Stem Extract from Momordica cochinchinensis Induces Apoptosis in Chemoresistant Human Prostate Cancer Cells (PC-3)

Natural compounds have been recognized as valuable sources for anticancer drug development. In this work, different parts from Momordica cochinchinensis Spreng were selected to perform cytotoxic screening against human prostate cancer (PC-3) cells. Chromatographic separation and purification were performed for the main constituents of the most effective extract. The content of the fatty acids was determined by Gas Chromatography-Flame Ionization Detector (GC–FID). Chemical structural elucidation was performed by spectroscopic means. For the mechanism of the apoptotic induction of the most effective extract, the characteristics were evaluated by Hoechst 33342 staining, sub-G1 peak analysis, JC-1 staining, and Western blotting. As a result, extracts from different parts of M. cochinchinensis significantly inhibited cancer cell viability. The most effective stem extract induced apoptosis in PC-3 cells by causing nuclear fragmentation, increasing the sub-G1 peak, and changing the mitochondrial membrane potential. Additionally, the stem extract increased the pro-apoptotic (caspase-3 and Noxa) mediators while decreasing the anti-apoptotic (Bcl-xL and Mcl-1) mediators. The main constituents of the stem extract are α-spinasterol and ligballinol, as well as some fatty acids. Our results demonstrated that the stem extract of M. cochinchinensis has cytotoxic and apoptotic effects in PC-3 cells. These results provide basic knowledge for developing antiproliferative agents for prostate cancer in the future.     

Cucurbitane‐Type Triterpenoids from Momordica charantia

The six new cucurbitane‐type triterpenoids 1 – 6 , along with the ten known triterpenoids 7 – 16 , were isolated from the vines and leaves of Momordica charantia. The structures of the new compounds were elucidated as (3β,7β,15β,23E)‐3,7,15,25‐tetrahydroxycucurbita‐5,23‐dien‐19‐al ( 1 ), (3β,7β)‐3,7,22,23‐tetrahydroxycucurbita‐5,24‐dien‐19‐al ( 2 ), (3β,7β)‐3,7,23,24‐tetrahydroxycucurbita‐5,25‐dien‐19‐al ( 3 ), (3β,7β,23S)‐3,7,23‐trihydroxycucurbita‐5,24‐dien‐19‐al 7‐β‐D ‐glucopyranoside ( 4 ), (3β,7β,23E)‐cucurbita‐5,23‐diene‐3,7,19,25‐tetrol 7‐β‐D ‐glucopyranoside ( 5 ), and (3β,7β,23E)‐3,7‐dihydroxy‐25‐methoxy‐cucurbita‐5,23‐dien‐19‐al 3‐β‐D ‐allopyranoside ( 6 ), by extensive analyses of their spectral data, as well as by chemical methods.     

Optimization of Maceration Conditions for Improving the Extraction of Phenolic Compounds and Antioxidant Effects of Momordica Charantia L. Leaves Through Response Surface Methodology (RSM) and Artificial Neural Networks (ANNs)

The main goals of this research were the chemical and biological characterization of the bitter melon (Momordica charantia) isolate obtained by traditional (maceration) extraction, as well as optimization of this process using response surface methodology (RSM) and artificial neural networks (ANNs). Experiments were performed using Box–Behnken experimental design on three levels and three variables: extraction temperature (20?°C, 40?°C, and 60?°C), solvent concentration (30%, 50%, and 70%) and extraction time (30, 60, and 90?min). The measurements consisted of 15 randomized runs with 3 replicates in a central point. The antioxidant activity of obtained extracts was determined by the 1,1-diphenyl-2-picrylhydrazyl (DPPH), cupric ion reducing antioxidant capacity (CUPRAC) and ferric reducing antioxidant power (FRAP) assays while chemical characterization was done in terms of the total phenolic content (TPC). The methodology shows positive influence of solvent concentration on all four observed outputs, while temperature showed a negative impact. RSM showed that the optimal extraction conditions were 20?°C, 70% methanol, and an extraction time of 52.2?min. Under these conditions, the TPCs were 20.66 milligrams of gallic acid equivalents (mg GAE/g extract), DPPH 30.22 milligrams of trolox equivalents (mg TE/g extract), CUPRAC 67.78 milligrams of trolox equivalents (mg TE/g extract), and FRAP 45.48 milligrams of trolox equivalents (mg TE/g extract). The neural network coupled with genetic algorithms (ANN-GA) was also used to optimize the conditions for each of the outputs separately. It is anticipated that results reported herein will establish baseline data and also demonstrate that that the present model can be applied in the food and pharmaceutical industries.     

