NMR-based identification of cell wall anionic polymers of Spirilliplanes yamanashiensis VKM Ac-1993(T).

The cell wall of Spirilliplanes yamanashiensis VKM Ac-1993(T) contains four anionic polymers, viz., three teichoic acids and a sugar-1-phosphate polymer. The following are the structures of the teichoic acids: poly[-6-beta-D-glucopyranosyl-(1-->2)-glycerol phosphate] (PI), 1,3-poly(glycerol phosphate) bearing N-acetyl-alpha-D-glucosamine residues at O-2 (70%) (PII), and poly[-6-N-acetyl-alpha-D-glucosaminyl-(1-->2)-glycerol phosphate] (PIII). The repeating unit of the fourth polymer (PIV) has the structure of -6-alpha-D-GlcpNAc-(1-->6)-alpha-D-GlcpNAc-1-P- with a 3-O-methyl-alpha-D-mannopyranosyl residues at position 3 of some 6-phosphorylated N-acetylglucosamine residues (50%). Polymers PI, PIII and PIV have not hitherto been found in prokaryotic cell walls.     

Non-phenolic antioxidant compounds from Buddleja asiatica

The methanol extract of the leaves of Buddleja asiatica Lour. (Loganiaceae) showed antioxidant activity toward the well known in vitro antioxidant tests such as total antioxidant capacity by the phosphomolybdenum method, free radical scavenging activity by the 1,1-diphenyl-2-picrylhydrazyl scavenging assay (DPPH assay) and hydrogen peroxide scavenging methods. Due to the high scavenging activity of the n-butanol successive fraction toward DPPH and H2O2 (SC50 = 11.99 and 18.54 microg/ml, respectively), this extract was subjected to chromatographic separation and isolation. Four non-phenolic compounds were isolated and identified on the basis of spectroscopic and chemical analyses: 1-O-beta-D-glucopyranosyl-2-methoxy-3-(2-hydroxy-triaconta-3,12-dienoate)-glycerol (1), 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-beta-D-fucopyranosyl-olean-11,13(18)-diene-3 beta,23,28-triol (2), 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)]-beta-D-fucopyranosyl-olean-11,13(18)-diene-3,23,28-triol (3), and 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)]-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucuronopyranosyl-acid-olean-11,13(18)-diene-3 beta,23,28-triol (4). The four compounds were evaluated as antioxidant agents using the three antioxidant bioassay tests.     

Glucuronide triterpene saponins from Bersama engleriana

Five 3-O-glucuronide triterpene saponins (1-5) were isolated from the stem bark of Bersama engleriana Gurke along with two known saponins, polyscias saponin C and aralia saponin 15, and one major C-glycoside xanthone, mangiferin. The structures of the saponins were established mainly by means of spectroscopic methods (one- and two-dimensional NMR spectroscopy as well as FAB-, HRESI-mass spectrometry) as 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-betulinic acid (1), 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-galactopyranosyl-(1-->3)]-beta-D-glucuronopyranosyl]-oleanolic acid (2), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-xylopyranosyl-(1-->6)-beta-d-glucopyranosyl]-oleanolic acid (3), 3-O-[beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl]-oleanolic acid (4), and 3-O-[beta-d-glucopyranosyl-(1-->3)-beta-D-galactopyranosyl-(1-->3)-beta-D-glucuronopyranosyl]-28-O-[beta-d-xylopyranosyl-(1-->6)-beta-D-glucopyranosyl]-oleanolic acid (5).     

Triterpenoid saponins from the stem bark of Elattostachys apetala

Six new triterpenoid saponins have been isolated from the stem bark of Elattostachys apetala together with four known triterpenoid saponins. Three of these new compounds are glycosides of a newly described genin, 29-hydroxyhederagenin (1). On the basis of spectral evidence, the structures of the new saponins were concluded to be alpha-hederin 28-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl] ester (2), sapindoside B 28-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl] ester (3), 3-O-beta-D-xylopyranosyl astrantiasaponin VII (4), 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (5), 3-O-[alpha-L-arabinopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (6), and 3-O-[beta-D-xylopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-gluco pyranosyl-(1-->6)]-beta-D-glucopyranosyl]-29-hydroxyhederagenin (7).     

