General Information of Natural Product (ID: NP0879)
  Natural Product Name
5,7-Dihydroxy-2-(4-Hydroxyphenyl)Chroman-4-One
  Synonyms
naringenin; 67604-48-2; 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; (+/-)-Naringenin; 4',5,7-Trihydroxyflavanone; 480-41-1; naringetol; salipurpol; Naringenine; 93602-28-9; (-)-Naringenin; NARIGENIN; (R,S)-Naringenin; 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one; ( inverted exclamation markA)-Naringenin; 5,7,4'-Trihydroxyflavanone; CHEMBL32571; MLS000028739; MLS000738094; CHEBI:50202; NSC11855; NSC34875; MFCD00006844; SMR000059039; 4',7-Trihydroxyflavanone; 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; Flavanone,5,7-trihydroxy-; Flavanone, 4',5,7-trihydroxy-; NSC-34875; BE-14348A; Narngenn; CCRIS 8135; NSC-11855; 4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-; 4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-; Naringenin (NAR); Prestwick_531; EINECS 266-769-1; Naringenin, 90%; Opera_ID_106; Prestwick0_000466; Prestwick1_000466; Prestwick2_000466; Prestwick3_000466; Oprea1_194140; SCHEMBL20571; BSPBio_000572; MLS001146907; SPBio_002511; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one; BPBio1_000630; MEGxp0_000358; SCHEMBL1934259; ACon1_000582; BDBM19461; GTPL10298; 4',5,7-trihydroxyflavan-4-one; DTXSID50274239; (+/-)-Naringenin, >=95%; HMS1569M14; HMS2096M14; HMS2231O18; HMS3352B08; HMS3373N07; HMS3656G15; Naringenin, natural (US), 98%; BCP31780; MFCD00870553; AKOS015895052; (+/-)-Naringenin, analytical standard; CS-W012357; HY-W011641; KS-5142; MCULE-5489217450; SB17305; (+/-)-Naringenin, ~95% (HPCE); SMP1_000060; NCGC00017346-02; NCGC00017346-03; NCGC00017346-04; NCGC00095963-01; NCGC00095963-02; NCGC00095963-03; AC-20273; K702; SY049933; SY075819; DB-057415; FT-0617135; FT-0630981; FT-0778247; N0072; (R,S)-Naringenin 1000 microg/mL in Acetone; S00279; A867234; 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-one; J-523457; Q-100521; BRD-A94669766-001-02-6; BRD-A94669766-001-04-2; Q57826857; EC19096C-4404-4A16-9BF9-92F9F358E005; ( )-Naringenin; 4?,5,7-Trihydroxyflavanone; H-1-benzopyran-4-one; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one, (S)- #
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  Formula C15H12O5
  Weight 272.25
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2
  InChI Key FTVWIRXFELQLPI-UHFFFAOYSA-N
  Isomeric SMILES C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
  Canonical SMILES C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
  External Links PubChem ID 932
CAS ID 67604-48-2
NPASS ID NPC79943
HIT ID C0808
CHEMBL ID CHEMBL32571
  NP Activity Charts   Click to show/hide

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Chrysanthemum morifolium Ram. cv. 'Gaya yellow'
  Factor Name: Photosynthetic Active Radiation Treatment [1]
              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: 72.2 ± 3.9 mg/kg
 
Under green light (spectral wavelengths: 518 nm)
leaf Korea
NP Content: 90.7 ± 2.7 mg/kg
 
Under red light (spectral wavelengths: 632 nm)
leaf Korea
NP Content: 97.4 ± 5.9 mg/kg
 
Under white light (spectral wavelengths: broad spectrum)
leaf Korea
NP Content: 89.7 ± 0.8 mg/kg
      Species Name: Lentil var. Tina
  Factor Name: H2O2 Treatment; Mannitol Treatment; NaCl Treatment; High Temperature Treatment; Low Temperature Treatment [2]
              Species Info Factor Info
               Experiment Detail
Seeds were sterilized in 1% (v/v) sodium hypochloride (Sigma-Aldrich, USA) for 10 min, then drained and washed with distilled water until they reached neutral pH. They were placed in distilled water and soaked for 6 h at 25 ℃ . Seeds were dark germinated for 8 days in a growth chamber (SANYO MLR-350H) on Petri dishes (125 mm) lined with absorbent paper. Seedlings were watered with 5 ml of Milli-Q water daily. Sprout (8-day-old) samples were gently collected, weighed (fresh mass), rapidly frozen and kept in polyethylene bags at -20 ℃ . For each treatment, three replicates were performed.Elicitation conditions were selected in previous screening studies. For the experiments, temperature (4 ℃ and 40 ℃ - TC and TH, respectively), H2O2 (20 mM and 200 mM - Ox1 and Ox2, respectively), mannitol (200 mM and 600 mM - Os1 and Os2, respectively) and NaCl (100 mM and 300 mM - S-Os1 and S-Os2, respectively) were selected as abiotic elicitors. All solutions were freshly prepared before each application. Mannitol (Os1, Os2), NaCl (S-O1, S-O2) and H2O2 (Ox1) treatments were applied by watering daily (not soaking) 2-day-old sprouts with 5 ml of test solution. For Ox2 (200 mM H2O2) treatment 2-day-old seedlings were only once watered with 5 ml of 200 mM H2O2 and then cultivated under standard conditions. For temperature conditioning treatment, 2-day-old sprouts were incubated at 4 ℃ and 40 ℃ (TC and TH, respectively) for 1 h and then cultivated under standard conditions. Sprout (8-day-old) samples were gently collected, weighed (fresh mass), rapidly frozen and kept in polyethylene bags at -20 ℃ .
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               Factor Function
Application of abiotic elicitors (environmental shocks) was an effective method for improvement of sprout pro-health potential via an increase of phenolic contents and subsequent elevation of antioxidant potential. Innovative application of elicitors on 2-day-old sprouts (not seed) allowed the elimination of the unfavorable influence of the factors employed on germination yield and biomass production. Assuming that the optimal germination conditions are those which most effectively increase the antioxidant potential without any negative influence on biomass accumulation and nutritional quality the elicitation with 20 mM H2O2 for the future applications is recommended.
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               Factor Part Location NP Content
 
