Characterization of pharmacological properties and isolation of two bioactive compounds (ursolic acid and palmitoleic acid) from the stem bark extract of Lannea coromandelica

Subject Areas : Phytochemistry: Isolation, Purification, Characterization

Ramisa Anjum ¹ , A.H.M. Nazmul Hasan ² , Mst. Al Asma Hawa ³ , Md. Naimur Rahman ⁴ , Md. Khokon Miah Akanda ⁵ , Tania Binte Wahed ⁶ , Fayad Bin Abdus Salam ⁷ , Md. Rabiul Islam ⁸ , Mohammad Shahriar ⁹

1 - Department of Pharmacy, University of Asia Pacific, 74/A Green Road, Farmgate, Dhaka 1205, Bangladesh
2 - Department of Pharmacy, School of Medicine, University of Asia Pacific, Dhaka, Bangladesh
3 - Department of Pharmacy, University of Asia Pacific, 74/A Green Road, Farmgate, Dhaka 1205, Bangladesh
4 - Department of Pharmacy, University of Asia Pacific, 74/A Green Road, Farmgate, Dhaka 1205, Bangladesh
5 - Department of Pharmacy, University of Asia Pacific, 74/A Green Road, Farmgate, Dhaka 1205, Bangladesh
6 - Department of Pharmacy, Jahangirnagar University, Savar, Dhaka-1342, Bangladesh
7 - Pharmacy Discipline, Khulna University, Khulna 9208, Bangladesh
8 - School of Pharmacy, BRAC University, Kha 224, Bir Uttam Rafiqul Islam Avenue, Merul Badda, Dhaka 1212, Bangladesh
9 - Department of Pharmacy, University of Asia Pacific, 74/A Green Road, Farmgate, Dhaka 1205, Bangladesh

Received: 2024-01-13 Accepted : 2024-06-15 Published : 2024-09-21

Keywords: Antidiabetic, Antioxidants, Bioactive compound isolation, Lanna coromendelica, Palmitoleic acid, Ursolic acid,

Abstract :

The current research aimed to conduct a bioassay-guided isolation of bioactive compounds from the stem bark of Lannea coromandelica. Using column chromatography and NMR spectroscopy, two compounds -ursolic acid and palmitoleic acid- were isolated from the plant’s stem bark. The methanolic stem bark extract possessed higher total phenolic, flavonoid, and antioxidant capacity content than the n-hexane extract. The IC50 value of the methanol and n-hexane stem bark extracts for DPPH free radical scavenging potential was found to be 37.37 and 27.726 μg/mL, respectively, while for nitric oxide, the IC50 value was 14.615 and 22.136 μg/mL, respectively. The n-hexane extract exhibited higher antidiabetic effectiveness (46% blood glucose reduction) than the methanolic extract (37.8% blood glucose reduction) after 3 hours of glucose administration in mice model at a dose of 400 mg/kg body weight (p < 0.001). The methanolic extract demonstrated the highest anti-diarrheal action at a dose of 400 mg/kg body weight (88.70% inhibition of defecation, p < 0.001). Furthermore, the n-hexane extract showed the highest analgesic activity (70.5% inhibition of writhing, p < 0.01).

References:

