Phytochemicals detected in Lysiphyllum strychnifolium (Craib) A. Schmitz stem extracts and their log-patterns of ABTS radical scavenging activities

Netiya Karaket; Kanoktip Pansuksan

doi:10.7324/JAPS.2024.156279

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Abstract

Lysiphyllum strychnifolium (W. G. Craib) A. Schmitz is a plant with various medicinal properties, including antioxidant activity and detoxification. In this study, we initially screened the phytochemical compounds in methanolic (MeOH) extract by gas chromatography-mass spectrometry (GC-MS) technique and blasted them with NIST17 library. After screening, some bioactive compounds, such as 1,2-Benzenediol (3.68%); 1,2,3-Benzenetriol (12.16%); 1,3,5-Benzenetriol (24.30%); 13-Docosenamide, (Z)-(3.41%); and D-allose (24.46%) with reported antioxidant properties were identified; Then, the next analysis of phytochemicals; including catechin and quercetin in MeOH, ethanolic (EtOH), and aqueous extracts by the high performance liquid chromatography (HPLC). The results revealed that catechin contents in all extracts fell within the range of 3.46–9.55 mg/g DW. However, quercetin is figured out in all extracts except in the EtOH extract, which may be due to its low content and the limitation of detection. Subsequently, we tested the free radical scavenging activities of all extracts using the ABTS method. It is noteworthy that all extracts exhibited significant antioxidant activities, showing a logarithmic pattern when plotting the graph of decolorization versus concentrations, unlike the linear pattern observed with the standard Trolox. Our study confirms that L. strychnifolium extracts have excellent antioxidant activities and represents a potential candidate for alternative source of antioxidant agents in medicinal application.

Keyword: Lysiphyllum strychnifolium phytochemical GC-MS antioxidant ABTS

Citation:

Karaket N, Pansuksan K. Phytochemicals detected in Lysiphyllum strychnifolium (Craib) A. Schmitz stem extracts and their log-patterns of ABTS radical scavenging activities. J Appl Pharm Sci. 2024. Online First. http://doi.org/10.7324/JAPS.2024.156279

Copyright: © The Author(s). This is an open-access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Reference