Normal condition
Sprouts NA
NP Content: 0.00005 ± 0.0001 mg/g flour
 
Induction with 20 mM H2O2
Sprouts NA
NP Content: 0.00267 ± 0.00062 mg/g flour
 
Induction with 200 mM H2O2
Sprouts NA
NP Content: 0.00174 ± 0.00064 mg/g flour
 
Induction with 200 mM mannitol
Sprouts NA
NP Content: 0.00053 ± 0.00006 mg/g flour
 
Induction with 600 mM mannitol
Sprouts NA
NP Content: 0.00171 ± 0.00017 mg/g flour
 
Induction with 100 mM NaCl
Sprouts NA
NP Content: 0.00023 ± 0.00014 mg/g flour
 
Induction with 300 mM NaCl
Sprouts NA
NP Content: 0.00074 ± 0.00006 mg/g flour
 
Induction at 4 ℃
Sprouts NA
NP Content: 0.00149 ± 0.00003 mg/g flour
 
Induction at 40 ℃
Sprouts NA
NP Content: 0.0006 ± 0.00022 mg/g flour
      Species Name: Streptomyces sp. BT01
  Factor Name: ISP-2 medium [3]
              Species Info Factor Info
               Experiment Detail
Streptomyces sp. BT01 was isolated from the root tissues of Boesenbergia rotunda (L.) Mansf. A spore suspension of Streptomyces sp. BT01 was prepared in distilled water from cultures grown on ISP-4 medium at 30 ℃ for 10 days. The suspension, 108 spores per 100 ml of liquid medium, was added to ISP-2 broth in each 500-ml Erlenmeyer flask. Cultures were kept on a shaker at 120 rpm at 30 ℃ for 48 h and used as seed stocks. For large production of culture filtrates, the strain BT01 was grown in a modified 3000 ml glass container containing 1500 ml of ISP-2 broth, and incubated in an orbital shaker for 5 days in the same condition.
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               Factor Part Location NP Content
 
ISP-2 medium (30℃ + 5 days)
Roots NA
NP Content: 8 mg
      Species Name: Thymus daenensis
  Factor Name: NaCl Treatment [4]
              Species Info Factor Info
               Experiment Detail
The seeds were germinated in seedling plastic tray filled up with a mixture of peat moss and coco peat (1:1). The trays were placed in a glass house at the University of Massachusetts, Amherst, USA, in September 2015. After two weeks, seedlings were transplanted into plastic pots (30 cm diameter and 30 cm height, three seedlings per pot). The pots growth media consisted of 2:1:1 ratio of sieved field soil, sand, and leaf mold, respectively. The medium in each pot was supplemented with 5.8 mg P, 3.3 mg N, and 13.8 mg K to warrant the plant growth; the electrical conductivity was 0.3 mS/cm (Beckman EC meter instrument. cedar grove, New jersey, USA); the pH was 8.04. Plants were maintained at the temperature of 18-25 ℃ ; glass house conditions were set as follows: photoperiod, 16 h; relative humidity, 60-70%; light intensity, 180 µmol m 2 s-1. The source of light was a high pressure sodium lamp in addition to the day light in order to attain 16 h of light per day. Fourty days after planting (establishment period), the uniform sized plants were treated with four different salinity levels including: 0, 30, 60, and 90 mM NaCl. The irrigation with saline solution (250 mL in each pots) was performed every two days . Total amount of NaCl per pot during experiment was 8.75 L. To avoid osmotic shock the salinity treatment started with 15 mM NaCl, and was progressively increased (every two days) to reach the maximum salinity level in each treatment. To prevent water and nutrient leaching, a plastic dish was inserted under each pot and the leached water was given back to pots.
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               Factor Function
Salinity has negative impact on plant production and stimulates several physiological and biochemical modifications in thyme species. Here, a major decline in dry matter, relative water content (RWC), photosynthetic pigment contents, K+, Ca+ as well as increase in Na+ and EL was observed. Our work showed that T. daenensis was similar to T.vulgaris in terms of tolerance to high levels of salinity stress and both species were moderately tolerant to severe salt stress. It should be noted that T. daenensis, as an Iranian endemic species, competes with commercial species like T. vulgaris as a rich source of phenolic compounds. Furthermore, the relative salt tolerance of both species could be related to the exclusion of Na+ from the vascular system in order to protect tissues from salt toxicity and also to the increase of phenolic content and radical scavenging activity. Thus, the plant behavior under salinity stress may be used to boost the production of bioactive compounds to be used on an industrial level for the manufacture of nutraceuticals, functional foods and cosmetics.
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               Factor Part Location NP Content
 
