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Antimalarial Evaluation of the Chemical Constituents Isolated from Dendrocalamus asper

Year 2021, , 995 - 1002, 30.11.2021
https://doi.org/10.18596/jotcsa.904529

Abstract

Bamboo shoots of Dendrocalamus asper is very important for human health because of its high content of dietary fiber, low sugar, negligible amount of fat, rich in vitamins and minerals. In search of new potential antimalarial agents, the chemical constituents of bamboo shoots were evaluated againts the P. falciparum strain 3D7. One new metabolite, (11E,13E,17E,19E)-dimethyl-15,16-dibutoxytriconta-11,13,17,19-tetraenedioate (1) along with the four known compounds; β-sitosterol (2), methyl-4-hydroxybenzoate (3), 1-methoxy-4-(methoxymethyl)benzene (4) and 4-hydroxybenzaldehyde (5) were isolated from the crude extract using chromatographic methods: MPLC, UPLC/MS, analytical and preparative HPLC. Among these, compounds 1, 3 and 4 showed promising antimalarial activity with IC50 between 0.8-2.2 μg/mL. The molecular docking between the most potent compound 3 and dihydrofolate reductase-thymidylate synthase (DHFR-TS) was done to understand and exploring ligand-receptor interactions and hypothesize the compound's refinements

Supporting Institution

Universiti Sains Malaysia

Project Number

USM RUT grant (1001/PKIMIA/8011072)

Thanks

Wong, K.T also extended his appreciation to Prof Osada, H., Nogawa, T., and Futamura, Y. from Chemical Biology Research Group, RIKEN Center for Suitainable Resource Science, Wako, Saitama, Japan for providing laboratory facilities and technical assistance under short-term International Program Associate (IPA). We also thanked to Zhang J.L for his contribution for this project.

References

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  • 2. World Health Organisation. 2019 World Malaria Report. Geneva, Switzerland: WHO, 2019.(Accessed 01.03.2020).
  • 3. Jantan I. Medicinal plant research in Malaysia: Scientific interests and advances. Malaysian J. Health Sci. 2004; 2(2):27-46.
  • 4. Schwikkard S, Van Heerden F. Antimalarial activity of plant metabolites. Nat. Prod. Rep. 2002; 19(6): 675-92.
  • 5. Klayman DL. Qinghaosu (artemisinin): an antimalarial drug from China. Science. 1985; 228(4703): 1049-55.
  • 6. Nik Abdul Rahman NN, Furuta T, Kojima S, Takane K, Mohd MA. Antimalarial activity of extracts of Malaysian medicinal plants. J. Ethopharmacol. 1999; 64(3): 249-54.
  • 7. Kant P. Should bamboos and palms be included in CDM forestry projects? IGREC working paper, No. IGREC-07:2010, Institute of Green Economy, New Delhi, 2010.
