Diastereomeric Ellagitannin Isomers from <i>Penthorum chinense</i>

Era, Manami; Matsuo, Yosuke; Shii, Takuya; Saito, Yoshinori; Tanaka, Takashi; Jiang, Zhi‐Hong

doi:10.1021/acs.jnatprod.5b00439

Cited by 16 publications

(21 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For instance, peak 6 shows (MS2 spectrum) a fragment at m / z = 301 [M − H-288], which undergoes further fragmentation in a pattern that matches that of the HHDP group [ 24 , 25 ]. The loss of 288 amu is consistent with a hexose bonded to an 1,3,5-trihydroxybenzene, which leads to the identification of the compound as 1′,3′,5′-trihydroxybenzene 1′- O -[4,6-( S )-HHDP]-β-glucoside ( 6 ), as shown in Figure 4 [ 26 ].…”

Section: Resultsmentioning

confidence: 93%

Flavonoids and Ellagitannins Characterization, Antioxidant and Cytotoxic Activities of Phyllanthus acuminatus Vahl

Navarro

Moreira

Arnáez

et al. 2017

Plants

View full text Add to dashboard Cite

The phenolic composition of leaves from Phyllanthus acuminatus L., a plant commonly used in Costa Rica as traditional medicine, was studied using UPLC-ESI-MS on an enriched phenolic extract. A total of 20 phenolic compounds were identified, comprising eight flavonoids (two flavanones—pinocembrin isomers and six derivatives from apigenin, chrysin, quercetin, and kaempferol); seven ellagitannins, two flavan-3-ols (prodelphinidin B dimer and (epi)gallocatechin); and three phenolic acids (ellagic acid, trimethylellagic acid, and ferulic acid). All of these compounds are reported for the first time in P. acuminatus, while previously reported in the genus Phyllanthus. Antioxidant evaluation was performed for P. acuminatus phenolic extract obtaining DPPH results with a remarkably low IC50 value of 0.15 μg/mL. Also, cytotoxicity on gastric AGS and colon SW20 adenocarcinoma cell lines was evaluated, and highly promising results were obtained, with IC50 values of 11.3 μg/mL and 10.5 μg/mL, respectively. Furthermore, selectivity index values obtained when comparing cytotoxicity on normal Vero cells was SI > 20 for both cancer cell lines, indicating a particularly high selectivity. Additionally, Justicidin B, a metabolite extensively studied for its antitumoral activity, was isolated from a non-polar extract of P. acuminatus, and comparatively evaluated for both bioactivities. The DPPH value obtained for Justicidin B was moderate (IC50 = 14.28 μg/mL), while cytotoxicity values for both AGS (IC50 = 19.5 μg/mL) and SW620 (IC50 = 24.8 μg/mL) cell lines, as well as selectivity when compared with normal Vero cells (SI = 5.4 and 4.2 respectively), was good, but lower than P. acuminatus extract. These preliminary results suggest that P. acuminatus enriched phenolic extract containing flavonoids, ellagitannins, flavan-3-ols, and phenolic acids, reported for the first time in this plant, could be of interest for further cancer cytotoxicity studies to elucidate structure–bioactivity relationships, and the molecular mechanisms and pathways.

show abstract

Section: Resultsmentioning

confidence: 93%

Flavonoids and Ellagitannins Characterization, Antioxidant and Cytotoxic Activities of Phyllanthus acuminatus Vahl

Navarro

Moreira

Arnáez

et al. 2017

Plants

View full text Add to dashboard Cite

show abstract

“…The dried stems of P. chinense were extracted with 60% aqueous acetone, and the extract was fractionated by Diaion HP20SS column chromatography to produce 12 fractions, as described in the previous study. 7 Further chromatographic separation of the fractions using Sephadex LH-20, MCI-gel CHP20P, Chromatorex ODS, and Toyopearl HW40F afforded four new compounds (1−3, 5) and two known phenolic compounds that were identified as phyllanemblinin F (6) 10 and chebulic acid (7) by comparison of their spectroscopic data with those of the authentic samples.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Ellagitannins and Related Compounds from Penthorum chinense