Cucurbitane Triterpenoids from the Fruit Pulp of Momordica charantia and Their Cytotoxic Activity

Two new cucurbitane‐type triterpenes, 25‐methoxycucurbita‐5,23(E)‐diene‐3β,19‐diol ( 1 ) and 7β‐ethoxy‐3β‐hydroxy‐25‐methoxycucurbita‐5,23(E)‐dien‐19‐al ( 2 ), together with three known cucurbitane‐type triterpenes, 3β,7β,25‐trihydroxycucurbita‐5,23(E)‐dien‐19‐al ( 3 ), (23E)‐3β‐hydroxy‐7β,25‐dimethoxycucurbita‐5,23‐dien‐19‐al ( 4 ), and 3β‐hydroxy‐25‐methoxycucurbita‐6,23(E)‐dien‐19,5β‐olide ( 5 ), were isolated from the fruit pulp of Momordica charantia. The structures of two new compounds were elucidated on the basis of 1D and 2D NMR, MS, IR, optical rotation. Among these isolates, compounds 1 , 2 , and 5 showed slight cytotoxic activity against the SK‐Hep 1 cell line with IC₅₀ values of 33.1, 24.3, and 38.7 μM, respectively.     

Study of pancreatic lipase inhibition kinetics and LC–QTOF–MS‐based identification of bioactive constituents of Momordica charantia fruits

The different parts of Momordica charantia have been reported to have several therapeutic applications against hyperglycemia and hypercholesterolemia associated with pancreatic lipase (PL). Inhibition of this enzyme prevents the absorption of dietary triglyceride in the intestine, and thus exerts an anti‐obesity effect. This study aimed to investigate the bioactive constituents of the fruits of M. charantia (MCF) extract and fractions against pancreatic PL followed by study of their inhibition kinetics. The PL inhibitory assay was performed spectrophotometrically by measuring the change in absorbance of the products at 405 nm, using p‐nitrophenylcaprylate as substrate. The results indicated that the ethyl acetate fraction of MCF (EFMC) offered significant, dose‐dependent inhibition against PL, compared with the positive control, Orlistat. The enzyme kinetics study revealed the inhibition to be a mixed type in nature. Additionally, the total phenol and flavonoid content of the fractions was estimated. A positive correlation between phenolic content of EFMC and its PL inhibitory activity was established statistically, which implied that higher inhibition potential was contributed by the phenolic compounds. The identification of the bioactive constituents was further confirmed by LC–QTOF–MS study. This finding suggested that phenolic compounds of MCF can serve as functional food components to address obesity‐related disorders linked with PL.     

气相色谱-质谱法测定苦瓜超临界CO_2流体萃取产物的挥发性成分

采用超临界CO2萃取法(SFE)从苦瓜中提取有效成分,萃取条件为:萃取釜压力25 MPa,温度42℃,萃取时间3 h,夹带剂无水乙醇用量20 mL。采用气相色谱-质谱法对其挥发性成分进行鉴定,用归一化法测定各组分的含量。色谱条件:HP-5MS石英毛细管柱(0.25 mm*30 m*0.25μm),柱温60℃,恒温1 m     

Comparison of antioxidant capacities and antioxidant components of commercial bitter melon (Momordica charantia L.) products

