New Triterpene Saponins from Herniaria glabra

Three new saponins 1–3 were isolated from Herniaria glabra by means of prep. HPLC and TLC. The structures were established mainly by a combination of 2D-NMR techniques (COSY, TOCSY, ROESY, HMQC, and HMBC) as O-α-L -rhamnopyranosyl-(1→4)-O-β-D -glucopyranosyl-(1-→6)-O-[β-D -glucopyranosyl-(1→2)]-β-D -glucopyranosyl medicagen-28-ate (herniaria saponin 4; 1 ), O-β-D -glucopyranosyl-(1→3)-O-α-L -rhamnopyranosyl-(1→2)-O-[β-(3R)-D -apiofuranosyl-(1→3)]-β-D -4-O-acetylfucopyranosyl 3-O-(β-D -glucuronopyranosyl)-16α-hydroxymedicagen-28-ate (herniaria saponin 5; 2 ), and O-α-L -rhamnopyranosyl-(1→4)-O-β-D -glucopyranosyl-(1→6)-O-[β-D -6-O-acetylglucopyra nosyl-(1→2)]-β-D -glucopyranosyl medicagen-28-ate (herniaria saponin 6; 3 ).     

Anatoliosides: Five Novel Acyclic Monoterpene Glylcosides from Viburnum orientale

Five new acyclic monoterpene glycosides 1 – 5 were isolated from the leaves of Viburnum orientale (Caprifoliaceae). Anatolioside ( 1 ) is a monoterpene diglycoside and its structure was elucidated as linalo-6-yl 2′-O-(α-L -rhamnopyranosyl)β-D -glucopyranoside (arbitrary numbering of linalool moiety). Compounds 2 – 5 are all derivatives of 1 , containing additional monoterpene and sugar units, connected by ester and glycoside bonds. Their structures were established as linalo-6-yl O-[(2E,6R)-6-hydroxy-2, 6-dimethylocta-2,7-dienoyl]-(1? → 4″)-O-α-L -rhamnopyranosyl-(1″? → 2″″)-β-D -glucopyranoside ( = anatolioside A; 2 ), linalo-6-yl O-β-D -glucopyranosyl-(1? → 6?)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1? → 4″)-O-α-L -rhamnopyranosyl-(1″ → 2′)–β-D -glucopyranoside ( = anatolioside B; 3 ), linalo-6-yl O-β-D ribo-hexopyranos-3-ulosyl-(1′? → 6?)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1? → 4″)-O-α-L -rhamnopyranosyl-(1″ → 2′)-β-D -glucopyranoside ( = anatolioside C; 4 ) and linalo-6-yl O-[(2E, 6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1″? → 2″″)-O-β-D -glucopyranosly-(1″″ → 6?)-O-[(2E,6R)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]-(1? → 4″)-O-α-L -rhamnopyranosyl(1″ → 2′)-β-D -glucopyranoside ( = anatolioside D ; 5 ). The structure determinations were based on spectroscopic and chemical methods (acid and alkaline hydrolysis, acetylation and methylation).     

Lagotoside: A New Phenylpropanoid Glycoside from Lagotis stolonifera

From the aerial parts of Lagotis stolonifera (Scrophulariaccae), a new phenylpropanoid glycoside, lagotoside ( 8 ), and the three known glycosides ehrenoside ( 5 ), verbascoside (= acteoside; 6 ), and plantamajoside ( 7 ) were isolated, together with the four known iridoid glucosides aucubin ( 1 ), catalpol( 2 ), globularin ( 4 ), and lythantosalin ( 3 ). The structure of the new compound 8 was elucidated on the basis of chemical and spectral data as 2-(3-hy-droxy-4-methoxyphenyl)ethyl O-[α-L -arabinopyranosyl-(1 → 2)]-O-[α-L -rhamnopyranosyl-(1 → 3)]-4-O-feruloyl-β-D -glucopyranoside.     

A New Triterpene Saponin from Heteropappus biennis with an Unusual Carbohydrate Chain

A new saponin, O-α-D -arabinopyranosyl-(1→6)-O-[α-L -rhamnopyranosyl-(1→2)]-O-[β-D -xylopyranosyl-(1→3)]-β-D -glucopyranosyl arjunolate ( 1 ) was isolated from the flowers of Heteropappus biennis (LDB .) TAMAMSCH . The structure was established mainly by a combination of 1D selective and 2D NMR techniques like COSY, TOCSY, ROESY, HMQC, and HMBC. Molecular-modelling calculations showed that the oligosaccharide chain is rather rigid. Six minimum structures are discussed.     

