1135-24-6Relevant articles and documents
New C,O-Glycosylflavones from the Genus Silene
Olennikov,Kashchenko
, (2020)
Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s
Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis
Koreishi, Mayuko,Asayama, Fumiaki,Imanaka, Hiroyuki,Imamura, Koreyoshi,Kadota, Megumi,Tsuno, Takuo,Nakanishi, Kazuhiro
, p. 1914 - 1922 (2005)
A novel aminoacylase was purified to homogeneity from culture broth of Streptomyces mobaraensis, as evidenced by SDS-polyacrylamide gel electrophoresis (PAGE). The enzyme was a monomer with an approximate molecular mass of 100 kDa. The purified enzyme was inhibited by the presence of 1,10-phenanthroline and activated by the addition of Co2+. It was stable at temperatures of up to 60°C for 1 h at pH 7.2. It showed broad substrate specificity to N-acetylated L-amino acids. It catalyzed the hydrolysis of the amide bonds of various N-acetylated L-amino acids, except for Nε-acetyl-L-lysine and N-acetyl-L-proline. Hydrolysis of N-acetyl-L-methionine and N-acetyl-L-histidine followed Michaelis-Menten kinetics with Km values of 1.3 ± 0.1 mM and 2.7 ± 0.1 mM respectively. The enzyme also catalyzed the deacetylation of 7-aminocephalosporanic acid (7-ACA) and cephalosporin C. Moreover, feruloyl-amino acids and L-lysine derivatives of ferulic acid derivatives were synthesized in an aqueous buffer using the enzyme.
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Kindl,Billek
, p. 1044,1045 (1964)
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Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia)
Regos, Ionela,Urbanella, Andrea,Treutter, Dieter
, p. 5843 - 5852 (2009)
Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phen
Chemical studies on antioxidant mechanism of curcuminoid: Analysis of radical reaction products from curcumin
Masuda, Toshiya,Hidaka, Kayo,Shinohara, Ayumi,Maekawa, Tomomi,Takeda, Yoshio,Yamaguchi, Hidemasa
, p. 71 - 77 (1999)
In the course of studies on the antioxidant mechanism of curcumin, its radical reaction was investigated. Curcumin was reacted with radical species, which were generated from the pyrolysis of 2,2'-azobis(isobutyronitrile) under an oxygen atmosphere, and the reaction products from curcumin were followed by HPLC. The reaction at 70 °C gave several products, three of which were structurally identified to be vanillin, ferulic acid, and a dimer of curcumin after their isolation. The dimer was a newly identified compound bearing a dihydrofuran moiety, and its chemical structure was elucidated using spectroscopic analyses, especially 2D NMR techniques. A mechanism for the dimer production is proposed and its relation to curcumin's antioxidant activity discussed. The time course and gel permeation chromatography studies of the reaction were also investigated, and the results indicate that the dimer is a radical-terminated product in the initial stage.
Lavandoside from Lavandula spica flowers
Kurkin,Lamrini,Klochkov
, p. 169 - 170 (2008)
The new natural compound lavandoside with the structure ferulic acid 4-O-β-D-glucopyranoside was isolated by column chromatography over silica gel and polyamide from the extract of Lavandula spica flowers. The chemical structure of lavandoside was establi
Loganin, Loganic Acid and Periclymenoside, a New Biosidic Ester Iridoid Glucoside from Lonicera periclymenum L. (Caprifoliaceae)
Calis, Ihsan,Lahloub, Mohamed F.,Sticher, Otto
, p. 160 - 165 (1984)
Loganin (1), loganic acid (2), and periclymenoside (3) have been isolated from Lonicera periclymenum L.The structure of the new compound 3 and the identity of the others have been determined by chemical transformations and interpretation of the spectral data.
HYDROXYCINNAMIC ACID SPERMIDINE AMIDES FROM POLLEN OF CORYLUS AVELLANA L.
Meurer, Barbara,Wray, Victor,Grotjahn, Lutz,Wiermann, Rolf,Strack, Dieter
, p. 433 - 436 (1986)
Key Word Index-Corylus avellana; Betulaceae; hazelnut; pollen; hydroxycinnamic acid; polyamine; spermidine; amide.Two hydroxycinnamic acid amides from the pollen of Corylus avellane L. have been identified as (E)-caffeoyl-(E)-feruloylspermidine and di-(E)-feruloylspermidine on the basis of 1H NMR, 13C NMR and mass spectral data.
