Citation: Kai ZHAO, Wei JIANG, Chong MENG. Key Parameters Analysis and Regulation of Singlet Oxygen Quenching Rate of Carotenoids[J]. Chinese Journal of Structural Chemistry, ;2020, 39(7): 1226-1234. doi: 10.14102/j.cnki.0254–5861.2011–2568 shu

Key Parameters Analysis and Regulation of Singlet Oxygen Quenching Rate of Carotenoids

Kai ZHAO ^a,, ,
Wei JIANG ^a ,
Chong MENG ^b

a.
Education Academy, Beijing Sport University, Beijing 100084, China
b.
School of Environment, Beijing Normal University, Beijing 100875, China

Corresponding author: Kai ZHAO, zhaokaibeiti@outlook.com
Received Date: 7 August 2019
Accepted Date: 22 November 2019

Figures(2)

28 kinds of carotenoids are studied to reveal the key parameters and regulation on the singlet oxygen quenching rate. First, the quantum chemistry parameters of carotenoids calculated by Gaussian software combined with substitution parameters were used to construct the quantitative structure-activity relationship model (QSAR) of the singlet oxygen quenching rate of carotenoids. The key parameters affecting the antioxidant activity of carotenoids are revealed, and the data predicted via the QSAR model were provided for subsequent research. Then, a three-dimensional (3D) pharmacophore model was used to regulate and modify the antioxidant activity of carotenoids. The correlation coefficients of the modeling group (R²) and verification group (R_pre²) of the established QSAR model were 0.945 and 0.916, respectively, which can be used for the analysis of antioxidant activity of carotenoids; the antioxidant activity of carotenoids can be significantly regulated by the number of conjugated C=C bonds, the energy difference between frontier molecular orbitals and the partial Mulliken charge in C1 and the π…π^* excitation energy E(s); the antioxidant activity of carotenoids can be effectively regulated by the hydrogen bond acceptor pharmacophores on both sides of the conjugated C=C bonds and the hydrophobic groups on the conjugated C=C bond; the hydrophobic substituents attached to conjugated C=C bonds can effectively improve the singlet oxygen quenching rate of carotenoids.
- carotenoids,
- singlet oxygen quenching,
- quantitative structure-activity relationship model,
- 3D pharmacophore model,
- parameters analysis
1. [1]
  Yungyuen, W.; Ma, G.; Zhang, L. C.; Yamawaki, K.; Takagi, T.; Kiriiwa, Y.; Ikoma, Y.; Matsumoto, H.; Yoshioka, T.; Nesumi, H. Regulation of carotenoid metabolism in response to different temperatures in citrus juice sacs in vitro. Sci. Hortic. 2017, 238, 384–390.
2. [2]
  Asker, D. High throughput screening and profiling of high-value carotenoids from a wide diversity of bacteria in surface seawater. Food Chem. 2018, 261, 103–111. doi: 10.1016/j.foodchem.2018.03.109
3. [3]
  Benmeziane, A.; Boulekbache-Makhlouf, L.; Mapelli-Brahm, P.; Khodja, N. K.; Remini, H.; Madani, K.; Meléndez-Martínez, A. J. Extraction of carotenoids from cantaloupe waste and determination of its mineral composition. Food Res. Int. 2018, 111, 391–398. doi: 10.1016/j.foodres.2018.05.044
4. [4]
  Zeng, Y. C.; Mu, G. P.; Huang, S. F.; Zeng, X. H.; Cheng, H.; Li, Z. X. Effects of lycopene on number and function of human peripheral blood endothelial progenitor cells cultivated with high glucose. Nutr. Res. Pract. 2014, 8, 368–376. doi: 10.4162/nrp.2014.8.4.368
5. [5]
  Rao, A. V.; Rao, L. G. Carotenoids and human health. Pharmacol. Res. 2007, 55, 207–216. doi: 10.1016/j.phrs.2007.01.012
6. [6]
  Kamath, B. S.; Srikanta, B. M.; Dharmesh, S. M.; Sarada, R.; Ravishankar, G. A. Ulcer preventive and antioxidative properties of astaxanthin from Haematococcus pluvialis. Eur. J. Pharmacol. 2008, 590, 387–395. doi: 10.1016/j.ejphar.2008.06.042
7. [7]
  Islam, S. N.; Nusrat, T.; Begum, P.; Ahsan, M. Carotenoids and β-carotene in orange fleshed sweet potato: a possible solution to vitamin A deficiency. Food Chem. 2016, 199, 628–631. doi: 10.1016/j.foodchem.2015.12.057
8. [8]
  De Lucca, L.; Rodrigues, F.; Jantsch, L. B.; Kober, H.; Neme, W. S.; Gallarreta, F. M. P.; Gonçalves, T. L. Delta-aminolevulinate dehydratase activity and oxidative stress markers in preeclampsia. Biomed. Pharmacother. 2016, 84, 224–229. doi: 10.1016/j.biopha.2016.09.033
9. [9]
  Yang, Z. H.; Luo, S.; Wei, Z. S.; Ye, T.; Spinney, R.; Chen, D.; Xiao, R. Rate constants of hydroxyl radical oxidation of polychlorinated biphenyls in the gas phase: a single-descriptor based QSAR and DFT study. Environ. Pollut. 2016, 211, 157–164. doi: 10.1016/j.envpol.2015.12.044
10. [10]
  Amir, M.; Khan, A.; Mujeeb, M. Phytochemical analysis and in vitro antioxidant activity of zingiber officinale. Free Radical. Antioxi. 2011, 1, 75–81. doi: 10.5530/ax.2011.4.12
