Cocoa Extract

Cocoa Extract is a bitter chocolate-tasting mixture that is comprised of xanthine molecules (theobromine and Caffeine) and an assortment of procyanidins. This extract appears to hold cardiovascular and cognitive benefit associated with improving blood flow.

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Also Known As

Chocolate polyphenols, Cocoa polyphenols, Cacao polyphenols, Cacao extract, Chocamine


Do Not Confuse With

Chocolate (The extract paired with macronutrients)


Things to Note

  • Cocoa polyphenols may be slightly stimulatory due to a small Caffeine content

Studies assessing the influence of cocoa extract on blood flow note that 5-26g of dark cocoa contains 65-1,095mg of flavanols, and that within this range there are dose-dependent benefits to blood flow. This may be related to the recommended intake of cocoa flavanols (not so much cocoa 'extract', but the flavanols in particular) being in the range of 500-1000mg daily taken with meals.

It is unsure if this is the optimal dose, but it appears to be more effective than lower doses.


This does not mean you should be pigging out on chocolate. Note the recommended dosage (especially the amount of dark chocolate that will satisfy for a reasonable dose).


Sol Orwell

Table of Contents:


Edit1. Sources and Composition

1.1. Sources

Cocoa extract (also referred to as Cocoa polyphenolics) are derived from Cacao seeds as a bitter bulk ingredient for commercial usage and supplementation.[1]

1.2. Composition

Cocoa extract contains polyphenolics[2] ranging from 8.07 to 484.7mg/g (defatted cocoa powder)[3], which places it as one of the better dietary sources (alongside select herbs used as Spice, dark colored berries, and select vegetables)[4][2][5] being reported to sometimes contain up to 10% flavonoids.[6] Cocoa specifically contains (noncaloric cocoa powder unless otherwise specified):

  • (+)-catechin at 107.75mg/100g[4]
  • (-)-epicatechin at 158.30mg/100g[4]
  • Procyanidins B1 (112mg/g), B2 (71.57mg/g), and C1 (23.83mg/g)[4] (dimers and a trimer of epicatechin, respectively)
  • (-)-Epicatechin-(2a-7)(4a-8)-epicatechin 3-O-galactoside at 5mg/100g[4]
  • Cinnamtannin A2 at 33.17mg/100g[4] (catechin tetramer, currently thought to be exclusive to chocolate)[4]
  • Benzoic acid (0.06mg/100g)[4]
  • 3-Methylcatechol, 4-Methylcatechol, and 4-Ethylcatechol (all below 0.1mg/100g)[4] and catechol at 0.12mg/100g[4]
  • Quercetin (dark chocolate) at 25mg/100g[4]
  • Resveratrol (0.04mg/100g) and its 3,O-glucoside (0.1mg/100g) in dark chocolate[4]
  • Ferulic acid (dark chocolate) at 24mg/100g[4]
In regards to the polyphenolics, cocoa has a large amount of procyanidins (chains of catechin molecules) and a particularly high content of (-)-epicatechin relative to other catechin sources like green tea. Other phenolics such as resveratrol and quercetin seem to be lower than the catechin and procyanidin content and their relevance to cocoa powder is uncertain

Other components of cocoa extract include:

In regards to the low-weight psychoactives, cocoa has a low amount of trace amines (PEA and tyramine) and a low amount of xanthines such as caffeine

In general, cocoa is said to have around a 60/40 epicatechin:catechin ratio due to having higher levels of procyanidin B2 (epicatechin dimer) and procyanidin C1 (epicatechin trimer), with lower relative concentrations of procyanidin B1 (epicatechin-catechin) when compared to other procyanidin sources (Grape Seed Extract or Pycnogenol).[6] Natural cocoa products appear to have more total flavonoids than do other dark chocolate or cocoa products, with milk chocolate products having the least amount of flavonoids.[7]

1.3. Chocamine

A particular brand of cocoa extract is known as 'chocamine' patented by RFI ingredients, which according to their website[8] the product specifications state that the powder is standardized to theobromine (greater than 12% by weight), caffeine (less than 0.5%), polyphenolics (greater than 5%) and contains added tapioca starch and some other spices (Ginger, allspice, Cinnamon, and vanilla powder in undisclosed amounts).