Triterpenoid saponins from Schefflera arboricola

Nine triterpenoid saponins were isolated from the leaves and stems of Schefflera arboricola. The saponins were characterised, on the basis of chemical and spectral evidence, as 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucuronopyranosyl] oleanolic acid, 3-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucuronopyranosyl] echinocystic acid, 3-O-[beta-D-apiofuranosyl-(1-->4)-beta-D-glucuronopyranosyl] oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-ramnopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-[beta-D-galactopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-[beta-D-galactopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl ester, 3-O-beta-D-apiofuranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid and 3-O-beta-D-apiofuranosyl-(1-->4)-[alpha-L-arabinopyranosyl-(1-->2)-] beta-D-glucuronopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl ester.     

Astersedifolioside A-C, three new oleane-type saponins with antiproliferative activity

A phytochemical analysis of Aster sedifolius has led to the isolation of three novel triterpenoid saponins, based on an oleane-type skeleton and named astersedifolioside A (1), B (2) and C (3). On the basis of chemical, and 2D NMR and mass spectrometry data, the structures of the new compounds were elucidated as 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl] echinocystic acid 28-[O-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranoside] (1), 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl] echinocystic acid 28-[O-beta-D-xylopyranosyl (1-->4)-O-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranoside] (2) and 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl] echinocystic acid 28-[O-beta-D-xylopyranosyl (1-->4)-O-alpha-L-rhamnopyranosyl (1-->2)-alpha-L-arabinopyranoside] (3). The isolated compounds showed antiproliferative effect in KiMol, a transformed thyroid cell line.     

Acetylated glucuronide triterpene bidesmosidic saponins from Symplocos glomerata

Nine new bidesmosidic 3-O-glucuronide oleanane triterpenoid saponins were isolated from the stem bark of Symplocos glomerata King along with two known saponins, salsoloside C and copteroside E, and two major lignans, (-)-pinoresinol and (-)-pinoresinol-4'-O-beta-D-glucopyranoside. The structures of the new saponins were established using one- and two-dimensional NMR spectroscopy and mass spectrometry as, 3-O-[beta-D-xylopyranosyl(1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[beta-D-xylopyranosyl(1-->4)-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[beta-D-xylopyranosyl (1-->4)-[2,3-O-diacetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[alpha-L-arabinopyranosyl(1-->4)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[alpha-L-arabinopyranosyl (1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-xylopyranosyl (1-->2)]-[beta-D-xylopyranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-glucopyranosyl (1-->2)]-[beta-D-xylopyranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, 3-O-[[beta-D-glucopyranosyl (1-->2)]-[alpha-L-arabinofuranosyl (1-->4)]-[3-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-oleanolic acid, and 3beta-O-[beta-D-xylopyranosyl(1-->4)-[2-O-acetyl]-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-morolic acid. The EtOH and EtOAc extracts of the stem bark showed no cytotoxic activity. At a concentration of 370 microg/ml, the saponin mixture showed haemolytic activity and caused 50% haemolysis of a 10% suspension of sheep erythrocytes.     

Triterpenoid saponins from Oreopanax guatemalensis

Seven oleanane-type saponins were isolated from the leaves and stems of Oreopanax guatemalensis, together with ten known saponins of lupane and oleanane types. The new saponins were respectively characterized as 3-O-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha- L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-beta-D-glucopyranosyl 3beta-hydroxy olean-11,13(18)-dien-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta- D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl]3beta-hydroxy olean-11,13(18)-dien-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]3beta, 23 dihydroxy olean-18-en-28-oic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-6-O-acetyl glucopyranosyl-(1-->6)-beta-D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[beta-D-xylopyranosyl-(1-->2 )-]beta-D-glucopyranosyl]ester, 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl]hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1-->2)-]beta-D-glucopyranosyl] ester and 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl] hederagenin 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-[alpha-L-arabinofuranosyl-(1-->2)]-beta-D-glucopyranosyl] ester. The structures were determined by spectral analyses. The NMR assignments were made by means of HOHAHA, 1H-1H COSY, HMQC, HMBC spectra and NOE difference studies.     

