2019
DOI: 10.1021/acs.jnatprod.9b00073
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Structures, NMR Spectroscopic Features, and Cytotoxic Properties of Oligomeric Hellinoyl (m-GO-m-GOG)-Type Ellagitannins from the Galls of Tamarix aphylla

Abstract: Ellagitannin oligomers are large molecules habitually showing complex NMR spectra that are sometimes misinterpreted and lead to incorrect structures. Understanding the NMR spectroscopic features of a group of ellagitannins would overcome these inadequacies. In this study, investigation of the galls of Tamarix aphylla led to the isolation of three new ellagitannin oligomers, phyllagallins T1 (1), T2 (2), and Q1 (3), a known monomer nilotinin M4 (4), four known dimers, nilotinins D7 (5) and D8 (6), hirtellin B (… Show more

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Cited by 4 publications
(3 citation statements)
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“…The 1 H NMR spectrum of 1 (Figures S3-S5) displayed spectroscopic features typical of a galloyl moiety [22]; an aromatic 2H singlet (δ H 7.13, H-2 /H-6 ) that exhibits HSQC correlation with a non-oxygenated aromatic carbon (δ C 109.6, 2C, C-2 /C-6 ) and HMBC correlations with oxygenated aromatic carbon (δ C 146, 2C, C-3 /C-5 , and δ C 137.7, C-4 ), a quaternary aromatic carbon (δ C 120.5, C-1 ), and a carbonyl carbon (δ C 167.2, C-7 ). The 1 H NMR and 1 H-1 H COSY spectra of 1 (Table 1, Figures S6-S8) exhibited a resonating system of seven aliphatic proton spins at δ H 4.49-3.19 (Table 1), with a large coupling pattern of the glucose H-2 -H-5 (J H-1 -H-2 = 7.8, J H-2 -H-3 = J H-3 -H-4 = J H-4 -H-5 = 9.6 Hz), highlighting the 4 C 1 conformation of the glucopyranose moiety [23]. A large coupling constant of the glucose H-1 proton signal (δ H 4.49, J = 7.8 Hz) indicates the β-configuration of the glucose's anomeric center [22].…”
Section: Structure Determination Of the Isolated Compoundsmentioning
confidence: 99%
“…The 1 H NMR spectrum of 1 (Figures S3-S5) displayed spectroscopic features typical of a galloyl moiety [22]; an aromatic 2H singlet (δ H 7.13, H-2 /H-6 ) that exhibits HSQC correlation with a non-oxygenated aromatic carbon (δ C 109.6, 2C, C-2 /C-6 ) and HMBC correlations with oxygenated aromatic carbon (δ C 146, 2C, C-3 /C-5 , and δ C 137.7, C-4 ), a quaternary aromatic carbon (δ C 120.5, C-1 ), and a carbonyl carbon (δ C 167.2, C-7 ). The 1 H NMR and 1 H-1 H COSY spectra of 1 (Table 1, Figures S6-S8) exhibited a resonating system of seven aliphatic proton spins at δ H 4.49-3.19 (Table 1), with a large coupling pattern of the glucose H-2 -H-5 (J H-1 -H-2 = 7.8, J H-2 -H-3 = J H-3 -H-4 = J H-4 -H-5 = 9.6 Hz), highlighting the 4 C 1 conformation of the glucopyranose moiety [23]. A large coupling constant of the glucose H-1 proton signal (δ H 4.49, J = 7.8 Hz) indicates the β-configuration of the glucose's anomeric center [22].…”
Section: Structure Determination Of the Isolated Compoundsmentioning
confidence: 99%
“…Dietary polyphenols used to modulate microglial activation require gut microbiota activity to produce appropriate bioactive metabolites for the treatment of depressive symptoms. The ellagitannin-like polyphenols in pomegranate extract are poorly absorbed in the small intestine and have low bioavailability [ 113 ], and, upon reaching the colon, are biotransformed by the gut microbiota to produce the bioactive compound urolithin ( 6H-dibenzo[b, d]pyran-6-one derivatives ). Urolithin reduces microgliosis and amyloid-beta plaque deposition [ 114 ], reduces anxiety-like behaviors, and improves memory [ 115 ].…”
Section: Preventive and Therapeutic Effects Of Dietary Polyphenols On...mentioning
confidence: 99%
“…In our preceding research publications, tannin-rich plant sources including galls of T. aphylla were deciphered [15] which yields approximately 71% total extract, with hydrolyzable tannins accounting for the majority [15,16]. The highest occurring type of ellagitannins in the galls of T. aphylla, according to our previous research, are those having a sugar core with a free hydroxyl group at the C-1 position, wherein the ellagitannin tamarixinin A (TA) is the most prevalent one [17]. TA is an ellagitannin dimer (Figure 1) with a wide range of reducing functionalities (OH, CO, and C-O-C), making it an excellent agent for reducing copper ions to metal CuNPs.…”
Section: Introductionmentioning
confidence: 99%