Stilbenes: A new strategy for protecting light-sensitive foods, a review of their structure classification and singlet oxygen quenching mechanism

References

• Aminah, N. S., S. A. Achmad, N. Aimi, E. L. Ghisalberti, E. H. Hakim, M. Kitajima, Y. M. Syah, and H. Takayama. 2002. Diptoindonesin A, a new C-glucoside of ε-viniferin from Shorea seminis (Dipterocarpaceae). Fitoterapia 73 (6):501–7. doi: 10.1016/S0367-326X(02)00179-X.
   PubMed Web of Science ®Google Scholar
• Arnold, S. J., M. Kubo, and E. A. Ogryzlo. 1968. Relaxation and reactivity of singlet oxygen. In Advances in chemistry series, ed. R. J. Mayo, vol. 77, 133–42. Washington, DC: American Chemical Society. doi: 10.1021/ba-1968-0077.ch070.
   Google Scholar
• Arraki, K., É. Renouf, P. Waffo-Téguo, J.-M. Mérillon, T. Richard, and A. Decendit. 2017. Identification and quantification of stilbenes in some Tunisian red wines using UPLC-MS and HPLC-DAD. OENO One 51 (2): 231–236. doi: 10.29199/PSEP.101016.
   Google Scholar
• Baderschneider, B., and P. Winterhalter. 2000. Isolation and characterization of novel stilbene derivatives from Riesling wine. Journal of Agricultural and Food Chemistry 48 (7):2681–6. doi: 10.1021/jf991348k.
   PubMed Web of Science ®Google Scholar
• Balasundram, N., K. Sundram, and S. Samman. 2006. Phenolic compounds in plants and agri-industrial by-products: Antioxidant activity, occurrence, and potential uses. Food Chemistry 99 (1):191–203. doi: 10.1016/j.foodchem.2005.07.042.
   Web of Science ®Google Scholar
• Bassarello, C., B. Giuseppe, M. Paola, S. Alexandre, K. Ether, P. Cosimo, and P. Sonia. 2007. Gloriosaols A and B, two novel phenolics from Yucca gloriosa: Structural characterization and configurational assignment by a combined NMR-quantum mechanical strategy. Tetrahedron 63 (1):148–54. doi: 10.1016/j.tet.2006.10.034.
   Web of Science ®Google Scholar
• Błaszczyk, A., S. Sady, and M. Sielicka. 2019. The stilbene profile in edible berries. Phytochemistry Reviews 18 (1):37–67. doi: 10.1007/s11101-018-9580-2.
   Web of Science ®Google Scholar
• Boulos, R. A., Y. T. Nikki, A. L. Nigel, A. H. Katherine, F. F. Niki, A. Natalie, W. S. Brian, Y. W. Pan, M. Boris, V. R. Thomas, et al. 2013. Inspiration from old dyes: Tris(stilbene) compounds as potent gram-positive antibacterial agents. Chemistry Europe Journal 19 (52):17980–8. doi: 10.1002/chem.201303119.
   PubMed Web of Science ®Google Scholar
• Casadey, R., C. Challier, A. Senz, and S. Criado. 2019. Antioxidant ability of tyrosol and derivative-compounds in the presence of O2 (1Δg)-species. Studies of synergistic antioxidant effect with commercial antioxidants. Food Chemistry 285:275–81. doi: 10.1016/j.foodchem.2019.01.161.
   PubMed Web of Science ®Google Scholar
• Cayuela, J. A., A. Vazquez, A. G. Perez, and J. M. Garcia. 2009. Control of table grapes postharvest decay by ozone treatment and resveratrol induction. Food Science and Technology International 15 (5):495–502. doi: 10.1177/1082013209350539.
   Web of Science ®Google Scholar
• Celaje, J. A., D. Zhang, A. M. Guerrero, and M. Selke. 2011. Chemistry of trans-resveratrol with singlet oxygen: 2 + 2 addition, 4 + 2 addition, and formation of the phytoalexin moracin M. Organic Letters 13 (18):4846–9. doi: 10.1021/ol201922u.
   PubMed Web of Science ®Google Scholar
• Chalal, M., A. Klinguer, A. Echairi, P. Meunier, D. Vervandier-Fasseur, and M. Adrian. 2014. Antimicrobial activity of resveratrol analogues. Molecules (Basel, Switzerland) 19 (6):7679–88. doi: 10.3390/molecules19067679.
   PubMed Web of Science ®Google Scholar
• Cheng, H., M. A. Khan, Z. F. Xie, S. N. Tao, Y. X. Li, and L. Liang. 2020. A peppermint oil emulsion stabilized by resveratrol-zein-pectin complex particles: Enhancing the chemical stability and antimicrobial activity in combination with the synergistic effect. Food Hydrocolloids 103:105675. doi: 10.1016/j.foodhyd.2020.105675.
