FL63ACNS0001

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Upper classes : FL Flavonoid : FL6 Flavan : FL63 Flavan 3-ol :  FL63AC Catechin and Epicatechin (75 pages) :  FL63ACNS Simple substitution (24 pages)

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

いわゆるカテキン類とは、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 (+)-カテキン とその立体異性体である (-)-エピカテキン です。 (-)-カテキン と (+)-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

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:

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。

(-)-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.

(-)-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。

IDs and Links
LipidBank	[1]
LipidMaps	[2]
CAS	154-23-4
KEGG	{{{KEGG}}}
KNApSAcK	C00000947
CDX file
MOL file	FL63ACNS0001.mol

(+) -Catechin
Structural Information
Systematic Name	(+) -3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol
Common Name	(+) -Catechin D-Catechin D-Catechol Dexcyanidanol Teafuran 30A
Symbol
Formula	C15H14O6
Exact Mass	290.07903818
Average Mass	290.26806
SMILES	Oc(c3)cc(O1)c(c(O)3)CC([H])(O)C([H])1c(c2)cc(O)c(O)c2
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Reflactive Index
Solubility
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra
Chromatograms

Species Information

Species-Flavonoid Relationship Reported

Species ID Metabolite Name Reference Arabidopsis thaliana FL63ACNS0001 See above. Abrahams_S et al. 2002 Quercus robur FL63ACNS0001 See above. Feeny_P et al. 1988 Quercus robur FL63ACNS0001 See above. Feeny_PP et al. 1968 Acacia catechu FL63ACNS0001 See above. Hardegger_E et al. 1957 Chamaerops humilis FL63ACNS0001 See above. Hardegger_E et al. 1957 Cinnamomum sieboldii FL63ACNS0001 See above. Hardegger_E et al. 1957 Cistus salviifolius FL63ACNS0001 See above. Hardegger_E et al. 1957 Eucalyptus camaldulensis FL63ACNS0001 See above. Hardegger_E et al. 1957 Ginkgo biloba FL63ACNS0001 See above. Hardegger_E et al. 1957 Liquidambar styraciflua FL63ACNS0001 See above. Hardegger_E et al. 1957 Rosa cymosa FL63ACNS0001 See above. Hardegger_E et al. 1957 Vaccinium vitis-idaea FL63ACNS0001 See above. Hardegger_E et al. 1957 Vitis vinifera FL63ACNS0001 See above. Hardegger_E et al. 1957 Salix caprea FL63ACNS0001 See above. Malterud_KE et al. 1985 Acacia catechu FL63ACNS0001 See above. Perkin_AG et al. 1902 Chamaerops humilis FL63ACNS0001 See above. Perkin_AG et al. 1902 Cinnamomum sieboldii FL63ACNS0001 See above. Perkin_AG et al. 1902 Cistus salviifolius FL63ACNS0001 See above. Perkin_AG et al. 1902 Eucalyptus camaldulensis FL63ACNS0001 See above. Perkin_AG et al. 1902 Ginkgo biloba FL63ACNS0001 See above. Perkin_AG et al. 1902 Liquidambar styraciflua FL63ACNS0001 See above. Perkin_AG et al. 1902 Rosa cymosa FL63ACNS0001 See above. Perkin_AG et al. 1902 Vaccinium vitis-idaea FL63ACNS0001 See above. Perkin_AG et al. 1902 Vitis vinifera FL63ACNS0001 See above. Perkin_AG et al. 1902