Bioactivity test and GC–MS analysis of different solvent extracts from Perilla frutescens (Linn.) Britton and cosmetic product application for sensitive skin
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Published:
Dec 31, 2019
Keywords:
Anti-inflammatory Antioxidant Cosmetic product Skin irritation Stability test
Main Article Content
Abstract
The biological activities of petroleum ether (P), 95% ethanol (E) extracts and hydro-distillation (H) of Perilla frutescens (Linn.) Britton leaves were evaluated. Total phenolic contents, anti-oxidant activity (DPPH• and hydroxyl radical (•OH) scavenging) and the anti-inflammatory effects were determined. The volatile components of the hydro-distillation were determined by GC-MS analysis. The stability of cosmetic products containing the extract and dermal irritancy on human skin were also evaluated. The results suggested that the total phenolic content in E extract was higher than that in P extract. All extracts presented significantly inhibited hydroxyl radical induced deoxyribose degradation with an IC50 value in the range of 0.045±0.017-0.092±0.024 mg/ml more than Trolox (IC50=1.351±0.408 mg/ml). For DPPH assay, E extract showed significantly (p<0.05) higher activity than P extract. The highest ability of inhibition exhibited in E extract was 040E (IC50=0.824±0.061 mg/ml) which is also related to GEAC (3.298±0.237 mg/g extract) and TEAC (13.002±0.933 mg/g extract) values. The anti-inflammatory effects of all E extracts at low concentration 0.0625 ug/g were higher activity to NO inhibition than those of all P extracts. GC-MS analysis showed the presence of 2-Hexanoylfuran and 1-Pentanone in all three samples. The irritation on the volunteer’s skin was not found. To conclude, P. frutescens leaves showed antioxidants activity, serving as an anti-inflammatory agent, and volatile compounds (essential oil) which might be a good plant for cosmeceutical products.
Article Details
How to Cite
1.
Mungmai L, Predalikit W, Aunsri N, Peerakam N. Bioactivity test and GC–MS analysis of different solvent extracts from Perilla frutescens (Linn.) Britton and cosmetic product application for sensitive skin. Prog Appl Sci Tech. [Internet]. 2019 Dec. 31 [cited 2024 Apr. 29];9(2):78-93. Available from: https://ph02.tci-thaijo.org/index.php/past/article/view/242939
Section
Biology and Bioresource technology
References
1. Awah F.M. and Verla A.W. Antioxidant activity, nitric oxide scavenging activity and phenolic contents of Ocimum gratissimum leaf extract. J. Med. Plants Res. 2010. 4(24): 2479–2487.
2. Ramakrishna H., Murthy S.S. and Murthy P.G. Hydroxy radical and DPPH scavenging activity of crude protein extract of Leucas linifolia: A folk medicinal plant. Asian J. Plant Sci. Res. 2012. 2(1): 30–35.
3. Anthony K.P. and Saleh M.A. Free radical scavenging and antioxidant activities of silymarin components. Antioxidants. 2013. 2: 398-407.
4. Ghimire B.K., Yoo J.H., Yu C.Y. and Chung I.M. GC–MS analysis of volatile compounds of Perilla frutescens Britton var. Japonica accessions: Morphological and seasonal variability. Asian Pac. J. Trop. Med. 2017. 10(7): 643–651.
5. Yu H., Qiu J.F., Ma L.J., Hu Y.J., Li P. and Wan J.B. Phytochemical and phytopharmacological review of Perilla frutescens L. (Labiatae), a traditional edible-medicinal herb in China. Food Chem. Toxicol. 2017. 108: 375–391.
6. Zhou X.J., Yan L.L., Yin P.P., Shi L.L., Zhang J.H., Liu Y.J. and Ma C. Structural characterisation and antioxidant activity evaluation of phenolic compounds from cold-pressed Perilla frutescens var. arguta seed flour. Food Chem. 2014. 164: 150–157.