   Web of Science ®Google Scholar
• Chen, J., R. F. Gonzalez-Laredo, and J. J. Karchesy. 2000. Minor diarylheptanoid glycosides of Alnus rubra bark. Phytochemistry 53 (8):971–3. doi: 10.1016/S0031-9422(99)00523-3.
   PubMed Web of Science ®Google Scholar
• Chen, J. J., S. He, H. Mao, C. R. Sun, and Y. J. Pan. 2009. Characterization of polyphenol compounds from the roots and stems of Parthenocissus laetevirens by high-performance liquid chromatography/tandem mass spectrometry. Rapid Communications in Mass Spectrometry: RCM 23 (6):737–44. doi: 10.1002/rcm.3937.
   PubMed Web of Science ®Google Scholar
• Choe, E., and D. B. Min. 2006. Chemistry and reactions of reactive oxygen species in foods. Critical Reviews in Food Science and Nutrition 46 (1):1–22. doi: 10.1080/10408390500455474.
   PubMed Web of Science ®Google Scholar
• Choi, Y. S., and M. Y. Jung. 2016. Kinetic study on the singlet oxygen quenching activity of nordihydroguaiaretic acid (NDGA) using methylene blue sensitized photooxidation of alpha-terpinene. Food Science and Biotechnology 25 (5):1333–6. doi: 10.1007/s10068-016-0209-1.
   PubMed Web of Science ®Google Scholar
• Chong, J., A. Poutaraud, and P. Hugueney. 2009. Metabolism and roles of stilbenes in plants. Plant Science 177 (3):143–55. doi: 10.1016/j.plantsci.2009.05.012.
   Web of Science ®Google Scholar
• Delaunois, B., S. Cordelier, A. Conreux, C. Clement, and P. Jeandet. 2009. Molecular engineering of resveratrol in plants. Plant Biotechnology Journal 7 (1):2–12. doi: 10.1111/j.1467-7652.2008.00377.x.
   PubMed Web of Science ®Google Scholar
• Deng, S. L., W. F. Chen, B. Zhou, L. Yang, and Z. L. Liu. 2006. Protective effects of curcumin and its analogues against free radical-induced oxidative haemolysis of human red blood cells. Food Chemistry 98 (1):112–9. doi: 10.1016/j.foodchem.2005.05.063.
   Web of Science ®Google Scholar
• DeRosa, M. C., and R. J. Crutchley. 2002. Photosensitized singlet oxygen and its applications. Coordination Chemistry Reviews 233–234:351–71. doi: 10.1016/S0010-8545(02)00034-6.
   Web of Science ®Google Scholar
• Di Mascio, P., G. R. Martinez, S. Miyamoto, G. E. Ronsein, M. H. G. Medeiros, and J. Cadet. 2016. Singlet molecular oxygen: Düsseldorf - São Paulo, the Brazilian connection. Archives of Biochemistry and Biophysics 595:161–75. doi: 10.1016/j.abb.2015.11.016.
   PubMed Web of Science ®Google Scholar
• Dusek, J., J. Skoda, O. Holas, A. Horvatova, T. Smutny, L. Linhartova, P. Hirsova, O. Kucera, S. Micuda, A. Braeuning, et al. 2019. Stilbene compound trans -3,4,5,4’-tetramethoxystilbene, a potential anticancer drug, regulates constitutive androstane receptor (Car) target genes, but does not possess proliferative activity in mouse liver. Toxicology Letters 313:1–10. doi: 10.1016/j.toxlet.2019.05.024.
   PubMed Web of Science ®Google Scholar
• El Khawand, T., A. Courtois, J. Valls, T. Richard, and S. Krisa. 2018. A review of dietary stilbenes: Sources and bioavailability. Phytochemistry Reviews 17 (5):1007–29. doi: 10.1007/s11101-018-9578-9.
   Web of Science ®Google Scholar
• Fang, J. G., M. Lu, Z. H. Chen, H. H. Zhu, Y. Li, L. Yang, L. M. Wu, and Z. L. Liu. 2002. Antioxidant effects of resveratrol and its analogues against the free-radical-induced peroxidation of linoleic acid in micelles. Chemistry - A European Journal 8 (18):4191–8. doi: 10.1002/1521-3765(20020916)8:18 < 4191::AID-CHEM4191 > 3.0.CO;2-S.
   PubMed Web of Science ®Google Scholar
• Federica, M., G. Giuseppe, C. Massimo, O. Sara, G. Paolo, and C. M. Maria. 2015. Effect of substituted stilbenes on platelet function. Fitoterapia 105:228–33. doi: 10.1016/j.fitote.2015.07.009.
   PubMed Web of Science ®Google Scholar
• Filomena, S., F. Ana, G. Eugenia, N. Cristina, and C. D. Fernanda. 2014. Strategies to improve the solubility and stability of stilbene antioxidants: A comparative study between cyclodextrins and bile acids. Food Chemistry 145:115–25. doi: 10.1016/j.foodchem.2013.08.034.
