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

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.

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 Salix caprea FL63ACNS0001 See above. Harborne 1999 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 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