Chemical constituents from a Chinese fern Polypodium hastatum Thunb.

Yao, Huankai; Duan, Jingyu; Ai, Fengwei; Li, Yan

doi:10.1016/j.bse.2012.06.013

Cited by 7 publications

(2 citation statements)

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“…KR can inhibit lipopolysaccharide-induced production of nitric oxide in RAW 264.7 macrophages and reduce prostaglandin E2 accumulation as the anti-inflammatory agent (12). In order to search for the bioactive phytochemicals attenuating diabetic nephropathy, KR has been previously identified in (13,14). Herein we report the interaction between HSA and KR, evaluated using multiple fluorescence spectroscopy and molecular modeling.…”

Section: Introductionmentioning

confidence: 99%

Insight into the binding interaction of kaempferol-7-O-α-L-rhamnopyranoside with human serum albumin by multiple fluorescence spectroscopy and molecular modeling

Zhang

Chen

Zhang

et al. 2017

Experimental and Therapeutic Medicine

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Abstract. Human serum albumin (HSA) is a transporting protein that has multiple functions. The binding interaction between HSA and small molecules affects its function and efficacy of small molecules. The present study reports that kaempferol-7-O-α-L-rhamnopyranoside (KR) interacts with HSA as indicated by multiple fluorescence spectroscopy and molecular modeling. KR can quench the intrinsic fluorescence of HSA through the formation of a KR-HSA complex in a static manner. In addition, the binding site is located in subdomain IIA as confirmed by competitive experiments using site-specific warfarin and ibuprofen, and the driving forces include hydrogen bonds, van der Waals forces and electrostatic interaction derived from a thermodynamic analysis. The formation of KR-HSA is exothermic and spontaneous. Although there is no hydrophobic interaction around Tyr and Trp residues, the secondary structure of HSA changes through the formation of the KR-HSA complex. In addition, docking results visualized and further supported these results. Finally, these results can provide more information to further investigate the use of KR on the prevention of diabetic complications. IntroductionHuman serum albumin (HSA) is a 585 amino acid residue protein. In the plasma it is found at high concentrations of ~600 µM and can transport many endogenous and exogenous substances, including drugs, nutrients, toxins and hormones (1). Chemicals can bind HSA to maintain a stable concentration and lifetime in the plasma. Glycated HSA is one of the major advanced glycation end-products (AGEs) in diabetic patients and results in diabetic complications (2). Furthermore, it is a biomarker that is used to predict the control of blood glucose in diabetic patients (3). Small molecules usually inhibit the formation of AGEs derived from HSA through binding interaction and intervention in the non-enzymatic reactions, including oxidation and cross-linking (4). Phytochemicals, particularly polyphenols are important in the discovery of AGEs formation inhibitors, which may inhibit the formation of AGE (5,6). Furthermore, studies on the binding interaction between quercetin and HSA are essential to evaluate quercetin on inhibiting the formation of glycated HSA (5).The structure of HSA can be divided into three similar domains (I-III) and each includes two subdomains (A and B). For the majority of the chemicals, two primary binding sites (sites I and II) are located in subdomains IIA and IIIA, respectively. In subdomain IIA, there is a unique tryptophan residue (Trp214) that emits fluorescence following excitation (7). Although Trp, tyrosine (Tyr) and phenylalanine (Phe) residues of HSA can contribute to the fluorescence, only Trp214 has intrinsic fluorescence due to the low quantum yield of the Phe residue and the effects of ionization and some functional groups on the Tyr residue (8).Kaempferol-7-O-α-L-rhamnopyranoside (KR) is a natural flavonoid found in numerous plants, including Streblus asper (9), Cardamine leucantha (10) and Cyclocarya paliurus (11). KR...

