Chalcone suppresses lignin biosynthesis in illuminated soybean cells

Chen, Wei-Jun,Yun, Min-Soo,Deng, Fan,Yogo, Yasuhiro The Korean Society of Weed Science and The Turfgra 2011 Weed Biology and Management Vol.11 No.1

Lignin and its related metabolites play critical roles in plant growth and development. Thus, lignin biosynthesis has attracted interest as a novel target site of plant growth inhibitors. Chalcone has been shown to not only inhibit lignin biosynthesis in plants, but also to suppress the growth of many annual plant species. In order to know the direct effect of chalcone on plant metabolism, the effects of chalcone on the activities of key enzymes in lignin biosynthesis and on the related metabolites were clarified with a time-course study by using light-induced suspension cultures of soybean cells.The fresh weight and packed cell volume of the soybean cells were inhibited after 8 h of chalcone treatment. The activities of phenylalanine ammonia lyase (EC 4.3.1.24) and 4-coumarate: coenzyme A ligase (4CL; EC 6.2.1.12) were largely inhibited 4 h after the treatment with 0.15 $mmol\;L^{-1}$ chalcone. Unlike these two enzymes, the activity of cinnamyl alcohol dehydrogenase (EC 1.1.1.195) was not inhibited until 16 h after the chalcone treatment. The content of the 4CL substrates and lignin in the soybean cells became relatively lower than the control under the light condition within 4 h and 8 h after the chalcone treatment, respectively. These results suggest that the growth suppression of soybean cells is positively associated with the inhibition of lignin biosynthesis by exogenous chalcone.

Biosynthesis of Three Chalcone β-D-glucosides by Glycosyltransferase from Bacillus subtilis ATCC 6633

( Yinuo Fei ),( Yan Shao ),( Weiwei Wang ),( Yatian Cheng ),( Boyang Yu ),( Xiaorong He ),( Jian Zhang ) 한국미생물생명공학회(구 한국산업미생물학회) 2021 한국미생물·생명공학회지 Vol.49 No.2

Chalcones exhibit multiple biological activities. Various studies have attempted to modify the structure of chalcones with a special focus on the addition of substituents to the benzene rings. However, these chemical modifications did not improve the water solubility and bioavailability of chalcones. Glycosylation can markedly affect the physical and chemical properties of hydrophobic compounds. Here, we evaluated the ability of a highly promiscuous glycosyltransferase (GT) BsGT1 from Bacillus subtilis ATCC 6633 to biosynthesize chalcone glucosides. Purified BsGT1 catalyzed the conversion of 4'-hydroxychalcone (compound 1), 4'-hydroxy-4-methylchalcone (compound 2), and 4-hydroxy-4'-methoxychalcone (compound 3), into chalcone 4'-O-β-D-glucoside (compound 1a), 4-methylchalcone 4'-O-β-D-glucoside (compound 2a), and 4'- methoxychalcone 4-O-β-D-glucoside (compound 3a), respectively. To avoid the addition of expensive uridine diphosphate glucose (UDP-Glc), a whole-cell biotransformation system was employed to provide a natural intracellular environment for in situ co-factor regeneration. The yields of compounds 1a, 2a, and 3a were as high as 90.38%, 100% and 74.79%, respectively. The successful co-expression of BsGT1 with phosphoglucomutase (PGM) and UDP-Glc pyrophosphorylase (GalU), which are involved in the biosynthetic pathway of UDP-Glc, further improved the conversion rates of chalcones (the yields of compounds 1a and 3a increased by approximately 10%). In conclusion, we demonstrated an effective whole-cell biocatalytic system for the enzymatic biosynthesis of chalcone β-D-glucoside derivatives.

TI-I-174, a Synthetic Chalcone Derivative, Suppresses Nitric Oxide Production in Murine Macrophages via Heme Oxygenase-1 Induction and Inhibition of AP-1

( Mi Jin Kim ),( Taraman Kadayat ),( Da Eun Kim ),( Eung Seok Lee ),( Pil Hoon Park ) 한국응용약물학회 2014 Biomolecules & Therapeutics(구 응용약물학회지) Vol.22 No.5

