Photoprotective Properties of Natural Pulvinic Acid Derivatives toward Ultraviolet-Induced Damages

Abstract

Pulvinic acid derivatives are considered as worthy to be evaluated as skin protection factor toward ultraviolet-induced damages because of their colors and locations in lichens. Due to the lack of literature about photo-protective features of pulvinic acid derivatives, their cosmetic potentials for skin protection were evaluated in silico, for the first time. Computational chemistry, biology and pharmacology platforms such as Gaussian, GAMESS, PASS, PaDEL-DDPredictor and VEGA QSAR platforms were employed to determine the activities of pulvinic acid derivatives. Pulvinic acid derivatives were divided into three groups as the most promising, promising and unpromising compounds according to the calculated p-values. Although leprapinic acid, demethylleprapinic acid, pinastric acid, leprapinic acid methyl ether, 4-hydroxyvulpinic acid and vulpinic acid were determined as the most promising compounds, epanorin and rhizocarpic acid were identified as promising compounds. The proposed model seems to be reliable because the calculated p-value for vulpinic acid was found to be compatible with previously obtained experimental results. The pulvinic acid derivatives that were identified as the most promising ones should be therefore further studied by in vitro and in vivo multiple experiments.

Keywords

• Lichen
• Ultraviolet
• Photoprotective
• Pulvinic Acid
• p-value

References

1. Stocker-Wörgötter, E., Biochemical Diversity and Ecology of Lichen-Forming Fungi: Lichen Substances, Chemosyndromic Variation and Origin of Polyketide-Type Metabolites (Biosynthetic Pathways), in Recent Advances in Lichenology. 2015, Springer. p. 161-179.
2. Mosbach, K., Biosynthesis of lichen substances, products of a symbiotic association. Angewandte Chemie International Edition, 1969. 8(4): p. 240-250.
3. Varol, M., et al., Photoprotective Activity of Vulpinic and Gyrophoric Acids Toward Ultraviolet B‐Induced Damage in Human Keratinocytes. Phytotherapy research, 2016. 30(1): p. 9-15.
4. Chen, J., H.-P. Blume, and L. Beyer, Weathering of rocks induced by lichen colonization—a review. Catena, 2000. 39(2): p. 121-146.
5. Nguyen, K.-H., et al., UV-protectant metabolites from lichens and their symbiotic partners. Natural product reports, 2013. 30(12): p. 1490-1508.
6. Paudel, B., et al., Antioxidant, antibacterial activity and brine shrimp toxicity test of some mountainous lichens from Nepal. Biological research, 2012. 45(4): p. 387-391.
7. Kumar, J., et al., Antioxidant capacities, phenolic profile and cytotoxic effects of saxicolous lichens from trans-Himalayan cold desert of Ladakh. PloS one, 2014. 9(6): p. e98696.
8. Elix, J.A. and E. Stocker-Wörgötter, Biochemistry and secondary metabolites, in Lichen Biology, I.I.I.T.H. Nash, Editor. 2008, Cambridge University Press: Cambridge. p. 104-133.

