Disease chemopreventive effects and molecular mechanisms of hydroxylated polymethoxyflavones

Lai, Ching-Shu; Wu, Jinn‐Chang; Ho, Chi‐Tang; Pan, Min‐Hsiung

doi:10.1002/biof.1236

Cited by 52 publications

(32 citation statements)

References 98 publications

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“…In addition to substituting the hydrogen atoms on A, B and C rings of flavone skeleton, the hydroxy groups may also replace the methoxy groups to form the hydroxylated PMFs. The major citrus hydroxylated PMFs identified thus far are 5-demethyl PMFs, commonly generated in aged citrus pericarp as well as citrus fruits undergoing prolonged storage, formed through autohydrolysis of their PMF counterparts (Lai et al, 2015). It is surprisingly to find out that 5-demethyl PMFs may possess superior inhibitory effect on inflammation-induced tumorigenesis than their parent polymethoxylated PMFs (Ma et al, 2014), probably resulting from the better permeability and membrane penetrating activity of the mono-or di-hydroxylated PMFs, leading to their better absorption rate and bioavailability (Wang, Li and Ho, 2018).…”

Section: Chemistry Of Citrus Peel Pmfsmentioning

confidence: 99%

Anti-inflammatory effects of polymethoxyflavones from citrus peels: a review

Wang¹,

Li²,

Wei³

et al. 2018

JFB

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Inflammation is a non-specific kind of biological immune response of body tissues to any type of external or internal injuries, such as pathogens, irritants and immune stress reactions. There are two types of inflammation, namely acute and chronic. Acute inflammation starts and develops rapidly, and is aroused by various factors, including injuries, infection, toxins or immune reactions. Chronic inflammation usually lasts for an extended long period of time and results from elimination failure of acute inflammation, autoimmune disorders, various pathogens and pathogenic environments. Except for the damage itself, there exists a direct and intimate connection between chronic inflammation and various clinic common diseases, such as neurodegeneration, as well as metabolic and cardiovascular ailments. Citrus peel is a by-product generated in citrus juice processing. Polymethoxyflavones (PMFs) exist abundantly and almost exclusively in citrus peels, and their biological activities have been broadly investigated in recent years. PMFs have proven to possess potential inhibitory bioactivities towards a number of functional and immune diseases including inflammation. The two most abundant PMFs exhibiting prominent bioactivities in citrus peels are nobiletin and tangeretin, ubiquitously detected in various citrus species. In this review, the beneficial health effects and the underlying molecular mechanisms of ten main citrus PMFs were illustrated against numerous inflammatory diseases, including inflammatory bowel disease (IBD), neuroinflammation and organ inflammation, among others.

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Section: Chemistry Of Citrus Peel Pmfsmentioning

confidence: 99%

Anti-inflammatory effects of polymethoxyflavones from citrus peels: a review

Wang¹,

Li²,

Wei³

et al. 2018

JFB

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“…Our studies have shown significant anti-inflammatory effects of flavonoid-enriched orange peel extracts as validated in cell-based and in vivo models for inflammation (Gosslau et al, 2014;Gosslau et al, 2011;Gosslau et al, 2018;Lai et al, 2015;Li et al, 2007;Sergeev et al, 2007;Wang et al, 2016). Chronic inflammation is also a key pathologic link between obesity and type 2 diabetes (T2D).…”

Section: Therapeutic Effects Of Citrus Fruit Polyphenolic Flavonoids mentioning

confidence: 76%

“…Since then, many more flavonoids were identified and characterized as bioactive compounds in peels and juice of citrus fruits (Gattuso et al, 2007;Meiyanto et al, 2012;Nair et al, 2018;Nogata et al, 2006;Putnik et al, 2017). In citrus fruits, polyhydroxylated flavonoids (PHFs) and polymethoxylated flavonoids (PMFs) are considered as major bioactives (Barreca et al, 2017;Lai et al, 2015;Li et al, 2009;Zhao et al, 2018). It is generally believed that antioxidant and anti-inflammatory activities are the main underlying mechanisms for the health-promoting effects of PHFs and PMFs.…”

Section: Therapeutic Effects Of Citrus Fruit Polyphenolic Flavonoids mentioning

confidence: 99%

“…They are categorized according to the saturation level of the central pyran ring and the existence of 3-OH group, mainly into flavones, flavanols, isoflavones, flavonols, flavanones, and flavanonols. Polyhydroxylated (PHFs) and polymethoxylated flavonoids (PMFs) are considered as major bioactives in citrus fruits (Barreca et al, 2017;Lai et al, 2015;Li et al, 2009;Zhao et al, 2018).…”