   PubMed Web of Science ®Google Scholar
• Frelin, O., C. Dervinis, J. L. Wegrzyn, J. M. Davis, and A. D. Hanson. 2017. Drought stress in Pinus taeda L. induces coordinated transcript accumulation of genes involved in the homogentisate pathway. Tree Genetics & Genomes 13 (1):1–10. doi: 10.1007/s11295-017-1115-2.
   Web of Science ®Google Scholar
• Gabaston, J., J. V. Fonayet, C. Franc, P. Waffo-Teguo, G. de Revel, G. Hilbert, E. Gomes, T. Richard, and J. M. Merillon. 2020. Characterization of stilbene composition in grape berries from wild vitis species in year-to-year harvest. Journal of Agricultural and Food Chemistry 68 (47):13408–17. doi: 10.1021/acs.jafc.0c04907.
   PubMed Web of Science ®Google Scholar
• Gomes, M. D., M. D. Cardoso, A. C. G. Guimaraes, A. C. Guerreiro, C. M. L. Gago, E. V. D. V. Boas, C. M. B. Dias, A. C. C. Manhita, M. L. Faleiro, M. G. C. Miguel, et al. 2017. Effect of edible coatings with essential oils on the quality of red raspberries over shelf-life. Journal of the Science of Food and Agriculture 97 (3):929–38. doi: 10.1002/jsfa.7817.
   PubMed Web of Science ®Google Scholar
• He, S., L. Y. Jiang, B. Wu, Y. J. Pan, and C. R. Sun. 2009. Pallidol, a resveratrol dimer from red wine, is a selective singlet oxygen quencher. Biochemical and Biophysical Research Communications 379 (2):283–7. doi: 10.1016/j.bbrc.2008.12.039.
   PubMed Web of Science ®Google Scholar
• He, S., L. Jiang, B. Wu, J. Zhou, and Y.-J. Pan. 2009. Two novel antioxidative stilbene tetramers from Parthenocissus laetevirens. Helvetica Chimica Acta 92 (7):1260–7. doi: 10.1002/hlca.200800371.
   Web of Science ®Google Scholar
• He, S., Y. B. Lu, L. Y. Jiang, B. Wu, F. Y. Zhang, and Y. J. Pan. 2009. Preparative isolation and purification of antioxidative stilbene oligomers from Vitis chunganeniss using high-speed counter-current chromatography in stepwise elution mode. Journal of Separation Science 32 (14):2339–45. doi: 10.1002/jssc.200900033.
   PubMed Web of Science ®Google Scholar
• He, S., Y. B. Lu, B. Wu, and Y. J. Pan. 2007. Isolation and purification of antioxidative isomeric polyphenols from the roots of Parthenocissus laetevirens by counter-current chromatography. Journal of Chromatography. A 1151 (1–2):175–9. doi: 10.1016/j.chroma.2007.02.102.
   PubMed Web of Science ®Google Scholar
• He, S., B. Wu, Y. J. Pan, and L. Y. Jiang. 2008. Stilbene oligomers from Parthenocissus laetevirens: Isolation, biomimetic synthesis, absolute configuration, and implication of antioxidative defense system in the plant. The Journal of Organic Chemistry 73 (14):5233–41. doi: 10.1021/jo8001112.
   PubMed Web of Science ®Google Scholar
• Huang, K. S., M. Lin, and Y. H. Wang. 1999. Synthesis of amurensin H, a new resveratrol dimer from the roots of Vitis Amurensisi. Chinese Chemical Letters 10:817–20.
   Web of Science ®Google Scholar
• Huang, K. S., R. L. Li, Y. H. Wang, and M. Lin. 2001. Three new stilbene trimers from the lianas of Gnetum hainanense. Planta Medica 67 (1):61–4. doi: 10.1055/s-2001-10875.
   PubMed Web of Science ®Google Scholar
• Huang, Y. L., W. J. Tsai, C. C. Shen, and C. C. Chen. 2005. Resveratrol derivatives from the roots of Vitis thunbergii. Journal of Natural Products 68 (2):217–20. doi: 10.1021/np049686p.
   PubMed Web of Science ®Google Scholar
• Hurst, J. R., J. D. McDonald, and G. B. Schuster. 1982. Lifetime of singlet oxygen in solution directly determined by laser spectroscopy. Journal of the American Chemical Society 104 (7):2065–7. doi: 10.1021/ja00371a065.
   Web of Science ®Google Scholar
• Ilseung, Y., K. Eunha, K. Junhee, H. Hyouksoo, S. Soohwan, B. P. Seung, and S. K. Kim. 2012. Photochemical generation of a new, highly fluorescent compound from non-fluorescent resveratrol. Chemical Communications (Cambridge, England) 48 (32):3839–41. doi: 10.1039/c2cc30940h.
   PubMed Web of Science ®Google Scholar
• Ioset, J. R., A. Marston, M. P. Gupta, and K. Hostettmann. 2001. Five new prenylated stilbenes from the root bark of Lonchocarpus chiricanus. Journal of Natural Products 64 (6):710–5. doi: 10.1021/np000597w.
