Acacia concinna Saponins. II. Structures of Monoterpenoid Glycosides in the Alkaline Hydrolysate of the Saponin Fraction.

An antitumor compound julibroside J28 from Albizia julibrissin

“…A comparison of the 13 C NMR data of 1 with those of 2 showed that the signal of C-5 and C-10 of 1 underwent an upfield shift of 2.1 ppm and a downfield shift of 1.1 ppm, respectively. The above differences between two saponins were quite similar to the 13 C NMR data of (6R)-menthiafolic acid-6-O-b-D D-quinovoside (4) and (6S)-menthiafolic acid-6-O-b-D D-quinovoside (5) 4 (see Fig. 1), which revealed the configurations of the two monoterpene moieties were C-6 (S) and C-6 (R), respectively.…”

Isolation and anti-HIV-1 integrase activity of lentzeosides A–F from extremotolerant lentzea sp. H45, a strain isolated from a high-altitude Atacama Desert soil

“…The COSY spectrum indicated a second spin system which included the signals H-1′ to H 3 -6′, which in combination with the HMBC correlation of H-1′/C-5′ suggested a β-L-quinovopyranose (β-L-6-deoxyglucopyranose), which was confirmed by the optical rotation, the coupling constant of the anomeric proton (J = 7.8 Hz), axial-axial proton couplings for H1′/H2′, H2′/H3′, H3′/H4′ and H4′/H5′ (Table 2) as well as the agreement of the 13 C NMR data and the ROESY correlations with reported data. 21 The sugar moiety was further confirmed by acid hydrolysis of 1 upon which α-L-quinovose was detected by co-chromatography on TLC in comparison with authentic sugar samples. Finally, the connectivity of the two substructures was confirmed by the HMBC correlation of H-1′/C-1.…”

Kinmoonosides A−C, Three New Cytotoxic Saponins from the Fruits of Acacia concinna, a Medicinal Plant Collected in Myanmar

“…To elucidate the structures of the genuine saponins, we first conducted the alkaline hydrolysis of the crude saponin fraction of A. concinna and obtained four monoterpenoids (5)(6)(7)(8) and five prosapogenins (9)(10)(11)(12)(13), while acid hydrolysis of the alkaline hydrolysate gave acacic acid lactone (14) 5 ( Figure 1). By analysis of their spectral data and comparison with literature values, monoterpenoids 5-7 were determined to be known compounds, namely, menthiafolic acid (5), 7 a mixture (1:1) of (6S)-and (6R)-menthiafolic acid 6-O--D-quinovopyranoside (6), 7 and a mixture (2:1) of two diastereomers of 3,6-epoxy-2-hydroxymethyl-6-methyl-7-octenoic acid (7), 11 while prosapogenins 11-13 were identified as 3-O--D-xylopyranosyl(1f2)-R-L-fucopyranosyl(1f6)- [ -D-glucopyranosyl(1f2)]--D-glucopyranoside (11); 12 acacic acid 3-O--D-xylopyranosyl(1f2)-R-L-arabinopyranosyl-(1f6)-2-acetamido-2-deoxy--D-glucopyranoside (12); 13 and acacic acid lactone 3-O--D-xylopyranosyl(1f2)-R-L-arabinopyranosyl(1f6)-[ -D-glucopyranosyl(1f2)]--D-glucopyranoside (13, concinnoside F ) albiziasaponin C), 5,14 respectively.…”