Synthesis of sucrose epoxides,partial de-esterification of 1′,2:4,6-di-O-isopropylidenesucrose tetra-acetate,and selective tosylation of 3,6′-di-O-acetyl-1′,2:4,6-di-O-isopropylidenesucrose

Selective de-esterification of 1′,2:4,6-di-O-isopropylidenesucrose tetra-acetate² (1) with methanolic ammonia at ?10° gave an inseparable mixture (2+3) of the 3,4′,6′- and 3,3′,6′-triacetates and also the 4,6′-diacetate 4. When the reaction was performed at 5°, it gave 4, the 4-acetate 8, and the parent diacetal 9. These derivatives allow selective reaction at hydroxyl groups in sucrose, in particular at HO-3′ and, HO-4′, not hitherto possible. Mesylation of 4 gave the 3′,4′-dimesylate 7, which, on treatment with aqueous acetic acid followed by acetylation, afforded 3′,4′-di-O-mesylsucrose hexa-acetate (11). Treatment of 11 with sodium methoxide in methanol at 70° for 1 min gave the ribo-3′,4′-epoxide 12 as the minor, and the lyxo-3′,4′-epoxide 13 as the major, product. Selective tosylation of 4 gave the 3',4'-ditosylate 14 (3.7%), 4′-tosylate 15 (3.1%), and 3'-tosylate 16 (31%), indicating the order of reactivity HO-3′>HO-4′ in 4. De acetalation of 15 and 16 followed by acetylation gave the hepta-acetates of 4′- and 3′-O-tosylsucrose, respectively, which were converted into the respective epoxides, 13 and 12, by methanolic sodium methoxide.     

Rubrenolide and rubrynolide: An alkene-alkyne pair from Nectandra rubra

Structures are proposed for rubrenolide, (2S,4R)-2-[(2′S)-2′,3′-dihydroxypropyl]-4-(dec-9′'-enyl)-γ-lactone, and rubrynolide, (2S,4R)-2-[(2′S)-2′,3′-dihydroxypropyl]-4-(dec-9′'-ynyl)-γ-lactone, isolated from Nectandra rubra (Lauraceae).     

Lignan glycosides from the Rhizomes of Smilax trinervula and their Biological activities

Phytochemical investigation of the rhizomes of Smilax trinervula led to isolation and structure elucidation of eight lignan glycosides, including five new lignans, namely, (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4′-O-β-d-glucopyranoside (1), (7S, 8R, 8′R)-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4-O-β-d- glucopyranoside (2) (7S, 8R)-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-4′, 7-epoxy-8, 5′-neolignan 9′-O-β-d-glucopyranoside (3), (7R, 8R)-4, 9, 9′-trihydroxy-3, 5-dimethoxy-7.O.4′, 8.O.3′- neolignan 9′-O-β-d-glucopyranoside (4), and (7S, 8R)-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-8, 4′-oxy-neolignan 4-O-β-d-glucopyranoside (5), along with three known compounds (6-8). Their structures were established mainly on the basis of 1D and 2D NMR spectral data, ESI–MS and comparison with the literature. Compounds 1-8 were tested in vitro for their cytotoxic activity against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Compounds 3 and 5 exhibited cytotoxic activity against Lovo cells, with IC₅₀ value of 10.4 μM and 8.5 μM, respectively.     

