Details of Natural Product (NP)

General Information of Natural Product (ID: NP0847)
  Natural Product Name
Citric Acid
  Synonyms
citric acid; 77-92-9; 2-hydroxypropane-1,2,3-tricarboxylic acid; Citric acid, anhydrous; Anhydrous citric acid; Citro; Aciletten; Citretten; Chemfill; Hydrocerol A; 1,2,3-Propanetricarboxylic acid, 2-hydroxy-; 2-hydroxy-1,2,3-propanetricarboxylic acid; Citric acid anhydrous; Kyselina citronova; 2-Hydroxytricarballylic acid; Caswell No. 221C; F 0001 (polycarboxylic acid); 3-Carboxy-3-hydroxypentane-1,5-dioic acid; 2-Hydroxypropanetricarboxylic acid; FEMA No. 2306; FEMA Number 2306; K-Lyte; Kyselina citronova [Czech]; K-Lyte DS; CCRIS 3292; HSDB 911; EPA Pesticide Chemical Code 021801; Uro-trainer; AI3-06286; UNII-XF417D3PSL; Suby G; NSC 30279; NSC 626579; BRN 0782061; Citric acid,anhydrous; MFCD00011669; CHEMBL1261; XF417D3PSL; Kyselina 2-hydroxy-1,2,3-propantrikarbonova [Czech]; Kyselina 2-hydroxy-1,2,3-propantrikarbonova; CHEBI:30769; .beta.-Hydroxytricarballylic acid; citr; NSC30279; NSC-30279; NSC626579; NSC-626579; Citric acid, 99%; NCGC00090954-03; E330; DSSTox_CID_332; E 330; beta-Hydroxytricarballylic acid; CITRATE ANION; DSSTox_RID_75520; DSSTox_GSID_20332; 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, homopolymer; Citric acid [USAN:JAN]; CAS-77-92-9; 141633-96-7; 1,3-Propanetricarboxylic acid, 2-hydroxy-; NSC-112226; EINECS 201-069-1; Citraclean; Citronensaeure; Acidum citricum; citric-acid; Citricum acidum; Citric acid bp; Anhydrous citrate; 2fwp; 4aci; 4nrm; H3cit; Citric acid, anhydrous [USP:JAN]; Citric acid,hydrous; Citric Acid,(S); Citric acid, hydrous; Citric acid (8CI); K-Lyte (Salt/Mix); 1i2s; 1o4l; 1rq2; 1y4a; 2bo4; 2c4v; 2fw6; 4to8; Citraclean (Salt/Mix); Citric acid-[13C6]; Citric Acid (Anhydrous); 10402-15-0; Spectrum3_001850; WLN: QV1XQVQ1VQ; beta-Hydroxytricarballylate; cid_311; K-Lyte/Cl (Salt/Mix); K-Lyte DS (Salt/Mix); Acidum citricum monohydrate; bmse000076; HOC(CH2COOH)2COOH; EC 201-069-1; NCIStruc1_000057; NCIStruc2_000099; NCIOpen2_004062; NCIOpen2_004502; Oprea1_502996; BSPBio_003240; Citric acid anhydrous (JAN); 4-03-00-01272 (Beilstein Handbook Reference); Citric Acid, anhydrous, USP; MLS001066346; citric acid (Fragrance Grade); Citric acid, anhydrous (USP); Anhydrous citric acid (JP17); GTPL2478; INS NO.330; Citric Acid (Industrial Grade); Citric acid, analytical standard; DTXSID3020332; BDBM14672; Citric acid, p.a., 99.5%; KBio3_002740; INS-330; 4o61; Citric acid 5% solution in water; Citric acid, Electrophoresis Grade; HMS1787N01; HMS2268B04; Pharmakon1600-01300013; ZINC895081; Citric acid 10% solution in water; HY-N1428; STR12052; 1,2,3-Tricarboxy-2-hydroxypropane; Tox21_113436; Tox21_202405; Tox21_300124; BBL002530; NSC759606; s5761; STK286098; AKOS000119911; Citric acid, LR, anhydrous, >=99%; 2-hydroxy-1,2,3-propanetricarboxylate; CS-6965; DB04272; MCULE-7981253226; NSC-759606; 3-Carboxy-3-hydroxypentane-1,5-dioate; Citric acid, >=99.5%, FCC, FG; Citric acid, ACS reagent, >=99.5%; Citric Acid, anhydrous powder, A.C.S.; 2-Hydroxy-1,3-propanetricarboxylic acid; NCGC00090954-01; NCGC00090954-02; NCGC00090954-04; NCGC00090954-05; NCGC00254055-01; NCGC00259954-01; BP-31028; Citric Acid, anhydrous granular, A.C.S.; NCI60_022579; SMR000471840; 2-hydroxy-1,2,3-propanetricarboxyic acid; Citric acid 50% solution in water (w/w); SBI-0206765.P001; Citric acid, SAJ first grade, >=99.5%; 2-Hydroxy-1,2,3-propane tricarboxylic acid; 2-Hydroxy-1,2,3-propanenetricarboxylic acid; B7297; C1949; Citric Acid, Aqueous Solution (Food Grade); Citric acid, Vetec(TM) reagent grade, 99%; E-330; FT-0623957; FT-0665073; FT-0728530; C00158; D00037; AE-562/40806920; Citric acid, BioUltra, anhydrous, >=99.5% (T); Q159683; J-520099; 1,2,3-Propanetricarboxylic acid, 2-hydroxy- (9CI); Z56754862; Citric acid (monohydrate): H2O = 1 g : 1 ml solution; Citric acid, certified reference material, TraceCERT(R); Citric acid, meets USP testing specifications, anhydrous; F2191-0222; 8F5D336A-442D-434A-9FB0-E400FF74E343; Citrate standard for IC, 1000 mg/L, analytical standard; 1,2,3-PROPANETRICARBOXYLIC ACID,2-HYDROXY (CITRIC ACID); Citric acid, United States Pharmacopeia (USP) Reference Standard; Citric acid, anhydrous, cell culture tested, plant cell culture tested; Citric acid, anhydrous, European Pharmacopoeia (EP) Reference Standard; Citric acid, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99.5%; Citric acid, Anhydrous, Pharmaceutical Secondary Standard; Certified Reference Material; Citric acid, meets analytical specification of Ph. Eur., BP, USP, E330, anhydrous, 99.5-100.5% (based on anhydrous substance)