Kulshreshtha,Rastogi
, p. 2831 (1971)
Bioactive phenolic constituents from the seeds of Pharbitis nil
Kim, Ki Hyun,Ha, Sang Keun,Choi, Sang Un,Kim, Sun Yeou,Lee, Kang Ro
, p. 1425 - 1429 (2011)
Two new lignans, termed pharsyringaresinol (1) and pharbilignoside (2), a new phenylethanoid glycoside, termed pharbiniloside (3), and 22 known compounds, were isolated from the ethanol extract of the seeds of Pharbitis nil. The structures of the new compounds (1-3) were determined on the basis of spectroscopic analyses, including 2D-NMR and circular dichroism (CD) spectroscopy studies. Among the isolates, compounds 2, 11, 12, and 24 exhibited significant cytotoxicity against human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) with IC50 values ranging from 8.07 to 28.30 μM. In addition, compounds 11, 12 and 24 potently inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells, a microglia cells with IC50 values ranging from 14.7 to 19.9 μM.
Synthesis and antioxidant activity of hydroxycinnamic acid xylan esters
Wrigstedt, Pauli,Kylli, Petri,Pitkaenen, Leena,Nousiainen, Paula,Tenkanen, Maija,Sipilae, Jussi
, p. 6937 - 6943 (2010)
Naturally occurring hydroxycinnamic acids, such as ferulic and sinapic acids, are known to possess antioxidant activity. In this study, ferulic acid and sinapic acid were covalently attached to oat spelt arabinoxylan and birch wood glucuronoxylan by esterification in a two-step feasible synthesis to generate modified xylans with various degrees of substitution. The obtained derivatives were fully analyzed by FT-IR, NMR, and HPSEC experiments to confirm the esterification of xylans and the degree of substitution. The antioxidative potential of the conjugates was evaluated using the emulsion lipid oxidation test. The results demonstrate that the derivatized xylans inhibited lipid oxidation notably better than the native oat spelt and birch wood xylans. It was found that ferulic acid esters of glucuronoxylan were more efficient antioxidants than those of arabinoxylan and that sinapic acid xylan esters were more efficient than their ferulic acid counterparts.
Functionalized ionic liquid-catalyzed 1-feruloyl-sn-glycerol synthesis
Sun, Shangde,Chen, Xiaowei,Bi, Yanlan,Chen, Jingnan,Yang, Guolong,Liu, Wei
, p. 759 - 765 (2014)
Feruloyl Glycerol (FG) is a potential antioxidant and UV absorbing ingredient in food and cosmetic industries. Transesterifications of ethyl ferulate (EF) with glycerol to synthesize FG were performed using different functionalized ionic liquids (1-butylsulfonic-3-methylimidazolium tosylate, [BSO3HMIM]TS; 1-propylsulfonic-3-methylimidazolium tosylate, [PSO3HMIM]TS; 1-butylsulfonic-3-methylimidazolium trifluoromethanesulfonate, [BSO3HMIM]OTF; 1-butylsulfonic-3- methylimidazolium hydrogen sulfate, [BSO3HMIM]HSO4; N-methylimidazolium hydrogen sulfate, [HMIM]HSO4; 1-butyl-3-methylimidazolium hydroxide, [BMIM]OH; 1-butyl-3-methylimidazo tetrachloride molysite, [BMIM]FeCl4; and 1-hexyl-3-methylimidazo tetrachloride molysite, [BMIM]FeCl4) as catalysts, respectively. High EF conversion (98.0 ± 1.5 %), 1-FG (1-feruloyl-sn-glycerol) yield (88.7 ± 1.1 %) and reaction selectivity for 1-FG (90.5 ± 2.1 %) were obtained using [BSO3HMIM]TS as catalyst. The activation energy (E a), the Michaelis-Menten kinetic constant (K m), and the maximum initial reaction rate (v max) of the transesterification are 65.9 ± 3.3 kJ/mol, 1.8 ± 0.1 mol/L, and (1.6 ± 0.4) × 10-2 mol/(L min), respectively. Effects of catalyst loading, reaction temperature, and the molar ratio of EF to glycerol on EF conversion and reaction selectivity for 1-FG (1-FG yield/EF conversion) were also investigated.
Two new flavonol glycosides from Sedum Aizoon L.
Li, Wei Lin,Luo, Qiu Yan,Wu, Li Qiang,Xiao, Lei
, p. 135 - 141 (2011)
Two new flavonol glycosides, Sedacins C (1) and D (2), and two known compounds (3-4), have been isolated from the whole plant of Sedum aizoon L. Their structures have been established as 6′-O-(E)-feruloylquercetin (1) and 6′-O-(E)-feruloylisorhamnetin (2) by means of spectroscopic analysis and chemical methods. The Japan Institute of Heterocyclic Chemistry.
