Isolation of an isoflavonoid and a terpenoid from the heartwood of Baphia nitida Lodd. (camwood)

Ndukwe, Gloria Ihuoma; Oluah, Amarachi; Fekarurhobo, Godswill Kuta

doi:10.2478/auoc-2020-0002

Abstract

Chromatographic separation of methanolic extract of Baphia nitida heartwood gave two crystalline solids characterized as 3,9-dimethoxy-6aR,11aR-dihydro-6H-benzofuro(3,2-C)[1]benzopyran (also known as homopterocarpin) with molecular formula C₁₇H₁₆O₄ (1.57% yield) and 2,4-dimethoxybenzaldehyde C₉H₁₀O₃ (2.27% yield). Each of the isolated compounds showed a single spot on developed thin layer chromatographic plate under ultra-violet light (254 nm) and spray reagent (10% sulfuric acid in methanol solution). Structural elucidation was achieved using Fourier transform infrared (FT-IR) spectroscopy, one and two-dimension nuclear magnetic resonance (NMR) techniques. Distortionless enhancement by polarization transfer-edited-heteronuclear single quantum coherence (DEPT-ed-HSQC) was also a useful tool that aided the characterization of the two secondary metabolites isolated from Baphia nitida heartwood.

References

[1]. S. Keskar, A. Bhandage, S. Deshmukh, M. Abtryankar, Flavonoids: An overview, Journal of Pharmacy Research 2 (2009) 1148-1154.
Search in Google Scholar Back to article
[2]. A. Kar, Pharmacognosy and pharmacobiotechnology (Revised expanded second edition), New Delhi: New Age International Limited Publishers (2007).
Search in Google Scholar Back to article
[3]. B.C. Onyekwere, O.E. JohnBull, R.I. Uchegbu, Isolation and characterization of baphianoside from the leaves of Baphia nitida, Journal of Natural Science Research 4 (2014) 2224-3186.
Search in Google Scholar Back to article
[4]. O.R. Omobuwajo, S.A. Adesanya, G.O. Babalola, Isofavonoids from Pycnantus angolensis and Baphia nitida, Journal of Phytochemistry 31 (1992) 1013-1014.10.1016/0031-9422(92)80059-N
Search in Google Scholar Back to article
[5]. N.D. Onwukaeme, T.Y. Lot, A pharmacological evaluation of Baphia nitida Lodd. (Leguminosae) ethanolic extract on rats and mice, Phytotherapy Research 5 (1991) 254-257.10.1002/ptr.2650050605
Search in Google Scholar Back to article
[6]. N.D. Onwukaeme, T. Y. Lot, The effect of Baphia nitida Lodd. (leguminosae) extract on the gastrointestinal tract of rats and mice, Phytotherapy Research 6 (1992) 129-132.10.1002/ptr.2650060305
Search in Google Scholar Back to article
[7]. D. Kone-Bamba, Y. Pelissier, Z.F. Ozoukou, D. Kouao, Hemostatic activity of 216 plants used in traditional medicine in the Ivory Coast, Plant Medicinal Phytotherapy 21 (1987) 122-130.
Search in Google Scholar Back to article
[8] O.O. Adeyemi, O.K. Yemitan, A.E. Taiwo, Neurosedative and muscle-relaxant activities of ethyl acetate extract of Baphia nitida, AFZEL Journal of Ethnopharmacology 106 (2006) 312-316.10.1016/j.jep.2005.11.035
Search in Google Scholar Back to article
[9]. O.O. Adeyemi, A.J. Akindele, Antidiarrheal activity of the ethyl acetate extract of Baphia nitida, Journal of Ethnopharmacology 116 (2008) 407-412.10.1016/j.jep.2007.12.004
Search in Google Scholar Back to article
[10]. A. Arnone, L. Camarda, L. Merlini, G. Nasini, D.A.-H. Taylor, Isoflavonoid constituents of the West African red wood Baphia nitida, Phytochemistry 20 (1981) 799-801.10.1016/0031-9422(81)85178-3
Search in Google Scholar Back to article
[11]. M. Chabbi, P. Chabert, C. Vanthraon-Serecheau, B. Weniger, O. Modibo, H. Corstigens, I. Sente, L. Declerq, A. Lobstein, Acetylated Flavonol Pentaglycosides from Baphia nitida leaves, Phytochemistry Letters 3 (2010) 70-74.10.1016/j.phytol.2009.12.002
Search in Google Scholar Back to article
[12]. A. Kato, K. Noriko, M. Saori, M. Yuka, A. Isao, I. Kyoko, A. Naoki, A. Alison, J.N. Robert, Imminosugars from Baphia nitida, Journal of Phytochemistry 69 (2008) 1261-1265.10.1016/j.phytochem.2007.11.01818191969
Search in Google Scholar Back to article
[13]. G.I. Ndukwe, C.M. Ojinnaka, A.O. Oyedeji, Novel bioactive triterpenoid saponin from the fruits of Napoleonaea imperialis P. Beauv (Lecythidaceae), International Journal of Chemical Studies 4 (2016) 80-87.
Search in Google Scholar Back to article
[14]. R. Sheel, K. Nisha, J. Kumar, Preliminary phytochemical screening of methanolic extract of Clerodendron infortunatum, IOSR Journal of Applied Chemistry 1 (2014) 10-13.10.9790/5736-07121013
Search in Google Scholar Back to article
[15]. M. Yoshikawa, X. Fegming, M. Hisashe, H. Hiroki, N. Seikou, Structure of new flavonoids from Cuban propolis, Journal of Agriculture and Food Chemistry 53 (2009) 9010-9016.
Search in Google Scholar Back to article
[16]. A.L. Piccineli, C.M. Fernandez, O. Cuesta-Rubio, L. Rastrelli, Isoflavonoids isolated from Cuban propolis, Journal of Agriculture and Food Chemistry 53 (2005) 9010-9016.10.1021/jf051875616277396
Search in Google Scholar Back to article
[17]. E.Y Ouafae, A.I.T.O. Nabil, I.G. Quaaziz, S.S.K. Amal, K. Saloua, B.M.B. Bahia, E.L.B. Mohammed, Q.I. Ali, B. Rachid, Phytochemical screening and thin layer chromatography of two medicinal plants: Adasonia digitata (Bombacaceae) and Acacia raddiana (fabaceae), Journal of Pharmacognosy and Phytochemistry 6 (2017) 10-15.
Search in Google Scholar Back to article
[18]. C.O. Alebiosu, A.J. Yusuf, Phytochemical screening, thin layer chromatographic studies and UV analysis of extracts of Citrullus lanatus, Journal of Pharmaceutical, Chemical and Biological Sciences 3 (2015) 214-220.
Search in Google Scholar Back to article
[19]. R. Costil, F. Fernandez-Nieto, R.C. Atkinson, J. Clayden, α-Methyl phenylglycines by asymmetric α-arylation of alanine and their effect on the conformational preference of helical Aib foldamers, Organic & Biomolecular Chemistry 16 (2018) 2757-2761.10.1039/C8OB00551F
Search in Google Scholar Back to article
[20]. A.D. Khalaji, K. Fejfasovaz M. Dusek, Synthesis and characterization of two dimine Schiff bases derived from 2, 4- dinethe-oxygenaldehyde. The crystal structure of N, N-bis (2,4-dinethoxybenzylidene), 1,2-diamiind ethane, Acta Chimica Slovenica 57 (2010) 257-261.
Search in Google Scholar Back to article

Isolation of an isoflavonoid and a terpenoid from the heartwood of Baphia nitida Lodd. (camwood)

Abstract

Paradigm

My account