1.Quantitative analysis of quercetin content of Blumea Balsamifera L. DC Dichloromethane leaf fraction using HPLC-RP-PDA and direct TLC-Bioautography
Edmark C. Kamantigue ; Johnalyn C. Go ; Essel Tolosa ; Dhennis Versoza ; Joanna V. Toralba
Philippine Journal of Health Research and Development 2022;26(1):26-32
Quercetin, a flavonoid compound which is widely distributed in plants are considered ass beneficial physiologically due to attributed bioactivity such as anti-cancer, immunomodulatory, antidiabetic, and anti-inflammatory. In this study, the quercetin content from the dried Blumea balsamifera L. DC dried leaf was macerated with 95% ethanol and the concentrated extract was purified using Modified Kupchan method and flash chromatography. All fractions were tested for the presence of flavonoids using phytochemical screening and the selected dichloromethane fraction were further purified using another round of flash chromatograph. All resulting fractions and pooled samples were tested for the antioxidant property using the developed Thin Layer Chromatography (TLC)-Bioautography and separated compounds were derivatized with DPPH. Using the optimized TLC-Bioautography method, the quercetin content in the dichloromethane fraction was analyzed and compared with a reversed phase high performance liquid chromatography hyphenated with photodiode array detector (RP-HPLC-PDA). The calculated quercetin content from the pooled sample using TLC-bioautography method is 2.25 mg/ml and from RP-HPLC-PDA is 2.02 mg/ml which was not comparable statistically using unpaired t-test (p<0.05, α=0.05
Quercetin
2.Chemical constituents from Hypericum curvisepalum.
Ming-Xia SUN ; Xue WANG ; Xiao-Xiu LI ; Teng-Fei JI ; Bo LIU
China Journal of Chinese Materia Medica 2021;46(15):3859-3864
This study explored the chemical constituents of the aerial part of Hypericum curvisepalum. Sixteen compounds were isolated from the 95% ethanol extract of H. curvisepalum with various chromatographic techniques, including a new prenylated phenyl polyketide, mysorenone D(1). Other compounds were mysorenone-A(2), mysorenone-C(3), mysorenone-B(4), peplidiforone A(5), 4-methoxy-3-(2-methylbut-3-en-2-yl)-6-phenyl-2H-pyran-2-one(6), hyperenone-A(7), 4-(3,3-dimethylallyl)oxy-6-phenyl-α-pyrone(8), peplidiforone B(9), elegaphenone(10), hypercohin A(11), hyperisampsin G(12), spathulenol(13), quercetin(14), β-sitosterol(15), and β-amyrin(16).
Benzophenones
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Hypericum
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Quercetin
3.Pharmacological activities of myricetin and its glycosides.
Chang XU ; Yi-Long LIU ; Zhi-Wei GAO ; Hua-Min JIANG ; Chang-Jie XU ; Xian LI
China Journal of Chinese Materia Medica 2020;45(15):3575-3583
Myricetin and its glycosides are important flavonols commonly found in plants, and they are natural organic compounds with diverse pharmacological activities. Numerous studies have demonstrated that myricetin and its glycosides are strong antioxidants that have great potential in preventing, alleviating and assisting the treatment of chronic non-infectious diseases such as cancer, diabetes, and cardiovascular diseases. In addition, myricetin and its glycosides also have antiviral, antibacterial, anti-inflammatory, analgesic, liver protection and other pharmacological activities. Myricetin contains more hydroxyl groups in the parent ring structure than other flavonoids, so myricetin and its glycosides have stronger pharmacological activities than other flavonols or flavonoids such as quercetin and kaempferol. Therefore, myricetin and its glycosides have great development and application prospects. In this paper, the classification and distribution of myricetin and its glycosides, their pharmacological activity and mechanism, as well as comparison with other flavonoids were reviewed. In addition, limitations of the current research and application of myricetin and its glycosides were analyzed, and the further studies on pharmacological activities as well as their dose-activity relationship, structure-activity relationship, chemical modification, biosynthesis and application prospects of myricetin and its glycosides were discussed and proposed.
Flavonoids
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Flavonols
;
Glycosides
;
Quercetin
4.Research on chemical constituents from Artemisia annua Ⅰ.