   PubMed Web of Science ®Google Scholar
• Jiang, L. Y., S. He, K. Z. Jiang, C. R. Sun, and Y. J. Pan. 2010. Resveratrol and its oligomers from wine grapes are selective (1)O2 quenchers: Mechanistic implication by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry and theoretical calculation. Journal of Agricultural and Food Chemistry 58 (16):9020–7. doi: 10.1021/jf102005z.
   PubMed Web of Science ®Google Scholar
• Jung, M. Y., S. H. Yoon, H. O. Lee, and D. B. Min. 1998. Singlet oxygen and ascorbic acid effects on dimethyl disulfide and off‐flavor in skim milk exposed to light. Journal of Food Science 63 (3):408–12. doi: 10.1111/j.1365-2621.1998.tb15753.x.
   Web of Science ®Google Scholar
• Kim, J. Y., D. S. Choi, and M. Y. Jung. 2003. Anti photo-oxidative activity of sesamol in methylene blue- and chlorophyll-sensitized photo-oxidation of oil. Journal of Agricultural and Food Chemistry 51 (11):3460–5. doi: 10.1021/jf026056p.
   PubMed Web of Science ®Google Scholar
• Kong, Q. J., X. Y. Ren, R. L. Hu, X. F. Yin, G. S. Jiang, and Y. J. Pan. 2016. Isolation and purification of two antioxidant isomers of resveratrol dimer from the wine grape by counter-current chromatography. Journal of Separation Science 39 (12):2374–9. doi: 10.1002/jssc.201600004.
   PubMed Web of Science ®Google Scholar
• Kong, Q. J., X. Y. Ren, L. Y. Jiang, Y. J. Pan, and C. R. Sun. 2010. Scirpusin A, a hydroxystilbene dimer from Xinjiang wine grape, acts as an effective singlet oxygen quencher and DNA damage protector. Journal of the Science of Food and Agriculture 90 (5):823–8. doi: 10.1002/jsfa.3890.
   PubMed Web of Science ®Google Scholar
• Kong, Q. J., X. Y. Ren, L. D. Tu, X. D. Zheng, Z. D. Wang, and Y. J. Pan. 2016. The mechanism of action of pterostilbene in Xinjiang wine grape against the growth of Geotrichum citri-aurantii. Food Biotechnology 30 (3):173–88. doi: 10.1080/08905436.2016.1198705.
   Web of Science ®Google Scholar
• Kong, Q. J., R. R. Rongrong Deng, X. Y. Li, Q. Z. Qingzhi Zeng, X. Zhang, X. Yu, and X. Y. Ren. 2020. Based on RNA-Seq analysis identification and expression analysis of trans-scripusin A synthesize-related genes of UV-treatment in postharvest grape fruit. Archives of Biochemistry and Biophysics 690:108471. doi: 10.1016/j.abb.2020.108471.
   PubMed Web of Science ®Google Scholar
• Kong, Q. J., X. F. Yin, J. Yu, and X. Y. Ren. 2018. Mechanistic processes of resveratrol in inhibiting the oxidative damage of guanine, as evidenced by UHPLC-MS2. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 1093–1094:174–82. doi: 10.1016/j.jchromb.2018.07.007.
   PubMed Web of Science ®Google Scholar
• Krishnan, S., A. Arjunan, S. Sellaiyan, R. Perumalsamy, S. Sambasivam, and V. Babu. 2005. Electron momentum distribution mapping of trans-stilbene single crystal bypositron annihilation. Chemical Physics Letters 412:327–30. doi: 10.1016/j.cplett.2005.07.017.
   Web of Science ®Google Scholar
• Langcake, P., C. A. Cornford, and R. J. Pryce. 1979. Identification of pterostilbene as a phytoalexin from Vitis vinifera leaves. Phytochemistry 18 (6):1025–7. doi: 10.1016/S0031-9422(00)91470-5.
   Web of Science ®Google Scholar
• Langcake, P., and R. J. Pryce. 1977. The production of resveratrol and the viniferins by grapevines in response to ultraviolet irradiation. Phytochemistry 16 (8):1193–6. doi: 10.1016/S0031-9422(00)94358-9.
   Web of Science ®Google Scholar
• Lee, Y., and E. Choe. 2011. Interaction of phosphatidylcholine and α-tocopherol on the oxidation of sunflower oil and content changes of phosphatidylcholine and tocopherol in the emulsion under singlet oxygen. Journal of Food Science 76 (3):C498–503. doi: 10.1111/j.1750-3841.2011.02096.x.
   PubMed Web of Science ®Google Scholar
• Likhitwitayawuid, K., and B. Sritularak. 2001. A new dimeric stilbene with tyrosinase inhibitiory activity from Artocarpus gomezianus. Journal of Natural Products 64 (11):1457–9. doi: 10.1021/np0101806.