et al. 2018

Self Cite

View full text Add to dashboard Cite

Penthorum chinense (Penthoraceae) is an herbaceous plant distributed in Eastern Asia. Its stems and leaves are traditionally used as functional tea and folk medicine for hepatic diseases. 1,2 Recent studies concerning the hepatoprotective, hypoglycemic, and DNA damage-protective effects of this plant have demonstrated its biological activities, [3][4][5] which have been associated with the antioxidant activity of polyphenols, 6 especially of their major components, i.e., the hexahydroxydiphenoyl (HHDP) esters of flavonoid glycosides. 4 During our chemical studies on polyphenols obtained from medicinal herbs and traditional food, we recently reported the presence of two rare ellagitannins having an (R)-HHDP group at C-4/C-6 of the glucose moiety, 7 which indicated the occurrence of a unique ellagitannin metabolism in this plant because this HHDP group normally exhibited the S configuration. 8 Further chromatographic separation of the fractions obtained in our previous study resulted in the isolation of four new compounds along with two known phenolic compounds. This study deals with the isolation and structure determination of the new compounds. In addition, the structural similarities of one of the new compounds to balanophotannin F (4ʹ), previously isolated from Balanophora japonica, 9 prompted us to reinvestigate this ellagitannin using DFT calculations. RESULTS AND DISCUSSIONThe dried stems of P. chinense were extracted with 60% aq. acetone, and the extract was fractionated by Diaion HP20SS column chromatography to produce 12 fractions, as described in the previous study. 7 Further chromatographic separation of the fractions using Sephadex LH-20, MCI-gel CHP20P, Chromatorex ODS, and Toyopearl HW40F afforded four new compounds (1-3, 5) and two known phenolic compounds that were identified as phyllanemblinin F (6) 10 and chebulic acid (7) by comparison of their spectroscopic data with those of the authentic samples. EXPERIMENTAL SECTION General Experimental Procedures. Ultraviolet (UV) spectra were obtained on a JASCO V-560 UV/VIS spectrophotometer (JASCO, Tokyo, Japan). Optical rotations were measured with a JASCO DIP-370 digital polarimeter. The ECD spectra were measured with a JASCO J-725N spectrophotometer. 1 H and 13 C NMR spectra were recorded on a Varian Unity Plus 500 spectrometer (Agilent Technologies, Santa Clara, CA, USA) operating at 500 and 125 MHz for the 1 H and 13 C nuclei, respectively. NMR spectra were also recorded on a JEOL JNM-AL 400 spectrometer (JEOL Ltd, Tokyo, Japan) operating at 400 and 100 MHz for the 1 H and 13 C nuclei, respectively. ESIMS data were obtained using a JEOL JMS-T100TD spectrometer. FAB-MS were recorded on a JMS700N spectrometer (JEOL Ltd) using m-nitrobenzyl alcohol or glycerol as the matrix. Column chromatography was performed using Sephadex LH-20 (25-100 mm, GE Healthcare UK Ltd., Little Chalfont, UK), MCI-gel CHP20P (75-150 mm, Mitsubishi Chemical Co., Tokyo, Japan), Diaion HP20SS (Mitsubishi Chemical Co.), Toyopearl Butyl-650C (Tosoh Bioscience Japan, Tokyo, Japan),...

show abstract

“…Hz; J5,6b = 5.6 Hz). 10 Therefore, the atropisomerism of the C-D ring linkage in 4 was suggested to be S. To confirm the total structure of 4, density functional theory (DFT) b,c Assignments may be interchanged in each co α-anomer β-anomer calculation of NMR chemical shifts for the (S)-4 and (R)-4 isomers, along with (S)-4a…”

Section: Fig 3 Decrease In the Level Of 1 On Treatment With Polyphementioning

confidence: 99%

“…Conformations of the glucose moieties of (S)-4 and (R)-4 were very similar to those of strictinin and neostrictinin, respectively. 10 The 1 H and 13 S1 and S2 in supporting information). DP4 12 and DP4+ 13 probability analyses were also performed based on calculated data, and both analyses gave a 100.0% probability for the (S)-4, supporting the validity of the structure of 4 (Fig.…”

Section: Fig 3 Decrease In the Level Of 1 On Treatment With Polyphementioning

confidence: 99%

Enzymatic oxidation of ellagitannin and a new ellagitannin metabolite from Camellia japonica leaves

et al. 2017

Self Cite

View full text Add to dashboard Cite

Polyphenols in the leaves of Camellia japonica L. at different stages of growth were analyzed by HPLC. Pedunculagin [2,3;4,6-bis-(S)-hexahydroxydiphenoyl-D-glucose] was the major polyphenol in the youngest leaves. The levels of this compound and (+)-catechin decreased as the leaves matured. The level of (-)-epicatechin did not change with leaf maturity. Enzymatic oxidation of pedunculagin was examined to investigate the mechanism of the decrease. Pedunculagin was not directly oxidized by treatment with oxidative enzymes. However, when (+)-catechin was added to the reaction mixture, the pyrogallol rings of the 4,6-hexahydroxydiphenoyl group was oxidatively cleaved to give 2H-2-oxo-pyran-6-carboxylic acid. The in vitro oxidation products were not detected in fresh leaves, but two pedunculagin oxidation products conjugated with flavan-3-ol were isolated. A new metabolite, camelliatannin I, was isolated and characterized by spectroscopic and density functional theory calculation of NMR chemical shifts.

show abstract

Diastereomeric Ellagitannin Isomers from Penthorum chinense

Cited by 16 publications

References 25 publications

Flavonoids and Ellagitannins Characterization, Antioxidant and Cytotoxic Activities of Phyllanthus acuminatus Vahl

Flavonoids and Ellagitannins Characterization, Antioxidant and Cytotoxic Activities of Phyllanthus acuminatus Vahl

Ellagitannins and Related Compounds from Penthorum chinense

Enzymatic oxidation of ellagitannin and a new ellagitannin metabolite from Camellia japonica leaves

Contact Info

Product

Resources

About