Quantum chemical calculations of lupeol (C30H50O) isolated from the ethyl acetate leaf extracts of Justicia Secunda

B. Bako; E. E. Etim; J. P. Shinggu; S. S. Humphrey; L. J. Moses; M. E. Khan

doi:10.46481/jnsps.2024.1995

Authors

B. Bako
Computational, Astrochemistry and Bio-simulation Research Group, Federal University Wukari, Wukari, Nigeria
E. E. Etim
[email protected]

Computational, Astrochemistry and Bio-simulation Research Group, Federal University Wukari, Wukari, Nigeria
J. P. Shinggu
Computational, Astrochemistry and Bio-simulation Research Group, Federal University Wukari, Wukari, Nigeria
S. S. Humphrey
Computational, Astrochemistry and Bio-simulation Research Group, Federal University Wukari, Wukari, Nigeria
L. J. Moses
Computational, Astrochemistry and Bio-simulation Research Group, Federal University Wukari, Wukari, Nigeria
M. E. Khan
Department of Chemistry, Federal University Lokoja, Kogi, Nigeri

Keywords:

Justicia secunda, Lupeol, Quantum chemical Calculations

Abstract

The discovery of lupeol, a triterpenoid compound (C30H50O), in the ethyl acetate leaf extract of Justicia secunda (Blood root), has opened doors to extensive research and development opportunities in natural product-based pharmaceuticals. Lupeol’s versatile pharmacological properties, including anti-inflammatory, anticancer, antidiabetic, and antiviral effects, make it a compelling candidate for drug development. To fully harness its potential, a comprehensive understanding of lupeol’s structural and chemical attributes is crucial. Through quantum chemical calculations using the GAUSSIAN 09 suite of programs, we determined the optimized geometry, IR frequencies, bond distances (R), bond angles (A), dipole moments, HOMO-LUMO and other molecular parameters for this solitary molecule. The remarkable accuracy and reliability of computational techniques in predicting the properties of systems and reactants are evident in the consistently favorable results. A strong concordance and consistency between the experimental and computational outcomes further reinforces the credibility of our findings. This study offers a means to explore lupeol’s molecular behavior, providing insights that can guide future drug development efforts rooted in this promising natural compound.

Dimensions

REFERENCES

M. Lahlou, “Screening of natural products for drug discovery”, Expert opinion on drug discovery 2 (2007) 697. https://www.tandfonline.com/doi/abs/10.1517/17460441.2.5.697.

E. Marsault & M. L. Peterson, “Macrocycles are great cycles: applications, opportunities, and challenges of synthetic macrocycles in drug discovery”, Journal of medicinal chemistry 54 (2011) 1961. https://pubs.acs.org/doi/full/10.1021/jm1012374.

C. Drahl, B. F. Cravatt & E. J. Sorensen, “Protein-reactive natural products”, Angewandte Chemie International Edition 44 (2005) 5788. https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.200500900.

O. A. Ushie, A. C. Kendeson, B. D. Longbab, P. U. Ogofotha, S. T. Nongu, & B. Bako, “Profiling phytochemicals and antimicrobial activities of hexane and acetone crude extracts of sterculia setigera leaf”, Journal of Chemical Society of Nigeria 47 (2022). https://www.journals.chemsociety.org.ng/index.php/jcsn/article/view/827.

C. O. Keke, L. A. Nwaogu, C. U. Igwe, K. L. Ekeke, & W. N. Nsofor, “Phytochemical and nutritional composition of ethanol-water leaf extracts of Justicia secunda and Jatropha tanjorensis”, GSC Biological and Pharmaceutical Sciences 23 (2023) 042. https://oa.mg/work/10.5281/zenodo.8260308.

T. D. Locklear, Biologically active compounds from justicia pectoralis: Significance for the treatment of dysmenorrhea, University of Illinois at Chicago, Health Sciences Center, 2008. https://www.proquest.com/openview/e891dad92bf7edd57099372dd5ab30f5/1?pq-origsite=gscholar&cbl=18750.

M. G. Ajuru, K. A. Kpekot, G. E. Robinson & M. C. Amutadi, “Proximate and phytochemical analysis of the leaves of Justicia carnea Lindi. and Justicia secunda Vahl and its taxonomic implications”, J. Biomed.

