• 제목/요약/키워드: Dihydroquercetin

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Highly Sweet Compounds from North and South American Medicinal Plants

  • Kinghorn, A.Douglas
    • 생약학회지
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    • 제22권1호
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    • pp.1-12
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    • 1991
  • Nearly 50 highly sweet substances have been isolated and structurally characterized from green plants, and such compounds comprise mainly various types of terpenoids, flavonoids, and proteins. Among the sweet substances that have been studied as constituents of North and South American medicinal plants are the sesquiterpene, hernandulcin, the triterpene glycosides, abrusosides A-D, the steroidal saponins, polypodosides A and B, and the dihydroflavonol, dihydroquercetin-3-acetate. In addition, safety studies have been performed on the potently sweet substance, stevioside, from the 'sweet herb of Paraguay' (Stevia rebaudiana), a compound now produced on a commercial scale.

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Chemical Investigation of the Constitutive Flavonoid Glycosides of the Leaves of Crataegus sinaica

  • El-Mousallamy, Amani M. D.
    • Natural Product Sciences
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    • 제4권2호
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    • pp.53-57
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    • 1998
  • Leaves of Crataegus sinaica Boiss, contain the new C-glycosyl flavone $3"',4”’-di-O-acetyl-2“-O-{\alpha}-rhamnosylvitexin$, together with the hitherto unknown, dihydroflavonol 3-O-xyloside, (2R:3R)-dihydroquercetin-$3-O-{\beta}-xylopyranoside$. The known compounds (+)-catechin, (-)-epicatechin, vicenin-II, $2"-O-{\alpha}-rhamnosylvitexin$, and $4"'-O-acetyl-2"-O-{\alpha}-rhamnosylvitexin$ were also characterized. Structures were established by conventional methods of analysis and confirmed by $^1H-,\;^{13}C-NMR$, and ESI-MS.

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Food Functionality of Opuntia ficus-indica var. Cultivated in Jeju Island

  • Lee, Young-Chul;Pyo, Young-Hee;Ahn, Chae-Kyung;Kim, Soo-Hyun
    • Preventive Nutrition and Food Science
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    • 제10권1호
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    • pp.103-110
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    • 2005
  • Opuntia ficus-indica, commonly known as prickly pear cactus, is commercially grown as a food and medicinal plant in Jeju Island, Korea. The crushed pads and fruits of Opuntia ficus-indica were dried in a freeze-dryer and ground into flour to be used for food materials. The major components of proximate compositions were part of a nitrogen free extract. The major minerals were Ca (4391.2-2086.9㎎%), K (1932.1-2608.7㎎%), and Mg (800.6-1984.8㎎%). The major amino acid was glutamic acid, comprising 16.3% of total amino acids in fruit and 25.2% in pad. Dihydroflavonols were identified as (+)-trans-dihydrokaempferol and (+)-trans-dihydroquercetin. Citric acid methyl esters extracted from fruits showed inhibitory activities against monoamine oxidase-B. The presence of trimethyl citrate has been reported in other plants, but 1,3-dimethyl citrate and 1-monomethyl citrate have not been previously reported. The results of pharmacological efficacy tests, including serum biochemical and hematological parameters, autonomic nervous system, anti-inflammatory, analgestic activity, anti-diabetic activity, antithrombotic, anticoagulant, dopamine beta-hydroxylase, monoamine oxidase activity, hyperlipidemia, the respiratory system, antigastic, and anti-ulcerative actions indicate that the fruit and pad of the Opuntia ficus-indica are rich sources of food and medicinal materials.

