Sulfonic Acid-Containing Flavonoids from the Roots of <i>Phyllanthus acidus</i>

Duong, Thuc‐Huy; Beniddir, Mehdi A.; Nguyen, Van-Kieu; Aree, Thammarat; Gallard, Jean‐François; Mac, Dinh Hung; Nguyen, Huu-Hung; Bui, Xuan-Hao; Boustié, Joël; Nguyen, Kim‐Phi‐Phung; Chavasiri, Warinthorn; Pogam, Pierre Le

doi:10.1021/acs.jnatprod.8b00322

Cited by 32 publications

(13 citation statements)

References 44 publications

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“…From the Vietnamese plant C. quadrangulare, twelve alpha-glucosidase inhibitors were isolated and elucidated, including 5-hydroxy-3,7,4 -trimethoxyflavone (1), ayanin (2), kamatakenin (3), rhamnocitrin (4), ombuin (5), myricetin-3,7,3 ,5 -tetramethyl ether (6), gardenin D (7), luteolin (12), apigenin (13), mearnsetin (14), isoorientin (15), and vitexin (16). To the best of our knowledge, compounds 4-7 and 12-14 were reported for the first time from C. quadrangulare.…”

Section: Discussionmentioning

confidence: 99%

“…The crude extract were fractioned and purified using chromatographic techniques to furnish 5-hydroxy-3,7,4 -trimethoxyflavone (1) [14], ayanin (2) [15], kumatakenin (3) [16], rhamnocitrin (4) [17], ombuin (5) [18], myricetin-3,7,3 ,5 -tetramethyl ether (6) [19], gardenin D (7) [20], luteolin (12) [21], apigenin (13) [22], mearnsetin (14) [23], vitexin (15) [24], and isoorientin (16) [25] (Figure 1). These were identified by comparing their NMR spectra with published data (Tables S1 and S2).…”

Section: Phytochemical Study and Derivatization Of Compounds 2 Andmentioning

confidence: 99%

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Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity

Dao¹,

Nguyen²,

Nguyen³

et al. 2021

Molecules

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Combretum quadrangulare Kurz is widely used in folk medicine in Eastern Asia and is associated with various ethnopharmacological properties including hepatoprotective, antipyretic, analgesic, antidysenteric, and anthelmintic activities. Previous phytochemical investigations reported the presence of numerous triterpenes (mostly cycloartanes, ursanes, lupanes, and oleananes) along with dozens of flavonoids. However, the extracts of C. quadrangulare and isolated flavonoids have not been evaluated for their alpha-glucosidase inhibition. In the frame of our efforts dedicated to the chemical investigation of Vietnamese medicinal plants and their biological activities, a phytochemical study of the MeOH extract of the leaves of C. quadrangulare using bioactive guided isolation was undertaken. In this paper, the isolation and structure elucidation of twelve known compounds, 5-hydroxy-3,7,4′-trimethoxyflavone (1), ayanin (2), kumatakenin (3), rhamnocitrin (4), ombuin (5), myricetin-3,7,3′,5′-tetramethyl ether (6), gardenin D (7), luteolin (12), apigenin (13), mearnsetin (14), isoorientin (15), and vitexin (16) were reported. Bromination was applied to compounds 2 and 3 to provide four new synthetic analogues 8–11. All isolated and synthesized compounds were evaluated for alpha-glucosidase inhibition and antibacterial activity. Compounds 4 and 5 showed moderate antibacterial activity against methicillin-resistant Staphylococcus aureus while others were inactive. All compounds failed to reveal any activity toward extended spectrum beta-lactamase-producing Escherichia coli. Compounds 2, 4, 6–9, and 11–14 showed good alpha-glucosidase inhibition with IC50 values in the range of 30.5–282.0 µM. The kinetic of enzyme inhibition showed that 8 and 11 were noncompetitive type inhibition against alpha-glucosidase. In silico molecular docking model indicated that compounds 8 and 11 were potential inhibitors against enzyme α-glucosidase.