Akanda, M.K.M., Hasan, A.N., 2021. Characterization of pharmacological properties of methanolic seed and stem bark extracts of Ziziphus mauritiana (BAU Kul) using in-vitro and in-vivo animal (Swiss albino male mice) model. Clin. Phytosci. 7, 1-13.
Alam, M.B., Kwon, K.R., Lee, S.H., Lee, S.H., 2017. Lannea coromandelica (Houtt.) Merr. induces heme oxygenase 1 (ho-1) expression and reduces oxidative stress via the p38/c-jun n-terminal kinase-nuclear factor erythroid 2-related factor 2 (p38/jnk-nrf2)-mediated antioxidant pathway. Int. J. Mol. Sci. 18(2), 266.
Amabeoku, G., 2009. Antidiarrhoeal activity of Geranium incanum Burm. f. (Geraniaceae) leaf aqueous extract in mice. J. Ethnopharmacol. 123, 190-193.
American Diabetes Association, 2010. Diagnosis and classification of diabetes mellitus. Diabetes care, 33(Supplement_1), S62-S69.
Araújo, T.S., Costa, D.S., Sousa, N.A., Souza, L.K., De Araújo, S., Oliveira, A.P., Sousa, F.B.M., Silva, D.A., Barbosa, A.L., Leite, J.R.S., 2015. Antidiarrheal activity of cashew GUM, a complex heteropolysaccharide extracted from exudate of Anacardium occidentale L. in rodents. J. Ethnopharmacol. 174, 299-307.
Aziz, I., Saqib, Q.N., Younus, M., Ali, E., Qadir, M.I., Siddique, F.A., Wazir, M.A., Shaheer, M. T., Adnan, Q., Shirazi, J.H., 2021. Physicochemical, antidiarrheal and antidiabetic potential of super food (Moringa oleifera Lam.). Pak. J. Pharm. Sci. 34, 723-729.
Bao, J., Cai, Y., Sun, M., Wang, G., Corke, H., 2005. Anthocyanins, flavonols, and free radical scavenging activity of Chinese bayberry (Myrica rubra) extracts and their color properties and stability. J. Agric. Food. Chem. 53, 2327-2332.
Bauer, A., Kirby, W., Sherris, J.C., Turck, M., 1966. Antibiotic susceptibility testing by a standardized single disk method. Am. J. Clin. Pathol. 45, 493-496.
Bermúdez, M.A., Pereira, L., Fraile, C., Valerio, L., Balboa, M.A., Balsinde, J., 2022. Roles of palmitoleic acid and its positional isomers, hypogeic and sapienic acids, in inflammation, metabolic diseases and cancer. Cells 11, 2146.
Choi, H.Y., Jhun, E.J., Lim, B.O., Chung, I.M., Kyung, S.H., Park, D.K., 2000. Application of flow injection-chemiluminescence to the study of radical scavenging activity in plants. Phytother. Res. 14, 250-253.
Coskun, O., 2016. Separation techniques: Chromatography. North. Clin. Istanb. 3, 156.
Davis, J.M., Murphy, E.A., Carmichael, M.D. 2009. Effects of the dietary flavonoid quercetin upon performance and health. Curr. Sports Med. Rep. 8, 206-213.
Gupta, M., Mazumder, U., Kumar, R.S., Gomathi, P., Rajeshwar, Y., Kakoti, B., Selven, V.T., 2005. Anti-inflammatory, analgesic, and antipyretic effects of methanol extract from Bauhinia racemosa stem bark in animal models. J. Ethnopharmacol. 98, 267-273.
Haenen, G.R., Bast, A., 1999. Nitric oxide radical scavenging of flavonoids. Methods Enzymol. 301, 490-503.
Harbertson, J.F., Spayd, S., 2006. Measuring phenolics in the winery. Am. J. Enol. Vitic. 57, 280-288.
Islam, F., Mitra, S., Nafady, M.H., Rahman, M.T., Tirth, V., Akter, A., Emran, T.B., Mohamed, A. A.R., Algahtani, A., El-Kholy, S.S., 2022. Neuropharmacological and antidiabetic potential of Lannea coromandelica (Houtt.) Merr. leaves extract: An experimental analysis. J. Evid. Based Complementary. Altern. Med. 2022.