Li-Hao XIAO ; Hai-Bo LI ; Yu-Xin HUANG ; Da-Peng QIN ; Chen-Feng ZHANG ; Zhen-Zhong WANG ; Yang YU
China Journal of Chinese Materia Medica 2021;46(5):1160-1167
Chemical constituents were isolated and purified from the water extract of Artemisia annua by column chromatography of HP-20 macroporous resin, silica gel, ODS, Sephadex LH-20, HW-40, and semi-preparative RP-HPLC. Their structures were elucidated by physicochemical properties and spectral analyses. As a result, Fifteen compounds were isolated and identified as vitexnegheteroin M(1), sibricose A5(2), securoside A(3), citrusin D(4), annphenone(5), E-melilotoside(6), esculetin(7), scopoletin-7-O-β-D-glucoside(8), eleutheroside B_1(9), chrysosplenol D(10), patuletin-3-O-β-D-glucopyranoside(11), quercetin-7-O-β-D-glucoside(12), rutin(13), apigenin 6,8-di-C-β-D-glucopyranoside(14), isoschaftoside(15), among them, compounds 1-4 were identified from Artemisia for the first time. Additionally, the isolates were evaluated for their inhibitory effects on the production of PGE_2 in LPS-simulated RAW264.7 macrophages. The results showed that compounds 1, 2, 8, and 10-15 could reduce PGE_2 levels, to a certain extent.
Apigenin
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Artemisia annua
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Quercetin
;
Rutin
5.Interaction between quercetin and DNA.
Chinese Journal of Biotechnology 2020;36(12):2877-2891
Studies on the interaction between small organic molecules and DNA are important means to explore drug mechanism and new drugs. Quercetin is a polyhydroxy flavone compound with activities such as anti-cancer, anti-inflammatory, antibacterial, antiviral, hypoglycemic and anti-hypertensive, immunomodulation and cardiovascular protection. Experimental studies aim at confirming if an interaction exists between quercetin and DNA, and determining the type of interaction. The interaction between quercetin and herring DNA can be detected by fluorescence spectrometry and resonance scattering fluorescence spectrometry analysis. The mode of the interaction between quercetin and herring DNA can be detected by UV-Vis spectrophotometry and fluorescence polarization analysis. This review helps understand the in vitro interaction between quercetin and DNA, and assist the development of drugs for corresponding diseases.
DNA/genetics*
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Quercetin
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Spectrometry, Fluorescence
6.A New Flavonol Glycoside from Tristemma hirtum (Melastomataceae)
Joseph Nandjou KENFACK ; Beaudelaire Kemvoufo PONOU ; Jonas KÜHLBORN ; Rémy Bertrand TEPONNO ; Raymond Ngansop NONO ; Romuald Tématio FOUEDJOU ; Till OPATZ ; Hee Juhn PARK ; Léon Azefack TAPONDJOU
Natural Product Sciences 2018;24(3):213-218
Chemical investigation of the plant Tristemma hirtum P. Beauv (Melastomataceae) resulted to the isolation of a new flavonol glycoside named quercetin-7-O-α-D-arabinofuranoside (1), together with nine known compounds including 3′-hexadecanoyl-2′-(9aZ)-tetradecanoyl-glycerol 1′-O-[β-D-galactopyranosyl-(1″ → 6″)-α-D-galactopyranoside] (2), arjunolic acid (3), β-sitosterol-3-O-β-D-glucopyranoside (4), terminolic acid (5), quercetin (6), asiatic acid (7), maslinic acid (8), 1β-O-galloylpedunculagin (9) and 6-hydroxyapigenin 7-O-β-D-glucopyranoside (10) from the methanol extract using normal and reversed phase column chromatography. The structures of these compounds were determined by comprehensive interpretation of their spectral data mainly including 1D- 2D-NMR (¹H-¹H COSY, HSQC, and HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis.
Chromatography
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Melastomataceae
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Methanol
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Plants
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Quercetin
7.Quercetin-3-O-β-D-Glucuronide Suppresses Lipopolysaccharide-Induced JNK and ERK Phosphorylation in LPS-Challenged RAW264.7 Cells.
Jin Young PARK ; Man Sup LIM ; Song In KIM ; Hee Jae LEE ; Sung Soo KIM ; Yong Soo KWON ; Wanjoo CHUN
Biomolecules & Therapeutics 2016;24(6):610-615
Quercetin, a flavonol, has been reported to exhibit a wide range of biological properties including anti-oxidant and anti-inflammatory activities. However, pharmacological properties of quercetin-3-O-β-D-glucuronide (QG), a glycoside derivative of quercetin, have not been extensively examined. The objective of this study is to elucidate the anti-inflammatory property and underlying mechanism of QG in lipopolysaccharide (LPS)-challenged RAW264.7 macrophage cells in comparison with quercetin. QG significantly suppressed LPS-induced extracellular secretion of pro-inflammatory mediators such as nitric oxide (NO) and PGE2, and pro-inflammatory protein expressions of iNOS and COX-2. To elucidate the underlying mechanism of the anti-inflammatory property of QG, involvement of MAPK signaling pathways was examined. QG significantly attenuated LPS-induced activation of JNK and ERK in concentration-dependent manners with a negligible effect on p38. In conclusion, the present study demonstrates QG exerts anti-inflammatory activity through the suppression of JNK and ERK signaling pathways in LPS-challenged RAW264.7 macrophage cells.
