Discovery of sesquiterpene from Youngia japonica with antitumor effect.

Fourteen sesquiterpenes, including one undescribed sesquiterpene lactone, were isolated from Youngia japonica, and their structures were identified by NMR, HRESIMS, ECD and calculated ECD. Cytotoxic activities of all isolates against A549, HeLa, and 4 T1 cell lines were detected by CCK8 assay. Among them, 2 showed obvious cytotoxic activity against A549 cells. Subsequently, the production of ROS, and apoptosis of A549 cells treated with 2 were evaluated. The result showed that 2 distinctly increased the ROS level, and induced the apoptosis of A549 cells. Further anticancer mechanism studies showed that 2 increased the expression of cleaved caspase 3. Taken together, our results demonstrated that 2 might become potential leading compounds for the treatment of lung cancer.

Secoiridoid dimers and their biogenetic precursors from the fruits of Cornus officinalis with potential therapeutic effects on type 2 diabetes.

Cornusdiridoid A-F (1-6), six unusual cornuside-morroniside secoiridoid dimers, and their possible new biogenetic precursor, 3″,5″-dehydroxycornuside (7), together with four known secoiridoids (8-11), were obtained from the fruits of Cornus officinalis. Their structures were elucidated on the basis of various spectroscopic and chemical methods. A plausible biosynthetic pathway of compounds 1-11 was proposed. The α-glucosidase inhibitory, antioxidant and anti-inflammatory activities of these isolates were evaluated. Some of them emerged out as potent antidiabetic, anti-inflammatory and free radical scavenging agents. Molecular docking was also carried out for antidiabetic target α-glucosidase to investigate the possible binding modes of the most potent α-glucosidase inhibitor, vincosamide (9). These results revealed that the secoiridoids from C. officinalis fruits may be served as new potential antidiabetic agents to prevent and treat type 2 diabetes.

Cytotoxic compound triacremoniate from Marine Fungus Acremonium citrinum. MMF4.

Two new compounds, triacremoniate (1) and dietziamide C (2) along with known compounds ß-Adenosine (3) and acrepyrone A (4) were obtained from the mangrove-derived fungus Acremonium citrinum. MMF4. Their structures were unambiguously determined by extensive spectroscopic methods, including UV, IR, HRESIMS and NMR. Triacremoniate (1) can promote apoptosis of HeLa cells by increasing the PARP cleavage and the phosphorylation of JNK and p38.

Undescribed morroniside-like secoiridoid diglycosides with α-glucosidase inhibitory activity from Corni Fructus.

Corni Fructus, also known as the fruit of Cornus officinalis Sieb. et Zucc., has long been used as a traditional Chinese medicine and is widely consumed as a nutritional food in the form of function drink and wine. Recently, Corni Fructus has attracted considerable interest because of its anti-diabetic effects. A systematic phytochemical investigation of Corni Fructus was performed to find anti-diabetic components, which led to the isolation of 10 unreported iridoid glycosides, cornusdiglycosides A-J (1-8, 9a/9b and 10a/10b). Their chemical structures were determined through spectroscopic analysis (ultraviolet [UV], infrared [IR], high-resolution electrospray ionisation mass spectroscopy [HRESIMS], one-dimensional [1D] and two-dimensional [2D] nuclear magnetic resonance [NMR]). Such morroniside-type diglycosides were first reported from natural sources, and all isolates were evaluated for α-glucosidase inhibitory activity. The results showed that all compounds (1-10) exhibited α-glucosidase (from Saccharomyces cerevisiae) inhibitory activities with IC50 values ranging from 78.9 ± 4.09 to 162.2 ± 9.17 µM, whereas acarbose, the positive control, displayed α-glucosidase inhibitory activity with IC50 value of 118.9 ± 7.89 µM.

[A new phenylpropanoid glycoside from fruit of Cornus officinalis].

To investigate the chemical compounds from the ripe fruit of Cornus officinalis, a new phenylpropanoid glycoside 1-O-(6'-O-p-hydroxybenzoyl-ß-D-glucopyranosyl)-p-phenylpropanol, named cornuphenylpropanoid A (1), were separated and purified by D101 macroporous resin, silica gel and ODS column chromatography. Its structure was extensively determined on basis of ¹H-NMR, ¹³C-NMR, DEPT, HSQC, HMBC and HR-ESI-MS spectroscopic data.

Cornusides A-O, Bioactive Iridoid Glucoside Dimers from the Fruit of Cornus officinalis.

