Two new phenolic glycosides from Viscum articulatum

Two new phenolic glycosides, 1-O-benzyl-[5-O-benzoyl-beta-D-apiofuranosyl (1-->2)]-beta-D-glucopyranoside (1), and 4;-hydroxy-7,3;-dimethoxyflavan-5-O- beta-D-gluco-pyranoside (2), together with nine known flavanones 3 - 11, have been isolated from the dried whole plants of Viscum articulatum.Their structures were identified by extensive spectral analysis, especially 2D NMR techniques. Compound 9 showed weak anti-HIV-1 activity.     

Two new phenolic glycosides from the aerial parts of Androsace umbellata

Two new phenolic glycosides,2-hydroxy-4-O-β-D-glucopyranosylphenylacetic acid methyl acetate(1) and 2-hydroxy-4-O-β-D-glucopyranosylphenylacetic acid(2) were isolated from the aerial parts of Andwsace umbellata.Their structures were elucidated by spectral techniques.     

Three new nortriterpene glycosides and two new triterpene glycosides from the bulbs of Scilla scilloides

Three new norlanostane-type triterpene glycosides, scillanostasides A, B, and C, and two new lanostane-type triterpene glycosides, scillanostasides D and E, were isolated from the bulbs of Scilla scilloides Druce (Liliaceae) along with one known norlanostane-type triterpene heptaglycoside, scillascilloside G-1. Their chemical structures were determined on the basis of spectroscopic data as well as chemical evidence.     

Three new spirostanol glycosides from Helleborus thibetanus

Abstract

An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1?D, 2?D NMR spectra, together with IR and MS methods and acid hydrolysis. This is the first report of the isolation of spirostanol glycoside with xylose at C-24 of the aglycone in Helleborus.     

Three new 15,16-seco-cycloartane glycosides from Cimicifuga Rhizome

Three new 15,16-seco-cycloartane glycosides, which were constructed by a C-C bond cleavage in the D ring, have been isolated from Cimicifuga Rhizome for the first time. Their structures were determined by the use of 2D NMR techniques and chemical evidence.     

Three new caffeoyl glycosides from the roots of Picrorhiza scrophulariiflora

From the underground parts of Picrorhiza scrophulariiflora, three new caffeoyl glycosides, scrocaffeside A-C (1-3), together with two caffeic acid derivates, 4-O-beta-D-glucopyranosyl caffeic acid (4) and 4-methoxy caffeic acid (5) and a phenylethanoid glycoside, scroside D (6), were isolated. Their structures were elucidated on the basis of chemical and spectroscopic evidence and comparisons with literature data of related compounds.     

Three new steroidal glycosides from the roots of Cynanchum auriculatum

Three new steroidal glycosides, cyanoauriculosides F, G and H (1-3), were isolated from the roots of Cynanchum auriculatum (Asclepiadaceae) along with two known steroidal derivatives. On the basis of spectroscopic analysis and chemical methods, their structures were identified as 20-O-acetyl-8,14-seco-penupogenin-8-one 3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside (1), 2',3'-Z-gagaminine 3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaro-pyranosyl-(1→4)-α-L-diginopyranosyl-(1→4)-β-D-cymaropyranoside (2), 17-O-acetyl-kidjoranin 3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-cymaro-pyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-digitoxopyranoside (3), gagaminine 3-O-α-L-cymaropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-α-L-digino-pyranosyl-(1→4)-β-D-cymaropyranoside (4) and wilfoside D1N (5).     

Three new sulphur glycosides from the seeds of Descurainia sophia

Three new sulphur glycosides, raphanuside B–D (1–3), together with a known sulphur glycoside, raphanuside (4) were isolated from the decoction of the seeds of Descurainia sophia (L.) Webb ex Prantl, and the compound 4 was reported for the first time from this plant. Their structures were identified by means of UV, IR, 1D, 2D NMR (HSQC, HMBC and NOESY) and HR–ESI–MS spectroscopic data.     

Three new cycloartane triterpene glycosides from Souliea vaginata

Three new cycloartane triterpene glycosides, soulieosides A (1), B (2), and C (3), were isolated from the rhizomes of Souliea vaginata, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Soulieosides A-C were assigned as 25-O-acetylcimigenol-3-O-beta-D-(2-acetyl)xylopyranoside (1), 24-O-acetyl-isodahurinol-3-O-beta-D-(2-acetyl)xylopyranoside (2) and 20(S),22(R),23(S),24(R)-16beta:23;22:25-diepoxy-3beta,23,24-trihydroxy-9,19-cyclolanostane-3-O-beta-D-(4-acetyl)xylopyranoside (3), respectively.     

Three new oleanene glycosides from Sophora flavescens.

Three new oleanene glycosides, sophoraflavosides II-IV (2-4) were isolated together with sophoraflavoside I (1) as the corresponding methyl ester forms from Sophorae Radix, the fresh roots of Sophora flavescens AITON (Leguminosae). Their structures have been elucidated as oxytrogenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D- glucuronopyranoside (2), 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D-glucuronopyranosyl oxytrogenin 22-O-alpha-L-arabinopyranoside (3) and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->2)-beta -D-glucuronopyranosyl oxytrogenin 22-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranoside (4), along with unambiguous characterization as 3 beta,22 beta,24-trihydroxyolean-12-en-29-oic acid for their sapogenol, named oxytrogenin (5) on the bases of chemical reactions and spectral analyses.     

