34327-07-6

Usage

InChI:InChI=1/C9H18O6/c1-13-5-7(12)9(15-3)8(14-2)6(11)4-10/h4,6-9,11-12H,5H2,1-3H3/t6-,7+,8+,9+/m0/s1

Upstream product

• 2348-00-7 methyl 3,4,6-tri-O-methyl-β-D-glucopyranoside 
• 5596-21-4 methyl 2-O-(4-toluene)sulfonyl-α-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 39706-25-7 O³,O⁴,O⁶-Trimethyl-D-fructose 
• 7732-18-5 water 
• 144-62-7 oxalic acid 
• 911652-40-9 methyl-(O²-benzyl-O³-methyl-β-D-glucopyranoside) 
• 128503-59-3 methyl 2-O-benzyl-3,4,6-tri-O-methyl-β-D-glucopyranoside 

Downstream Products

• 52921-51-4 O³,O⁴,O⁶-trimethyl-D-gluconic acid-(N'-phenyl-hydrazide) 
• 112626-74-1 O³,O⁴,O⁶-trimethyl-D-arabino-[2]hexosulose-bis-phenylhydrazone 

Relevant academic research and scientific papers

Structure of the unusual Sinorhizobium fredii HH103 lipopolysaccharide and its role in symbiosis

Rhizobia are soil bacteria that form important symbiotic associations with legumes, and rhizobial surface polysaccharides, such as K-antigen polysaccharide (KPS) and lipopolysaccharide (LPS), might be important for symbiosis. Previously, we obtained a mutant of Sinorhizobium fredii HH103, rkpA, that does not produce KPS, a homopolysaccharide of a pseudaminic acid derivative, but whose LPS electrophoretic profile was indistinguishable from that of the WT strain. We also previously demonstrated that the HH103 rkpLMNOPQ operon is responsible for 5-acetamido-3,5,7,9-tetradeoxy-7-(3-hydroxybutyramido)-L-glyc-ero-L-manno-nonulosonic acid [Pse5NAc7(3OHBu)] production and is involved in HH103 KPS and LPS biosynthesis and that an HH103 rkpM mutant cannot produce KPS and displays an altered LPS structure. Here, we analyzed the LPS structure of HH103 rkpA, focusing on the carbohydrate portion, and found that it contains a highly heterogeneous lipid A and a peculiar core oligosaccharide composed of an unusually high number of hexuronic acids containing b-configured Pse5NAc7(3OHBu). This pseudaminic acid derivative, in its a-configuration, was the only structural component of the S. fredii HH103 KPS and, to the best of our knowledge, has never been reported from any other rhizobial LPS. We also show that Pse5NAc7(3OHBu) is the complete or partial epitope for a mAb, NB6-228.22, that can recognize the HH103 LPS, but not those of most of the S. fredii strains tested here. We also show that the LPS from HH103 rkpM is identical to that of HH103 rkpA but devoid of any Pse5NAc7(3OHBu) residues. Notably, this rkpM mutant was severely impaired in symbiosis with its host, Macroptilium atropurpureum.

A triterpenoid saponin from the seeds of Ricinus communis and its antimicrobial activity

A new oleanene triterpenoid was isolated from the butanolic seed extract of Ricinus communis. Its structure was elucidated as 3-O-[β-D- glucuronopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2) β-D-glucopyranosyl]-4α,20α-di(hydroxymethyl)olean-12-en-28-oic acid on the basis of spectral evidence i.e., FTIR, 1H and 13C NMR, and FAB-MS data. The isolated triterpenoid was found to have antimicrobial potential, viz. antibacterial and antifungal activity, where the growth of microbes was found to be an inverse function of the concentration of saponin. The MIC value for E. coli, Klebsiella pneumoniae and Staphylococcus aureus were found to be 260, 235, and 350 μg/mL.

Two antifungal active triterpenoid saponins from the seeds of Lathyrus plants

Two novel triterpenoid glycosides have been isolated from butanolic seeds extract of two varieties of Lathyrus plants, i.e. Lathyrus ratan and Lathyrus aphaca. Their structures were elucidated as 3-O-[β-D-glucuronopyranosyl- (1→4)-α-L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl] -olean-11,13 (18)-dien-28-oic acid (1) and 3-O-{β-D-xylopyranosyl-(1 → 2)-β-D-glcopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]- α-D-xylopyranosyl}-2, 16-dihydroxy-4-hydroxymethyl urs-12-en-28-oic acid (2) on the basis of spectral evidences, i.e. FTIR, 1H-NMR, 13C-NMR, ESI-MS and FAB-MS data. The isolated saponins were tested for their antifungal activity. Compound 1 showed maximum inhibition against Colletotrichum dematium (77.8%), whereas compound 2 showed maximum inhibition against Alternaria alternata (53.9%).

Chemical examination of juice of Citrus sinensis variety Jaffa

Phytochemical examination of Citrus sinensis juice var. Jaffa resulted in the isolation of 5,7-dihydroxy-3′,4′-dimethoxyflavanone 7-O-rhamnosyl(1→2)glucoside which is a hitherto unreported compound.