Some observations on the selective benzoylation of maltose and its derivatives

Benzoylation of β-maltose monohydrate (2) with 10 mol. equiv. of benzoyl chloride in pyridine at ?40° gave 1,2,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)-β-D-glucopyranose (5) in 87% yield, without the need for column chromatography. Similarly, benzoylation of 2 with 8 mol. equiv. of reagent afforded the octabenzoate 5, and the 1,2,6,2′,3′,6′-hexabenzoate 11 in 3%, 79%, and 12% yield, respectively. Methyl 2,6,2′,3′,4′,6′-hexa-O-benzoyl-β-maltoside (10) was directly isolated as a crystalline monoethanolate in 83% yield, from the reaction mixture obtained by the benzoylation of methyl β-maltoside monohydrate (8) with 8.9 mol. equiv. of reagent. Benzoylation of 8 with 7 mol. equiv. of reagent produced 10 and the 2,6,2′,3′,6′-pentabenzoate 16 in 71% and 23% yield, respectively. The order of reactivity of the hydroxyl groups in methyl 4′,6′-O-benzylidene-β-maltoside towards benzoylation is HO-2, HO-6>HO-2′ ≈ HO-3′>HO-3. Benzoylation of methyl β-cellobioside (33) with 7.9 mol. equiv. of reagent gave the heptabenzoate and the 2,6,2′,3′,4′,6′-hexabenzoate 36 in 56% and 27% yield, respectively. Compounds 5, 16, and 36 were transformed into 4-O-α-D-glucopyranosyl-D-allopyranose, methyl 4-O-α-D-galactopyranosyl-β-D-allopyranoside, and methyl 4-O-β-D-glucopyranosyl-β-D-allopyranoside, respectively, by sequential sulfonylation, nucleophilic displacement, and O-debenzoylation.     

Benzofuranoid neolignans from Aniba simulans

Forteen neolignans, isolated from the benzene extract of Aniba simulans (Lauraceae) trunk wood, included the hitherto undescribed (2S, 3S, 5R)-5-allyl-5,7-dimethoxy-2-(3′,4′,5′-trimethoxyphenyl)-3-methyl-2,3,5,6-tetra-hydro-6-oxobenzofuran, (2R,3S,5R) -5-allyl-5-methoxy-2-(3′-methoxy-4′,5′-methylenedioxyphenyl)-3-methy1-2,3,5, 6-tetrahydro-6-oxobenzofuran, (2S,3S)-6-O-allyl -5-methoxy-2-(3′-methoxy-4′-5′-methylenedioxyphenyl)-3-methyl-2,3-dihydrobenzofuran, (2R,3S)-6-O-allyl-5-methoxy-2- (3′-methoxy-4′,5′-methylenedioxyphenyl)-3-methyl-2,3-dihydrobenzofuran and 7-allyl-6-hydroxy-5-methoxy-2-(3′-methoxy-4,5′ -methylenedioxyphenyl)-3-methylbenzofuran.     

Biflavones from the leaves of Araucaria excelsa

Eight biflavones have been isolated from the leaf extracts of Araucaria excelsa. 7″-O-Methylamento-flavone, 7,7″-di-O-methylamentoflavone, 4′ or 4″', 7-di-O-methylcupressuflavone, 7,7″,4″'-tri-O-methyl agathisflavone and 7,4′,7″-tri-O-methylamentoflavone are new compounds and are being reported for the first time. The others are 7,7″-di-O-methylagathisflavone,7,4′,7″,4″'-tetra-O-methylamentoflavone and 7,4′,7″,4″'-tetra-O-methyl-cupressuflavone. Mass and NMR spectral studies are used for structural elucidation. In addition, the presence of several other biflavones has been indicated by TLC examination of methylated products.     

Two new guaiane sesquiterpenes from Datura metel L. with anti-inflammatory activity

Chemical investigation of an acidic methanol extract of the whole plants of Datura metel resulted in the isolation of two new guainane sesquiterpenes, 1β,5α,7β-guaiane-4β,10α,11-triol (1) and 1α,5α,7α-11-guaiene-2α,3β,4α,10α,13-pentaol (2), along with eight known compounds: pterodontriol B (3), disciferitriol (4), scopolamine (5), kaempferol 3-O-β-d-glucosyl(1 → 2)-β-d-galactoside 7-O-β-d-glucoside (6), kaempferol 3-O-β-glucopyranosyl(1 → 2)-β-glucopyranoside-7-O-α-rhamnopyranoside (7), pinoresinol 4′′-O-β-d-glucopyranoside (8), (7R,8S,7′S,8′R)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxy-lignan-4-O-β-d-glucopyranoside (9), and (7S,8R,7′S,8′S)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4-O-β-d-glucopyranoside (10). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. Compounds 2-4 and 6-10 were shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated BV cells.     