Three new flavonoid glycosides isolated from Elsholtzia bodinieri

Three new flavonoid glycosides, eriodictyol 7-O-(6'-feruloyl)-beta-D-glucopyranoside (1), eriodictyol 7-O-[6'-(3'-hydroxy-4'-methoxy cinnamoyl)]-beta-D-glucopyranoside (2), and luteolin 7-O-[6'-(3'-hydroxy-4'-methoxy cinnamoyl)]-beta-D-glucopyranoside (3), and eight known flavonoids were isolated from the whole plants of Elsholtzia bodinieri. The structures of the 3 new compounds were elucidated on the basis of extensive spectroscopic analysis.     

Three new phenolic glucosides from the roots of Rheum palmatum

A novel naphthalene glucoside, rheumone A (1), with an unprecedented skeleton containing a seven-membered lactone, and two new compounds, 1-O-phloroglucinyl-2-O-galloyl-6-O-cinnamoyl-β-D-glucoside (2) and chrysophanol 1-O-β-D-(6'-O-malonyl)glucoside (3), together with three known compounds (4-6) were isolated from the roots of Rheum palmatum. Their structures were elucidated mainly by spectroscopic analysis. These compounds were evaluated in vitro for their cytotoxicities towards human hepatocellular cancer cell lines Bel-7402 and Bel-7402/5Fu, and human gastric carcinoma cell line BGC-823. None of them showed cytotoxicity with IC(50) far beyond 50 μM.     

Three new naphthalenyl glycosides from the root bark of Juglans cathayensis

Phytochemical investigations of the root bark of Juglans cathayensis DODE. led to the isolation of three new naphthalenyl glycosides, Jugnaphthalenoside A-C (1-3). Their structures were elucidated on the basis of extensive analysis of spectroscopic data. The cytotoxicities of the three new compounds were also evaluated.     

Three new flavonol glycosides from the aerial parts of Rodgersia podophylla

Three new flavonol glycosides were isolated together with five known flavonoids and six bergenin derivatives from the aerial parts of Rodgersia podophylla. The structures of these new compounds were elucidated by spectral methods as kaempferol-3-O-alpha-L-5'-acetyl-arabinofuranoside (1), kaempferol 3-O-alpha-L-3'-acetyl-arabinofuranoside (2), and quercetin-3-O-alpha-L-3',5'-diacetyl-arabinofuranoside (3).     

Three new steroid glycosides from the underground parts of Trillium kamtschaticum

Three new steroid glycosides named trikamsterosides C, D and E were isolated from the underground parts of Trillium kamtschaticum PALL. (Liliaceae) along with two known 18-norspirostanol glycosides trillenosides A and B. Their chemical structures were determined on the basis of spectroscopic data and chemical evidence.     

Oplopanphesides A-C, three new phenolic glycosides from the root barks of Oplopanax horridus

Three new phenolic glycosides, named oplopanphesides A-C (1-3), have been isolated from the root barks of Oplopanax horridus. Their structures were elucidated by a combination of spectroscopic analyses, including 1D- and 2D-NMR techniques. These phenolic glycosides possess a novel feature in their sugar moieties that a 3-hydroxy-3-methylglutaryl moiety was connected with C-6 of the β-D-glucopyranosyl group. Those compounds showed no cytotoxic effects against human cancer cell lines (MDA-231 and MCF-7) by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method.     

New phenolic glycosides from the seeds of Cucurbita moschata

Five new phenolic glycosides, cucurbitosides A-E (1-5), were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as 2-(4-hydroxy)phenylethanol 4-O-(5-O-benzoyl)-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (1), 2-(4-hydroxyphenyl)ethanol 4-O-[5-O-(4-hydroxy)benzoyl]-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (2), 4-hydroxybenzyl alcohol 4-O-(5-O-benzoyl)-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (3), 4-hydroxybenzyl alcohol 4-O-[5-O-(4-hydroxy)benzoyl]-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (4) and 4-hydroxyphenyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (5) on the basis of spectroscopic analysis and chemical evidence.     

Three new C21 steroidal glycosides from the roots of Cynanchum inamoenum

Three new C_(21) steroidal glycosides named inamoside E (1),inamoside F (2) and inamoside G (3) were isolated from the roots of Cynanchum inamoenum (Maxim.) Loes.Their structures were determined by spectroscopic analysis,especially by 1D and 2D NMR experiments.     

Three new and antitumor anthraquinone glycosides from Lasianthus acuminatissimus MERR

Three new anthraquinone glycosides, lasianthuoside A (1), B (2), and C (3), were isolated from the root of Lasianthus acuminatissimus MERR., The structural elucidation of these anthraquinones was mainly established on the basis of 1D and 2D NMR and HR-MS spectroscopic analysis. Ten known compounds, damnacanthol (4), damnacanthol 11-methyl ether (5), damnacanthol-3-O-beta-D-primeveroside (6), asperuloside (7), asperulosidic acid (8), deacetyl asperulosidic acid (9), a nonglycosidic iridoid (10), 2,6-dimethoxy-4-hydroxyphenol-1-O-beta-D-glucopyranoside (11), tachioside (methoxyhydroquinone-4-O-beta-D-glucopyranoside) (12), and isotachioside (methoxyhydroquinone-1-O-beta-D-glucopyranoside) (13) were also identified for the first time from this plant in the course of the phytochemical and spectroscopic investigation. In addition to this report, a preliminary evaluation of 13 compounds in treating rheumatoid arthritis and antitumor effects of six anthraquinones are presented.     

Two new phenolic glycosides from Viburnum plicatum var. plicatum f. plicatum

Two new glycosides, named dideoxyplicatumoside A (1) and erythro-syringylglycerol-beta-O-4'-(+)-isoeucommin A 4'-O-beta-D-glucopyranoside (2), together with seven known compounds, were isolated from the leaves of Viburnum plicatum Thunb. ex Murray var. plicatum f. plicatum. Their structures were established on the basis of NMR, MS and chemical data.