Chocamine is a theobromine rich cocoa powder


Edit2. Pharmacology

2.1. Absorption

Cocoa flavanols appear to be stable in the stomach environment, with 50-60 minutes of gastrointestinal transit time not resulting in any modification of flavanol monomers nor procyanidins up to five monomers in length.[9]

2.2. Serum

Oral ingestion of drinks (with some additional macronutrients) containing cocoa was noted to increase serum epicatechin when measured at 120 hours post ingestion to approximately 500ng/mL (2g cocoa), 1,200ng/mL (5g), 3,500ng/mL (13g), and 8,000ng/mL (26g); data derived from graphs.[10]


Edit3. Neurology

3.1. Appetite

It appears that the scent of chocolate (preserved by aromatic compounds in chocamine) is enough to potentially reduce appetite.[11]

3.2. Blood Flow and Stroke

In otherwise healthy young adults subject to a cognitive task, it appears that five days supplementation of 172mg cocoa flavanols (final dose 90 minutes before testing) increases blood oxygenation level-dependent (BOLD) contrast indicating increased cerebral oxygenation specifically in the prefrontal cortex, anterior cingulate Cortex, and parietal cortex; this was not accompanied by altered reaction times.[12] This was accompanied by an increase in blood flow that peaked two hours after supplementation (40% increase) and returned to baseline within six hours.[12]

In otherwise healthy youth, cocoa flavanols appear to enhance blood flow to the brain and alongside the increase in blood flow there appears to be an increase in cerebral oxygenation

In a cohort of 37,103 men (Sweden) followed for 10.2 years found a decreased risk of stroke associated with chocolate with the highest quartile (25%) of consumption, with a median intake of 62.9g weekly, having an 0.83 relative risk compared to the no chocolate intake; the CI was 0.70-0.99.[13]

3.3. Mood State

In older adults (40-65yrs), supplementation of 500mg cocoa polyphenols for 30 days (but not 250mg) was associated with an improved mood state mainly around calmness and contentness; 250mg was ineffective.[14]

3.4. Cognition

One study conducted on elderly persons with mild cognitive decline noted that cocoa flavanols were able to improve cognitive performance in a relatively dose dependent manner at both 520mg and 990mg daily, as assessed by Trail making tests and Verbal Fluency.[15] Elsewhere, there has been a failure of 250-500mg cocoa polyphenols for 30 days at improving attention (speed, continuity, and power of attention).[14]

3.5. Memory and Learning

250-500mg of cocoa flavonols daily for 30 days in otherwise healthy older adults has failed to improve quality of working memory or secondary memory.[14]


Edit4. Cardiovascular Health

4.1. Mechanisms

Cocoa flavanols (procyanidins 2-10 monomers in length) may inhibit fat absorption, where the tested chocolate with the highest phenolic content (48.1%) inhibiting pancreatic lipase 25–53% at 20μM (more potency associated with longer chain procyanidins).[16] Phospholipase A2 was inhibited by 46–74% at 100μM.[16]

May have anti-lipid absorption properties

It is thought that cocoa increases blood flow via increasing Nitric Oxide synthesis, as the benefits of cocoa on blood flow are inhibited by blocking the eNOS enzyme[17][18] and ingestion of cocoa is associated with higher circulating biomarkers of nitric oxide metabolism.[19][17][20]

This is thought to be from enhanced synthesis of nitric oxide (rather than enhanced responsiveness to nitric oxide) as the vasodilating effects of nitric oxide donors are unaffected[10][21][22][23] and cocoa flavanols have been noted to induce activity of the eNOS enzyme in vitro associated with both procyanidins and isolated (-)-epicatechin,[24][25] with isolated (-)-epicatechin being most active at a concentration of 1μmol/L 20-40min after incubation[24] associated with increased phosphorylation of Ser-1177 and Ser-633 (dephosphorylation of Thr-495) secondary to calmodulin associated with eNOS due to PI3K activation.[24] Catechin appears to be 25% as potent as (-)-epicatechin, and a mixture of both is less potent than pure epicatechin.[24]

One study has also noted a reduction in vascular arginase activity,[26] the enzyme that degrades Arginine.