7. Suk N. and Hwan J. Characterisation of phenolic phytochemicals and quality changes related to the harvest times from the leaves of Korean purple perilla (Perilla frutescens). Food Chem. 2011. 124(2): 556–562.
8. Liu J., Wan Y., Zhao Z. and Chen H. Determination of the content of rosmarinic acid by HPLC and analytical comparison of volatile constituents by GC-MS in different parts of Perilla frutescens (L.) Britt. Chem. Cent. J. 2013. 7(61).
9. Müller-waldeck F., Sitzmann J., Schnitzler W.H. and Graßmann J. Determination of toxic perilla ketone, secondary plant metabolites and antioxidative capacity in five Perilla frutescens L. varieties. Food Chem. Toxicol. 2010. 48(1): 264–270.
10. Jeon I.H., Kim H.S., Kang H.J., Lee H.S., Jeong S.Il., Kimand S.J. and Jang S.Il. Anti-inflammatory and antipruritic effects of luteolin from perilla (P. frutescens L.) leaves. Molecules. 2014. 19: 6941-6951.
11. Kamei R., Fujimura T., Matsuda M., Kakihara K., Hirakawa N., Baba K., Ono K., Arakawa K. and Kawamoto S. A flavanone derivative from the Asian medicinal herb (Perilla frutescens) potently suppresses IgE-mediated immediate hypersensitivity reactions. Biochem. Biophys. Res. Commun. 2017. 483(1): 674-679.
12. Ha T.J., Lee J.H., Lee M.H., Lee B.W., Kwon H.S., Park C.H., Shim K.B., Kim H.T., Baek I.Y. and Jang D.S. Isolation and identification of phenolic compounds from the seeds of Perilla frutescens (L.) and their inhibitory activities against α-glucosidase and aldose reductase. Food Chem. 2012. 135(3): 1397–1403.
13. Ueda H., Yamazaki C. and Yamazaki M. Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens. Biol. Pharmaceut. Bull. 2002. 25: 1197–1202.
14. Osakabe N., Yasuda A., Natsume M. and Yoshikawa T. Rosmarinic acid inhibits epidermal inflammatory responses: anticarcinogenic effect of Perilla frutescens extract in the murine two-stage skin model. Carcinogenesis. 2004. 25: 549–557.
15. Oh H.A., Park C.S., Ahn H.J., Park Y.S. and Kim H.M. Effect of Perilla frutescens var. acuta Kudo and rosmarinic acid on allergic inflammatory reactions. Exp. Biol. Med. (Maywood). 2011. 236: 99-106.
16. Jun H. Il., Kim B.T., Song G.S. and Kim Y.S. Structural characterization of phenolic antioxidants from purple perilla (Perilla frutescens var. acuta) leaves. Food Chem. 2014. 148: 367–372.
17. Trease G.E. and Evans W.C. Pharmacognosy. 15th ed. Saunders, London. 2002.
18. Duan X., Jiang Y., Su X., Zhang Z. and Shi J. Antioxidant properties of anthocyanins extracted from litchi (Litchi chinenesis Sonn.) fruit pericarp tissues in relation to their role in the pericarp browning. Food Chem. 2007. 101: 1365–1371.
19. Yoon S.B., Lee Y.J., Park S.K., Kim H.C., Bae H., Ko S.G., Choi H.Y., Oh M.S. and Park W. Anti-inflammatory effects of Scutellaria baicalensis water extract on LPS-activated RAW 264.7 macrophages. J. Ethnopharmacol. 2009. 125: 286–290.
20. Leelapornpisid P., Mungmai L., Sirithunyalug B. and Jiranusornkul S. A novel moisturizer extracted from freshwater macroalga [Rhizoclonium hieroglyphicum (C.Agardh) Kützing] for skin care cosmetic. Chiang Mai J. Sci. 2014. 41(5.2): 1195-1207.