Section: Chemistry Of Polyhydroxyflavones (Phfs)mentioning

confidence: 99%

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The role of rutin and diosmin, two citrus polyhydroxyflavones in disease prevention and treatment

Gosslau¹,

Ho²,

Li³

2019

JFB

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Chronic inflammation and dysregulation of apoptotic pathways leading to free radical-induced tissue damage are widely recognized as major underlying causes of major degenerative diseases, including cancer, diabetes, neurological and cardiovascular disorders. Citrus fruits are rich sources of polyphenolic flavonoids well known for their wide range of pharmacological properties. Rutin (quercetin-3-O-rutinoside) and diosmin (diosmetin 7-Orutinoside) are two major polyhydroxyflavone glycosides abundantly found in citrus peels and, to a lesser extent, in pulp of a variety of different citrus species. During digestion, hydrolysis by intestinal enzymes and gut microbiota lead to the release of their corresponding bioactive aglycones (e.g., quercetin or diosmetin). Data obtained in cell-based, animal and clinical studies demonstrated strong preventive and/or therapeutic effects of rutin and its aglycone flavone quercetin. Although lesser studies available, our recent literature review suggests diosmin as promising citrus fruit polyhydroxyflavonoids, effective against various diseases associated with chronic inflammation.

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“…One side the hydroxyl groups of flavones have free radical scavenging activity, but extensive conjugation of free hydroxyl groups to flavones results in low oral bioavailability; hence, they undergo rapid sulfation and glucuronidation in the small intestine and liver by phase II enzymes. Consequently, conjugated metabolites, but not the original compounds, can be found in plasma [34]. However, if one or more hydroxyl groups are capped by methylation, the substitution of a methoxy group by the hydroxyl group induces an increase in metabolic stability and improves transport and absorption.…”

Section: Discussionmentioning

confidence: 99%

Identification of Bioactive Phytochemicals in Leaf Protein Concentrate of Jerusalem Artichoke (Helianthus tuberosus L.)

Kaszás

Alshaal

El-Ramady

et al. 2020

Plants

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Jerusalem artichoke (JA) is widely known to have inulin-rich tubers. However, its fresh aerial biomass produces significant levels of leaf protein and economic bioactive phytochemicals. We have characterized leaf protein concentrate (JAPC) isolated from green biomass of three Jerusalem artichoke clones, Alba, Fuseau, and Kalevala, and its nutritional value for the human diet or animal feeding. The JAPC yield varied from 28.6 to 31.2 g DM kg−1 green biomass with an average total protein content of 33.3% on a dry mass basis. The qualitative analysis of the phytochemical composition of JAPC was performed by ultra-high performance liquid chromatography-electrospray ionization-Orbitrap/mass spectrometry analysis (UHPLC-ESI-ORBITRAP-MS/MS). Fifty-three phytochemicals were successfully identified in JAPC. In addition to the phenolic acids (especially mono- and di-hydroxycinnamic acid esters of quinic acids) several medically important hydroxylated methoxyflavones, i.e., dimethoxy-tetrahydroxyflavone, dihydroxy-methoxyflavone, hymenoxin, and nevadensin, were detected in the JAPC for the first time. Liquiritigenin, an estrogenic-like flavanone, was measured in the JAPC as well as butein and kukulkanin B, as chalcones. The results also showed high contents of the essential amino acids and polyunsaturated fatty acids (PUFAs; 66-68%) in JAPC. Linolenic acid represented 39–43% of the total lipid content; moreover, the ratio between ω-6 and ω-3 fatty acids in the JAPC was ~0.6:1. Comparing the JA clones, no major differences in phytochemicals, fatty acid, or amino acid compositions were observed. This paper confirms the economic and nutritional value of JAPC as it is not only an alternative plant protein source but also as a good source of biological valuable phytochemicals.

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Disease chemopreventive effects and molecular mechanisms of hydroxylated polymethoxyflavones

Cited by 52 publications

References 98 publications

Anti-inflammatory effects of polymethoxyflavones from citrus peels: a review

Anti-inflammatory effects of polymethoxyflavones from citrus peels: a review

The role of rutin and diosmin, two citrus polyhydroxyflavones in disease prevention and treatment

Identification of Bioactive Phytochemicals in Leaf Protein Concentrate of Jerusalem Artichoke (Helianthus tuberosus L.)

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