구지뽕나무 잎의 항산화 성분 (Anti-oxidant Compounds of Cudrania tricuspidata Leaves)

  • 전인주;이성완;차자현;한정훈;황완균
    • 약학회지
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    • 제49권5호
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    • pp.416-421
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    • 2005
  • Cudrania tricuspidata Bereau (Moraceae) have been used for anti-inflammatory, anti-hepatotoxic, anti-hyper­tensive and anti-diabetic activities. In order to investigate the efficacy of antioxidant activity, the bio-activity guided fraction and isolation of Biologically active substance were performed. $H_{2}O,\;30\%,\;60\%,\;100%$ MeOH and acetone fractions were examined on the antioxidant activity by DPPH method. It was shown that $30\%,\;60\%,\;100\%$ MeOH fractions have sig­nificantly antioxidant activity. From $30\%$ MeOH fraction, two dihydroflavonoid glycosides dihydroquercetin 7-O-$\beta$-D-glu­copyranoside (I), dihydrokaempferol 7-O-$\beta$-D-glucopyranoside (V) were isolated and $60\%$ MeOH fraction, six flavonoids including quercetin 3-O-$\alpha$-L-rhamnopyranosyl($1\rightarrow6$)-$\beta$-D-glucopyranoside (II), quercetin 3-O-$\beta$-D-glucopyranoside (III), quercetin 7-O-$\beta$-D-glucopyranoside (IV), kaempferol 3-O-$\alpha$-L-rhamnopyranosyl($1\rightarrow6$)-$\beta$-D-glucopyranoside (VI), kaempferol 3-O-$\beta$-D-glucopyranoside (VII), kaempferol 7-O-$\beta$-D-glucopyranoside (VIII) were isolated. To investigate the antioxidant activities of each compounds, we measured radical scavening activity with DPPH method and anti-lipid per­oxidative efficacy on low density lipoprotein (LDL) with TBARS assay. Four compounds of quercetin glycosides (I, II, III, IV) showed significant antioxidant activity.

Inhibitory Effects of Mulberry Fruit on Intestinal Disaccharidase Activity and Hyperglycemia in Streptozotocin-Induced Diabetic Rats

  • Hong, Jung-Hee;Kim, Sang-Woon;Choi, Kyung-Ho;Choi, Sang-Won;Rhee, Soon-Jae
    • Nutritional Sciences
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    • 제7권4호
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    • pp.201-207
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    • 2004
  • The current study examined the effects of freeze-dried mulberry fruit on disaccharidase activity in the small intestine and the lowering of blood glucose in streptozotocin (STZ)-induced diabetic rats. Sprague-Dawley male rats were randomly assigned to one normal and three streptozotocin (STZ)-induced diabetic groups. The diabetic groups were fed a mulberry fruit-free diet (DM-group), 0.3% mulberry fruit diet (DM-F group) or 0.6% mulberry fruit diet (DM-2F group). After they were fed the experimental diets for three weeks, diabetes was induced with an intraperitoneal injection of streptozotocin 50 mg/kg b.w before sacrificing 9 days later using the same experimental treatments. Analyses of anthocyanins, flavonoid and 1-deoxynojirimycin (DNJ) of lyophilized mulberry fruit were carried out and the major anthocyanins were rutin (142.5 mg), isoquercitrin (10.3 mg), quercetin (5.8 mg), morin (1.6 mg) dihydroquercetin (3.83 mg), cy-3-O-glucopyranoside (230.45 mg) and cy-3-O-rutinoside (131.5 mg) on the basis of 100 g dry weight. Total DNJ content was 2.39 mg/g dry weight of lyophilized mulberry fruit. Blood glucose level decreased in the diabetic mts fed the mulberry fruit supplement. The content of the liver glycogen increased in the diabetic mts fed the mulberry fruit supplement. Disaccharidase activity in the proximal part of the intestine, such as that of maltase, sucrase and lactase in the mulberry fruit supplementation groups, were lower than that of the DM group. These results suggest that mulberry fruit possess a suppressive effect on hyperglycemia, possibly by inhibiting the activity of disaccharidase in the small intestine of rats.