11. [11]
  Foote, D. S.; Denny, R. W. Chemistry of singlet oxygen. Ⅶ. Quenching by. beta. -carotene. J. Am. Chem. Soc. 1968, 90, 6233–6235. doi: 10.1021/ja01024a061
12. [12]
  Baltschun, D.; Beutner, S.; Briviba, K.; Martin, H. D.; Paust, J.; Peters, M.; Röver, S.; Sies, H.; Stahl, W.; Steigel, A.; Stenhorst, F. Singlet oxygen quenching abilities of carotenoids. Eur. J. Org. Chem. 1997, 9, 1887–1893.
13. [13]
  Heymann, T.; Heinz, P.; Glomb, M. A. Lycopene inhibits the isomerization of β-carotene during quenching of singlet oxygen and free radicals. J. Agr. Food Chem. 2015, 63, 3279–3287 doi: 10.1021/acs.jafc.5b00377
14. [14]
  Fukuzawa, K.; Inokami, Y.; Tokumura, A.; Terao, J.; Suzuki, A. Rate constants for quenching singlet oxygen and activities for inhibiting lipid peroxidation of carotenoids and α-tocopherol in liposomes. Lipids. 1998, 33, 751–756. doi: 10.1007/s11745-998-0266-y
15. [15]
  Singh, A. K. Development of quantitative structure-activity relationship (QSAR) models for predicting risk of exposure from carcinogens in animals. Cancer Invest. 2001, 19, 611–620. doi: 10.1081/CNV-100104289
16. [16]
  Chen, K. X.; Shen, Q. Q.; Shen, S. Y.; Zhou, X. T.; Li, Z. G.; Chen, Z. X. In-silico prediction of the sweetness of aspartame analogues from QSPR analysis. Chin. J. Struct. Chem. 2018, 37, 1689–1702.
17. [17]
  Jin, H.; Hua, S. G.; Feng, M. B.; Chen, L. QSAR modeling of toxicity of quaternary ammonium compounds to Chlorella pyrenoidosa using 2D and 3D descriptors. Chin. J. Struct. Chem. 2015, 34, 1793–1802.
18. [18]
  Sun, Y. J.; Wu, D.; Liu, D. H. Quantitative structure-activity relationship studies on the antioxidant activity and gap junctional communication of carotenoids. Chin. J. Struct. Chem. 2010, 29, 1362–1372.
19. [19]
  Soffers, A. E.; Marjon, J. H.; Haandel, V. Antioxidant activities of carotenoids: quantitative relationships between theoretical calculations and experimental literature data. Free Radical Res. 1990, 30, 233–240.
20. [20]
  Sun, Y. J.; Pang, J.; Ye, X. Q.; Lv, Y.; Li, J. Quantitative structure-activity relationship study on the antioxidant activity of carotenoids. Chin. J. Struct. Chem. 2009, 28, 163–170.
21. [21]
  Woodall, A. A.; Ming Lee, S. W.; Weesie, R. J.; Jackson, M. J. Oxidation of carotenoids by free radicals: relationship between structure and reactivity. BBA-Gen. Subjects 1997, 1336, 33–42. doi: 10.1016/S0304-4165(97)00006-8
22. [22]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian Inc., Pittsburgh PA 2009, Gaussian 09, Revision A. 02.
23. [23]
  Hohenberg, P.; Kohn, W. Inhomogeneous electron gas. Phys. Rev. 1964, 136, B864–B871. doi: 10.1103/PhysRev.136.B864
24. [24]
  Zhu, H.; Wang, M. C. A semi-stationary copula model approach for bivariate survival data with interval sampling. Int. J. Biostat. 2015, 11, 151–173.
25. [25]
  Jiang, L.; Li, Y. How do the substituents affect and regulate the relative retention times of polychlorinated biphenyls during gas chromatography? J. Chemometr. 2015, 29, 606–614. doi: 10.1002/cem.2744
26. [26]
  Tropsha, A.; Gramatica, P.; Gombar, V. K. The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models. Qsar Comb. Sci. 2003, 22, 69–77. doi: 10.1002/qsar.200390007
27. [27]
  Ojha, P. K.; Mitra, I.; Das, R. N.; Roy, K. Further exploring r_m² metrics for validation of QSPR models. Chemom. Intell. Lab. Syst. 2011, 107, 194–205. doi: 10.1016/j.chemolab.2011.03.011
28. [28]
  Arkan, E.; Shahlaei, M.; Pourhossein, A.; Fakhri, K.; Fassihi, A. Validated QSAR analysis of some diaryl substituted pyrazoles as CCR2 inhibitors by various linear and nonlinear multivariate chemometrics methods. Eur. J. Med. Chem. 2010, 45, 394–406.
29. [29]
  Huang, H. J.; Lee, C. C.; Chen, C. Y. C. Pharmacological chaperone design for reducing risk factor of Parkinson's disease from traditional Chinese medicine. E. Evid. Based Complement Alternat Med. 2014, 2014, 830490–830490.
30. [30]
  Conn, P. F.; Schalch, W.; Truscott, T. G. The singlet oxygen and carotenoid interaction. J. Photoch. Photobio. B 1991, 11, 41–47. doi: 10.1016/1011-1344(91)80266-K
31. [31]
  Devasagayam, T. P. A.; Sundquist, A. R.; Di Mascio, P.; Kaiser S.; Sies H. Activity of thiols as singlet molecular oxygen quenchers. J. Photochem. Photobiol. B 1991, 9, 105–116. doi: 10.1016/1011-1344(91)80008-6
32. [32]
  Truscott, T. G. The photophysics and photochemistry of the carotenoids. J. Photochem. Photobiol. B: Biol. 1990, 6, 359–371. doi: 10.1016/1011-1344(90)85110-I
33. [33]
  Krisky, N. I. Carotenoid protection against oxidation. Pure Allp. Chem. 1979, 51, 649–660. doi: 10.1351/pac197951030649
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