Anatolioside E: A New Acyclic Monoterpene Glycoside from Viburnum orientale

A new open-chain monoterpene glycoside, anatolioside E ( 1 ), was isolated from the leaves of Viburnum orientale in addition to three known acyclic monoterpene glycosides, betulalbusides A ( 2 ) and B ( 3 ), and 2(E)-2,6-dimethyl-2,7-octadien-1,6-diol-6-O-β-D -glucopyranoside( 4 ). The structure of anatolioside E ( 1 ) was elucidated on the basis of chemical and spectral data as 6-O-[β-D -glucopyransoyl-(1?? → 6?″)-2-(E), 6(R), 2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1?″ → 2″″)-β-D -glucopyranosyl-(1″″ → 6?)-2-(E), 6(R), 2,6-dimethyl-6-hydroxy-2,7-octadienoyl-(1? → 4″)-α-L -rhamnopyranosyl-(1″″ → 2′)-β-D -glucopyranosyl]linalool.     

Ilwensisaponins A,B, C,and D: Triterpene Saponins from Scrophularia ilwensis

From the aerial parts of Scrophularia ilwensis, four new triterpene saponins, ilwensisaponins A–D ( 1 – 4 ) were isolated. The structures of the compounds were elucidated using chemical and spectral data as 13β, 28-epoxy-3-β-{{[β-D -glucopyranosyl-(1→2)]-[α-L -rhamnopyranosyl-(1→4)-β-D -glucopyranosyl-(1→3)]-β-D -fucopyranosyl}-oxy} olean-11-en-23-ol ( 1 ), 3-β-{{[β-D -glucopyranosyl-(1→2)]-[α-L -rhamnopyranosyl-(1→4)-β-D -glucopyranosyl-(1→3)]-β-D -fucopyranosyl}oxy}olena-11, 13(18)-diene-23, 28-diol ( 2 ), 3-β-{{[β-D -glucopyranosyl-(1→2)]-[α-L -rhamnopyranosyl-(1→4)-β-D glucopyranosyl-(1→3)]-β-D fucopyranosyl}oxy}-11α-methoxyolean- 12-ene-23, 28-diol (3) , and 3-β-{{[β-D -glucopyransoyl-(1→2)]-[α-L -rhamnopyranosyl-(1→4)-β-D -glucopyranosyl-(1→3)]-β-D -fucopyranosyl}oxy}olean-12-ene-11α,23,28-triol (4) .     

Studies on the Constituents of Paris Formosana Hayata Part II

Methyl palmitate (I), methyl stearate (II), stigmasterol (III), β-sitosterol (IV), (O -acyl)-β-D -glucopyranosyl-(1→3)-stigmasterol (V), (O -acyl)-β-D -glucopyranosyl-(1→3)-β-sitosterol (VI), β-D -glucopyranosyl-(1→3)-stigmasterol (VII), β-D -glucopyranosyl-(1→3)-β-sitosterol (VIII), β-D -ecdysone (IX), diosgenin-3-α-L -rhamopyranosyl-(1→2)-[α-L -arabinofuranosyl-(1→4)]-β-D -glucopyranoside (X), diosgenin-3-O -β-chacotrioside (dioscin) (XI), and diosgenin-3-O -α-L -rhamnopyranosyl-(1→4)-α-L -rhamnopyranosyl-(1→4)-[α-L -rhamnopyranosyl-(1→2)]-β-D -glucopyranoside (XII) were isolated and characterized from the stems of Paris formosana Hayata (Liliaceae).     

Isolation and Structural Study on Carbohydrates from Cynanchum otophyllum and Cynanchum paniculatum

Three new carbohydrates were isolated from the acidic hydrolysis part of the ethyl acetate extract of Cynanchum otophyllum Schneid (Asclepiadaceae) and one new carbohydrate from the ethyl acetate extract of Cynanchum paniculatum Kitagawa. Their structures were determined as methyl 2,6-dideoxy-3-O-methyl-α-D-arabino-hexopyranosyl-(1 → 4)-2,6-deoxy-3-O-methyl-β-D-arabino-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α-D-arabino-hexopyranoside (1), ethyl 2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α-l-lyxo-hexopyranoside (2), met hyl 2,6-dideoxy-3-O-methyl-α-l-ribo-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-β-D-lyxo-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α-D-arabino-hexopyranoside (3), and 2,6-dideoxy-3-O-methyl-β-D-ribo-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α-d-arabino-hexopyranosyl-(1 → 4)-2,6-dideoxy-3-O-methyl-α -d-arabino-hexopyranose (4), respectively, by spectral methods.     