Biosens 2 (2022) 1. https://gpub.org/article-details.php?article-id=58.

J. M. Kitadi, E. M. Lengbiye, B. Z. Gbolo, C. L. Inkoto, C. L. Muanyishay, G. L. Lufuluabo, D. S. Tshibangu, D. D. Tshilanda, B. M. Mbala, K. Ngbolua & P. T. Mpiana, “Justicia secunda Vahl species: Phytochemistry, Pharmacology and Future Directions: a mini-review”, Discovery Phytomedicine 6 (2019) 157. https://biology.ejournals.ca/ejournals/phytomedicine.ejournals.ca/index.php/phytomedicine/article/view/93.

A. E. Ayodele, O. I. Odusole, & A. O. Adekanmbi, “Phytochemical screening and in-vitro antibacterial activity of leaf extracts of Justicia secunda Vahl on selected clinical pathogens”, MicroMedicine 8 (2020)

https://www.journals.tmkarpinski.com/index.php/mmed/article/view/275.

B. Bako, “Applications of Justicia secunda Extracts in Functional Foods and Natural Products: A Review”, Advanced Journal of Chemistry Section B 6 (2024) 1. https://www.ajchem-b.com/article_182234.html.

B. Bako, O. A. Ushie & S. P. Malu, “Lupeol and Lauric Acid Isolated from Ethyl Acetate Stem Extract of Justicia secunda and Their Antimi crobial Activity”, Journal of Chemical Society of Nigeria 48 (2023) 81. https://journals.chemsociety.org.ng/index.php/jcsn/article/view/852.

F. A. Mac´?as, F. J. Mej´?as & J. M. Molinillo, “Recent advances in allelopathy for weed control: From knowledge to applications”, Pest management science 75 (2019) 2413. https://scijournals.onlinelibrary.wiley.com/doi/abs/10.1002/ps.5355.

M. Zhou, R. H. Zhang, M. Wang, G. B. Xu & S. G. Liao, “Prodrugs of triterpenoids and their derivatives”, European Journal of Medicinal Chemistry 131 (2017) 222. https://www.sciencedirect.com/science/article/abs/pii/S022352341730154X.

N. Zullkiflee, H. Taha & A. Usman, “Propolis: Its role and efficacy in human health and diseases”, Molecules 27 (2022) 6120. https://www.mdpi.com/1420-3049/27/18/6120.

A. Senthilkumar, N. Karuvantevida, L. Rastrelli, S. S. Kurup & A. J. Cheruth, “Traditional uses, pharmacological efficacy, and phytochemistry of Moringa peregrina (Forssk.) Fiori.—a review”, Frontiers in pharmacology 9 (2018) 465. https://www.frontiersin.org/journals/pharmacology/articles/10.3389/fphar.2018.00465/full.

A. Alam, S. Ferdosh, K. Ghafoor, A. Hakim, A. S. Juraimi, A. Khatib & Z. I. Sarker, “Clinacanthus nutans: A review of the medicinal uses, pharmacology and phytochemistry”, Asian Pacific journal of tropical medicine 9 (2016) 402. https://www.sciencedirect.com/science/article/pii/S1995764516300116.

J. A. Keith, V. Vassilev-Galindo, B. Cheng, S. Chmiela, M. Gastegger, K. R. Mu¨ller & A. Tkatchenko, “Combining machine learning and computational chemistry for predictive insights into chemical systems”, Chemical reviews 121 (2021) 9816. https://pubs.acs.org/doi/full/10.1021/acs.chemrev.1c00107.

G. O. Izuagbe, E. O. Emmanuella, L. Hitler, M. K. Emmanuel, E. E. Emmanuel, O. E. Henry, J. I. Onyinye, P. O. Amoawe & O. Faith, “Antibacterial potential of N-(2-furylmethylidene)-1, 3, 4-thiadiazole-2-amine: Experimental and theoretical investigations”, Journal of the Indian Chemical Society 99 (2022) 100597. https://www.sciencedirect.com/science/article/abs/pii/S001945222200259X.