Fifteen new and rare iridoid glucoside dimers, cornusides A-O (1-15), and 10 known iridoid glucosides (16-25) were isolated from the fruit of Cornus officinalis. These new chemical structures were established through spectroscopic analysis (UV, IR, HRESIMS, 1D and 2D NMR). Compounds 1-25 were tested for their inhibitory activities by measuring IL-6-induced STAT3 promoter activity in HepG2 cells, and 3, 12, 17, 22, and 23 showed inhibitory effects, with IC50 values of 11.9, 12.2, 14.0, 7.0, and 6.9 µM, respectively.

Four new iridoid glucosides containing the furan ring from the fruit of Cornus officinalis.

Four new and rare iridoid glucosides, cornusfuroside A-D (1-4), containing the furan ring were identified from water extract of the fruit of Cornus officinalis. These new chemical structures were determined through extensive spectroscopic analysis, including 1D and 2D NMR, IR, HRESIMS, experimental and calculated electronic circular dichroism (ECD). Notably, this study is the first report on the isolation of four iridoid glucoside structures with acetal functions in the sugar moiety. The neuroprotective effects of these compounds were also evaluated in vitro.

[Chemical constituents from ripe fruit of Cornus officinalis].

To investigate the chemical compounds from the fruit of Cornus officinalis, six compounds were isolated and determined by extensive spectroscopic analysis as 6'-O-acetyl-7α-O-ethyl morroniside (1), (-)-isolariciresinol 3α-O-ß-D-glucopyranoside(2), apigenin (3), cirsiumaldehyde(4), p-coumaric acid (5), caffeic acid (6). Compound 1 was a new iridoid glucoside,and compounds 2-4 were obtained from the Cornus genus for the first time. Compounds 2-6 were evaluated for the viability of PC12 cells when exposed in conditions of oxygen and glucose deprivation. The MTT results showed that compound 4 increased cell viability moderately in OGD/R treated PC12 cells at the concentration of 1.0 µmol•L⁻¹.

Chemical constituents from twigs of Euonymus alatus.

To investigate the chemical compounds from the twigs of Euonymus alatus, nine compounds were isolated and identified as(+)-delta(2,11)-enaminousnic acid(1), 11-keto-beta-boswellic acid(2), acetyl 11-keto-beta-boswellic acid(3), camaldulenic acid(4), betulinic acid(5), 6beta-hydroxy-stigmast-4-en-3-one(6), 5-hydroxy-6,7-dimethoxyflavone(7), ethyl 2,4-dihydroxy-6-methylbenzoate(8), 4,4'-dimethoxy-1,1'-biphenyl(9). Their structures were elucidated by extensive spectroscopic analysis. Among them, compound 1 was a new natural product. Compounds 2-4 and 7-9 were obtained from the Euonymus genus for the first time. In vitro study showed that compounds 2 and 3 showed significant anti-tumor activities to BEL-7402 and HCT-8 at the concentration of 10 mg x L(-1). The inhibition rate of compound 2 was 61.78% and 68.29%, whereas the inhibition rate of compound 3 had reached to 70.91% and 84.07%.

[A new benzaldehyde from aerial part of Rehmannia glutinosa].

A new benzaldehyde, 3-hydroxy-4-(4-(2-hydroxyethyl) phenoxy) henzaldehyde(1), together with six known compounds, including isovanillic acid(2), pyrocatechol(3), glutinosalactone A(4), chrysoeriol(5), apigenin(6) and luteolin(7) were isolated from aerial part of Rehmannia glutinosa. The compounds were isolated by macroporous resin, silica gel, Sephadex LH-20 and HPLC chromatographies. The chemical structures of 1-7 were elucidated on the basis of spectral analysis (MS, 1D NMR and 2D NMR).

[Chemical constituents from aerial part of Rehmannia glutinosa].

To investigate the chemical compounds from aerial part of Rehmannia glutinosa, six compounds were isolated and deter- mined by extensive spectroscopic analysis as(+)-(7S, 8S, 8'S)-9-O-[ß-D-glucopyranoyl] asarininone(1), 2α,3ß,19α,23-tetrahydroxy-olean-12-en-28-oic acid(2),7,3'-dihydroxyl-5'-methoxyisoflavone (3), aeginetic acid (4), corchorifattty acid B (5), pinellic acid (6). Among them, compound 1 was a new natural product. Compounds 2, 3 and 5 were obtained from the Rehmannia genus for the first time. In vitro study showed that none of the six compounds exhibited obvious activities to BEL-7402 and HCT-8 at the concentration of 10 mg x L(-1).