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Two new C-glycosidic ellagitannins and accompanying tannins from Lawsonia inermis leaves and their cytotoxic effects.
- Source :
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Fitoterapia . Sep2021, Vol. 153, pN.PAG-N.PAG. 1p. - Publication Year :
- 2021
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Abstract
- Investigation on tannins having antitumor properties led to the isolation of two new C -glycosidic ellagitannins (1 and 2) along with seven known ellagitannins (3 – 9) and a related polyphenolic constituent (10) from Lawsonia inermis leaves. Our intensive HRESIMS, 1D and 2D NMR, and ECD spectroscopic studies of new tannins have shown that one (1) has a monomer structure of C -glycosidic tannin, and the other (2) has a dimeric structure of 2,3- O -hexahydroxydiphenoyl glucopyranose and a C -glycosidic tannin. Among the known compounds, one (3) is a C -glycosidic tannin that was isolated first of all from nature, five were C -glycosidic tannins, vescalagin (4), 1- O -methylvescalagin (5), castalagin (6), stachyurin (7), and casuarinin (8), and one was an O- glycosidic ellagitannin, tellimagrandin II (9). The remaining phenolic constituent from the leaves was identified as valoneic acid dilactone (10). The ellagitannins 1 , and 3 – 9 demonstrated noticeable cytotoxicity on human oral squamous cell carcinoma cell lines (HSC-2, HSC-4, and Ca9–22), and lower effects on human oral normal cells (HGF, HPC, and HPLF). Tellimagrandin II (9) had the highest tumor-specific cytotoxicity, and also cleaved poly (ADP-ribose) polymerase 1 in HSC-2 cells. These findings showed that L. inermis ellagitannins may be a candidate for the production of anti-oral cancer materials. [Display omitted] • Two new (1 and 2), a first isolated from nature (3), and six knowns (4 – 9) ellagitannins, and a related phenolic (10) were isolated from leaves of L. inermis. • The ellagitannins (1 , 3 – 9) exhibited higher cytotoxicity against human oral cancer cell lines (HSC-2, HSC-4, and Ca9–22) than against human normal oral cells (HGF, HPC, and HPLF). • Tellimagrandin II (9) induced cleavage of PARP1 in HSC-2 cells. [ABSTRACT FROM AUTHOR]
- Subjects :
- *MEDICINAL plants
*POLYPHENOLS
*MOUTH tumors
*FIBROBLASTS
*TANNINS
*ANTINEOPLASTIC agents
*NUCLEAR magnetic resonance spectroscopy
*DENTAL pulp
*LEAVES
*DESCRIPTIVE statistics
*TRANSFERASES
*PLANT extracts
*CELL lines
*MOLECULAR structure
*SQUAMOUS cell carcinoma
*GINGIVA
*PERIODONTAL ligament
*SPECTRUM analysis
*PHARMACODYNAMICS
Subjects
Details
- Language :
- English
- ISSN :
- 0367326X
- Volume :
- 153
- Database :
- Academic Search Index
- Journal :
- Fitoterapia
- Publication Type :
- Academic Journal
- Accession number :
- 151856608
- Full Text :
- https://doi.org/10.1016/j.fitote.2021.104925