Transglycosylation to ginseng saponins by cyclomaltodextrin glucanotransferases

Ten new alpha-glucosylginsenosides were found to be synthesized from dextrin and four ginsenosides, -Rb1, -Rc, -Re, and -Rg1, by the successive actions of B. stearothermophilus cyclomaltodextrin glucanotransferase and Rhizopus glucoamylase. Seven of them were isolated in the pure state by extraction with n-butanol saturated with water, silica gel column chromatography, and high pressure liquid chromatography, and identified as 3-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[beta-D-glcp-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[alpha-D-glcp-(1-->4)-beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[alpha-L-araf-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 3-O-[beta-D-glcp-(1-->2)-beta-D-glcp]-20-O-[(4G-alpha-D-glcp)-alpha-L-araf-(1-->6)-beta-D-glcp]-20(S)-protopanaxadiol, 6-O-[alpha-L-rhap-(1-->2)-beta-D-glcp]-20-O-[alpha-D-glcp-(1-->4)-beta-D-glcp]-20(S)-protopanaxatriol, 6-O-[alpha-D-glcp-(1-->4)-beta-D-glcp]-20-O-(beta-D-glcp)-20(S)-protopanaxatriol, and 6-O-[alpha-D-glcp-(1-->3)-beta-D-glcp]-20-O-(beta-D-glcp)-20(S)-protopanaxatriol, by spectroscopy (FAB-MS, IR, 1H-NMR and 13C-NMR) and hydrolysis products in 50% acetic acid. The bitterness of these alpha-glucosyl-ginsenosides was less than that of ginsenosides.     

Effect of starvation on the distribution of positional isomers and enantiomers of triacylglycerol in the diatom Phaeodactylum tricornutum

The diatom Phaeodactylum tricornutum was cultivated in a standard medium and under sulfur, silicon, nitrogen and phosphorus starvation and its triacylglycerols (TAGs) were analyzed by RP-HPLC/MS-APCI. Nearly 100 molecular species of polyunsaturated TAGs were identified. RP-HPLC was used to isolate positional isomers of TAGs, which were further separated by chiral HPLC. First eluted were those TAGs that have an eicosapentaenoic acid moiety in the sn-1 position. The ratios of symmetrical to asymmetrical TAGs in P. tricornutum were affected under sulfur-, nitrogen-, phosphorus- and silica-starvation, i.e. in cultivations involving cells in nutrient stress. The ratios of positional TAGs and also the proportions of enantiomers were changed. The ratios of symmetrical to asymmetrical TAGs in the control and under N- and P-starvation were very close. In the control, the ratio of 1,2-dipalmitoyl-3-eicosapentaenoyl-rac-glycerol to 1,3-dipalmitoyl-2-eicosapentaenoyl-rac-glycerol was 3:1 and the ratio of 1,2-dieicosapentaenoyl-3-palmitoyl-rac-glycerol to 1,3-dieicosapentaenoyl-2-palmitoyl-rac-glycerol was 9:1. Under N-starvation the ratios were reversed irrespective of the presence or absence of silicate in the medium. A similar pattern was found in P- and S-starvation.     

Two diastereomeric saponins with cytotoxic activity from Albizia julibrissin

Two diastereomeric saponins, julibrosides J1 (1) and J9 (2), both of which show cytotoxic activity, were obtained from the stem bark of Albizia julibrissin Durazz. On the basis of chemical and spectral evidence [L.B. Ma et al., Carbohydr. Res., 281 (1996) 35-46], the structure of 1 was revised as 3-O-[beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6) -beta-D-glucopyranosyl]-21-O-[(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O- [4-O-((6R)-2-trans-2,6-dimethyl-6-O-(beta-D-quinovopyranosyl)-2,7- octadienoyl)-beta-D-quinovopyranosyl]-2,7-octadienoyl] acacic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->4 )]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester. The diastereoisomer 2 of 1 was identified as 3-O-[beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6) -beta-D-glucopyranosyl]-21-O-[(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O- [4-O-((6S)-2-trans-2,6-dimethyl-6-O-(beta-D-quinovopyranosyl)-2,7- octadienoyl)-beta-D-quinovopyranosyl]-2,7-octadienoyl] acacic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->4 )]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester. Saponin 2 is a new saponin named julibroside J9. Both julibrosides J1 and J9 show good inhibitory action against the KB cancer cell line in vitro.     

Bioactive saponins from Astragalus suberi L. growing in Yemen

From the aerial parts of Astragalus suberi L., Fabaceae, seven saponins were isolated. Based on spectral data (IR, 1H and 13C NMR and HR-FABMS), the structures were established as 3-O-(beta-D-glucopyranosyl)-soyasapogenol B (1); 3-O-(beta-D-glucuronopyranosyl)-soyasapogenol B (2); 3-O-[beta-D-galactopyranosyl (1-->2)-beta-D-glucopyranosyl]-soyasapogenol B (3); 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucopyranosyl]-soyasapogenol B (4); 3-O-[beta-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucopyranosyl]-11-hydroxy-soyasapogenol B (5); 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucuronopyranosyl]-soyasapogenol B (6) and 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucuronopyranosyl]-complogenin (7). The isolated saponins exhibited antibacterial activities against Gram-positive and Gram-negative bacteria with minimum inhibitory concentration values >100 microg/ml, antifungal activity against all the strains tested with minimum fungicidal concentration values between 25 and 50 microg/ml and inhibited the growth of Hep-2 (human carcinoma of larynx), with IC50 values between 50 microg/ml (compounds 5-7) and 100 microg/ml (compounds 1-4), and Hela (human carcinoma of cervix) cell lines in culture with different IC50 values [74 (compound 7), 98 (compound 5) and 180 microg/ml (compounds 1-4 and 6)].     

