General Information of Natural Product (ID: NP0912)
  Natural Product Name
Neoxanthin
  Synonyms
9'-cis-Neoxanthin; Neoxanthin; cis-Neoxanthin; 14660-91-4; UNII-KK8M5T48AI; KK8M5T48AI; 9-cis-Neoxanthin; Foliaxanthin; Trolliflor; (3S,5R,6R,3'S,5'R,6'S)-9'-cis-6,7-didehydro-5,6,5',6'-tetrahydro-5',6'-epoxy-beta,beta-carotene-3,5,3'-triol; Neoxanthine; (3S,3'S,5R,5'R,6R,6'S,8R,9'cis)-6,7-didehydro-5,5',6,6'-tetrahydro-5',6'-epoxy-beta,beta-carotene-3,3',5-triol; Trollixanthin; CCRIS 7560; 9c-neoxanthin; 9cNeox; CHEBI:35306; HY-N7523; LMPR01070291; CS-0131634; FD876F35-DAB5-457B-8E95-04A3DD3BEBB6; Q27104309; 6,7-Didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-b,b-carotene-3,3',5-triol; (3S,3'S,5R,5'R,6S,6'S,9'Z)-6,7-Didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3',5-triol; (3S,5R,6R,3'S,5'R,6'S)-5',6'-EPOXY-6,7-DIDEHYDRO- 5,6,5',6'-TETRAHYDRO-BETA,BETA-CAROTENE-3,5,3'-TRIOL; 9'-CIS-NEOXANTHIN; beta,beta-Carotene, 6,7-didehydro-5',6'-epoxy-5,5',6,6'-tetrahydro-3,3',5-trihydroxy-, (3S,3'S,5R,5'R,6R,6'S,9'-cis)-
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  Formula C40H56O4
  Weight 600.9
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI InChI=1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20-/t22?,33-,34-,38+,39+,40-/m0/s1
  InChI Key PGYAYSRVSAJXTE-FTLOKQSXSA-N
  Isomeric SMILES C/C(=C\\C=C\\C=C(/C)\\C=C\\C=C(/C)\\C=C=C1[C@](C[C@H](CC1(C)C)O)(C)O)/C=C/C=C(/C)\\C=C\\[C@]23[C@](O2)(C[C@H](CC3(C)C)O)C
  Canonical SMILES CC(=CC=CC=C(C)C=CC=C(C)C=C=C1C(CC(CC1(C)O)O)(C)C)C=CC=C(C)C=CC23C(CC(CC2(O3)C)O)(C)C
  External Links PubChem ID 5282217
CAS ID 14660-91-4

