Procyanidin C1 (PCC1) is a
B type proanthocyanidin
B type proanthocyanidins are a specific type of proanthocyanidin, which are a class of flavanoids. They are oligomers of flavan-3-ols.
Dimeric B type proanthocyanidins
These molecules have the molecular formula C30H26O12 (molar mass : 578.52 g/m ...
. It is an
epicatechin
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.
The name of the catechin chemical family derives from ''catechu'', which is the tannic ...
trimer found in grape (''
Vitis vinifera
''Vitis vinifera'', the common grape vine, is a species of flowering plant, native to the Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern Iran. There are curre ...
''), unripe apples,
and
cinnamon
Cinnamon is a spice obtained from the inner bark of several tree species from the genus ''Cinnamomum''. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, breakfa ...
.
Natural occurrence and function
Procyanidin C1 can be isolated from grape seed extract.
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
Trimethylsilyl trifluoromethanesulfonate is a trifluoromethanesulfonate derivate with a trimethylsilyl R-group. It has similar reactivity to trimethylsilyl chloride, and is also used often in organic synthesis.
Illustrative reactions
A common ap ...
-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.
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
Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemotherap ...
in mice in which human
prostate tumor cells were implanted.
See also
* Phenolic content in wine
External Links
* Carissa Wong
Grape seed chemical allows mice to live longer by killing aged cells
NewScientist, 6 December 2021
References
Procyanidins
Natural phenol trimers
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