Processive lipid galactosyl/glucosyltransferases from Agrobacterium tumefaciens and Mesorhizobium loti display multiple specificities

The glycosyltransferase family 21 (GT21) includes both enzymes of eukaryotic and prokaryotic organisms. Many of the eukaryotic enzymes from animal, plant, and fungal origin have been characterized as uridine diphosphoglucose (UDP-Glc):ceramide glucosyltransferases (glucosylceramide synthases [Gcs], EC 2.4.1.80). As the acceptor molecule ceramide is not present in most bacteria, the enzymatic specificities and functions of the corresponding bacterial glycosyltransferases remain elusive. In this study, we investigated the homologous and heterologous expression of GT21 enzymes from Agrobacterium tumefaciens and Mesorhizobium loti in A. tumefaciens, Escherichia coli, and the yeast Pichia pastoris. Glycolipid analyses of the transgenic organisms revealed that the bacterial glycosyltransferases are involved in the synthesis of mono-, di- and even tri-glycosylated glycolipids. As products resulting from their activity, we identified 1,2-diacyl-3-(O-beta-D-galacto-pyranosyl)-sn-glycerol, 1,2-diacyl-3-(O-beta-D-gluco-pyranosyl)-sn-glycerol as well as higher glycosylated lipids such as 1,2-diacyl-3-[O-beta-D-galacto-pyranosyl-(1-->6)-O-beta-D-galacto-pyranosyl]-sn-glycerol, 1,2-diacyl-3-[O-beta-D-gluco-pyranosyl-(1-->6)-O-beta-D-galacto-pyranosyl]-sn-glycerol, 1,2-diacyl-3-[O-beta-D-gluco-pyranosyl-(1-->6)-O-beta-D-gluco-pyranosyl]-sn-glycerol, and the deviatingly linked diglycosyldiacylglycerol 1,2-diacyl-3-[O-beta-D-gluco-pyranosyl-(1-->3)-O-beta-D-galacto-pyranosyl]-sn-glycerol. From a mixture of triglycosyldiacylglycerols, 1,2-diacyl-3-[O-beta-D-galacto-pyranosyl-(1-->6)-O-beta-D-galacto-pyranosyl-(1-->6)-O-beta-D-galacto-pyranosyl]-sn-glycerol could be separated in a pure form. In vitro enzyme assays showed that the glycosyltransferase from A. tumefaciens favours uridine diphosphogalactose (UDP-Gal) over UDP-Glc. In conclusion, the bacterial GT21 enzymes differ from the eukaryotic ceramide glucosyltransferases by the successive transfer of up to three galactosyl and glucosyl moieties to diacylglycerol.     

Specific inhibition of macrophage migration inhibition factor by fucosylated glycolipid RM.

The effects of glycolipids on the interaction of the MIF (migration inhibition factor) with rat macrophages were examined using a migration inhibition assay system. MIF activity was specifically blocked by fucosylated Glycolipid RM [Gal alpha 1-3Gal(2-1 alpha Fuc) beta 1-3GalNAc beta 1-3Gal beta 1-4Glc beta 1-1ceramide, (1978) J. Biochem. 83, 85-90], but not by Cytolipin R, hematoside, or blood group B active glycolipid [Gal alpha 1-3Gal(2-1 alpha Fuc) beta 1-4GlcNAc beta 1-3Gal beta 1-4Glc beta 1-1ceramide]. Inhibition of MIF activity was proportional to the concentration of Glycolipid RM. These findings suggest that Glycolipid RM acts as a receptor for MIF.     

Five saponins from the root bark of Aralia elata

Five saponins, 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-oleanolic acid 28-O-beta-D-glucopyranosyl ester (aralia-saponin V), 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-echinocystic acid 28-O-beta-D-glucopyranosyl ester (aralia-saponin VI), 3-O-beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl (1-->3)]-beta-D-glucopyranosyl]-hederagenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin VII), 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl]-caulophyllogenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin VIII), 3-O-[beta-D-glucopyranosyl (1-->2)-[beta-D-glucopyranosyl(1-->3)]-alpha-L-arabinopyranosyl]-hederagenin 28-O-beta-D-glucopyranosyl ester (aralia-saponin IX), were isolated from the root bark of Aralia elata (Miq.) Seem., together with four known compounds. Their structures were determined on the basis of chemical and spectroscopic methods.     

