Theaflavoids A-C, new flavan-3-ols with potent α-glucosidase inhibitory activity from Yunnan black tea 'Jin-Ya'

Li, Na; Chen, Min; Zhu, Hongtao; Zhang, Man; Wang, Dong; Yang, Chong‐Ren; Zhang, Yingjun

doi:10.1016/j.lwt.2022.113918

Cited by 6 publications

(4 citation statements)

References 28 publications

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“…The flavanonols dihydroquercetin (10), dihydrokaempferol (11) and flavanones eriodictyol (12) and naringenin (13) possess carbonyl groups; however, they differ in the number of OH groups, resulting in the observed differences in inhibition of α-glucosidase. Flavan-3-ol (9), with the absence of the carbonyl group, displayed a notable α-glucosidase inhibition; furthermore, the presence of the rhamnosyl group at C-3 on quercitrin (14) altered the enzyme inhibition activity, which is consistent with previous research findings by Li et al,[29].…”

Section: Structural Activity Relationshipsupporting

confidence: 91%

Undescribed Cyclohexene and Benzofuran Alkenyl Derivatives from Choerospondias axillaris, a Potential Hypoglycemic Fruit

Weldetsadik,

Li,

et al. 2024

Foods

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The fruit of Choerospondias axillaris (Anacardiaceae), known as south wild jujube in China, has been consumed widely in several regions of the world to produce fruit pastille and leathers, juice, jam, and candy. A comprehensive chemical study on the fresh fruits led to the isolation and identification of 18 compounds, including 7 new (1–7) and 11 known (8–18) comprised of 5 alkenyl (cyclohexenols and cyclohexenones) derivatives (1–5), 3 benzofuran derivatives (6–8), 6 flavonoids (9–14) and 4 lignans (15–18). Their structures were elucidated by extensive spectroscopic analysis. The known lignans 15–18 were isolated from the genus Choerospondias for the first time. Most of the isolates exhibited significant inhibitory activity on α-glucosidase with IC50 values from 2.26 ± 0.06 to 43.9 ± 0.96 μM. Molecular docking experiments strongly supported the potent α-glucosidase inhibitory activity. The results indicated that C. axillaris fruits could be an excellent source of functional foods that acquire potential hypoglycemic bioactive components.

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Section: Structural Activity Relationshipsupporting

confidence: 91%

Undescribed Cyclohexene and Benzofuran Alkenyl Derivatives from Choerospondias axillaris, a Potential Hypoglycemic Fruit

Weldetsadik,

Li,

et al. 2024

Foods

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“…Te connections through-CH(2)-CH(3)-CH 2 (4)-can also be derived from the correlations identifed by 1 H-1 H COSY. Te doublet at δ H 5.18 (H-2, J = 7.0 Hz; C-2 at δ C 83.2) and the multiplet at δ H 4.55 (H-3; C-3 at δ C 67.9) are characteristic of the 2,3trans relationship of the favan-3-ol unit [21][22][23][24][25]. Te Dglucose identity of the free sugar was established based on acid hydrolysis and TLC analysis of an actual sample.…”

Section: Identifcation Of Components Ms and Various 1d Andmentioning

confidence: 99%

Careyarboside A: A New Flavan-3-ol Glycoside from the Stems of Careya arborea (Lecythidaceae)

Jeong,

Lee,

Ahn

et al. 2023

Journal of Chemistry

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A new flavan-3-ol glycoside, compound 1 (careyarboside A), was isolated from the ethanol extract of the stems of Careya arborea, together with six known compounds. Of these, three phenolic glycosides (leonuriside A, picraquassioside D, and careyarboside B) have never been previously isolated from genus Careya and family Lecythidaceae. Their chemical structures were identified using spectroscopic data, specifically HRESIMS, 1D and 2D NMR data, including 1H-1H COSY, HSQC, and HMBC. In addition, the chemical structures of the known compounds were identified through spectral comparisons with those of published values.