21. Barel A.O. and Maibach H.I. In Vivo Irritation. In: Bashir S.J. and Maibach H.I., editors. Handbook of Cosmetic Science and Technology 3rd. Informa healthcare, New York. 2009: 107-118.
22. OECD Guideline for the Testing Chemicals. Acute Dermal Irritation/Corrosion 404. 2002.
23. Yin L., Han H., Zheng X., Wang G., Li Y. and Wang W. Flavonoids analysis and antioxidant, antimicrobial, and anti-inflammatory activities of crude and purified extracts from Veronicastrum latifolium. Ind crops prod. 2019. 137: 652-661.
24. Benzidia B., Barcouchi M., Hammouch H., Belahbib N., Zouarhi M., Erramli H., Daoud N.A., Badrane N., Hajjaji N. Chemical composition and antioxidant activity of tannins extract from green rind of Aloe vera (L.) Burm. F. J. King Saud Univ. 2019. 31: 1175-1181.
25. Diaz P., Jeong S.C., Lee S., Khoo C. and Koyyalamudi S.R. Antioxidant and anti-inflammatory activities of selected medicinal plants and fungi containing phenolic and flavonoid compounds. Chin. Med. 2012. 7: 26.
26. Maleki E.H., Bahrami A.R., Sadeghian H. and Matin M.M. Discovering the structure–activity relationships of different O-prenylated coumarin derivatives as effective anticancer agents in human cervical cancer cells. Toxicol in Vitro. 2020. 63: 104745.
27. Chatha S.A.S., Hussain A.I., Bajwa J. and Sagir M. Antioxidant activity of different solvent extracts of rice bran at accelerated storage of sunflower oil. J. Food Lipids. 2006. 13(4): 424-433.
28. Rahman M., Islam B., Biswas M. and Alam K. In vitro antioxidant and free radical scavenging activity of different parts of Tabebuia pallida growing in Bangladesh. BMC. Res. Notes. 2015. 8: 621.
29. Huo M., Cui X., Xue J., Chi G., Gao R., Deng X., Guan S., Wei J., Soromou L.W., Feng H. and Wang D. Anti-inflammatory effects of linalool in RAW 264.7 macrophages and lipopolysaccharide-induced lung injury model. J. Surg. Res. 2013. 180(1): 47-54.
30. Fritsche K.L. The science of fatty acids and inflammation. Adv. Nutr. 2015. 6(3): 293–301.
31. Li H., Ge Y., Luo Z., Zhou Y., Zhang X., Zhang J. and Fu Q. Evaluation of the chemical composition, antioxidant and anti-inflammatory activities of distillate and residue fractions of sweet basil essential oil. J. Food Sci. Technol. 2017. 54(7): 1882–1890.
32. Carrillo C., Cavia M.M. and Alonso-Torre S. Role of oleic acid in immune system; mechanism of action. Nutr. Hosp. 2012. 27(4): 978-90.
33. Chen F., Liu S., Zhao Z., Gao W., Ma Y., Wang X., Yan S. and Luo D. Ultrasound pre-treatment combined with microwave-assisted hydrodistillation of essential oils from Perilla frutescens (L.) Britt. leaves and its chemical composition and biological activity. Ind crops prod. 2020.143: 111908
2. Ramakrishna H., Murthy S.S. and Murthy P.G. Hydroxy radical and DPPH scavenging activity of crude protein extract of Leucas linifolia: A folk medicinal plant. Asian J. Plant Sci. Res. 2012. 2(1): 30–35.
3. Anthony K.P. and Saleh M.A. Free radical scavenging and antioxidant activities of silymarin components. Antioxidants. 2013. 2: 398-407.
4. Ghimire B.K., Yoo J.H., Yu C.Y. and Chung I.M. GC–MS analysis of volatile compounds of Perilla frutescens Britton var. Japonica accessions: Morphological and seasonal variability. Asian Pac. J. Trop. Med. 2017. 10(7): 643–651.
