Lasianthionosides A-C, megastigmane glucosides from leaves of Lasianthus fordii

From the leaves of Lasianthus fordii, three megastigmane glucosides, lasianthionosides A, B and C, were isolated together with the known iridoid glucoside, asperuloside, deacetylasperuloside and methyl deacetyl-asperulosidate, and a megastigmane glucoside, citroside A. The structures have been elucidated based on spectroscopic analyses and/or X-ray crystallographic analysis.     

Steroidal saponins from Smilax china and their anti-inflammatory activities

Steroidal saponins, 1, 2, 3 and 4, were isolated from the BuOH extract of Smilax china L., along with 13 known compounds, 5-17. Their structures were elucidated on the basis of MS, 1D and 2D NMR spectroscopic analyses and chemical evidence. In the bioassay tests, all compounds showed inhibitory effects on cyclooxygenase-2 enzyme (COX-2) activities at final concentration of 10(-5) M, and only compound 5 showed an inhibitory effect on production of TNFalpha (tumor necrosis factor alpha) in murine peritoneal macrophages at the same concentration.     

Diterpenoid glucosides from Salvia greggii

The structure of four diterpenoid glucosides, designated as salvigresides A-D (1-4), isolated from the aerial parts of Salvia greggii, have been confirmed by spectroscopic and chemical investigation.     

Chromone and chromanone glucosides from Hypericumsikokumontanum and their anti-Helicobacter pylori activities

Chromone glucosides, takanechromones A-C (1, 2 and 5) and chromanone glucosides, named takanechromanones A and B (3 and 4), were isolated from the methanolic extracts of Hypericumsikokumontanum together with 27 known compounds. Their structures were established based on spectroscopic evidence. The isolated compounds and some chromone derivatives were assayed for antimicrobial activity against Helicobacter pylori and cytotoxicity against human cancer cell lines.     

穿鞘菝葜的化学成分

从穿鞘菝葜(SmilaxperfoliataLour.)的95%乙醇提取物的乙酸乙酯萃取部分分离得到6个化合物,其中有一个新化合物smilglasideF(1)。经过核磁共振、质谱、红外光谱及化学手段鉴定了它们的结构。5个已知化合物分别是:芦丁(2)、3'-甲醚芦丁(3)、cassiaminA(4)、cassiaminB(5)和1,2,3-trimethoxy-5-hydroxyphenol-1-O-b-D-glucopyranoside(6)。其中化合物2、4~6是首次从该属植物分离得到。     

Tricalysiosides H-O: Ent-kaurane glucosides from the leaves of Tricalysia dubia

Eight ent-kaurane glucosides, named tricalysiosides H-O, were isolated from Tricalysia dubia. Tricalysioside H possessed a hydroxyl group at the 1-position, to which the glucose moiety was attached. The structure was first elucidated by means of spectroscopic data analysis and finally confirmed by X-ray crystallography. Since acid hydrolysis of 1 gave D-glucose, the aglycone was proved to have an enantio-kaurane type skeleton. The structures of tricalysiosides I-O were mainly elucidated from analysis of spectroscopic evidence.     

Lanceocrepidiasides A-F, glucosides of guaiane-type sesquiterpene from Crepidiastrum lanceolatum

From the aerial parts of Crepidiastrum lanceolatum, six guaiane-type sesquiterpene glucosides, lanceocripidiasides A-F were isolated together with five known sesquiterpene glucosides, ixerin Y, crepidialanceosides A and B, and youngiasides A and D, two known megastigmane glucosides, icariside B1 and corchoionoside A, and benzyl 6'-O-beta-D-apiofuranosyl-beta-D-glucopyranoside. Structures were elucidated by spectroscopic analyses.     

Chlorine-containing iridoid and iridoid glucoside, and other glucosides from leaves of Myoporum bontioides

Sixteen compounds were isolated from the MeOH extract of leaves of Myoporum bontioides. The five compounds hitherto unknown, were elucidated to be a chlorine-containing iridoid, named myopochlorin, and an iridoid glucoside, an acylated iridoid glucoside, a linear acetogenin glucoside, and an acyclic monoterpene glucoside, named myobontiosides A-D, respectively, by means of spectroscopic analyses.     

Acylated iridoid glucosides from Veronica anagallis-aquatica

Three new (1-3) and four known iridoid glucosides (4-7) as well as a known phenylethanoid glycoside (8) were isolated from the aerial parts of Veronica anagallis-aquatica and their structures were determined as 6'-O-benzoyl-8-epiloganic acid named aquaticoside A (1), 6'-O-p-hydroxybenzoyl-8-epiloganic acid named aquaticoside B (2), 6'-O-benzoyl-gardoside named aquaticoside C (3), veronicoside (4), catalposide (5), verproside (6), verminoside (7) and martynoside (8) on the basis of 1D and 2D NMR spectral analysis.     

Grevillosides A-F: glucosides of 5-alkylresorcinol derivatives from leaves of Grevillea robusta

From a MeOH extract of leaves of Grevillea robusta, seven compounds (1-7) were isolated. One known compound (7) was identified with a benzyl glucoside, icariside F₂. The structures of the six of these, named grevillosides A-F (1-6), were elucidated on detailed inspection of one- and two-dimensional NMR spectroscopic data as glucosides of 5-alkylresorcinols.     