A novel feruloyl esterase from a soil metagenomic library with tannase activity
Yao, Jian,Chen, Qing Long,Shen, Ai Xi,Cao, Wen,Liu, Yu Huan
, p. 55 - 61 (2013)
A gene (tan410) encoding a feruloyl esterase was isolated by screening a cotton soil metagenomic library. Sequence analysis revealed that tan410 encodes a protein of 520 amino acids with a predicted molecular weight of 55 kDa. The gene was further expressed in Escherichia coli BL21 (DE3) using a pET expression system. The recombinant enzyme was purified and characterized. Its optimum temperature and pH were 35 °C and 7.0, respectively. Tan410 activity was enhanced by the addition of Mn2+, Mg2+, NH 4+ and Ni2+. Besides ethyl ferulate, methyl caffeate, and methyl p-coumarate, Tan410 can also hydrolyze methyl gallate, tannic acid, epicatechin gallate, and epigallocatechin gallate which makes Tan410 an interesting enzyme for biotechnological applications.
Acylated kaempferol diglycoside from Allium senescens
Selyutina,Tankhaeva,Olennikov
, p. 769 - 770 (2008)
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New acylated oligosaccharides from Pistacia integerrima
Ullah, Zia,Mehmood, Rashad,Imran, Muhammad,Malik, Abdul,Afzal, Rehana A.
, p. 2027 - 2032 (2013)
Integrisides A (1) and B (2), new acylated oligosaccharides, have been isolated from the n-butanol-soluble sub-fraction of the methanolic extract collected from the aerial parts of Pistacia integerrima. Their structures were elucidated by spectroscopic techniques and hydrolysis.
Jasmonate-induced changes in flavonoid metabolism in barley (Hordeum vulgare) leaves
Ishihara, Atsushi,Ogura, Yuki,Tebayashi, Shin-Ichi,Iwamura, Hajime
, p. 2176 - 2182 (2002)
The effects of jasmonic acid (JA) on secondary metabolism in barley (Hordeum vulgare L.) were investigated. A reversed-phase HPLC analysis revealed that the amount of a particular compound increased in excised barley leaf segments that had been treated with JA. This compound was purified and identified as 6?-feruloylsaponarin (1) by spectroscopic analyses and alkaline hydrolysis. A related compound, 6?-sinapoylsaponarin (2), was also found to accumulate in excised leaves independently of the JA treatment. The accumulation of these compounds was accompanied by a decrease in the saponarin (3) content. [8,9-13C]p-Coumaric acid and [2,3,4,5,6- 2H]L-phenylalanine were effectively incorporated into the hydroxycinnamoyl moieties in 1 and 2, while the degree of incorporation of the labeled precursors into the saponarin part was small. These findings indicate that the hydroxycinnamoyl moieties of 1 and 2 are synthesized de novo from phenylalanine via the phenylpropanoid pathway, and that the saponarin part is mainly provided by the constitutive pool of 3.
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Sharma et al.
, p. 2621,2622 (1972)
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Acylated iridoid glycosides with hyaluronidase inhibitory activity from the rhizomes of Picrorhiza kurroa Royle ex Benth
Morikawa, Toshio,Nakanishi, Yusuke,Inoue, Naoki,Manse, Yoshiaki,Matsuura, Hideyuki,Hamasaki, Shinya,Yoshikawa, Masayuki,Muraoka, Osamu,Ninomiya, Kiyofumi
, (2020)
Seven new acylated iridoid glycosides, picrorhizaosides A–G (1–7), were isolated from the methanol extract of the rhizomes of Picrorhiza kurroa Royle ex Benth. (Plantaginaceae), in addition to six known iridoid glycosides (8–13). The structures of these new iridoids, including their stereochemistry, were determined based on chemical and physicochemical evidence derived from NMR and MS analysis. Of the isolates, picrorhizaosides D (4, IC50 = 43.4 μM) and E (5, 35.8 μM); picrosides I (8, 60.7 μM), II (9, 22.3 μM), and IV (11, 59.2 μM); and minecoside (13, 57.2 μM), exhibited a similar or stronger hyaluronidase inhibitory activity than those of the antiallergic medicines disodium cromoglycate (64.8 μM), ketotifen fumarate (76.5 μM), and tranilast (227 μM).
Triethylamine: A potential N-base surrogate for pyridine in Knoevenagel condensation of aromatic aldehydes and malonic acid
Pawar, Hitesh S.,Wagh, Adhirath S.,Lali, Arvind M.