E. G. Lewars, Computational chemistry: Introduction to the theory and applications of molecular and quantum mechanics, Springer Cham, 2011, pp. 318–728. https://link.springer.com/book/10.1007/978-3-319-30916-3.

M. Biczysko, J. Bloino, G. Brancato, I. Cacelli, C. Cappelli, A. Ferretti, A. Lami, S. Monti, A. Pedone, G. Prampolini, C. Puzzarini, F. Santoro, F. Trani & G. Villani, “Integrated computational approaches for spectroscopic studies of molecular systems in the gas phase and in solution: pyrimidine as a test case”, Theoretical Chemistry Accounts 131 (2012) 1.

https://link.springer.com/article/10.1007/s00214-012-1201-3.

G. O. Izuagbe, L. Hitler, M. K. Emmanuel, E. E. Emmanuel, E. O. Emmanuella, P. O. Amoawe, O. E. Henry & O. Faith, “Antibacterial Potential of 2-(-(2-Hydroxyphenyl)-methylidene)-amino)nicotinic Acid:

Experimental, DFT Studies, and Molecular Docking Approach”, Appl Biochem Biotechnol 194 (2022) 5680. https://link.springer.com/article/10.1007/s12010-022-04054-9.

Y. Ma, J. Xiong, P. Zhang, Y. Li, S. Zhang, Z. Wang, L. Xu, H. Guo, K.Chen & Y. Wei, “Recent Progress on Density Functional Theory Calcu lations for Catalytic Control of Air Pollution”, ACS ES&T Engineering 4 (2023) 47. https://pubs.acs.org/doi/abs/10.1021/acsestengg.3c00208.

J. S. Costa, C. B. R. D. Santos, K. S. L. Costa, R. D. S. Ramos, C. H. T. D. P. D. Silva & W. J. D. C. Macedo, “Validation of computational methods applied in molecular modeling of caffeine with epithelial anticancer activity: Theoretical study of geometric, thermochemical and spectrometric data”, Qu´?mica Nova 41 (2018) 553. https://www.scielo.br/j/qn/a/6L6hSvdgT7yZFxsbPs4gwnD/?format=html&lang=en.

M. E. Khan, E. E. Etim, V. J. Anyam, A. Abel, I. G. Osigbemhe, & C. T. Agber, “Computational studies on Emodin (C15H10O5) from Methanol extract of Pteridium acquilinum leaves”, J. Nig. Soc. Phys. Sci. 3 (2021) 360. https://www.journal.nsps.org.ng/index.php/jnsps/article/view/301.

I. G. Osigbemhe, H. Louis, E. M. Khan, E. E. Etim, D. O. Odey, A. P. Oviawe, H. O. Edet & F. Obuye, “Synthesis, characterization, DFT studies, and molecular modeling of 2-(-(2-hydroxy-5-methoxyphenyl)-methylidene)-amino) nicotinic acid against some selected bacterial receptors”, Journal of the Iranian Chemical Society 19 (2022) 3561. https://link.springer.com/article/10.1007/s13738-022-02550-7.

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayash, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski & D. J. Fox, “Gaussian 09, Revision D. 01, Gaussian”, Inc. Wallingford CT (2009). https://cir.nii.ac.jp/crid/1370298757422456580.

E. E. Etim, A. I. Onen, C. Andrew, U. Lawal, I. S. Udegbunam & O. A. Ushie, “Computational Studies of C5H5N Isomers”, Journal of Chemical Society of Nigeria, 43 (2018). https://journals.chemsociety.org.ng/index.php/jcsn/article/view/154.

C. Andrew, E. E. Etim, O. A. Ushie & G. P. Khanal, “Vibrational Rotational Spectra of Normal Acetylene and Doubly Deuterated Acetylene: Experimental and Computational Studies”, Chemical Science 7 (2018) 77. chrome-extension://efaidnbmnnnibpcajpcglclefindmkaj/http://www.e-journals.in/pdf/V7N1/77-82.pdf.