Islam, M.T., Ito, T., Sakasai, M., Tahara, S., 2002. Zoosporicidal activity of polyflavonoid tannin identified in Lannea coromandelica stem bark against phytopathogenic oomycete Aphanomyces cochlioides. J. Agric. Food. Chem. 50, 6697-703.
Jabri, M.A., Rtibi, K., Ben-Said, A., Aouadhi, C., Hosni, K., Sakly, M., Sebai, H., 2016. Antidiarrhoeal, antimicrobial and antioxidant effects of myrtle berries (Myrtus co mmunis L.) seeds extract. J. Pharm. Pharmacol. 68, 264-274.
Kaur, R., Jaiswal, M.L., Jain, V., 2013. Protective effect of Lannea coromandelica Houtt. Merrill. against three co mmon pathogens. J. Ayurveda. Integr. Med. 4, 224-228.
Kedare, S.B., Singh, R., 2011. Genesis and development of DPPH method of antioxidant assay. J. Food. Sci. Technol. 48, 412-422.
Khwaza, V., Oyedeji, O.O., Aderibigbe, B.A., 2020. Ursolic acid-based derivatives as potential anti-cancer agents: An update. Int. J. Mol. Sci. 21, 5920.
Knothe, G., Kenar, J.A., 2004. Determination of the fatty acid profile by 1H‐NMR spectroscopy. Eur. J. Lipid. Sci. Technol. 106, 88-96.
Koster, R., Anderson, M., De, B.E., 1959. Acetic acid for analgesic screening. Fed. Proc. 18, 412-417.
Labib, R.M., Ebada, S.S., Youssef, F.S., Ashour, M.L., Ross, S.A., 2016. Ursolic acid, a natural pentacylcic triterpene from Ochrosia elliptica and its role in the management of certain neglected tropical diseases. Pharmacogn. Mag. 12, 319.
Lin, J.Y., Tang, C.Y., 2007. Determination of total phenolic and flavonoid contents in selected fruits and vegetables, as well as their stimulatory effects on mouse splenocyte proliferation. Food Chem. 101, 140-147.
Mahboubi, A., Asgarpanah, J., Sadaghiyani, P.N., Faizi, M., 2015. Total phenolic and flavonoid content and antibacterial activity of Punica granatum L. var. pleniflora flowers (Golnar) against bacterial strains causing foodborne diseases. BMC. Complement. Altern. Med. 15, 366.
Mehjabin, S., Akanda, M.K.M., Hoque, N., Hasan, N.A.H.M., Parvez, M.G.M., Mosaddik, A. 2024. Flavonoid Intake and Risk of Toxicity in Chronic Metabolic Disease. In; Mishra, N., Ashique, S., Gowda, J., Garg, A. Role of Flavonoids in Chronic Metabolic Diseases: From Bench to Clinic. Scrivener Publishing LLC, Wiley. pp. 511-534.
Makenzi, A.M., Manguro, L.O.A., Owuor, P.O., 2023. Sesquiterpenoids with antiplasmodial activities from Warburgia stuhlmanii Engl. root bark. Trends Phytochem. Res. 7(2), 89-94.
Manik, M., Wahid, M., Islam, S., Pal, A., Ahmed, K., 2013. A comparative study of the antioxidant, antimicrobial and thrombolytic activity of the bark and leaves of Lannea coromandelica (Anacardiaceae). Int. J. Pharm. Sci. Res. 4, 2609.
Marques, S.S., Magalhães, L.M., Tóth, I.V. Segundo, M.A., 2014. Insights on antioxidant assays for biological samples based on the reduction of copper complexes-The importance of analytical conditions. Int. J. Mol. Sci. 15, 11387-11402.
Martins, J., Brijesh, S., 2018. Phytochemistry and pharmacology of anti-depressant medicinal plants: A review. Biomed. Pharmacother. 104, 343-365.
Mbahi, M.A., Mbahi, M.A., Amos, P.I., 2018. Phytochemical screening and anti-diarrheal activity of the pulp and seed extracts of Ziziphus mauritiana in rats. Int. J. Biochem. Res. Rev. 24, 1-9.
Mercier, J.C., Ouldali, N., Melki, I., Basmaci, R., Levy, M., Titomanlio, L., Beyler, C., Meinzer, U., 2021. Severe acute respiratory syndrome coronavirus 2-related multisystem inflammatory syndrome in children mimicking Kawasaki disease. Arch. Cardiovasc. Dis. 114, 426-433.
