Isoeichlerianic acid from Aglaia silvestris and revision of the stereochemistry of foveolin B

New triterpenoid saponins from the leaves of Cyclocarya paliurus

“…This result suggested that the glycosyl was located at C-12. The relative configurations at C-12 and C-20 were determined by NOESY correlations between H-12 and H-30, H-21 and H-13, the absolute configurations at C-12 and C-20 were determined to be R and S, respectively, on the basis of comparison to the 13 C NMR chemical Table 1 NMR spectroscopic data (acetone-d 6 ) for cyclocarioside I (1), cyclocarioside J (2) and cyclocarioside K (3 shift and optical rotation data for analogous 3,4-secodammaranes [6,16]. Ultimately, the structure of 1 was deduced as (23E)-(12R, 20S)-12,20-dihydroxy-3, 4-secodammara-4(28), 23, 25-trien-3-oic acid-12-O-a-L-arabinopyranoside, and named cyclocarioside I. Cyclocarioside J (2) has the molecular formula C 35 H 58 O 9 , as determined by HR-ESI-MS analysis (m/z 645.3981 [M+Na] + ).…”

“…3). The absolute configuration at C-24 was determined to be S, on the basis of comparison to the 13 C NMR chemical shift and optical rotation data for analogous 3,4-secodammaranes [6,16]. Thus the structure of 2 was determined to be (12R, 20S, 24S)-20, 24-dihydroxy-3, 4-secodammara-2(28), 25-dien-3-oic acid-12-O-a-L-arabinopyranoside, named cyclocarioside J.…”

“…The relative configurations at C-3, C-12, C-20, C-24 were determined by NOESY correlations between H-3 and H-29, H-12 and H-30, H-21 and H-30, H-24 and H-21. The absolute configurations at C-20 and C-24 were determined to be S and R, respectively, on the basis of comparison to the 13 C NMR chemical shift for analogous epoxydammaranes [16]. Therefore, the structure of 3 was deduced as (20S, 24R)-(3a, 12b)-20,24-epoxydammara-25-ol-12-O-b-Dquinovopyranosyl-3-O-a-L-arabinopyranoside, and 3 was named cyclocarioside K.…”

Triterpenoids and Sterones from the Stem Bark of Ailanthus altissima

“…Known compounds were identified as (4,4,14-trimethyl-3-oxo-24-nor-5α,13α,14β,17α,20S-chol-7-en-23-oic acid) (3), 16 hydroxydammarenone I (4), 17 ocotillone (5), 18 stigmasta-4-ene-3-one (6), 19 stigmasta-4,6,8(14),22-tetraen-3-one (7), 20 artelin (8), 21 polystachyol (9), 22 coniferyl alcohol (10), ferulic acid (11), 2,6-dimethoxyhydroquinone (12), antiarol (13), and 4-hydroxybenzaldehyde (14) by comparison with published literature data or direct identification by spectroscopic evidences. It was noted that compound 3 has been synthesized previously, 16 however, it was isolated from natural sources for the first time.…”

Molluscicidal activity of Aglaia duperreana and the constituents of its twigs and leaves

“…1). The known isolates were identified as betulinic acid (2) [16], 24(R),25-dihydroxydammar-20-en-3-one (3) [17], ursolic acid (4) [18], obtusilin (5) [19], (24R)-cycloartane-3α,24,25-triol (6) [20], cabraleone (7) [21], ocotillone (8) [21], shoreic acid (9) [21], 3-hydroxy-4',5,7-trimethoxyflavone (10) [22], 2,3-dihydro-5-hydroxy-4',7-dimethoxyflavone (11) [23], naringenin trimethyl ether (12) [24], (2R,3R)-(+)-4',5,7-trimethoxydihydroflavonol (13) [25], (+)-eudesmin (14) [26], (+)-odorine (15) [27], and (+)-odorinol (16) [27]. The identification was based on the interpretation of their spectroscopic data and by comparison with reported data.…”