Three New Diterpenoids from Isodon nervosus

Three new ent‐kaurane diterpenoids, rabdonervosins D–F ( 1 – 3 ), were isolated from the leaves and stems of Isodon nervosus. Their structures were elucidated on the basis of spectroscopic methods including 1D‐ and 2D‐NMR analyses. Compounds 1 – 3 were evaluated for their cytotoxicity against HepG2, CNE2, PC‐9/ZD, HeLa, MCF‐7, and HCT116 cell lines. No compounds exhibited potent cytotoxicity.     

A new phenylethanoid glycoside from Orobanche cernua Loefling

A novel phenylethanoid glycoside, 3′-O-methyl isocrenatoside (1), along with two known compounds, methyl caffeate (2) and protocatechuic aldehyde (3), were isolated from the fresh whole plant of Orobanche cernua Loefling. All the isolated compounds (1–3) were elucidated on the basis of spectroscopic analysis including IR, MS and NMR data. The cytotoxic activities of these compounds were evaluated. Results showed that 3′-O-methyl isocrenatoside (1) and methyl caffeate (2) exhibited significant cytotoxicity, with IC₅₀ values of 71.89, 36.97 μg/mL and 32.32, 34.58 μg/mL against the B16F10 murine melanoma and Lewis lung carcinoma cell lines, respectively.     

Synthesis and in vitro antitumour activities of lupeol derivatives

Nine lupeol derivatives were synthesised and assayed in vitro for their antitumour activities against three human tumour cells lines, A549, LAC and HepG2. Of lupeol derivaties, six were new compounds, and five compounds against A549 cells, four compounds against HepG2 cells and three compounds against LAC cells were effective in reducing viability, and the most promising compounds 5, 6 and 9 exhibited high activities against lung and liver cancer cells, even higher activities than those of adriamycin.     

Prenylated flavonoids and dihydrophenanthrenes from the leaves of Epimedium brevicornu and their cytotoxicity against HepG2 cells

Phytochemical study on the leaves of Epimedium brevicornu finally led to the isolation of four prenylated flavonoids (1–4) and three dihydrophenanthrenes (5–7), of which 1, 2, 5 and 7 were new compounds. The structures of these compounds were established mainly by spectroscopic techniques, including NMR spectroscopy and mass spectrometry. These isolates exhibited the cytotoxic activities against HepG2 cells with the IC₅₀ values of 32.8–87.3 μM.     

Toonapolyynes A–D,new polyynes from Toona ciliata

Abstract

Phytochemical investigation on the leaves and twigs of Toona ciliata has led to the isolation of four new polyynes (1–4) and two knowns (5 and 6). Their structures were determined by extensive spectroscopic analysis (MS, UV, IR, and NMR) and Mosher’s method. All compounds were evaluated for their inhibitory activities against HepG2 human tumor cell line but were inactive.     

New glycosylsphingolipids from Psychotria serpens L

Abstract

In clinical, Psychotria serpens L. was often substitute for Caulis trachelospermi to treat cancer in China. Meanwhile, EtOAc and n-BuOH fractions of MeOH extract of P. serpens L. show power activity against H460, HepG2, Hela, and PC9/GR cell lines, and no toxic effects against normal 16HBE cell lines. In our ongoing search for bioactive novel compounds from Chinese material medica, one new type of glycosylsphingolipids Psychotramide (1a–1c) were isolated from P. serpens L., and their structures were identified through spectroscopic techniques including NMR (1D and 2D) and MS (LC-MS, and GC-MS).     

A new galloyl glycoside from Lotus corniculatus

A new galloyl glucoside, 2,6-di-O-acetyl 1-O-galloyl β-D-glucose (1), along with five known phenolic compounds were isolated from the whole plants of Lotus corniculatus. Their structures were elucidated by means of extensive spectroscopic analysis. Compound 1 was assessed for its cytotoxicity against five human tumour lines (HL-60, SMMC-7721, A-549, MCF-7 and SW-480), and the result showed that it had no activity.     

Chemical composition of essential oils from the vegetative and reproductive structures of Copaifera langsdorffii Desf.

