Procyanidin C1

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Procyanidin C1
Procyanidin C1.svg
Names
IUPAC name
[(2R,3R,4R)-Flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3R,4S)-flavan-3,3′,4′,5,7-pentol]-(4→8)-[(2R,3R)-flavan-3,3′,4′,5,7-pentol]
Systematic IUPAC name
(12R,13R,14R,22R,23R,24S,32R,33R)-12,22,32-Tris(3,4-dihydroxyphenyl)-12H,22H,32H-[14,28:24,38-ter-1-benzopyran]-13,15,17,23,25,27,33,35,37-nonol
Other names
Procyanidin C1
Procyanidol C1
Epicatechin-(4.beta.-->8)epicatechin-(4.beta.-->8)epicatechin
Epicatechin-(4β→8)-epicatechin--(4β→8)-epicatechin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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-/m1/s1
    Key: MOJZMWJRUKIQGL-XILRTYJMSA-N
  • InChI=1/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-/m1/s1
    Key: MOJZMWJRUKIQGL-XILRTYJMBW
  • c1cc(c(cc1[C@@H]2[C@@H](Cc3c(cc(c(c3O2)[C@H]4c5c(cc(c(c5O[C@@H]([C@@H]4O)c6ccc(c(c6)O)O)[C@H]7c8c(cc(cc8O[C@@H]([C@@H]7O)c9ccc(c(c9)O)O)O)O)O)O)O)O)O)O)O
Properties
C45H38O18
Molar mass 866.77 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Procyanidin C1 (PCC1) is a B type proanthocyanidin. It is an epicatechin trimer found in grape ( Vitis vinifera ), [1] unripe apples, [2] and cinnamon. [3]

Contents

Natural occurrence and function

Procyanidin C1 can be isolated from grape seed extract. [4]

Chemical synthesis

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. [5]

Research

Procyanidin C1 has been found to extend life in mice and to make them fitter. It was also found to greatly increase the effectiveness of chemotherapy in mice in which human prostate tumor cells were implanted. [4] [6]

See also

Related Research Articles

<span class="mw-page-title-main">Flavan-3-ol</span> Category of polyphenol compound

Flavan-3-ols are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They play a part in plant defense and are present in the majority of plants.

<span class="mw-page-title-main">Catechin</span> Type of natural phenol as a plant secondary metabolite

Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.

Proanthocyanidins are a class of polyphenols found in many plants, such as cranberry, blueberry, and grape seeds. Chemically, they are oligomeric flavonoids. Many are oligomers of catechin and epicatechin and their gallic acid esters. More complex polyphenols, having the same polymeric building block, form the group of tannins.

<span class="mw-page-title-main">Procyanidin</span>

Procyanidins are members of the proanthocyanidin class of flavonoids. They are oligomeric compounds, formed from catechin and epicatechin molecules. They yield cyanidin when depolymerized under oxidative conditions.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Trimethylsilyl trifluoromethanesulfonate</span> Chemical compound

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) is a trifluoromethanesulfonate derivate with a trimethylsilyl R-group. It has similar reactivity to trimethylsilyl chloride, and is also used often in organic synthesis.

<span class="mw-page-title-main">Prodelphinidin</span>

Prodelphinidin is a name for the polymeric tannins composed of gallocatechin. It yields delphinidin during depolymerisation under oxidative conditions.

<span class="mw-page-title-main">Leucocyanidin</span> Chemical compound

Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins.

<span class="mw-page-title-main">Procyanidin C2</span> Chemical compound

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

<span class="mw-page-title-main">Procyanidin B2</span> Chemical compound

Procyanidin B2 is a B type proanthocyanidin. Its structure is (−)-Epicatechin-(4β→8)-(−)-epicatechin.

A type proanthocyanidins are a specific type of proanthocyanidins, which are a class of flavonoid. Proanthocyanidins fall under a wide range of names in the nutritional and scientific vernacular, including oligomeric proanthocyanidins, flavonoids, polyphenols, condensed tannins, and OPCs. Proanthocyanidins were first popularized by French scientist Jacques Masquelier.

The molecular formula C30H26O12 may refer to:

<span class="mw-page-title-main">Procyanidin B1</span> Chemical compound

Procyanidin B1 is a procyanidin dimer.

<span class="mw-page-title-main">Procyanidin B4</span> Chemical compound

Procyanidin B4 is a B type proanthocyanidin.

<span class="mw-page-title-main">Procyanidin B5</span> Chemical compound

Procyanidin B5 is a B type proanthocyanidin.

<span class="mw-page-title-main">Procyanidin B6</span> Chemical compound

Procyanidin B6 is a B type proanthocyanidin.

<span class="mw-page-title-main">Procyanidin B8</span> Chemical compound

Procyanidin B8 is a B type proanthocyanidin.

<span class="mw-page-title-main">Procyanidin A1</span> Chemical compound

Procyanidin A1 is an A type proanthocyanidin dimer.

<span class="mw-page-title-main">Condensed tannin</span> Polymers formed by the condensation of flavans.

Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.

B type proanthocyanidins are a specific type of proanthocyanidin, which are a class of flavanoids. They are oligomers of flavan-3-ols.

References

  1. ↑ Proanthocyanidin composition of red Vitis vinifera varieties from the Douro valley during ripening : Influence of cultivation altitude. Mateus Nuno, Marques Sara, Goncalves Ana C., Machado José M. and De Freitas Victor, American journal of enology and viticulture, 2001, vol. 52, no2, pp. 115-121, INIST : 1129642
  2. ↑ Nakano, Nobuhiro; Nishiyama, Chiharu; Tokura, Tomoko; Nagasako-Akazome, Yoko; Ohtake, Yasuyuki; Okumura, Ko; Ogawa, Hideoki (2008-07-02). "Procyanidin C1 from Apple Extracts Inhibits FcεRI-Mediated Mast Cell Activation". International Archives of Allergy and Immunology. 147 (3): 213–221. doi:10.1159/000142044. ISSN   1018-2438. PMID   18594151. S2CID   43866026 . Retrieved 2022-02-20.
  3. ↑ Sun, Peng; Li, Kai; Wang, Ting; Ji, Jun; Wang, Yan; Chen, Kai-Xian; Jia, Qi; Li, Yi-Ming; Wang, He-Yao (2019-07-23). "Procyanidin C1, a Component of Cinnamon Extracts, Is a Potential Insulin Sensitizer That Targets Adipocytes". Journal of Agricultural and Food Chemistry. American Chemical Society (ACS). 67 (32): 8839–8846. doi:10.1021/acs.jafc.9b02932. ISSN   0021-8561. PMID   31334651. S2CID   198169719.
  4. 1 2 Carissa Wong (Dec 6, 2021). "Grape seed chemical allows mice to live longer by killing aged cells". New Scientist.
  5. ↑ Efficient Stereoselective Synthesis of Proanthocyanidin Trimers with TMSOTf-Catalyzed Intermolecular Condensation. Akiko Saito, Akira Tanaka, Makoto Ubukata and Noriyuki Nakajima, Synlett, 2004, volume 6, pages 1069-1073, doi : 10.1055/s-2004-822905
  6. ↑ Xu, Qixia; et al. (Dec 6, 2021). "The flavonoid procyanidin C1 has senotherapeutic activity and increases lifespan in mice". Nature Metabolism. 3 (12): 1706–1726. doi:10.1038/s42255-021-00491-8. PMC   8688144 . PMID   34873338.


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