Procyanidin

Procyanidins, including the lesser bioactive / bioavailable polymers (4 or more catechines), represent a group of condensed flavan-3-ols that can be found in many plants, most notably apples, maritime pine bark, cinnamon, aronia fruit, cocoa beans, grape seed, grape skin,{{cite journal |last1=Souquet |first1=J |title=Polymeric proanthocyanidins from grape skins |journal=Phytochemistry |volume=43 |pages=509–512 |year=1996 |doi=10.1016/0031-9422(96)00301-9 |last2=Cheynier |first2=Véronique |last3=Brossaud |first3=Franck |last4=Moutounet |first4=Michel |issue=2}} and red wines of Vitis vinifera (the common grape).{{cite journal | last1 = Yang | first1 = J | last2 = Xiao | first2 = YY | year = 2013 | title = Grape phytochemicals and associated health benefits | journal = Crit Rev Food Sci Nutr | volume = 53 | issue = 11| pages = 1202–1225 | doi = 10.1080/10408398.2012.692408 | pmid = 24007424 | s2cid = 19094002 }} However, bilberry, cranberry, black currant, green tea, black tea, and other plants also contain these flavonoids.USDA, August 2004. [http://www.ars.usda.gov/SP2UserFiles/Place/80400525/Data/PA/PA.pdf USDA Database for the Proanthocyanidin Content of Selected Foods]. PDF summary accessed from main USDA page [http://www.ars.usda.gov/Services/docs.htm?docid=5843 here]. Page accessed July 31, 2015 Procyanidins can also be isolated from Quercus petraea and Q. robur heartwood (wine barrel oaks).{{cite journal |last1=Vivas |first1=N |last2=Nonier |first2=M |last3=Pianet |first3=I |last4=Vivasdegaulejac |first4=N |last5=Fouquet |first5=E |title=Proanthocyanidins from Quercus petraea and Q. robur heartwood: quantification and structures |journal=Comptes Rendus Chimie |volume=9 |pages=120–126 |year=2006 |doi=10.1016/j.crci.2005.09.001|url=https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2005.09.001/ |url-access=subscription }} Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in numerous procyanidin oligomers.{{cite journal |journal = J Agric Food Chem |date=Jun 2008 | volume = 56 | issue = 12 | pages = 4631–4636 | title = Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.) |pmid = 18522407| doi = 10.1021/jf800161u |vauthors=Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST }}

Apples contain on average per serving about eight times the amount of procyanidin found in wine, with some of the highest amounts found in the Red Delicious and Granny Smith varieties.{{cite journal |first1=John F. |last1=Hammerstone |first2=Sheryl A. |last2=Lazarus |first3=Harold H. |last3=Schmitz |title=Procyanidin content and variation in some commonly consumed foods |volume=130 |issue=8S Suppl |pages=2086S–92S |journal=The Journal of Nutrition |date=August 2000 |pmid=10917927 |url=http://jn.nutrition.org/cgi/content/full/130/8/2086S |quote=Figure 5 |doi=10.1093/jn/130.8.2086S|doi-access=free }}

The seed testas of field beans (Vicia faba) contain procyanidins{{Cite journal | last1 = Merghem | first1 = R. | last2 = Jay | first2 = M. | last3 = Brun | first3 = N. | last4 = Voirin | first4 = B. | title = Qualitative analysis and HPLC isolation and identification of procyanidins fromvicia faba | doi = 10.1002/pca.731 | journal = Phytochemical Analysis | volume = 15 | issue = 2 | pages = 95–99 | year = 2004 | pmid = 15116939}} that affect the digestibility in piglets{{Cite journal | last1 = Van Der Poel | first1 = A. F. B. | last2 = Dellaert | first2 = L. M. W. | last3 = Van Norel | first3 = A. | last4 = Helsper | first4 = J. P. F. G. | title = The digestibility in piglets of faba bean (Vicia faba L.) as affected by breeding towards the absence of condensed tannins | doi = 10.1079/BJN19920134 | journal = British Journal of Nutrition | volume = 68 | issue = 3 | pages = 793–800 | year = 2007 | pmid = 1493141| doi-access = free }} and could have an inhibitory activity on enzymes.{{Cite journal | last1 = Griffiths | first1 = D. W. | title = The polyphenolic content and enzyme inhibitory activity of testas from bean (Vicia faba) and pea (Pisum spp.) varieties | doi = 10.1002/jsfa.2740320808 | journal = Journal of the Science of Food and Agriculture | volume = 32 | issue = 8 | pages = 797–804 | year = 1981 }} Cistus salviifolius also contains oligomeric procyanidins.{{Cite journal | last1 = Qa’Dan | first1 = F. | last2 = Petereit | first2 = F. | last3 = Mansoor | first3 = K. | last4 = Nahrstedt | first4 = A. | title = Antioxidant oligomeric proanthocyanidins fromCistus salvifolius | doi = 10.1080/14786410600899225 | journal = Natural Product Research | volume = 20 | issue = 13 | pages = 1216–1224 | year = 2006 | pmid = 17127512| s2cid = 254865 }}