   PubMed Web of Science ®Google Scholar
• Li, N., X. M. Li, K. S. H, and M. L. 2001. Structure and distribution of resveratrol oligomer analogs. Acta Pharmaceutica Sinica 36 (12):944–50. doi: 10.16438/j.0513-4870.2001.12.017.
   Google Scholar
• Li, Y. H., J. Lu, X. L. Tian, Z. Xu, L. X. Huang, H. X. Xiao, X. Y. Ren, and Q. J. Kong. 2021. Alginate with citrus pectin and pterostilbene as healthy food packaging with antioxidant property. International Journal of Biological Macromolecules 193 (Pt B):2093–102. doi: 10.1016/J.IJBIOMAC.2021.11.041.
   PubMedGoogle Scholar
• Li, C., J. Lu, X. Xu, R. Hu, and Y. Pan. 2012. pH-switched HRP-catalyzed dimerization of resveratrol: A selective biomimetic synthesis. Green Chemistry 14 (12):3281–4. doi: 10.1039/c2gc36288k.
   Web of Science ®Google Scholar
• Lins, A. P., J. D. Felicio, M.  M. Braggio, and L. C. Roque. 1991. A resveratrol   dimer from Parthenocissus tricuspidata. Phytochemistry 30 (9):3144–6. doi: 10.1016/S0031-9422(97)00898-4
   Web of Science ®Google Scholar
• Li, X., B. Wu, L. Wang, and S. Li. 2006. Extractable amounts of trans-resveratrol in seed and berry skin in Vitis evaluated at the germplasm level. Journal of Agricultural and Food Chemistry 54 (23):8804–11. doi: 10.1021/jf061722y.
   PubMed Web of Science ®Google Scholar
• Li, C., X. F. Xu, Z. H. Tao, C. R. Sun, and Y. J. Pan. 2016. Resveratrol derivatives: An updated patent review (2012-2015). Expert Opinion on Therapeutic Patents 26 (10):1189–200. doi: 10.1080/13543776.2016.1215435.
   PubMed Web of Science ®Google Scholar
• Li, C., X. Xu, Z. Tao, X. J. Wang, and Y. Pan. 2015. Resveratrol dimers, nutritional components in grape wine, are selective ROS scavengers and weak Nrf2 activators. Food Chemistry 173:218–23. doi: 10.1016/j.foodchem.2014.09.165.
   PubMed Web of Science ®Google Scholar
• Lledias, F., and W. Hansberg. 2000. Catalase modification as a marker for singlet oxygen. Methods in Enzymology 319:110–9. doi: 10.1016/S0076-6879(00)19013-5.
   PubMed Web of Science ®Google Scholar
• Loschke, D. C., L. A. Hadwiger, and W. Wagoner. 1983. Comparison of mRNA populations coding for phenylalanine ammonia lyase and other peptides from pea tissue treated with biotic and abiotic inducers. Physiological Plant Pathology 23 (1):163–73. doi: 10.1016/0048-4059(83)90043-7.
   Google Scholar
• Mahendran, R., R. K. Ramanan, J. B. Francisco, M. L. Jose, L. F. Olalla, E. S. M. Paulo, R. Shahin, S. S. Anderson, and K. T. Brijesh. 2019. Recent advances in the application of pulsed light processing for improving food safety and increasing shelf life. Trends in Food Science & Technology 88:67–79. doi: 10.1016/j.tifs.2019.03.010.
   Web of Science ®Google Scholar
• Manussanunt, C., C. Taksina, S. Boonchoo, and L. Kittisak. 2011. Oxyresveratrol protects against DNA damage induced by photosensitized riboflavin. Natural Product Communications 6 (1):41–4. doi: 10.1177/1934578X1100600110.
   PubMed Web of Science ®Google Scholar
• Manzocco, L., G. Kravina, S. Calligaris, and M. C. Nicoli. 2008. Shelf life modeling of photosensitive food: The case of colored beverages. Journal of Agricultural and Food Chemistry 56 (13):5158–64. doi: 10.1021/jf800072u.
   PubMed Web of Science ®Google Scholar
• Mazzone, G., M. E. Alberto, N. Russo, and E. Sicilia. 2014. Ab initio calculations on the (1)O2 quenching mechanism by trans-resveratrol. Physical Chemistry Chemical Physics: PCCP 16 (25):12773–81. doi: 10.1039/c4cp00754a.
   PubMed Web of Science ®Google Scholar
• Medrano-Padial, C., A. I. Prieto, M. Puerto, and S. Pichardo. 2021. Toxicological evaluation of piceatannol, pterostilbene, and ε-viniferin for their potential use in the food industry: A review. Foods 10 (3):592. doi: 10.3390/foods10030592.
   PubMed Web of Science ®Google Scholar
• Meng, X., J. Zhou, C. N. Zhao, R. Y. Gan, and H. B. Li. 2020. Health benefits and molecular mechanisms of resveratrol: A narrative review. Foods 9 (3):340. doi: 10.3390/foods9030340.