Synthetic Antigens: Synthesis of 4-Aminophenyl O-α-D-Mannopyranosyl-(1→2)-O-α-D-mannopyranosyl-(1→6)-O-α-D-Mannopyranoside and A Related Di- and A Trisaccharide

Abstract

4-Nitrophenyl 2,3-O-isopropylidine-α-D-mannopyranoside 2 was condensed with O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1→2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl bromide 1 and 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide 11 in the presence of mercuric cyanide. Products were deprotected to yield, respectively, 4-nitrophenyl O-α-D-mannopyranosyl-(1→2)-O-α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside 6 and 4-nitrophenyl O-α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside 14. The 4-nitrophenyl group of 6 was reduced to give title trisaccharide. Bromide 1 was also condensed with methyl 2,3,4-tri-O-benzyl-α-D-manopyranoside 3 in the presence of silver trifluoromethanesulfonate and tetramethylurea to give protected trisaccharide derivative which was deprotected to furnish, methyl O-α-D-mannopyranosyl-(1→2)-O-α-D-mannopyranosyl-(1→6)-α-D-mannopyranoside 10. The identities of all protected and deprotected compounds were supported by ¹H and ¹³C NMR spectral data.     

CHEMOENZYMATIC SYNTHESIS OF NeuAcα-(2→3)-Galβ-(1→3)-[NeuAcα-(2→6)]-GalNAcα1- O-(Z)-Serine (N-PROTECTED MUC II OLIGOSACCHARIDE–SERINE)

An efficient synthesis of NeuAcα-(2→3)-Galβ-(1→3)-[NeuAcα-(2→6)]-GalNAcα1- O-(Z)-Serine (N-protected MUC II oligosaccharide–serine, 14) by a chemoenzymatic strategy is described. The enzymatic reaction of GalNAcα1- O-(Z)-Ser- OAll 7 with pNP-β-Gal in the presence of recombinant β1,3-galactosidase from Bacillus circulans gave Galβ-(1→3)-GalNAcα1- O-(Z)-Ser- OAll 3 in 68%. The introduction of two sialic acids into 3 was accomplished by a stepwise method. The branched Galβ-(1→3)-[NeuAcα-(2→6)]-GalNAcα1- O-(Z)-Ser- OAll 11 was constructed by a chemical method. Sialylation at the C-3 position of the terminal Gal residue on Galβ-(1→3)-[NeuAcα-(2→6)]-GalNAcα1- O-(Z)-Serine 2 using α2,3-(O)-sialyltransferase from rat liver gave a target compound 14 in a practical yield.     

Synthesis of a DI- and A Trisaccharide Related to the Antigen From Klebsiella Type 16

Using methyl triflate as promoter, methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1→4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate) and methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galacto-pyranosyl)-(1→-4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1(1→4)-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate) have been synthesised. Removal of protecting groups gave the di- and trisaccharide in the form of their methyl ester methyl glycoside related to the antigen of Klebsiella type 16.     

Linear Synthesis of The Methyl Glycosides of Tri-, Tetra-, and Pentasaccharide Fragments of The Shigella Flexneri Serotype 5A O-Antigen

ABSTRACT

The stepwise synthesis of methyl α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranoside (EBC-OMe, 1), methyl α-L-rhamnopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranoside (A(E)BC-OMe, 2), and methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-[α-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranoside (DA(E)BC-OMe, 3) is described. Compounds 1, 2 and 3 constitute the methyl glycosides of fragments of the O-specific polysaccharide of Shigella flexneri serotype 5a. Methyl 2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside was an appropriate BC precursor for the synthesis of 1. For the synthesis of the branched targets 2 and 3, a benzyl group was best suited at position 2 of rhamnose C. Thus, methyl 4-O-benzyl-α-L-rhamnopyranosyl-(1→3)-2,4-di-O-benzyl-α-L-rhamnopyranoside was the key intermediate to the BC portion. In all cases, 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride was a convenient E precursor, when used in combination with titanium tetrafluoride. All along, attention was paid to steric hindrance as a factor of major impact on the condensation steps outcome. Therefore, based on previous experience, 2-O-acetyl-3,4-di-O-allyl-α-L-rhamnopyranosyl trichloroacetimidate and 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl trichloroacetimidate were used as donors. Both suited all requirements when used as key precursors for residues A and D in the synthesis of 3, respectively.     