It is unsure if this is related to the antioxidant properties of cocoa (which are thought to be the mechanism by which agents like Grape Seed Extract or vitamn C aid nitric oxide), as at least one study has noted increased blood flow independent of changes in oxidation of LDL (biomarker of oxidation).[10]

In regards to blood flow and circulatory health, cocoa flavanols are thought to improve circulation secondary to causing production of nitric oxide. This is likely due to epicatechin or other catechins directly stimulating the nitric oxide synthase enzyme

4.2. Cardiovascular Disease Risk

In regards to epidemiological research, there appears to be an association between higher chocolate intake and lower morbidity/mortality and risk for cardiovascular disease, as well as a protective effect as assessed by some other biomarkers (such as blood pressure).[27][28][29][30]

4.3. Blood Pressure and Flow

One of the modes of cardiac protection that chocamine provides is via reduction of blood pressure via inhibition of Angiotension converting enzyme (ACE), establishing a role of chocamine as an ACE inhibitor[31] and possibly a mediator of Nitric oxide.[32][33] These cardiac effects are theorized to be due to the flavanol content of chocamine.

Acutely (a single dose of 2-26g cocoa extract), it has been noted that supplementation is associated with minor increases in blood pressure (2-3mmHg systolic and diastolic) without affecting heart rate; it was not deemed a concern due to an increase in blood flow noted.[10]

One meta-analysis of 20 studies[34] concluded that consumption of cocoa products (usually dark chocolate or cocoa supplementation) is associated with a 2-3mmHg reduction of blood pressure.

In interventions, cocoa flavanols at doses above 520mg can reduce blood pressure in elderly persons.[15]

Chronic ingestion of cocoa flavanols appears to be able to reduce blood pressure, affecting both systolic and diastolic but by a small amount (2-3mmHg)

Blood flow appears to be enhanced following ingestion of cocoa extract in otherwise healthy younger[21] and older persons,[10] diabetics,[23] smokers,[17][35] and those at risk for cardiovascular disease[36][20] although one study suggested that those already with coronary artery disease do not note benefit.[37] These studies tend to use supplementation of cocoa in the dosage range fo 13-26g.

In otherwise healthy older individuals given drinks containing various dosages of cocoa (2, 5, 13, and 26g or placebo) and measured over the next 120 minutes, it was found that 5-26g cocoa (65-1,095mg total flavanols) was able to increase blood flow as assessed by FMD in a dose-dependent and linear manner, which correlated with serum polyphenolics, namely (-)-epicatechin[10] which appears to be the isomer of the catechins which is active[38] by increasing nitric oxide synthase activity [24] Oral ingestion of isolated (-)-epicatechin appears to mimick the effects seen with cocoa polyphenols.[39]

Appears to promote circulation in a dose-dependent manner, which correlates very well with serum (-)-epicatechin. Cocoa polyphenolics may be epicatechin prodrugs in regards to improving blood flow

4.4. Lipoproteins and Triglycerides

In vitro, it appears that cocoa polyphenolics is able to inhibit LDL and vLDL oxidation[40][41] with similar or lesser potency to the Green Tea Catechins.[42] Despite this, single ingestion of cocoa flavanols up to 1,095mg (26g cocoa) does not appear to affect circulating LDL oxidation rates for up to 120 minutes after ingestion.[10]

May be able to reduce LDL oxidation rates, but does not yet have a large amount of in vivo evidence. Does not appear to be effective after a single dose like Olive leaf extract usually is

Polyphenolic compounds in chocamine can also reduce total LDL and Triglyceride levels[43] while reducing platlet reactivity.[44][45]

4.5. Interventions

Various human trials show promise with chocamine, either in supplemental form or administered in food form around 75g of dark chocolate, as effective in reducing various markers of heart disease.[32][46][47] Overall chocamine shows a modest but relatively consistent decrease in blood pressure around 5mm/Hg systolic, which correlates to a 20% reduced risk of a cardiovascular event over 5 years.[47][48]