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Section: Introductionmentioning

confidence: 99%

Insight into the binding interaction of kaempferol-7-O-α-L-rhamnopyranoside with human serum albumin by multiple fluorescence spectroscopy and molecular modeling

Zhang

Chen

Zhang

et al. 2017

Experimental and Therapeutic Medicine

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“…But to the best of our knowledge, only a coumarin was identified by Suzuki from the leaves of P. hastatum growing in Japan [4] before our investigation. In our program to discover bioactive natural products from ferns, a phytochemical investigation of this plant was carried out, and some flavonoids have been obtained [5,6]. Herein we report the isolation and structure elucidation of coumaric acid glucosides from P. hastatum.…”

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Coumaric Acid Glucosides from the Chinese Fern Polypodium hastatum

et al. 2016

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Phytochemical investigations on Polypodium hastatum have led to the isolation of three isomers of coumaric acid glucosides. Their structures were identified as trans-melilotoside (1), trans-coumaric acid-3-O-E-Dglucopyranoside (2), and trans-coumaric acid-4-O-E-D-glucopyranoside (3) by spectroscopic analysis. Compound 2 is a new natural product.Keywords: coumaric acid glucoside, structure elucidation, Polypodium. Polypodium hastatum Thunb. (Polypodiaceae) is a fern that belongs to the genus Polypodium and grows in most areas of China. In Chinese folk medicine, it is used as a phytomedicine for the treatment of urinary diseases. Previous phytochemical investigations on the genus revealed that there were triterpenoids [1], diterpenoids [2], steroids [2], flavonoids [2], polyphenols [2], and fatty acid derivatives [3]. But to the best of our knowledge, only a coumarin was identified by Suzuki from the leaves of P. hastatum growing in Japan [4] before our investigation. In our program to discover bioactive natural products from ferns, a phytochemical investigation of this plant was carried out, and some flavonoids have been obtained [5,6]. Herein we report the isolation and structure elucidation of coumaric acid glucosides from P. hastatum.Compound 2 was obtained as white crystals. The ferric chloride reaction showed a positive result. ESI-MS gave a molecular cation peak at m/z 349 [M + Na] + . The 1 H NMR spectrum (Table 1) showed two olefinic hydrogen signals at G 7.60 (1H, d, J = 16.2 Hz) and 6.40 (1H, d, J = 16.2 Hz), which indicated the presence a trans double bond. At the same time, the signals at G 7.55 (1H, s), 7.24 (1H, d, J = 7.8 Hz), 7.14 (1H, dd, J = 7.8, 8.3 Hz), and 6.98 (1H, d, J = 8.3 Hz) implied the presence of a meta-substituted benzene ring. In the 13 C NMR spectrum (Table 1), there was a carbonyl carbon signal at G 171.8. In the range of G 110-160, there were eight unsaturated carbon signals, which is in agreement with the 1 H NMR spectrum showing the occurrence of a double bond and a substituted benzene in the structure. Compared with the 13 C NMR spectra of compounds 1 and 3, it can be concluded that there was a glucoside moiety. The E-configuration of the anomeric carbon of the glucose was deduced from the coupling constant (J = 7.4 Hz) of the anomeric hydrogen signal at G 4.9. Based on the analysis and chemical reactions, it can be concluded that compound 2 was trans-coumaric acid-3-O-E-D-glucopyranoside. HMBC and HSQC further confirmed the proposed structure and assigned the 1 H and 13 C NMR data.The trans-coumaric acid-3-O-D-D-glucopyranoside was formerly synthesized by Funayama [7] through the catalysis of glucoside synthetase, but the E anomer is reported herein for the first time, and this investigation also revealed its presence in nature for the first time. In addition, as known phytochemicals, compounds 1 and 3 were indentified through comparison of the NMR data with the literature [8,9].

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Biology, Phytochemistry, Pharmacology, and Biotechnology of European Ferns, Club Mosses, and Horsetails: A Review

Szypuła

Pietrosiuk

2021

Sustainable Development and Biodiversity

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Chemical constituents from a Chinese fern Polypodium hastatum Thunb.

Cited by 7 publications

References 36 publications

Insight into the binding interaction of kaempferol-7-O-α-L-rhamnopyranoside with human serum albumin by multiple fluorescence spectroscopy and molecular modeling

Insight into the binding interaction of kaempferol-7-O-α-L-rhamnopyranoside with human serum albumin by multiple fluorescence spectroscopy and molecular modeling

Coumaric Acid Glucosides from the Chinese Fern Polypodium hastatum

Biology, Phytochemistry, Pharmacology, and Biotechnology of European Ferns, Club Mosses, and Horsetails: A Review

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