Condensed tannins can be characterised by a number of techniques including depolymerisation, asymmetric flow field flow fractionation or small-angle X-ray scattering. DMACA is a dye used for localization of procyanidin compounds in plant histology. The use of the reagent results in blue staining.{{cite journal |last1=Bogs |first1=J. |last2=Jaffe |first2=F. W. |last3=Takos |first3=A. M. |last4=Walker |first4=A. R. |last5=Robinson |first5=S. P. |title=The Grapevine Transcription Factor VvMYBPA1 Regulates Proanthocyanidin Synthesis during Fruit Development |journal=Plant Physiology |volume=143 |issue=3 |pages=1347–1361 |year=2007 |pmid=17208963 |pmc=1820911 |doi=10.1104/pp.106.093203}} It can also be used to titrate procyanidins. Total phenols (or antioxidant effect) can be measured using the Folin-Ciocalteu reaction. Results are typically expressed as gallic acid equivalents (GAE).

Procyanidins from field beans (Vicia faba){{Cite journal | last1 = Cabrera | first1 = A. | last2 = Martin | first2 = A. | doi = 10.1017/S0021859600084665 | title = Genetics of tannin content and its relationship with flower and testa colours in Vicia faba | journal = The Journal of Agricultural Science | volume = 113 | pages = 93–98 | year = 2009 | s2cid = 84456901 }} or barley{{Cite journal | last1 = Kristensen | first1 = H. | last2 = Aastrup | first2 = S. | doi = 10.1007/BF02906893 | title = A non-destructive screening method for proanthocyanidin-free barley mutants | journal = Carlsberg Research Communications | volume = 51 | issue = 7 | pages = 509–513 | year = 1986 | doi-access = free }} have been estimated using the vanillin-HCl method, resulting in a red color of the test in the presence of catechin or proanthocyanidins.

Procyanidins can be titrated using the Procyanidolic Index (also called the Bates-Smith Assay). It is a testing method that measures the change in color when the product is mixed with certain chemicals. The greater the color changes, the higher the PCOs content is. However, the Procyanidolic Index is a relative value that can measure well over 100. Unfortunately, a Procyanidolic Index of 95 was erroneously taken to mean 95% PCO by some and began appearing on the labels of finished products. All current methods of analysis suggest that the actual PCO content of these products is much lower than 95%.[http://www.activin.com/Testing%20White%20paper__.html Grape Seed Extract, White paper, The Grape Seed Method Evaluation Committee, Under the Auspices of NNFA ComPli] {{webarchive|url=https://web.archive.org/web/20021224073156/http://www.activin.com/Testing%20White%20paper__.html |date=2002-12-24 }}{{Unreliable medical source|date=October 2010}}

