fbpx
Wikipedia

Procyanidin C2

February 15, 2024

Procyanidin C2 is a B type proanthocyanidin trimer, a type of condensed tannin.

Procyanidin C2
Names
IUPAC name
[(2R,3S,4S)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3S,4R)-flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3S)-flavan-3,3′,4′,5,7-pentol]
Preferred IUPAC name
(12R,13S,14S,22R,23S,24R,32R,33S)-12,22,32-Tris(3,4-dihydroxyphenyl)-13,14,23,24,33,34-hexahydro-12H,22H,32H-[14,28:24,38-ter-1-benzopyran]-13,15,17,23,25,27,33,35,37-nonol
Other names
C-(4,8)-C-(4,8)-C
Procyanidin trimer C2
Catechin-(4alpha→8)-Catechin-(4alpha→8)-Catechin
Catechin-(4α→8)-catechin-(4α→8)-catechin
Trimer C2
Identifiers
  • 37064-31-6
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:75644
ChemSpider
  • 9357147
  • 11182062
  • InChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41+,42+,43+/m0/s1
    Key: MOJZMWJRUKIQGL-WNCKYJNFSA-N
  • Oc8ccc(cc8O)C(C1O)Oc7cc(O)cc(O)c7C1c3c(O)cc(O)c(c3OC(C5O)c(cc2O)ccc2O)C5c4c6OC(c(cc9O)ccc9O)C(O)Cc6c(O)cc4O
Properties
C45H38O18
Molar mass 866.74 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Natural occurrences edit

Procyanidin C2 is found in grape seeds (Vitis vinifera)[1][2] and wine,[3] in barley (Hordeum vulgare),[4] malt[5] and beer,[6] in Betula spp., in Pinus radiata, in Potentilla viscosa, in Salix caprea or in Cryptomeria japonica.[7][8][9]

The contents in barley grain of trimeric proanthocyanidins, including procyanidin C2, range from 53 to 151 μg catechin equivalents/g.[10]

Possible health uses edit

Proanthocyanidin oligomers, extracted from grape seeds, have been used for the experimental treatment of androgenic alopecia. When applied topically, they promote hair growth in vitro, and induce anagen in vivo. Procyanidin C2 is the subtype of extract most effective.[11]

Experiments showed that both procyanidin C2 and Pycnogenol (French maritime pine bark extract) increase TNF-α secretion in a concentration- and time-dependent manner. These results demonstrate that procyanidins act as modulators of the immune response in macrophages.[12]

Chemistry edit

In the presence of procyanidin C2, the red color of the anthocyanin oenin appears more stable. However, the HPLC chromatogram shows a decrease in the amplitude of the peaks of oenin and procyanidin C2. Concomitantly, a new peak appears with a maximal absorption in the red region. This newly formed pigment probably comes from the condensation of oenin and procyanidin C2.[13]

Chemical synthesis edit

A stereoselective synthesis of benzylated catechin trimer under intermolecular condensation is achieved using equimolar amount of dimeric catechin nucleophile and monomeric catechin electrophile catalyzed by AgOTf or AgBF4. The coupled product can be transformed into procyanidin C2 by a known procedure.[14]

The stereoselective synthesis of seven benzylated proanthocyanidin trimers (epicatechin-(4β-8)-epicatechin-(4β-8)-epicatechin trimer (procyanidin C1), catechin-(4α-8)-catechin-(4α-8)-catechin trimer (procyanidin C2), epicatechin-(4β-8)-epicatechin-(4β-8)-catechin trimer and epicatechin-(4β-8)-catechin-(4α-8)-epicatechin trimer derivatives) can be achieved with TMSOTf-catalyzed condensation reaction, in excellent yields. The structure of benzylated procyanidin C2 was confirmed by comparing the 1H NMR spectra of protected procyanidin C2 that was synthesized by two different condensation approaches. Finally, deprotection of (+)-catechin and (−)-epicatechin trimers derivatives gives four natural procyanidin trimers in good yields.[15]