Biotransformation of naringin and naringenin by cultured Eucalyptus perriniana cells

The biotransformation of naringin and naringenin was investigated using cultured cells of Eucalyptus perriniana. Naringin (1) was converted into naringenin 7-O-β-d-glucopyranoside (2, 15%), naringenin (3, 1%), naringenin 5,7-O-β-d-diglucopyranoside (4, 15%), naringenin 4′,7-O-β-d-diglucopyranoside (5, 26%), naringenin 7-O-[6-O-(β-d-glucopyranosyl)]-β-d-glucopyranoside (6, β-gentiobioside, 5%), naringenin 7-O-[6-O-(α-l-rhamnopyranosyl)]-β-d-glucopyranoside (7, β-rutinoside, 3%), and 7-O-β-d-gentiobiosyl-4′-O-β-d-glucopyranosylnaringenin (8, 1%) by cultured cells of E. perriniana. On the other hand, 2 (14%), 4 (7%), 5 (13%), 6 (2%), 7 (1%), naringenin 4′-O-β-d-glucopyranoside (9, 4%), naringenin 5-O-β-d-glucopyranoside (10, 2%), and naringenin 4′,5-O-β-d-diglucopyranoside (11, 5%) were isolated from cultured E. perriniana cells, that had been treated with naringenin (3). Products, 7-O-β-d-gentiobiosyl-4′-O-β-d-glucopyranosylnaringenin (8) and naringenin 4′,5-O-β-d-diglucopyranoside (11), were hitherto unknown.     

8-O-methyl- and the first 3-O-methylflavan-3,4-diols from Acacia saxatilis

The light purple heartwood of Acacia saxatilis contains (+)-2,3-trans-3,4-trans- and (+)-2,3-trans-3,4-cis-diastereoisomers of 8-methoxy-7,j',4'-trihydroxy- and 7,3′,4′-trihydroxyflavan-3,4-diols as major components. Evidence was also obtained of the first 3-methyl ether of metabolites: of this type, notably of (+)-8-methoxy-7,3′,4′-trihydroxy-2,3-trans-flavan-3,4-cis-diol. Flavonol, dihydroflavonol and flavanone analogies accompany these. The correlation between colour of Acacia heartwoods and structure, phenolic substitution, stereochemistry and composition of their flavonoid components is discussed.     

Sucrochemistry : Part X. 1′,4,6′-tri-O-mesylsucrose penta-acetate: A comparison of the reactivity at the 4 and 1′ positions

The 1′,4,6′-trisulphonate 2, obtained by mesylation of sucrose 2,3,3′,4′,6-penta-acetate (1), undergoes nucleophilic substitution with sodium benzoate in hexamethylphosphoric triamide at positions 1′,4, and 6′ to give 1,6-di-O-benzoyl-β-D-fructofuranosyl 4-O-benzoyl-α-D-galactopyranoside penta-acetate (3), and selectively at positions 4 and 6′ to give 6-O-benzoyl-1-O-mesyl-β-D-fructofuranosyl 4-O-benzoyl-α-D-galactopyranoside penta-acetate (4). The products 3 and 4 were identified from their ¹H-n.m.r. spectra and by O-deacylation to give β-D-fructofuranosyl α-D-galactopyranoside (5) and its 1-methanesulphonate 6, respectively. Treatment of the trisulphonate 2 with sodium azide gave analogous products, namely, 1,6-diazido-1,6-dideoxy-β-D-fructofuranosyl 4-azido-4-deoxy-α-D-galactopyranoside penta-acetate (8) and 6-azido-6-deoxy-1-O-mesyl-β-D-fructofuranosyl 4-azido-4-deoxy-α-D-galactopyranoside penta-acetate (7).     

