Catechin

Both catechins and theaflavins have been shown to have various health benefits, which include antiviral, antioxidative, antimutagenic, anticarcinogenic, and antiobesity activities.

From: Polyphenols in Human Health and Disease, 2014

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Cianidanol

J.K. Aronson MA, DPhil, MBChB, FRCP, HonFBPhS, HonFFPM, in Meyler's Side Effects of Drugs, 2016

General information

Cianidanol is an antioxidant flavonoid that occurs especially in woody plants. It is one constituent of green tea. It has immunomodulatory properties, including effects on T lymphocytes and killer cells [1].

Of 40 patients with chronic active hepatitis, 22 took cianidanol 3 g/day and 18 took placebo [2]. Adverse reactions to cianidanol were fever (n = 4), hemolysis (n = 1), and urticaria (n = 1).

Serious adverse reactions were not observed when cianidanol was used to treat HBe-antigen-positive chronic hepatitis in 338 patients [3]. The only adverse reaction of note that appeared to be drug-related was transient pyrexia in 13, necessitating withdrawal of therapy in eight. Four patients also had a skin eruption.

Cianidanol

In Meyler's Side Effects of Drugs (Sixteenth Edition), 2016

General information

Cianidanol is an antioxidant flavonoid that occurs especially in woody plants. It is one constituent of green tea. It has immunomodulatory properties, including effects on T lymphocytes and killer cells [1].

Of 40 patients with chronic active hepatitis, 22 took cianidanol 3 g/day and 18 took placebo [2]. Adverse reactions to cianidanol were fever (n = 4), hemolysis (n = 1), and urticaria (n = 1).

Serious adverse reactions were not observed when cianidanol was used to treat HBe-antigen-positive chronic hepatitis in 338 patients [3]. The only adverse reaction of note that appeared to be drug-related was transient pyrexia in 13, necessitating withdrawal of therapy in eight. Four patients also had a skin eruption.

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Role of Catechins in Chemosensitization

Anand Swaroop Shukla, ... Anju Shrivastava, in Role of Nutraceuticals in Cancer Chemosensitization, 2018

Sources of Catechins

Catechins can be harvested from a variety of sources including many herbs, fruits, vegetables, beverages, algae, and confectionary items. But their contents and types vary considerably among various sources. The availability of diverse sources also varies around the globe, which is a major reason for the nonuniform intake in nutrition. High catechin content is reported to be present in fresh tea leaves, apricots, broad beans, black grapes, strawberries, wines, etc. Also, high concentrations of EC are reported to be found in apples, blackberries, broad beans, black grapes, cherries, chocolate, pears, and raspberries (Table 1) [6]. Geographic changes also alter the content and variety of catechins in each of its sources such as tea leaves and other sources from different sites that have varying contents of catechins [11].

Table 1. Major Sources of Catechins in Conventional and Nonconventional Foods

Source Total Amount of Catechins (mg/100 g) Abundant Type References
Fruits
Apple 10–43 EGCG [6,7]
Apricot 10–25 Epicatechins [6,7]
Cherry 5–22 EGCG [6,7]
Strawberry 2–50 Catechin [6,7]
Vegetables
Beans 35–55 [6,7]
Lemon EGCG [6,8]
Beverages
Black tea 6–50 EGCG [6,7]
Green tea 10–80 EGCG [6,7]
Cider 4 Catechin
Red wine 8–30 Catechin [6,9]
Algae
Green algae (Acetabularia ryukyuensis) 33.3, 500 ± 320 Catechin, epicatechin [10]
Eisenia bicyclis 38.6 Catechin gallate, epicatechin [10]
Red algae (Chondrococcus hornemannii) 217 ± 95, 1600 ± 76 Catechin, epigallocatechin [10]
Other food products
Chocolate 46–61 [6,7]

As green tea is the most common aromatic beverage around the globe, many epidemiological studies correlated the tea consumption and decreased risk of various metabolic disorders as well as mortality in a dose-dependent fashion. Eighty percent of all polyphenols present in green tea are contributed by catechins. Mainly, EGCG, EGC, ECG, and EC are found in green tea. EGCG is the most abundant and the most pharmacologically potent catechin found in green tea [12].

