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LC-QTOF-MS/MS Based Molecular Networking Approach for the Isolation of α-Glucosidase Inhibitors and Virucidal Agents from Coccinia grandis (L.) Voigt.

ABSTRACT: Coccinia grandis or ivy gourd is an edible plant. Its leaves and fruits are used as vegetable in many countries. Many works on antidiabetic activity of a crude extract of C. grandis, i.e., in vitro, in vivo, and clinical trials studies, have been reported. Profiles of the antidiabetic compounds were previously proposed by using LC-MS or GC-MS. However, the compounds responsible for antidiabetic activity have rarely been isolated and characterized by analysis of 1D and 2D NMR data. In the present work, UHPLC-ESI-QTOF-MS/MS analysis and GNPS molecular networking were used to guide the isolation of α-glucosidase inhibitors from an extract of C. grandis leaves. Seven flavonoid glycosides including rutin (1), kaempferol 3-O-rutinoside (2) or nicotiflorin, kaempferol 3-O-robinobioside (3), quercetin 3-O-robinobioside (4), quercetin 3-O-β-D-apiofuranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (5) or CTN-986, kaempferol 3-O-β-D-api-furanosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside (6), and kaempferol 3-O-β-D-apiofuranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)]-β-D-galactopyranoside (7) were isolated from C. grandis leaves. This is the first report of glycosides containing apiose sugar in the genus Coccinia. These glycosides exhibited remarkable α-glucosidase inhibitory activity, being 4.4-10.3 times more potent than acarbose. Moreover, they also displayed virucidal activity against influenza A virus H1N1, as revealed by the ASTM E1053-20 method.

SUBMITTER: Astiti MA

PROVIDER: S-EPMC8701318 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Ivy gourd (Coccinia grandis L. Voigt) root suppresses adipocyte differentiation in 3T3-L1 cells.

Project description:BACKGROUND: Ivy gourd (Coccinia grandis L. Voigt) is a tropical plant widely distributed throughout Asia, Africa, and the Pacific Islands. The anti-obesity property of this plant has been claimed but still remains to be scientifically proven. We therefore investigated the effects of ivy gourd leaf, stem, and root on adipocyte differentiation by employing cell culture model. METHODS: Dried roots, stems, and leaves of ivy gourd were separately extracted with ethanol. Each extract was then applied to 3T3-L1 pre-adipocytes upon induction with a mixture of insulin, 3-isobutyl-1-methylxanthine, and dexamethasone, for anti-adipogenesis assay. The active extract was further fractionated by a sequential solvent partitioning method, and the resulting fractions were examined for their abilities to inhibit adipogenesis in 3T3-L1 cells. Differences in the expression of adipogenesis-related genes between the treated and untreated cells were determined from their mRNA and protein levels. RESULTS: Of the three ivy gourd extracts, the root extract exhibited an anti-adipogenic effect. It significantly reduced intracellular fat accumulation during the early stages of adipocyte differentiation. Together with the suppression of differentiation, expression of the genes encoding PPAR?, C/EBP?, adiponectin, and GLUT4 were down-regulated. Hexane-soluble fraction of the root extract also inhibited adipocyte differentiation and decreased the mRNA levels of various adipogenic genes in the differentiating cells. CONCLUSIONS: This is the first study to demonstrate that ivy gourd root may prevent obesity based mainly on the ability of its active constituent(s) to suppress adipocyte differentiation in vitro. Such an inhibitory effect is mediated by at least down-regulating the expression of PPAR?-the key transcription factor of adipogenesis in pre-adipocytes during their early differentiation processes.

| S-EPMC4064515 | biostudies-literature

UHPLC-ESI-QTOF-MS/MS-Based Molecular Networking Guided Isolation and Dereplication of Antibacterial and Antifungal Constituents of Ventilago denticulata.