GC/FID and GC–MS analysis revealed germacrene D, bicyclogermacrene, α-cadinol and cubenol as major compounds from aril. Germacrene D, bicyclogermacrene, trans-caryophyllene and δ-elemene are major compounds in fruits. Germacrene D, spathulenol, trans-caryophyllene and caryophyllene oxide are major compounds in leaves. Furthermore, multivariate analysis revealed distinct groups between the composition of essential oils from aril and fruit, when compared with terpene production found in leaves. Lipid composition found in arils could be protected by the presence of non-oxygenated sesquiterpenes, as germacrene D and bicyclogermacrene. Chemical profiles of essential oils from the fruits, arils and leaves of Copaifera langsdorffii Desf. revealed different compositions, which could be related to environmental pressures. Thereby, non-oxygenated sesquiterpenes can also work against herbivory, pathogens and predator's attack, emphasising the importance of further studies among terpenes, ecology interactions and plant physiology.     

LC-ESI-MS/MS and cytotoxic activity of three Pistacia species

LC-ESI-MS/MS was used for a comprehensive characterisation of ethanol extract from the leaves of three Pistacia species. After optimisation of the method and the use of the negative ionisation mode, a total of 42 different compounds were identified, of which 22 were tentatively characterised in P. chinensis Bunge, 33 in P. khinjuk stocks and 25 in P. lentiscus L. leaves. Flavonoids, phenolic acids, and their derivatives were the most abundant identified compounds. LC-ESI-MS/MS revealed identification of 15, 18 and 6 not previously detected compounds in P. chinensis Bunge, P. khinjuk Stocks and P. lentiscus L., respectively. The three extracts were also tested for their cytotoxic activities against human PC3 prostate cancer, A549 lung cancer, MCF7 breast cancer and HepG2 liver cancer. Generally, all the extracts have a moderate cytotoxic activity against lung, breast and prostate cancer, with different IC₅₀. However, only P. lentiscus L. showed moderate activity against liver cancer.     

Utilization of cyanoacetohydrazide and 2-(1,3-dioxoisoindolin-2-yl) acetyl chloride in the synthesis of some novel anti-proliferative heterocyclic compounds

Abstract

Owing to its high reactivity and commercial availability, 2-cyanoacetohydrazide can be utilized as a versatile and appropriate intermediate for synthesis of a broad variety of heterocyclic compounds. Thus, 2-cyanoacetohydrazide and 2-(1,3-dioxoisoindolin-2-yl) acetyl chloride were used as starting materials for construction of new heterocyclic compounds bearing 1,3-dioxoisoindoline moiety. The newly synthesized compounds were recognized by elemental analyses and spectral data (IR, ¹H-NMR, and ¹³C-NMR spectra). The synthesized compounds were screened for their anti-proliferative activity against two human epithelial cell lines; breast (MCF-7) and liver (HepG2) as well as to normal fibroblasts (WI-38). The data showed distinctly that compounds 1 and 12 presented promising in-vitro anti-proliferative activity against two cell lines (MCF-7 and HepG2) without harming normal fibroblasts.     

Synthesis,characterization and biological evaluation of some novel sulfonylthiosemicarbazides

Abstract

A series of thiosemicarbazides were synthesized and structurally characterized by spectroscopic techniques (NMR, FT-IR) besides elemental analysis. These compounds were evaluated for their cytotoxicity against human breast cancer cell line MCF7 and prostate cancer cell line PC3 and nonmalignant fibroblast L929 cell line by MTT assay. Among the compounds, N-[2-(4-chlorophenyl)ethyl]-2-[(4-methylphenyl)sulfonyl]hydrazinecarbothioamide (3d) and 2-[(4-methylphenyl)sulfonyl]-N-[4-(trifluoromethoxy)phenyl]hydrazinecarbothioamide (3f) were found to display significant cytotoxicity with IC₅₀ of 13.87?μM (against PC3 cell line) and 1.47?μM (against MCF7 cell line), respectively. These compounds were non-cytotoxic to normal cell line with IC₅₀>100?μM. Western blotting studies demonstrated that compound 3f induced apoptosis and caused cell death in the MCF7 and PC3 cell lines via an increase in Bax protein expression and a slight decrease in Bcl-2 protein expression. The gene expression ratio Bax/Bcl-2 showed the induction of mitochondrial apoptosis in cancer cell lines. All of synthesized compounds have also been tested for antioxidant activity and all compounds achieved strong inhibition of the DPPH radical. These findings showed that compound 3f, displays potential to be further explored in the development of new anticancer agents.     