Chalcones (1,3-diaryl-2-propen-1-ones), a flavonoid subfamily, are widely known for their anti-inflammatory properties. Propenone moiety in chalcones is known to play an important role in generating biological responses by chalcones. In the present study, we synthesized chalcone derivatives structurally modified in propenone moiety and examined inhibitory effect on nitric oxide (NO) production and its potential mechanisms. Among the chalcone derivatives used for this study, TI-I-174 (3-(2-Hydroxyphenyl)- 1-(thiophen-3-yl)prop-2-en-1-one) most potently inhibited lipopolysaccharide (LPS)-stimulated nitrite production in RAW 264.7 macrophages. TI-I-174 treatment also markedly inhibited inducible nitric oxide synthase (iNOS) expression. However, TI-I-174 did not significantly affect production of IL-6, cyclooxygenase-2 (COX-2) and tumor necrosis factor-a (TNF-a), implying that TI-I-174 inhibits production of inflammatory mediators in a selective manner. Treatment of macrophages with TI-I-174 significantly inhibited transcriptional activity of activator protein-1 (AP-1) as determined by luciferase reporter gene assay, whereas nuclear factor-Kb (NF-kB) activity was not affected by TI-I-1744. In addition, TI-I-174 significantly inhibited activation of c-Jun-N-Terminal kinase (JNK) without affecting ERK1/2 and p38MAPK, indicating that down-regulation of iNOS gene expression by TI-I-174 is mainly attributed by blockade of JNK/AP-1 activation. We also demonstrated that TI-I-174 treatment led to an increase in heme oxygenase- 1 (HO-1) expression both at mRNA and protein level. Transfection of siRNA targeting HO-1 reversed TI-I-174-mediated inhibition of nitrite production. Taken together, these results indicate that TI-I-174 suppresses NO production in LPS-stimulated RAW 264.7 macrophages via induction of HO-1 and blockade of AP-1 activation.

Fragmentation Behavior Studies of Chalcones Employing Direct Analysis in Real Time (DART)

( A. F. M. Motiur Rahman ),( Mohamed W. Attwa ),( Pervez Ahmad ),( Mohammad Baseeruddin ),( Adnan A. Kadi ) 한국질량분석학회 2013 Mass spectrometry letters Vol.4 No.2

Chalcones are naturally occurring, biologically active molecules generating interest from a wide range of research applications including synthetic methodology development, biological activity investigation and studying fragmentation patterns. In this article, a series of chalcones has been synthesized and their fragmentation behavior was studied using modern ambient ionization technique Direct Analysis in Real Time (DART). DART ion source connected with an ion trap mass spectrometer was used for the fragmentation of various substituted chalcones. The chalcones were introduced to the DART source using a glass capillary without sample preparation step. All the chalcones showed prominent molecular ion peaks [M].+ corresponding to the structures. Multistage mass spectral data MSn (MS2 and MS3) were collected for all the chalcones studied. The chalcones with substitutions at 3, 4 or 5 positions gave product ion peaks with the loss of a phenyl radical (Ph.) by radical initiated α-cleavage, while substitution at 2 position of chalcone in the A-ring gave a product ion peak with the loss of substituted styryl radical (PhCH = CH.). In case of the chalcones with the substituent at 4 positions in A and B rings gave both types of fragmentation patterns. In conclusion, chalcones can be easily characterized using modern DART interface in very short time and efficiently without any cumbersome sample pretreatment.

Fragmentation Behavior Studies of Chalcones Employing Direct Analysis in Real Time (DART)

Motiur Rahman, A.F.M.,Attwa, Mohamed W.,Ahmad, Pervez,Baseeruddin, Mohammad,Kadi, Adnan A. Korean Society for Mass Spectrometry 2013 Mass spectrometry letters Vol.4 No.2

Chalcones are naturally occurring, biologically active molecules generating interest from a wide range of research applications including synthetic methodology development, biological activity investigation and studying fragmentation patterns. In this article, a series of chalcones has been synthesized and their fragmentation behavior was studied using modern ambient ionization technique Direct Analysis in Real Time (DART). DART ion source connected with an ion trap mass spectrometer was used for the fragmentation of various substituted chalcones. The chalcones were introduced to the DART source using a glass capillary without sample preparation step. All the chalcones showed prominent molecular ion peaks $[M]^{{\cdot}+}$ corresponding to the structures. Multistage mass spectral data $MS^n$ ($MS^2$ and $MS^3$) were collected for all the chalcones studied. The chalcones with substitutions at 3, 4 or 5 positions gave product ion peaks with the loss of a phenyl radical ($Ph^{\cdot}$) by radical initiated ${\alpha}$-cleavage, while substitution at 2 position of chalcone in the A-ring gave a product ion peak with the loss of substituted styryl radical (PhCH = $CH^{\cdot}$). In case of the chalcones with the substituent at 4 positions in A and B rings gave both types of fragmentation patterns. In conclusion, chalcones can be easily characterized using modern DART interface in very short time and efficiently without any cumbersome sample pretreatment.