  • 8. Chaturvedula VSP, Prakash I. Isolation of stigmasterol and β-sitosterol from the dichloromethane extract of Rubus suavissimus. Int. Curr. Pharm. J. 2012; 1(9): 239-42.
  • 9. Aliba MO, Ndukwe IG, Ibrahim H. Isolation and characterization of β-sitosterol from methanol extracts of the stem bark of large-leaved rock fig (Ficus Abutilifolia Miq). J. Appl. Sci. Environ. Manage. 2018; 22(10): 1639-42.
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  • 12. Panyo J, Matsunami K, Panichayupakaranant P. Bioassay-guided isolation and evaluation of antimicrobial compound from Ixora megalophylla against some oral pathogens. Pharm. Biol. 2016; 54(9): 1522-27.
  • 13. Magano J, Chen MH, Clark JD, Nussbaumer T. 2-(Diethylamino)ethanethiol, a new reagent for the odorless deprotection of aromatic methyl ethers. J. Org. Chem. 2006; 71(18): 7103-5.
  • 14. Hayase H, Watanabe N, Lim CL, Nogawa T, Komatsuya K, Kita K, Osada H. Inhibition of Malaria Parasite Growth by Quinomycin A and its derivatives through DNA-Intercalating Activity. Biosci, Biotechnol, Biochem. 2015; 79(4): 633-5.
  • 15. Gamo FJ, Sanz LM, Vidal J, De Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF. Thousands of chemical starting points for antimalarial lead identification. Nature. 2010; 465(7296): 305-10.
  • 16. Vanichtanankul J, Taweechai S, Yuvaniyama J, Vilaivan T, P Chitnumsub, Kamchonwongpaisan S, Yuthavong Y. Trypanosomal Dihydrofolate Reductase Reveals Natural Antifolate Resistance. ACS. Chem. Biol. 2011; 6(9): 905-11.
  • 17. Matin MM, Hasan MS, Uzzaman M, Bhuiyan MMH, Kibria SM, Hossain ME, Roshid MHO. Synthesis, spectroscopic characterization, molecular docking, and ADMET studies of mannopyranoside esters as antimicrobial agents. J. Mol. Struct. 2020; 1222, 128821-33.
  • 18. Ahmad F, Ali M, Alam P. New phytoconstituents from the stem bark of Tinospora cordifolia Miers. Nat. Prod. Res. 2010;24(10): 926-34.
  • 19. Tian JK, Sun F, Cheng YY. Chemical constituents from the roots of Ranunculus ternatus. J. Asian Nat. Prod. Res. 2006; 8(1-2): 35-9.
  • 20. Vijayan N. Structural and optical characterization on solution grown methyl p-hydroxybenzoate single crystals. Indian J. Chem., Sect A. 2007; 46(1): 70-3.
  • 21. Tsai CY, Sung R, Zhuang BR, Sung KS. TiCl4 -activated selective nucleophilic substitution of tert-butyl alcohol and benzyl alcohol with p-donating substituents. Tetrahedron. 2010; 66(34): 6869-72.
  • 22. Kim H, Ralph J, Lu F, Boudet AM, MacKay JJ, Sederoff RR, Ito T, Kawai S, Ohashi H, Higuchi T. NMR analysis of lignins in CAD-deficient plants. Part 1. Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins. Org. Biomol. Chem. 2003; 1(2): 268-81.
Year 2021, , 995 - 1002, 30.11.2021
https://doi.org/10.18596/jotcsa.904529

