Structural Elucidation of Anti-Pseudomonas Component from Eucalyptus Tereticornis

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Authors

  • Department of Microbiology, Krupanidhi Degree College, Bengaluru - 560035 ,IN
  • Department of Biochemistry, Yenopoya Medical College, Yenepoya (Deemed to be University), Mangaluru - 575018 ,IN

DOI:

https://doi.org/10.18311/jnr/2023/31925

Keywords:

Eucalyptus tereticornis, Formylated Phloroglucinol Compounds (FPCs), High-Performance Liquid Chromatography (HPLC)

Abstract

Eucalyptus species is a well-known medicinal plant from ancient times with diverse biological functions, antimicrobial activity being one of them. This study attempts to isolate a secondary metabolite with antibacterial properties from ethanol extracts of Eucalyptus tereticornis leaf by antibacterial - against Pseudomonas aeruginosa - activity-guided procedure. Ethanol extract of the leaf powder was obtained by soxhlation and subjected to liquid-liquid extraction with organic solvents – ethyl acetate, n-hexane, n-butane, and chloroform. The active n-hexane and chloroform extracts were purified by column chromatography, and the components of the active eluant fraction were separated by Thin-layer chromatography (TLC). The purity of the antibacterial compound was checked by high performance liquid chromatography (HPLC), the molecular weight determined by Liquid chromatography-mass spectroscopy (LC-MS) and the structure elucidated and identified by nuclear magnetic resonance (NMR) and by Fourier transform infrared spectrometer (FTIR). TLC of n-hexane extract of liquid-liquid extraction showed a single spot with antibacterial activity. A single major peak was observed on HPLC, and LC-MS revealed that the compound is a formylated phloroglucinol component (FPC) with a molecular weight of 471.3. The NMR and FTIR analysis identified that the isolated compound is Macrocarpal A. This study reveals that the isolated relatively pure anti-Pseudomonas compound from the leaf extracts of E. tereticornis is Macrocarpal A, a flavanoid from FPC.

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Published

2023-03-23

How to Cite

S. Badrunissa, & Vinitha Ramanath Pai. (2023). Structural Elucidation of Anti-Pseudomonas Component from <i>Eucalyptus Tereticornis</i>. Journal of Natural Remedies, 23(1), 237–246. https://doi.org/10.18311/jnr/2023/31925

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References

Varadarajan Parivuguna, Rathinaswamy Gnanaprabhal, Rangasamy Dhanabalan and Asirvatahm Doss. Antimicrobial properties and phytochemical constituents of Rheodiscolor Hance. Ethanobotanical leaflets. 2008; 12:841-45.

Hariram V, Prakash R, Seralathan S and Premkumar TM. Exhaust Emission Reduction in a Single Cylinder Compression Ignition Engine Fuelled With Optimized Biodiesel Blends of Eucalyptus tereticornis. Nature Environment & Pollution Technology. 2019; 18(1).

Quereshi S, Upadhyay A, Singh R, Khan NA, Mani A and Patel J. GC analysis of essential oils, TLC profiling of pigments and DNA extraction from Eucalyptus species. Current Botany. 2011; 2(2).

Batista-Pereira LG, Fernandes JB, Correa AG, Silva MFGF and Vieira PC. Electrophysiological responses of eucalyptus brown looper Thyrinteina arnobia to essential oils of seven Eucalyptus species. Journal of the Brazilian Chemical Society. 2006; 17:555-561. https://doi.org/10.1590/S0103- 50532006000300019 DOI: https://doi.org/10.1590/S0103-50532006000300019

Zhang J, An M, Wu H, Stanton R and Lemerle D. Chemistry and bioactivity of Eucalyptus essential oils. Allelopathy Journal. 2010; 25(2):313-330.

Oyedeji AO, Olawore ON, Ekundayo O and Koenig WA. Volatile oil constituents of the eucalyptus viridis R.T Baker and Eucalyptus Oleosa. F. Muell. Leaves from Iran. Jmed. Plants. 1999; 895:105-108.

Syukri DM, Nwabor O and Ergantara RI. Preliminary phytochemical, antioxidants, and antibacterial properties of eucalyptus aqueous leaf extract against Streptococcus pyogenes. In IOP Conference Series: Earth and Environmental Science. IOP Publishing. 2019; 305(1):012067. https://doi. org/10.1088/1755-1315/305/1/012067 DOI: https://doi.org/10.1088/1755-1315/305/1/012067

Badrunnisa S, Shantaram M and Pai VR. Isolation, Characterization and Identification of bacteria from coolant oils. International journal of applied biology and pharmaceutical technology. 2011; 2(3):444-452.

Badrunnisa S, Pai VR and Shantaram M. Antibacterial activity of Eucalyptus tereticornis extracts for in use coolants of steel industry. Journal of Research in Pharmaceutical and Biomedical Sciences. 2011; 2(4):1789-94.

Harborne AJ. Phytochemical methods: A guide to modern techniques of plant analysis. London (UK): Chapman and Hall pub. 1998.