Introduction of amino moiety enhances the inhibitory potency of 1-tetralone chalcone derivatives against LPS-stimulated reactive oxygen species production in RAW 264.7 macrophages

Katila, Pramila,Shrestha, Aastha,Shrestha, Aarajana,Shrestha, Ritina,Park, Pil-Hoon,Lee, Eung-Seok Elsevier 2019 Bioorganic chemistry Vol.87 No.-

<P><B>Abstract</B></P> <P>The design and synthesis of a series of thirty-two halogenated 1-tetralone or 6-amino-1-tetralone chalcone derivatives was achieved by the Claisen-Schmidt condensation reaction and were evaluated for their inhibitory effects against ROS production in LPS-stimulated RAW 264.7 macrophages. It was observed that the introduction of amino moiety into 1-tetralone skeleton greatly increased the inhibitory potency compared to corresponding 1-tetralone chalcones. Among the synthesized compounds, compound <B>18</B> which consists of 6-amino-1-tetralone skeleton together with <I>o</I>-fluorobenzylidene showed the most potent ROS inhibitory effect with IC<SUB>50</SUB> value of 0.25 ± 0.13 µM. SAR analysis revealed that amino moiety at the 6th position of 1-tetralone chalcones have an important role for exerting the greater ROS inhibitory potency in LPS-stimulated RAW 264.7 macrophages than those exhibited by 1-tetralone chalcones alone.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Halogenated 1-tetralone/6-amino-1-tetralone chalcone derivatives were synthesized. </LI> <LI> ROS Inhibitory effect in LPS-stimulated RAW 264.7 macrophages was examined. </LI> <LI> Compounds <B>18</B> showed the most potent ROS inhibition potency. </LI> <LI> Intro duction of amino group at the 6th position was enhanced the ROS inhibition. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

토마토(Solanum lycopersicum L.) 품종 간 수용성 비타민과 폴리페놀계 성분 함량 변이 분석

김다은,손병구,최영환,강점순,이용재,제병일,박영훈,Kim, Daen,Son, Beunggu,Choi, Youngwhan,Kang, Jumsoon,Lee, Yongjae,Je, Beungil,Park, Younghoon 한국식물생명공학회 2020 식물생명공학회지 Vol.47 No.1

기능성 성분이 향상된 토마토 품종 개발을 위해서는 성분 정량분석법과 토마토 유전자원 간 대사성분 변이에 대한 정보의 확보가 필요하다. 본 연구에서는 토마토 유전자원23개 계통과 12개 상용 F₁ 품종을 이용하여 수용성 비타민 7종(vitamin C, B1, B2, B3, B5, B6, B9)과 폴리페놀계 성분 5종(quercetin, rutin, kaempferol, myricetin, and naringenin chalcone)에 대한 함량을 비교 분석 하였다. HPLC와 LC-MS 분석 결과, 수용성 비타민과 폴리페놀계의 주요 성분으로 vitamin C와 naringenin chalcone이 각각 검출되었으며 품종 간 높은 수준의 함량 변이가 존재함을 알 수 있었다. 반면에 vitamin B1, quercetin 과 kaempferol은 전 품종에 있어 함량이 가장 낮았다. 대사성분 함량과 토마토 과실특성 간 상관관계에 있어 서 과크기(과중)와 높은 유의성이 관찰되었는데 대부분의 성분에 있어 방울토마토 품종이 완숙용 토마토 품종보다 높은 함량을 보였다. 하지만 naringenin chalcone을 제외하고 대사성분과 과색 간의 상관관계는 뚜렷하게 나타나지 않았다. 본 결과는 토마토 육종과정에 활용될 수 있는 효율적인 대사성분 정량분석법을 제시할 뿐만 아니라 기능성 성분 고함량 육종소재 선발에 중요한 정보를 제공한다. Tomato fruit quality is determined by the contents of various functional metabolites in addition to fruit appearance. To develop tomato cultivars with higher amounts of functional compounds, an efficient quantification method is required to identify the natural variations in the compounds in the tomato germplasm. In this study, we investigated tomato varieties, which included 23 inbred lines and 12 commercial F₁ cultivars, for their contents of seven watersoluble vitamins (vitamin C, vitamins B1, B2, B3, B5, B6, and B9) and five polyphenolic compounds (quercetin, rutin, kaempferol, myricetin, and naringenin chalcone). The results of high performance liquid chromatography and liquid chromatography-mass spectrometry showed that vitamin C and naringenin chalcone were the major water-soluble vitamins and polyphenolic compounds, respectively, and their abundance was highly variable depending on the cultivar. By contrast, the contents of vitamin B1, quercetin, and kaempferol were lowest among the cultivars. With regard to the relationship between metabolic compounds and fruit characteristics, a significant association was found in fruit size, indicating that cherry tomato varieties contain higher amounts of the compounds compared to large fresh-type varieties. However, no direct association was detected in fruit color, except for naringenin chalcone. The results of this study provide new insights on the quantification of metabolic compounds and the selection of breeding materials, which are prerequisites for the development of functional tomato varieties.

