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ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

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Review Article

Nuclear Magnetic Resonance Spectroscopic Behaviour of Some Selective Natural Flavonoids: A Look Through

Author(s): Shyamal K. Jash*, Dilip Gorai, Lalan C. Mandal and Rajiv Roy

Volume 17, Issue 2, 2020

Page: [185 - 196] Pages: 12

DOI: 10.2174/1570193X16666181224110603

Price: $65

Abstract

Flavonoids are considered as a significant class of compounds among the natural products, exhibiting a variety of structural skeletons as well as multidirectional biological potentials. In structural elucidations of natural products, Nuclear Magnetic Resonance (NMR) spectroscopy has been playing a vital role; the technique is one of the sharpest tools in the hands of natural products chemists. The present resume deals with hard-core applications of such spectral technique, particularly in structural elucidation of flavonoids; different NMR techniques including 1H-NMR, 13C-NMR, and 2D-NMR [viz. 1H-1H COSY, COLOC, HMBC, HMQC] are described in detail.

Keywords: Class of flavonoids, natural flavonoids, spectroscopic behavior, NMR spectral behaviour, NMR techniques, spinspin couplings.

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[1]
Jash, S.K.; Brahmachari, G. Recent progress in the research of naturally occurring flavonoids: A look through. Signpost Open Access J. Org. Biomol. Chem., 2013, 1, 65-168.
[2]
Brahmachari, G.; Mandal, N.C.; Jash, S.K.; Roy, R.; Mandal, L.C.; Mukhopadhyay, A.; Behera, B.; Majhi, S.; Mondal, A.; Gangopadhyay, A. Evaluation of the antimicrobial potential of two flavonoids isolated from limnophila plants. Chem. Biodivers., 2011, 8(6), 1139-1151.
[http://dx.doi.org/10.1002/cbdv.201000264] [PMID: 21674786]
[3]
Jash, S.K.; Mondal, S. Bioactive flavonoid fisetin - A molecule of pharmacological interest. Signpost Open Access J. Org. Biomol. Chem., 2014, 2, 89-128.
[4]
Jash, S.K.; Singh, R.K.; Majhi, S.; Sarkar, A.; Gorai, D. Peltophorum pterocarpum: Chemical and pharmacological aspects. Int. J. Pharm. Sci. Res., 2014, 5, 26-36.
[5]
Kuete, V.; Ango, P.Y.; Fotso, G.W.; Kapche, G.D.W.F.; Dzoyem, J.P.; Wouking, A.G.; Ngadjui, B.T.; Abegaz, B.M. Antimicrobial activities of the methanol extract and compounds from Artocarpus communis (Moraceae). BMC Complement. Altern. Med., 2011, 11, 42.
[http://dx.doi.org/10.1186/1472-6882-11-42] [PMID: 21612612]
[6]
Kemp, W. Organic Spectroscopy, 3rd ed; Macmillan Education: UK, 1991.
[http://dx.doi.org/10.1007/978-1-349-15203-2 ]
[7]
Silverstein, R.M.; Bassler, G.C.; Morrill, T.C. Spectrometric Identification of Organic Compounds, 5th ed; New York: Wiley, 1991.
[8]
Nuclear Magnetic Resonance (NMR): Definition, Principle and Theory. http://www.environmentalpollution.in/pollution/regulation-and-monitoring/nuclear-magnetic-resonance-nmr-definition-principle-and-theory/1933 (Accessed: Novenber 01, 2018).
[9]
Doddrell, D.M.; Pegg, D.T.; Bendall, M.R. Distortionless enhancement of NMR signals by polarization transfer. J. Magn. Reson., 1982, 48, 323-327.
[10]
Aue, W.P.; Bartholdi, E.; Ernst, R.R. Two-dimensional spectroscopy. Application to nuclear magnetic resonance. J. Chem. Phys., 1976, 64, 2229-2246.
[http://dx.doi.org/10.1063/1.432450]
[11]
Martin, G.E.; Zekter, A.S. Two-Dimensional NMR Methods for Establishing Molecular Connectivity; VCH Publishers: New York, 1988.
[12]
Mateescu, G.D.; Valeriu, A. 2D NMR Density Matrix and Product Operator Treatment; PTR Prentice Hall: New Jersey, 1993.
[13]
Keeler, J. Understanding NMR Spectroscopy, 2nd ed; Wiley, 2010.
[14]
Friebolin, H. Understanding NMR Spectroscopy, 2nd ed; Wiley, 2010.
[15]
The Nobel Prize in Chemistry. 1991.https://www.nobelprize. org/prizes/chemistry/1991/summary/ (Accessed November 01, 2018).
[16]