An improved colorimetric test, called the Porter Assay or butanol-HCl-iron method, is the most common PCO assay currently in use.[http://www.activin.com/learn/truthopc.pdf The Truth About PCOs, Debasis Bagchi, Ph.D. on www.activin.com] {{webarchive|url=https://web.archive.org/web/20131019220701/http://www.activin.com/learn/truthopc.pdf |date=2013-10-19 }}{{Self-published inline|Debasis Bagchi is Senior Vice President R&D at InterHealth Nutraceuticals http://www.interhealthusa.com/about/leadership-team.aspx|date=October 2010}} The unit of measurement of the Porter Assay is the PVU (Porter Value Unit). The Porter Assay is a chemical test to help determine the potency of procyanidin containing compounds, such as grape seed extract. It is an acid hydrolysis, which splits larger chain units (dimers and trimers) into single unit monomers and oxidizes them. This leads to a colour change, which can be measured using a spectrophotometer. The greater the absorbance at a certain wavelength of light, the greater the potency. Ranges for grape seed extract are from 25 PVU for low grade material to over 300 for premium grape seed extracts.[http://www.omegabiotech.com/product_analysis_certification.htm Porter Assay on www.omegabiotech.com]{{Unreliable medical source|date=October 2010}}

Gel permeation chromatography (GPC) analysis allows to separate monomers from larger PCO molecules.

Monomers of procyanidins can be characterized by HPLC analysis. Condensed tannins can undergo acid-catalyzed cleavage in the presence of a nucleophile like phloroglucinol (reaction called phloroglucinolysis), thioglycolic acid (thioglycolysis), benzyl mercaptan or cysteamine (processes called thiolysis{{cite journal |last1=Torres |first1=J. L. |last2=Lozano |first2=C. |title=Chromatographic characterization of proanthocyanidins after thiolysis with cysteamine |journal=Chromatographia |volume=54 |pages=523–526 |year=2001 |doi=10.1007/BF02491211 |issue=7–8|s2cid=95355684 }}) leading to the formation of oligomers that can be further analyzed.{{cite journal |last1=Jorgensen |first1=Emily M. |last2=Marin |first2=Anna B. |last3=Kennedy |first3=James A. |title=Analysis of the Oxidative Degradation of Proanthocyanidins under Basic Conditions |journal=Journal of Agricultural and Food Chemistry |volume=52 |issue=8 |pages=2292–2296 |year=2004 |pmid=15080635 |doi=10.1021/jf035311i}}

Phloroglucinolysis can be used for instance for procyanidins characterisation in wine[http://www.ajevonline.org/cgi/content/abstract/57/4/481 Analysis of Tannins in Red Wine Using Multiple Methods: Correlation with Perceived Astringency by mean of depolymerisation] James A. Kennedy, Jordan Ferrier, James F. Harbertson and Catherine Peyrot des Gachons, Am. J. Enol. Vitic. 57:4, 2006, pp. 481–485 or in the grape seed and skin tissues.{{Cite journal | last1 = Kennedy | first1 = J. A. | last2 = Jones | first2 = G. P. | doi = 10.1021/jf001030o | title = Analysis of Proanthocyanidin Cleavage Products Following Acid-Catalysis in the Presence of Excess Phloroglucinol | journal = Journal of Agricultural and Food Chemistry | volume = 49 | issue = 4 | pages = 1740–1746 | year = 2001 | pmid = 11308320}}

Thioglycolysis can be used to study procyanidins{{Cite journal | last1 = Sears | first1 = K. D. | last2 = Casebier | first2 = R. L. | doi = 10.1039/C19680001437 | title = Cleavage of proanthocyanidins with thioglycollic acid | journal = Chemical Communications | issue = 22 | pages = 1437 | year = 1968 }} or the oxidation of condensed tannins.{{Cite journal

| last1 = Vernhet | first1 = A.

| last2 = Dubascoux | first2 = S. P.

| last3 = Cabane | first3 = B.

| last4 = Fulcrand | first4 = H. L. N.

| last5 = Dubreucq | first5 = E.

| last6 = Poncet-Legrand | first6 = C. L.