   PubMed Web of Science ®Google Scholar
• Min, D. B., and J. M. Boff. 2002. Chemistry and reaction of singlet oxygen in foods. Comprehensive Reviews in Food Science and Food Safety 1 (2):58–72. doi: 10.1111/j.1541-4337.2002.tb00007.x.
   PubMedGoogle Scholar
• Morikawa, T., F. M. Xu, H. Matsuda, and M. Yoshikawa. 2010. Structures of novel norstilbene dimer, longusone A, and three new stilbene dimers, longusols A, B, and C, with antiallergic and radical scavenging activities from Egyptian natural medicine Cyperus longus. Chemical & Pharmaceutical Bulletin 58 (10):1379–85. doi: 10.1248/cpb.58.1379.
   PubMed Web of Science ®Google Scholar
• Murata, H., I. Iliya, T. Tanaka, M. Furasawa, T. Ito, K. Nakaya, M. Oyama, and M. Iinuma. 2005. Four new trimeric stilbene glucosides from Welwitschia mirabilis. Chemistry & Biodiversity 2 (6):773–9. doi: 10.1002/cbdv.200590054.
   PubMed Web of Science ®Google Scholar
• Ohyam, M., T. Tanaka, and M. Iinuma. 1995. Five resveratrol oligomers from roots of Sophora leachiana. Phytochemistry 38 (3):733–40. doi: 10.1016/0031-9422(95)00692-3.
   Web of Science ®Google Scholar
• Oshima, Y., Y. Ueno, K. Hisamichi, and M. Takeshita. 2010. Ampelopsins F and G, novel bridged plant oligostilbenes from Ampelopsis brevipedunculata var. hancei Roots (Vitaceae). ChemInform 24 (43): 5801–5804. doi: 10.1002/chin.199343257.
   Google Scholar
• Ouchi, A., K. Aizawa, Y. Iwasaki, T. Inakuma, J. Terao, S-i Nagaoka, and K. Mukai. 2010. Kinetic study of the quenching reaction of singlet oxygen by carotenoids and food extracts in solution. Development of a singlet oxygen absorption capacity (SOAC) assay method. Journal of Agricultural and Food Chemistry 58 (18):9967–78. doi: 10.1021/jf101947.
   PubMed Web of Science ®Google Scholar
• Petit, A. N., F. Baillieul, N. Vaillant-Gaveau, L. Jacquens, A. Conreux, P. Jeandet, C. Clement, and F. Fontaine. 2009. Low responsiveness of grapevine flowers and berries at fruit set to UV-C irradiation. Journal of Experimental Botany 60 (4):1155–62. doi: 10.1093/jxb/ern361.
   PubMed Web of Science ®Google Scholar
• Pezet, R., K. Gindro, O. Viret, and H. Richter. 2004. Effect of resveratrol, viniferins and pterostilbene on Plasmopara viticola zoospore mobility and disease development. Vitis 43 (3):145–8. doi: 10.1007/s00122-003-1443-5.
   Web of Science ®Google Scholar
• Puntumchai, A., P. Kittakoop, S. Rajviroongit, S. Vimuttipong, K. Likhitwitayawuid, and Y. Thebtaranonth. 2004. Lakoochins A and B, new antimycobacterial stilbene derivatives from Artocarpus lakoocha. Journal of Natural Products 67 (3):485–6. doi: 10.1021/np030429e.
   PubMed Web of Science ®Google Scholar
• Ramu, G. A., M. Kannan, R. D. Karthick, A. A. Pillay, M. Shanmugam, P. Sathishkumar, J. Johansen, and B. K. Tiwari. 2022. Phycoerythrin: A pink pigment from red sources (rhodophyta) for a greener biorefining approach to food applications. Critical Reviews in Food Science and Nutrition Jun 1:1–19. doi: 10.1080/10408398.2022.2081962.
   Google Scholar
• Ren, X. Y., P. P. An, X. Zhai, S. Wang, and Q. J. Kong. 2019. The antibacterial mechanism of pterostilbene derived from xinjiang wine grape: A novel apoptosis inducer in Staphyloccocus aureus and Escherichia coli. LWT 101:100–6. doi: 10.1016/j.lwt.2018.11.038.
   Web of Science ®Google Scholar
• Rivière, C., A. D. Pawlus, and J. M. Mérillon. 2012. Natural stilbenoids: Distribution in the plant kingdom and chemotaxonomic interest in Vitaceae. Natural Product Reports 29 (11):1317–33. doi: 10.1039/c2np2oo49j.
   PubMed Web of Science ®Google Scholar
• Rodriguez, R. A., I. R. Lahoz, O. N. Faza, M. M. Cid, and C. S. Lopez. 2012. Theoretical and experimental exploration of the photochemistry of resveratrol: Beyond the simple double bond isomerization. Organic & Biomolecular Chemistry 10 (46):9175–82. doi: 10.1039/c2ob26241j.
   PubMed Web of Science ®Google Scholar
• Sasi, K. S., and R. Sanghi. 2001. Analyzing pesticide residues in winter vegetables from Kanpur. Indian Journal of Environmental Health 43 (4):154–8.