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Polyphenols in Chronic Diseases and their Mechanisms of Action

Anand A. Zanwar, ... Subhash L. Bodhankar, in Polyphenols in Human Health and Disease, 2014

Catechin is present in many dietary products, plants, fruits (such as apples, blueberries, gooseberries, grape seeds, kiwi, strawberries), green tea, red wine, beer, cacao liquor, chocolate, cocoa, etc. Tea and red wine are some of the most popular beverages in the world. The antioxidant action of catechin is well-established by various in vitro, in vivo and physical methods. Catechin affects the molecular mechanisms involved in angiogenesis, extracellular matrix degradation, the regulation of cell death, and multidrug resistance in cancers and related disorders. A positive correlation between green tea consumption and cardiovascular health due to several actions such as antioxidative, antihypertensive, anti-inflammatory, antiproliferative, antithrombogenic, and anti-hyperlipidemic etc., is well established based upon epidemiological and experimental studies. Clinical studies have shown the beneficial effects of catechin due its antioxidant action.

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Green Tea Effects on Age-Related Neurodegeneration

José Paulo Andrade MD, PhD, Marco Assunção MD, PhD, in Diet and Nutrition in Dementia and Cognitive Decline, 2015

Summary Points

Catechins of the green tea are substances with pleiotropic effects that exert neuroprotective effects by multiple mechanisms at the molecular level, influence of several intracellular signaling pathways, and modulation of gene expression and protein functioning.

Catechins are able to cross the blood–brain barrier, reach the CNS, and regulate gene and protein expression in neurons.

The effects of catechins are determined at the molecular level in the limbic system through the increase of BDNF levels.

Catechins are potential therapeutical tools that can counterbalance neurodegenerative events associated with aging and related diseases.

There are several clinical trials evaluating the beneficial effects of catechins in the treatment or recovery of cognitive function in several neurodegenerative diseases related to aging.

The advice to consume green tea moderately may contribute to improving the quality of life in the elderly.

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Caenorhabditis elegans: an elegant model organism for evaluating the neuroprotective and neurotherapeutic potential of nutraceuticals

Altaf S. Darvesh, ... Vanessa A. Fitsanakis, in Nutraceuticals (Second Edition), 2021

Catechins

Catechins, phytochemicals found in especially high concentrations in teas and cocoa (Lee et al., 2003), are known to provide protection to C. elegans from oxidative and thermal stressors, particularly when used as a pretreatment (Zheng et al., 2009; González-Manzano et al., 2012). Work by Sucro-Laos et al. (2012) also showed that pretreatment with catechins increased survival when oxidative stress was induced by juglone (79% in controls vs 89%–98% in pretreated) when assayed on the first day of adulthood. This increase persisted for up to 6 days post-juglone exposure (56% in controls vs 84%–99% in pretreated), suggesting potential long-term changes in the oxidative stress response. Furthermore, catechin pretreatment protection extends to other forms of stress as well. Worms exposed to thermal stress following being pretreated with catechins had a survivability rate of 87%–99%, compared to only 83% in the control worms (Sucro-Laos et al., 2012). The protection also appeared to be chemical-specific and age-specific. This was borne out in studies showing that methylated catechins may have a greater protective effect in older worms compared to younger ones.

Along these lines, Abbas and Wink (2009) demonstrated that galloate moieties contributed to the stress-resistant properties of catechins in C. elegans. If life span, and not survival, was used as an endpoint, only the methylated catechins were effective, but marginally (6%–12%, compared to controls). These studies also demonstrate that C. elegans can be used to inform structure–function studies when moving to more complex model organisms.

Saul et al. (2009) provided evidence that catechin treatment (200 μM) resulted in a significantly enhanced life span, adding approximately 10 days to their normal life span of around 21 days. These data were followed up with oxidative stress tests using hydrogen peroxide to assess survival rate independent of longevity. As before, worms treated with catechin showed a dose-dependent protective response to the stress, with increasing survival rates of 9%, 15%, and 28% (100 μM, 200 μM, and 300 μM, respectively). When worms were co-exposed to catechins, rather than being pretreated, protection was no longer afforded. Rather, co-administration resulted in shorter body length and increased pharyngeal pumping rates compared to control worms grown in standard media (Saul et al., 2009).

It has been suggested that the disposable soma hypothesis (Saul, et al., 2009) may help explain the positive effects of catechins. This hypothesis states that energy normally devoted to increasing body length is diverted to maintenance. This leads to an increased life span, but shorter body length, which is often observed following catechin exposure. This was tested (Saul et al., 2009) using various short-lived mutants (age-1, daf-16, jnk-1, osr-1, sek-1, sir-2.1, unc-43, akt-2, daf-2, abnormal methyl viologen sensivity-1 (mev-1), and nhr-8; see Table 28.3). This study design also helped rule out the possibility that catechins were acting as direct antioxidants capable of detoxicating or inhibiting the production of reactive oxygen species (ROS).

