Doc:FL63AC
From Metabolomics.JP
(Difference between revisions)
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|- | |- | ||
! Structure | ! Structure | ||
| − | | [[Image:FL63ACNS0001.png| | + | | [[Image:FL63ACNS0001.png|130px]] |
| − | | [[Image:FL63ACNS0002.png| | + | | [[Image:FL63ACNS0002.png|130px]] |
| − | | [[Image:FL63ACNS0004.png| | + | | [[Image:FL63ACNS0004.png|130px]] |
| − | | [[Image:FL63ACNS0003.png| | + | | [[Image:FL63ACNS0003.png|130px]] |
|- | |- | ||
! Name | ! Name | ||
| Line 32: | Line 32: | ||
! 3-Hydroxyl stereo | ! 3-Hydroxyl stereo | ||
| ↑ || ↓ || ↓ || ↑ | | ↑ || ↓ || ↓ || ↑ | ||
| + | |- | ||
| + | ! Afzelechins | ||
| + | | [[FL63AANS0001|(+)-Afzelechin]] | ||
| + | | [[FL63AANS0002|(-)-Epiafzelechin]] | ||
| + | | | ||
| + | | [[FL63AANS0003|ent-Epiafzelechin]] | ||
|- | |- | ||
! Gallocatechins | ! Gallocatechins | ||
| [[FL63AGNS0002|(+)-Gallocatechin]] | | [[FL63AGNS0002|(+)-Gallocatechin]] | ||
| [[FL63AGNS0003|(-)-Epigallocatechin]] | | [[FL63AGNS0003|(-)-Epigallocatechin]] | ||
| − | | [[FL63AGNS0017| | + | | [[FL63AGNS0017|ent-Gallocatechin]] |
| − | | | + | | |
|} | |} | ||
Latest revision as of 11:58, 19 August 2010
Catechins refer to a subgroup of flavan 3-ol derivatives (FL63AC). The two chiral center at C2 and C3 of the flavan 3-ols produces 4 isomers, and (+)-Catechin and its stereoisomer (-)-Epicatechin are naturally abundant. Less abundant are (-)-Catechin and (+)-Epicatechin.
- afzelechin ... catechin minus 1 hydroxyl group in ring B
- gallocatechin ... catechin plus 1 hydroxyl group in ring B
| Structure | 
|
|
|
|
|---|---|---|---|---|
| Name | (+)-Catechin or D-Catechin |
(-)-Epicatechin or L-Epicatechin |
ent-Catechin or (-)-Catechin |
ent-Epicatechin or (+)-Epicatechin |
| B-ring stereo | ↓ | ↓ | ↑ | ↑ |
| 3-Hydroxyl stereo | ↑ | ↓ | ↓ | ↑ |
| Afzelechins | (+)-Afzelechin | (-)-Epiafzelechin | ent-Epiafzelechin | |
| Gallocatechins | (+)-Gallocatechin | (-)-Epigallocatechin | ent-Gallocatechin |
Among the stereoisomers, the bioavailability in human follows the order:
| (-)-epicatechin | > | (+)-catechin | = | (+)-epicatechin | > | (-)-catechin |
The circulation level of (-)-epicatechin is 6 times higher than that of (-)-catechin. Naturally abundant species are more bioavailable than less abundant ones.