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Brassica oleracea L., var. italica, cv. Waltham 29
  Factor Name: Methyl Jasmonate Treatment; UV Radiation Treatment [1]
              Species Info Factor Info
               Experiment Detail
Briefly, broccoli seeds (0.5 g per replication) were sanitized for 15 min in sodium hypochlorite (1.5%, v/v), rinsed with Milli-Q water and soaked with aeration overnight in darkness and at room temperature. After pouring off the soaking water, the seeds were spread evenly on standard 200 square cell plug trays (21.38 × 11.05 × 1.75) containing Canadian Sphagnum peat moss previously moistened. Sprouts were grown in a culture room with controlled temperature (25 ℃ ) and a photoperiod regime with cycles of 16 h light and 8 h darkness. Water (control) or a phytohormone solution were atomized every 12 h throughout the experiment.Six trays with broccoli sprouts seeds were prepared for this study, and were assigned for (A) Control (no UV or phytohormone application), (B) UVA treatment, (C) UVB treatment, (D) MJ treatment, (E) UVA + MJ treatment, and (F) UVB + MJ treatment.MJ treatments (D, E and F) were conducted based on Perez-Balibrea et al. with slight adjustments. Briefly, methyl jasmonate (MJ) was dissolved in 0.2% ethanol to obtain a 25 µM solution and applied every 12 h by exogenous spraying 65 mL of 25 µM MJ solution from sowing day until the end of the experiment (8th day after sowing). Due to the volatility of MJ and to avoid the fact that treatment to one tray may result in application to neighboring trays, the MJ solution was applied using physical separation. Control sprouts (A) and sprouts treated with UVA or UVB alone (B and C) were irrigated with the same frequency using 65 mL of Milli-Q water containing 0.04% ethanol.On the 7th day after sowing, UV (B and C) and UV + MJ (E and F) treatments were carried out in special UVA and UVB chambers based on Moreira-Rodriguez et al. with slight adjustments. Chambers used for treatments B and E were equipped with two 40 W UVA lamps (Sylvania F40W T12 BL350, Ledvance LLC., Wilmington, MA, USA), while chambers for treatments C and F consisted of two 40 W UVB lamps (Philips TL 40W/12 RS, Philips, Ljubljana, Slovenia). Trays with broccoli sprouts were placed 30 cm below the irradiation source. All UV treatments consisted of a single exposure for 120 min. The irradiation intensities were determined prior to the experiment as 9.47 and 7.16 W/m2 for UVA and UVB, respectively, using a PMA 2200 radiometer equipped with PMA 2110 UVA and PMA 2106 UVB sensors (Solar Light, Glenside, PA, USA) measuring in the spectral range from 320-400 nm and 280-320 nm, respectively.After UV treatments, trays were returned to culture room and the proper irrigation with water or MJ solution continued for an additional (acclimatization) period of 24 h. Sprouts of all six trays were harvested at the 8th day after sowing, immediately flash-frozen in liquid nitrogen, placed at -80 ℃ , freeze-dried (Labconco, Kansas City, MO, USA), and then ground to a fine powder. Samples were stored at -80 ℃ until further analysis.
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               Factor Function
Simple pre-harvest treatments such as UV radiation, applied alone or in combination with exogenous MJ, can be used as an effective emerging technology that allows the accumulation of specific phytochemicals in broccoli sprouts. Furthermore, results demonstrated that the profile of glucosinolates accumulated in stressed broccoli sprouts could be tailored towards the over-production of most indole glucosinolates by applying 25 µM MJ alone or preferably in combination with a 120 min exposure to UVA or UVB radiation (9.47 and 7.16 W/m2, respectively) 24 h prior harvest. Specifically, a synergistic effect in the accumulation of NGBS was achieved by combining UV and MJ stresses. On the other hand, the production of aliphatic or specific indole glucosinolates can be triggered by UVB supplementation alone. MJ treatments may be applied if an increase in gallic acid, its derivative GAH II, specific sinapic acid derivatives (e.g., 5-SQA) and ferulic acid derivatives (e.g., 1,2-diFG) is desired. However, such increases would be at the expense of the following compounds: GAH I, GTA, diGH, 3-O-H-K, 1-O-S-beta-d-g, sinapoyl malate, sinapic acid, K-3-O-S-so-7-O-g, 1,2-diSG, 1-S-2-FG, the majoritarian isomer of 1,2,2-triSG and 1,2-diS-1-FG; as they were significantly reduced after treatments with MJ. Application of UVA alone may be recommended to accumulate GAH I, 1-O-S-beta-d-g, sinapic acid, gallic acid, K-3-O-S-so-7-O-g, 1-S-2-FG and the second isomer of 1,2,2-triSG. Finally, a single 120 min exposure to UVA radiation should be applied to increase xanthophyll and chlorophyll content in broccoli sprouts.
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               Factor Part Location NP Content
 
25 µ Methyl Jasmonate
Sprouts NA
NP Content: 68.5 ± 5.1 mg/kg dry weight
 
Control (no UV or phytohormone application)
Sprouts NA
NP Content: 116.7 ± 7.5 mg/kg dry weight
 
UVA treatment (Irradiation intensities: 9.47 W/m2)
Sprouts NA
NP Content: 155.8 ± 10.2 mg/kg dry weight
 
UVB treatment (Irradiation intensities: 7.16 W/m2)
Sprouts NA
NP Content: 159.5 ± 6.8 mg/kg dry weight
 