E. E. Etim, G. E. Oko, A. I. Onen, O. A. Ushie, U. Lawal & G. P. Khanal, “Computational Studies of Sulphur trioxide (SO3) and its protonated analogues”, Journal of Chemical Society of Nigeria 43 (2018).

https://journals.chemsociety.org.ng/index.php/jcsn/article/view/153.

E. E. Etim, B. S. Abah, I. E. Mbakara, E. J. Inyang & O. P. Ukafia, “Quantum Chemical Calculations on Silicon Monoxide (SiO) and its Protonated Analogues”, Tropical Journal of Applied Natural

Sciences 2 (2017) 61. https://www.researchgate.net/publication/330555369_Quantum_Chemical_Calculations_on_Silicon_Monoxide_SiO_and_its_Protonated_Analogues.

E. E. Etim, S. A. Olagboye, O. E. Godwin & I. M. Atiatah, “Quantum Chemical studies on Silicon tetrafluoride and its protonated analogues”, International Journal of Modern Chemistry 12 (2020) 26. chrome-extension://efaidnbmnnnibpcajpcglclefindmkaj/ https://www.researchgate.net/profile/Oko-Emmanuel-Godwin-2/publication/347553285_Share_’2020SiF4_Published_paper/links/5fe1a9a192851c13fead9027/Share-2020-SiF4-Published-paper.pdf.

E. E. Etim, E. Oko, Godwin, I. F. Sambo & S. A. Olagboye, “Quantum Chemical Studies on Furan and Its Isomers”, International Journal of Modern Chemistry 12 (2020) 77. chrome-extension://efaidnbmnnnibpcajpcglclefindmkaj/https://www.researchgate.net/profile/Oko-Emmanuel-Godwin-2/publication/347553041_Quantum_Chemical_studies_of_Furan/links/5fe1a94b45851553a0df5889/Quantum-Chemical-studies-of-Furan.pdf.

E. E. Etim, G. E. Oko, A. I. Onen, O. A. Ushie, C. Andrew, U. Lawal & G. P. Khanal, “Computational Studies of Sulphur Trioxide (SO3) and its Protonated Analogues”, J. Chem Soc. Nigeria 43 (2018) 10. https://journals.chemsociety.org.ng/index.php/jcsn/article/view/153.

E. E. Etim, B. S. Abah, I. E. Mbakara, E. J. Inyang, O. P. Ukafia, “Quantum Chemical Calculations on Silicon Monoxide (SiO) and its Protonated Analogues”, Trop. J. Appl. Nat. Sci. 2 (2017) 61. https://www.researchgate.net/publication/330555369_Quantum_Chemical_Calculations_on_Silicon_Monoxide_SiO_and_its_Protonated_Analogues.

J. P. Shinggu, E. E. Etim, & A. I. Onen, “Quantum Chemical Studies on C2H2O Isomeric Species: Astrophysical Implications, and Com parison of Methods”, Communication in Physical Sciences 9 (2023).

https://journalcps.com/index.php/volumes/article/view/349.

J. P. Shinggu, E. E. Etim & A. I. Onen, “Protonation-Induced Structural and Spectroscopic Variations in Molecular Species: A Computational Study on N2, H2, CO, CS, and PH3”, Communication in Physical Sciences 9 (2023). https://journalcps.com/index.php/volumes/article/view/388.

J. P. Shinggu, E. E. Etim & A. I. Onen, “Isotopic Effects on the Structure and Spectroscopy of Thioformaldehyde, Dihydrogen and Water”, Advanced. Journal of Chemistry. A 6 (2023) 366. https://www.ajchem-a.com/article 178011.html.

E. E. Etim, E. G. Oko, I. Fridy & A. Olagboye, “Quantum Chemical Studies on Furan and Its Isomers”, International Journal of Mod ern Chemistry 12 (2020) 77. https://www.researchgate.net/publication/347553041_Quantum_Chemical_studies_of_Furan.

D. Alahira, J. P. Shinggu & B. Bako, “Quantum chemical and molecular docking studies of luteolin and naringerin found in tigernut: A study of their anti-cancer properties”, Journal of Medicinal and Nanomaterials Chemistry 6 (2024) 64. chrome-extension://efaidnbmnnnibpcajpcglclefindmkaj/https://jmnc.samipubco.com/article_1941154eada3e6dc19ae7a70a8946cd686ae36.pdf.

