity, helping to neutralize free radicals and protect cells from oxidative stress. It also has anti-inflammatory effects, which can contribute to reducing inflammation in the body. Hesperidin is known for its potential cardiovascular benefits, including improving blood vessel health, reducing blood pressure, and lowering cholesterol levels. Additionally, it may have anticancer properties and can support the immune system. Hesperidin is commonly used as a dietary supplement and is considered safe for consumption.

Catalog Number I003886
CAS Number 520-26-3
Purity 95%
Solubility DMSO ≥122mg/mL Water <1mg/mL Ethanol <1mg/mL
Storage 3 years -20C powder
IC50 hesperidin (IC50=116.68μmo/L))
IUPAC Name (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
InChI InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
InChIKey QUQPHWDTPGMPEX-QJBIFVCTSA-N
SMILES CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
Reference

[1]. Curr Med Chem. 2018;25(37):4929-4945. doi: 10.2174/0929867324666170718104412.<br />
Potential Anti-inflammatory Effects of Hesperidin from the Genus Citrus.<br />
Tejada S(1), Pinya S(2), Martorell M(3), Cap&oacute; X(4), Tur JA(4)(5), Pons A(4)(5), Sureda A(4)(5).<br />
Author information: (1)Experimental Laboratory, Research Unit, Son Llatzer Hospital, IUNICS, Ctra. Manacor km 4, E-07198, Palma de Mallorca, Balearic Islands, Spain. (2)Group of Interdisciplinary Ecology (EI). Biology Department. University of the Balearic Islands, E-07122 Palma de Mallorca, Spain. (3)Nutrition and Dietetics Department, School of Pharmacy, University of Concepcion, 4070386 Concepcion, VIII – Bio Bio Region, Chile. (4)Research Group on Community Nutrition and Oxidative Stress, University of Balearic Islands, E-07122 Palma de Mallorca, Balearic Islands, Spain. (5)CIBEROBN (Physiopathology of Obesity and Nutrition), E- 07122 Palma de Mallorca, Balearic Islands, Spain.<br />
BACKGROUND: The benefits of the Mediterranean diet for protecting against many diseases are usually attributed to high consumption of certain foods, characterized by the presence of bioactive substances such as polyphenols. Inflammation plays an important role in the pathogenesis of numerous diseases such as arthritis, allergies or neurodegenerative disorders. Dietary polyphenols constitute a large family of bioactive substances with potential beneficial effects against a broad group of diseases. Citrus fruits and juices are a rich source of vitamin C and flavonoids, with a potential effect on the inflammatory response. OBJECTIVE: The aim was to evidence the potential anti-inflammatory effects of the flavonoids hesperidin for its possible therapeutic application against diverse pathologies. METHOD: In the present review, available literature about the anti-inflammatory effects of hesperidin is reported and discussed. Moreover, we also discuss the chemistry, bioavailability and proposed mechanisms of action of hesperidin. RESULTS: Hesperidin is a flavonoid present in high concentration in citrus species and has numerous biological properties, principally antioxidant and anti-inflammatory. Several studies have been performed in order to evaluate the effects of hesperidin as anti-inflammatory agent using cellular and animal models and few clinical trials. Hesperidin treatment decreased inflammatory mediators and exerted significant antioxidant effects. The molecular basis for its anti-inflammatory effects seems to be mediated by signalling pathways especially the nuclear factor &kappa;&beta; pathway. CONCLUSION: Although hesperidin evidenced anti-inflammatory effects, the specific mechanism of action is not completely known and additional studies are required for elucidation of the molecular targets.<br />
DOI: 10.2174/0929867324666170718104412 PMID: 28721824 [Indexed for MEDLINE]<br />
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[2]. Molecules. 2019 Feb 12;24(3):648. doi: 10.3390/molecules24030648.<br />
Hesperidin as a Neuroprotective Agent: A Review of Animal and Clinical Evidence.<br />
Hajialyani M(1), Hosein Farzaei M(2)(3), Echeverr&iacute;a J(4), Nabavi SM(5), Uriarte E(6)(7), Sobarzo-S&aacute;nchez E(8)(9).<br />
