Fructose-derived carbohydrates fromAlisma orientalis

Abstract

Nine fructose-derived carbohydrates were obtained from the methanol extract from the rhizome of Alisma orientalis. On the basis of spectroscopic analysis, their structures were determined to be alpha-D-fructofuranose (1), beta-D-fructofuranose (2), ethyl alpha-D-fructofuranoside (3), ethyl beta-D-fructofuranoside (4), 5-hydroxymethyl-furaldehyde (5), sucrose (6), raffinose (7), stachyose (8) and verbascose (9), along with two oligosaccharides of manninotriose (10) and verbascotetraose (11). Compounds 3, 4 and 7-11 were isolated from this plant for the first time. A hypothetical biosynthesis pathway among these isolated carbohydrates (1-11) was briefly introduced.

Anti-Food Allergic Compounds from Penicillium griseofulvum MCCC 3A00225, a Deep-Sea-Derived Fungus

“…By comparison of the NMR and MS data with those published in the literatures, 26 known compounds were determined to be aurantiomide C (11) [14], cyclopenin (12) [19], (−)-cyclopenol ( 13) [20], (3S)-1,4-benzodiazepine-2,5-diones ( 14) [21], 3-benzylidene-3,4dihydro-4-methyl-lH-l,4-benzodiazepine-2,5-dione ( 15) [22], 3-methyl-3,4-dihydroquinazo line-4-one ( 16) [23], 1,2-dihydro-2,3-dimethyl4(3H)quinazolinone ( 17) [24], N,N'-1,2-pheny lenebis-acetamide ( 18) [25], aconicarpyrazine B ( 19) [26], pyroglutamylleucinmethylester (20) 29) [32], methyl phydroxybenzeneacetate (30) [33], 2-hydroxy phenyl acetic acid (31) [34], methyl homogentisate (32) [35], 5-hydroxymethyl-furaldehyde (33) [36], leptosphaerone A (34) [37], 3-methyl-2-penten-5-olide (35) [38], and (R)-mevalonolactone (36) [39].…”

Four New Glycosides from the Rhizoma of Anemarrhena asphodeloides

“…Combined with the Distortionless Enhancement by Polarization Transfer (DEPT), the 13 C-NMR spectrum of compound 3 showed 12 signals, in two groups of fructofuranosyl at δ C 98.8, 81.8, 77.7, 83.5, 61.2, and 61.7, and δ C 62.5, 102.5, 76.9, 74.5, 81.2 and 62.6. The α-configuration of fructofuranosyl was determined by the chemical shift of C-3 (δ C 81.8) and C-5 (δ C 83.5), and the β-configuration of fructofuranosyl was determined by the chemical shift of C-5′ (δ C 81.2) based on the literature [ 9 ]. The connectivity of the two fructofuranosyls was mainly established on the HMBC correlation of H-3 (δ H 3.94, d, J = 2.4 Hz) with C-2′ (δ C 102.5) ( Figure 2 ), which suggested the attachment position of β-fructofuranosyl at C-2 of α-fructofuranosyl.…”

New Methyl Threonolactones and Pyroglutamates of Spilanthes acmella (L.) L. and Their Bone Formation Activities

“…The 13 C-NMR also showed two secondary carbons at δC 60.6 and 62.9; three tertiary carbons at δC 79.0, 82.6, and 84.7; and a quaternary carbon at δC 109.2, indicating a fructofuranose moiety. Zhang et al (2009) described that α and β orientations of D-fructofuranose were distinguishable by the J value of H-3 and the chemical shift of C-2. The characteristic values of α orientation are 3 JH3,H4 = 3-4 Hz and C-2 (δC 107-109), while the β orientation is 3 JH3,H4 = 7-9 Hz and C-2 (δC 103-106) [27], which suggested the α-fructofuranosylation to the aglycone.…”