Triterpenoid saponins from Meryta lanceolata

Four new oleanane-type saponins and a known one were isolated from the leaves and stems of Meryta lanceolata. The new saponins were characterised by spectroscopic means and chemical hydrolysis as 3-O-[beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D- glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-6-O-acetyl glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester and 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->3)-alpha-L-arabinopyranosyl]echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester. The NMR assignments were made by means of HOHAHA, 1H-1H COSY, HMQC, HMBC and NOE difference studies.     

Oligosaccharide polyester and triterpenoid saponins from the roots of Polygala japonica

An oligosaccharide polyester, 1-O-(E)-p-coumaroyl-(3-O-benzoyl)-beta-D-fructofuranosyl-(2-->1)-[6-O-(E)-feruloyl-beta-D-glucopyranosyl-(1-->2)]-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)-(4-O-acetyl)-beta-D-glucopyranosyl-(1-->3)]-4-O-[4-O-alpha-L-rhamnopyranosyl-(E)-p-coumaroyl]-alpha-D-glucopyranoside (polygalajaponicose I), and four triterpenoid saponins, 3beta, 23, 27-trihydroxy-29-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-olean-12-en-28-oic acid (polygalasaponin XLVII), 3-O-beta-D-glucopyranosyl presenegenin 28-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (polygalasaponin XLVIII), 3-O-beta-D-glucopyranosyl presenegenin 28-O-beta-D-galactopyranosyl-(1-->5)-beta-D-apiofuranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester (polygalasaponin XLIX) and 2beta, 27-dihydroxy-3-O-beta-D-glucopyranosyl 11-oxo-olean-12-en-23, 28-dioic acid 28-O-beta-D-galactopyranosyl-(1-->5)-beta-D-apiofuranosyl-(1-->4)-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-fucopyranosyl ester (polygalasaponin L), in addition to five known compounds have been isolated from the roots of Polygala japonica.     

Phenolic glycosides from Kaempferia parviflora

Three phenolic glycosides were isolated together with two known flavonol glycosides from the H2O-soluble fraction of rhizomes of Kaempferia parviflora. Their structures were determined to be rel-(5aS,10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]indeno[1,2-d]furan-6-one 5a-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-d-glucopyranoside] (1), its rel-5aS,10bR isomer (2), and (2R,3S,4S)-3-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-d-glucopyranosyl]-3'-O-methyl-ent-epicatechin-(2alpha-->O-->3,4alpha-->4)-(5aS,10bS)-5a,10b-dihydro-1,3,5a,9-tetrahydroxy-8-methoxy-6H-benz[b]indeno[1,2-d]furan-6-one 5a-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside] (3). The structures were elucidated on the basis of analyses of chemical and spectroscopic evidence.     

Syntheses of the 4-nitrophenyl glycosides of hyalobiuronic acid and chondrosine

4-Nitrophenyl [sodium beta-D-glucopyranosyluronate]-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside (1) and 4-nitrophenyl [sodium beta-D-glucopyranosyluronate]-(1-->3)-2-acetamido-2-deoxy-beta-D-galactopyranoside (2) were prepared from the zwitterions hyalobiuronic acid [beta-D-glucopyranuronic acid-(1-->3)-2-amino-2-deoxy-D-glucopyranose] and chondrosine [beta-D-glucopyranuronic acid-(1-->3)-2-amino-2-deoxy-D-galactopyranose], respectively. Compounds 1 and 2 were not hydrolysed by bovine testicular hyaluronidase.     

Saponins and acylated saponins from Dizygotheca kerchoveana

Four new triterpenoid saponins were isolated from the leaves and stem of branches of Dizygotheca kerchoveana along with seven known ones. The new saponins were respectively characterized as 3-O-[beta-D-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid, 3-O-[beta-D-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester, 3-O-[beta-D-3-O-trans-p-coumaroyl-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester and 3-O-[beta-d-3-O-cis-p-coumaroyl-glucopyranosyl-(1-->3)]-[beta-D-glucopyranosyl-(1-->2)]-alpha-L-arabinopyranosyl echinocystic acid 28-O-[alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl] ester. Their structures were elucidated by 1D and 2D NMR experiments, FAB-MS as well as chemical means.