Details of Natural Product (NP)

General Information of Natural Product (ID: NP1209)
  Natural Product Name
Cynaroside
  Synonyms
Cynaroside; Luteoloside; 5373-11-5; Luteolin 7-glucoside; Luteolin-7-O-glucoside; Luteolin-7-glucoside; Cinaroside; Glucoluteolin; 7-Glucoluteolin; Luteolin 7-O-glucoside; 7-Glucosylluteolin; Luteolin 7-O-beta-D-glucoside; Luteolin 7-monoglucoside; Luteolin 7-O-glucopyranoside; Flavopurposide; Daphneflavonoloside; UNII-98J6XDS46I; 7-O-beta-D-Glucosyl-5,7,3',4'-tetrahydroxyflavone; MLS002473222; 98J6XDS46I; CHEMBL233929; Luteolin-7-O-D-glucopyranoside; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; CHEBI:27994; MFCD06799436; 26811-41-6; SMR000232358; 2-(3,4-Dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-4H-1-benzopyran-4-one; Galuteolin; luteolin glucoside; 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside; 4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-7-(b-D-glucopyranosyloxy)-5-hydroxy-; 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one; Luteolin, glucoside; Luteolin monoglucoside; SR-01000867987; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one; EINECS 226-365-8; Luteolin 7-beta-glucoside; Luteolin 7-O-D-glucoside; Flavon, 3',4',5,7-tetrahydroxy-, glucoside; luteolin 7-O--D-glucoside; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-; luteolin-7-O-beta-glucoside; Luteolin 7-O-b-D-glucoside; Luteolin-7-D-glucopyranoside; SCHEMBL149118; Luteolin 7-b-D-Glucopyranoside; MEGxp0_000619; Luteolin 7-.beta.-D-glucoside; Luteolin-7-O-Glucoside ,(S); REGID_for_CID_657946; cid_5280637; DTXSID50949617; REGID_for_CID_5280637; HMS2224O21; Flavone, 3',4',5,7-tetrahydroxy-, mono-beta-D-glucopyranoside; HY-N0540; ZINC4096258; BDBM50241242; Luteolin 7-.beta.-D-glucopyranoside; s9018; AKOS015903261; AC-6054; CCG-269211; CS-5712; MCULE-8191036162; NSC 724451; NCGC00163589-01; NCGC00163589-02; AS-73889; Luteolin 7-glucoside, analytical standard; N1724; N2724; V1543; C03951; 373L115; Luteolin 7-O-beta-D-glucoside, >=98.0% (HPLC); Q2317288; SR-01000867987-2; SR-01000867987-3; Luteolin 7-glucoside, primary pharmaceutical reference standard; 2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl hexopyranoside #; Luteolin 7-O-Glucoside, United States Pharmacopeia (USP) Reference Standard; 2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-1-benzopyran-7-yl hexopyranoside; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-; 4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-7-(; A-D-glucopyranosyloxy)-5-hydroxy-; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one; 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, mono-beta-D-glucopyranoside
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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/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
  InChI Key PEFNSGRTCBGNAN-QNDFHXLGSA-N
  Isomeric SMILES C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
  Canonical SMILES C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
  External Links PubChem ID 5280637
CAS ID 5373-11-05
NPASS ID NPC189142
CHEMBL ID CHEMBL233929
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Chelidonium majus
  Factor Name: Locality Variation; Harvest Time Variation [1]
              Species Info Factor Info
               Experiment Detail
Aerial parts from five populations of Chelidonium majus were collected from the wild at the flowering stage (hereafter referred to as 'wild') for chemical analysis and biological activity testing during May 2019. Ten randomly selected plantlets were also collected from the same five populations in 2019 and planted in an organically certified experimental field of IES (57° 19′ 11.7″ N 25° 19′ 18.8″ E, 115 m altitude). The plot size was 0.8 m2, and the plant spacing was 0.2 × 0.5 m. A year later, aerial parts were collected during the flowering stage from the same populations in the experimental field (hereafter referred to as 'cultivated').
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               Factor Function
The total content of alkaloids in aqueous ethanol extracts prepared from cultivated C. majus specimens was higher than that observed in extracts prepared from wild-grown plant material. Chelidonine, sanguinarine, and chelerythrine were the main contributors to the total increase in alkaloid content. The cultivation of C. majus did not significantly affect the total content of flavonol glycosides. The observed differences in the phytochemical compositions of the C. majus extracts resulted in significant increases in the cytotoxic activities of the preparations.
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               Factor Part Location NP Content
 
Locality: wild + Harvesting time: 2019
 Aerial parts Latvia
NP Content: 135.9 ± 130.8 µg/g
 
Locality: experimental field + Harvesting time: 2020
 Aerial parts Latvia
NP Content: 53.5 ± 12.9 µg/g
      Species Name: Chrysanthemum morifolium Ram. cv. 'Gaya yellow'
  Factor Name: Photosynthetic Active Radiation Treatment [2]
              Species Info Factor Info
               Experiment Detail
After acclimation, the plants were grown independently in different light treatment chambers at 20 ± 0.2 &#8451 and 65 ± 2% humidity until the harvest date (35 days after light treatment). The white fluorescent light (70 ± 5 µmol/m2/s) was maintained for 12 h, and then each of the blue, green, red, and white lights was irradiated at 70 ± 5 µmol/m2/s for 4 h using LED arrays (DR LED Networks Co., Seoul, Republic of Korea). The spectral energy distribution of four different LED arrays was measured from 300 to 800 nm with a spectroradiometer (International Light, RPS-900, U.S.). Their maximum spectral wavelengths were 463 (blue), 518 (green), and 632 nm (red); the white LEDs had a broad spectrum. Irradiance was measured using a quantum sensor (LI-COR, LI-191, Lincoln, NE, U.S.). Water was supplied daily with top irrigation and a nutrient solution (Hoagland, pH = 5.9 ± 0.2, electrical conductivity = 1.2 dS/m) every 4 days until harvest.
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               Factor Function
A quantitation and principal component analysis biplot demonstrated that luteolin-7-O-glucoside (2), luteolin-7-O-glucuronide (3), and quercetagetin-trimethyl ether (8) were the highest polyphenols yielded under green light, and dicaffeoylquinic acid isomer (4), dicaffeoylquinic acid isomer (5), naringenin (7), and apigenin-7-O-glucuronide (6) were greatest under red light. Chlorogenic acid (1) and 1,2,6-trihydroxy-7,8-dimethoxy-3-methylanthraquinone (9) were produced in similar concentrations under both light types. The white and blue light appeared inefficient for polyphenol production.
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               Factor Part Location NP Content
 
Under blue light (spectral wavelengths: 463 nm)
 leaf Korea
NP Content: 4.8 ± 0.5 mg/kg
 
Under green light (spectral wavelengths: 518 nm)
 leaf Korea
NP Content: 13.2 ± 0.1 mg/kg
 
Under red light (spectral wavelengths: 632 nm)
 leaf Korea
NP Content: 13.9 ± 1.9 mg/kg
 
Under white light (spectral wavelengths: broad spectrum)
 leaf Korea
NP Content: 5.7 ± 1.3 mg/kg
References
1 The Cultivation of Chelidonium majus L. Increased the Total Alkaloid Content and Cytotoxic Activity Compared with Those of Wild-Grown Plants
2 Influences of four different light-emitting diode lights on flowering and polyphenol variations in the leaves of chrysanthemum (Chrysanthemum morifolium)