Determination of a new chromone from Aurantii Fructus Immaturus by DFT/GIAO method

Investigation of EtOAc fraction from the 95% ethanol extract of Aurantii Fructus Immaturus led to the isolation of one new chromone (1) and seven known flavonoids (2–8). Their structures were elucidated mainly by NMR and HR-ESI-MS, as well as on comparison with the reported NMR data. The final substituent pattern of 1 was defined by comparison of ¹³C NMR data calculated by DFT/GIAO with those of experimental NMR data.     

New 2-(2-phenylethyl)chromone derivatives from agarwood and their inhibitory effects on tumor cells

Abstract

Two new chromone derivatives, 7-hydroxy-2-[2-(3'-methoxy-4'-hydroxyphenyl)-ethyl]chromone (1), and 6,7-dimethoxy-2-[2-(3'-hydroxyphenyl)-ethyl]chromone (2) were isolated from the EtOH extract of agarwood of Aquilaria sinensis, together with eleven known analogues. Their structures were established by detailed HR-ESIMS, 1D and 2D NMR spectroscopic analysis, as well as comparison with the literature data. Selected the isolates (1, 2, 4–8, 10, 11) were tested for their antitumor activities against SMMC-7721, MGC-803 and OV-90 cell lines using the MTT method with cisplatin and paclitaxel as the positive control. All the tested compounds showed weak cytotoxic activities with IC₅₀ values ranged from 18.82 to 37.95 µg/ml.     

Two new secoiridoid glycosides from the roots of Picrorhiza scrophulariiflora

From the roots ofPicrorhiza scrophulariiflora, two new secoifidoid glycosides, named picrosecosides Ⅰ and Ⅱ （1, 2） have been isolated. Their structures were elucidated on the basis of chemical and spectropic evidences.     

A new furan derivative from an endophytic Aspergillus flavus of Cephalotaxus fortunei

A new furan derivative named 5-acetoxymethylfuran-3-carboxylic acid (2), together with a known furan compound, 5-hydroxymethylfuran-3-carboxylic acid (1), were isolated from the fermentation of Aspergillus flavus, endophytic fungi in Cephalotaxus fortunei. The structures of 1 and 2 were elucidated by NMR, IR, UV and MS data, as well as compared with literature data. The compounds 1 and 2 exhibited potent antibacterial activity against Staphylococcus aureus with MIC values of 31.3 and 15.6 μg/mL, respectively. The compound 2 showed moderate antioxidant activity.     

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.     

Two new triterpenoid glycosides from the stems of Camellia oleifera Abel

Two new oleanane-type triterpenoid glycosides, 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-[β-D-glucuronopyranosyl-(1→2)]-β-D-glucuronopyranosyl-22α-angeloyloxyolean-12-ene-15α,16α,28-triol(1) and 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→3)-[β-D-glucuronopyranosyl-(1→2)]-β-D-glucuronopyranosyl-21β-acetyl-22α-angeloyloxyolean-12-ene-16α,28-diol (2) were isolated from the stems of Camellia oleifera Abel. Their structures were elucidated by means of spectroscopic methods and chemical evidence. The cytotoxic activities of compounds 1–2 were evaluated against five human tumour cell lines (HCT-8, BGC-823, A5049, and A2780). Compounds 1–2 showed cytotoxic activity against five human cancer cell lines, with IC₅₀ values ranging from 3.15 to 7.32 μM.     

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.     

A new hydroxybenzoic acid glycosides from the plant of Trifolium lupinaster

<正>A new 5-O-(β-D-glucopyranosyl)-6'-O-benzoyl-2,5-dihydroxybenzoic acid was isolated from the ethyl acetate extract from the whole plants of Trifolium lupinaster L.Its structure was determined and deduced on the basis of their spectral data.     

