Convallaria majalis
Ontology highlight
ABSTRACT:
PROVIDER: PRJNA846452 | ENA |
REPOSITORIES: ENA
Dataset's files
| Action | DRS | |||
|---|---|---|---|---|
| SRR16268145_1.fastq.gz | Fastqsanger.gz | |||
| SRR16268145_2.fastq.gz | Fastqsanger.gz |
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Project description:Phytochemical examination of Convallaria majalis (Liliaceae) whole plants yielded 15 steroidal glycosides (1-15), including nine new compounds (4-6, 10-15) with a lycotetrose unit. The structures of the new compounds were determined using two-dimensional Nuclear magnetic resonance (NMR) analyses and chemical methods. The isolated compounds were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and HSC-4 and HSC-2 human oral squamous cell carcinoma cell lines. Of these, (25S)-spirost-5-en-3?-yl O-?-d-glucopyranosyl-(1?2)-O-[?-d-xylopyranosyl-(1?3)]-O-?-d-glucopyranosyl-(1?4)-?-d-galactopyranoside (1) exhibited cytotoxic activity against HL-60, A549, HSC-4, and HSC-2 cells with IC50 values ranging from 0.96 to 3.15 ?M. The corresponding furostanol glycoside of 1, (25S)-26-[(?-d-glucopyranosyl)oxy]-22?-hydroxyfurost-5-en-3?-yl O-?-d-glucopyranosyl-(1?2)-O-[?-d-xylopyranosyl-(1?3)]-O-?-d-glucopyranosyl-(1?4)-?-d-galactopyranoside (8), was cytotoxic to the adherent cell lines of A549, HSC-4, and HSC-2 cells with IC50 values of 2.97, 11.04, and 8.25 ?M, respectively. The spirostanol lycotetroside (1) caused necrotic cell death in A549 cells in a dose-dependent manner. Alternatively, the furostanol lycotetroside (8) induced apoptotic cell death in A549 cells in a time-dependent manner, as was evident by morphological observations and flow cytometry analyses.
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Project description:A fast and efficient selective pressurized liquid extraction (sPLE) method was developed to extract secondary metabolites from complex plant matrix. Convallaria majalis L., a plant producing toxic steroids, was used as proof-of-concept. The method was optimized in the aspects of preheating, dispersant, extraction temperature and solvent, and the use of C18 as in-cell cleanup sorbent. Eight authentic natural steroids with diverse sugar moieties and hydrophobicities were selected as reference analytes and spiked to 0.1 g dried leaves. The extraction performance was evaluated based on the analytes' stability, recovery, matrix effect in the electrospray interface and the level of co-extractives. With the optimal method, the extraction was finished in 10 min. A colorless extract was obtained with recoveries ranging from 63% to 107% and absolute matrix effects ranging from 3% to 27%. The optimized method was validated by extracting 0.1 g, 0.2 g and 0.4 g spiked plant samples; method accuracy and precision were assessed by recoveries and relative standard deviations of the combined extraction-analysis workflow. The method was also tested on soil samples and indicated its suitability for measuring secondary metabolites in multiple environmental matrices. To our knowledge, this is the first time sPLE has been reported to extract plant secondary metabolites from a complex plant matrix, with satisfactory recoveries and low matrix effects. This is also the first time (s)PLE has been reported to extract plant secondary metabolites from soil. We envision the method be coupled with liquid chromatography-electrospray ionization-high resolution mass spectrometry in a standard metabolomics workflow to facilitate plant metabolomics studies.
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Project description:Two new spirostanol sapogenins (5β-spirost-25(27)-en-1β,2β,3β,5β-tetrol 3 and its 25,27-dihydro derivative, (25S)-spirostan-1β,2β,3β,5β-tetrol 4) and four new saponins were isolated from the roots and rhizomes of Convallaria majalis L. together with known sapogenins (isolated from Liliaceae): 5β-spirost-25(27)-en-1β,3β-diol 1, (25S)-spirostan-1β,3β-diol 2, 5β-spirost-25(27)-en-1β,3β,4β,5β-tetrol 5, (25S)-spirostan-1β,3β,4β,5β-tetrol 6, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 7 and (25S)-spirostan-1β,2β,3β,4β,5β-pentol 8. New steroidal saponins were found to be pentahydroxy 5-O-glycosides; 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-β-galactopyranoside 9, 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-β-arabinonoside 11, 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-O-galactoside 10 and 5β-(25S)-spirostan-1β,2β,3β,4β,5β-pentol 5-O-arabinoside 12 were isolated for the first time. The structures of those compounds were determined by NMR spectroscopy, including 2D COSY, HMBC, HSQC, NOESY, ROESY experiments, theoretical calculations of shielding constants by GIAO DFT, and mass spectrometry (FAB/LSI HR MS). An attempt was made to test biological activity, particularly as potential chemotherapeutic agents, using in silico methods. A set of 12 compounds was docked to the PDB structures of HER2 receptor and tubulin. The results indicated that diols have a higher affinity to the analyzed targets than tetrols and pentols. Two compounds (25S)-spirosten-1β,3β-diol 1 and 5β-spirost-25(27)-en-1β,2β,3β,4β,5β-pentol 5-O-galactoside 9 were selected for further evaluation of biological activity.
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