Details of Natural Product (NP)

General Information of Natural Product (ID: NP0930)
  Natural Product Name
Astragalin
  Synonyms
Astragalin; 480-10-4; Astragaline; kaempferol-3-glucoside; Kaempferol 3-glucoside; Kaempferol 3-O-glucoside; Kaempferol-3-O-glucoside; asragalin; Kaempferol-3-beta-monoglucoside; 3-Glucosylkaempferol; Kaempferol-3-beta-glucopyranoside; UNII-APM8UQ3Z9O; 3,4',5,7-Tetrahydroxyflavone-3-glucoside; Kaempferol 3-O-beta-D-glucopyranoside; 4H-1-Benzopyran-4-one, 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-; APM8UQ3Z9O; Kaempferol 3-O-beta-D-glucoside; CHEMBL233930; CHEBI:30200; MFCD00075932; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one; Kaempferol-3-D-glucoside; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; 3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-D-glucopyranoside; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one; Kaempferol 3-beta-D-glucopyranoside, >=97.0% (HPLC); Astraglin; Kaempferol 3-D-glucoside; 3-O-b-D-Glucopyranoside; SCHEMBL23897; K5; MLS002473092; MEGxp0_000168; ACon1_001224; cid_5282102; Kaempferol 3-b-D-glucopyranoside; BDBM226182; DTXSID801017739; HMS2227A14; HY-N0015; Kaempferol 3-beta-D-glucopyranoside; kaempferol-3-O-beta-glucopyranoside; ZINC4102435; BDBM50241243; s9289; ZB1884; AKOS015896779; CCG-269212; CS-3720; Kaempferol 3-O-beta-D-glucoside (6); MCULE-5200434087; Kaempferol-3-O-.beta.-D-glucopyranoside; NCGC00163580-01; NCGC00163580-02; AC-35088; SMR001397194; Kaempferol 3-glucoside, analytical standard; 3,4'',5,7-Tetrahydroxyflavone-3-glucoside; N1897; 3-((2S,3R,4S,5S,6R)-; 3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-; 480A104; A827420; SR-05000002271; Q-100517; Q4811191; SR-05000002271-2; 3-O-b-D-Glucopyranosyloxy-4',5,7-trihydroxyflavone; BRD-K44487476-001-01-5; Kaempferol 3-glucoside, primary pharmaceutical reference standard; 3-(beta-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl .beta.-D-glucopyranoside; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
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  Formula C21H20O11
  Weight 448.4
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m1/s1
  InChI Key JPUKWEQWGBDDQB-QSOFNFLRSA-N
  Isomeric SMILES C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
  Canonical SMILES C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
  External Links PubChem ID 5282102
CAS ID 480-10-4
NPASS ID NPC133671
HIT ID C0935
CHEMBL ID CHEMBL233930
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Cleome gynandra
  Factor Name: Variety Comparison; Developmental Stage Variation [1]
              Species Info Factor Info
               Experiment Detail
Seeds of eight different accessions (TT-00, UAG/1907C, ELG/1907C, ELG/1907B, WPK/2007, KF-14, KF-05A, KF-03) of CG were obtained from the Centre for Biodiversity Kenya Resources Centre for Indigenous Knowledge, National Museums of Kenya, and germinated in a growth chamber at the SMART FARM in KIST (Gangneung, Korea). The seeds were sown in 200 holed trays with soil at a pH of 5-7, volume density = 0.3, and E.C < 1.0 ds/m at a temperature ranging between 25 and 30 ℃, humidity 60-80%, and 16/8 h day/night condition. After 1 week, the germinated plants were transplanted to pots and transferred to the greenhouse, whose temperature conditions were maintained at 20-25 ℃. Sampling was done at vegetative, flowering, and seed set stages of the plant, and the various organs of the sampled materials were separated into roots, flowers siliques, and a combination of leaves and stem (LS).
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               Factor Function
There were significant interaction effects of growth stages and accessions that contributed to changes in compounds content and AOA. TPC accumulated in plant generative parts, whereas flavonoids accumulated in young plant organs. HPLC profiling revealed that rutin was the most abundant compound in all organs, with flowers having the highest levels, while astragalin was only found in flowers. Silique extracts, particularly accession KF-14, recorded the highest TPC, which corresponded to the strongest radical scavenging activity in ABTS and DPPH assays and a strong linear correlation. The germplasm contained accessions with significantly different and varying levels of bioactive compounds and AOA. These findings potentiate the exploitation of CG organs such as siliques for AOA, flowers for rutin and astragalin, and young shoots for flavonoids. Moreover, the significant accumulation of the compounds in particular accessions of the germplasms suggest that such superior accessions may be useful candidates in genetic breeding programs to improve CG vegetable.
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               Factor Part Location NP Content
 