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).[16]

Iterative oligomer chemical synthesis edit

A coupling utilising a C8-boronic acid as a directing group was developed in the synthesis of natural procyanidin B3 (i.e., 3,4-trans-(+)-catechin-4α→8-(+)-catechin dimer). The key interflavan bond is forged using a Lewis acid-promoted coupling of C4-ether with C8-boronic acid to provide the α-linked dimer with high diastereoselectivity. Through the use of a boron protecting group, the coupling procedure can be extended to the synthesis of a protected procyanidin trimer analogous to natural procyanidin C2.[17]

See also edit

References edit

  1. ^ Romeyer FM, Macheix JJ, Sapis JC (1985). "Changes and importance of oligomeric procyanidins during maturation of grape seeds". Phytochemistry. 25: 219–221. doi:10.1016/S0031-9422(00)94532-1.
  2. ^ Tsang C, Auger C, Mullen W, Bornet A, Rouanet JM, Crozier A, Teissedre PL (August 2005). "The absorption, metabolism and excretion of flavan-3-ols and procyanidins following the ingestion of a grape seed extract by rats". The British Journal of Nutrition. 94 (2): 170–81. doi:10.1079/BJN20051480. PMID 16115350.
  3. ^ Identification of the condensed tannins content in grape and Bordeaux wine by means of standards of synthesis. S. Fabre, E. Fouquet, I. Pianet and P-L. Teissedre (article 2016-03-04 at the Wayback Machine)
  4. ^ Kristiansen KN (1984). "Biosynthesis of proanthocyanidins in barley: Genetic control of the conversion of dihydroquercetin to catechin and procyanidins". Carlsberg Research Communications. 49 (5): 503–524. doi:10.1007/BF02907552.
  5. ^ Goupy P, Hugues M, Boivin P, Amiot MJ (1999). "Antioxidant composition and activity of barley (Hordeum vulgare) and malt extracts and of isolated phenolic compounds". Journal of the Science of Food and Agriculture. 79 (12): 1625–1634. doi:10.1002/(SICI)1097-0010(199909)79:12<1625::AID-JSFA411>3.0.CO;2-8.
  6. ^ McMurrough I, Madigan D, Smyth MR (1996). "Semipreparative Chromatographic Procedure for the Isolation of Dimeric and Trimeric Proanthocyanidins from Barley". Journal of Agricultural and Food Chemistry. 44 (7): 1731–1735. doi:10.1021/jf960139m.
  7. ^ Harborne JB, Baxter H (1999). "Flavans and Proanthocyanidins". The Handbook of Natural Flavonoids. Vol. 2. Chichester: Wiley. p. 355. ISBN 978-0-471-95893-2.
  8. ^ Thompson RS, Jacques D, Haslam E, Tanner RJ (1972). "Plant proanthocyanidins. Part I. Introduction; the isolation, structure, and distribution in nature of plant procyanidins". Journal of the Chemical Society, Perkin Transactions 1: 1387. doi:10.1039/P19720001387.
  9. ^ Brandon MJ, Foo LY, Porter LJ, Meredith P (1980). "Proanthocyanidins of barley and sorghum; composition as a function of maturity of barley ears". Phytochemistry. 21 (12): 2953–2957. doi:10.1016/0031-9422(80)85076-X.
  10. ^ Quinde-Axtell Z, Baik BK (December 2006). "Phenolic compounds of barley grain and their implication in food product discoloration". Journal of Agricultural and Food Chemistry. 54 (26): 9978–84. doi:10.1021/jf060974w. PMID 17177530.
  11. ^ Takahashi T, Kamiya T, Hasegawa A, Yokoo Y (March 1999). "Procyanidin oligomers selectively and intensively promote proliferation of mouse hair epithelial cells in vitro and activate hair follicle growth in vivo". The Journal of Investigative Dermatology. 112 (3): 310–6. doi:10.1046/j.1523-1747.1999.00532.x. PMID 10084307.
  12. ^ Park YC, Rimbach G, Saliou C, Valacchi G, Packer L (January 2000). "Activity of monomeric, dimeric, and trimeric flavonoids on NO production, TNF-alpha secretion, and NF-kappaB-dependent gene expression in RAW 264.7 macrophages". FEBS Letters. 465 (2–3): 93–7. doi:10.1016/S0014-5793(99)01735-4. PMID 10631311.
  13. ^ Malien-Aubert C, Dangles O, Amiot MJ (May 2002). "Influence of procyanidins on the color stability of oenin solutions". Journal of Agricultural and Food Chemistry. 50 (11): 3299–305. doi:10.1021/jf011392b. PMID 12010001.
  14. ^ Makabe H, Oizumi Y, Mohri Y, Hattori Y (2011). "Efficient Stereoselective Synthesis of Catechin Trimer Derivative Using Silver Lewis Acid-Mediated Equimolar Condensation". Heterocycles. 83 (4): 739. doi:10.3987/COM-11-12159. hdl:10091/16138.
  15. ^ Nakajima N, Saito A, Tanaka A, Ubukata M (2004). "Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation". Synlett (6): 1069–1073. doi:10.1055/s-2004-822905.
  16. ^ Delcour JA, Ferreira D, Roux DG (1983). "Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins". Journal of the Chemical Society, Perkin Transactions 1: 1711. doi:10.1039/P19830001711.
  17. ^ Dennis EG, Jeffery DW, Johnston MR, Perkins MV, Smith PA (2012). "Procyanidin oligomers. A new method for 4→8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy". Tetrahedron. 68: 340–348. doi:10.1016/j.tet.2011.10.039. hdl:2440/76362. INIST 25254810.