   PubMedGoogle Scholar
• Shan, Z., H. W. Ying, and S. Gnetubainin. 2002. A new resveratrol dimer from Gnetum hainanense. Chinese Chemical Letters 13 (6):549–50.
   Web of Science ®Google Scholar
• Shen, T., X. N. Wang, and H. X. Lou. 2009. Natural stilbenes: An overview. Natural Product Reports 26 (7):916–35. doi: 10.1039/B905960A.
   PubMed Web of Science ®Google Scholar
• Shen, J., Q. Zhou, P. Li, Z. Q. Wang, S. S. Liu, C. N. He, C. H. Zhang, and P. G. Xiao. 2017. Update on phytochemistry and pharmacology of naturally occurring resveratrol oligomers. Molecules 22 (12):2050. doi: 10.3390/molecules22122050.
   PubMed Web of Science ®Google Scholar
• Silva, G. S., M. Judith, R. N. M. Rita, M. T. S. Adrián, M. Cristina, C. L. Moisés, and L. F. Joaquim. 2013. Photochemical and photocatalytic degradation of trans-resveratrol. Photochemical & Photobiological Sciences. Official Journal of the European Photochemistry Association and the European Society for Photobiology 12 (4):638–44. doi: 10.1039/c2pp25239b.
   PubMed Web of Science ®Google Scholar
• Siqueira, F. C. D., T. C. L. D. D. Socorro, A. Z. Mercadnte, R. C. Chiste, and A. S. Lopes. 2019. Profile of phenolic compounds and carotenoids of Arrabidaea chica leaves and the in vitro singlet oxygen quenching capacity of their hydrophilic extract. Food Research International 126 (C):108597. doi: 10.1016/j.foodres.2019.108597.
   PubMedGoogle Scholar
• Sobolev, V. S., S. A. Neff, and J. B. Gloer. 2010. New dimeric stilbenoids from fungal-challenged peanut (Arachis hypogaea) seeds. Journal of Agricultural and Food Chemistry 58 (2):875–81. doi: 10.1021/jf903410e.
   PubMed Web of Science ®Google Scholar
• Sotheeswaran, S., and V. Pasupathy. 1993. Distribution of resveratrol oligomers in plants. Phytochemistry 32 (5):1083–92. doi: 10.1016/S0031-9422(00)95070-2.
   Web of Science ®Google Scholar
• Sotheeswaran, S., M. U. Sultanbawa, S. Surendrakumar, and P. Bladon. 1983. ChemInform Abstract: Polyphenols from dipterocarp species. Copalliferol A and stemonoporol. Chemischer Informationsdienst 14 (30): 699–702. doi: 10.1002/chin.198330364.
   Google Scholar
• Sueishi, Y., R. Nii, and N. Kakizaki. 2017. Resveratrol analogues like piceatannol are potent antioxidants as quantitatively demonstrated through the high scavenging ability against reactive oxygen species and methyl radical. Bioorganic & Medicinal Chemistry Letters 27 (23):5203–6. doi: 10.1016/j.bmcl.2017.10.045.
   PubMed Web of Science ®Google Scholar
• Syah, Y. M., S. A. Achmad, E. L. Ghisalberti, E. H. Hakim, M. Z. N. Iman, L. Makmur, and D. Mujahiddin. 2000. Andalasin A, a new stilbene dimer from Morus macroura. Fitoterapia 71 (6):630–5. doi: 10.1016/S0367-326X(00)00221-5.
   PubMed Web of Science ®Google Scholar
• Takaoka, M. 1940. The synthesis of resveratrol and its derivatives. Proceedings of the Imperial Academy 16 (8):405–7. doi: 10.2183/pjab1912.16.405.
   Google Scholar
• Tanaka, T., I. Iliya, T. Ito, M. Furusawa, K. I. Nakaya, M. Iinuma, Y. Shirataki, N. Matsuura, M. Ubukata, J. Murata, et al. 2001. Stilbenoids in lianas of Gnetum parvifolium. Chemical & Pharmaceutical Bulletin 49 (7):858–62. doi: 10.1248/cpb.49.858. 11456092
   PubMed Web of Science ®Google Scholar
• Tanaka, T., M. Iinuma, and H. Murata. 1998. Stilbene derivatives in the stem of parthenocissus quinquefolia. Phytochemistry 48 (6):1045–9. doi: 10.1016/S0031-9422(98)00071-5.
   Web of Science ®Google Scholar
• Tanaka, T., M. Ohyama, K. Morimoto, F. Asai, and M. Iinuma. 1998. A resveratrol dimer from Parthenocissus tricuspidata. Phytochemistry 48 (7):1241–3. doi: 10.1016/S0031-9422(97)00898-4.
   Web of Science ®Google Scholar
• Thomas, V. 2010. Phenylpropanoid biosynthesis. Molecular Plant 3 (1):2–20. doi: 10.1093/mp/ssp106.
