Doc:FL63AC
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(New page: {{Twocolumn| Catechins refer to a subgroup of Flavan 3-ol derivatives (FL63AC). In a stricter sense, it means (+)-Catechin and its stereoisomer [[FL63A...) |
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{{Twocolumn| | {{Twocolumn| | ||
| − | Catechins refer to a subgroup of [[:Category:FL63| | + | Catechins refer to a subgroup of [[:Category:FL63|flavan 3-ol]] derivatives (FL63AC). |
| − | [[FL63ACNS0002|(-)-Epicatechin]]. | + | The two chiral center at C2 and C3 of the flavan 3-ols produces 4 isomers, |
| + | and [[FL63ACNS0001|(+)-Catechin]] and its stereoisomer | ||
| + | [[FL63ACNS0002|(-)-Epicatechin]] are naturally abundant. Less abundant are [[FL63ACNS0004|(-)-Catechin]] and [[FL63ACNS0003|(+)-Epicatechin]]. | ||
| + | * afzelechin ... catechin minus 1 hydroxyl group in ring B | ||
| + | * gallocatechin ... catechin plus 1 hydroxyl group in ring B | ||
| | | | ||
| − | いわゆるカテキン類とは、[[:Category:FL63|Flavan 3-ol]] | + | いわゆるカテキン類とは、[[:Category:FL63|Flavan 3-ol]]の下にあるグループを指します。C2, C3位にある不斉炭素によって4つの異性体が作られますが、自然界に豊富なのは [[FL63ACNS0001|(+)-カテキン]] とその立体異性体である |
| − | [[FL63ACNS0002|(-)- | + | [[FL63ACNS0002|(-)-エピカテキン]] です。 [[FL63ACNS0004|(-)-カテキン]] と [[FL63ACNS0003|(+)-エピカテキン]] は自然界にあまりみられません。 |
| + | * アフゼレキン ... カテキンのB環から水酸基を一つ除いたもの | ||
| + | * ガロカテキン ... カテキンのB環に水酸基を一つ追加したもの | ||
}} | }} | ||
| − | {| style="text-align:center" | + | {| class="wikitable" style="text-align:center" |
|- | |- | ||
| − | + | ! 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 | |
| − | | [[FL63ACNS0001|(+)-Catechin]] | + | | [[FL63ACNS0001|(+)-Catechin or<br/>D-Catechin]] |
| [[FL63ACNS0002|(-)-Epicatechin or<br/> L-Epicatechin]] | | [[FL63ACNS0002|(-)-Epicatechin or<br/> L-Epicatechin]] | ||
| [[FL63ACNS0004|ent-Catechin or<br/> (-)-Catechin]] | | [[FL63ACNS0004|ent-Catechin or<br/> (-)-Catechin]] | ||
| [[FL63ACNS0003|ent-Epicatechin or<br/> (+)-Epicatechin]] | | [[FL63ACNS0003|ent-Epicatechin or<br/> (+)-Epicatechin]] | ||
|- | |- | ||
| − | + | ! B-ring stereo | |
| ↓ || ↓ || ↑ || ↑ | | ↓ || ↓ || ↑ || ↑ | ||
|- | |- | ||
| − | + | ! 3-Hydroxyl stereo | |
| ↑ || ↓ || ↓ || ↑ | | ↑ || ↓ || ↓ || ↑ | ||
|- | |- | ||
| − | | | + | ! Afzelechins |
| − | | | + | | [[FL63AANS0001|(+)-Afzelechin]] |
| + | | [[FL63AANS0002|(-)-Epiafzelechin]] | ||
| + | | | ||
| + | | [[FL63AANS0003|ent-Epiafzelechin]] | ||
| + | |- | ||
| + | ! Gallocatechins | ||
| + | | [[FL63AGNS0002|(+)-Gallocatechin]] | ||
| + | | [[FL63AGNS0003|(-)-Epigallocatechin]] | ||
| + | | [[FL63AGNS0017|ent-Gallocatechin]] | ||
| + | | | ||
|} | |} | ||
| + | |||
| + | {{Twocolumn| | ||
| + | Among the stereoisomers, the bioavailability in human follows the order: | ||
| + | | | ||
| + | 立体異性体の中で、ヒトにおける利用活性は以下の順番になります。 | ||
| + | }} | ||
| + | <center> | ||
| + | {| | ||
| + | | (-)-epicatechin ||>|| (+)-catechin ||=|| (+)-epicatechin ||>|| (-)-catechin | ||
| + | |} | ||
| + | </center> | ||
| + | {{Twocolumn| | ||
| + | The circulation level of (-)-epicatechin is 6 times higher than that of (-)-catechin. Naturally abundant species are more bioavailable than less abundant ones. | ||
| + | | | ||
| + | (-)-エピカテキンが体内に入る効率は(-)-カテキンの6倍にもなり、天然に多く産する分子種が多く吸収されることがわかります。 | ||
| + | }} | ||
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.
