Inhibition of D – Amino Acid Oxidase by Chromatographic Fractions and Kaempferol-3-O-rutinoside Isolated from Philenoptera cyanescens Leaves
http://www.doi.org/10.26538/tjnpr/v7i1.25
Keywords:
Antipsychotic agents, Kaempferol-3-Orutinoside, Philenoptera cyanescens, Inhibitory activity, D-amino acid oxidaseAbstract
Philenoptera cyanescens (PC) leaves are used ethno-medically for the treatment of mental disorder in Southwestern Nigeria. The crude extract and solvent fractions of the PC leaves have earlier been reported for in vivo antipsychotic properties in rodents. The D-amino acid oxidase (DAO) assay is an in vitro anti-psychotic model. However, there is little or no report on the inhibition of DAO by medicinal plants. This study investigates the in vitro antipsychotic activity of a bioactive compound, DCM and EtOAc chromatographic sub-fractions from Philenoptera cyanescens leaves. The inhibitory effect of the isolated compound, sub-fractions from DCM (a-j) and EtOAc (A-K), Risperidone and Haloperidol standards were tested on Pig Kidney D-amino acid oxidase enzyme (pkDAO), using D–Kynurenine as substrate. Percentage inhibition was measured in a fluorescence microplate reader with an excitation and emission wavelengths of 355 and 460 nm, respectively. Structure of isolated compound was elucidated using NMR and FT-IR analyses. PCDe (61.9%) at 0.2 mg/mL showed a higher percentage inhibition than Risperidone (43.2%) and Haloperidol (18.3%) among the PC DCM sub-fractions. Interestingly, PCEF gave 100% inhibition of the enzyme, when compared with other sub-fractions and standards. The ethyl acetate sub-fraction F showed best inhibitory activity, Kaempferol-3-O-rutinoside showed percentage inhibition of 13.7% comparable to the standard drug, Haloperidol. This compound has been reported earlier but isolated from this plant and tested on the antipsychotic property using D amino acid oxidase for the first time.
References
World Flora Online, 2022. Lonchocarpus cyanescens (Schum. & Thonn.) Benth. Published on the Internet; http://www.worldfloraonline.org/taxon/wfo-0000199336.
Burkill HM. The Useful Plants of West Tropical Africa. (2nded.) Royal Botanic Gardens, Kew. 1985. 621 p
Moronkola DO, Oladosu IA. Chemical compositions of Lonchocarpus cyanescens Benth. (Fabaceae)— Case study of its volatile oils, and two Triterpenoids. Am. J. Plant Sci. 2013;4:1653–1659.
Iwu MM, Anyanwu BN. Phytotherapeutic profile of Nigerian herbs. I: Anti-inflammatory and anti-arthritic agents. J. Ethnopharmacol. 1982; 6(3):263–74.
Cardon D, Jansen PCM. Philenoptera cyanescens(Schumach. &Thonn.) Roberty. In: Jansen PCM.,Cardon D. (eds) PROTA, Wageningen, Netherlands. 2005
Igoli JO, Ogaji OG, Tor-Anyiin TA, Igoli NP. Traditional medicine practice amongst the Igede people of Nigeria. Part II. Afr. J. Trad. Complement. Altern. Med.2005; 2(2):134–152.
Idu M, Erhabor JO, Efijuemue HM. Documentation on medicinal plants sold in markets in Abeokuta, Nigeria. Trop. J. Pharm. Res.2010; 9(2):110–118.
Adewuyi A, Oderinde RA, Rao BV, Prasad RBN. Chemical composition and molecular speciation of the triacylglycerol of the oils of Lonchocarpus sericeus and Lonchocarpus cyanescens. Nat. Prod. Res. 2012; 26(20):1954–1956.
Sonibare MA, Soladoye MO, Subuloye TO. Ethnobotanical survey of anti-psychotic plants in Lagos and Ogun States of Nigeria. Eur. J. Sci. Res. 2008; 19: 634–643.
Fozia AA, Victor K, Armelle TM, Matthias H, Andreas K, Albert N, Beatrice I, Abiy Y, and Thomas E. Cytotoxic flavonoids from two Lonchocarpus species. Nat. Prod. Res. 2018; 33(18): 2609–2617.
Angeline AO, Phillip OO, Lawrence AOM, Ishola OI, Regina AN, Charles OO and Sylvia AO. Analgesics from Lonchocarpus eriocalyx Harms.Trends Phytochem. Res. 2018; 2(4):253–260.
Emanuelle MBM, da Silva L, Ana Lúcia TG, Ruiz,JE, de CarvalhoAM, Pomini LHP and Silvana MOS. Antiproliferative activity and chemical constituents of Lonchocarpus cultratus (Fabaceae). Nat. Prod. Res. 2019; 35(12); 2056–2059.
Kawazoe T, Park HK, Iwana S, Tsuge H, Fukui K. Human D-amino acid oxidase: An update and review. Chem. Rec. 2007; 7:305–315.
Khoronenkova SV, Tishkov VI. High-throughput screening assay for D-amino acid oxidase. Anal. Biochem. 2008; 374(2): 405–410.
Schell MJ, Molliver ME, Snyder SH. D-serine, an endogenous synaptic modulator: Localization to astrocytes and glutamate-stimulated release. Proceedings of the National Academy of Sciences of the USA.1995; 92:3948–3952.