External links edit

February 15, 2024
procyanidin, type, proanthocyanidin, trimer, type, condensed, tannin, namesiupac, name, flavan, pentol, flavan, pentol, flavan, pentol, preferred, iupac, name, tris, dihydroxyphenyl, hexahydro, benzopyran, nonolother, names, cprocyanidin, trimer, c2catechin, 4. Procyanidin C2 is a B type proanthocyanidin trimer a type of condensed tannin Procyanidin C2 NamesIUPAC name 2R 3S 4S Flavan 3 3 4 5 7 pentol 4 8 2R 3S 4R flavan 3 3 4 5 7 pentol 4 8 2R 3S flavan 3 3 4 5 7 pentol Preferred IUPAC name 12R 13S 14S 22R 23S 24R 32R 33S 12 22 32 Tris 3 4 dihydroxyphenyl 13 14 23 24 33 34 hexahydro 12H 22H 32H 14 28 24 38 ter 1 benzopyran 13 15 17 23 25 27 33 35 37 nonolOther names C 4 8 C 4 8 CProcyanidin trimer C2Catechin 4alpha 8 Catechin 4alpha 8 CatechinCatechin 4a 8 catechin 4a 8 catechinTrimer C2IdentifiersCAS Number 37064 31 63D model JSmol Interactive imageChEBI CHEBI 75644ChemSpider 9357147PubChem CID 11182062InChI InChI 1S C45H38O18 c46 18 10 27 54 33 32 11 18 61 42 16 2 5 21 48 25 52 8 16 39 59 37 33 35 29 56 14 30 57 36 38 40 60 43 63 45 35 36 17 3 6 22 49 26 53 9 17 34 28 55 13 23 50 19 12 31 58 41 62 44 19 34 15 1 4 20 47 24 51 7 15 h1 11 13 14 31 37 43 46 60H 12H2 t31 37 38 39 40 41 42 43 m0 s1Key MOJZMWJRUKIQGL WNCKYJNFSA NSMILES Oc8ccc cc8O C C1O Oc7cc O cc O c7C1c3c O cc O c c3OC C5O c cc2O ccc2O C5c4c6OC c cc9O ccc9O C O Cc6c O cc4OPropertiesChemical formula C45H38O18Molar mass 866 74 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Natural occurrences 2 Possible health uses 3 Chemistry 3 1 Chemical synthesis 3 2 Iterative oligomer chemical synthesis 4 See also 5 References 6 External linksNatural occurrences editProcyanidin C2 is found in grape seeds Vitis vinifera 1 2 and wine 3 in barley Hordeum vulgare 4 malt 5 and beer 6 in Betula spp in Pinus radiata in Potentilla viscosa in Salix caprea or in Cryptomeria japonica 7 8 9 The contents in barley grain of trimeric proanthocyanidins including procyanidin C2 range from 53 to 151 mg catechin equivalents g 10 Possible health uses editProanthocyanidin oligomers extracted from grape seeds have been used for the experimental treatment of androgenic alopecia When applied topically they promote hair growth in vitro and induce anagen in vivo Procyanidin C2 is the subtype of extract most effective 11 Experiments showed that both procyanidin C2 and Pycnogenol French maritime pine bark extract increase TNF a secretion in a concentration and time dependent manner These results demonstrate that procyanidins act as modulators of the immune response in macrophages 12 Chemistry editIn the presence of procyanidin C2 the red color of the anthocyanin oenin appears more stable However the HPLC chromatogram shows a decrease in the amplitude of the peaks of oenin and procyanidin C2 Concomitantly a new peak appears with a maximal absorption in the red region This newly formed pigment probably comes from the condensation of oenin and procyanidin C2 13 Chemical synthesis