Molecular Cloning and Function Analysis of an Anthocyanidin Synthase Gene from Ginkgo biloba, and Its Expression in Abiotic Stress Responses

  • Xu, Feng;Cheng, Hua;Cai, Rong;Li, Lin Ling;Chang, Jie;Zhu, Jun;Zhang, Feng Xia;Chen, Liu Ji;Wang, Yan;Cheng, Shu Han;Cheng, Shui Yuan
    • Molecules and Cells
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    • 제26권6호
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    • pp.536-547
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    • 2008
  • Anthocyanidin synthase (ANS, leucoanthocyanidin oxygenase), a 2-oxoglutarate iron-dependent oxygenase, catalyzed the penultimate step in the biosynthesis of the anthocyanin class of flavonoids, from the colorless leucoanthocyanidins to the colored anthocyanidins. The full-length cDNA and genomic DNA sequences of ANS gene (designated as GbANS) were isolated from Ginkgo biloba for the first time. The full-length cDNA of GbANS contained a 1062-bp open reading frame (ORF) encoding a 354-amino-acid protein. The genomic DNA analysis showed that GbANS gene had three exons and two introns. The deduced GbANS protein showed high identities to other plant ANSs. The conserved amino acids (H-X-D) ligating ferrous iron and residues (R-X-S) participating in 2-oxoglutarate binding were found in GbANS at the similar positions like other ANSs. Southern blot analysis indicated that GbANS belonged to a multi-gene family. The expression analysis by real-time PCR showed that GbANS expressed in a tissue-specific manner in G. biloba. GbANS was also found to be up-regulated by all of the six tested abiotic stresses, UV-B, abscisic acid, sucrose, salicylic acid, cold and ethylene, consistent with the promoter region analysis of GbANS. The recombinant protein was successfully expressed in E. coli strain with pET-28a vector. The in vitro enzyme activity assay by HPLC indicated that recombinant GbANS protein could catalyze the formation the cyanidin from leucocyanidin and conversion of dihydroquercetin to quercetin, suggesting GbANS is a bifunctional enzyme within the anthocyanidin and flavonol biosynthetic pathway.

Neuroprotective effects of antioxidant constituents isolated from Opuntia ficus-indica var. saboten Makino

  • K.J. Jung;Lee, E.H.;Kim, H.J.;Lee, J.Y.;Y.S. Song;Lee, Y.H.;J. Cho;Park, M.;Park, H.
    • 한국응용약물학회:학술대회논문집
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    • 한국응용약물학회 2003년도 Annual Meeting of KSAP : International Symposium on Pharmaceutical and Biomedical Sciences on Obesity
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    • pp.63-63
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    • 2003
  • Opuntia ficus-indicavar. saboten Makino (Cactaceae) is a tropical or subtropical plant that has been widely used as folk medicine for the treatment of diabetes, asthma, burn, edema and gastritis. The purposes of the present study were to identify antioxidant constituents from fruits and stems of the plant cultivated in Cheju island, Korea, and examine their in vitro neuroprotective activities. Using a chromatographic fractionation method, ten chemical constituents were isolated from ethyl acetate extracts. By means of chemical and spectroscopic methods, those were identified as eight flavonoids such as kaempherol (a), quercetin (b), kaempferol 3-methyl ether (c), quercetin 3-methyl ether (d), narcissin (e), dihydrokaernpferol (f), dihydroquercetin (g) and erioclictyol (h), and two terpenoids such as 3-oxo-${\alpha}$-ionol-${\beta}$-d-glucopyranoside (i) and roseoside (j). Among the isolated compounds, comrounds c~e and h~j were those reported for the first titre from the plant. Compounds b, d and g showed DPPH free radical scavenging activities with IC$\sub$50/ values of 28, 19 and 31, ${\mu}$M respectively. Compounds d and g also inhibited iron-dependent lipid peroxidation with IC$\sub$50/ values of 2.4 and 3.5 ${\mu}$M. In a primary rat cortical neuronal cell culture system, compounds b, d and g inhibited xanthine/xanthine oxidase-induced (IC$\sub$50/ values of 18.2, 2.1 and 54.6 ${\mu}$M) and H$_2$O$_2$-induced (IC$\sub$50/ values of 13.6, 1.9 and 25.7 ${\mu}$M) cytotoxicities. In addition, compounds d and g inhibited NMDA-induced excitotoxicity by 21 and 33%, and only compound d inhibited growth factor withdrawal-induced apoptosis by 31% at a tested concentration of 3 ${\mu}$M. The results suggest that the antioxidant constituents with in vitroneuroprotective activities may serve as lead chemicals for the development of neuroprotective agent.

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손바닥선인장 추출물의 플라보노이드 구조 규명 및 HPLC-PDA를 이용한 지표성분의 함량 분석 (Identification of Flavonoids from Extracts of Opuntia ficus-indica var. saboten and Content Determination of Marker Components Using HPLC-PDA)

  • 박승배;강동현;진창배;김형자
    • 한국식품영양과학회지
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    • 제46권2호
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    • pp.210-219
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    • 2017
  • 손바닥선인장으로부터 기능성식품 개발을 위하여 최적의 에탄올 추출물 탐색과 HPLC-PDA 분석방법에 의한 validation을 실시하였다. 지표성분으로 dihydrokaempferol (DHK)과 3-O-methylquercetin(3-MeQ)을 선정하여 표준화를 실시하였으며 검출법 확립을 위한 정량분석은 Luna RP-18 칼럼($4.6{\times}250mm$, $5{\mu}m$)을 이용하여 1% 인산용액과 아세토니트릴을 전개 용매로 사용하였다. 용출은 1.0 mL/min의 유속으로 기울기 용출(gradient elution) 방법을 이용하였으며, 280 nm 파장에서는 DHK를, 360 nm 파장에서는 3-MeQ를 검출한 피크 면적을 이용하여 검량곡선을 작성하여 분석하였다. 본 연구에서 확립한 분석법으로 특이성, 직선성, 정밀성, 정확성, 회수율을 검색하였다. DHK의 검량선으로부터 상관계수($R^2$) 0.9998의 우수한 직선성과 intra-day와 inter-day 분석에서 97% 이상의 회수율과 3% 미만의 RSD를 나타내 정밀성과 정확성을 입증하였다. 3-MeQ의 검량선으로부터 상관계수($R^2$) 1의 우수한 직선성과 intra-day와 inter-day 분석에서 95% 이상의 회수율과 7% 미만의 RSD를 나타내 정밀성과 정확성을 입증하였다. DHK의 검출한계는 $1.38{\mu}g/mL$, 정량한계는 $4.18{\mu}g/mL$로 나타났으며, 3-MeQ의 검출한계는 $3.49{\mu}g/mL$, 정량한계는 $10.6{\mu}g/mL$로 나타났다. 손바닥선인장 에탄올 추출물(OFSEs)은 70과 $80^{\circ}C$에서 50, 70, 80% 에탄올로 3, 4, 5, 6시간 동안 각각 추출하였으며, 지표물질의 검량곡선을 활용하여 각각의 OFSEs로부터 두 종의 지표물질 함량을 분석하였다. 본 시험법으로 분석한 지표물질의 함량은 $80^{\circ}C$에서 추출한 70% OFSE가 DHK $26.42{\pm}0.65mg/OFS100g$, 3-MeQ $3.88{\pm}0.29mg/OFS100g$의 함량을 나타내 가장 우수하게 나타났다. 다양한 OFSEs에 대하여 DPPH 자유 라디칼 소거효능과 쥐의 간 균질액을 이용한 지질과산화 저해 효능에 대한 항산화 효능은 지표물질의 함량이 가장 높은 70% OFSE에서 우수한 효능을 나타내 본 연구에서 확립한 원료 표준화를 위한 적합한 분석법임이 검증되었다. 따라서 본 연구를 통하여 HPLC-PDA를 이용한 손바닥선인장 에탄올 추출물의 DHK와 3-MeQ의 분석법은 개별인정형 건강 기능식품 기능성 원료 개발을 위한 유용한 자료로 활용될 것으로 생각한다.