Sesquiterpenoids and lignans from the fruits of Illicium simonsii Maxim

Twenty-two known compounds were isolated from the 95% alcohol extract of the fruits of Illicium simonsii Maxim, including seven sesquiterpenoids (16–22) and fifteen lignans (1–15). In the present research, compounds 3 ((7S,8R,8′S)-3,3′-dimethoxy-4,4′,9-trihydroxy-7,9′-epoxylignan-7′-one), 4 ((−)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one), 5 ((+)-8-hydroxypinoresinol), 6 ((+)-8-hydroxymedioresinol), 8 ((2R,3R)-2β-(4″-hydroxy-3″-methoxybenzyl)-3α-(4′-hydroxy-3′-methoxybenzyl)-γ-butyrolactone 2-O-(β-D-glucopyranoside), 12 ((+)-8-methoxyisolariciresinol), 13 (α-conidendrin), 14 (boehmenan) and 15 (7R,8R,7′E-7′,8′-didehydro-4,7,9,9′- tetrahydroxy-3-methoxy-8-O-4′-neolignan) were reported from the Illicium genus for the first time, and compounds 1 (simulanol), 7 ((+)-secoisolariciresinol monoglucoside), 10 ((+)-9-O-β-D-glucopyranosyl lyoniresinol), 11 ((+)-isolariciresinol), 18 (neoanisatin), 19 (veranisatin A), 20 (4,5-d₂-8′-oxo-dihydrophaseic acid) and 22 (Oligandrumin A) were firstly isolated from the plant. Their structures were elucidated on the basis of NMR spectroscopic and mass spectrometric data. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.     

Synthesis of 6-substituted uridines. synthesis of (R or S)-6-(3-amino-2-carboxypropyl)uridine

Addition of 5-bromo-2′,3′-O-isopropylidene-5′-O-trityluridine (2) in pyridine to an excess of 2-lithio-1,3-dithiane (3) in oxolane at 78° gave (6R)-5,6-dihydro-(1,3-dithian-2-yl)-2′,3′-O-isopropylidene -5′-O-trityluridine (4), (5S,6S)-5-bromo-5,6-dihydro-(1,3-dithian-2-yl)-2′,3′-O-isopropylidene-5′-O-trityluridine (5), and its (5R) isomer 6 in yields of 37, 35, and 10%, respectively. The structure of 4 was proved by Raney nickel desulphurization to (6S)-5,6-dihydro-2′,3′-O-isopropylidene-6-methyl-5′-O-trityluridine (7) and by acid hydrolysis to give D-ribose and (6R)-5,6-dihydro-6-(1,3-dithian-2-yl)uracil (9). Treatment of 4 with methyl iodide in aqueous acetone gave a 30&%; yield of (R,S)-5,6-dihydro-6-formyl-2′,3′-O-isopropylidene-5′-O-trityl-uridine (10), characterized as its semicarbazone 11. Both 5 and 6 gave 4 upon brief treatment with Raney nickel. Both 5 and 6 also gave 6-formyl-2′,3′-O-isopropylidene-5′- O-trityluridine (12) in ～41%; yield when treated with methyl iodide in aqueous acetone containin- 10%; dimethyl sulfoxide. A by-product, identified as the N-methyl derivative (13) of 12 was also formed in yields which varied with the amount of dimethyl sulfoxide used. Reduction of 12 with sodium borohydride, followed by deprotection, afforded 6-(hydroxymethyl)uridine (17), characterized by hydrolysis to the known 6-(hydroxymethyl)uracil (18). Knoevenagel condensation of a mixture of the aldehydes 12 and 13 with ethyl cyanoacetate yielded 38%; of E- (or Z-)6-[(2-cyano-2-ethoxycarbonyl)ethylidene]-2′,3′-O-isopropylidene-5′-O-trityluridine (19) and 10%; of its N-methyl derivative 20. Hydrogenation of 19 over platinum oxide in acetic anhydride followed by deprotection gave R (or S)-6-(3-amino-2-carboxypropyl)uridine (23).     

A chalcone glycoside from Abies pindrow

The EtOH extract of air-dried stems of Abies pindrow yielded okanin, okanin 4′-O-β-d-glucopyranoside, butein 4′-O-β-d-glucopyranoside, 8,3′4′-trihydroxyflavanone-7-O-β-d-glucopyranoside and a new chalcone glycoside, 2′,3′,4′:3,4-pentahydroxy-chalcone 4′-(l-arabinofuranosyl-α-1→4-d-glucopyranoside-β).     