| doi = 10.1007/s00216-011-5076-2

| title = Characterization of oxidized tannins: Comparison of depolymerization methods, asymmetric flow field-flow fractionation and small-angle X-ray scattering

| journal = Analytical and Bioanalytical Chemistry

| volume = 401

| issue = 5

| pages = 1559–1569

| year = 2011

| pmid = 21573842

| s2cid = 4645218

}} {{Cite journal | last1 = Vernhet | first1 = A. | last2 = Dubascoux | first2 = S. P. | last3 = Cabane | first3 = B. | last4 = Fulcrand | first4 = H. L. N. | last5 = Dubreucq | first5 = E. | last6 = Poncet-Legrand | first6 = C. L. | doi = 10.1007/s00216-011-5076-2 | title = Characterization of oxidized tannins: Comparison of depolymerization methods, asymmetric flow field-flow fractionation and small-angle X-ray scattering | journal = Analytical and Bioanalytical Chemistry | volume = 401 | issue = 5 | pages = 1559–1569 | year = 2011 | pmid = 21573842 | s2cid = 4645218 }} It is also used for lignin quantitation.{{Cite journal

| last1 = Lange | first1 = B. M.

| last2 = Lapierre | first2 = C.

| last3 = Sandermann Jr | first3 = H.

| title = Elicitor-Induced Spruce Stress Lignin (Structural Similarity to Early Developmental Lignins)

| journal = Plant Physiology

| volume = 108

| issue = 3

| pages = 1277–1287

| year = 1995

| pmid = 12228544

| pmc = 157483

| doi = 10.1104/pp.108.3.1277

}} Reaction on condensed tannins from Douglas fir bark produces epicatechin and catechin thioglycolates.[http://ir.library.oregonstate.edu/xmlui/bitstream/handle/1957/16902/SongHongKeun1985.pdf?sequence=1 Douglas-Fir Bark: Characterization of a Condensed Tannin Extract, by Hong-Keun Song, A thesis submitted to Oregon State University in partial fulfillment of the requirements for the degree of Master of Science, December 13, 1984]

Condensed tannins from Lithocarpus glaber leaves have been analysed through acid-catalyzed degradation in the presence of cysteamine.{{Cite journal | last1 = Zhang | first1 = L. L. | last2 = Lin | first2 = Y. M. | doi = 10.3390/molecules13122986 | title = HPLC, NMR and MALDI-TOF MS Analysis of Condensed Tannins from Lithocarpus glaber Leaves with Potent Free Radical Scavenging Activity | journal = Molecules | volume = 13 | issue = 12 | pages = 2986–2997 | year = 2008 | pmid = 19052523| pmc = 6245341| doi-access = free }}

Procyanidin content in dietary supplements has not been well documented.{{Cite book |title=USDA Database for the Proanthocyanidin Content of Selected Foods |url=http://www.nal.usda.gov/fnic/foodcomp/Data/PA/PA.pdf |date=August 2004 |access-date=2013-01-09 |archive-url=https://web.archive.org/web/20101016223806/http://www.nal.usda.gov/fnic/foodcomp/Data/PA/PA.pdf |archive-date=2010-10-16 |url-status=dead }}{{Page needed|date=August 2010}} Pycnogenol is a dietary supplement derived from extracts from maritime pine bark that contains 70% procyanidins, and is marketed with claims it can treat many conditions. The medical evidence is insufficient to support its use for the treatment of seven different chronic disorders.{{Cite journal|last1=Robertson|first1=Nina U.|last2=Schoonees|first2=Anel|last3=Brand|first3=Amanda|last4=Visser|first4=Janicke|date=29 September 2020|title=Pine bark (Pinus spp.) extract for treating chronic disorders|journal=The Cochrane Database of Systematic Reviews|volume=2020|issue=9|pages=CD008294|doi=10.1002/14651858.CD008294.pub5|issn=1469-493X|pmid=32990945|pmc=8094515}}

• A type proanthocyanidin
• B type proanthocyanidin
• Procyanidin C1
• Procyanidin C2
• Tannin
• Polyphenol
• Phenolic compounds in wine

{{reflist|colwidth=35em}}

{{Commons category|Procyanidins}}

• [https://medlineplus.gov/druginfo/natural/1019.html "Pycnogenol: MedlinePlus Supplements"]

{{Plant pigments}}

{{Condensed tannin}}

{{Procyanidin}}

Category:Food chemistry

Category:Flavonoid antioxidants

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