9. Rubio, C., et al., Effects of solar UV-B radiation in the accumulation of rhizocarpic acid in a lichen species from alpine zones of Chile. Boletín de la Sociedad Chilena de Química, 2002. 47(1): p. 67-72.
10. Hidalgo, M., et al., Photophysical, photochemical, and thermodynamic properties of shikimic acid derivatives: calycin and rhizocarpic acid (lichens). Journal of Photochemistry and Photobiology B: Biology, 2002. 66(3): p. 213-217.
11. Rouvray, D.H., The evolution of the concept of molecular similarity, in Concepts and applications of molecular similarity, M.A. Johnson and G.M. Maggiora, Editors. 1990, Wıley: New York. p. 15-42.
12. Warr, W.A., Some Trends in Chem (o) informatics, in Chemoinformatics and Computational Chemical Biology, J. Bajorath, Editor. 2011, Humana Press: Germany. p. 1-37.
13. Peltason, L. and J. Bajorath, Computational analysis of activity and selectivity cliffs, in Chemoinformatics and Computational Chemical Biology, J. Bajorath, Editor. 2011, Humana Press: Germany. p. 119-132.
14. Rashidi, H.H. and L.K. Buehler, Bioinformatics basics: applications in biological science and medicine. 1999: CRC press.
15. Shukla, V., G.P. Joshi, and M. Rawat, Lichens as a potential natural source of bioactive compounds: a review. Phytochemistry Reviews, 2010. 9(2): p. 303-314.
16. Shrestha, G. and L.L.S. Clair, Lichens: a promising source of antibiotic and anticancer drugs. Phytochemistry reviews, 2013. 12(1): p. 229-244.
17. Lohézic-Le Dévéhat, F., et al., Lichenic extracts and metabolites as UV filters. Journal of Photochemistry and Photobiology B: Biology, 2013. 120: p. 17-28.
18. Huneck, S. and I. Yoshimura, Identification of lichen substances, in Identification of lichen substances. 1996, Springer. p. 11-123.
19. Maalouf, S., et al., Protective effect of vitamin E on ultraviolet B light–induced damage in keratinocytes. Molecular carcinogenesis, 2002. 34(3): p. 121-130.
20. Goel, R.K., et al., PASS-assisted exploration of new therapeutic potential of natural products. Medicinal Chemistry Research, 2011. 20(9): p. 1509-1514.
21. He, Y., et al., PaDEL‐DDPredictor: Open‐source software for PD‐PK‐T prediction. Journal of computational chemistry, 2013. 34(7): p. 604-610.
22. Mathew, S., et al., In silico studies of medicinal compounds against hepatitis C capsid protein from north India. Bioinformatics and Biology insights, 2014. 8: p. 159.
23. Varol, M., et al., Evaluation of the sunscreen lichen substances usnic acid and atranorin. Biocell, 2015. 39(1): p. 25-31.
24. Harvey, A.L., Natural products in drug discovery. Drug discovery today, 2008. 13(19): p. 894-901.
25. Dimitrova, V., M. Kaneva, and T. Gallucci, Customer knowledge management in the natural cosmetics industry. Industrial Management & Data Systems, 2009. 109(9): p. 1155-1165.
26. Chang, Y.H., Consumer and Formulator of Natural Cosmetics: Understanding and Integrating Each Other's Needs. Formulating, Packaging, and Marketing of Natural Cosmetic Products, 2011: p. 15-26.
27. Koehn, F.E. and G.T. Carter, The evolving role of natural products in drug discovery. Nature reviews. Drug discovery, 2005. 4(3): p. 206.
28. Molnár, K. and E. Farkas, Current results on biological activities of lichen secondary metabolites: a review. Zeitschrift für Naturforschung C, 2010. 65(3-4): p. 157-173.
29. Boustie, J. and M. Grube, Lichens—a promising source of bioactive secondary metabolites. Plant Genetic Resources, 2005. 3(2): p. 273-287.
30. Ranković, B. and M. Kosanić, Lichens as a potential source of bioactive secondary metabolites, in Lichen Secondary Metabolites. 2015, Springer. p. 1-26.
31. Thevanayagam, H., S.M. Mohamed, and W.-L. Chu, Assessment of UVB-photoprotective and antioxidative activities of carrageenan in keratinocytes. Journal of applied phycology, 2014. 26(4): p. 1813-1821.
32. Kokubun, T., W.K.P. Shiu, and S. Gibbons, Inhibitory activities of lichen-derived compounds against methicillin-and multidrug-resistant Staphylococcus aureus. Planta medica, 2007. 73(02): p. 176-179.
33. Fernández-Moriano, C., et al., Neuroprotective activity and cytotoxic potential of two Parmeliaceae lichens: Identification of active compounds. Phytomedicine, 2015. 22(9): p. 847-855.
34. Legouin, B., et al., Specialized Metabolites of the Lichen Vulpicida pinastri Act as Photoprotective Agents. Molecules, 2017. 22(7): p. 1162.