Four new sucrose diesters of substituted truxinic acids from Trigonostemon honbaensis with their anoctamin-1 inhibitory activity

Ban, Ninh Khac; Truong, Le Van; Tiep, Tran Van; Yến, Dương Thị Hải; Đoán, Vũ Văn; Nhiệm, Nguyễn Xuân; Seo, Yohan; Namkung, W.; Kim, Seung Hyun; Tài, Bùi Hữu; Kiệm, Phan Văn

doi:10.1016/j.bioorg.2020.104058

Cited by 10 publications

(12 citation statements)

References 20 publications

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“…The NMR data of the sugar moiety of 2 were very similar to those of 1 measured in the same solvent, suggesting the presence of a sucrose (Table 1) (Supplemental Figures S8-S12), which was further confirmed by the small coupling constant of the anomeric proton of the glucose unit (δ H 5.38, d, J = 3.5 Hz), and by TLC analysis of the alkaline hydrolysis product of 2 in comparison with authentic sucrose. 11 12 tryptopholglucoside (4), 13 corchonoside C (5), 14 and 2-hydroxy-5-(2-hydroxyethyl)phenyl βd-fructofuranoside (6), 15 The NMR spectral data of compounds 3-6 were consistent with those previously reported in the literature (Supplemental Figures S13-S20). Antioxidant activity of compounds 1-6 was evaluated by peroxyl radical absorbance capacity assay.…”

Section: Resultssupporting

confidence: 85%

“…The NMR data of the sugar moiety of 2 were very similar to those of 1 measured in the same solvent, suggesting the presence of a sucrose (Table 1) (Supplemental Figures S8-S12), which was further confirmed by the small coupling constant of the anomeric proton of the glucose unit ( δ H 5.38, d, J = 3.5 Hz), and by TLC analysis of the alkaline hydrolysis product of 2 in comparison with authentic sucrose. 11 In the HMBC spectrum of 2 , H-6′ ( δ H 4.43/4.48) correlated with C-9′′ ( δ C 169.0), H-1′ ( δ H 5.42) with C-2 ( δ C 105.4), and H-6 ( δ H 4.13/4/46) with the carbonyl carbon at δ C 173.0. The above evidence confirmed that the p -coumaroyl group linked to C-6′ of the glucose, C-1′ of this glucose linked to C-2 of the fructose, and the acetyl group attached to C-6 of the fructose.…”

Section: Resultsmentioning

confidence: 90%

“…The presence of the sucrose moiety was further confirmed by TLC analysis of the alkaline hydrolysis product of 1 in comparison with authentic sucrose. 11 This evidence suggested that the chemical structure of 1 was similar to that of arillatose B 8 , but 1 had one more acetyl group. A detailed structural elucidation of compound 1 was further performed using 1 H-1 H COSY and HMBC experiments, as shown in Figure 1 (Supplemental Figures S5 and S6).…”

Section: Resultsmentioning

confidence: 97%

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Two New Acylated Sucroses From the Roots of Canna indica L. and Their Antioxidant Activity

Hieu

Trang

Tài

et al. 2021

Natural Product Communications

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Two new acylated sucroses, (6- O-axetoxyl)- β-d-fructofuranosyl-(2→1)-(6- O-feruloyl- α- d-glucopyranoside (1) and (6- O-axetoxyl)- β-d-fructofuranosyl-(2→1)-(6- O-( E)- p-coumaroyl- α- d-glucopyranoside (2), and four known compounds, 2-(3′,4′-dihydroxyphenyl)-1-propanol-4′- O-[4′′′-hydroxy-3′′′,5′′′-dimethoxybenzoyl-(→6′′)- β-d-fructofuranoside (3), tryptophol glucoside (4), corchonoside C (5), and 2-hydroxy-5-(2-hydroxyethyl)phenyl β-d-fructofuranoside (6), were isolated from the roots of Canna indica L. (Cannaceae). Their structures were determined by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of these with those reported in the literature. Antioxidant activity of compounds 1-6 were evaluated by peroxyl radical absorbance capacity assay. Compounds 1 and 3 neutralized high amounts of peroxyl radical. At a concentration of 1 µM, their ORACROO* values were 3.07 ± 0.15 and 4.27 ± 0.30, respectively, many times greater than that of trolox, which was used as an internal standard. At 10 µM, the peroxyl radical absorbance capacity of compounds 1 and 3 exhibited equivalents to 15.60 ± 0.22 and 24.91 ± 0.43 times the net protection by 1 µM of trolox.

