5, 128.2, 128.5, 128.6, 130.1 × 2, 132.1), a terminal methyl (δC 14.3), and eight methylene (δC 20.7, 25.0, 25.9, 25.9,

27.2, 28.9, 29.4, 34.2) carbon signals were observed indicating that Compound 1 contains a hexadecatrienoic acid as a fatty acid moiety. The Bortezomib datasheet fatty acid methyl ester obtained by alkaline hydrolysis, methyl esterification, and solvent fractionation appeared as a clear peak at 13′86″ on the GC/MS spectrum, which was identified as 7(Z),10(Z),13(Z)-hexadecatrienoic acid methyl ester by comparing the mass spectrum of the peak with that of the library (Wiley Library, version 2008). In the gradient heteronuclear multiple-bond correlation (gHMBC) spectrum, long-range correlations were observed between the oxygenated methylene proton signal of glycerol H-1 (δH 4.46) and the ester carbonyl carbon signal C-1″ (δC 173.4), and between the anomeric proton signal H-1 (δH 4.83) and the oxygenated methine carbon signal of glycerol Sirolimus ic50 C-3 (δC 72.2), indicating that the fatty acid and the galactose moieties were linked to the hydroxyls of C-1 and C-3 of glycerol, respectively. Therefore, the chemical structure of Compound 1 was determined to be (2S)-1-O-7(Z),10(Z),13(Z)-hexadecatrienoyl-3-O-β-d-galactopyranosyl-sn-glycerol, named as panaxcerol A ( Fig. 1) [19]. Detection of Compound 2 involved spraying the plate with 10% sulfuric acid followed by heating. Formation of a dark purple color confirms the presence of Compound

2. The molecular weight was ID-8 determined to be from the molecule ion peak m/z 515 [M+H]+ in the positive FAB/MS. Compound 2 showed absorbance bands due to the hydroxyl (3,364 cm−1), carbonyl (1,730 cm−1), and double bond (1,585 cm−1) groups in the IR spectrum. The 1H-NMR and 13C NMR spectra of Compound 2 were very similar to that of Compound 1 with the exception of the number of methylene units. The 1H-NMR showed six olefinic proton signals at δH 5.39–5.46, a terminal methyl proton signal at δH 0.90, and several methylene proton signals at δH 1.19–2.89 due to an unsaturated fatty acid with three double bonds. A hemiacetal proton signal at δH 4.82 (d, J = 7.6 Hz), several oxygenated methine and methylene proton

signals at δH 4.01–4.52 due to a sugar moiety, an oxygenated methine proton signal at δH 4.43 (H-2), and two oxygenated methylene proton signals at δH 4.48 (H-1), δH 4.31 (H-3b), and δH 4.05 (H-3a) due to a glycerol moiety were observed. The 13C-NMR spectrum showed hexose carbon signals at δC 105.8, 77.0, 75.2, 72.5. 69.0, and 62.3 owing to a β-galactopyranose derivative and three oxygenated carbon signals at δC 72.1, 70.1, and 66.5 of a glycerol, indicating that Compound 2 was a monogalactosyl monoacylglyceride. An ester carbonyl (δC 173.5), six olefin methine (δC 127.5, 128.0, 128.6, 128.6, 130.5 × 2, 132.0), a terminal methyl (δC 14.5), and 10 methylene (δC 20.8, 25.1, 25.8, 25.9, 27.4, 29.2, 29.2, 29.3, 29.8, 34.2) carbon signals were observed indicating that the fatty acid was an octadecatrienoic acid.