Prodelphinidin Explained

Prodelphinidin is a name for the polymeric tannins composed of gallocatechin.^{[1] [2] [3]} It yields delphinidin during depolymerisation under oxidative conditions.

Natural occurrences

Prodelphinidins are one of the two sorts of tannins in grape (the other being procyanidins) being produced especially in the skin of the berry.^[4]

Prodelphinidins can be found in Cistus salviifolius.^[5] Gallocatechin-(4→8)-catechin (prodelphinidin B3), gallocatechin-(4→8)-gallocatechin and catechin-(4→8)-gallocatechin can be found in the pomegranate peels.^[6] Prodelphinidin B-2 3'-O-gallate can be found in green tea leaves^[7] and prodelphinidin B-2 3,3'-di-O-gallate can be found in Myrica rubra.^[8]

Particular oligomeric prodelphinidins

Prodelphinidin B3 (gallocatechin-(4α→8)-catechin) and prodelphinidin B9 (epigallocatechin-(4α→8)-catechin) can be isolated in beer.^{[9] [10]} Prodelphinidin C2 (gallocatechin-(4α→8)-gallocatechin-(4α→8)-catechin) can be isolated in malt.^[11]

The A-type proanthocyanidin epigallocatechin-(2β→7,4β→8)-epicatechin can be found in the leaves of Dioclea lasiophylla,^[12]

See also

• Crofelemer, a complex mixture of procyanidins and prodelphinidins from the latex of the South American tree Croton lechleri (locally called Sangre de Grado or Sangre de Drago)

Notes and References

1. Porter, 1992
2. Afidah A. . Rahima . Emmanuel . Roccab . Jean . Steinmetzb . M. Jain . Kassima . M. Sani . Ibrahima . Hasnah . Osman . Antioxidant activities of mangrove Rhizophora apiculata bark extracts . Food Chemistry . 107 . 1 . 200–207 . 1 March 2008 . 10.1016/j.foodchem.2007.08.005 .
3. Prodelphinidin polymers: definition of structural units. Lai Yeap Foo and Lawrence J. Porter. J. Chem. Soc., Perkin Trans. 1, 1978, pp. 1186–1190,
4. Polymeric proanthocyanidins from grape skins. Jean-Marc Souquet, Véronique Cheynier, Franck Brossaud and Michel Moutounet, Phytochemistry, volume 43, Issue 2, September 1996, Pages 509–512,
5. Flavan-3-ols, prodelphinidins and further polyphenols from Cistus salvifolius. Andreas Danne, Frank Petereit and Adolf Nahrstedt, Phytochemistry, Volume 37, Issue 2, 1994, Pages 533–538,
6. Antioxidant properties of gallocatechin and prodelphinidins from pomegranate peel. Plumb G. W., de Pascual-Teresa S, Santos-Buelga C, Rivas-Gonzalo J. C and Williamson G, Redox Report, February 2002, Volume 7, Number 1, pages 41–46,
7. Cheng HY, Lin CC, Lin TC . Antiviral properties of prodelphinidin B-2 3'-O-gallate from green tea leaf . Antivir. Chem. Chemother. . 13 . 4 . 223–229 . July 2002 . 12495210 . 10.1177/095632020201300403 . free .
8. Cheng HY, Lin TC, Ishimaru K, Yang CM, Wang KC, Lin CC . In vitro antiviral activity of prodelphinidin B-2 3,3'-di-O-gallate from Myrica rubra . Planta Med. . 69 . 10 . 953–956 . October 2003 . 14648402 . 10.1055/s-2003-45108 .
9. PhD . Structure elucidation of proanthocyanidins: Direct synthesis and isolation from Pilsener beer . Delcour . Jan . 1985 . Katholieke Universiteit Leuven .
10. Phenolic Compounds in Beer. Clarissa Gerhäuser and Hans Becker, Beer in Health and Disease Prevention, 2009 (article)
11. Menelaos . Papagiannopoulos . Benno . Zimmermann . Annett . Mellenthin . Martin . Krappe . Giovanni . Maio . Rudolf . Galensa . Online coupling of pressurized liquid extraction, solid-phase extraction and high-performance liquid chromatography for automated analysis of proanthocyanidins in malt . Journal of Chromatography A . 958 . 1–2 . 9–16 . 7 June 2002 . 12134835 . 10.1016/S0021-9673(02)00364-3 .
12. 11190400 . December 2000 . André L. B. S. . Barreiros . Juceni P. . David . Luciano P. . de Queiroz . Jorge M. . David . A-type proanthocyanidin antioxidant from Dioclea lasiophylla . 55 . 7 . 805–808 . Phytochemistry . 10.1016/S0031-9422(00)00297-1.