Triterpenoid glycosides from the roots of Tetrapanax papyriferum K. Koch. III. Structures of four new saponins.

Mediation of the Cytotoxicity of Lanostanoids and Steroids of Ganoderma tsugae through Apoptosis and Cell Cycle

“…The signal at δ 4.64 that was shifted to δ 3.43 after alkaline hydrolysis, as observed in related lanostanoid-type compounds, was assigned to the methine group bearing the α-acetoxy group at C-3 . In addition to the above evidence, the absence of two secondary methyl signals and the presence of an anomeric proton signal at 5.47 (d, J = 8.0 Hz) in the 1 H NMR spectrum of 1 and a tertiary carbon signal at δ 125.0, four-quarternary carbon signals at δ 133.0, 135.2, 136.2, and 177.4, and six glucosyl carbon signals at δ 95.8, 78.7, 78.4, 73.9, 71.3, and 62.2 in the 13 C NMR spectrum of 1 clearly indicated that 1 was a 3α-acetoxy-5α-lanosta-8,24-dien-21-oic acid ester β- d -glucoside ( 1 ) . On alkaline hydrolysis, it gave glucose, detected by TLC, and 3α-hydroxy-5α-lanosta-8,24-dien-21-oic acid, identified by comparison with an authentic sample .…”

“…4 In addition to the above evidence, the absence of two secondary methyl signals and the presence of an anomeric proton signal at 5.47 (d, J ) 8.0 Hz) in the 1 H NMR spectrum of 1 5 and a tertiary carbon signal at δ 125.0, four-quarternary carbon signals at δ 133.0, 135.2, 136.2, and 177.4, and six glucosyl carbon signals at δ 95.8, 78.7, 78.4, 73.9, 71.3, and 62.2 in the 13 C NMR spectrum of 1 clearly indicated that 1 was a 3R-acetoxy-5R-lanosta-8,24-dien-21-oic acid ester β-D-glucoside (1). 6 On alkaline hydrolysis, it gave glucose, detected by TLC, and 3Rhydroxy-5R-lanosta-8,24-dien-21-oic acid, identified by comparison with an authentic sample. 2 The 13 C NMR spectrum of 1 (Table 1) was assigned by comparison with those of the corresponding data for 3 and methyl β-D-glucopyranoside.…”

A New Monodesmosidic Triterpenoid Saponin from the Seeds of Vigna unguiculata subsp. unguiculata

“…The upfield shifts of C-3 ( -0.8, -1.2) and C-5 (-1.0, -2.2) of the glucuronic acid and galactose units also supported the (1 -»4) linkage of these sugar moieties (9,10). The (1->4) linkage of galactose to glucuronic acid was supported by comparing the 13C-nmr literature data for similarly linked sugar moieties (11)(12)(13).…”

“…The 2D COSY-45°e xperiment was carried out at 400. 13 MHz with a sweep width of4065 Hz (IK data points in o>2)and 2032 Hz (2561, values IK)…”

“…The 2D 'H-13C heteronuclear multiple quantum coherence (HMQC) experiment was carried out at 500. 13 MHz with a sweep width of 4201.68 Hz (2K data points in 2) and 180.703 Hz (256 t, values zero filling 512) in A 1.0-sec relaxation delay was used and 64 transients were performed for each t, value. In the HMQC experiment interpulse delays were optimized for a Jen of 0.0040 Hz [D20=(l/2J)XHJ=135 Hz].…”