   PubMed Web of Science ®Google Scholar
• Timperio, A. M., A. D’Alessandro, M. Fagioni, P. Magro, and L. Zolla. 2012. Production of the phytoalexins trans-resveratrol and delta -vinif/erin in two economy-relevant grape cultivars upon infection with Botrytis cinerea in field conditions. Plant Physiology and Biochemistry: PPB 50 (1):65–71. doi: 10.1016/j.plaphy.2011.07.008.
   PubMedGoogle Scholar
• Toni, E. K., V. F. Josep, D. C. Grégory, H. O. Ruth, J. Michael, F. Céline, R. Gilles, D. Alain, K. Stéphanie, and R. Tristan. 2020. Resveratrol transformation in red wine after heat treatment. Food Research International 132 (C):109068. doi: 10.1016/j.foodres.2020.109068.
   PubMedGoogle Scholar
• Vhangani, L. N, and J. Van Wyk. 2016. Antioxidant activity of Maillard reaction products (MRPs) in a lipid-rich model system. Food Chemistry 208:301–8. doi: 10.1016/j.foodchem.2016.03.100. 27132854
   PubMed Web of Science ®Google Scholar
• Vuong, T. V., C. Franco, and W. Zhang. 2014. Treatment strategies for high resveratrol induction in Vitis vinifera L. cell suspension culture. Biotechnology Reports 1-2 (C):15–21. doi: 10.1016/j.btre.2014.04.002.
   Google Scholar
• Wan, X., X. B. Wang, M. H. Yang, J. S. Wang, and L. Y. Kong. 2011. Dimerization of piceatannol by Momordica charantia peroxidase and alpha-glucosidase inhibitory activity of the biotransformation products. Bioorganic & Medicinal Chemistry 19 (17):5085–92. doi: 10.1016/j.bmc.2011.07.032.
   PubMed Web of Science ®Google Scholar
• Wu, S. X., R. G. Xiong, S. Y. Huang, D. D. Zhou, A. Saimaiti, C. N. Zhao, A. Shang, Y. J. Zhang, R. Y. Gan, and H. B. Li. 2022. Effects and mechanisms of resveratrol for prevention and management of cancers: An updated review. Critical Reviews in Food Science and Nutrition Jul 19:1–19. doi: 10.1080/10408398.2022.2101428.
   Google Scholar
• Xiang, T., T. Uno, F. Ogino, C. Q. Ai, J. Duo, and U. Sankawa. 2005. Antioxidant constituents of Caragana tibetica. Chemical & Pharmaceutical Bulletin 53 (9):1204–6. doi: 10.1248/cpb.53.1204.
   PubMed Web of Science ®Google Scholar
• Xiao, K., H. J. Zhang, L. J. Xuan, J. Zhang, Y. M. Xu, and D. L. Bai. 2008. Stilbenoids: Chemistry and bioactivities. Studies in Natural Products Chemistry 34:453–646. doi: 10.1016/S1572-5995(08)80032-4.
   Google Scholar
• Xu, X. J., X. Y. Hu, S. J. Neill, J. Y. Fang, and W. M. Cai. 2005. Fungal elicitor induces singlet oxygen generation, ethylene release and saponin synthesis in cultured cells of Panax ginseng C. A. Meyer. Plant & Cell Physiology 46 (6):947–54. doi: 10.1093/pcpl/pci103.
   PubMed Web of Science ®Google Scholar
• Yin, X. F., J. Yu, Q. J. Kong, and X. Y. Ren. 2017. Mechanism of isomers and analogues of resveratrol dimers selectively quenching singlet oxygen by UHPLC-ESI-MS2. Food Chemistry 237:1101–11. doi: 10.1016/j.foodchem.2017.06.021.
   PubMed Web of Science ®Google Scholar
• Yoshikawa, M., T. Morikawa, F. Xu, and H. Matsuda. 2002. Structures and Radical Scavenging Activities of Novel Norstilbene Dimer, Longusone A, and New Stilbene Dimers, Longusols A, B, and C, from Egyptian Herbal Medicine Cyperus longus. HETEROCYCLES 57 (11):1983 10.3987/COM-02-9596.
   Web of Science ®Google Scholar
• Yu, J., J. Qi, L. Zhang, X. Yu, Q. J. Kong, and X. Y. Ren. 2018. Using the relative abundance of characteristic product ions in UHPLC-ESIQTOF-MS2 methods to identify isomers of resveratrol oligomers in extracts of Xinjiang winegrape stems. Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 1096:88–94. doi: 10.1016/j.jchromb.2018.08.022.
   PubMed Web of Science ®Google Scholar
• Zhao, Y., M. Shi, J. H. Ye, X. Q. Zheng, J. L. Lu, and Y. R. Liang. 2015. Photo-induced chemical reaction of trans-resveratrol. Food Chemistry 171:137–43. doi: 10.1016/j.foodchem.2014.08.130.
   PubMed Web of Science ®Google Scholar