5. Yu H., Qiu J.F., Ma L.J., Hu Y.J., Li P. and Wan J.B. Phytochemical and phytopharmacological review of Perilla frutescens L. (Labiatae), a traditional edible-medicinal herb in China. Food Chem. Toxicol. 2017. 108: 375–391.
6. Zhou X.J., Yan L.L., Yin P.P., Shi L.L., Zhang J.H., Liu Y.J. and Ma C. Structural characterisation and antioxidant activity evaluation of phenolic compounds from cold-pressed Perilla frutescens var. arguta seed flour. Food Chem. 2014. 164: 150–157.
7. Suk N. and Hwan J. Characterisation of phenolic phytochemicals and quality changes related to the harvest times from the leaves of Korean purple perilla (Perilla frutescens). Food Chem. 2011. 124(2): 556–562.
8. Liu J., Wan Y., Zhao Z. and Chen H. Determination of the content of rosmarinic acid by HPLC and analytical comparison of volatile constituents by GC-MS in different parts of Perilla frutescens (L.) Britt. Chem. Cent. J. 2013. 7(61).
9. Müller-waldeck F., Sitzmann J., Schnitzler W.H. and Graßmann J. Determination of toxic perilla ketone, secondary plant metabolites and antioxidative capacity in five Perilla frutescens L. varieties. Food Chem. Toxicol. 2010. 48(1): 264–270.
10. Jeon I.H., Kim H.S., Kang H.J., Lee H.S., Jeong S.Il., Kimand S.J. and Jang S.Il. Anti-inflammatory and antipruritic effects of luteolin from perilla (P. frutescens L.) leaves. Molecules. 2014. 19: 6941-6951.
11. Kamei R., Fujimura T., Matsuda M., Kakihara K., Hirakawa N., Baba K., Ono K., Arakawa K. and Kawamoto S. A flavanone derivative from the Asian medicinal herb (Perilla frutescens) potently suppresses IgE-mediated immediate hypersensitivity reactions. Biochem. Biophys. Res. Commun. 2017. 483(1): 674-679.
12. Ha T.J., Lee J.H., Lee M.H., Lee B.W., Kwon H.S., Park C.H., Shim K.B., Kim H.T., Baek I.Y. and Jang D.S. Isolation and identification of phenolic compounds from the seeds of Perilla frutescens (L.) and their inhibitory activities against α-glucosidase and aldose reductase. Food Chem. 2012. 135(3): 1397–1403.
13. Ueda H., Yamazaki C. and Yamazaki M. Luteolin as an anti-inflammatory and anti-allergic constituent of Perilla frutescens. Biol. Pharmaceut. Bull. 2002. 25: 1197–1202.
14. Osakabe N., Yasuda A., Natsume M. and Yoshikawa T. Rosmarinic acid inhibits epidermal inflammatory responses: anticarcinogenic effect of Perilla frutescens extract in the murine two-stage skin model. Carcinogenesis. 2004. 25: 549–557.
15. Oh H.A., Park C.S., Ahn H.J., Park Y.S. and Kim H.M. Effect of Perilla frutescens var. acuta Kudo and rosmarinic acid on allergic inflammatory reactions. Exp. Biol. Med. (Maywood). 2011. 236: 99-106.
16. Jun H. Il., Kim B.T., Song G.S. and Kim Y.S. Structural characterization of phenolic antioxidants from purple perilla (Perilla frutescens var. acuta) leaves. Food Chem. 2014. 148: 367–372.
17. Trease G.E. and Evans W.C. Pharmacognosy. 15th ed. Saunders, London. 2002.
18. Duan X., Jiang Y., Su X., Zhang Z. and Shi J. Antioxidant properties of anthocyanins extracted from litchi (Litchi chinenesis Sonn.) fruit pericarp tissues in relation to their role in the pericarp browning. Food Chem. 2007. 101: 1365–1371.