UVA + 25 µ Methyl Jasmonate
Sprouts NA
NP Content: 69.2 ± 1.6 mg/kg dry weight
 
UVB + 25 µ Methyl Jasmonate
Sprouts NA
NP Content: 58.6 ± 0.6 mg/kg dry weight
      Species Name: Rubus idaeus
  Factor Name: Cultivar Comparison; Organic Fertilization; Traditional Fertilization [2]
              Species Info Factor Info
               Experiment Detail
The experiment was carried out in 2013. Leaves of five raspberry cultivars ('Polana', 'Polka', 'Tulameen', 'Laszka' and 'Glen Ample') were collected at the time of cultivation. Three organic and neighborhood conventional farms were used for experimental purposes. From one cultivar (one field plot), 3-4 plants were chosen, which were analyzed separately. One sample consisted of 10 leaves. The farm was treated as a replication. [organic farm no. 1 Localization: akroczym(52° 26″ N 20° 36″ E), Type of Soil: sandy middle soil IVa and IVb category (15% floatable particles) pH 5.5, Kind of Fertilizer: cow manure, Dose of Fertilizers and Time of Given: 35 t/ha one year before raspberry planting, Plant Protection System: Grevit 200 SL; organic farm no. 2 Localization: Zaluski (52° 37″ N 20° 22″ E), Type of Soil: sandy middle soil, sandy-clay IV category (20% floatable particles), pH 5.5, Kind of Fertilizer:cow manure, Dose of Fertilizers and Time of Given: 30 t/ha one year before raspberry planting, Plant Protection System: no protection; organic farm no. 3 Localization: Radzanow(51° 33″ N 20° 51″ E), Type of Soil: sandy middle soil IVa and III category (10% floatable particles), pH 6.0, Kind of Fertilizer:sheep manure, green manure, Dose of Fertilizers and Time of Given: 10 t/ha and 15 t/ha one year before raspberry planting, Plant Protection System: Bioczos 33 SL, Grevit 200 SL; conventional farm no. 1 Localization: Czerwinsk nad Wisla (52° 23″ N 20° 20″ E), Type of Soil: sandy-loamy middle soil IV and III category (20% floatable particles), pH 5.5, Kind of Fertilizer: Hydrocomplex 12-11-18; Superba 8-11-36, Dose of Fertilizers and Time of Given: (200 kg/ha, 150 kg/ha) in autumn a year before raspberry planting; 3 doses in time of cultivation, Plant Protection System: Signum 33 WG, Miros 20 SP; conventional farm no. 2 Localization: Czerwinsk nad Wisla (52° 23″ N 20° 20″ E), Type of Soil: sandy-loamy middle soil IV and III category (25% floatable particles), pH 5.5, Kind of Fertilizer: amonium nitrate, polyphosphate, magnesium sulphate, Dose of Fertilizers and Time of Given: in autumn a year before raspberry planting; 3 doses in time of cultivation, Plant Protection System: Calypso 480 SC, Miros 20 SP, Zato 50 WG; conventional farm no. 3 Localization: Czerwinsk nad Wisla(52° 25″ N 20° 23″ E), Type of Soil: sandy-clay middle soil II and III category (20% floatable particles) pH 6.0, Kind of Fertilizer:Rosafert 5-12-24-3, Dose of Fertilizers and Time of Given: 250 kg/ha in autumn a year before raspberry planting; 4 doses in time of cultivation, Plant Protection System: Calypso 480 SC, Miros 20 SP, Zato 50 WG].
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               Factor Function
Compared with conventional raspberry leaves, organic raspberry leaves were characterized by a significantly higher content of dry matter, total polyphenols, total phenolic acids, chlorogenic acid, caffeic acid, salicylic acid and quercetin-3-O-rutinoside; moreover, the organic leaves were characterized by higher antioxidant activity. Among examined cultivars, 'Polka' c. was characterized by the highest antioxidant status. However, raspberry leaves from conventional farms contained more total carotenoids, violaxanthin, alpha-carotene, beta-carotene, total chlorophyll and individual forms of chlorophylls: a and b.
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               Factor Part Location NP Content
 
Cultivation System: organic farm
Leaves Poland
NP Content: 0.045 ± 0.01 mg/100g fresh weight
 
Cultivation System: conventional farm
Leaves Poland
NP Content: 0.025 ± 0.00 mg/100g fresh weight
 
Rubus idaeus cv. Polana
Leaves Poland
NP Content: 0.033 ± 0.00 mg/100g fresh weight
 
Rubus idaeus cv. Polka
Leaves Poland
NP Content: 0.024 ± 0.00 mg/100g fresh weight
 
Rubus idaeus cv. Tulameen
Leaves Poland
NP Content: 0.037 ± 0.01 mg/100g fresh weight
 
Rubus idaeus cv. Laszka
Leaves Poland
NP Content: 0.062 ± 0.01 mg/100g fresh weight
 
Rubus idaeus cv. Glen Ample
Leaves Poland
NP Content: 0.021 ± 0.00 mg/100g fresh weight
References
1 UVA, UVB Light, and Methyl Jasmonate, Alone or Combined, Redirect the Biosynthesis of Glucosinolates, Phenolics, Carotenoids, and Chlorophylls in Broccoli Sprouts
2 Phenolics and Carotenoid Contents in the Leaves of Different Organic and Conventional Raspberry ( Rubus idaeus L. ) Cultivars and Their In Vitro Activity