Mohammadhosseini, M., Frezza, C., Venditti, A., Sarker, S., 2021. A systematic review on phytochemistry, ethnobotany and biological activities of the genus Bunium L. Chem. Biodivers. 18(11), e2100317.
Mohammadhosseini, M., Venditti, A., Akbarzadeh, A., 2019a. The genus Perovskia Kar.: Ethnobotany, chemotaxonomy and phytochemistry: A review. Toxin Rev. 40(4), 484-505.
Mohammadhosseini, M., Venditti, A., Frezza, C., Serafini, M., Bianco, A., Mahdavi, B., 2021b. The genus Haplophyllum Juss.: Phytochemistry and bioactivities—A review. Molecules 26(15), 4664.
Mosnaim, A.D., Wolf, M.E., III. O’donnell, J.J., Hudzik, T., 2020. β-Phenylethylamine and various monomethylated and para-halogenated analogs. Acute toxicity studies in mice. Drug. Chem. Toxicol. 43, 369-372.
Mulat, M., Pandita, A., Khan, F., 2019. Medicinal plant compounds for combating the multi-drug resistant pathogenic bacteria: A review. Curr. Pharm. Biotechnol. 20, 183-196.
Nascimento, G.G., Locatelli, J., Freitas, P.C., Silva, G.L., 2000. Antibacterial activity of plant extracts and phytochemicals on antibiotic-resistant bacteria. Braz. J. Microbiol. 31, 247-256.
Omale, J., Okafor, P.N., 2008. Comparative antioxidant capacity, membrane stabilization, polyphenol composition and cytotoxicity of the leaf and stem of Cissus multistriata. African. J. Biotech. 7(17).
Prasad, S., Kashyap, R.S., Deopujari, J.Y., Purohit, H.J., Taori, G.M., Daginawala, H.F., 2006. Development of an in vitro model to study clot lysis activity of thrombolytic drugs. Thrombosis J. 4, 1-4.
Price, K.S., Waggy, G.T., Conway, R.A., 1974. Brine shrimp bioassay and seawater BOD of petrochemicals. J. Water Pollution Cont. Fed. 63-77.
Prieto, P., Pineda, M., Aguilar, M., 1999. Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: Specific application to the determination of vitamin E. Anal. Biochem. 269, 337-341.
Rajesh, R., Selvakumar, K., 2022. Evaluation of in vitro anthelmintic activity of Lannea coromandelica (Houtt.) Merr. against Pheretima posthuma and Ascardia galli. Res. J. Pharm. Technol. 15, 2539-2542.
Ramadhan, A., Herman, H., Sutrisnawati, S., 2022. Ethanolic extract of Lannea coromandelica stem bark: Histopathology and infiltration of inflammatory cells in the rat's gastric. J. Adv. Pharm. Technol. Res.13, 296.
Ricciotti, E., Fitzgerald, G.A., 2011. Prostaglandins and inflammation. Arterioscler. Thromb. Vasc. Biol. 31, 986-1000.
Saradhajyothi, K., Subbarao, B., 2011. Antibacterial potential of the extracts of the leaves of Azadirachta indica Linn. Not. Sci. Biol. 3.
Saraswati, S., Agrawal, S., Alhaider, A.A., 2013. Ursolic acid inhibits tumor angiogenesis and induces apoptosis through mitochondrial-dependent pathway in Ehrlich ascites carcinoma tumor. Chem. Biol. Interact. 206, 153-165.
Shahriar, M., Mannan, M., Akhter, R., Bhuiyan, M., 2015. Evaluation of in vitro membrane stabilizing activity and thrombolytic activity of Averrhoa bilimbi leaf extracts. Int. J. Pharm. 5, 357-60.
Shetty, N.P., Shetty, P.S., 2009. Epidemiology of Disease in the Tropics. Manson's Tropical Diseases, Vol. 19.
Shinwari, Z., 2011. Antibacterial activity in herbal products used in Pakistan. Pak. J. Bot. 43, 155-162.
Shoeb, H.A., Madkour, H.M., Refahy, L.A., Mohamed, M.A., Saad, A.M., Ghareeb, M.A., 2014. Antioxidant and cytotoxic activities of Gmelina arborea ROXB. leaves. Br. J. Pharm. Res. 4, 125.