Madeira C, Freitas ME, Vargas-Lopes C, Wolosker H, Panizzutti R. Increased brain D-amino acid oxidase (DAAO) activity in schizophrenia. Schizophr. Res. 2008; 101(1–3):76-83.
Hashimoto K, FukushimaT, Shimizu E, Komatsu N, Watanabe H, Shinoda N, Nakazato M, Kumakiri C, Okada S, Hasegawa H, Imai K, Iyo M. Decreased serum levels of Dserine in patients with schizophrenia – Evidence in support of the N-methyl-D-aspartate receptor hypofunction hypothesis of schizophrenia. Arch. Gen. Psychiatry. 2003; 60:572–576.
Song Z, Ogaya T, Ishii K, Ichiba H, Iizuka H, Fukushima T. Utilization of Kynurenic acid produced from D-Kynurenine in an in vitro assay of D-amino acid oxidase activity. J. Health Sci. 2010; 56:341–346.
Sonibare MA, Umukoro S,Shonibare ET. Antipsychotic property of aqueous and ethanolic extracts of Lonchocarpus cyanescens (Schumach and Thonn.) Benth. (Fabaceae) in rodents. J Nat. Med. 2012; 66:127–132.
Arowona IT, Sonibare MA, Umukoro S. Antipsychotic property of solvent-partitioned fractions of Lonchocarpus cyanescens leaf extract in mice. J Basic Clin. Physiol. Pharmacol. 2014; 25(2):235–40.
Sonibare MA, Arowona IT, Rauf K. Antipsychotic effects of Philenoptera cyanescens (Schum. & Thonn.) Roberty (Leguminosae) leaf extract and fractions against ketamineinduced psychosis in mice. Acta Pharm. Sci. 2020; 58(2):132–152.
Iwasa S, Tabara H, Song Z, Nakabayashi M, Yokoyama Y, Fukushima T. Inhibition of D-amino acid oxidase activity by antipsychotic drugs evaluated by a fluorometric assay using D-kynurenine as substrate. Yakugaku Zasshi. 2011; 131:1111–1116.
Al-Hamoud GA, Orfali SR, Sugimoto S, Yamano Y, Alothyqi N, Alzahrani AM, Matsunami K.Four new flavonoids isolated from the aerial parts of Cadaba rotundifolia Forssk. (Qadab). Mol.2019; 24(11):2167.
Hilal Y, Engelhardt UH. A new myricetinrhamnodiglucoside from Camellia sinensis.Nat. Prod. Res. 2009; 23(17):1621–1629.
Dehaghani ZA, Gholamreza A and Dinani MS. Isolation and identification of Nicotiflorin and Narcissin from the aerial parts of Peucedanum aucheri Boiss. J. Agric. Sci. and Tech. A. 2017; 7: 45–51.
Jian-Hong Y, Tamara PK, Laura EM, Xi Q, Yongsoo C, Hongmei C, Rui Y, Megan S, Scott P, Ying L, Li-Qin W, Andrew DM, Richard BV-B, John MP, Harry HSF, Ye-Gao C, Hong-Jie Z. Isolation and evaluation of kaempferol glycosides from the fern Neocheiropteris palmatopedata. 2010; 71(5-6):641–647.
Kozaki A, Iwasa S, Hosoda S, Nishiguchi Y, Nakayama M, Ichiba H, Fukushima T. Fluorimetric assay for D-amino acid oxidase activity in rat brain homogenate by using Dkynurenine as a substrate. Biosci. Trends. 2012;6(5):241 –247.
Shishikura M, Hakariya H, Iwasa S, Yoshio T, Ichiba H, Yorita K, Fukui K, Fukushima T. Evaluation of human Damino acid oxidase inhibition by antipsychotic drugs in vitro. Biosci. Trends. 2014; 8(3):149–154.
Legoabe LJ, Petzer A, Petzer JP. Selected chromone derivatives as inhibitors of monoamine oxidase". Bioorg. Med. Chem. Lett. 2012; 22(17): 5480–5484.
Legoabe, LJ, Petzer A, Petzer JP. Selected C7-substituted chromone derivatives as monoamine oxidase inhibitors. Bioorg. Chem. 2012; 45(0):1–11.
Legoabe, LJ, Petzer A, Petzer JP. Inhibition of monoamine oxidase by selected C6-substituted chromone derivatives. Eur. J. Med. Chem. 2012; 49(0):343–353.
Ferraris D, Duvall B, Ko YS, Thomas AG, Rojas C, Majer P, Hashimoto K, Tsukamoto T. Synthesis and biological evaluation of D-amino acid oxidase inhibitors. J. Med. Chem. 2008; 51:3357–3359.
Duplantier AJ, Becker SL, Bohanon MJ, Borzilleri KA, Chrunyk BA, James TD, Lain-Yen H,El-Kattan A,James LC,Liu S,Lu J,Maklad N,Mansour MN,Mente S,Piotrowski MA,Sakya SM,Sheehan S,Steyn SJ,Strick CA, Victoria A, Williams VA, Zhang L.Discovery, SAR, and pharmacokinetics of a novel 3-hydroxyquinoline-2(1H)-one series of potent D-amino acid oxidase (DAAO) inhibitors. J. Med. Chem. 2009; 52:3576–3585.
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