Two new kaempferol glycosides from the seeds of Camellia semiserrata Chi

Two new acetylated kaempferol glycosides were isolated from the seeds of Camellia semiserrata Chi,their structures were elucidated as kaempferol-3-O-[(3-O-acetyl)-α-L-rhamnopyranosyl(1→3)(4-O-acetyl)-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside] (1) and kaempferol-3-O-[(2-O-acetyl)-α-L-rhamnopyranosyl(1→3)(4-O-acetyl)-α-L-rhamnopyranosyl(1→6)-β-D-gluco -pyranoside](2) by spectral experiments(including ESI-MS,1D- and 2D-NMR).     

Two new ionone glycosides from the roots of Rehmannia glutinosa Libosch.

Two new ionone glycosides, named frehmaglutoside G (1) and frehmaglutoside H (2), together with six known compounds, rehmapicroside (3), sec-hydroxyaeginetic acid (4), dihydroxy-β-ionone (5), trihydroxy-β-ionone (6), rehmaionoside A (7) and rehmaionoside C (8), were isolated from the 95% EtOH extract of the dried roots of Rehmannia glutinosa Libosch. Their structures were determined on the basis of extensive spectroscopic analyses, including HR-ESI-MS, UV, IR, 1D and 2D NMR (¹H–¹H COSY, HSQC, HMBC and NOESY) methods. The absolute configurations were confirmed via the circular dichroism spectra.     

Two new tetralone glycosides from the green walnut husks of Juglans mandshurica Maxim

Two new tetralone glycosides, 4(S)-5-methoxy juglanoside A (1), 4(S)-5-methoxy juglanoside D (2), together with ten known compounds (3–12) have been isolated from the green walnut husks of Juglans mandshurica Maxim. Their structures were elucidated on the basis of their ESI-MS, 1?D and 2?D NMR spectroscopic data. In addition, all compounds were evaluated for their cytotoxic activities against the cancer BGC-823 (human gastric carcinoma), HCT-15 (human colorectal carcinoma) and K562 (human chronic myeloid leukemia) cell lines. The results showed aglycones of naphthoquinones had stronger cytotoxic activities than glycosides of tetralone.     

Five new benzophenone glycosides from the leaves of Aquilaria sinensis(Lour.) Gilg

Phytochemical investigation on the ethanol extract from the leaves of Aquitaria sinensis led to the isolation of five new benzophenone glycosides,aquilarinensides A-E(1-5).Their structures were elucidated by a combination of 1D and 2D NMR,HRMS,and chemical analysis.     

Two new polyacetylene glycosides from the roots of Codonopsis tangshen Oliv.

Two new polyacetylene glycosides, tangshenyne A (1) and tangshenyne B (2), along with six known polyacetylenes were isolated from an 85% MeOH extract of the roots of Codonopsis tangshen Oliv. The chemical structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including UV, IR, 1D and 2D NMR (¹H–¹H COSY, HSQC and HMBC) and HR-ESI-MS.     

Novel megastigmanes with lipid accumulation inhibitory and lipid metabolism-promoting activities in HepG2 cells from Sedum sarmentosum

Four novel megastigmanes, neosedumosides I (1), II (2), III (3), and IV (4) were isolated from the whole plant of Sedum sarmentosum (Crassulaceae). Absolute stereostructures of these constituents were determined on the basis of chemical and physicochemical evidence. Among them, 1-3 were found to show lipid accumulation inhibitory activity in HepG2 cells. Furthermore, 2 and 3 were found to also show lipid metabolism-promoting activity.     

Structure elucidation and NMR spectral assignments of three new lignan glycosides from Akebia trifoliata

Three new lignan glycosides (1-3) were isolated from the stems of Akebia trifoliata. Their structures were elucidated as (7R,8R,7'R,8'R)3,3',5,5'tetramethoxy-4,4'dihydroxy-7,9':7',9-diepoxylignan-4-O-beta-D-glucopyranoside (1), (7S,8S,8'R)-4,4',9-trihydroxy-3,3',5,5'-tetramethoxy-7,9'-epoxylignan-7'-one 9-O-beta-D-glucopyranoside (2), (7R,8R,8'S)-4,4',9-trihydroxy3,3',5,5'-tetramethoxy-7,9'-epoxylignan-7'-one 9-O-beta-D-glucopyranoside (3) by spectral analyses, primarily NMR, MS and CD. The NMR assignments for the compounds were carried out using 1H, 13C, DEPT, COSY, HSQC, HMBC and ROESY NMR experiments.     