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Section: Resultssupporting

confidence: 85%

“…The NMR data of the sugar moiety of 2 were very similar to those of 1 measured in the same solvent, suggesting the presence of a sucrose (Table 1) (Supplemental Figures S8-S12), which was further confirmed by the small coupling constant of the anomeric proton of the glucose unit ( δ H 5.38, d, J = 3.5 Hz), and by TLC analysis of the alkaline hydrolysis product of 2 in comparison with authentic sucrose. 11 In the HMBC spectrum of 2 , H-6′ ( δ H 4.43/4.48) correlated with C-9′′ ( δ C 169.0), H-1′ ( δ H 5.42) with C-2 ( δ C 105.4), and H-6 ( δ H 4.13/4/46) with the carbonyl carbon at δ C 173.0. The above evidence confirmed that the p -coumaroyl group linked to C-6′ of the glucose, C-1′ of this glucose linked to C-2 of the fructose, and the acetyl group attached to C-6 of the fructose.…”

Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 97%

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Two New Acylated Sucroses From the Roots of Canna indica L. and Their Antioxidant Activity

Hieu

Trang

Tài

et al. 2021

Natural Product Communications

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“…The general experimental procedures and measurement techniques are as the same as described in Ref. [21].…”

Section: General Experimental Proceduresmentioning

confidence: 99%

Diterpenoids from Rosmarinus officinalis L. and their nitric oxide inhibitory activity

Huyen

Oanh

2021

Vietnam Journal of Chemistry

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One icetexane diterpenoid, demethylsalvicanol (1) and four abietane diterpenoids, sageone (2), 20‐deoxocarnosol (3), 11,12,20‐trihydroxy‐abieta‐8,11,13‐triene (4), and 7αα‐ethoxyrosmanol (5) were isolated from the n‐hexane layer of the leaves and twigs of Rosmarinus officinalis L. Chemical structures of compounds were identified by ESI‐MS, 1D‐, 2D‐NMR spectra and by comparison of the spectral data in the literature. Compounds 1‐5 were evaluated anti‐inflammatory activity by inhibitory NO production, LPS stimulated on RAW 264.7 cells. At a concentration of 100 μM, compound 4 exhibited inhibitory percentage of 34.7±1.8 %, meanwhile compounds 1‐3 and 5 showed cytotoxic effect. After dilution to concentration of 20 μM, except compound 1 and 2, compounds 3‐5 did not show cytotoxic effect. Their NO inhibitory productions were ranging from 20.5±2.4 % to 26.7±1.9 %. Compounds 1, 3 and 4 have been reported for the first time from the Rosmarinus genus.

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“…Our previous chemical investigation of this plant identified four new sucrose diesters of β -truxinic acid derivatives. 8 Sucrose diesters of truxinic acid derivatives are rarely found in natural sources. A few have been previously isolated from Imperata cylindrica , Coix lachryma-jobi , Bidens parviflora , and oat grains.…”

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confidence: 99%

New Truxinic and Truxillic Acid Sucrose Diesters From the Leaves of Trigonostemon honbaensis

Ban

Tài

Thu

et al. 2021

Natural Product Communications

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A new δ-truxinic acid sucrose diester and a new ε-truxillic acid sucrose diester (named trigohonbanosides E and F) were isolated from the leaves of Trigonostemon honbaensis. Their chemical structures were determined by extensive analysis of their HR-ESI-MS and NMR spectra. At a concentration of 20 µM, trigohonbanosides E and F exhibited weak inhibitory effects on NO production in LPS-activated RAW264.7 cells with inhibitory percentages of 22.7% ± 1.1% and 18.5% ± 1.4%, respectively.

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Four new sucrose diesters of substituted truxinic acids from Trigonostemon honbaensis with their anoctamin-1 inhibitory activity

Cited by 10 publications

References 20 publications

Two New Acylated Sucroses From the Roots of Canna indica L. and Their Antioxidant Activity

Two New Acylated Sucroses From the Roots of Canna indica L. and Their Antioxidant Activity

Diterpenoids from Rosmarinus officinalis L. and their nitric oxide inhibitory activity

New Truxinic and Truxillic Acid Sucrose Diesters From the Leaves of Trigonostemon honbaensis

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