穿鞘菝葜的化学成分

从穿鞘菝葜(Smilax perfoliata Lour.)的95%乙醇提取物的乙酸乙酯萃取部分分离得到6个化合物,其中有一个新化合物smilglaside F(1).经过核磁共振、质谱、红外光谱及化学手段鉴定了它们的结构.5个已知化合物分别是:芦丁(2)、3′-甲醚芦丁(3)、cassiamin A(4)、cassiamin B(5)和1,2,3-trimethoxy-5-hydroxyphenol-1-O-β-D-glucopyranoside(6).其中化合物2、4～6是首次从该属植物分离得到.     

Generation of primary amide glucosides from cyanogenic glucosides

The cyanogenic glucoside-related compound prunasinamide, (2R)-β-d-glucopyranosyloxyacetamide, has been detected in dried, but not in fresh leaves of the prunasin-containing species Olinia ventosa, Prunus laurocerasus, Pteridium aquilinium and Holocalyx balansae. Experiments with leaves of O. ventosa indicated a connection between amide generation and an excessive production of reactive oxygen species. In vitro, the Radziszewski reaction with H₂O₂ has been performed to yield high amounts of prunasinamide from prunasin. This reaction is suggested to produce primary amides from cyanogenic glycosides in drying and decaying leaves. Two different benzoic acid esters which may be connected to prunasin metabolism were isolated and identified as the main constituents of chlorotic leaves from O. ventosa and P. laurocerasus.     

Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium

From Glochidion zeylanicum, two megastigmane glucosides, 3- and 9-O-beta-D-glucopyranosides of (3S,5R,6R,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol (1 and 2, respectively), were isolated. Their structures were different from those of kiwiionoside (3) and actinidioionoside (4), isolated from Actinidia chinensis and Actinidia polygama, respectively, in the stereochemistry at the 9-positions. Alangionosides E (5) and O (6), isolated from the leaves of Alangium premnifolium, are also megastigmane glucosides, and the latter is closely related to 1 and actinidioionoside (4). However, the absolute configurations of the 9-position remained to be determined. They were analyzed to be R by means of a modified Mosher's method. Alangionoside E (5) is identical with corchoionoside A in all aspects. The name of corchoionoside A must be retained thereafter.     

Cytotoxic naphthoquinones and plumbagic acid glucosides from Plumbago zeylanica

Two plumbagic acid glucosides, 3'-O-beta-glucopyranosyl plumbagic acid and 3'-O-beta-glucopyranosyl plumbagic acid methylester along with five naphthoquinones (plumbagin, chitranone, maritinone, elliptinone and isoshinanolone), and five coumarins (seselin, 5-methoxyseselin, suberosin, xanthyletin and xanthoxyletin) were isolated from the roots of Plumbago zeylanica. All coumarins were not previously found in this plant. Cytotoxicity of these compounds to various tumor cells lines was evaluated, and plumbagin significantly suppressed growth of Raji, Calu-1, HeLa, and Wish tumor cell lines.     

Nitrile glucosides and serotobenine from Campylospermum glaucum and Ouratea turnarea

Two nitrile glucosides (1S,3S,4S,5R)-4-benzoyloxy-2-cyanomethylene-3,5-dihydroxycyclohexyl-1-O-beta-glucopyranoside (campyloside A) and (1S,3S,4S,5R)-5-benzoyloxy-2-cyanomethylene-3-hydroxy-4-(2-pyrrolcarboxyloxy)cyclohexyl-1-O-beta-glucopyranoside (campyloside B) were isolated from the stem roots of Campylospermum glaucum, whereas serotobenine was isolated from Ouratea turnarea. The structure elucidations were based on spectroscopic evidence. The biological assays of compounds and crude extract of plant species showed good antimicrobial activity of crude extracts against Gram-positive cocci.     

Antioxidant phenylpropanoid glycosides from Smilax bracteata

From the ethanolic extract of Smilax bracteata, six phenylpropanoid glycosides, smilasides G-L (1-6), along with four known phenylpropanoid compounds, helonioside A, helonioside B, smilaside E, and (1-p-O-coumaroyl-6-O-feruroyl)-beta-d-fructofuranosyl-alpha-d-glucopyranoside, and fourteen known phenolic compounds were isolated. Their structures were elucidated on the basis of spectroscopic analyses. Moreover, 1-6 exhibited moderate scavenging activities against DPPH radicals.     

Euodionosides A-G: megastigmane glucosides from leaves of Euodia meliaefolia

From a 1-BuOH-soluble fraction of the MeOH extract of leaves of Euodia meliaefolia, collected in Okinawa, seven megastigmane glucosides, named euodionosides A-G, were isolated together with three known megastgmane glucosides, and two aliphatic and three phenolic compounds. Their structures were elucidated through a combination of spectroscopic analyses and application of the modified Mosher's method.     

Oligomeric secoiridoid glucosides from Jasminum abyssinicum

From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A-C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations.     

C14-Oxylipin glucosides isolated from Lemna paucicostata

Oxylipin glucosides (2-4) were isolated from Lemna paucicostata with their structures and absolute configurations elucidated by spectroscopic and chemical methods. Compounds 2-4 were glucosides of C₁₄ oxylipin which were synthesized from α-linolenic acid via the 9-lipoxygenase pathway.