In this study, the total phenolic contents and total antioxidant capacities of some commercial bitter melon products (powder, packaged powder, capsule, paste in olive oil), and of unripe and ripe fruits were determined by spectrophotometric and chromatographic methods. The total antioxidant capacities of unripe and ripe bitter melon samples, determined by using the CUPRAC (cupric reducing antioxidant capacity assay) and ABTS (2,2′-azino-bis(3-ethylbenzthiazolin-6-sulfonic acid))/HRP (horseradish peroxidase) methods, were 42.5 and 36.3 µmol TRE (Trolox equivalent) g–1, and 8.7 and 7.0 µmol TRE g–1, respectively. The TAC (total antioxidant capacity) order of the studied samples using the same 2 methods were determined as follows: capsule (CUPRAC value, 140.8; ABTS/HRP value, 143.6 µmol TRE g–1) > packaged powder (129.6; 126.1) > powder (52.3; 64.3) > unripe fruit (42.5; 36.3) > paste in olive oil (17.6; 14.4) > ripe fruit (8.7; 7.0). The order of phenolic content was found as follows: unripe fruit (193.2 µmol GAE (gallic acid equivalent) g-1) > capsule (162.0) > packaged powder (160.6) > powder (83.6) > paste in olive oil (38.3) > ripe fruit (14.6).     

比色法测定苦瓜总皂苷

用香草醛-高氯酸比色法测定苦瓜总皂苷。通过对比色条件进行优化得最佳条件：加热时间15min，加热温度60℃，显色剂用量0．7mL8％香草醛-冰乙酸。结果表明，该测定方法精密度高，在50min内显色稳定，加样回收率高，平均加样回收率为101．46％，RSD为1．19％n=3），且操作简单，对设备要求不高，是一种快速测定苦瓜总皂苷的好方法。     

An RP-LC-UV-TWIMS-HRMS and Chemometric Approach to Differentiate between Momordica balsamina Chemotypes from Three Different Geographical Locations in Limpopo Province of South Africa

Momordica balsamina leaf extracts originating from three different geographical locations were analyzed using reversed-phase liquid chromatography (RP-LC) coupled to travelling wave ion mobility (TWIMS) and high-resolution mass spectrometry (HRMS) in conjunction with chemometric analysis to differentiate between potential chemotypes. Furthermore, the cytotoxicity of the three individual chemotypes was evaluated using HT-29 colon cancer cells. A total of 11 molecular species including three flavonol glycosides, five cucurbitane-type triterpenoid aglycones and three glycosidic cucurbitane-type triterpenoids were identified. The cucurbitane-type triterpenoid aglycones were detected in the positive ionization mode following dehydration [M + H − H₂O]⁺ of the parent compound, whereas the cucurbitane-type triterpenoid glycosides were primarily identified following adduct formation with ammonia [M + NH₄]⁺. The principle component analysis (PCA) loadings plot and a variable influence on projection (VIP) analysis revealed that the isomeric pair balsaminol E and/or karavilagen E was the key molecular species contributing to the distinction between geographical samples. Ultimately, based on statistical analysis, it is hypothesized that balsaminol E and/or karavilagen E are likely responsible for the cytotoxic effects in HT-29 cells.     

Triterpenoids from the Stems of Momordica charantia

Two new cucurbitane triterpenes, (23E)‐7β‐methoxycucurbita‐5,23,25‐trien‐3β‐ol ( 1 ) and 23,25‐dihydroxy‐5β,19‐epoxycucurbit‐6‐ene‐3,24‐dione ( 2 ), and a new D : C‐friedooleanane triterpene, 3α‐[(E)‐feruloyloxy]‐D : C‐friedooleana‐7,9(11)‐dien‐29‐oic acid ( 3 ), together with two known D : C‐friedooleanane triterpenes, 3β‐[(E)‐feruloyloxy]‐D : C‐friedooleana‐7,9(11)‐dien‐29‐oic acid ( 4 ) and 3‐oxo‐D : C‐friedooleana‐7,9(11)‐dien‐29‐oic acid ( 5 ), were isolated from the stems of Momordica charantia. The structures of the new compounds 1 – 3 were determined by spectroscopic methods.