Synthesis and complete assignment of NMR data of 20 chalcones

Hwang, Doseok,Hyun, Jiye,Jo, Geunhyeong,Koh, Dongsoo,Lim, Yoongho John Wiley Sons, Ltd. 2011 Magnetic resonance in chemistry Vol.49 No.1

<P><B>Abstract</B></P><P>Chalcones, intermediates in flavonoid biosynthesis, can exhibit antibacterial, antiproliferative, and anti‐inflammatory properties. Chalcones contain two benzene rings and both hydroxylated and methoxylated analogs are frequently produced by hydroxylases and <I>O</I>‐methyltransferases in plant biosynthetic pathways. Assignments of NMR peaks in the spectra of hydroxylated and/or methoxylated chalcones can help in identifying novel chalcone derivatives isolated from natural sources by referencing these data against NMR spectra obtained from known chalcones. We report here the syntheses of 20 chalcones and complete assignments of <SUP>1</SUP>H and <SUP>13</SUP>C NMR spectra. Copyright © 2010 John Wiley & Sons, Ltd.</P>

Effect of Photopolymerization on the Rate of Photocrosslink in Chalcone-based Oligomeric Compounds

최동훈,오상준,반시영,오광용,Choe, Dong Hun,O, Sang Jun,Ban, Si Yeong,O, Gwang Yong Korean Chemical Society 2001 Bulletin of the Korean Chemical Society Vol.22 No.11

A new photochemically bifunctional epoxy and dimethacrylate compounds were synthesized for investigating the photosensitivity under UV irradiation. Photosensitivity of the synthesized chalcone-based compounds was investigated by using UV-visible absorption and Fourier transformed infrared (FT-IR) spectroscopies. The result of spectroscopic analysis substantiated that the two chalcone-based compounds have functions of both photocrosslinking and photopolymerization by UV exposure in the presence of photoinitiator. Two kinds of photochemical reactions proceeded competitively during UV exposure. Particularly, we studied the effect of photopolymerization on the rate of photocrosslink due to cycloaddition in the two oligomeric compounds.

광가교성 Sulfonated Polyimide 전해질 고분자를 이용한 습도센서의 제조 및 특성 분석

임동인(Dong In Lim),공명선(Myoung Seon Gong) 한국고분자학회 2012 폴리머 Vol.36 No.4

칼콘기를 포함하는 광가교성 sulfonated polyimide(SPI) 전해질 고분자를 칼콘기를 가지는 실란 커플링제가 처 리된 알루미나 전극에 도포하여 습도센서를 제조하였다. SPI 필름 중 bis(tetramethyl)ammonium 2,2`-benzidinedisulfonate (Me4N-BDS)/4,4`-diaminochalcone(DAC)/pyromellitic dianhydride(PA)= 90/10/100 이루어진 습도센서는 20과 95 %RH 영역에서 4.48부터 2.1 kΩ까지 변화하며 좋은 직선성(Y = -0.04528X+7.69446, R2 = 0.99675)을 보여주었다. 33 %RH 와 94 %RH 사이에서 흡습과 제습과정의 응답속도는 약 79초이며, 가교화된 SPI 필름은 습도를 빠르게 검지할 수 있는 매우 효율적인 감습재료이다. 온도 의존성 계수는 -0.49 %RH/˚C이며 습도센서로서 응용시 온도 보상이 필요하다. 또한 센서의 기재를 칼콘을 포함하는 실란 커플링제로 처리한 센서는 가교와 동시에 기재에 접합되어 480시간 이상 내수성, 고온과 고습 안정성 및 장기 안정성이 뛰어남을 알 수 있었다. 이렇게 가교화된 SPI는 상용화된 센서 보다 우수한 특성을 보이는 재료로서 응용 가능성을 보여주었다. Photocurable sulfonated polyimide (SPI) polyelectrolyte containing chalcone group was prepared and fabricated on an alumina electrode pretreated with chalcone-containing silane-coupling agent. SPI films with bis(tetramethyl)ammonium 2,2`-benzidinedisulfonate (Me4N-BDS)/4,4`-diaminochalcone (DAC)/pyromellitic dianhydride (PA)= 90/10/100 possessed very linear response(Y = -0.04528X+7.69446, R2 = 0.99675) and showed resistance changing from 4.48 to 2.1kΩ between 20 and 95 %RH. The response time for absorption and desorption measurements between 33 and 94 %RH% was about 79 s, which affirmed the high efficiency of crosslinked SPI film for rapid detection of humidity. A negative temperature coefficient showing -0.49 %RH/˚C was found and proper temperature compensation should be considered in future applications. Moreover, pretreatment of the substrates with chalcone-containing silane-coupling agent was performed to improve the water durability and the stability of the humidity sensors at a high humidity and a high temperature and long-term stability for 480 h. The crosslinked SPI films anchored to electrode substrate could be a promising material for the fabrication of efficient humidity sensors with superior characteristics compared to the commercially available sensors.