Large-Scale Synthesis of a Lewis b Tetrasaccharide Derivative,its Acrylamide Copolymer,and Related DI- and Trisaccharides for Use in Adhesion Inhibition Studies with Helicobacter Pylori.

ABSTRACT

The 2-aminoethyl glycoside of O-α-L-fucopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→3)-[O-α-L-fucopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-D-glucopyranose (Lewis B tetrasaccharide) was synthesized on a large scale and acryloylated with acryloyl chloride. The obtained oligosaccharide 2-acrylamidoethyl glycoside was then copolymerized with acrylamide to form a water-soluble, high molecular weight polymer, suitable for use in adhesion inhibition studies with Helicobacter pylori. Also synthesized were the corresponding derivatives of O-α-L-fucopyranosyl-(1→2)-O-β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranose and O-β-L-fucopyranosyl-(1→2)-β-D-galactopyranose.

     

Synthesis of Rhamnogalacturonan I Fragments

ABSTRACT

The partially deprotected trisaccharide 17 has been synthesized as an analogue of the repeating unit of the backbone of rhamnogalacturonan I. The trisaccharide 17 was obtained after prior selective derivatization of HO-3 and HO-4 of a rhamnopyranose cyanoethylidene glycosyl donor, followed by coupling with a tritylated galactopyranosyluronic acceptor (11), selective removal of the acetyl group at the O-2' position of the formed disaccharide 12, and glycosylation of the HO-2' position with methyl (ethyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-1-thio-β-D-galactopyranosid)uronate (14) providing methyl (methyl 2,3-di-O-benzyl-4-O-p-methoxybenzyl-α-D-galactopyranosyluronate)-(1→2)-(4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl)-(1→4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate (15). Finally, palladium chloride catalyzed deallylation (16) and hydrogenolysis over Pd-C resulted in methyl (methyl α-D-galactopyranosyluronate)-(1→2)-(4-O-benzoyl-α-L-rhamnopyranosyl)-(1→4)-α/β D-galactopyranuronate (17).     

Synthesis of Polyacrylamide Copolymers Containing (1→6)-Branched (1→3)-β-D-Linked Tri- and Tetra-Saccharides Related to Schizophyllan

Abstract

The allyl β-glycosides of a trisaccharide O-β-D-Glcp-(1→3)-O-[β-D-Glcp-(1→6)]-β-D-Glcp and of a tetrasaccharide O-β-D-Glqp-(1→3)-O-[β-D-Glqp-(1→6)]-O-β-D-Glcp-(1→3)-β-D-Glcp, corresponding to the branching point or the repeating unit of antitumor (1→6)-branched-(1→3)-β-D-glucans, have been synthesized starting from ethyl 2-O-benzoyl-4,6-O-benzylidene-l-thio-α-D-glucopyranoside and copolymerized in a radical reaction with acrylamide to obtain polyacrylamide copolymers containing the tri-and tetra-saccharides for immunochemical studies of schizophyllan.     

Synthesis of Methyl 2-O-, 3-O-, 4-O-, 6-O-, 2,3-Di-O- and 4,6-Di-O-β-D-Galactopyranosyl-β-D-glucopyranoside

Abstract

Synthesis of methyl O-β-D-galactopyranosyl-(1→2)-β-D-glucopyranoside 1, methyl O-β-D-galactopyranosyl-(1→3)-β-D-glucopyranoside 2, methyl O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside 3, methyl O-β-D-galactopyranosyl-(1→6)-β-D-glucopyranoside 4, methyl O-β-D-galactopyranosyl-(1→4)-[O-β-D-galactopyranosyl-(1→6)]-β-D-glucopyranoside 5, and methyl O-β-D-galactopyranosyl-(1→2)-[O-β-D-galactopyranosyl-(1→3)]-β-D-glucopyranoside 6, using 2,3,4,6 tetra-O-acetyl-α-D-galactopyranosyl trichloroacetimidate or 2,3,4,6 tetra-O-acetyl-α-D-galactopyranosyl bromide as a glycosyl donor and selectively protected derivatives of methyl O-β-D-glucopyranoside as glycosyl acceptors are described.     