Two new monoterpenoid glycosides from the fresh rhizome of Tongling White Ginger (Zingiber officinale)

Two new monoterpenoid glycosides, trans-1,8-cineole-3,6-dihydroxy-3-O-β-D-glucopyranoside (1), and 5,9-dihydroxy borneol 2-O-β-D-glucopyranoside (2), together with four known monoterpenoid glycosides (3–6), were isolated from the water-soluble constituents of the fresh rhizome of Tongling White Ginger (Zingiber officinale). Their structures were decisively elucidated by spectroscopic analysis. In vitro tests for antimicrobial activity showed that compounds 1 and 3 possess significant activity against two Gram-positive organisms, Staphylococcus aureus and Staphylococcus epidermidis.     

Two new glycosides isolated from Sapindus mukorossi fruits: effects on cell apoptosis and caspase-3 activation in human lung carcinoma cells

Two new glycosides (1, 2) and two saponins (3, 4) were isolated from the fruits of Sapindus mukorossi Gaertn. The two glycosides were designated as sapindoside G (1) and 4′′,4′′′′′-O-diacetylmukurozioside IIa (2). All four compounds exhibited inhibitory effects against A549 human lung adenocarcinoma cells with inhibition rates up to 69.2–83.3% at a concentration of 100 μg/mL. Flow cytometric analysis revealed that compounds 1–4 could suppress A549 cell growth by promoting cell apoptosis, which was related to the activation of caspase-3.     

Structure elucidation of two new unusual monoterpene glycosides from Euphorbia decipiens, by 1D and 2D NMR experiments

Two new unusual monoterpene glycosides, (Z)-3,6-dimethyl-3-(β-D-O-glucosylmethylene)cyclohept-4-ene-1-one (1) and 3,6-dimethyl-3-(β-D-O-glucosylmethylene)cycloheptanone (2) have been isolated along with five known compounds, 3-hydroxy-4-methoxybenzoic acid, 6,7-dihydroxycoumarin, luteolin, apigenin 5-O-αl-L-rhamnoside, and pinocembrin-7-O-rutinoside from ethyl acetate extract of Euphorbia decipiens. The structures of the isolated compounds were elucidated by extensive 1D- and 2D-NMR, and mass spectroscopic analyses.     

A novel phenylpropanoid glycosides and a new derivation of phenolic glycoside from Paris Polyphylla var. yunnanensis

A novel phenylpropanoid glycosides 1, named parispolyside F, and a novel derivation of phenolic glycoside 2, named parispolyside G, as well as two known flavonoid glycosides were isolated from the rhizome of Paris polyphylla var. yunnanensis. Their structures were elucidated by spectroscopic methods.     

A new flavonol glycoside from the flowers of Hosta plantaginea with cyclooxygenases-1/2 inhibitory and antioxidant activities

Hosta plantaginea was a traditional Chinese medicinal plants used to treat inflammatory and painful diseases with partial scientific validation. Solvent extractions followed by repeated chromatographic purification of the H. plantaginea flowers led to the isolation of one new flavonoid glycoside, hostaflavone A (1), together with one related known compound, kaempferol-3-O-sophoroside-7-O-glucoside (2), and their structures were elucidated on the basis of chemical and spectral evidence, as well as by comparison with literature data. Compounds 1 and 2 were evaluated for the anti-inflammatory activites against cyclooxygenases (COX-1 and COX-2) and DPPH free radical-scavenging activities in vitro. The results revealed that 1 and 2 exhibited significant COX-1 inhibition and moderate COX-2 inhibition compared to the reference celecoxib. Additionally, 1 and 2 displayed insignificant antioxidant activities compared to the positive control L-ascorbic acid.