Author information: (1)Pharmaceutical Sciences Research Center, Kermanshah University of Medical Sciences, Kermanshah 6718874414, Iran. [email protected]. (2)Pharmaceutical Sciences Research Center, Kermanshah University of Medical Sciences, Kermanshah 6718874414, Iran. [email protected]. (3)Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah 6718874414, Iran. [email protected]. (4)Facultad de Qu&iacute;mica y Biolog&iacute;a, Universidad de Santiago de Chile, Casilla 40, Correo 33, Santiago 9170022, Chile. [email protected]. (5)Applied Biotechnology Research Center, Baqiyatallah University of Medical Sciences, Tehran 1435916471, Iran. [email protected]. (6)Departamento de Qu&iacute;mica Org&aacute;nica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain. [email protected]. (7)Instituto de Ciencias Qu&iacute;micas Aplicadas, Universidad Aut&oacute;noma de Chile, Santiago 7500912, Chile. [email protected]. (8)Laboratory of Pharmaceutical Chemistry, Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela Santiago de Compostela, 15782 Santiago de Compostela, Spain. [email protected]. (9)Instituto de Investigaci&oacute;n e Innovaci&oacute;n en Salud, Facultad de Ciencias de la Salud, Universidad Central de Chile, Santiago 8330507, Chile. [email protected].<br />
Neuroprotection is the preservation of function and networks of neural tissues from damages caused by various agents, as well as neurodegenerative diseases such as Parkinson&#39;s, Alzheimer&#39;s, Huntington&#39;s diseases, and multiple sclerosis. Hesperidin, a flavanone glycoside, is a natural phenolic compound with a wide range of biological effects. Mounting evidence has demonstrated that hesperidin possesses inhibitory effect against development of neurodegenerative diseases. Our review discusses neuropharmacological mechanisms for preventive and therapeutic effects of hesperidin in neurodegenerative diseases. In addition, the review examines clinical evidence confirming its neuroprotective function. Various cellular and animal models specific to neurodegenerative diseases have been conducted to evaluate the underlying neuropharmacological mechanisms of hesperidin. Neuroprotective potential of this flavonoid is mediated by improvement of neural growth factors and endogenous antioxidant defense functions, diminishing neuro-inflammatory and apoptotic pathways. Despite the various preclinical studies on the role of hesperidin in the neurodegenerative diseases, less is known about its definite effect on humans. A limited number of clinical trials showed that hesperidin-enriched dietary supplements can significantly improve cerebral blood flow, cognition, and memory performance. Further clinical trials are also required for confirming neuroprotective efficacy of this natural flavonoid and evaluating its safety profile.<br />
DOI: 10.3390/molecules24030648 PMCID: PMC6384806 PMID: 30759833 [Indexed for MEDLINE]<br />
[3]. Crit Rev Food Sci Nutr. 2017 Feb 11;57(3):613-631. doi: 10.1080/10408398.2014.906382.<br />
Health-promoting effects of the citrus flavanone hesperidin.<br />
Li C(1), Schluesener H(1).<br />
Author information: (1)a Division of Immunopathology of the Nervous System , Department of Neuropathology , Institute of Pathology and Neuropathology, University of Tuebingen , Tuebingen , Germany.<br />
Hesperidin, a member of the flavanone group of flavonoids, can be isolated in large amounts from the rinds of some citrus species. Considering the wide range of pharmacological activities and widespread application of hesperidin, this paper reviews preclinical and clinical trials of hesperidin and its related compounds, including their occurrence, pharmacokinetics, and some marketed products available. Preclinical studies and clinical trials demonstrated therapeutical effects of hesperidin and its aglycone hesperetin in various diseases, such as neurological disorders, psychiatric disorders, and cardiovascular diseases and others, due to its anti-inflammatory, antioxidant, lipid-lowering, and insulin-sensitizing properties.<br />
DOI: 10.1080/10408398.2014.906382 PMID: 25675136 [Indexed for MEDLINE]<br />
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[4]. Exp Biol Med (Maywood). 2020 Mar;245(5):486-497. doi: 10.1177/1535370220903671. Epub 2020 Feb 12.<br />
Molecular mechanisms of action of hesperidin in cancer: Recent trends and advancements.<br />