Pharmacophore Modeling and Virtual Screening of Novel Inhibitors for c-Kit Kinase

The stem cell factor receptor (c‐Kit) has been known to play critical roles in regulating numerous aspects of cellular behavior including cell growth, differentiation, migration and metabolism. In this investigation, a three‐dimensional pharmacophore model of c‐Kit inhibitors has been established by using the HypoGen algorithms implemented in the catalyst software package. The best quantitative pharmacophore model, hypothesis 1, which has the highest correlation coefficient (0.989), consists of one hydrogen bond acceptor, two hydrogen bond donors and one hydrophobic feature. To our knowledge, this is the first report on the pharmacophore modeling study of c‐Kit inhibitors. The best hypothesis, hypothesis 1, was used to screen molecular structural databases, including Specs and China Natural Products Database for potential lead compounds. The hit compounds were subsequently subjected to filtering by Lipinski's rules and docking study to refine the retrieved hits and as a result to reduce the rate of false positive. Finally 28 compounds were purchased or synthesized for further in vitro assay against several human tumour cell lines including A549, MCF‐7, HepG2 and PC‐3, in which c‐Kit is overexpressed. Two compounds show very low micromolar inhibition potency against the PC‐3 and HepG2 cell lines respectively. And they were selected for further modification and testing.     

Using natural deep eutectic solvents for the extraction of metabolites in Byrsonima intermedia leaves

Natural deep eutectic solvents have been used as an alternative to organic solvents for the extraction of plants metabolites, allowing for the extraction of compounds of different polarities, while being inexpensive, non‐toxic, and easy to prepare. This work presents the comparison of the chromatographic profiles by high‐performance liquid chromatography with diode‐array detection obtained from Byrsonima intermedia (Malpighiaceae) using five choline chloride‐based natural deep eutectic solvents, in addition to the most used traditional extraction solvents, methanol/water 7:3 and ethanol/water 7:3 v/v. A reference extract was used to tentatively identify compounds by high‐performance liquid chromatography with tandem mass spectrometry. The water content appeared to be important for the extraction efficiency and the mixture choline chloride/glycerol was shown to be the best candidate for efficiently extracting this matrix when compared with the traditional extraction media in addition to being far greener as shown by the environmental analysis tool. Seven phenolic compounds (digalloyl quinic acid, proanthocyanidin dimer, galloylproanthocyanidin dimer, quercetin‐O‐hexoside, galloyl quercetin hexoside, quercetin‐O‐pentoside, and galloyl quercetin pentoside) were tentatively identified in all extracts. Moreover, the influence of these solvents on the antioxidant activity of the extracts was studied and the results for choline chloride/glycerol extracts were very similar to that of the traditional extraction solvents.     

Liquid chromatography/electrospray ionization tandem mass spectrometry profiling of compounds from the infusion of Byrsonima fagifolia Niedenzu

A rapid analytical approach suitable to achieve a comprehensive characterization of the compounds present in the infusion prepared from the leaves of Byrsonima fagifolia Niedenzu (Malpighiaceae), a Brazilian plant used as an infusion to treat gastric disorders, was developed. The method was based on high-performance liquid chromatography coupled to electrospray negative ionisation multistage ion trap mass spectrometry (HPLC/ESI-ITMSn).The main ions in the ESI-ITMS spectra were attributed to a quinic acid core containing from one to five galloyl units. Quercetin derivatives containing one and two sugar moieties as well as galloyl esterification were also detected. These results indicated that HPLC/ESI-ITMSn is easily applicable to infusions of this plant and allows the rapid and direct identification of these compounds in crude plant extracts.     

