Oleanane-type glycosides from Pittosporum tenuifolium “variegatum” and P. tenuifolium “gold star”

Triterpenoid Saponins from the Cultivar “Green Elf” of Pittosporum tenuifolium

“…The assignments of their position were determined by HMBC cross-peaks at δ H /δ C 1.19 (H 3 -23)/90.3 (C-3), 3). On the basis of all these conclusions, the aglycone of 1 was identified as (3β,16α,21β,22α)-3,16,21,22,28-pentol-olean-12-ene, named barringtogenol C, in full agreement with literature data [5].…”

“…This was confirmed by th cross-peaks at δH/δC 6.40 (H-21)/168.8 (Ang-1) and δH/δC 4.26 (H2-28)/171.0 (Ac-1 C-21 position, the substituent was composed of two vinylic methyl groups at 2.0 2.07 (d, J = 6.7 Hz) ppm, which correlated in the HMBC spectrum with one ethyle ternary carbon at 129.0 and an ethylenic methine carbon at 136.2 ppm. These data an angeloyl group acylating the C-21 position (Table 1) [5] The deshielded chemical shift of CH-21 at δC/δH 81.0/6.40 ppm and CH2-28 66.2/4.26 ppm suggested an acylation at these positions. This was confirmed by the cross-peaks at δH/δC 6.40 (H-21)/168.8 (Ang-1) and δH/δC 4.26 (H2-28)/171.0 (Ac-1) C-21 position, the substituent was composed of two vinylic methyl groups at 2.01 2.07 (d, J = 6.7 Hz) ppm, which correlated in the HMBC spectrum with one ethyle ternary carbon at 129.0 and an ethylenic methine carbon at 136.2 ppm.…”

“…Moreover, several cultivars of this species are sold in greenhouses for garden use. Thus, as a continuation of our study on the glycosylated derivatives from the Pittosporum genus [5][6][7], we investigated the phytochemical interest of the "Green Elf" cultivar of P. tenuifolium. In the present paper, we report the isolation and structural elucidation of two undescribed triterpene saponins (Figure 1), together with a known one from the leaves and a known one from the roots.…”

Amyloid β aggregation inhibitory activity of triterpene saponins from the cactus Stenocereus pruinosus

“…The structure of 1 has chichipegenin as the aglycone, in which C-3 and C-22 are glycosylated. Although saponins that have a sugar unit at C-22 to some extent have been identified [32][33][34], this is the first report in the case of chichipegenin. Compounds 2-3 and 4 have longispinogenin or erythrodiol as the aglycone moiety.…”

Three New Oleanane-Type Triterpenoidal Glycosides from Impatiens balsamina and Their Biological Activity

“…The 1 H NMR spectrum of 1 showed a broad singlet at δH 5.30 for an olefinic proton, overlapped signals from δH 3.20 to 4.38 for oxygenated methine/methylene protons, seven singlets at δH 1.40, 1.09, 1.05, 1.00, 0.97, 0.93, and 0.88 for methyl protons, and the others in the region from δH 2.28 to 0.82. Among a total of 41 carbons present in this molecule, 40 resonances were observed in the 13 C NMR spectrum of 1, including 30 peaks for typical oleanane-type triterpenoids [14][15][16][17][18] with two olefinic carbons at δC 144.6 and 124.2 and four oxygenated carbons at δC 91.1, 78.8, 70.4, and 65.8, and ten peaks for β-glucuronic acid (δC 106.9, 75.6, 78.1, 73.8, and 76.8) and β-xylopyranose (δC 102.8, 74.5, 77.0, 71.2 and 66.5). These 1 H and 13 C NMR data implied that 1 is an oleanane-type triterpenoidal glycoside with two sugar moieties, and its core structure including the location of a double bond and four oxygenated carbons was established through analysis of the Distortionless Enhancement by Polarization Transfer (DEPT), correlation spectroscopy (COSY), Heteronuclear Single Quantum Correlation (HSQC), and Heteronuclear Multiple Bond Correlation (HMBC) spectra (Figure 2, Supplementary materials).…”