Oyugi DA, Luo X, Lee KS, Hill B and Izevbigie EB. Activity markers of the anti-breast carcinoma cell growth fractions of Vernonia amygdalina extracts. Experimental biology and medicine. 2009; 234(4):410-417. https://doi. org/10.3181/0811-RM-325 DOI: https://doi.org/10.3181/0811-RM-325

Dalal S, Goetz M, Cassera MB and Kingston DGI. Antiplasmodial phloroglucinol derivative isolated from Syncarpia glomulifera (Myrtaceae). Isolation and Structure Elucidation of Anticancer and Antimalarial Natural Products. 2016; 37.

Martos I, Ferreres F and Tomas Barberan FA. Identification of flavonoid markers for the botanical origin of Eucalyptus honey. Journal of Agricultural and Food Chemistry. 2000; 48(5):1498-1502. https://doi.org/10.1021/jf991166q DOI: https://doi.org/10.1021/jf991166q

Martos I, Ferreres F, Yao L, D’Arcy B, Caffin N and Tomas Barberan FA. Flavonoids in monospecific Eucalyptus honeys from Australia. Journal of Agricultural and Food Chemistry. 2000; 48(10):4744-4748. https://doi.org/10.1021/jf000277i DOI: https://doi.org/10.1021/jf000277i

Eyles A, Davies NW and Mohammed C. Novel Detection of Formylated Phloroglucinol Compounds (FPCs) in the Wound Wood of Eucalyptus globulus and E. nitens. Journal of chemical ecology. 2003; 29(4):881-898. https://doi. org/10.1023/A:1022979632281 DOI: https://doi.org/10.1023/A:1022979632281

Tomas-Barberan FA, Garcia-Viguera C, Vit-Olivier P, Ferreres Fand Tomas-Lorente F. Phytochemical evidence for the botanical origin of tropical propolis from Venezuela. Phytochemistry. 1993; 34(1):191-196. https:// doi.org/10.1016/S0031-9422(00)90804-5 DOI: https://doi.org/10.1016/S0031-9422(00)90804-5

Yao L, Datta N, Tomas-Barberan FA, Ferreres F, Martos I and Singanusong R. . Flavonoids, phenolic acids and abscisic acid in Australian and New Zealand Leptospermum honeys. Food Chemistry. 2003; 81(2):159-168. https://doi. org/10.1016/S0308-8146(02)00388-6 DOI: https://doi.org/10.1016/S0308-8146(02)00388-6

Luo X, Duan Y, Yang W, Zhang H, Li C and Zhang J. Structural elucidation and immunostimulatory activity of polysaccharide isolated by subcritical water extraction from Cordyceps militaris. Carbohydrate polymers. 2017; 157:794- 802. https://doi.org/10.1016/j.carbpol.2016.10.066 DOI: https://doi.org/10.1016/j.carbpol.2016.10.066

Osawa K, Yasuda H, Morita H, Takeya K and Itokawa H. Configuraitonal and conformational analysis of Macrocarpals H, I, and J from Eucalyptus globulus. Chemical and pharmaceutical bulletin. 1997; 45(7):1216- 1217. https://doi.org/10.1248/cpb.45.1216 DOI: https://doi.org/10.1248/cpb.45.1216

Wojcicki J, Barcew-Wiszniewska B, Samochowiec L and Rozewicka L. Extractum Fagopyri reduces atherosclerosis in high-fat diet fed rabbits. Die Pharmazie. 1995; 50(8):560- 562.

Xu SH, Xu W, Wang L, Hu YK, Liu JP, Zhao Y, Li MJ, Li F, Huang SX and Zhao Y. New phloroglucinol derivatives with protein tyrosine phosphatase 1B (PTP1B) inhibitory activities from Syzygium austroyunnanense. Fitoterapia. 2018; 131:141-145. https://doi.org/10.1016/j.fitote.2018.10.010 DOI: https://doi.org/10.1016/j.fitote.2018.10.010

Kreft I, Fabjan N and Yasumoto K. Rutin content in buckwheat (Fagopyrum esculentum Moench) food materials and products. Food chemistry. 2006; 98(3):508-512. https://doi. org/10.1016/j.foodchem.2005.05.081 DOI: https://doi.org/10.1016/j.foodchem.2005.05.081

Yasar A, Ucuncu O, Gulec C, Inceer H, Ayaz S and Yayl N. GC-MS Analysis of Chloroform Extracts in Flowers, Stems, and Roots of Tripleurospermum callosum. Pharmaceutical biology. 2005; 43(2):108-112. https://doi. org/10.1080/13880200590919384 DOI: https://doi.org/10.1080/13880200590919384

Arima H and Danno GI. Isolation of antimicrobial compounds from guava (Psidium guajava L.) and their structural elucidation. Bioscience, biotechnology, and biochemistry. 2002; 66(8):1727-1730. https://doi.org/10.1271/ bbb.66.1727 DOI: https://doi.org/10.1271/bbb.66.1727

Nagpal N, Shah G, Arora NM, Shri R and Arya Y. Phytochemical and pharmacological aspects of Eucalyptus genus. International Journal of Pharmaceutical Sciences and Research (IJPSR). 2010; 1(12):28-36.

