Internal and external flavonoids from the leaves of Japanese Chrysanthemum species (Asteraceae)

Flavonoids in the leaves of 17 species and 4 varieties of Japanese Chrysanthemum were surveyed. Nine flavonoid glycosides were isolated and identified as quercetin 3- O-rutinoside, eriodictyol 7- O-glucuronide, luteolin 7- O-rutinoside, 7- O-glucoside and 7- O-glucuronide, apigenin 7- O-glucoside and 7- O-glucuronide, chrysoeriol 7- O-glucuronide and acacetin 7- O-rutinoside. The taxa were divided into three chemotypes by their flavonoid characters, i.e. I) occurrence of flavone, flavonol and flavanone, II) occurrence of flavone and flavanone and III) occurrence of flavone alone. The chemotypes almost agreed with the system based on morphological, cytological and geographical characters, i.e. Group I) the taxa growing on seashore and having tubular flowers alone, Group III) the taxa of the Asian Continent origins and having both tubular and ligulate flowers. Others were included in Group II which was subdivided into four groups by flavonoid characters. Twelve external flavonoids were isolated and identified as acacetin 7- O-rutinoside, luteolin, nepetin, 5,7,3',4'-tetrahydroxy-6,5'-dimethoxyflavone, apigenin, hispidulin, 5,7,4'-trihydroxy-6,3',5'-trimethoxyflavone, jaceosidin, sudachitin, eupatilin, hymenoxin and pectolinarigenin. The distribution patterns of almost all external flavonoids were apparently irregular among the taxa.