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“…assamica , through catalyzed oxidation by polyphenol oxidase (PPO) contained in the fresh tea leaves. Due to its fragrant aroma and various positive health effects, e.g., antioxidant, anti-hyperlipidemia, anti-hyperglycemic, and anti-microbial activities [ 1 , 2 , 3 , 4 , 5 ], it is increasingly attracting attention from both consumers and researchers as well as becoming a mainstream commodity in the international tea trade, accounting for about 80% of the global tea trade [ 6 ]. To date, nearly 100 compounds were separated from black tea, such as theaflavins [ 7 , 8 ], catechins and their derivatives [ 4 , 9 ], flavonols and related glycosides [ 3 , 10 ], flavoalkaloids [ 4 , 11 ], minorly hydrolyzable tannins [ 9 ], and alkaloids [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…The HPLC-MS combined with electrospray ionization (HPLC-ESI-MS) analysis indicated the rich presence of polyphenols. Further comprehensive chemical study on its EtOAc extract resulted in the separation and recognition of 32 phenolic compounds, which were 8 hydrolyzable tannins (1)(2)(3)(4)(5)(6)(7)(8) with one new tannin (1), 10 flavonols and its glycosides (9)(10)(11)(12)(13)(14)(15)(16)(17)(18), and 14 simple phenolics (19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32) with one new natural product (24). The antioxidant activity on the DPPH and ABTS + assays of most isolates and α-glucosidase inhibitory activity of all hydrolyzable tannins were tested.…”

Section: Introductionmentioning

confidence: 99%

New Hydrolyzable Tannin with Potent Antioxidant and α-Glucosidase Inhibitory Activity from Black Tea Produced from Camellia taliensis

Chen

Zhu

et al. 2023

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Camellia taliensis (W. W. Smith) Melchior, belonging to the genus Camellia sect. Thea., is mainly distributed from northern Myanmar to western and southwestern Yunnan province of China, and its leaves have been used to make various teas by the locals of its growing regions. The chemical constituents of C. taliensis are significantly related to those of cultivated tea plants, C. sinensis and C. sinensis var. assamica. The HPLC-ESI-MS analysis of black tea prepared from the leaves of C. taliensis showed a rich existence of polyphenols. Further comprehensive chemical study led to the separation and recognition of 32 compounds (1–32), including one new hydrolyzable tannin, 1-O-galloyl-4,6-tetrahydroxydibenzofurandicarboxyl-β-D-glucopyranose (1), and one new natural product (24). The known compounds referred to seven hydrolyzable tannins (2–8), 10 flavonols and glycosides (9–18), and 14 simple phenolics (19–32). Their structures were elucidated by comprehensive spectroscopic analyses. Among them, 20 compounds (2, 3, 6, 7, 8, 15, 17, 18, 20–22, 24–32) were isolated from black tea for the first time. Most isolates displayed obvious antioxidant activities on DPPH and ABTS+ assays, and the hydrolyzable tannins 1, 3–5, 7, and 8 exhibited stronger inhibitory activities on α-glycosidase than quercetin and acarbose (IC50 = 5.75 and 223.30 μM, respectively), with IC50 values ranging from 0.67 to 2.01 μM.

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Theaflavoids A-C, new flavan-3-ols with potent α-glucosidase inhibitory activity from Yunnan black tea 'Jin-Ya'

Cited by 6 publications

References 28 publications

Undescribed Cyclohexene and Benzofuran Alkenyl Derivatives from Choerospondias axillaris, a Potential Hypoglycemic Fruit

Undescribed Cyclohexene and Benzofuran Alkenyl Derivatives from Choerospondias axillaris, a Potential Hypoglycemic Fruit

Careyarboside A: A New Flavan-3-ol Glycoside from the Stems of Careya arborea (Lecythidaceae)

New Hydrolyzable Tannin with Potent Antioxidant and α-Glucosidase Inhibitory Activity from Black Tea Produced from Camellia taliensis

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