1. Sampaopan Y, Kitprapiumpon N, Kongkiatpaiboon S, Duangdee N, Wongyai S. Isolation and HPLC Analysis of Astilbin in Lysiphyllum strychnifolium (syn. Bauhinia strychnifolia) Stems. Sci Technology Asia. 2021; 26(1): 208-15.
2. Sampaopan Y, Suksaeree J. Formulation Development and pharmaceutical evaluation of lysiphyllum strychnifolium topical patches for their anti-inflammatory potential. AAPS Pharm Sci Tech. 2022;23(5):116. https://doi.org/10.1208/s12249-022-02269-x
3. Sukprasert S, Pansuksan K, Sriyakul K. Lysiphyllum strychnifolium (Craib) A. Schmitz extract, a novel neuraminidase inhibitor of avian influenza virus subtype H5N1. J Herb Med, 2020a;20:100330. https://doi.org/10.1016/j.hermed.2020.100330
4. Goli AS, Sato VH, Sato H, Chewchinda S, Leanpolchareanchai J, Nontakham J, Yahuafai J, Thilavech T, Meesawatsom P, Maitree M. Antihyperglycemic effects of Lysiphyllum strychnifolium leaf extract in vitro and in vivo. Pharm Biol. 2023;61(1):189-200. https://doi.org/10.1080/13880209.2022.2160771
5. Sato V, Chewchinda S, Nuamnaichati N, Mangmool S, Bunleu S, Lertsatitthanakorn P, Ohta S, Sato H. Pharmacological mechanisms of the water leaves extract of Lysiphyllum strychnifolium for its anti-inflammatory and anti-hyperuricemic actions for gout treatment. Pharmacogn Mag, 2019;15(60):98-106. https://doi.org/10.4103/pm.pm_14_18
6. Noonong K, Pranweerapaiboon K, Chaithirayanon K, Rurayarn K, Ditracha P, Changklungmoa N, Kueakhai P, Hiransai1 P, Bunluepuech K. Antidiabetic potential of Lysiphyllum strychnifolium (Craib) A. Schmitz compounds in human intestinal epithelial Caco-2 cells and molecular docking-based approaches. BMC Complement Med Ther, 202222:235.
7. Kuendee N, Naladta A, Kulsirirat T, Yimsoo T, Yingmema W, Pansuksan K, Sathirakul K, Sukprasert S. Lysiphyllum strychnifolium (Craib) A. Schmitz extracts moderate the expression of drug-metabolizing enzymes: In Vivo study to clinical propose. Pharmaceuticals. 2023;16(2):237. https://doi.org/10.3390/ph16020237
8. Ayoka TO, Ezema1 BO, Eze CN, Nnadi CO. Antioxidants for the prevention and treatment of non-communicable diseases. J Explor Res Pharmacol. 2022;7(3):178-88. https://doi.org/10.14218/JERP.2022.00028
9. Pereira DM, Valentão P, Pereira JA, Andrade PB. Phenolics: from chemistry to biology. Molecules, 2009;14(6):2202-11. https://doi.org/10.3390/molecules14062202
10. Rizvi S, Raza ST, Ahmed F, Ahmad A, Abbas S, Mahdi F. The role of vitamin e in human health and some diseases. Sultan Qaboos Univ Med J. 2014;14(2):e157-65.
11. Tsao R. Chemistry and biochemistry of dietary polyphenols. Nutrients. 2010;2(12):1231-46. https://doi.org/10.3390/nu2121231
12. Michalak M. Plant-derived antioxidants: significance in skin health and the ageing process. Int J Mol Sci, 2022;23(2):585. https://doi.org/10.3390/ijms23020585
13. Sukprasert S, Deenonpoe R, Yimsoo T, Yingmema W, Prasopdee S, Krajang A, Kornthong N, Pattaraarchachai J, Daduang S. Antidote activity and protective effects of Lysiphyllum strychnifolium (Craib) A. Schmitz extract against organophosphate pesticide in omethoate-treated rats. J Tradit Complement Med. 2020b;11(3):189-96. https://doi.org/10.1016/j.jtcme.2020.03.001
14. Praparatana R, Maliyam P, Barrows LR, Puttarak P. Flavonoids and phenols, the potential anti-diabetic compounds from Bauhinia strychnifolia Craib. Stem. Molecules. 2022;27(8):2393. https://doi.org/10.3390/molecules27082393
15. Yuangang Zu, Chunying Li, Yujie Fu, Chunjian Zhao. Simultaneous determination of catechin, rutin, quercetin kaempferol and isorhamnetin in the extract of sea buckthorn (Hippophae rhamnoides L.) leaves by RP-HPLC with DAD. J Pharm Biomed Anal, 2006; 41(3): 714-19. https://doi.org/10.1016/j.jpba.2005.04.052
16. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med, 1999; 26(9-10): 1231- 37. https://doi.org/10.1016/S0891-5849(98)00315-3
17. Chong YM, Chang SK, Sia WCM, Yim HS. Antioxidant efficacy of mangosteen (Garcinia mangostana Linn.) peel extracts in sunflower oil during accelerated storage. Food Biosci, 2015;12:18-25. https://doi.org/10.1016/j.fbio.2015.07.002
18. Hashemi SMB, Khaneghah AM, Koubaa M, Lopez-Cervantes J, Yousefabad SHA, Hosseini SF, Karimi M, Motazedian A, Asadifard S. Novel edible oil sources: microwave heating and chemical properties. Food Res Int. 2017;92:147-53. https://doi.org/10.1016/j.foodres.2016.11.033
19. De La Cruz JP, Ruiz-Moreno MI, Guerrero A, López-Villodres JA, Reyes JJ, Espartero JL, Labajos MT, González-Correa JA. Role of the catechol group in the antioxidant and neuroprotective effects of virgin olive oil components in rat brain. J Nutr Biochem. 2015;26(5):549-55.. https://doi.org/10.1016/j.jnutbio.2014.12.013
20. Xie X, Wu F, Tian J, Liu Z, He H, Bao D, Li G, Li H, Chen J, Lai Y, Chen Z, Fan J, Chen G, Lai C. Pyrocatechol alleviates cisplatin-induced acute kidney injury by inhibiting ROS production. Oxid Med Cell Longev. 2022;2022:2158644. https://doi.org/10.1155/2022/2158644
21. Choe E. Roles and action mechanisms of herbs added to the emulsion on its lipid oxidation. Food Sci Biotechnol. 2020;29:1165-79. https://doi.org/10.1007/s10068-020-00800-z
22. OECD (2003a). SIDS Initial Assessment Profile (SIAP) on 1,2-Dihydroxybenzene (pyrocatechol, catechol) (120-80-9). Accessed September 2023. http://webnet.oecd.org/Hpv/UI/handler.axd?id=0ecbfe38-1c21-4562-aefd-220c345516a3
23. Yang C, Wang B, Wang J, Xia S, Wu Y. Effect of pyrogallic acid (1,2,3-benzenetriol) polyphenol-protein covalent conjugation reaction degree on structure and antioxidant properties of pumpkin (Cucurbita sp.) seed protein isolate. LWT-Food Sci Technol. 2019;109:443-49. https://doi.org/10.1016/j.lwt.2019.04.034
24. Baharuddin N. Potential use of Quercus infectoria gall extracts against urinary tract pathogenic bacteria. Int J Res Pharmacol Pharmacother. 2014;3:184-91.
25. Zhang Y, Yang S, Qiu Z, Huang L, Huang L, Liang Y, Liu X, Wang M, Zhou B. Pyrogallol enhances therapeutic effect of human umbilical cord mesenchymal stem cells against LPS-mediated inflammation and lung injury via activation of Nrf2/HO-1 signaling. Free Radic Biol Med, 2022;191:66-81. https://doi.org/10.1016/j.freeradbiomed.2022.08.030
26. Finewax Z, de Gouw J, Ziemann P. Products and secondary organic aerosol yields from the OH and NO3 radical-initiated oxidation of resorcinol. ACS Earth Space Chem. 2019;3:1248-59. https://doi.org/10.1021/acsearthspacechem.9b00112
27. Jayawardhana HHACK, Jayawardena TU, Sanjeewa KKA, Liyanage NM, Nagahawatta DP, Lee H-G, Kim J-I, Jeon Y-J. Marine algal polyphenols as skin protective agents: current status and future prospectives. Mar Drugs. 2023;21(5):285. https://doi.org/10.3390/md21050285
28. Kishida K, Iida T, Yamada T, Toyoda Y. d-Allose is absorbed via sodium-dependent glucose cotransporter 1 (SGLT1) in the rat small intestine. Metabol Open. 2021;11:100112. https://doi.org/10.1016/j.metop.2021.100112
29. Ishihara Y, Katayama K, Sakabe M, Kitamura M, Aizawa M, Takara M, Itoh K. Antioxidant properties of rare sugar D-allose: effects on mitochondrial reactive oxygen species production in Neuro2A cells. J Biosci Bioeng. 2011;112(6):638-42. ISSN 1389-1723. https://doi.org/10.1016/j.jbiosc.2011.08.005
30. Ju J, Hou R, Zhang P. D-allose alleviates ischemia/reperfusion (I/R) injury in skin flap via MKP-1. Mol Med. 2020;26(1):21. https://doi.org/10.1186/s10020-020-0138-6
31. Tohi Y, Taoka R, Zhang X, Matsuoka Y, Yoshihara A, Ibuki E, Haba R, Akimitsu K, Izumori K, Kakehi Y, Sugimoto M. Antitumor effects of orally administered rare sugar D-Allose in bladder cancer. Int J Mol Sci. 2022;23(12):6771. https://doi.org/10.3390/ijms23126771
32. Shareef H, Haidar J, Hussein H, Hameed I. Antibacterial effect of ginger (Zingiber officinale) Roscoe and bioactive chemical analysis using gas chromatography mass spectrum. Orient J Chem. 2016;(32):817-37. https://doi.org/10.13005/ojc/320207
33. Kalender Y, Kaya S, Durak D, Uzun FG, Demir F. Protective effects of catechin and quercetin on antioxidant status, lipid peroxidation and testis-histoarchitecture induced by chlorpyrifos in male rats. Environ Toxicol Pharmacol. 2012;33(2):141-148. https://doi.org/10.1016/j.etap.2011.12.008