These studies were confirmed using mev-1 mutant strains (Saul, et al., 2009). mev-1 is a succinate dehydrogenase cytochrome b560 subunit ortholog that plays a fundamental role in mitochondrial oxidative phosphorylation. Generally, mev-1 mutants show decreased energy metabolism coupled with an increase in vulnerability to oxidative stress (Ishii et al., 1990, 1998). Concomitant with abnormal energy production, this mutant strain also displays a shorter life span comparted to control worms. Since treatment with catechins was unable to rescue the shortened life span in these worms, the data suggest that catechins must exert their protective effect via other, non-mev-1-related pathways (Saul et al., 2009). Rather, it is likely that the observed life-prolonging effects of catechin are more dependent on the IIS pathway (Fig. 28.3), particularly through DAF-2 and AKT-2, to mediate stress resistance and cellular repair (Zarse et al., 2012).

Figure 28.3. Putative nutraceutical intervention in the insulin/IGF-1 signaling pathway.

Nutraceutical compounds may interact at various locations along the insulin/IGF-1 signaling pathway resulting in the promotion or inhibition of the ability of transcriptions factors (predominantly DAF-16) to translocate to the nucleus. Abbrevations: DAF, Abnormal dauer formation; DBL, Drosophila decapentaplegic (Dpp)/vertebrate bone morphogenetic proteins (BMPs)-like; LIN, Abnormal cell lineage;LON, Long body size (phenotype); MAB, Male abnormal (phenotype); SMA, Small body size (phenotype); SMAD, Caenorhabditis elegans; UNC, Uncoordinated.
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Biophenols

Syed Haris Omar, in Discovery and Development of Neuroprotective Agents from Natural Products, 2018

6.3 Catechins (Catechin, Epicatechin, and Epigallocatechin-3-Gallate)

Catechin, a flavonoid biophenol abundant in tea and coffee, showed in vitro inhibition of amyloid fibril (Aβ40 and Aβ42; IC50: 2.9 μM and 5.3 μM, respectively) formation (Ono et al., 2003, pp. 172–181). The in vitro inhibitory activity was also supported by another study in which catechin (extracted from Gingko biloba leaves) was found to inhibit Aβ42 aggregation (IC50: 14.93 μM) (Xie et al., 2014, pp. 5119–5134). Grape seed polyphenol extract (GSPE) containing catechin protected from tau pathology by interfering with the assembly of tau peptides into neurotoxic aggregates in the mouse brain (Wang et al., 2010, pp. 653–661). Moreover, the interference of catechin with tau-mediated neurodegenerative mechanisms caused amelioration of the neurodegenerative phenotype in the animal model of tauopathy (JNPL3 mice) expressing a human tau protein containing the P301L mutation (Santa-Maria et al., 2012, pp. 2072–2081). In a long-term (26 weeks) animal study, administration of green tea catechins (5 g/L) showed less memory impairment following intra-cerebroventricular injection of Aβ40 compared with the control (Haque et al., 2008, pp. 619–626). In support of catechin’s role in cognition enhancement, an animal study showed that catechin from green tea biophenols attenuates spatial memory impairments, antagonizes the neurotoxicity, and reduces tau hyperphosphorylation (Li et al., 2014, pp. 337–342). Catechin does not inhibit AChE significantly as evidenced from an in vitro study in which catechin from the leaves of Canarium patentinervium showed poor AChE enzyme inhibition with an IC50 value greater than 100 μg/mL (Mogana et al., 2014, p. 903,529). Among the group of catechins including epicatechin-3-gallate, epigallocatechin, epicatechin, and epigallocatechin-3-gallate (EGCG), EGCG has received much more attention than the other catechins due to its abundance and potent antioxidant activity (Mak, 2012, pp. 265–273). In vitro inhibition of amyloid fibril (Aβ40 and Aβ42; IC50: 2.8 μM and 5.6 μM, respectively) formation was shown by epicatechin, which is almost the same as catechin (Ono et al., 2003, pp. 172–181). Studies have showed that extracts containing the mixture of catechins (catechin and epicatechin) could be more effective than the individual catechin against AD (Fig. 4.8). In a long-term (9 months) study, 2% grape seed extracts containing catechin and epicatechin showed significant reduction in amyloid plaques by 49% in AD (APPSwe/PS1dE9) transgenic mice (Wang et al., 2009, pp. 3–14). In a short-term (21 days) animal study, administration of orally delivered epicatechin (3 mg/mL) reduced Aβ pathology in the cortex of an aged transgenic model of AD and suggested the indirect mode of action through noncatalytic β-secretase (BACE1) enzyme inhibition (Cox et al., 2015, pp. 178–187). A few in vitro studies have showed that epicatechin does not favor the inhibition of tau peptide (Taniguchi et al., 2005, pp. 7614–7623; Masuda et al., 2006, pp. 6085–6094), whereas the oxidized form of epicatechin is able to inhibit the tau aggregation and the activity is due to its interaction with the two cysteine residues in tau (George et al., 2013, pp. 21–40). Epicatechin (500 μg/g) increases memory function followed by hippocampal angiogenesis and neuronal spine density in mice (van Praag et al., 2007, pp. 5869–5878). An in vitro study showed that EGCG (Fig. 4.8) inhibited Aβ40 and tau protein (IC50: 3.0 μM; 1.8 μM, respectively) (Taniguchi et al., 2005, pp. 7614–7623). Further studies confirm amyloid (Aβ42) inhibition by EGCG (15 μM) and suggest that their action could be through altering amyloid morphology (Bieschke et al., 2010, pp. 7710–7715). EGCG interferes with a very early step in the amyloid formation pathway and suppresses the assembly of on-pathway amyloidogenic oligomers and protofibril, suggesting that it might induce intermolecular interactions between amyloid monomers that are stabilized by hydrogen bonds involving the hydroxyl group (Ehrnhoefer et al., 2008, pp. 558–566). A number of in vitro and in vivo studies have shown that an aqueous extract of Cinnamomum zeylanicum containing EGCG (0.11 mg/mL) and green tea EGCG (20–50 mg/kg) inhibited tau aggregation and pathology and provided cognition benefits in transgenic mice (Rezai-Zadeh et al., 2008, pp. 177–187; Peterson et al., 2009, pp. 585–597; Wobst et al., 2015, pp. 77–83). Interestingly, EGCG was then found to be the most potent AChE enzyme inhibitor with an IC50 of 0.0096 μM/mL (Okello et al., 2012, pp. 651–661). Further clinical studies required to confirm the anti-AD activity of catechins in human.