Biosynthesis of the 6-oxygenated isoflavone afrormosin in Onobrychis viciifolia

dl-Phenylalanine-[2-¹⁴C], 2′,4′,4-trihydroxychalcone-[carbonyl-¹⁴C] and formononetin-[Me-¹⁴C] were all good precursors of afrormosin (7-hydroxy-6,4′-dimethoxyisoflavone) in Onobrychis viciifolia seedlings. This demonstrates that 6-oxygenation may be a late process in the biosynthesis of isoflavones.     

Dilignol glycosides from needles of Picea abies

(2R,3R)-2 3-Dihydro-2-(4′-hydroxy-3′-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-5-benzofuranpropanol 4′-O-β-d-glucopyranoside [dihydrodehydrodiconiferyl alcohol glucoside], (2R,3R)-2 3-dihydro-7-hydroxy-2-(4′-hydroxy-3′-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranpropanol 4′-O-β-d-glucopyranoside and 4′-O-α-l-rhamnopyranoside, 1-(4′-hydroxy-3′-methoxyphenyl)-2- [2″-hydroxy-4″-(3-hydroxypropyl)phenoxy]-1, 3-propanediol 1-O-β-d-glucopyranoside and 4′-O-β-d-xylopyranoside, 2,3-bis[(4′-hydroxy-3′-methoxyphenyl)-methyl]-1,4-butanediol 1-O-β-d-glucopyranoside [(?)-seco-isolariciresinol glucoside] and (1R,2S,3S)-1,2,3,4-tetrahydro-7-hydroxy-1-(4′-hydroxy-3′-methoxyphenyl)-6-methoxy-2 3-naphthalenedimethanol α²-O-β-d-xylopyranoside [(?)-isolariciresinol xyloside] have been isolated from needles of Picea abies and identified.     

Isolation and purification of flavonoid glucosides from Radix Astragali by high-speed counter-current chromatography

High-speed counter-current chromatography methods, combined with resin chromatography were applied to the separation and purification of flavonoid glycosides from the Chinese medicinal herb, Radix Astragali. Five flavonoid glycosides, namely calycosin-7-O-β-d-glucoside, ononin, (6aR, 11aR)-9,10-dimethoxypterocarpan-3-O-β-d-glucoside, (3R)-2′-hydroxy-3′,4′-dimethoxyisoflavan-7-O-β-d-glucoside and calycosin-7-O-β-d-glucoside-6′′-O-acetate, were obtained. Among them, calycosin-7-O-β-d-glucoside-6′′-O-acetate was preparatively separated from Radix Astragali for the first time. Their structures were identified by ESI–MS, ¹H NMR, ¹³C NMR, and 2D NMR.     

Biosynthesis of pterocarpan,isoflavan and coumestan metabolites of Medicago sativa: chalcone,isoflavone and isoflavanone precursors

Comparative feeding experiments in CuCl₂,- and UV-treated lucerne (Medicago sativa) seedlings have shown that 2′,4,4′-trihydroxychalcone-[carbonyl-¹⁴C] and formononetin-[Me-¹⁴C] but not 2′,4′-dihydroxy-4-methoxychalcone-[carbonyl- ¹⁴C] or daidzein-[4-¹⁴C] were incorporated into the phytoalexins demethylhomopterocarpin, sativan and vestitol, and also into 9-O-methylcoumestrol. The synthesis of 9-O-methylcoumestrol is greatly stimulated by this abiotic treatment but coumestrol production is not noticeably affected. Daidzein and the trihydroxychalcone were precursors of coumestrol. The results are interpreted in favour of a mechanism in which methylation is an integral part of the aryl migration process associated with the biosynthesisof 4′-methoxyisoflavonoids. Formononetin, 2′,7-dihydroxy-4′-methoxyisoflavone-[Me-¹⁴C], 7-hydroxy-4′-methoxyisoflavanone-[Me-¹⁴C] and 2′,7-dihydroxy-4′-methoxyisoflavanone-[Me-¹⁴C] were all excellent precursors of demethylhomopterocarpin, sativan, vestitol and 9-O-methylcoumestrol, and thus a metabolic grid may be involved in their biosynthetic origin.     