Aggarwal V(1), Tuli HS(2), Thakral F(2), Singhal P(2), Aggarwal D(2), Srivastava S(3), Pandey A(3), Sak K(4), Varol M(5), Khan MA(6), Sethi G(7).<br />
Author information: (1)Department of Histopathology, Post Graduate Institute of Medical Education and Research (PGIMER), Chandigarh 160012, India. (2)Department of Biotechnology, Maharishi Markandeshwar (Deemed to be University), Ambala 133207, India. (3)Department of Biotechnology, MNNIT Allahabad, Prayagraj 211004, India. (4)Praeventio, NGO, Tartu 50407, Estonia. (5)Department of Molecular Biology and Genetics, Faculty of Science, Mugla Sitki Kocman University, Mugla TR48000, Turkey. (6)The Research Center for Preclinical Medicine,&nbsp;Southwest Medical University, Luzhou 646000,&nbsp;China. (7)Department of Pharmacology, Yong Loo Lin School of Medicine, National University of Singapore, Singapore 117600, Singapore.<br />
Hesperidin belongs to flavanones class of flavonoids and is known to possess broad-spectrum applicability to prevent dreadful diseases such as cardiovascular disease, neurodegeneration, and cancer. The reported anticancer effects of hesperidin have been found to be associated with its anti-oxidant and anti-inflammatory activities. Hesperidin interacts with numerous recognized cellular targets and inhibits cancer cell proliferation by inducing apoptosis and cell cycle arrest. In addition, evidence has suggested its promising role in inhibiting tumor cell metastasis, angiogenesis, and chemoresistance. The present mini-review highlights the ongoing development to identify hesperidin targets in cancer. Furthermore, the potential of nano technology-based hesperidin combinations and delivery systems will also be discussed. Overall, this review highlights all the possible molecular targets affected by hesperidin in tumor cells on a single platform. IMPACT STATEMENT: Experimental findings from numerous studies have demonstrated the anticancer effects of hesperidin (Hesp) to be associated with anti-oxidant and anti-inflammatory activities along with its potential role in inhibiting the tumor cell metastasis and angiogenesis. Additionally, Hesp can also reverse drug resistance of cancer cells, which make it a promising candidate to be used in combination with existing anti-cancer drugs. This review will be helpful for upcoming researchers and scientific community&nbsp;to find out complete capsular package about cancer drug targets of Hesp and its role in modulating various important hallmarks of cancer.<br />
DOI: 10.1177/1535370220903671 PMCID: PMC7082885 PMID: 32050794 [Indexed for MEDLINE]<br />
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[5]. Recent Pat Food Nutr Agric. 2014;6(1):60-3. doi: 10.2174/2212798406666140825120623.<br />
Hesperidin potentiates ghrelin signaling.<br />
Suzuki H, Asakawa A, Kawamura N, Yagi T, Inui A(1).<br />
Author information: (1)Department of Psychosomatic Internal Medicine, Kagoshima University Graduate School of Medical and Dental Sciences, 8-35-1 Sakuragaoka, Kagoshima, 890-8520, Japan.. [email protected].<br />
Hesperidin, a flavanone glycoside consisting of the flavone hesperitin bound to the disaccharide rutinose, is found in highly nutritious foods, such as oranges, tangelos, tangerines, grapefruits, and other citrus fruits. Exogenous hesperidin has been shown to influence a wide variety of biological functions, including induction of apoptosis and suppression of proliferation in human cancer cells; inhibition of tumor development in various tissues; and expression of antibacterial, antiviral, and antifungal activities. Previous in vivo studies have revealed that hesperidin may play a role in ghrelin secretion from the stomach through antagonism of the serotonin receptors. Because ghrelin appears to be involved in the pathophysiological mechanisms of several human disorders, hesperidin could be a promising target for the treatment of various diseases. This review addresses studies focused on the orexigenic and prokinetic activities of hesperidin in the context of ghrelin secretion. This article also presents some promising patents of hesperidin.<br />
DOI: 10.2174/2212798406666140825120623 PMID: 25176345 [Indexed for MEDLINE]

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