Corilagin: First Time Isolation from the Whole Plant of Phyllanthus maderaspatensis L.

Abstract

Introduction:Corilagin, an ellagitannin (chemical name β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-d-glucose), was previously reported from other species of Phyllanthus except Phyllanthus maderaspatensis L. Therefore, the aim of the study was to isolate corilagin from P. maderaspatensis and report it as chemo-marker. Methods: The whole plant of P. maderaspatensis was subjected to hot extraction and partitioning, followed by repeated column chromatography (silica, Diaion HP-20 and Prep HPLC). The observed LC-MS/MS and NMR data were compared with reported literature to verify the structure of the isolated molecule as corilagin. Results: The LC-MS/MS chromatogram showed a peak at retention time 22.05 min, with m/z 633 for [M -H] − along with characteristic major fragments at m/z 463 [M -170 -H] − and m/z 301 [M -332 -H] − . The NMR results were also in accordance with literature. Conclusion: This is the first report on isolation of corilagin from P. maderaspatensis whole plant for standardization and quality control of the plant.

Ellagitannin, Phenols, and Flavonoids as Antibacterials from Acalypha arvensis (Euphorbiaceae)

“…Thus, this was assigned to C-7 of another gallic acid, also for H-3′′′′ (δ 4.8) with the carbonyl signal at δ 168.5 from C-7′ of the third gallic acid. Analysis of the obtained one-dimensional ( 1 H, 13 C, and DEPT) and two-dimensional (COSY, HMQC, and HMBC) NMR spectra ( supplementary data Figures S2–S7 ), and comparison with data described in the literature [ 21 , 22 , 23 ], this compound was identified as an ellagitannin (β-1- O -galloyl-3,6-(R)-hexahydroxydiphenoyl-α-D-glucose) known as corilagin ( 1 , Figure 3 ).…”

Nutritional, Antioxidant, Antimicrobial, and Anticholinesterase Properties of Phyllanthus emblica: A Study Supported by Spectroscopic and Computational Investigations

“…The structures of the isolated compounds ( 1 – 11 , Figure 1 ) were identified from the spectroscopic data [see the listed data in the experimental section ( Table 1 , Table 2 , Table 3 , Table 4 , Table 5 , Table 6 , Table 7 , Table 8 , Table 9 , Table 10 and Table 11 ) and the 1D and 2D NMR spectra composed in the Supplementary Materials file associated with this article] and the comparison with those obtained from the literature. The isolated compounds are categorized as flavonoids, naringenin 7- O -(6″- O -galloyl)- β - d -glucopyranoside ( 2 ), simple tannin-like phenolics, gallic acid ( 1 ), 3,3′-di- O -methyl ellagic acid-4′- O - β - d -glucopyranoside ( 3 ), 1- O -galloyl glycerol ( 4 ), flavogallonic acid bislactone ( 6 ), ethyl gallate ( 8 ), urolithin M5 ( 9 ), (E)- p -coumaroyl-1- O - β - d -glucopyranoside ( 10 ), and tannins, 1,6-di- O -galloyl- β - d -glucopyranoside ( 5 ), corilagin ( 7 ), and 1,2,4,6-tetra- O -galloyl- β - d -glucopyranoside ( 11 ) [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ]. According to our knowledge, among these isolates, compounds 3 and 10 are first isolated from the plant, and the 13 C NMR data of compound 2 are reported for the first time in this research.…”

“…Corilagin ( 7 ): yellow amorphous powder; 1 H NMR [CD 3 OD + D 2 O, 9/1, v / v , 600 MHz] and 13 C NMR [CD 3 OD/D 2 O, 9/1, v / v , 151 MHz] are listed in Table 7 ; its 1 H- 1 H COSY, HSQC, and HMBC spectra are composed in the Supplementary Materials [ 23 , 24 ].…”

“…4; its 1 H-1 H COSY, HSQC, and HMBC spectra are composed in the Supplementary Materials [20]. 13 C NMR [CD 3 OD/D 2 O, 9/1, v/v, 151 MHz] are listed in Table 7; its 1 H-1 H COSY, HSQC, and HMBC spectra are composed in the Supplementary Materials [23,24]. 8; its HSQC and HMBC spectra are composed in the Supplementary Materials [25].…”