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1. Sampaopan Y, Kitprapiumpon N, Kongkiatpaiboon S, Duangdee N, Wongyai S. Isolation and HPLC Analysis of Astilbin in Lysiphyllum strychnifolium (syn. Bauhinia strychnifolia) Stems. Sci Technology Asia. 2021; 26(1): 208-15.

2. Sampaopan Y, Suksaeree J. Formulation Development and pharmaceutical evaluation of lysiphyllum strychnifolium topical patches for their anti-inflammatory potential. AAPS Pharm Sci Tech. 2022;23(5):116. https://doi.org/10.1208/s12249-022-02269-x

3. Sukprasert S, Pansuksan K, Sriyakul K. Lysiphyllum strychnifolium (Craib) A. Schmitz extract, a novel neuraminidase inhibitor of avian influenza virus subtype H5N1. J Herb Med, 2020a;20:100330. https://doi.org/10.1016/j.hermed.2020.100330

4. Goli AS, Sato VH, Sato H, Chewchinda S, Leanpolchareanchai J, Nontakham J, Yahuafai J, Thilavech T, Meesawatsom P, Maitree M. Antihyperglycemic effects of Lysiphyllum strychnifolium leaf extract in vitro and in vivo. Pharm Biol. 2023;61(1):189-200. https://doi.org/10.1080/13880209.2022.2160771

