Triterpene glycosides from the roots of Codonopsis lanceolata.
In the course of the development of new designer foods using the roots of Codonopsis lanceolata, we found that hot-water extracts of C. lanceolata recovered decreased testosterone levels in the blood and accelerated the restoration of reproductive dysfunction induced by hyperthermic treatment in male mice. Thus we studied the constituents of the polar fraction of the roots of C. lanceolata and identified six new triterpene saponins, lancemasides B (2), C (3), D (4), E (5), F (6), and G (7), along with the known saponin lancemasaide A (1) and phenylpropanoid glycosides 8-10. The structures of the new compounds 2-7 were determined by means of spectral data including 2D-NMR studies and chemical reactions to be oleanan-type bisdesmoside with sugars at C-3 and C-28. Compounds 2-6 have echinocystic acid as an aglycone, and compound 7 has asterogenic acid as an aglycone. Identification of the sugars and determination of their D,L-chiralities were carried out by application of the exciton chirality method to the per-O-p-bromobenzoylmethyl sugar derived from saponins.
Ushijima
Mitsuyasu
M
Healthcare Research Institute, Wakunaga Pharmaceutical Co., Ltd, 1624 Shimokotachi, Koda-cho, Akitakata, Hiroshima 739-1195, Japan.
Komoto
Noriko
N
Sugizono
Yoshimi
Y
Mizuno
Ikuko
I
Sumihiro
Masanori
M
Ichikawa
Makoto
M
Hayama
Minoru
M
Kawahara
Nobuo
N
Nakane
Takahisa
T
Shirota
Osamu
O
Sekita
Setsuko
S
Kuroyanagi
Masanori
M
D002236:Carbohydrate Conformation; D029745:Codonopsis / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D006868:Hydrolysis; D007723:Korea; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018517:Plant Roots / Q000737:chemistry; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification
D006027:Glycosides; D012503:Saponins; D014315:Triterpenes