Edit5. Skeletal Muscle and Physical Performance

5.1. Bioenergetics

Cocoa powder (72.4% polyphenols with a total 6.43% (-)-epicatechin content and 3.54% procyanidin B2 content) at 50mg/kg daily in mice for two weeks has been noted to reduce blood glucose thought to be secondary to an increase in fat oxidation in skeletal muscle;[49] an increase in resting energy expenditure (RER) was noted in mice fed the powder relative to control without influencing locomotor activity, associated with an increase in CPT2 and UCP1 expression in skeletal muscle as well as an increase in mitochondrial activity (as assessed by copy number).[49]


Edit6. Inflammation and Immunology

6.1. Virology

The structure of epicatechin, found in chocolate but is one of the main four Green Tea Catechins, has been found to normalize adverse changes (by the Tat protein; elevated in HIV) with proBDNF and BDNF, which exerted neuroprotective effects against the side-effects of HIV with greater potency than Resveratrol.[50]


Edit7. Interactions with Organ Systems

7.1. Intestines

A diet high in cocoa flavanols (494mg with 89mg epicatechin and 21mg catechin) daily for four weeks has been noted to increase the bacterial count of bifidobacterial, enterococcus, and lactobacilli strains in the intestines while decreasing clostridia as assessed by fecal examination.[51] This study also noted decreases in blood pressure and C-reactive protein, with the latter correlated to changes in lactobacilli,[51] and the suppression of clostridia histolyticum noted with cocoa flavanols has been noted with isolated (+)-catechin[52] and other Green Tea Catechins.[53]

References

  1. Crozier SJ, et al. Cacao seeds are a "Super Fruit": A comparative analysis of various fruit powders and products. Chem Cent J. (2011)
  2. Manach C, et al. Polyphenols: food sources and bioavailability. Am J Clin Nutr. (2004)
  3. Determination of Flavanol and Procyanidin (by Degree of Polymerization 1-10) Content of Chocolate, Cocoa Liquors, Powder(s), and Cocoa Flavanol Extracts by Normal Phase High-Performance Liquid Chromatography: Collaborative Study
  4. Phenol-Explorer: an online comprehensive database on polyphenol contents in foods
  5. Habauzit V, Morand C. Evidence for a protective effect of polyphenols-containing foods on cardiovascular health: an update for clinicians. Ther Adv Chronic Dis. (2012)
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  7. Ramirez-Sanchez I, et al. Fluorescent detection of (-)-epicatechin in microsamples from cacao seeds and cocoa products: Comparison with Folin-Ciocalteu method. J Food Compost Anal. (2010)
  8. Chocamine
  9. Rios LY, et al. Cocoa procyanidins are stable during gastric transit in humans. Am J Clin Nutr. (2002)
  10. Monahan KD, et al. Dose-dependent increases in flow-mediated dilation following acute cocoa ingestion in healthy older adults. J Appl Physiol. (2011)
  11. Massolt ET, et al. Appetite suppression through smelling of dark chocolate correlates with changes in ghrelin in young women. Regul Pept. (2010)
  12. Francis ST, et al. The effect of flavanol-rich cocoa on the fMRI response to a cognitive task in healthy young people. J Cardiovasc Pharmacol. (2006)
  13. Chocolate consumption and risk of stroke: A prospective cohort of men and meta-analysis
  14. Pase MP, et al. Cocoa polyphenols enhance positive mood states but not cognitive performance: a randomized, placebo-controlled trial. J Psychopharmacol. (2013)
  15. Desideri G, et al. Benefits in cognitive function, blood pressure, and insulin resistance through cocoa flavanol consumption in elderly subjects with mild cognitive impairment: the Cocoa, Cognition, and Aging (CoCoA) study. Hypertension. (2012)
  16. Gu Y, et al. Inhibition of key digestive enzymes by cocoa extracts and procyanidins. J Agric Food Chem. (2011)
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(Common misspellings for Cocoa Extract include chocmine, choamine, chocolamine)

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