edit A stereoselective synthesis of benzylated catechin trimer under intermolecular condensation is achieved using equimolar amount of dimeric catechin nucleophile and monomeric catechin electrophile catalyzed by AgOTf or AgBF4 The coupled product can be transformed into procyanidin C2 by a known procedure 14 The stereoselective synthesis of seven benzylated proanthocyanidin trimers epicatechin 4b 8 epicatechin 4b 8 epicatechin trimer procyanidin C1 catechin 4a 8 catechin 4a 8 catechin trimer procyanidin C2 epicatechin 4b 8 epicatechin 4b 8 catechin trimer and epicatechin 4b 8 catechin 4a 8 epicatechin trimer derivatives can be achieved with TMSOTf catalyzed condensation reaction in excellent yields The structure of benzylated procyanidin C2 was confirmed by comparing the 1H NMR spectra of protected procyanidin C2 that was synthesized by two different condensation approaches Finally deprotection of catechin and epicatechin trimers derivatives gives four natural procyanidin trimers in good yields 15 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 16 Iterative oligomer chemical synthesis edit A coupling utilising a C8 boronic acid as a directing group was developed in the synthesis of natural procyanidin B3 i e 3 4 trans catechin 4a 8 catechin dimer The key interflavan bond is forged using a Lewis acid promoted coupling of C4 ether with C8 boronic acid to provide the a linked dimer with high diastereoselectivity Through the use of a boron protecting group the coupling procedure can be extended to the synthesis of a protected procyanidin trimer analogous to natural procyanidin C2 17 See also editPhenolic content in wineReferences edit Romeyer FM Macheix JJ Sapis JC 1985 Changes and importance of oligomeric procyanidins during maturation of grape seeds Phytochemistry 25 219 221 doi 10 1016 S0031 9422 00 94532 1 Tsang C Auger C Mullen W Bornet A Rouanet JM Crozier A Teissedre PL August 2005 The absorption metabolism and excretion of flavan 3 ols and procyanidins following the ingestion of a grape seed extract by rats The British Journal of Nutrition 94 2 170 81 doi 10 1079 BJN20051480 PMID 16115350 Identification of the condensed tannins content in grape and Bordeaux wine by means of standards of synthesis S Fabre E Fouquet I Pianet and P L Teissedre article Archived 2016 03 04 at the Wayback Machine Kristiansen KN 1984 Biosynthesis of proanthocyanidins in barley Genetic control of the conversion of dihydroquercetin to catechin and procyanidins Carlsberg Research Communications 49 5 503 524 doi 10 1007 BF02907552 Goupy P Hugues M Boivin P Amiot MJ 1999 Antioxidant composition and activity of barley Hordeum vulgare and malt extracts and of isolated phenolic compounds Journal of the Science of Food and Agriculture 79 12 1625 1634 doi 10 1002 SICI 1097 0010 199909 79 12 lt 1625 AID JSFA411 gt 3 0 CO 2 8 McMurrough I Madigan D Smyth MR 1996 Semipreparative Chromatographic Procedure for the Isolation of Dimeric and Trimeric Proanthocyanidins from