5. Sato V, Chewchinda S, Nuamnaichati N, Mangmool S, Bunleu S, Lertsatitthanakorn P, Ohta S, Sato H. Pharmacological mechanisms of the water leaves extract of Lysiphyllum strychnifolium for its anti-inflammatory and anti-hyperuricemic actions for gout treatment. Pharmacogn Mag, 2019;15(60):98-106. https://doi.org/10.4103/pm.pm_14_18

6. Noonong K, Pranweerapaiboon K, Chaithirayanon K, Rurayarn K, Ditracha P, Changklungmoa N, Kueakhai P, Hiransai1 P, Bunluepuech K. Antidiabetic potential of Lysiphyllum strychnifolium (Craib) A. Schmitz compounds in human intestinal epithelial Caco-2 cells and molecular docking-based approaches. BMC Complement Med Ther, 202222:235.

7. Kuendee N, Naladta A, Kulsirirat T, Yimsoo T, Yingmema W, Pansuksan K, Sathirakul K, Sukprasert S. Lysiphyllum strychnifolium (Craib) A. Schmitz extracts moderate the expression of drug-metabolizing enzymes: In Vivo study to clinical propose. Pharmaceuticals. 2023;16(2):237. https://doi.org/10.3390/ph16020237

8. Ayoka TO, Ezema1 BO, Eze CN, Nnadi CO. Antioxidants for the prevention and treatment of non-communicable diseases. J Explor Res Pharmacol. 2022;7(3):178-88. https://doi.org/10.14218/JERP.2022.00028

9. Pereira DM, Valentão P, Pereira JA, Andrade PB. Phenolics: from chemistry to biology. Molecules, 2009;14(6):2202-11. https://doi.org/10.3390/molecules14062202

10. Rizvi S, Raza ST, Ahmed F, Ahmad A, Abbas S, Mahdi F. The role of vitamin e in human health and some diseases. Sultan Qaboos Univ Med J. 2014;14(2):e157-65.

11. Tsao R. Chemistry and biochemistry of dietary polyphenols. Nutrients. 2010;2(12):1231-46. https://doi.org/10.3390/nu2121231

12. Michalak M. Plant-derived antioxidants: significance in skin health and the ageing process. Int J Mol Sci, 2022;23(2):585. https://doi.org/10.3390/ijms23020585

13. Sukprasert S, Deenonpoe R, Yimsoo T, Yingmema W, Prasopdee S, Krajang A, Kornthong N, Pattaraarchachai J, Daduang S. Antidote activity and protective effects of Lysiphyllum strychnifolium (Craib) A. Schmitz extract against organophosphate pesticide in omethoate-treated rats. J Tradit Complement Med. 2020b;11(3):189-96. https://doi.org/10.1016/j.jtcme.2020.03.001

14. Praparatana R, Maliyam P, Barrows LR, Puttarak P. Flavonoids and phenols, the potential anti-diabetic compounds from Bauhinia strychnifolia Craib. Stem. Molecules. 2022;27(8):2393. https://doi.org/10.3390/molecules27082393

15. Yuangang Zu, Chunying Li, Yujie Fu, Chunjian Zhao. Simultaneous determination of catechin, rutin, quercetin kaempferol and isorhamnetin in the extract of sea buckthorn (Hippophae rhamnoides L.) leaves by RP-HPLC with DAD. J Pharm Biomed Anal, 2006; 41(3): 714-19. https://doi.org/10.1016/j.jpba.2005.04.052

16. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med, 1999; 26(9-10): 1231- 37. https://doi.org/10.1016/S0891-5849(98)00315-3

17. Chong YM, Chang SK, Sia WCM, Yim HS. Antioxidant efficacy of mangosteen (Garcinia mangostana Linn.) peel extracts in sunflower oil during accelerated storage. Food Biosci, 2015;12:18-25. https://doi.org/10.1016/j.fbio.2015.07.002

18. Hashemi SMB, Khaneghah AM, Koubaa M, Lopez-Cervantes J, Yousefabad SHA, Hosseini SF, Karimi M, Motazedian A, Asadifard S. Novel edible oil sources: microwave heating and chemical properties. Food Res Int. 2017;92:147-53. https://doi.org/10.1016/j.foodres.2016.11.033

19. De La Cruz JP, Ruiz-Moreno MI, Guerrero A, López-Villodres JA, Reyes JJ, Espartero JL, Labajos MT, González-Correa JA. Role of the catechol group in the antioxidant and neuroprotective effects of virgin olive oil components in rat brain. J Nutr Biochem. 2015;26(5):549-55.. https://doi.org/10.1016/j.jnutbio.2014.12.013

