Details of Natural Product (NP)

General Information of Natural Product (ID: NP0886)
  Natural Product Name
Nicotiflorin
  Synonyms
Nicotiflorin; 17650-84-9; Kaempferol-3-O-rutinoside; Nictoflorin; NICOTIFLOROSIDE; Kaempferol-3-rutinoside; Kaempferol-3-O-beta-rutinoside; UNII-4056D20K3H; Kaempferol 3-Rutinoside; Kaempferol 3-O-rutinoside; CHEBI:69657; MFCD03427292; 4056D20K3H; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one; kaempferol 3-O-(6''-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranoside; 3-rutinosylkaempferol; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one; Nicotiflorine; Kaempferol 3-O-rutinose; Kaempferol 3-rhamno-glucoside; MLS000563045; SCHEMBL240355; CHEMBL498879; Kaempferol 3-O-beta-rutinoside; MEGxp0_000024; ACon1_002178; DTXSID50938804; HMS2268M08; HY-N1475; ZINC4349478; BDBM50378581; s3267; AKOS032962209; MCULE-3239674829; 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-; 4H-1-Benzopyran-4-one,3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-; AC-34731; AS-35049; SMR001215820; CS-0016975; W1678; C21833; 3,4',5,7-Tetrahydroxyflavone 3-rhamnoglucoside; A881516; Flavone, 3,4',5,7-tetrahydroxy-, 3-rhamnoglucoside; Kaempferol 3-O-beta -rutinoside, >=98.0% (HPLC); Q23058965; 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
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  Formula C27H30O15
  Weight 594.5
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
  InChI Key RTATXGUCZHCSNG-QHWHWDPRSA-N
  Isomeric SMILES C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O
  Canonical SMILES CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)O)O)O)O)O
  External Links PubChem ID 5318767
CAS ID 17650-84-9
NPASS ID NPC181465
CHEMBL ID CHEMBL498879
  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: 653.8 ± 377.4 µg/g
 
Locality: experimental field + Harvesting time: 2020
 Aerial parts Latvia
NP Content: 600.7 ± 216.4 µg/g
      Species Name: Prunus persica Batsch cv. 'Yuhua No. 2'
  Factor Name: Low Temperature Treatment; Glycine betaine Treatment [2]
              Species Info Factor Info
               Experiment Detail
Peach fruit (Prunus persica Batsch cv. 'Yuhua No. 2') was hand-harvested at commercial maturity (about 9-12N firmness, 10-12% total soluble solids) from a local orchard in Nanjing, China. The fresh weight of 'Yuhua No. 2' peach is about 215g and the dry weight is about 30g. The fruit shape is round and the diameter size is about 72 mm. The peaches were selected in uniform size and color and absence of any damage. The selected peaches were randomly divided into two groups, each with 360 fruits for 3 replicates. According to our previous study, 10 mmol/LGB was selected as the treatment concentration. Peach fruits were immersed in 10 mmol/LGB solution for 10 min to ensure that GB could be equally distributed on the fruits. The control fruits were soaked in sterile deionized water for 10 min. After treatment, all fruits were air dried about 30 min and stored at 0℃ with a relative humidity of 85-90% for 35 days. Mesocarp samples were collected from 18 fruits on the 7th, 14th, 21th, 28th, 35th day and frozen in liquid nitrogen, then stored at -80℃ until biochemical analysis. Another 18 fruits were removed from 0℃ after 7th, 14th, 21th, 28th, 35th day, and held at 20℃ for three days to simulate shelf condition, and then evaluated CI index, firmness and extractable juice. Each treatment was replicated three times and the experiment was conducted twice with similar results.
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               Factor Function
Glycine betaine (GB) treatment enhanced chilling tolerance throughout regulating phenolic and sugar metabolisms in peach fruit during cold storage. The alleviation of chilling injury (CI) by GB treatment may be attributed to enhancement of individual of phenolic compounds and sucrose content, and induce the activities of enzymes related to phenolic and sugar metabolisms.
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               Factor Part Location NP Content
 
Cold storage(days): 0
 Flesh tissues Nanjing, China
NP Content: 0.36 ± 0.02 mg/g fresh weight
 
Cold storage(days): 7
 Flesh tissues Nanjing, China
NP Content: 0.45 ± 0.03 mg/g fresh weight
 
10 mmol/L Glycine betaine + Cold storage(days): 7
 Flesh tissues Nanjing, China
NP Content: 0.82 ± 0.05 mg/g fresh weight
 
Cold storage(days): 21
 Flesh tissues Nanjing, China
NP Content: 0.52 ± 0.03 mg/g fresh weight
 
10 mmol/L Glycine betaine + Cold storage(days): 10
 Flesh tissues Nanjing, China
NP Content: 0.63 ± 0.03 mg/g fresh weight
 
Cold storage(days): 35
 Flesh tissues Nanjing, China
NP Content: 0.26 ± 0.02 mg/g fresh weight
 
10 mmol/L Glycine betaine + Cold storage(days): 35
 Flesh tissues Nanjing, China
NP Content: 0.43 ± 0.03 mg/g fresh weight
References
1 The Cultivation of Chelidonium majus L. Increased the Total Alkaloid Content and Cytotoxic Activity Compared with Those of Wild-Grown Plants
2 Glycine betaine reduces chilling injury in peach fruit by enhancing phenolic and sugar metabolisms