Dinoprostone
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Macrophages
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Nitric Oxide
;
Phosphorylation*
;
Quercetin
8.Enzymatic synthesis of acylated quercetin 3-O-glycosides: a review.
Chinese Journal of Biotechnology 2021;37(6):1900-1918
Quercetin 3-O-glycosides (Q3Gs) are important members of quercetin glycosides with excellent pharmacological activities such as anti-oxidation, anti-inflammation, anti-cancer and anti-virus. Two representatives of Q3Gs, rutin and troxerutin, have been developed into clinical drugs, demonstrating Q3Gs have become one of the important sources of innovative drugs. However, the applications of Q3Gs in food and pharmaceutical industries are hampered by its poor bioavailability. Of the known means, selective acylation modification of Q3Gs through enzymatic catalysis to obtain Q3G esters is one of the effective ways to improve its bioavailability. Herein, the enzyme-mediated acylation of Q3Gs were reviewed in details, focusing on the four tool enzymes (acyltransferases, lipases, proteases and esterases) and the whole-cell mediated biotransformation, as well as the effect of acylations on the biological activities of Q3Gs. Furthermore, the highly efficient synthesis and diversification of acylated site for Q3G esters were also discussed. Taken together, this review provides a new perspective for further structural modifications of Q3Gs towards drug development.
Acylation
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Biological Availability
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Glycosides
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Quercetin
;
Rutin
9.Identification of flavonoids 3-hydroxylase from Silybum marianum (L.) Gaertn and its application in enhanced production of taxifolin.
Song GAO ; Jingwen ZHOU ; Jian CHEN
Chinese Journal of Biotechnology 2020;36(12):2838-2849
(2S)-taxifolin is an important flavonoid that has anti-inflammatory and anti-oxidation effects. It is widely used in pharmaceutical and nutraceutical industries. Flavone 3-hydroxylase (F3H) can catalyze the synthesis of (2S)-taxifolin and other 3-hydroxylated flavonoids from (2S)-eriodictyol. Due to the low catalytic efficiency of F3H, the titer of many 3-hydroxyflavones, such as taxifolin, synthesized by microbial method is relatively low. In this study, a SmF3H was identified from the transcriptome of Silybum marianum (L.) Gaertn. The results of fermentation showed that SmF3H can catalyze the flavone 3-hydroxylation reaction, and its catalytic efficiency was significantly higher than that of commonly used SlF3H from Solanum lycopersicum. Six promoters with different transcription strength were selected to optimize the synthesis pathway from the flavonoid precursor (2S)-naringenin to (2S)-taxifolin. The results showed that the highest titer of (2S)-taxifolin (695.90 mg/L in shake flask) could be obtained when the P(GAL7) promoter was used to control the expression of SmF3H. The titer of (2S)-taxifolin was further improved to 3.54 g/L in a 5-L fermenter, which is the highest titer according to current available literatures.
Antioxidants
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Flavonoids
;
Milk Thistle
;
Quercetin/analogs & derivatives*
10.Taxifolin Glycoside Blocks Human ether-a-go-go Related Gene K+ Channels.
Jihyun YUN ; Hyemi BAE ; Sun Eun CHOI ; Jung Ha KIM ; Young Wook CHOI ; Inja LIM ; Chung Soo LEE ; Min Won LEE ; Jae Hong KO ; Seong Jun SEO ; Hyoweon BANG
The Korean Journal of Physiology and Pharmacology 2013;17(1):37-42
Taxifolin glycoside is a new drug candidate for the treatment of atopic dermatitis (AD). Many drugs cause side effects such as long QT syndrome by blocking the human ether-a-go-go related gene (hERG) K+ channels. To determine whether taxifolin glycoside would block hERG K+ channels, we recorded hERG K+ currents using a whole-cell patch clamp technique. We found that taxifolin glycoside directly blocked hERG K+ current in a concentration-dependent manner (EC50=9.6+/-0.7 microM). The activation curve of hERG K+ channels was negatively shifted by taxifolin glycoside. In addition, taxifolin glycoside accelerated the activation time constant and reduced the onset of the inactivation time constant. These results suggest that taxifolin glycoside blocks hERG K+ channels that function by facilitating activation and inactivation process.
Dermatitis, Atopic
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Humans
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Long QT Syndrome
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Quercetin