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Section: Discussionmentioning

confidence: 99%

Section: Phytochemical Study and Derivatization Of Compounds 2 Andmentioning

confidence: 99%

Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity

Dao¹,

Nguyen²,

Nguyen³

et al. 2021

Molecules

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“…Mentioned data are consistent with the isorhamnetin-3-O-rutinoside (Narcissin) structure which has been proved by the previously published papers. The presence of this compound has been observed in other species of Artemisia such as A. sublessingiana, A. absinthium, A. vulgaris, and A. incana [ 24 , 25 ].…”

Section: Discussionmentioning

confidence: 97%

Chemical compositions, antimicrobial effects, and cytotoxicity of Asia minor wormwood (Artemisia splendens Willd.) growing in Iran

et al. 2021

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Background Artemisia splendens from the Asteraceae family is a new source of biologically active compounds. The current study investigated to evaluate antimicrobial and cytotoxicity activity of methanolic extracts and their fractions obtained from aerial parts by agar disk diffusion and MTT methods, respectively. The active fractions were subjected to preparative HPLC for isolating the pure compounds, which were structurally elucidated, by 1H and 13C NMR. Results The results showed that the methanolic extract and its 60% SPE fraction have the anti-proliferative activity on A549 cell line in comparison with the control group. Meanwhile, the methanolic extract and its 40% SPE fraction can inhibit the growth of Gram-positive strains as anti-microbial activity. The 60% SPE fraction also illustrated anti-proliferative activity on the HT-29 cell line compared to the control group. Chromatographic separations via preparative HPLC yielded 5 flavonoids and three flavonoid glycosides. Conclusion Based on the results it can be concluded that A. splendens as a potential source of cytotoxic and antimicrobial compounds can be used in pharmaceutics.

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“…• Ergosterol peroxide (4). Colorless needle; the 1 H and 13 C NMR (CDCl 3 ) spectroscopic data, see Table 2.…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…Our previous report focusing on the ethyl acetate extract revealed seven phenolic compounds with the ellagic acid being a major component (Le et al, 2018). As a continuation of our research focused on the diversity of bioactive metabolites from Vietnamese medicinal plants 4,5 , the phytochemical study was performed on the less polar extract of the title plant. Multiple chromatographic methods included normal phase silica gel column chromatography, thin-layer chromatography, and gel chromatography was applied to the n-hexane extract.…”

Section: Introductionmentioning

confidence: 99%

A further investigation on the chemical constituents from Euphorbia tirucalli growing in Binh Thuan province

Duong

2019

Sci. Tech. Dev. J.

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Introduction: Euphorbia tirucalli L. is a medicinal plant popularly distributed in Asian countries. In Vietnam, only one study on the polar extract the plant Euphorbia tirucalli growing in Binh Thuan province, Vietnam was reported, revealing several phenolic components. As of 2019, no chemical reports on the non-polar extract from the Vietnamese plant were found. This research described the isolation and elucidation of compounds isolated from the non-polar extract of E. tirucalli growing in Binh Thuan province. Method: The n-hexane extract of this plant was carried out by using normal phase silica gel column chromatography, thin-layer chromatography, and gel chromatography . Analysis of spectroscopic data and a comparison of the NMR data with that in the literature led to the structural elucidation of isolated compounds. Results: Three terpenoid compounds, euphol (1), lupenone (2), and vomifoliol (3), along with ergosterol peroxide (4), ferulic acid (5), and vanillic acid (6) were isolated and elucidated. Conclusions: Among them, compound 3 and 4 were reported in the first time from E. tirucalli.

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Sulfonic Acid-Containing Flavonoids from the Roots of Phyllanthus acidus

Cited by 32 publications

References 44 publications

Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity

Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity

Chemical compositions, antimicrobial effects, and cytotoxicity of Asia minor wormwood (Artemisia splendens Willd.) growing in Iran

A further investigation on the chemical constituents from Euphorbia tirucalli growing in Binh Thuan province

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