Project description:Ventilago denticulata is an herbal medicine for the treatment of wound infection; therefore this plant may rich in antibacterial agents. UHPLC-ESI-QTOF-MS/MS-Based molecular networking guided isolation and dereplication led to the identification of antibacterial and antifungal agents in V. denticulata. Nine antimicrobial agents in V. denticulata were isolated and characterized; they are divided into four groups including (I) flavonoid glycosides, rhamnazin 3-rhamninoside (7), catharticin or rhamnocitrin 3-rhamninoside (8), xanthorhamnin B or rhamnetin 3-rhamninoside (9), kaempferol 3-rhamninoside (10) and flavovilloside or quercetin 3-rhamninoside (11), (II) benzisochromanquinone, ventilatones B (12) and A (15), (III) a naphthopyrone ventilatone C (16) and (IV) a triterpene lupeol (13). Among the isolated compounds, ventilatone C (16) was a new compound. Moreover, kaempferol, chrysoeriol, isopimpinellin, rhamnetin, luteolin, emodin, rhamnocitrin, ventilagodenin A, rhamnazin and mukurozidiol, were tentatively identified as antimicrobial compounds in extracts of V. denticulata by a dereplication method. MS fragmentation of rhamnose-containing compounds gave an oxonium ion, C6H9O3+ at m/z 129, while that of galactose-containing glycosides provided the fragment ion at m/z 163 of C6H11O5+. These fragment ions may be used to confirm the presence of rhamnose or galactose in mass spectrometry-based analysis of natural glycosides or oligosaccharide attached to biomolecules, that is, glycoproteins.

| S-EPMC7558283 | biostudies-literature

Fecal metabolite analysis of Japanese macaques in Yakushima by LC-MS/MS and LC-QTOF-MS.

Project description:We performed a comprehensive fecal metabolite analysis using LC-MS/MS and LC-QTOF-MS approaches as a preliminary study. Feces of Japanese macaques on Yakushima Island were collected from five monkeys at two separate locations. Using the former methodology, 59 substances such as free amino acids, nucleotides, nucleosides and nucleic acid bases, and organic acids in the citrate cycle were quantitatively detected and successfully differentiated in two different monkey groups by the concentrations of nucleic acid metabolites and free amino acids. In the latter, around 12,000 substances were detected both by positive and negative mode in each sample. Differences in signal intensities were observed between two monkey groups in the concentrations of plant secondary metabolites such as cyanogenic glycosides, flavonoids, and phenolics.

| S-EPMC8267200 | biostudies-literature

Optimization of beef broth processing technology and isolation and identification of flavor peptides by consecutive chromatography and LC-QTOF-MS/MS.

Project description:To investigate the flavor peptides of beef broth obtained under optimized stewing conditions, separation procedures such as ultrafiltration, Sephadex G-15 column chromatography, and reversed-phase high-performance liquid chromatography were employed to isolate the umami taste peptides. Sensory evaluation was combined with liquid chromatography-mass spectrometry to detect the flavor peptides. The optimization of the stewing process conditions was studied using the orthogonal method, which indicated that time had the most significant effect on the taste efficiency of sensory evaluation, followed by the mixed spices, sucrose, and salt. The optimized cooking conditions included 3.5 hr of cooking time, 1.800 g of sucrose, 2.125 g of salt, and 1.500 g of mixed spices. The results showed that six peptides, including SDEEVEH, AEVPEVH, GVDNPGHP, GSDGSVGPVGP, SDGSVGPVGP, and DEAGPSIVH, were detected in sample X1M1; and seven peptides, including VAPEEHPT, VVSNPVDIL, VGGNVDYK, PFGNTHN, EAGPSIVHR, VDFDDIQK, and DEAGPSIVH, were detected in sample X2M2. This study compared the flavor peptides in stewed beef before and after the optimization, and thus provided a basis for the improvement of beef processing technology.

| S-EPMC7455977 | biostudies-literature

Coccinia grandis

Project description:Coccinia grandis de novo transcriptome to understand sex expression and modification

| PRJNA393268 | ENA

Coccinia grandis

Project description:Coccinia grandis Transcriptome or Gene expression

| PRJNA321965 | ENA

Coccinia grandis

Project description:Coccinia grandis overview

| PRJNA353533 | ENA

Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog, asperpyrroindotide A, using LC-MS/MS-based molecular networking.