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  Formula C6H8O7
  Weight 192.12
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
  InChI Key KRKNYBCHXYNGOX-UHFFFAOYSA-N
  Isomeric SMILES C(C(=O)O)C(CC(=O)O)(C(=O)O)O
  Canonical SMILES C(C(=O)O)C(CC(=O)O)(C(=O)O)O
  External Links PubChem ID 311
CAS ID 77-92-9
HIT ID C1246
CHEMBL ID CHEMBL1261
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Brassica juncea (var. RLC-1)
  Factor Name: CdCl2 Treatment; Earthworms Treatment [1]
              Species Info Factor Info
               Experiment Detail
The experiments were conducted under controlled conditions using plastic pots having lower diameter of 7.8 cm, upper diameter of 13.5 cm and 12 cm in height. The soil was collected from the top layer (0-20 cm) from the Botanical Garden of the university. Soil was air dried crushed and sieved through 2 mm filter autoclaved at 121 ℃ for 2 h. The soil was autoclaved to exclude soil pathogens and other microorganisms if any. The autoclaved soil was poured in pots and kept in the growth chamber. The pots were filled with 500 g uncontaminated soil and partially decayed compost (cow manure) (2:1) and was used as growing medium. The cow dung was added into the soil for better performance of earthworms. A subsample of the study soil before mixing with compost was analyzed for its physicochemical characteristics. The soil used for the experiment was sandy loam soil having pH 7.8 , EC (Electrical conductivity) (µS/cm) =184.25 , TDS (Total Dissolved Solids) (mg/kg) = 130 , N (Nitrogen) (mg/kg) = 103 , P (Phosphorus) (mg/kg) = 10.6 , K (Potassium) (mg/kg) = 0.343 , %OC = 0.894, Cd (mg/kg) = ND (not detected by AAS).The Cd treatment was given by using anhydrous CdCl2 (Minimum assay: 95.0%) procured from Hi-Media laboratories. The CdCl2 anhydrous was added to the soil to make different concentrations of Cd 0.50 mM, 0.75 mM, 1.00 mM, and 1.25 mM (i.e. 56 mg/Kg , 84 mg/Kg , 112 mg/Kg and 140 mg/Kg respectively). The various treatments given are as shown below:(1)C0 (Control): (Cadmium absence);(2)C1: (0.5 mM Cd);(3)C2: (0.75 mM Cd);(4)C3: (1.00 mM Cd);(5)C4: (1.25 mM Cd).Each Cd treatment was given in soils without as well as with earthworms (WTE = without, WE = with earthworms). Earthworms (3 earthworms per pot) were inoculated after seven days of Cd treatment and incubated for 7 d in soil with earthworms. The seeds after surface sterilization were sown in soil containing different concentration of Cd and earthworms in plastic pots. These pots were kept in seed germinator under controlled conditions i.e. 25 ℃ temperature and 16:8 h dark: light photoperiod (1700 lx) for 15 d. Seedlings were harvested after 15 d followed by washing with distilled water. The growth and biochemical analysis was done on these seedlings.
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               Factor Function
Increased Cd uptake in plants in presence of earthworms enhances the total antioxidative capacity, metal chelating compounds and content of other antioxidants in plants grown under metal polluted soils. Earthworms can improve plant growth by improving nutrient availability to plants through their vermicasting activity. Their role in modifying soil pH and increasing metal phytoavailability made their use ideal in phytoremediation of polluted soils. Increased uptake and accumulation of Cd in plants activates the antioxidative system of plants takes place by addition of earthworms to soil.
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               Mechanism
The gene expression for the key enzymes involved in organic acid metabolism was studied to understand the role of earthworms in organic acid metabolism in plants under Cd metal stress. It was observed that in comparison to control (C0) seedlings the expression of CS, SUCLG1, SDH and FH was enhanced 1.72, 1.58, 1.65 and 1.88 folds in seedlings given C4 treatment with 1.25 mM dose of Cd respectively . However, after supplementation of earthworms to Cd treated soils given C4 treatment resulted in further enhancement in expression of CS (2.53 fold), SUCLG1 (2.35 fold), SDH (2.13 fold) and FH (3.06 fold) .
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               Factor Part Location NP Content
 