Flowers: C. gynandra Accessions TT-00 + flowering stage
 Flowers Korea
NP Content: 0.69 ± 0.04 mg/g dry weight
 
Flowers: C. gynandra Accessions UAG/1907C + flowering stage
 Flowers Korea
NP Content: 0.98 ± 0.18 mg/g dry weight
 
Flowers: C. gynandra Accessions ELG/1907C + flowering stage
 Flowers Korea
NP Content: 1.05 ± 0.34 mg/g dry weight
 
Flowers: C. gynandra Accessions ELG/1907B + flowering stage
 Flowers Korea
NP Content: 2.02 ± 0.42 mg/g dry weight
 
Flowers: C. gynandra Accessions WPK/2007 + flowering stage
 Flowers Korea
NP Content: 1.02 ± 0.27 mg/g dry weight
 
Flowers: C. gynandra Accessions KF-14 + flowering stage
 Flowers Korea
NP Content: 0.54 ± 0.26 mg/g dry weight
 
Flowers: C. gynandra Accessions KF-05A + flowering stage
 Flowers Korea
NP Content: 1.28 ± 0.41 mg/g dry weight
 
Flowers: C. gynandra Accessions KF-03 + flowering stage
 Flowers Korea
NP Content: 0.80 ± 0.13 mg/g dry weight
      Species Name: Vitis vinifera cv. Pinot noir
  Factor Name: Drought Stress Treatment [2]
              Species Info Factor Info
               Experiment Detail
3-year old single shoot V. vinifera plants (cultivar Pinot noir 18 Gm grafted on Kober 5BB, 51 plants) potted in 3L pots in a sandy loam soil were used. All plants were well watered (200 mL per day) at the beginning of the experiment (04.06.2010; DAY 0; 5 plants) and water was supplied to all control plants once every day (250 mL per day), whereas water supply of stressed plants was stopped. Physiological measurements and sampling of leaves took place on 07.06.2010 (DAY 3; 5 control, 5 stressed plants), 10.06.2010 (DAY 6; 5 control, 5 stressed plants) and 12.06.2010 (DAY 8; 5 control, 10 stressed plants). Due to very hot weather conditions in June 2010 the experiment was stopped after 8 days and 12 available control plants were used to restart the drought treatment with 6 control and 6 stressed plants on 11.06.2010 and all plants were measured on 15.06.2010 (DAY 5). The mean leaf temperatures at midday were: 25 ℃ (04.06.2010; DAY 0), 31.9 ℃ (07.06.2010; DAY 3), 30.8 ℃ (15.06.2010; DAY 5), 35.8 ℃ (10.06.2010; DAY 6) and 35.7 ℃ (12.06.2010; DAY 8). The mean PAR radiation per day (measured from 6:00 am till 7:00 pm) was 144.1 µmol m-2 s-1. Each plant was used only once for physiological measurements and sampling of leaves.On every day of the experiment (day 0, 3, 5, 6, 8) the pot weight and the volumetric soil moisture content (ThetaProbe ML2x and handheld data logger Moisture Meter HH2, Delta-T Devices, Cambridge, United Kingdom) was recorded. The water potential (PWSC Model 3000, Soilmoisture Equipment Corporation, Santa Barbara, USA) was determined for the 6th leaf (representing the insertion level of the shoot from the basis) of every plant and measurement day. Chlorophyll fluorescence and gas exchange parameters of light adapted leaves were determined with the 4th and 5th leaf, whereas dark adaptation was performed only with the 5th leaf. Immediately after these non-invasive measurements, the 5th leaf was harvested, frozen in liquid nitrogen and further used for the measurement of polyphenols, selected primary metabolites and volatiles (VOCs).
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               Factor Function
The content of different groups of primary and secondary metabolites is significantly influenced by severe drought stress in grapevine leaves. The content of the majority of the metabolites (around 60% of primary metabolites, around 85% of polyphenols and about 40% of the detected and identified VOCs) increased upon drought stress treatment. Among these especially the primary metabolites citric acid and glyceric acid were strongly influenced by the short as well as the prolonged drought stress treatment, whereas all polyphenols were only induced upon the prolonged drought stress treatment.
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               Factor Part Location NP Content
 
Normal condition
 Leaves Vienna, Austria
NP Content: 1.1 ± 0.1 µg/g dry weight
 
Dry 3-5 days
 Leaves Vienna, Austria
NP Content: 1.1 ± 0.7 µg/g dry weight
 
Dry 6-8 days
 Leaves Vienna, Austria
NP Content: 6.5 ± 4.7 µg/g dry weight
References
1 Variation in Phenolic Compounds and Antioxidant Activity of Various Organs of African Cabbage ( Cleome gynandra L.) Accessions at Different Growth Stages
2 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)