Singh, A., Singh, D., Sharma, S., Mittal, N., 2023. A review on biosynthesis, regulation, and applications of terpenes and terpenoids. Trends Phytochem. Res. 7(4), 228-245.
Sreejayan, X., Rao, M., 1997. Nitric oxide scavenging by curcuminoids. J. Pharm. Pharmacol. 49, 105-107.
Stanojević, L., Stanković, M., Nikolić, V., Nikolić, L., Ristić, D., Čanadanovic-Brunet, J., Tumbas, V., 2009. Antioxidant activity and total phenolic and flavonoid contents of Hieracium pilosella L. extracts. Sensors 9, 5702-5714.
Sztanke, M., Sztanke, K., 2017. Biologically important hydrazide-containing fused azaisocytosines as antioxidant agents. Redox Rep. 22, 572-581.
Taber, R.I., Greenhouse, D.D., Rendell, J.K., Irwin, S., 1969. Agonist and antagonist interactions of opioids on acetic acid-induced abdominal stretching in mice. J. Pharmacol. Exp. Ther. 169, 29-38.
Tiwari, P., Kumar, B., Kaur, M., Kaur, G., Kaur, H., 2011. Phytochemical screening and extraction: A review. IPS 1, 98-106.
Tomazetti, J., Ávila, D.S., Ferreira, A.P.O., Martins, J.S., Souza, F.R., Royer, C., Rubin, M.A., Oliveira, M.R., Bonacorso, H.G., Martins, M.A.P., 2005. Baker yeast-induced fever in young rats: Characterization and validation of an animal model for antipyretics screening. J. Neurosci. Methods. 147, 29-35.
Trease, G., Evans, W. 1989. Pharmacognosy. 13th. ELBS/Bailliere Tindall, London, pp. 345-346.
Uddin, J., Islam, M.N., Ali, M.H., Khan, S.A., Labu, Z.K., 2016. Correlation of thrombolytic and membrane stabilizing activities with total flavonoid content aerial parts of Spondias pinnata. Bangladesh Pharm. J. 19, 48-52.
Uddin, N., Hasan, M.R., Hossain, M.M., Sarker, A., Hasan, A.N., Islam, A.M., Chowdhury, M.M. H., Rana, M.S., 2014. In vitro α-amylase inhibitory activity and in vivo hypoglycemic effect of methanol extract of Citrus macroptera Montr. fruit. Asian Pac. J. Trop. Biomed. 4, 473-479.
Umer, S., Tekewe, A., Kebede, N., 2013. Antidiarrhoeal and antimicrobial activity of Calpurnia aurea leaf extract. BMC. Complement. Altern. Med. 13, 1-5.
Upadhya, S., Shanbhag, K.K., Suneetha, G., Balachandra Naidu, M., Upadhya, S., 2004. A study of hypoglycemic and antioxidant activity of Aegle marmelos in alloxan induced diabetic rats. Indian. J. Physiol. Pharmacol. 48, 476-480.
Wahid, A., 2012. In vitro Phytochemical and Biological Investigation of Plant Lannea coromandelica (Family: Anacardiaceae). East West University.
Weerapreeyakul, N., Junhom, C., Barusrux, S., Thitimetharoch, T., 2016. Induction of apoptosis in human hepatocellular carcinoma cells by extracts of Lannea coromandelica (Houtt.) Merr. and Diospyros castanea (Craib) Fletcher. Chin. Med. 11, 19.
Welters, H.J., Diakogiannaki, E., Mordue, J.M., Tadayyon, M., Smith, S.A., Morgan, N.G., 2006. Differential protective effects of palmitoleic acid and cAMP on caspase activation and cell viability in pancreatic β-cells exposed to palmitate. Apoptosis 11, 1231-1238.
Yang, Z.H., Pryor, M., Noguchi, A., Sampson, M., Johnson, B., Pryor, M., Donkor, K., Amar, M., Remaley, A.T., 2019. Dietary palmitoleic acid attenuates atherosclerosis progression and hyperlipidemia in low density lipoprotein receptor deficiency mice. Mol. Nutr. Food Res. 63(12), 1-22.
Yuet Ping, K., Darah, I., Chen, Y., Sreeramanan, S., Sasidharan, S., 2013. Acute and subchronic toxicity study of Euphorbia hirta L. methanol extract in rats. Biomed. Res. Int. 2013.