Chemical modification of the nonreducing,terminal group of maltotriose

O-α-d-Galactopyranosyl-(1→4)-O-α-d-glucopyranosyl-(1→4)-d-glucopyranose (12) was prepared by inversion of configuration at C-4″ of 2,3,2′,3′,6′,2″,3″-hepta-O-acetyl-1,6-anhydro-4″,6″-di-O-methylsulfonyl-β-maltotriose (7), followed by O-deacylation, acetylation, acetolysis, and de-O-acetylation. The intermediate 7 was obtained by treatment of 1,6-anhydro-β-maltotriose (2) with benzal chloride in pyridine, followed by acetylation, removal of the benzylidene group, and methane-sulfonylation. Selective tritylation of 2 and subsequent acetylation afforded 2,3,2′,3′,6′,2″,3″,4″-octa-O-acetyl-1,6-anhydro-6″-O-trityl-β-maltotriose (6), which was O-detritylated and p-toluenesulfonylated to give 2,3,2′,3′,6′,2″,3″,4″-octa-O-acetyl-1,6-anhydro-6″-O-p-tolylsulfonyl-β-maltotriose (13). Nucleophilic displacement of 13 with thioacetate, iodide, bromide, chloride, and azide ions gave 6″-S-acetyl- (14), 6″-iodo- (15), 6″-bromo- (16), 6″-chloro- (19), and 6″-azido- (20) 1,6-anhydro-β-maltotriose octaacetates, respectively. 6″Deoxy- (18) and 6″-acetamido-6″-deoxy (21) derivatives of 1,6-anhydro-β-maltotriose decaacetates were also prepared from 15 and 16, and 20, respectively. Acetolysis of 14, 15, 16, 18, 19, and 21 afforded 1,2,3,6,2′,3′,6′,2″,3″,4″-deca-O-acetyl-6″-S-acetyl (22), -6″-iodo (23), -6″-bromo (24), -6″-deoxy (25), -6″-chloro (26), and -6″-acetamido-6′-deoxy (27) derivatives of α-maltotriose, respectively. O-Deacetylation of 24, 25, and 26 furnished 6″-bromo-(28), 6″-deoxy- (29), and 6″-chloro- (30) maltotrioses, respectively, which on acetylation gave the corresponding β-decaacetates.     

Synthesis and plant growth inhibitory activities of (+)- and (−)-(2Z,4E)-5-(1′,2′-epoxy-2′,6′,6′-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid

Chiral (+)- and (?)-enantiomers of (2Z,4E)-5-(1′,2′-epoxy-2′,6′,6′-trimethylcyclohexyl)-3-methyl-2,4-pentadienoic acid have been synthesized from the chiral epoxy alcohols (+)- and (?)-1′,2′-dihydro-1′,2′-epoxy-β-ionone, which were prepared by Katsuki-Sharpless' asymmetric epoxidation of β-cyclogeraniol. The (+)-enantiomer showed strong inhibitory activity in a rice seedling and lettuce germination assay, whereas the (?)-enantiomer was 10³-times less active.     

5-Methyl ether flavone glucosides from the leaves of Bruguiera gymnorrhiza

Two new 5-methyl ether flavone glucosides (7,4′,5′-trihydroxy-5,3′-dimethoxyflavone 7-O-β-D-glucopyranoside and 7,4′-dihydroxy-5-methoxyflavone 7-O-β-D-glucopyranoside) were isolated from the leaves of Thai mangrove Bruguiera gymnorrhiza together with 7,3′,4′,5′-tetrahydroxy-5-methoxyflavone, 7,4′,5′-trihydroxy-5,3′-dimethoxyflavone, luteolin 5-methyl ether 7-O-β-D-glucopyranoside, 7,4′-dihydroxy-5,3′-dimethoxyflavone 7-O-β-D-glucopyranoside, quercetin 3-O-β-D-glucopyranoside, rutin, kaempferol 3-O-rutinoside, myricetin 3-O-rutinoside and an aryl-tetralin lignan rhamnoside. The structure of a lignan rhamnoside was found to be related to racemiside, an isolated compound from Cotoneaster racemiflora, and also discussed. Structure determinations were based on analyses of physical and spectroscopic data including 1D- and 2D-NMR.