Chalcones and other flavonoids from Asarum sensu lato (Aristolochiaceae)

• Published in: Biochemical systematics and ecology Vol. 33; no. 6; pp. 571 - 584
• Main Authors: Iwashina, Tsukasa, Kitajima, Junichi, Shiuchi, Toshiaki, Itou, Yutaka
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.06.2005
• Subjects: Aristolochiaceae; Asarum; Asarum sensu lato; Aurone; Chalcones; Chalcononaringenin 4,2′,4′-tri- O-glucoside; chemical constituents of plants; Chemotaxonomy; Flavonoids; Chalcones; Flavonoids; Asarum sensu lato; Chalcononaringenin 4,2′,4′-tri- O-glucoside; Chemotaxonomy; Aurone; Aristolochiaceae
• ISSN: 0305-1978; 1873-2925
• DOI: 10.1016/j.bse.2004.12.005

Seventy-five taxa belonging to the genus Asarum sensu lato were studied for their composition of flavonoids. Three chalcones and an aurone were found as major components. The chalcones were identified as chalcononaringenin 2′,4′-di- O-glucoside, 4,2′,4′-tri- O-glucoside, 4- O-glucoside, and the aurone as aureisidin 4,6-di- O-glucoside. The glycoside, 2′,4′-di- O-glucoside was detected in all taxa examined, and is a chemotaxonomical feature of Asarum sensu lato. 4,2′,4′-Tri- O-glucoside was found from the taxa classified into the genera Asiasarum, Geotaenium and Heterotropa by Maekawa's system. On the other hand, the glycoside was not detected from three Asarum sensu stricto species, A. caudigerum, A. caulescens and A. leptophyllum. In contrast, aurone, aureusidin 4,6-di- O-glucoside occurred in two Asarum s.s., A. caulescens and A. leptophyllum. Thus, the Asarum s.s. and other Maekawa's genera, Asiasarum, Geotaenium and Heterotropa could distinguish by the presence or absence of some anthochlor pigments. Other flavonoids were isolated from the selected 18 Asarum species. They were characterized as some flavonol 3- or 3,7- O-glycosides based on kaempferol, quercetin and isorhamnetin, flavone, apigenin 6,8-di- C-glycoside, flavanone, naringenin 5,7-di- O-glucoside, and xanthone, mangiferin.