O. A. Ushie, E. E Etim, A. I. Onen, C. Andrew, U. Lawal & G. P. Khanal, “Computational Studies of ?-amyrin acetate (C32H52O2) Detected in Methanol Leaf Extract of Chrysophyllum albidium”, Journal of Chemical Society of Nigeria 44 (2019) 561. https://www.journals.chemsociety.org.ng/index.php/jcsn/article/view/305.

I. Jantan, S. N. A. Bukhari, M. A. S. Mohamed, L. K. Wai & M. A. Mesaik, “The evolving role of natural products from the tropical rain forests as a replenishable source of new drug leads”, Drug Discovery and Development-From Molecules to Medicine (2015) 3. https://www.intechopen.com/chapters/47844.

M. E. Khan, C. E. Elum, A. O. Ijeomah, P. J. Ameji, I. G. Osigbemhe, E. E. Etim, J. V. Anyam, A. Abel, & C. T. Agber, “Isolation, Characterization, Antimicrobial and Theoretical Investigation of Some Bioactive Compounds Obtained from the Bulbs of Calotropisprocera”, Journal of the Nigerian Society of Physical Sciences 5 (2023) 1576. https://doi.org/10.46481/jnsps.2023.1576.

I. G. Osigbemhe, E. E. Oyoita, H. Louis, E. M. Khan, E. E. Etim, H. O. Edet, O. J. Ikenyirimba, A. P. Oviawe & F. Obuye, “Antibacterial potential of N-(2-furylmethylidene)-1, 3, 4-thiadiazole-2-amine: Experimental and theoretical investigations”, Journal of Molecular Structure 1253 (2023) 131408. https://www.sciencedirect.com/science/article/abs/pii/S001945222200259X.

E. G. Oko, A. E. Peter & E. E. Emmanuel, “Phytochemical and Antimicrobial Properties of African Peach (Sarcocephalus Latifolius)”, Organic & Medicinal Chem IJ. 9 (2020) 555775. https://ideas.repec.org/a/adp/jomcij/v9y2020i5p198-204.html.

E. E. Etim, J. E. Asuquo, O. C. Ngana & G. O. Ogofotha, “Investigation on the thermochemistry, molecular spectroscopy and structural parameters of pyrrole and its isomers: a quantum chemistry approach”, Journal of Chemical Society of Nigeria 47 (2022). https://journals.chemsociety.org.ng/index.php/jcsn/article/view/704.

E. E. Etim, M. E. Khan, O. E. Godwin & G. O. Ogofotha, “Quan tum Chemical Studies on C4H4N2 Isomeric Molecular Species”, Journal of the Nigerian Society of Physical Sciences (2021) 429. https://www.journal.nsps.org.ng/index.php/jnsps/article/view/282.

E. E. Etim, E. G. Oko, I. F. Sambo & S. Adeoye, “Suspected Error in Some Experimentally Reported Proton Affinity Values: Insight from Quantum Chemical Calculations”, Int. J. Modern Anal.

Sep. Sci, 8(1) (2020) 28. https://www.researchgate.net/publication/347551664_Suspected_Error_in_Some_Experimentally__Reported_Proton_Affinity_Values_Insight_from_Quantum_Chemical_Calculations.

E. E. Etim, S. A. Olagboye, O. E. Godwin & I. M. Atiatah, “Quantum Chemical studies on Silicon tetrafluoride and its protonated analogues”, Int. J. Modern Chem 12 (2020) 26. https://www.researchgate.net/publication/347553285_Share_%272020_SiF4_Published_paper.

A. I. Onen, J. Joseph, E. Etim & N. O. Eddy, “Quantum Chemical Studies on the Inhibition Mechanism of Ficus carica, FC and Vitellaria paradoxa, VP Leaf Extracts”, Journal of Advanced Chemical Sciences 3 (2017) 496. https://www.semanticscholar.org/paper/Quantum-Chemical-Studies-on-the-Inhibition-of-Ficus-Onen-Joseph/be9a0dfc0a1e07a733793a8574adda0a17be0cb5.