Puerins A and B, Two New 8-C Substituted Flavan-3-ols from Pu-er Tea

Pu-er tea is a special treated fermented tea produced from crude green tea, which is prepared from the leaves of Camellia sinensis var. assamica. It is a traditional beverage having been used in China, particularly the southern areas, for a long time. Chemical investigation led to the identification of two new 8-C substituted flavan-3-ols, puerins A (1) and B (2), and two known cinchonain-type phenols, epicatechin-[7,8-bc]-4alpha-(4-hydroxyphenyl)-dihydro-2(3H)-pyranone (3) and cinchonain Ib (4), together with other seven known phenolic compounds, 2,2',6,6'-tetrahydroxydiphenyl (5), (-)-epicatechin-8-C-beta-d-glucopyranoside (6), (-)-epicatechin (EC) (7), (-)-epigallocatechin (EGC) (8), (+/-)-gallocatechin (GC) (9), gallic acid (10), and myricetin (11), in addition to caffeine (12). Their structures were determined by spectroscopic methods. The compounds 1-5, which might be formed in the postfermentative process of Pu-er tea, were isolated from tea and theaceous plants for the first time.