Dilber SP, Dobric SL, Juranic ZD, Markovic BD, Vladimirov SM and Juranic IO. Docking Studies and Anti-inflammatory Activity of β-Hydroxy-β-arylpropanoic Acids. Molecules. 2008; 13(3):603-615. https://doi.org/10.3390/molecules13030603 DOI: https://doi.org/10.3390/molecules13030603

Muhit MA, Tareq SM, Apu AS, Basak D and Islam MS. Isolation and identification of compounds from the leaf extract of Dillenia indica Linn. Bangladesh Pharmaceutical Journal. 2010; 13(1):49-53.

Khan R, Khare P, Baruah BP, Hazarika AK and Dey NC. Spectroscopic, kinetic studies of polyaniline-flyash composite. Advances in chemical engineering and sciences. 2011; 1:37-44. https://doi.org/10.4236/aces.2011.12007 DOI: https://doi.org/10.4236/aces.2011.12007

Griffin GW, Quach HT and Steeper RL. Extraction and thin layer chromatography of chlorophyll A and B from Spinach. Journal of Chemical Education. 2004; 81:385-387. https:// doi.org/10.1021/ed081p385 DOI: https://doi.org/10.1021/ed081p385

Hardel DK and Laxmidhar S. A review on phytochemical and pharmacological of Eucalyptus globulus: a multipurpose tree. International Journal of Research in Ayurveda and Pharmacy (IJRAP). 2011; 2(5):1527-1530.

Close DC, Davies NW and Beadle CL. Temporal variation of tannins (galloylglucoses), flavonols and anthocyanins in leaves of Eucalyptus nitens seedlings: implications for light attenuation and antioxidant activities. Functional Plant Biology. 2001; 28(4):269-278. https://doi.org/10.1071/ PP00112 DOI: https://doi.org/10.1071/PP00112

Shang ZC, Han C, Xu JL, Liu RH, Yin Y, Wang XB, YangMH and Kong LY. Twelve formyl phloroglucinol meroterpenoids from the leaves of Eucalyptus robusta. Phytochemistry. 2019; 163:111-117. https://doi.org/10.1016/j.phytochem.2019.04.008 DOI: https://doi.org/10.1016/j.phytochem.2019.04.008

Ghisalberti EL. Bioactive acylphloroglucinol derivatives from Eucalyptus species. Phytochemistry. 1996; 41(1):7-22. https://doi.org/10.1016/0031-9422(95)00484-X DOI: https://doi.org/10.1016/0031-9422(95)00484-X

Murata M, Yamakoshi Y, Homma S, Arai K and Nakamura Y. Macrocarpals, antibacterial compounds from Eucalyptus, inhibit aldose reductase. Bioscience, biotechnology, and biochemistry. 1992; 56(12):2062-2063. https://doi. org/10.1271/bbb.56.2062 DOI: https://doi.org/10.1271/bbb.56.2062

Singh IP and Etoh HG. Biological activities of phloroglucocinol derivatives from Eucalyptus species. Nat. Prod. Sci. 1997; 30:1-7.

Eschler BM, Pass DM, Willis R and Foley WJ. Distribution of foliar formylated phloroglucinol derivatives amongst Eucalyptus species. Biochemical Systematics and Ecology. 2000; 28(9):813-824. https://doi.org/10.1016/S0305- 1978(99)00123-4 DOI: https://doi.org/10.1016/S0305-1978(99)00123-4

Pham TA, Shair Mohammad I, Vu VT, Hu XL, Birendra C, Ulah A, Guo C, Lu XY, Ye WC and Wang H. Phloroglucinol derivatives from the fruits of Eucalyptus globulus and their cytotoxic activities. Chemistry and biodiversity. 2018; 15(6):e1800052. https://doi.org/10.1002/cbdv.201800052 DOI: https://doi.org/10.1002/cbdv.201800052

Nishizawa M, Emura M, Kan Y, Yamada H, Ogawa K and Hamanaka N. Macrocarpals: HIV-RTase inhibitors of Eucalyptus globulus. Tetrahedron letters. 1992; 33(21):2983- 2986. https://doi.org/10.1016/S0040-4039(00)79578-5 DOI: https://doi.org/10.1016/S0040-4039(00)79578-5

Van Doorslaer S, Dedonder A, de Blocks M and Callens F. Oxidative stress in plants: EPR monitoring in DMPODMSO based extracts. Journal of Plant Physiology. 1999; 154(1):132-136. https://doi.org/10.1016/S0176- 1617(99)80329-0 DOI: https://doi.org/10.1016/S0176-1617(99)80329-0

Liu B, Marques dos Santos B, Kanagendran A, Neilson EHJ and Niinemets U. Ozone and wounding stresses differently alter the temporal variation in formylated phloroglucinols in Eucalyptus globulus leaves. Metabolites. 2019; 9(3):46. https://doi.org/10.3390/metabo9030046 DOI: https://doi.org/10.3390/metabo9030046