Abstract

Project Number

USM RUT grant (1001/PKIMIA/8011072)

References

  • 1 Al-Adhroey AH, Nor ZM, Al-Mekhlafi HM, Amran AA, Mahmud R. Antimalarial activity of methanolic leaf extract of Piper betle L. Molecules. 2010; 16(1): 107-18.
  • 2. World Health Organisation. 2019 World Malaria Report. Geneva, Switzerland: WHO, 2019.(Accessed 01.03.2020).
  • 3. Jantan I. Medicinal plant research in Malaysia: Scientific interests and advances. Malaysian J. Health Sci. 2004; 2(2):27-46.
  • 4. Schwikkard S, Van Heerden F. Antimalarial activity of plant metabolites. Nat. Prod. Rep. 2002; 19(6): 675-92.
  • 5. Klayman DL. Qinghaosu (artemisinin): an antimalarial drug from China. Science. 1985; 228(4703): 1049-55.
  • 6. Nik Abdul Rahman NN, Furuta T, Kojima S, Takane K, Mohd MA. Antimalarial activity of extracts of Malaysian medicinal plants. J. Ethopharmacol. 1999; 64(3): 249-54.
  • 7. Kant P. Should bamboos and palms be included in CDM forestry projects? IGREC working paper, No. IGREC-07:2010, Institute of Green Economy, New Delhi, 2010.
  • 8. Chaturvedula VSP, Prakash I. Isolation of stigmasterol and β-sitosterol from the dichloromethane extract of Rubus suavissimus. Int. Curr. Pharm. J. 2012; 1(9): 239-42.
  • 9. Aliba MO, Ndukwe IG, Ibrahim H. Isolation and characterization of β-sitosterol from methanol extracts of the stem bark of large-leaved rock fig (Ficus Abutilifolia Miq). J. Appl. Sci. Environ. Manage. 2018; 22(10): 1639-42.
  • 10. Chang YC, Chang FR, Wu YC. The constituents of Lindera glauca. J. Chin. Chem. Soc. 2000; 47(2): 373-80.
  • 11. Bhaskar G, Solomon M, Babu G, Muralidharan D, Perumal PT. A simple and an efficient indium trichloride catalyzed benzyl etherification. Indian J. Chem., Sect B. 2010; 49B: 795-801.
  • 12. Panyo J, Matsunami K, Panichayupakaranant P. Bioassay-guided isolation and evaluation of antimicrobial compound from Ixora megalophylla against some oral pathogens. Pharm. Biol. 2016; 54(9): 1522-27.
  • 13. Magano J, Chen MH, Clark JD, Nussbaumer T. 2-(Diethylamino)ethanethiol, a new reagent for the odorless deprotection of aromatic methyl ethers. J. Org. Chem. 2006; 71(18): 7103-5.
  • 14. Hayase H, Watanabe N, Lim CL, Nogawa T, Komatsuya K, Kita K, Osada H. Inhibition of Malaria Parasite Growth by Quinomycin A and its derivatives through DNA-Intercalating Activity. Biosci, Biotechnol, Biochem. 2015; 79(4): 633-5.
  • 15. Gamo FJ, Sanz LM, Vidal J, De Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF. Thousands of chemical starting points for antimalarial lead identification. Nature. 2010; 465(7296): 305-10.
  • 16. Vanichtanankul J, Taweechai S, Yuvaniyama J, Vilaivan T, P Chitnumsub, Kamchonwongpaisan S, Yuthavong Y. Trypanosomal Dihydrofolate Reductase Reveals Natural Antifolate Resistance. ACS. Chem. Biol. 2011; 6(9): 905-11.
  • 17. Matin MM, Hasan MS, Uzzaman M, Bhuiyan MMH, Kibria SM, Hossain ME, Roshid MHO. Synthesis, spectroscopic characterization, molecular docking, and ADMET studies of mannopyranoside esters as antimicrobial agents. J. Mol. Struct. 2020; 1222, 128821-33.
  • 18. Ahmad F, Ali M, Alam P. New phytoconstituents from the stem bark of Tinospora cordifolia Miers. Nat. Prod. Res. 2010;24(10): 926-34.
  • 19. Tian JK, Sun F, Cheng YY. Chemical constituents from the roots of Ranunculus ternatus. J. Asian Nat. Prod. Res. 2006; 8(1-2): 35-9.
  • 20. Vijayan N. Structural and optical characterization on solution grown methyl p-hydroxybenzoate single crystals. Indian J. Chem., Sect A. 2007; 46(1): 70-3.
  • 21. Tsai CY, Sung R, Zhuang BR, Sung KS. TiCl4 -activated selective nucleophilic substitution of tert-butyl alcohol and benzyl alcohol with p-donating substituents. Tetrahedron. 2010; 66(34): 6869-72.
  • 22. Kim H, Ralph J, Lu F, Boudet AM, MacKay JJ, Sederoff RR, Ito T, Kawai S, Ohashi H, Higuchi T. NMR analysis of lignins in CAD-deficient plants. Part 1. Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins. Org. Biomol. Chem. 2003; 1(2): 268-81.
There are 22 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Kok Tong Wong 0000-0003-4891-076X

Hasnah Osman This is me 0000-0001-8695-470X

Thaigarajan Parumasivam 0000-0001-6278-3627

Jafri Malin Abdullah This is me 0000-0002-0258-7410

Mohd. Zaheen Hassan 0000-0002-8235-5379

Mohamad Nurul Azmi Mohamad Taib 0000-0002-2447-0897

Project Number USM RUT grant (1001/PKIMIA/8011072)
Publication Date November 30, 2021
Submission Date March 28, 2021
Acceptance Date August 25, 2021
Published in Issue Year 2021

Cite

Vancouver Wong KT, Osman H, Parumasivam T, Abdullah JM, Hassan MZ, Mohamad Taib MNA. Antimalarial Evaluation of the Chemical Constituents Isolated from Dendrocalamus asper. JOTCSA. 2021;8(4):995-1002.