, p. 4962 - 4968 (2016)
Cinnamic acids are intermediates with significant potential for synthesis of several industrially important chemicals. Classically, cinnamic acids are produced through Knoevenagel condensation of aromatic aldehydes and malonic acid in the presence of an organocatalyst and large amounts of carcinogenic pyridine. An alternative pyridine free reaction scheme for Knoevenagel condensation of malonic acid and aromatic aldehydes was investigated by replacing pyridine with an aliphatic tertiary amine surrogate in toluene as the reaction medium. Of the three aliphatic tertiary amines used, namely, triethyl amine (TEA), trioctyl amine (TOA) and tributyl amine (TBA), only TEA afforded cinnamic acids in comparable yields to those obtained with pyridine. Validation through a computational analysis is attempted to provide an explanation for the observed role of TEA as an aliphatic N-base instead of TBA and TOA. The use of TEA as a mild base in place of pyridine can be seen as playing the dual role of a base catalyst as well as a phase transfer agent evidenced by the in-process ATR-FITR spectroscopy. Use of the TEA-toluene system in place of pyridine can be seen as resulting in a process that affords ease of handling, separation and recycling of the solvent and the catalyst.
Biochemical characteristics and gene cloning of a novel thermostable feruloyl esterase from Chaetomium sp.
Yang, Shao-Qing,Tang, Luo,Yan, Qiao-Juan,Zhou, Peng,Xu, Hai-Bo,Jiang, Zheng-Qiang,Zhang, Pan
, p. 328 - 336 (2013)
A feruloyl esterase from Chaetomium sp. CQ31 was purified and biochemically characterized. The purified feruloyl esterase had a specific activity of 38.6 U/mg. The molecular mass of the enzyme was estimated to be 30.2 kDa by SDS-PAGE, and 29.6 kDa by gel filtration, indicating that the enzyme was a monomer. The optimum pH and temperature of the enzyme were pH 7.5 and 60 C, respectively. It was stable over a broad pH range of 4.0-10.0, and also exhibited good thermostability. The enzyme displayed strict substrate specificity. The K m and Vmax values for methyl ferulate were 0.98 μmol/min/mg and 42.6 U/mg, respectively. Furthermore, the feruloyl esterase gene was cloned and sequenced. Open reading frame (ORF) of the feruloyl esterase gene (879-bp) encodes 274 amino acids. The deduced amino acid sequence of the feruloyl esterase gene exhibited the highest identity (79%) with that of type B feruloyl esterase from Magnaporthe oryzae.
A new phenylpropane glycoside from the rhizome of sparganium stoloniferum
Lee, Seung Young,Choi, Sang Un,Lee, Jei Hyun,Lee, Dong Ung,Lee, Kang Ro
, p. 515 - 521 (2010)
The purification of the MeOH extract from the rhizome of Sparganium stoloniferum Buch.-Hamil. (Sparganiaceae) using column chromatography furnished one new phenylpropanoid glycoside (7) and known phenolic compounds (1-6, and 8-13). The structural elucidation of 7 was based on 1D- and 2D-NMR spectroscopic data analysis to be β-D-(6-O-trans-feruloyl) fructofuranosyl-a-D-O- glucopyranoside. Compounds 1-6, and 8-13 were elucidated by spectroscopy and confirmed by comparison with reported data; 24-methylenecycloartanol (1), phydroxybenzaldehyde (2), ferulic acid (3), p-coumaric acid (4), vanillic acid (5), β-D-(1-O-acetyl- 3-O-trans-feruloyl)fructofuranosy-a-D-2',4',6'.-O- triacetyglucopyranoisde (6), β-D-(1-O-acetyl- 3,6-O-trans-diferuloyl) fructofuranosyl-a-D-2',4',6'.-O-triacetylglucopyranoisde (8), hydroxytyrosol acetate (9), hydroxytyrosol (10), isorhamnetin-3-O-rutinoside (11), n-butyl-a-D-fructofuranoside (12), and n-butyl-β-D-fructopyranoside (13). Compounds 3 and 9-13 were isolated for the first time from this plant. The isolated compounds were tested for cytotoxicity against four human tumor cell lines in vitro using a Sulforhodamin B bioassay.