19. Yoon S.B., Lee Y.J., Park S.K., Kim H.C., Bae H., Ko S.G., Choi H.Y., Oh M.S. and Park W. Anti-inflammatory effects of Scutellaria baicalensis water extract on LPS-activated RAW 264.7 macrophages. J. Ethnopharmacol. 2009. 125: 286–290.
20. Leelapornpisid P., Mungmai L., Sirithunyalug B. and Jiranusornkul S. A novel moisturizer extracted from freshwater macroalga [Rhizoclonium hieroglyphicum (C.Agardh) Kützing] for skin care cosmetic. Chiang Mai J. Sci. 2014. 41(5.2): 1195-1207.
21. Barel A.O. and Maibach H.I. In Vivo Irritation. In: Bashir S.J. and Maibach H.I., editors. Handbook of Cosmetic Science and Technology 3rd. Informa healthcare, New York. 2009: 107-118.
22. OECD Guideline for the Testing Chemicals. Acute Dermal Irritation/Corrosion 404. 2002.
23. Yin L., Han H., Zheng X., Wang G., Li Y. and Wang W. Flavonoids analysis and antioxidant, antimicrobial, and anti-inflammatory activities of crude and purified extracts from Veronicastrum latifolium. Ind crops prod. 2019. 137: 652-661.
24. Benzidia B., Barcouchi M., Hammouch H., Belahbib N., Zouarhi M., Erramli H., Daoud N.A., Badrane N., Hajjaji N. Chemical composition and antioxidant activity of tannins extract from green rind of Aloe vera (L.) Burm. F. J. King Saud Univ. 2019. 31: 1175-1181.
25. Diaz P., Jeong S.C., Lee S., Khoo C. and Koyyalamudi S.R. Antioxidant and anti-inflammatory activities of selected medicinal plants and fungi containing phenolic and flavonoid compounds. Chin. Med. 2012. 7: 26.
26. Maleki E.H., Bahrami A.R., Sadeghian H. and Matin M.M. Discovering the structure–activity relationships of different O-prenylated coumarin derivatives as effective anticancer agents in human cervical cancer cells. Toxicol in Vitro. 2020. 63: 104745.
27. Chatha S.A.S., Hussain A.I., Bajwa J. and Sagir M. Antioxidant activity of different solvent extracts of rice bran at accelerated storage of sunflower oil. J. Food Lipids. 2006. 13(4): 424-433.
28. Rahman M., Islam B., Biswas M. and Alam K. In vitro antioxidant and free radical scavenging activity of different parts of Tabebuia pallida growing in Bangladesh. BMC. Res. Notes. 2015. 8: 621.
29. Huo M., Cui X., Xue J., Chi G., Gao R., Deng X., Guan S., Wei J., Soromou L.W., Feng H. and Wang D. Anti-inflammatory effects of linalool in RAW 264.7 macrophages and lipopolysaccharide-induced lung injury model. J. Surg. Res. 2013. 180(1): 47-54.
30. Fritsche K.L. The science of fatty acids and inflammation. Adv. Nutr. 2015. 6(3): 293–301.
31. Li H., Ge Y., Luo Z., Zhou Y., Zhang X., Zhang J. and Fu Q. Evaluation of the chemical composition, antioxidant and anti-inflammatory activities of distillate and residue fractions of sweet basil essential oil. J. Food Sci. Technol. 2017. 54(7): 1882–1890.
32. Carrillo C., Cavia M.M. and Alonso-Torre S. Role of oleic acid in immune system; mechanism of action. Nutr. Hosp. 2012. 27(4): 978-90.
33. Chen F., Liu S., Zhao Z., Gao W., Ma Y., Wang X., Yan S. and Luo D. Ultrasound pre-treatment combined with microwave-assisted hydrodistillation of essential oils from Perilla frutescens (L.) Britt. leaves and its chemical composition and biological activity. Ind crops prod. 2020.143: 111908