Procyanidin B3 Explained

Procyanidin B3 is a B type proanthocyanidin. Procyanidin B3 is a catechin dimer (catechin-(4α→8)-catechin).

Natural occurrences

It can be found in red wine,[1] in barley,[2] [3] in beer,[4] in peach[5] or in Jatropha macrantha, the Huanarpo Macho.[6]

Health effects

It has been identified as a hair-growth stimulant.[2]

Chemical synthesis

Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-[4,8]- and [4,6]-bi-[(+)-catechins] (procyanidins B3, B6) the all-trans-[4,8:4,8]- and [4,8:4,6]-tri-[(+)-catechins] (procyanidin C2 and isomer).[7]

See also

Notes and References

  1. Degradation of oligomeric procyanidins and anthocyanins in a Tinta Roriz red wine during maturation. C. Dallas, J.M. Ricardo-Da-Silva and Olga Laureano. Vitis. 1995. 34. 1. 51–56. 2013-06-24. https://web.archive.org/web/20131203051305/http://www.vitis-vea.de/admin/volltext/e034753.pdf. 2013-12-03. dead.
  2. 12473061. 2002. Kamimura. A. Takahashi. T. Procyanidin B-3, isolated from barley and identified as a hair-growth stimulant, has the potential to counteract inhibitory regulation by TGF-beta1. 11. 6. 532–41. Experimental Dermatology. 10.1034/j.1600-0625.2002.110606.x. 39454993.
  3. 10.1021/jf060974w. Phenolic Compounds of Barley Grain and Their Implication in Food Product Discoloration. 2006. Quinde-Axtell. Zory. Baik. Byung-Kee. Journal of Agricultural and Food Chemistry. 54. 26. 9978–84. 17177530.
  4. Book: Delcour, Jan . Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer. 1985.
  5. 10.4067/S0718-58392011000300016. Postharvest Sensory and Phenolic Characterization of 'Elegant Lady' and 'Carson' Peaches . 2011. Infante. Rodrigo. Contador. Loreto. Rubio. Pía. Aros. Danilo. Peña-Neira. Álvaro. Chilean Journal of Agricultural Research. 71. 3. 445–451 . free.
  6. 10.1016/j.jpba.2005.10.004. Catechin derivatives in Jatropha macrantha stems: Characterisation and LC/ESI/MS/MS quali–quantitative analysis. 2006. Benavides. Angelyne. Montoro. Paola. Bassarello. Carla. Piacente. Sonia. Pizza. Cosimo. Journal of Pharmaceutical and Biomedical Analysis. 40. 3. 639–47. 16300918.
  7. 10.1039/P19830001711. Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins. 1983. Delcour. Jan. A.. Ferreira. Daneel. Roux. David G.. Journal of the Chemical Society, Perkin Transactions 1. 1711.

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