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Combination of Molecular Networking and LC-MS/MS Profiling in Investigating the Interrelationships between the Antioxidant and Antimicrobial Properties of Curculigo latifolia.

ABSTRACT: Curculigo is a potent plant with a variety of traditional uses, such as anti-oxidant, anti-diabetic, anti-tumor, anti-bacterial, anti-cancer, anti-osteoporosis, and wound-healing. The comprehensive profiling of the Curculigolatifolia metabolome was carried out by generating a molecular network (MN) from Liquid Chromatography-Tandem Mass Spectrometry (LC-MS/MS) data to profile the methanol extract and correlating them with their antioxidant (2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH), total phenolic contents (TPC), and β-carotene) and antimicrobial (disk-diffusion agar method, minimum inhibitory concentration (MIC), and minimum bactericidal concentration (MBC)) properties. The antioxidant capacity was observed to be significantly higher in the rhizome crude extract, with 18.10 ± 0.91 µg/mL DPPH activity, and a β-carotene bleaching result of 35.20%. For the antimicrobial activity, the leaf crude extract exhibited a strong Staphylococcus aureus and Salmonella choleraesuis (8-15 ± 3.0 mm) inhibition in the disk-diffusion agar. The leaf extract also exhibited maximum antibacterial activity against S. aureus (MIC = ±0.25 mg/mL, MBC = ±0.25 mg/mL) and S. choleraesuis (MIC = ±0.25 mg/mL, MBC = ±0.25 mg/mL). LC-MS/MS analysis and MN revealed norlignans and phenolic glycosides as major metabolites in the rhizome and leaf extracts of the negative mode (M - H)^-. Fourteen known compounds were identified, and three unknown compounds were putatively identified in the rhizome extract, while ten known compounds and six unknown compounds were putatively identified in the leaf extract.

SUBMITTER: Mad Nasir N

PROVIDER: S-EPMC8401502 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Background Curculigo latifolia is a perennial plant endogenous to Southeast Asia whose fruits contain the taste-modifying protein neoculin, which binds to sweet receptors and makes sour fruits taste sweet. Although similar to snowdrop (Galanthus nivalis) agglutinin (GNA), which contains mannose-binding sites in its sequence and 3D structure, neoculin lacks such sites and has no lectin activity. Whether the fruits of C. latifolia and other Curculigo plants contain neoculin and/or GNA family members was unclear. Results Through de novo RNA-seq assembly of the fruits of C. latifolia and the related C. capitulata and detailed analysis of the expression patterns of neoculin and neoculin-like genes in both species, we assembled 85,697 transcripts from C. latifolia and 76,775 from C. capitulata using Trinity and annotated them using public databases. We identified 70,371 unigenes in C. latifolia and 63,704 in C. capitulata. In total, 38.6% of unigenes from C. latifolia and 42.6% from C. capitulata shared high similarity between the two species. We identified ten neoculin-related transcripts in C. latifolia and 15 in C. capitulata, encoding both the basic and acidic subunits of neoculin in both plants. We aligned these 25 transcripts and generated a phylogenetic tree. Many orthologs in the two species shared high similarity, despite the low number of common genes, suggesting that these genes likely existed before the two species diverged. The relative expression levels of these genes differed considerably between the two species: the transcripts per million (TPM) values of neoculin genes were 60 times higher in C. latifolia than in C. capitulata, whereas those of GNA family members were 15,000 times lower in C. latifolia than in C. capitulata. Conclusions The genetic diversity of neoculin-related genes strongly suggests that neoculin genes underwent duplication during evolution. The marked differences in their expression profiles between C. latifolia and C. capitulata may be due to mutations in regions involved in transcriptional regulation. Comprehensive analysis of the genes expressed in the fruits of these two Curculigo species helped elucidate the origin of neoculin at the molecular level.

Project description:The fruit of Tetradium ruticarpum (TR) is commonly used in Chinese herbal medicine and it has known antiproliferative and antitumor activities, which can serve as a good source of functional ingredients. Although some antiproliferative compounds are reported to be present in TR fruit, most studies only focused on a limited range of metabolites. Therefore, in this study, the antiproliferative activity of different extracts of TR fruit was examined, and the potentially antiproliferative compounds were highlighted by applying an untargeted liquid chromatography-tandem mass spectrometry (LC-MS/MS)-based multi-informative molecular networking strategy. The results showed that among different extracts of TR fruit, the EtOAc fraction F2-3 possessed the most potent antiproliferative activity against HL-60, T24, and LX-2 human cell lines. Through computational tool-aided structure prediction and integrating various data (sample taxonomy, antiproliferative activity, and compound identity) into a molecular network, a total of 11 indole alkaloids and 47 types of quinolone alkaloids were successfully annotated and visualized into three targeted bioactive molecular families. Within these families, up to 25 types of quinolone alkaloids were found that were previously unreported in TR fruit. Four indole alkaloids and five types of quinolone alkaloids were targeted as potentially antiproliferative compounds in the EtOAc fraction F2-3, and three (evodiamine, dehydroevodiamine, and schinifoline) of these targeted alkaloids can serve as marker compounds of F2-3. Evodiamine was verified to be one of the major antiproliferative compounds, and its structural analogues discovered in the molecular network were found to be promising antitumor agents. These results exemplify the application of an LC-MS/MS-based multi-informative molecular networking strategy in the discovery and annotation of bioactive compounds from complex mixtures of potential functional food ingredients.

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Combination of Molecular Networking and LC-MS/MS Profiling in Investigating the Interrelationships between the Antioxidant and Antimicrobial Properties of Curculigo latifolia.

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