Barley Journal of Agricultural and Food Chemistry 44 7 1731 1735 doi 10 1021 jf960139m Harborne JB Baxter H 1999 Flavans and Proanthocyanidins The Handbook of Natural Flavonoids Vol 2 Chichester Wiley p 355 ISBN 978 0 471 95893 2 Thompson RS Jacques D Haslam E Tanner RJ 1972 Plant proanthocyanidins Part I Introduction the isolation structure and distribution in nature of plant procyanidins Journal of the Chemical Society Perkin Transactions 1 1387 doi 10 1039 P19720001387 Brandon MJ Foo LY Porter LJ Meredith P 1980 Proanthocyanidins of barley and sorghum composition as a function of maturity of barley ears Phytochemistry 21 12 2953 2957 doi 10 1016 0031 9422 80 85076 X Quinde Axtell Z Baik BK December 2006 Phenolic compounds of barley grain and their implication in food product discoloration Journal of Agricultural and Food Chemistry 54 26 9978 84 doi 10 1021 jf060974w PMID 17177530 Takahashi T Kamiya T Hasegawa A Yokoo Y March 1999 Procyanidin oligomers selectively and intensively promote proliferation of mouse hair epithelial cells in vitro and activate hair follicle growth in vivo The Journal of Investigative Dermatology 112 3 310 6 doi 10 1046 j 1523 1747 1999 00532 x PMID 10084307 Park YC Rimbach G Saliou C Valacchi G Packer L January 2000 Activity of monomeric dimeric and trimeric flavonoids on NO production TNF alpha secretion and NF kappaB dependent gene expression in RAW 264 7 macrophages FEBS Letters 465 2 3 93 7 doi 10 1016 S0014 5793 99 01735 4 PMID 10631311 Malien Aubert C Dangles O Amiot MJ May 2002 Influence of procyanidins on the color stability of oenin solutions Journal of Agricultural and Food Chemistry 50 11 3299 305 doi 10 1021 jf011392b PMID 12010001 Makabe H Oizumi Y Mohri Y Hattori Y 2011 Efficient Stereoselective Synthesis of Catechin Trimer Derivative Using Silver Lewis Acid Mediated Equimolar Condensation Heterocycles 83 4 739 doi 10 3987 COM 11 12159 hdl 10091 16138 Nakajima N Saito A Tanaka A Ubukata M 2004 Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf Catalyzed Intermolecular Condensation Synlett 6 1069 1073 doi 10 1055 s 2004 822905 Delcour JA Ferreira D Roux DG 1983 Synthesis of condensed tannins Part 9 The condensation sequence of leucocyanidin with catechin and with the resultant procyanidins Journal of the Chemical Society Perkin Transactions 1 1711 doi 10 1039 P19830001711 Dennis EG Jeffery DW Johnston MR Perkins MV Smith PA 2012 Procyanidin oligomers A new method for 4 8 interflavan bond formation using C8 boronic acids and iterative oligomer synthesis through a boron protection strategy Tetrahedron 68 340 348 doi 10 1016 j tet 2011 10 039 hdl 2440 76362 INIST 25254810 External links editProcyanidin C2 at Phenol Explorer eu knapsack Retrieved from https en wikipedia org w index php title Procyanidin C2 amp oldid 1138830524, wikipedia, wiki, book, books, library,

article

, read, download, free, free download, mp3, video, mp4, 3gp, jpg, jpeg, gif, png, picture, music, song, movie, book, game, games.