0 mM NaCl
Leaves Isfahan, Iran
NP Content: 1.43 ± 0.17 %
 
30 mM NaCl
Leaves Isfahan, Iran
NP Content: 1.42 ± 0.16 %
 
60 mM NaCl
Leaves Isfahan, Iran
NP Content: 1.72 ± 0.18 %
 
90 mM NaCl
Leaves Isfahan, Iran
NP Content: 1.22 ± 0.03 %
      Species Name: Thymus vulgaris
  Factor Name: NaCl Treatment [4]
              Species Info Factor Info
               Experiment Detail
The seeds were germinated in seedling plastic tray filled up with a mixture of peat moss and coco peat (1:1). The trays were placed in a glass house at the University of Massachusetts, Amherst, USA, in September 2015. After two weeks, seedlings were transplanted into plastic pots (30 cm diameter and 30 cm height, three seedlings per pot). The pots growth media consisted of 2:1:1 ratio of sieved field soil, sand, and leaf mold, respectively. The medium in each pot was supplemented with 5.8 mg P, 3.3 mg N, and 13.8 mg K to warrant the plant growth; the electrical conductivity was 0.3 mS/cm (Beckman EC meter instrument. cedar grove, New jersey, USA); the pH was 8.04. Plants were maintained at the temperature of 18-25 ℃ ; glass house conditions were set as follows: photoperiod, 16 h; relative humidity, 60-70%; light intensity, 180 µmol m 2 s-1. The source of light was a high pressure sodium lamp in addition to the day light in order to attain 16 h of light per day. Fourty days after planting (establishment period), the uniform sized plants were treated with four different salinity levels including: 0, 30, 60, and 90 mM NaCl. The irrigation with saline solution (250 mL in each pots) was performed every two days . Total amount of NaCl per pot during experiment was 8.75 L. To avoid osmotic shock the salinity treatment started with 15 mM NaCl, and was progressively increased (every two days) to reach the maximum salinity level in each treatment. To prevent water and nutrient leaching, a plastic dish was inserted under each pot and the leached water was given back to pots.
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               Factor Function
Salinity has negative impact on plant production and stimulates several physiological and biochemical modifications in thyme species. Here, a major decline in dry matter, relative water content (RWC), photosynthetic pigment contents, K+, Ca+ as well as increase in Na+ and EL was observed. Our work showed that T. daenensis was similar to T.vulgaris in terms of tolerance to high levels of salinity stress and both species were moderately tolerant to severe salt stress. It should be noted that T. daenensis, as an Iranian endemic species, competes with commercial species like T. vulgaris as a rich source of phenolic compounds. Furthermore, the relative salt tolerance of both species could be related to the exclusion of Na+ from the vascular system in order to protect tissues from salt toxicity and also to the increase of phenolic content and radical scavenging activity. Thus, the plant behavior under salinity stress may be used to boost the production of bioactive compounds to be used on an industrial level for the manufacture of nutraceuticals, functional foods and cosmetics.
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               Factor Part Location NP Content
 
0 mM NaCl
Leaves Isfahan, Iran
NP Content: 0.44 ± 0.13 %
 
30 mM NaCl
Leaves Isfahan, Iran
NP Content: 0.49 ± 0.29 %
 
60 mM NaCl
Leaves Isfahan, Iran
NP Content: 0.65 ± 0.21 %
 
90 mM NaCl
Leaves Isfahan, Iran
NP Content: 0.86 ± 0.16 %
References
1 Influences of four different light-emitting diode lights on flowering and polyphenol variations in the leaves of chrysanthemum (Chrysanthemum morifolium)
2 Elicitation with abiotic stresses improves pro-health constituents, antioxidant potential and nutritional quality of lentil sprouts
3 Antibacterial activity of new flavonoids from Streptomyces sp. BT01; an endophyte in boesenbergia rotunda (L.) mansf
4 Effect of salinity stress on the physiological characteristics, phenolic compounds and antioxidant activity of Thymus vulgaris L. and Hyptis marrubioides Celak