Figure 4.8. Chemical structure of catechin, epicatechin and epigallocatechin gallate.

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Multitarget approach for natural products in inflammation

Shintu Jude, Sreeraj Gopi, in Inflammation and Natural Products, 2021

4.5.7 Catechin and derivatives

Catechin and its derivatives form a major team of active polyphenolic components from plants. There are many compounds come under the category, such as catechin, epicatechin (EC), epigallocatechin (EGC), and epigallocatechin gallate (EGCG). Catechin exerts its pharmacological effects by reducing IL-5 and IL-13 levels and suppressing the NF-κB signal pathway [96]. Besides a pretreatment of catechin significantly ameliorated the activation of NF-κB and the expressions of COX-2, TNF-α, and IL-6 in benzo(a)pyrene-induced cells [97]. The mRNA expression levels of TLR4/NFκB-dependent inflammatory genes were lowered with the treatment with catechin [98]. EGCG was proved to target the COX, LO, IKK, AP-1, and NF-κB, during the antiinflammatory action. In addition, EGCG regulates MMP-2, COX-2, IL-6, TNF-α, and chemokines [99, 100]. Interestingly, EGCG could inhibit the action of TGF-β-activated MAP kinase (TAK1) and thus abrogate the production of IL-6 and IL-8 [100]. In a comparison, EGCG was the more effective inhibitor of IL-6 and IL-8, than EGC and EC. EGC and EGCG were effective in the downregulation of IL-1β-induced MMP-2 activity. Specific inhibition of COX-2 was observed with both EGC and EGCG. Together, these polyphenolic compounds exert synergic therapeutic benefits. Product rich in these polyphenols, such as green tea, is identified to have better beneficial effects [100].

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Natural products with antiinflammatory activities against autoimmune myocarditis