20. Xie X, Wu F, Tian J, Liu Z, He H, Bao D, Li G, Li H, Chen J, Lai Y, Chen Z, Fan J, Chen G, Lai C. Pyrocatechol alleviates cisplatin-induced acute kidney injury by inhibiting ROS production. Oxid Med Cell Longev. 2022;2022:2158644. https://doi.org/10.1155/2022/2158644

21. Choe E. Roles and action mechanisms of herbs added to the emulsion on its lipid oxidation. Food Sci Biotechnol. 2020;29:1165-79. https://doi.org/10.1007/s10068-020-00800-z

22. OECD (2003a). SIDS Initial Assessment Profile (SIAP) on 1,2-Dihydroxybenzene (pyrocatechol, catechol) (120-80-9). Accessed September 2023. http://webnet.oecd.org/Hpv/UI/handler.axd?id=0ecbfe38-1c21-4562-aefd-220c345516a3

23. Yang C, Wang B, Wang J, Xia S, Wu Y. Effect of pyrogallic acid (1,2,3-benzenetriol) polyphenol-protein covalent conjugation reaction degree on structure and antioxidant properties of pumpkin (Cucurbita sp.) seed protein isolate. LWT-Food Sci Technol. 2019;109:443-49. https://doi.org/10.1016/j.lwt.2019.04.034

24. Baharuddin N. Potential use of Quercus infectoria gall extracts against urinary tract pathogenic bacteria. Int J Res Pharmacol Pharmacother. 2014;3:184-91.

25. Zhang Y, Yang S, Qiu Z, Huang L, Huang L, Liang Y, Liu X, Wang M, Zhou B. Pyrogallol enhances therapeutic effect of human umbilical cord mesenchymal stem cells against LPS-mediated inflammation and lung injury via activation of Nrf2/HO-1 signaling. Free Radic Biol Med, 2022;191:66-81. https://doi.org/10.1016/j.freeradbiomed.2022.08.030

26. Finewax Z, de Gouw J, Ziemann P. Products and secondary organic aerosol yields from the OH and NO3 radical-initiated oxidation of resorcinol. ACS Earth Space Chem. 2019;3:1248-59. https://doi.org/10.1021/acsearthspacechem.9b00112

27. Jayawardhana HHACK, Jayawardena TU, Sanjeewa KKA, Liyanage NM, Nagahawatta DP, Lee H-G, Kim J-I, Jeon Y-J. Marine algal polyphenols as skin protective agents: current status and future prospectives. Mar Drugs. 2023;21(5):285. https://doi.org/10.3390/md21050285

28. Kishida K, Iida T, Yamada T, Toyoda Y. d-Allose is absorbed via sodium-dependent glucose cotransporter 1 (SGLT1) in the rat small intestine. Metabol Open. 2021;11:100112. https://doi.org/10.1016/j.metop.2021.100112

29. Ishihara Y, Katayama K, Sakabe M, Kitamura M, Aizawa M, Takara M, Itoh K. Antioxidant properties of rare sugar D-allose: effects on mitochondrial reactive oxygen species production in Neuro2A cells. J Biosci Bioeng. 2011;112(6):638-42. ISSN 1389-1723. https://doi.org/10.1016/j.jbiosc.2011.08.005

30. Ju J, Hou R, Zhang P. D-allose alleviates ischemia/reperfusion (I/R) injury in skin flap via MKP-1. Mol Med. 2020;26(1):21. https://doi.org/10.1186/s10020-020-0138-6

31. Tohi Y, Taoka R, Zhang X, Matsuoka Y, Yoshihara A, Ibuki E, Haba R, Akimitsu K, Izumori K, Kakehi Y, Sugimoto M. Antitumor effects of orally administered rare sugar D-Allose in bladder cancer. Int J Mol Sci. 2022;23(12):6771. https://doi.org/10.3390/ijms23126771

32. Shareef H, Haidar J, Hussein H, Hameed I. Antibacterial effect of ginger (Zingiber officinale) Roscoe and bioactive chemical analysis using gas chromatography mass spectrum. Orient J Chem. 2016;(32):817-37. https://doi.org/10.13005/ojc/320207

33. Kalender Y, Kaya S, Durak D, Uzun FG, Demir F. Protective effects of catechin and quercetin on antioxidant status, lipid peroxidation and testis-histoarchitecture induced by chlorpyrifos in male rats. Environ Toxicol Pharmacol. 2012;33(2):141-148. https://doi.org/10.1016/j.etap.2011.12.008