Project description:Further insights on the secondary metabolites of a soft coral-derived fungus Aspergillus versicolor under the guidance of MS/MS-based molecular networking led to the isolation of seven known cycloheptapeptides, namely, asperversiamides A-C (1-3) and asperheptatides A-D (4-7) and an unusual pyrroloindoline-containing new cycloheptapeptide, asperpyrroindotide A (8). The structure of 8 was elucidated by comprehensive spectroscopic data analysis, and its absolute configuration was determined by advanced Marfey's method. The semisynthetic transformation of 1 into 8 was successfully achieved and the reaction conditions were optimized. Additionally, a series of new derivatives (10-19) of asperversiamide A (1) was semi-synthesized and their anti-tubercular activities were evaluated against Mycobacterium tuberculosis H37Ra. The preliminary structure-activity relationships revealed that the serine hydroxy groups and the tryptophan residue are important to the activity.Supplementary informationThe online version contains supplementary material available at 10.1007/s42995-022-00157-8.

| S-EPMC9854410 | biostudies-literature

Ginsenosides analysis of New Zealand-grown forest Panax ginseng by LC-QTOF-MS/MS.

Project description:Background:Ginsenosides are the unique and bioactive components in ginseng. Ginsenosides are affected by the growing environment and conditions. In New Zealand (NZ), Panax ginseng Meyer (P. ginseng) is grown as a secondary crop under a pine tree canopy with an open-field forest environment. There is no thorough analysis reported about NZ-grown ginseng. Methods:Ginsenosides from NZ-grown P. ginseng in different parts (main root, fine root, rhizome, stem, and leaf) with different ages (6, 12, 13, and 14 years) were extracted by ultrasonic extraction and characterized by Liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. Twenty-one ginsenosides in these samples were accurately quantified and relatively quantified with 13 ginsenoside standards. Results:All compounds were separated in 40 min, and a total of 102 ginsenosides were identified by matching MS spectra data with 23 standard references or published known ginsenosides from P. ginseng. The quantitative results showed that the total content of ginsenosides in various parts of P. ginseng varied, which was not obviously dependent on age. In the underground parts, the 13-year-old ginseng root contained more abundant ginsenosides among tested ginseng samples, whereas in the aboveground parts, the greatest amount of ginsenosides was from the 14-year-old sample. In addition, the amount of ginsenosides is higher in the leaf and fine root and much lower in the stem than in the other parts of P. ginseng. Conclusion:This study provides the first-ever comprehensive report on NZ-grown wild simulated P. ginseng.

| S-EPMC7322743 | biostudies-literature

LC-QTOF-MS Identification of Major Urinary Cyclopropylfentanyl Metabolites Using Synthesized Standards.

Project description:Cyclopropylfentanyl is a fentanyl analog implicated in 78 deaths in Europe and over 100 deaths in the United States, but toxicological information including metabolism data about this drug is scarce. The aim of this study was to provide the exact structure of abundant and unique metabolites of cyclopropylfentanyl along with synthesis routes. In this study, metabolites were identified in 13 post-mortem urine samples using liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF-MS). Samples were analyzed with and without enzymatic hydrolysis, and seven potential metabolites were synthesized in-house to provide the identity of major metabolites. Cyclopropylfentanyl was detected in all samples, and the most abundant metabolite was norcyclopropylfentanyl (M1) that was detected in 12 out of 13 samples. Reference materials were synthesized (synthesis routes provided) to identify the exact structure of the major metabolites 4-hydroxyphenethyl cyclopropylfentanyl (M8), 3,4-dihydroxyphenethyl cyclopropylfentanyl (M5) and 4-hydroxy-3-methoxyphenethyl cyclopropylfentanyl (M9). These metabolites are suitable urinary markers of cyclopropylfentanyl intake as they are unique and detected in a majority of hydrolyzed urine samples. Minor metabolites included two quinone metabolites (M6 and M7), not previously reported for fentanyl analogs. Interestingly, with the exception of norcyclopropylfentanyl (M1), the metabolites appeared to be between 40% and 90% conjugated in urine. In total, 11 metabolites of cyclopropylfentanyl were identified, including most metabolites previously reported after hepatocyte incubation.

| S-EPMC6936316 | biostudies-literature

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