The MeOH extract from dried whole Botrychium ternatum plants yielded 33 compounds, including seventeen new flavonoid glycosides and sixteen known compounds. The structures of new compounds were established using NMR spectroscopic analysis and chemical evidence.Key words Botrychium ternatum; Ophiolossaceae; flavonoid glycoside; kaempferol; ternatumoside Recently, plants in the Ophiolossaceaus family were reported to be effective in the cosmetic field, for example, skin moisturizing and lightning actions, improvement and protection of rough skin, and proliferation of skin fibroblasts.
1,2)Botrychium ternatum is one of the Ophiolossaceaus plants and distributed to the Honshu, Shikoku, and Kyushu Islands in Japan, the Korean Peninsula, and China. In Japan, this plant is called "Fuyunohanawarabi" and used to treat dizziness, headache, cough, and fever as a folk medicine. In the course of research to find the efficient agents in the cosmetic field from the Ophiolossaceaus family, we investigated the constituents of B. ternatum and their biological activities.A MeOH extract from dried whole B. ternatum plants was suspended in water. The suspension was extracted with diethyl ether and partitioned into an ether-soluble fraction and a H 2 Osoluble fraction. The ether-soluble fraction was then separated into a n-hexane-soluble fraction and a MeOH-H 2 O (9 : 1)-soluble fraction. The residue of the water soluble-fraction and the MeOH-H 2 O (9 : 1)-soluble fraction was subjected to both silica gel column chromatography and semi-preparative HPLC to give thirty flavonoid glycosides (1-30), two flavonoids (31, 32), and a bibenzyl derivative (33 The molecular formulae of ternatumosides III (8) and IV (9) were identified as C 42 H 46 O 22 and C 51 H 52 O 24 , respectively, by HR-FAB-MS. The NMR spectroscopic data for 8 and 9 were similar to those of 7, and signals due to one and two sets of (trans)-p-coumaroyl groups were observed in 8 and 9, respectively. Additionally, both compounds yielded 7 and (trans)-p-coumaric acid by alkaline hydrolysis.