Wüthrich, K. Protein recognition by NMR. Nat. Struct. Biol., 2000, 7(3), 188-189.
[http://dx.doi.org/10.1038/73278] [PMID: 10700272]
[17]
Damberger, F.F.; Christen, B.; Pérez, D.R.; Hornemann, S.; Wüthrich, K. Cellular prion protein conformation and function. Proc. Natl. Acad. Sci. USA, 2011, 108(42), 17308-17313.
[http://dx.doi.org/10.1073/pnas.1106325108] [PMID: 21987789]
[18]
Chai, X.Y.; Song, Y.L.; Xu, Z.R.; Shi, H.M.; Bai, C.C.; Bi, D.; Wen, J.; Li, F.F.; Tu, P.F. Itosides J-N from Itoa orientalis and structure - anti-COX-2 activity relationship of phenolic glycosides. J. Nat. Prod., 2008, 71(5), 814-819.
[http://dx.doi.org/10.1021/np800014s] [PMID: 18412396]
[19]
Takashima, J.; Komiyama, K.; Ishiyama, H.; Kobayashi, J.; Ohsaki, A. Brosimacutins J-M, four new flavonoids from Brosimum acutifolium and their cytotoxic activity. Planta Med., 2005, 71(7), 654-658.
[http://dx.doi.org/10.1055/s-2005-871272] [PMID: 16041652]
[20]
Furusawa, M.; Tanaka, T.; Ito, T.; Nakaya, K.; Iliya, I.; Ohyama, M.; Iinuma, M.; Murata, H.; Inatomi, Y.; Inada, A.; Nakanishi, T.; Matsushita, S.; Kubota, Y.; Sawa, R.; Takahashi, Y. Flavonol glycosides in leaves of two Diospyros species. Chem. Pharm. Bull. (Tokyo), 2005, 53(5), 591-593.
[http://dx.doi.org/10.1248/cpb.53.591] [PMID: 15863940]
[21]
Ito, C.; Itoigawa, M.; Kumagaya, M.; Okamoto, Y.; Ueda, K.; Nishihara, T.; Kojima, N.; Furukawa, H. Isoflavonoids with antiestrogenic activity from Millettia pachycarpa. J. Nat. Prod., 2006, 69(1), 138-141.
[http://dx.doi.org/10.1021/np050341w] [PMID: 16441086]
[22]
Bedane, K.G.; Kusari, S.; Bullach, A.; Masesane, I.B.; Mihigo, S.O.; Spitellerb, M.; Majinda, R.R.T. Chemical constituents of the root bark of Erythrina droogmansiana. Phytochem. Lett., 2017, 20, 84-88.
[http://dx.doi.org/10.1016/j.phytol.2017.04.005]
[23]
Tanaka, H.; Hattori, H.; Oh-Uchi, T.; Sato, M.; Yamaguchi, R.; Sako, M.; Tateishi, Y. Two new isoflavanones from Erythrina costaricensis. J. Asian Nat. Prod. Res., 2008, 10(9-10), 983-987.
[http://dx.doi.org/10.1080/10286020802217598] [PMID: 19003619]
[24]
Jang, J.; Na, M.; Thuong, P.T.; Njamen, D.; Mbafor, J.T.; Fomum, Z.T.; Woo, E.R.; Oh, W.K. Prenylated flavonoids with PTP1B inhibitory activity from the root bark of Erythrina mildbraedii. Chem. Pharm. Bull. (Tokyo), 2008, 56(1), 85-88.
[http://dx.doi.org/10.1248/cpb.56.85] [PMID: 18175982]
[25]
Li, R.T.; Li, J.T.; Wang, J.K.; Han, Q.B.; Zhu, Z.Y.; Sun, H.D. Three new flavonoid glycosides isolated from Elsholtzia bodinieri. Chem. Pharm. Bull. (Tokyo), 2008, 56(4), 592-594.
[http://dx.doi.org/10.1248/cpb.56.592] [PMID: 18379115]
[26]
Cui, L.; Thuong, P.T.; Lee, H.S.; Njamen, D.; Mbafor, J.T.; Fomum, Z.T.; Lee, J.; Kim, Y.H.; Oh, W.K. Four new chalcones from Erythrina abyssinica. Planta Med., 2008, 74(4), 422-426.
[http://dx.doi.org/10.1055/s-2008-1034327] [PMID: 18484536]
[27]
El-Seedi, H.R. Antimicrobial arylcoumarins from Asphodelus microcarpus. J. Nat. Prod., 2007, 70(1), 118-120.
[http://dx.doi.org/10.1021/np060444u] [PMID: 17253862]
[28]
Mbukwa, E.; Chacha, M.; Majinda, R.R.T. Phytochemical constituents of Vangueria infausta: Their radical scavenging and antimicrobial activities. Issue in Honor of Prof. Berhanu Abegaz ARKIVOC, 2007, IX, 104-112.
[29]
Miyaichi, Y.; Hanamitsu, E.; Kizu, H.; Tomimori, T. Studies on the constituents of Scutellaria species (XXII). Constituents of the roots of Scutellaria amabilis HARA. Chem. Pharm. Bull. (Tokyo), 2006, 54(4), 435-441.
[http://dx.doi.org/10.1248/cpb.54.435] [PMID: 16595941]
[30]
Claridge, T. High-Resolution NMR Techniques in Organic Chemistry, 1st ed; Elsevier: UK, 1999.
[31]
Markham, K.R. Techniques of Flavonoid Identification; Academic Press: London, 1982.
[32]
Agrawal, P.K. Carbon-13 NMR of Flavonoids; Agrawal, P.K., Ed.; Elsevier: New York, 1989, p. 507.

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