Isolation and characterization of a novel tannase from a metagenomic library
Yao, Jian,Fan, Xin Jiong,Lu, Yi,Liu, Yu Huan
, p. 3812 - 3818 (2011)
A novel gene (designated as tan410) encoding tannase was isolated from a cotton field metagenomic library by functional screening. Sequence analysis revealed that tan410 encoded a protein of 521 amino acids. SDS-PAGE and gel filtration chromatography analysis of purified tannase suggested that Tan410 was a monomeric enzyme with a molecular mass of 55 kDa. The optimum temperature and pH of Tan410 were 30 °C and 6.4. The activity was enhanced by addition of Ca2+, Mg2+ and Cd2+. In addition, Tan410 was stable in the presence of 4 M NaCl. Chlorogenic acid, rosmarinic acid, ethyl ferulate, tannic acid, epicatechin gallate and epigallocathchin gallate were efficiently hydrolyzed by recombinant tannase. All of these excellent properties make Tan410 an interesting enzyme for biotechnological application.
Biomimetic oxidation of curcumin with hydrogen peroxide catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in dichloromethane.
Chauhan, Shive Murat Singh,Kandadai, Appan Srinivas,Jain, Nidhi,Kumar, Anil
, p. 1345 - 1347 (2003)
The biomimetic oxidation of curcumin, a main turmeric pigment with hydrogen peroxide catalyzed by different 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides [TAPFe(III)Cl] in dichloromethane has been studied to give a C-C coupled curcumin dimer in 40-70% yield. The structure of the dimer has been elucidated by (1)H-, (13)C-NMR, IR and FAB-Mass spectroscopic data.
Novel morpholine containing cinnamoyl amides as potent tyrosinase inhibitors
Ghafari, Shahrzad,Ranjbar, Sara,Larijani, Bagher,Amini, Mohsen,Biglar, Mahmood,Mahdavi, Mohammad,Bakhshaei, Maryam,Khoshneviszadeh, Mahsima,Sakhteman, Amirhossein,Khoshneviszadeh, Mehdi
, p. 978 - 985 (2019)
Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (IC50s were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC50 value of 15.2 ± 0.6 μM which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry.
Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
, p. 1929 - 1940 (2022/02/01)
The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
First total syntheses of four natural bioactive glucosides
Xu, Guangya,Wu, Min,Yao, Zhongquan,Lou, Hongbin,Du, Weihong,Song, Mingwei,He, Yujiao,Dong, Hongbo
supporting information, p. 1266 - 1271 (2021/02/06)
The efficient total syntheses of four biologically interesting natural glucosides Ethylconiferin, Butylconiferin, 2’-Butoxyethylconiferin and Balajaponin B, have been achieved for the first time starting from commercially available Vanilline via concise reaction sequence of 8–10 steps with the overall yield of 26–41%. This work definitely laid the foundation for the further pharmacological study of this kind of natural compounds. Meanwhile, currently developed approach could be used as a general synthetic strategy for the syntheses of other monolignol glucosides and their derivatives, and provides an opportunity for further study of the structure-activity relationship of this kind of glucosides.
A Series of Ferulic Acid Amides Reveals Unexpected Peroxiredoxin 1 Inhibitory Activity with in vivo Antidiabetic and Hypolipidemic Effects
Yasmin, Sabina,Cerchia, Carmen,Badavath, Vishnu Nayak,Laghezza, Antonio,Dal Piaz, Fabrizio,Mondal, Susanta K.,Atl?, ?zlem,Baysal, Merve,Vadivelan, Sankaran,Shankar,Siddique, Mohd Usman Mohd,Pattnaik, Ashok Kumar,Singh, Ravi Pratap,Loiodice, Fulvio,Jayaprakash, Venkatesan,Lavecchia, Antonio
, p. 484 - 498 (2020/11/02)
Insulin resistance is a major pathophysiological feature in the development of type 2 diabetes (T2DM). Ferulic acid is known for attenuating the insulin resistance and reducing the blood glucose in T2DM rats. In this work, we designed and synthesized a library of new ferulic acid amides (FAA), which could be considered as ring opening derivatives of the antidiabetic PPARγ agonists Thiazolidinediones (TZDs). However, since these compounds displayed weak PPAR transactivation capacity, we employed a proteomics approach to unravel their molecular target(s) and identified the peroxiredoxin 1 (PRDX1) as a direct binding target of FAAs. Interestingly, PRDX1, a protein with antioxidant and chaperone activity, has been implied in the development of T2DM by inducing hepatic insulin resistance. SPR, mass spectrometry-based studies, docking experiments and in vitro inhibition assay confirmed that compounds VIe and VIf bound PRDX1 and induced a dose-dependent inhibition. Furthermore, VIe and VIf significantly improved hyperglycemia and hyperlipidemia in streptozotocin-nicotinamide (STZ-NA)-induced diabetic rats as confirmed by histopathological examinations. These results provide guidance for developing the current FAAs as new potential antidiabetic agents.