Synthesis of Tetrasaccharide Repeating Unit of the K-Antigen from Klebsiella Type-16

Abstract

Starting from L-fucose, D-glucose and lactose, methyl O-[2,3-di-O-benzoyl-4, 6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl]-(1→4)-2,3-di-O-benzoyl-α-L-fucopyranoside and methyl O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1→4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1→4)-O-(methyl 2,3-di-O-benzoyl-β-D-glucopyranosyluronate)-(1→4)-2,3-di-O-benzoyl-α-L-fucopyranoside were synthesized. Removal of protecting groups gave the tetrasaccharide repeating unit of the antigen from Klebsiella type-16 in the form of its methyl ester methyl glycoside.     

A new flavonol glycoside and other flavonoids from the aerial parts of Taverniera aegyptiaca

Isolation of flavonoids from the aerial parts of Taverniera aegyptiaca Bioss. (Fabaceae) led to identification of one new flavonol glycoside, isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (1), along with eleven compounds, which previously have not been isolated from this plant quercetin-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (2), isorhamnetin-3-O-α-l-arabinopyranoside (3), quercetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (4), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (7), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (8), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside] (9), kaempferol 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (10), isorhamnetin (11), 4,4′-dihydroxy-2′-methoxychalcone (12), formononetin (13) and calycosin (15)] and some compounds already known from this plant [quercetin-3-O-robinobioside (5), isorhamnetin-3-O-robinobioside (6), afrormosin (14) and odoratin (16)].     

Bidesmosidic Oleanane Saponins from Xerospermum noronhianum

Three new oleanane‐type triterpenoid saponins, 3‐O‐(α‐L ‐rhamnopyranosyl(1→2)‐β‐D ‐fucopyranosyl)‐28‐O‐{[α‐L ‐rhamnopyranosyl(1→2)] [β‐D ‐fucopyranosyl(1→6)]‐β‐D ‐glucopyranosyl} oleanolic acid ( 1 ), 3‐O‐[α‐L ‐rhamnopyranosyl(1→3)‐β‐D ‐fucopyranosyl]‐28‐O‐[α‐L ‐rhamnopyranosyl(1→4)‐β‐D ‐glucopyranosyl] oleanolic acid ( 2 ), and 3‐O‐{α‐L ‐rhamnopyranosyl(1→2)‐[3′,4′‐diacetoxy‐β‐D ‐fucopyranosyl]}‐28‐O‐[α‐L ‐rhamnopyranosyl(1→2)‐β‐D ‐glucopyranosyl] oleanolic acid ( 3 ) have been isolated from the stems of Xerospermum noronhianum. The structures of the saponins were determined as a series of bidesmosidic oleanane saponins based on spectral evidence. The anticholinesterase activity of the saponins 1 – 3 was also evaluated.     

27-Ald-triterpenoid saponins from Adina rubella

Four new triterpenoid saponins were isolated from the roots of Adina rubella Hance. They were characterized as adinaic acid 3β-O-[α-L-rhamnopyranosyl(l→2)-β-D-glucopyranosyl(l→2)-β-D-glucurono-pyranoside-6-O-methyl ester]-28-O-β-D)-glucopyranoside, adinaic acid 3β-O-[α-L-rham-nopyranosyl(l→2)-β-D-glucopyranosyl(l→2)-β-D-glucuronopyranoside-6-O-butyl ester]-28-O-β-D-glu-copyranoside, adinaic acid 3β-O-[β-D-glucopyranosyl(l→2)-β-D-glucopyranosyl]-(28→1)-β-D-gluco-pyranosyl(l→6)-β-D-glucopyranosyl ester, 27-hydroxyursolic acid 3β-O-[α-L-rhamnopyranosyl (l→2)-β-O-glucopyranosyl(l→2)-β-D)-glucuronopyranoside-6-O-methyl ester]-28-O-β-D)-glucopyranoside. Their structures were elucidated by spectral methods, especially with the aid of 2D NMR techniques. Their complete assignments of the 1H and 13C NMR signals were carried out.