Three New Benzophenone Glucosides from the Leaves of Planchonella obovata

Chemical investigation of the EtOH extract of the leaves of Planchonella obovata resulted in the isolation of four benzophenone glucosides, 1 – 4 , of which three, 2 – 4 , are new chemical entities together with five known flavonol glycosides. Their structures were elucidated by spectroscopic analysis. Among the isolated compounds, iriflophenone 2‐O‐(2,6‐di‐O‐galloyl)‐β‐D ‐glucopyranoside ( 4 ) showed some activity (91.4 and 15.0% inhibition at 100 and 10 μg/ml, resp.) against the α‐glucosidase of Bacillus stearothermophilus.     

Synthesis of a Regioisomer of β‐Lapachone and Analogs as Potent Antitumor Agents

A regioisomer of β‐lapachone and two analogs were synthesized and evaluated for their antitumor activities. All three compounds tested were found to exhibit promising activities against PC‐3, HepG2, and Raji cancer cell lines in μM range.     

A new triterpenoid saponin and a diterpene glucoside from the seeds of Orychophragmus violaceus

One new triterpenoid saponin orychoside A (1) and one new diterpene glucoside orychoside B (12), together with eleven known compounds, were isolated from the seeds of Orychophragmus violaceus. The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The known compounds were identified by comparison with data reported in the literature. All compounds were tested for their cytotoxic activities against the HepG2 and A549 cell lines in vitro. The new compound 1 exhibited potent cytotoxicity against the two cell lines with IC₅₀ values of 7.13 and 8.77 μM, respectively. Compounds 2, 5, 8 and 9 were found to possess obvious cytotoxicity.     

Synergies of urushiol and its pechmann derivative compatible with paclitaxel anti-HepG2 activity

The paper investigated the synergistic inhibitory effects of 1 (triene urushiol), 2 (monoene urushiol), 3 (urushiol pechmann derivative) and paclitaxel on proliferation of human hepatocellular carcinoma cell line HepG2. The inhibitory rate of cell proliferation was detected by MTT assay after HepG2 cells were separately treated with compounds 1, 2 and 3 combined with paclitaxel at different concentrations for 72 h. The joint index analysis was used to examine whether those compatible drugs had synergistic effect. The results showed that compounds 1, 2 and 3 had significant inhibitory effect on the proliferation of HepG2 cells in a dose-dependent manner, and their half inhibitory concentrations IC₅₀ were 29.3, 55.5 and 27.1 μM respectively. The synergistic effect of compounds 1, 2 and 3 combined with paclitaxel significantly inhibited the proliferation of HepG2 cells in vitro.     

N'-(1-([1,1'-biphenyl]-4-yl)ethylidene)-2-cyanoacetohydrazide as scaffold for the synthesis of diverse heterocyclic compounds as prospective antitumor and antimicrobial activities

In this article, the main target was to study the antitumor and antimicrobial efficacy of new heterocycles conjugated with biphenyl moiety in-vitro. This was implemented by utilizing N'-(1-([1,1'-biphenyl]-4-yl)ethylidene)-2-cyanoacetohydrazide 3 as a material for the synthesis of various heterocyclic compounds. Among of them, some compounds were selected and assayed against two antitumor cell lines as (HepG2) and (HCT-116). Conspicuously, the achieved results showed that compounds 6, 13, and 23 possess significant potency against both cancer cell lines. Particularly, compound 13 exhibited a remarkable efficacy, similar to the standard anticancer drug (doxorubicin), against both cancer cell lines. Noteworthy, compound 13 may serve as a potential anticancer therapeutic drug in the future. On the other hand, In-vitro antifungal and antibacterial activities of selected compounds were assayed and the results indicated that the compound 6 exhibited significant potency against Candida albicans, while compounds 6 and 8 displayed spectacular results for the antibacterial study.     

A new abietane diterpenoid glycoside from ajuga ovalifolia var. calantha

A new abietane diterpenoid glycoside, ajugaside B (1), along with three known compounds (2–4), were isolated from the whole plants of Ajuga ovalifolia var. calantha. The structure of the new compound (1) was elucidated by means of spectroscopic analyses (HRESIMS, IR, NMR and ECD). All of the isolated compounds were evaluated for their antitumor activities against MGC803, MCF-7, A549, HT29 and HepG2 cell lines. Compounds 3–4 showed moderate cytotoxicity against all tested cell lines with IC₅₀ values of 1.8–7.3?μM.