Details of Natural Product (NP)

General Information of Natural Product (ID: NP1201)
  Natural Product Name
Sanguinarine
  Synonyms
SANGUINARINE; 2447-54-3; Pseudochelerythrine; Sanguinarin; sangvinarin; Veadent; SANGUINARIUM; Sangrovit; Dimethylenedioxy benzphenanthridine; UNII-AV9VK043SS; Pseudochelerythrine;Sanguinarin; Benzophenanthridine alkaloid; AV9VK043SS; [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-; CHEBI:17183; 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene; NCGC00015959-03; Sanguiritrin; CAS-2447-54-3; DSSTox_CID_25204; DSSTox_RID_80748; DSSTox_GSID_45204; 13-Methyl[1,3]benzodioxolo[5,6-C][1,3]dioxolo[4,5-I]phenanthridin-13-Ium; C20H14NO4; EINECS 219-503-3; BRN 3915507; y-Chelerythrine; SR-01000075650; sanguinarium-chloride; Spectrum_000259; Prestwick0_000987; Prestwick1_000987; Prestwick2_000987; Prestwick3_000987; Spectrum2_000724; Spectrum3_001148; Spectrum4_001838; Spectrum5_000635; Lopac-S-5890; cid_5154; C20H14NO4Cl; Lopac0_001108; BSPBio_001053; BSPBio_002675; KBioGR_002542; KBioSS_000739; ZINC706; MLS002154085; DivK1c_000495; SCHEMBL123241; SPBio_000648; SPBio_002954; BPBio1_001159; CHEMBL417799; DTXSID0045204; SCHEMBL17131945; BDBM25525; GTPL11563; KBio1_000495; KBio2_000739; KBio2_003307; KBio2_005875; KBio3_002175; NINDS_000495; HMS1571E15; HMS2098E15; BCP13614; EX-A5014; HY-N0052; Tox21_110268; 4022AH; NSC765394; s9032; AKOS025311557; Tox21_110268_1; CCG-205184; compound 1 [PMID: 28621943]; CS-3818; NSC-765394; SDCCGMLS-0066612.P001; IDI1_000495; NCGC00015959-01; NCGC00015959-02; NCGC00015959-04; NCGC00015959-05; NCGC00015959-09; NCGC00015959-16; NCGC00160289-01; NCGC00160289-02; AC-34836; M892; SMR001233394; SBI-0051077.P003; DB-046461; AB00053789; FT-0634289; N1338; C06162; AB00053789_04; 447S543; Q347392; Q-100313; SR-01000075650-7; BRD-K66898851-001-03-7; 5-Methyl-2,3:7,8-bis(methylenedioxy)benzo[c]phenanthridinium(1+); 13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium; (1,3)-Benzodioxolo(5,6-c)-1,3-dioxolo(4,5-i)phenanthridinium, 13-methyl- (9CI); 13-Methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-13-ium; 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium nitrate; 13-Methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium(1+), 9CI; 13-methyl-2H,10H-[1,3]dioxolo[4,5-i][1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridinium; 24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21),23-nonaen-24-ium; 24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{14,22}.0^{17,21}]tetracosa-1(13),2,4(8),9,11,14,16,21,23-nonaen-24-ium; 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.0^{2,10.0^{4,8.0^{14,22.0^{17,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene; UI5
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  Formula C20H14NO4+
  Weight 332.3
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
  InChI Key INVGWHRKADIJHF-UHFFFAOYSA-N
  Isomeric SMILES C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
  Canonical SMILES C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
  External Links PubChem ID 5154
CAS ID 2447-54-3
NPASS ID NPC46451
HIT ID C0388
CHEMBL ID CHEMBL417799
  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: 1.9 ± 2.1 µg/g
 
Locality: experimental field + Harvesting time: 2020
 Aerial parts Latvia
NP Content: 12.8 ± 3.6 µg/g
      Species Name: Fusarium proliferatum strain BLH 51
  Factor Name: PDB Medium [2]
              Species Info Factor Info
               Experiment Detail
Strain BLH51 used in this study was 1 of 55 endophytic fungi isolated from the leaves of M. cordata from Dabie Mountain, China. The endophytic fungi isolates were inoculated, respectively, into 500 mL Erlenmeyer flasks containing 100 mL of potato dextrose liquid medium and cultured at 28 °C with 200 recycles/minute for 10 days in a rotary shaker.
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               Factor Part Location NP Content
 
PDB Medium (28 degrees Celsius + 10Days + 200 rpm)
 leaves Dabie Mountain, China
NP Content: 178 µg/l
References
1 The Cultivation of Chelidonium majus L. Increased the Total Alkaloid Content and Cytotoxic Activity Compared with Those of Wild-Grown Plants
2 An endophytic sanguinarine-producing fungus from Macleaya cordata, Fusarium proliferatum BLH51