Akhila Nair, Sreeraj Gopi, in Inflammation and Natural Products, 2021

3.5.7 Catechins

Catechins are polyphenolic phytochemicals found in green tea and cocoa fruits. Other constituents found in green tea and cocoa fruits were (−)-epicatechin, (+)-gallocatechin, (+)-catechin, (+)-catechin, (−)-epigallocatechin, flavan-3-ols. Catechins are noted for their diverse biological activities such as antiobesity, antioxidative, antiinflammatory, antiatherosclerosis, antihyperglycemia, and antihypercholesterolemia. Suzuki et al. reported that catechin improves cardiac function in experimental autoimmune rats. The study showcased significant improvement in fibrosis and reduced myocardial cell infiltration. Further, it was observed through immunohistochemistry that messenger ribonucleic acid (mRNA) of tumor necrosis factor-alpha (TNF-α) were reduced and Th 2 cytokines were increased as well as nuclear factor kappa B (NF-κB) and ICAM-1 were reduced when compared with the group kept as control [40]. Similarly the study reported by Zempo et al. supported that cocoa polyphenol efficiently reduced the fibrotic area ratio and cardiac infiltration and increase in heart weight to body weight (HW/BW) (symbolizes myocardial hypertrophy) in experimental autoimmune myocarditis rats. Moreover, reduced cardiac H2O2concentration, cardiac myeloperoxidase (MPO), dihydroethidium staining (DHE) intensity, NF-κB P65 phosphorylation. Collagen type 1, vascular adhesion molecule (VCAM-1) and mRNA expression of IL-6, IL-1, E-selection as observed through reverse transcriptase-PCR [41]. To summarize, catechins play important role in inflammatory autoimmune myocarditis [8].

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Natural product–based nanomedicine: polymeric nanoparticles as delivery cargoes of food bioactives and nutraceuticals for anticancer purposes

Francine Carla Cadoná, ... Aline Ferreira Ourique, in Advances and Avenues in the Development of Novel Carriers for Bioactives and Biological Agents, 2020

2.3.2 Catechins

Catechins are present in a wide variety of plant products such as green tea, cacao, grape, grape juices, and wine. Catechins are polyphenolic compounds, such as epigallocatechin-3-gallate (EGCG), epigallocatechin, epicatechin-3-gallate and epicatechin, gallocatechins, and gallocatechin gallate. Catechins intake can reduce inflammatory events and platelet aggregation, and avoid cardiovascular dysfunctions, such as atherosclerosis, hypertension, endothelial dysfunction, cardiac ischemic diseases, cardiomyopathy, and cardiac hypertrophy (Khan and Mukhtar, 2018). Moreover, many studies have reported that catechins can present antitumor effect and increase chemotherapy response (Saiko et al., 2015; Mayr et al., 2015).

Saiko et al. (2015) described the antitumor action of EGCG by proapoptotic action in human cells of acute promyelocytic leukemia (HL-60). The results indicated that EGCG presented anticarcinogenic effect in HL-60 cells by inhibiting DNA synthesis, cell proliferation, increasing apoptosis, and arresting cell cycle. Also, Mayr et al. (2015) reported the synergism of catechin and cisplatin against biliary tract cancer. Different types of cell lines for this type of cancer were treated with EGCG alone and in combination with cisplatin. In addition, synergism increased apoptosis and cell cycle arrest. This association caused cell cycle arrest, decreased cell viability by increased apoptosis, and improved the chemotherapy response of biliary tract cancer treatment.

In addition, another investigation performed by Bimonte et al. (2015) indicated that catechin in combination with chemotherapeutic bleomycin generated an efficient antitumor synergism by inhibiting cell pancreatic cancer growth cell line (MiaPaCa-2). The combination of catechin and bleomycin was able to decrease cell proliferation by blocking S-phase of cell cycle and plasma membrane depolarization and activating apoptosis and DNA damage.

Saeed et al. (2015) reported that pretreatment with this molecule is able to attenuate the cardiotoxicity generated by doxorubicin in rats. Furthermore, EGCG is able to protect against neurotoxicity generated by cisplatin by inhibiting apoptosis in mice (Zou et al., 2014).

In addition, the potentiating synergistic effect of EGCG associated with doxorubicin was found in hepatocellular carcinoma cells (Hep3B), due to the increase in autophagy vesicles within tumor cells and, consequently, cell death increased (Chen et al., 2014).

Also, the antitumor action of EGCG was described by Shimizu et al. (2015). The results showed that this active molecule was able to inhibit cell growth and proliferation in human hepatocarcinoma cells by inducting apoptosis and inhibiting some molecules involved in cell proliferation and survival, such as AKT and extracellular signal-regulated kinase (ERK). Zhang et al. (2015) also found the same antitumor effect in hepatocellular carcinoma (LM6) cells and demonstrated that EGCG did not affect healthy liver cells.

Moreover, the antitumor effect of EGCG was also found in osteosarcoma (MG63 and U2OS) cell lines (Jiang et al., 2014), lung cancer (A549) (Sonoda et al., 2014; Ma et al., 2014), ovarian carcinoma (OVCAR-3) (Wang et al., 2014), and colorectal (HCT116) (Moseley et al., 2013).

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