0.5 mM CdCl2 + without earthworms
 NA Ludhiana, India.
NP Content: 2.851 ± 0.038 mg/g
 
0.75 mM CdCl2 + without earthworms
 NA Ludhiana, India.
NP Content: 3.144 ± 0.128 mg/g
 
1.00 mM CdCl2 + without earthworms
 NA Ludhiana, India.
NP Content: 4.041 ± 0.145 mg/g
 
1.25 mM CdCl2 + without earthworms
 NA Ludhiana, India.
NP Content: 5.997 ± 0.371 mg/g
 
0 mM CdCl2 + with earthworms
 NA Ludhiana, India.
NP Content: 1.995 ± 0.044 mg/g
 
0 mM CdCl2 + without earthworms
 NA Ludhiana, India.
NP Content: 1.897 ± 0.043 mg/g
 
0.5 mM CdCl2 + with earthworms
 NA Ludhiana, India.
NP Content: 3.146 ± 0.194 mg/g
 
0.75 mM CdCl2 + with earthworms
 NA Ludhiana, India.
NP Content: 3.719 ± 0.129 mg/g
 
1.00 mM CdCl2 + with earthworms
 NA Ludhiana, India.
NP Content: 4.844 ± 0.355 mg/g
 
1.25 mM CdCl2 + with earthworms
 NA Ludhiana, India.
NP Content: 7.469 ± 0.697 mg/g
      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: 311.9 ± 112.6 µg/g dry weight
 
Dry 3-5 days
 Leaves Vienna, Austria
NP Content: 477.6 ± 163.0 µg/g dry weight
 
Dry 6-8 days
 Leaves Vienna, Austria
NP Content: 826.8 ± 249.3 µg/g dry weight
References
1 Role of earthworms in phytoremediation of cadmium (Cd) by modulating the antioxidative potential of Brassica juncea L.
2 Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir)