Login Register Cart 0
Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

1H and 13C NMR Spectral Data of Neolignans Isolated from Piper Species

Author(s): Rosiane Ferreira do Nascimento Marinho, Bianca Roberta Peres Angrisani, Arthur Ladeira Macedo, Davyson de Lima Moreira, Carlos Magno Rocha Ribeiro, Thatyana Rocha Alves Vasconcelos and Alessandra Leda Valverde*

Volume 24, Issue 14, 2020

Page: [1527 - 1554] Pages: 28

DOI: 10.2174/1385272824999200608133542

Price: $65

Abstract

Plants of the genus Piper (Piperaceae) have a pantropical distribution. In Brazil, Piper species are used in traditional medicine to treat many diseases such as inflammation, diabetes, toothache, and fever. Many reports have shown a correlation between the biological activities of Piper species and neolignans, a secondary metabolite class obtained from the shikimic acid biosynthetic pathway. This review aims to provide detailed information on the structural identification of neolignans isolated from Piper species by 1H and 13C Nuclear Magnetic Resonance (NMR) spectroscopy. These searchable data enable rapid identification and routine analysis of neolignans from extracts of the Piper species.

Keywords: Biological activity, neolignans, natural products, secondary metabolites, Piperaceae, spectral data.

Next »
Graphical Abstract

[1]
Gottlieb, O.; Yoshida, M. Lignóides com atenção especial à química das neolignanas. Quim. Nova, 1984, 7, 250-273.
[2]
Teponno, R.B.; Kusari, S.; Spiteller, M. Recent advances in research on lignans and neolignans. Nat. Prod. Rep., 2016, 33(9), 1044-1092.
[http://dx.doi.org/10.1039/C6NP00021E] [PMID: 27157413]
[3]
Benevides, P.J.; Sartorelli, P.C.; Kato, M.J. Phenylpropanoids and neolignans from Piper regnellii. Phytochemistry, 1999, 52(2), 339-343.
[http://dx.doi.org/10.1016/S0031-9422(99)00177-6]
[4]
Trindade, F.T.; Stabeli, R.G.; Facundo, V.A.; Cardoso, C.T.; Silva, M.A.D.; Gil, L.H.; Jardim, I.S. Evaluation of larvicidal activity of the methanolic extracts of Piper alatabaccum branches and P. tuberculatum leaves and compounds isolated against Anopheles darlingi. Rev. Bras. Farmacogn., 2012, 22(5), 979-984.
[http://dx.doi.org/10.1590/S0102-695X2012005000039]
[5]
Nascimento, J.C.D.; Paula, V.F.D.; David, J.M.; David, J.P. Occurrence, biological activities and 13C NMR data of amides from Piper (Piperaceae). Quim. Nova, 2012, 35(11), 2288-2311.
[http://dx.doi.org/10.1590/S0100-40422012001100037]
[6]
Mgbeahuruike, E.E.; Yrjönen, T.; Vuorela, H.; Holm, Y. Bioactive compounds from medicinal plants: focus on Piper species. S. Afr. J. Bot., 2017, 112, 54-69.
[http://dx.doi.org/10.1016/j.sajb.2017.05.007]
[7]
Parmar, V.S.; Jain, S.C.; Bisht, K.S.; Jain, R.; Taneja, P.; Jha, A.; Tyagi, O.D.; Prasad, A.K.; Wengel, J.; Olsen, C.E. Phytochemistry of the genus Piper. Phytochemistry, 1997, 46(4), 597-673.
[http://dx.doi.org/10.1016/S0031-9422(97)00328-2]
[8]
Macedo, A.L.; Dos Santos, T.C.C.; Valverde, A.L.; Moreira, D.L.; Vasconcelos, T.R.A. An overview of neolignans of the genus Piper L.: isolation methods and biological activities. Mini Rev. Med. Chem., 2017, 17(8), 693-720.
[http://dx.doi.org/10.2174/1389557516666161130094826] [PMID: 27903229]
[9]
Brambilla, L.Z.S.; Endo, E.H.; Cortez, D.A.G.; Lima, M.M.S.; Filho, B.P.D. Piper regnellii extract biopolymer-based microparticles: production, characterization and antifungal activity. J. Appl. Microbiol., 2018, 124(1), 75-84.
[http://dx.doi.org/10.1111/jam.13618] [PMID: 29072357]
[10]
Silva, M.A.; Passarini, G.M.; Martinez, L.N.; Facundo, V.A.; Teles, C.G.B.; Kuehn, C.C. Chemical constituents and bioactivities of essential oils from plants of the genus Piper L. (Piperaceae): a review. South. Am. J. Bas. Educ. Tech. Technol., 2019, 6(2), 776-817.
[11]
Macedo, A.L.; Duprat, R.C.; Moreira, D.L.; Kaplan, M.A.C.; Vasconcelos, T.R.A.; Pinto, L.C.; Montenegro, R.C.; Ratcliffe, N.A.; Mello, C.B.; Valverde, A.L. Isolation of a larvicidal compound from Piper solmsianum C.DC. (Piperaceae). Nat. Prod. Res., 2018, 32(22), 2701-2704.
[http://dx.doi.org/10.1080/14786419.2017.1374265] [PMID: 28882070]
[12]
Macedo, A.L.; da Silva, D.P.D.; Moreira, D.L.; de Queiroz, L.N.; Vasconcelos, T.R.A.; Araujo, G.F.; Kaplan, M.A.C.; Pereira, S.S.C.; de Almeida, E.C.P.; Valverde, A.L.; Robbs, B.K. Cytotoxicity and selectiveness of Brazilian Piper species towards oral carcinoma cells. Biomed. Pharmacother., 2019, 110, 342-352.
[http://dx.doi.org/10.1016/j.biopha.2018.11.129] [PMID: 30529767]
[13]
Agrawal, P.K.; Thakur, R.S. 13C NMR spectroscopy of lignan and neolignan derivatives. Magn. Reson. Chem., 1985, 23(6), 389-418.
[http://dx.doi.org/10.1002/mrc.1260230602]
[14]
Chen, S.; Huang, H.Y.; Cheng, M.J.; Wu, C.C.; Ishikawa, T.; Peng, C.F.; Chang, H.S.; Wang, C.J.; Wong, S.L.; Chen, I.S. Neolignans and phenylpropanoids from the roots of Piper taiwanense and their antiplatelet and antitubercular activities. Phytochemistry, 2013, 93, 203-209.
[http://dx.doi.org/10.1016/j.phytochem.2013.03.008] [PMID: 23582215]
[15]
Yeh, L-A.; Chen, J.; Baculi, F.; Gingrich, D.E.; Shen, T. Inhibition of metalloproteinase by futoenone derivatives. Bioorg. Med. Chem. Lett., 1995, 5(15), 1637-1642.
[http://dx.doi.org/10.1016/0960-894X(95)00282-X]
[16]
Lin, L.C.; Shen, C.C.; Shen, Y.C.; Tsai, T.H. Anti-inflammatory neolignans from Piper kadsura. J. Nat. Prod., 2006, 69(5), 842-844.
[http://dx.doi.org/10.1021/np0505521] [PMID: 16724856]
[17]
Reddy, S.D.; Siva, B.; Poornima, B.; Kumar, D.A.; Tiwari, A.K.; Ramesh, U.; Babu, K.S. New free radical scavenging neolignans from fruits of Piper attenuatum. Pharmacogn. Mag., 2015, 11(42), 235-241.
[http://dx.doi.org/10.4103/0973-1296.153063] [PMID: 25829760]
[18]
Sarkar, D.; Kundu, S.; De, S.; Hariharan, C.; Saha, P.; Manna, A.; Chattopadhyay, S.; Chatterjee, M. The antioxidant activity of allylpyrocatechol is mediated via decreased generation of free radicals along with escalation of antioxidant mechanisms. Phytother. Res., 2013, 27(3), 324-329.
[http://dx.doi.org/10.1002/ptr.4720] [PMID: 22585425]
[19]
Muharini, R.; Liu, Z.; Lin, W.; Proksch, P. New amides from the fruits of Piper retrofractum. Tetrahedron Lett., 2015, 56(19), 2521-2525.
[http://dx.doi.org/10.1016/j.tetlet.2015.03.116]
[20]
Shen, T.; Hussaini, I. Kadsurenone and other related lignans as antagonists of platelet-activating factor receptor. In: Methods in enzymology; Elsevier, 1990, Vol. 187, pp. 446-454.
[21]
Shen, T.Y.; Hwang, S.B.; Chang, M.N.; Doebber, T.W.; Lam, M.H.; Wu, M.S.; Wang, X.; Han, G.Q.; Li, R.Z. Characterization of a platelet-activating factor receptor antagonist isolated from haifenteng (Piper futokadsura): specific inhibition of in vitro and in vivo platelet-activating factor-induced effects. Proc. Natl. Acad. Sci. USA, 1985, 82(3), 672-676.
[http://dx.doi.org/10.1073/pnas.82.3.672] [PMID: 2983307]
[22]
Chen, Z.; Yu, P.; Xu, P. Anti-platelet activating factor constituents, 2, 5-diaryltetrahydrofuran type lignans, from Piper futokadsura Sied et Zucc. Chin. J. Chines. Mat. Med., 1993, 18(5), 294-4.
[23]
Teng, C.M.; Yu, S.M.; Ko, F.N.; Chen, C.C.; Wang, W.C.; Chen, K.Y.; Huang, Y.L.; Huang, T.F. Comparison of the actions of some platelet-activating factor antagonists on platelets and aortic smooth muscles. Eur. J. Pharmacol., 1991, 205(2), 151-156.
[http://dx.doi.org/10.1016/0014-2999(91)90813-6] [PMID: 1812005]
[24]
Tsai, W.J.; Shen, C.C.; Tsai, T.H.; Lin, L.C. Lignans from the aerial parts of Saururus chinensis: isolation, structural characterization, and their effects on platelet aggregation. J. Nat. Prod., 2014, 77(1), 125-131.
[http://dx.doi.org/10.1021/np400772h] [PMID: 24387347]
[25]
Ding, D.D.; Wang, Y.H.; Chen, Y.H.; Mei, R.Q.; Yang, J.; Luo, J.F.; Li, Y.; Long, C.L.; Kong, Y. Amides and neolignans from the aerial parts of Piper bonii. Phytochemistry, 2016, 129, 36-44.
[http://dx.doi.org/10.1016/j.phytochem.2016.07.004] [PMID: 27452451]
[26]
Han, G.Q.; Wei, L.H.; Li, C.L.; Qiao, L.; Jia, Y.Z.; Zheng, Q.T. [The isolation and identification of PAF inhibitors from Piper wallichii (Miq.) Hand- Mazz and P. hancei Maxim]. Yao Xue Xue Bao, 1989, 24(6), 438-443.
[PMID: 2609983]
[27]
Lemos, C.O.T.; Svidzinsk, T.I.E.; Baeza, L.C.; Miranda, N.; Nakamura, C.V.; Cortez, D.A.G.; Filho, L.C.; Cabral, V.F. Evaluation of antifungal activity of extracts of Piper regnellii obtained by supercritical fluid extraction. Nat. Prod. Res., 2013, 27(24), 2355-2359.
[http://dx.doi.org/10.1080/14786419.2013.830215] [PMID: 24007562]
[28]
Marçal, F.J.B.; Cortez, D.A.G.; Ueda-Nakamura, T.; Nakamura, C.V.; Dias Filho, B.P. Activity of the extracts and neolignans from Piper regnellii against methicillin-resistant Staphylococcus aureus (MRSA). Molecules, 2010, 15(4), 2060-2069.
[http://dx.doi.org/10.3390/molecules15042060] [PMID: 20428025]
[29]
Pessini, G.L.; Filho, B.P.D.; Nakamura, C.V.; Cortez, D.A.G. Antifungal activity of the extracts and neolignans from Piper regnellii (Miq.) C. DC. var. pallescens (C.DC.). Yunck. J. Braz. Chem. Soc., 2005, 16(6A), 1130-1133.
[http://dx.doi.org/10.1590/S0103-50532005000700007]
[30]
De Campos, M.P.; Cechinel Filho, V.; Da Silva, R.Z.; Yunes, R.A.; Zacchino, S.; Juarez, S.; Cruz, R.C.B.; Cruz, A.B. Evaluation of antifungal activity of Piper solmsianum C.DC. var. solmsianum (Piperaceae). Biol. Pharm. Bull., 2005, 28(8), 1527-1530.
[http://dx.doi.org/10.1248/bpb.28.1527] [PMID: 16079508]
[31]
Lemos, C.O.T.; dos Santos Garcia, V.A.; Goncalves, R.M.; Leal, I.C.R.; Siqueira, V.L.D.; Filho, L.C.; Cabral, V.F. Supercritical extraction of neolignans from Piper regnelli var. pallescens. J. Supercrit. Fluids, 2012, 71, 64-70.
[http://dx.doi.org/10.1016/j.supflu.2012.07.003]
[32]
Brambilla, L.Z.; Endo, E.H.; Cortez, D.A.; Dias Filho, B.P. Anti-biofilm activity against Staphylococcus aureus MRSA and MSSA of neolignans and extract of Piper regnellii. Rev. Bras. Farmacogn., 2017, 27(1), 112-117.
[http://dx.doi.org/10.1016/j.bjp.2016.08.008]
[33]
Longato, G.B.; Fiorito, G.F.; Costa, D.B.V.; de Sousa, I.M.O.; Tinti, S.V.; Ruiz, A.L.T.G.; de Almeida, S.M.V.; Padilha, R.J.R.; Foglio, M.A.; de Carvalho, J.E. Different cell death responses induced by eupomatenoid-5 in MCF-7 and 786-0 tumor cell lines. Toxicol. In Vitro, 2015, 29(5), 1026-1033.
[http://dx.doi.org/10.1016/j.tiv.2015.04.002] [PMID: 25882683]
[34]
Valadares, M.C.; de Carvalho, I.C.T.; Junior, L.O.; Vieira, M.S.; Benfica, P.L.; de Carvalho, F.S.; Andrade, L.V.S.; Lima, E.M.; Kato, M.J. Cytotoxicity and antiangiogenic activity of grandisin. J. Pharm. Pharmacol., 2009, 61(12), 1709-1714.
[http://dx.doi.org/10.1211/jpp.61.12.0017] [PMID: 19958595]
[35]
Valadares, M.C.; de Oliveira, L.M., Jr; de Carvalho, F.S.; Andrade, L.V.; dos Santos, A.P.; de Oliveira, V. Gil, Ede.S.; Kato, M.J. Chemoprotective effect of the tetrahydrofuran lignan grandisin in the in-vivo rodent micronucleus assay. J. Pharm. Pharmacol., 2011, 63(3), 447-451.
[http://dx.doi.org/10.1111/j.2042-7158.2010.01200.x] [PMID: 21749394]
[36]
Moreira, D.L.; Paiva, R.A.; Marques, A.M.; Borges, R.M.; Barreto, A.L.S.; Curvelo, J.A.R.; Cavalcanti, J.F.; Romanos, M.T.V.; Soares, R.M.A.; Kaplan, M.A.C. Bioactive Neolignans from the Leaves of Piper rivinoides Kunth (Piperaceae). Rec. Nat. Prod., 2016, 10(4), 472-484.
[37]
Luize, P.S.; Ueda-Nakamura, T.; Dias Filho, B.P.; Cortez, D.A.G.; Morgado-Díaz, J.A.; de Souza, W.; Nakamura, C.V. Ultrastructural alterations induced by the neolignan dihydrobenzofuranic eupomatenoid-5 on epimastigote and amastigote forms of Trypanosoma cruzi. Parasitol. Res., 2006, 100(1), 31-37.
[http://dx.doi.org/10.1007/s00436-006-0241-9] [PMID: 16783543]
[38]
Vendrametto, M.C.; Santos, A.O.; Nakamura, C.V.; Dias Filho, B.P.; Cortez, D.A.G.; Ueda-Nakamura, T. Evaluation of antileishmanial activity of eupomatenoid-5, a compound isolated from leaves of Piper regnellii var. pallescens. Parasitol. Int., 2010, 59(2), 154-158.
[http://dx.doi.org/10.1016/j.parint.2009.12.009] [PMID: 20064628]
[39]
Garcia, F.P.; Bidóia, D.L.; Nakamura, T.U.; Silva, S.O.; Nakamura, C.V. Eupomatenoid-5 isolated from leaves of Piper regnellii induces apoptosis in Leishmania amazonensis. Evid-Based Compl. Alternat. Med., 2013, 2013, 940531
[http://dx.doi.org/10.1155/2013/940531] [PMID: 23573160 ]
[40]
Zhang, H.J.; Tamez, P.A.; Vu, D.H.; Ghee, T.T.; Nguyen, V.H.; Le, T.X.; Le, M.H.; Nguyen, M.C.; Do, T.T.; Soejarto, D.D.; Fong, H.H.; Pezzuto, J.M. Antimalarial compounds from Rhaphidophora decursiva. J. Nat. Prod., 2001, 64(6), 772-777.
[http://dx.doi.org/10.1021/np010037c] [PMID: 11421741]
[41]
Nogueira, C.D.R.; de Mello, R.P.; Kato, M.J.; Cabral, M.M. Disruption of Chrysomya megacephala growth caused by lignan grandisin. J. Med. Entomol., 2009, 46(2), 281-283.
[http://dx.doi.org/10.1603/033.046.0212] [PMID: 19351078]
[42]
Harmatha, J.; Nawrot, J. Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety. Entomol. Exp. Appl., 2002, 104(1), 51-60.
[http://dx.doi.org/10.1046/j.1570-7458.2002.00990.x]
[43]
Cabral, M.M.; Mendonça, P.M.; Gomes, C.M.; Barbosa Filho, J.M.; Queiroz, M.M.; Mello, R.P. Biological activity of neolignans on the post-embryonic development of Chrysomya megacephala. Fitoterapia, 2007, 78(1), 20-24.
[http://dx.doi.org/10.1016/j.fitote.2006.09.011] [PMID: 17067762]
[44]
Narciso, J.O.A.; Soares, R.O.; Mallet, J.R.S.; Guimarães, A.É.; Chaves, M.C.O.; Filho, J.M.B.; Maleck, M. Burchellin: study of bioactivity against Aedes aegypti. Parasit. Vectors, 2014, 7(1), 172.
[http://dx.doi.org/10.1186/1756-3305-7-172] [PMID: 24713267]
[45]
Cabral, M.M.; Alencar, J.A.; Guimarães, A.E.; Kato, M.J. Larvicidal activity of grandisin against Aedes aegypti. J. Am. Mosq. Control Assoc., 2009, 25(1), 103-105.
[http://dx.doi.org/10.2987/08-5828.1] [PMID: 19432075]
[46]
Leite, A.C.C.; Kato, M.J.; Soares, R.O.; Guimarães, A.E.; Mallet, J.R.S.; Cabral, M.M. Grandisin caused morphological changes larval and toxicity on Aedes aegypti. Rev. Bras. Farmacogn., 2012, 22(3), 517-521.
[http://dx.doi.org/10.1590/S0102-695X2012005000016]
[47]
Chauret, D.C.; Bernard, C.B.; Arnason, J.T.; Durst, T.; Krishnamurty, H.G.; Vindas, P.S.; Moreno, N.; Roman, L.S.; Poveda, L. Insecticidal neolignans from Piper decurrens. J. Nat. Prod., 1996, 59(2), 152-155.
[http://dx.doi.org/10.1021/np960036y] [PMID: 8991948]
[48]
Da Silva, R.Z.; Yunes, R.A.; de Souza, M.M.; Monache, F.D.; Filho, V.C. Antinociceptive properties of conocarpan and orientin obtained from Piper solmsianum C. DC. var. solmsianum (Piperaceae). J. Nat. Med., 2010, 64(4), 402-408.
[http://dx.doi.org/10.1007/s11418-010-0421-x] [PMID: 20473574]
[49]
Achenbach, H.; Grob, J.; Dominguez, X.A.; Cano, G.; Star, J.V.; Brussolo, L.D.C.; Muñoz, G.; Salgado, F.; López, L. Lignans neolignans and norneolignans from Krameria cystisoides. Phytochemistry, 1987, 26(4), 1159-1166.
[http://dx.doi.org/10.1016/S0031-9422(00)82370-5]
[50]
Ahmad, F.; Tawan, C. Phytochemical studies on Piper umbellatum L. Sarawak. ARBEC, 2002, 2002, 1-4.
[51]
Tapu, D.; Dixon, D.A.; Roe, C. 13C NMR spectroscopy of “Arduengo-type” carbenes and their derivatives. Chem. Rev., 2009, 109(8), 3385-3407.
[http://dx.doi.org/10.1021/cr800521g] [PMID: 19281270]
[52]
Arellanes, A.J.; Díaz, R.L.; Meckes, M.; Tapia, A.; Salinas, G.M.M.; Herrera, J.L.; Mulia, L.Y. Antiprotozoal and antimycobacterial activities of pure compounds from Aristolochia elegans rhizomes. Evid-Based Compl. Alternat Med., 2012, 2012, 593403
[http://dx.doi.org/10.1155/2012/593403] [PMID: 22454670]
[53]
Thebpatipha, S. Some constituents of the stems of Piper interruptum opiz. J. Sci. Soc. Thailand, 1988, 14, 225-231.
[http://dx.doi.org/10.2306/scienceasia1513-1874.1988.14.225]
[54]
Luize, P.S.; Nakamura, T.U.; Dias Filho, B.P.; Cortez, D.A.G.; Nakamura, C.V. Activity of neolignans isolated from Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi. Biol. Pharm. Bull., 2006, 29(10), 2126-2130.
[http://dx.doi.org/10.1248/bpb.29.2126] [PMID: 17015964]
[55]
Scodro, R.B.; Pires, C.T.; Carrara, V.S.; Lemos, C.O.; Filho, L.C.; Souza, V.A.; Corrêa, A.G.; Siqueira, V.L.; Lonardoni, M.V.; Cardoso, R.F.; Cortez, D.A. Anti-tuberculosis neolignans from Piper regnellii. Phytomedicine, 2013, 20(7), 600-604.
[http://dx.doi.org/10.1016/j.phymed.2013.01.005] [PMID: 23474218]
[56]
Maxwell, A.; Dabideen, D.; Reynolds, W.F.; McLean, S. Neolignans from Piper aequale. Phytochemistry, 1999, 50(3), 499-504.
[http://dx.doi.org/10.1016/S0031-9422(98)00545-7]
[57]
Vega, M.; Carvalho, M.; Velandia, J.; Braz-Filho, R. Chemical constituents from Piper fulvescens-Complete 1H and 13C NMR assignment of neolignans and 3beta-O-beta-D-glucopyranosyl-5, 6-epoxy-beta-sitosterol. Rev. Latinoam. Quím., 2001, 29(2), 63-72.
[58]
Campos, M.P.; Filho, V.C.; Silva, R.Z.; Yunes, R.A.; Monache, F.D.; Cruz, A.B. Antibacterial activity of extract, fractions and four compounds extracted from Piper solmsianum C. DC. VAR. solmsianum (Piperaceae). Z. Natforsch. C J. Biosci., 2007, 62(3-4), 173-178.
[http://dx.doi.org/10.1515/znc-2007-3-404] [PMID: 17542481]
[59]
Freixa, B.; Vila, R.; Ferro, E.A.; Adzet, T.; Cañigueral, S. Antifungal principles from Piper fulvescens. Planta Med., 2001, 67(9), 873-875.
[http://dx.doi.org/10.1055/s-2001-18838] [PMID: 11745030]
[60]
Lange, G.L.; Organ, M.G.; Ruangrungsi, N.; Prathanturarug, S. An N-methyl aristolactam and an oxygenated cyclohexane derivative from Piper ribesioides. Phytochemistry, 1992, 31(7), 2397-2400.
[http://dx.doi.org/10.1016/0031-9422(92)83285-7]
[61]
Johann, S.; Cota, B.B.; Souza-Fagundes, E.M.; Pizzolatti, M.G.; Resende, M.A.; Zani, C.L. Antifungal activities of compounds isolated from Piper abutiloides Kunth. Mycoses, 2009, 52(6), 499-506.
[http://dx.doi.org/10.1111/j.1439-0507.2008.01636.x] [PMID: 19076283]
[62]
Ripperger, H.; Anh, N.H.; Himmelreich, U.; Van Sung, T.; Adam, G. Polar eupomatenoids from Caryodaphnosis tonkinensis. Phytochemistry, 1995, 39(1), 213-215.
[http://dx.doi.org/10.1016/0031-9422(94)00890-6] [PMID: 7546550]
[63]
Pessini, G.L.; Dias Filho, B.P.; Nakamura, C.V.; Cortez, D.A.G. Antibacterial activity of extracts and neolignans from Piper regnellii (Miq.) C. DC. var. pallescens (C. DC.). Yunck. Mem. Inst. Oswaldo Cruz, 2003, 98(8), 1115-1120.
[http://dx.doi.org/10.1590/S0074-02762003000800025] [PMID: 15049100]
[64]
Ma, Y.; Han, G.Q.; Wang, Y.Y. PAF antagonistic benzofuran neolignans from Piper kadsura. Yao Xue Xue Bao, 1993, 28(5), 370-373.
[PMID: 8237383]
[65]
Konishi, T.; Konoshima, T.; Daikonya, A.; Kitanaka, S. Neolignans from Piper futokadsura and their inhibition of nitric oxide production. Chem. Pharm. Bull. (Tokyo), 2005, 53(1), 121-124.
[http://dx.doi.org/10.1248/cpb.53.121] [PMID: 15635246]
[66]
Sánchez, C.L.; Corral, M.A.; González, L.J.; Dorado, M.M.; García, I.R. Rh (II)-catalyzed enantioselective synthesis of acuminatin through a C–H insertion reaction of a non-stabilized carbenoid. Tetrahedron, 2013, 69(26), 5511-5516.
[http://dx.doi.org/10.1016/j.tet.2013.04.086]
[67]
Green, T.P.; Galinis, D.L.; Wiemer, D.F. Three neolignans from the roots of Piper capense. Phytochemistry, 1991, 30(5), 1649-1652.
[http://dx.doi.org/10.1016/0031-9422(91)84226-I]
[68]
Singh, S.K.; Ashok, P.K.; Olsen, C.E.; Jha, A.; Jain, S.C.; Parmar, V.S.; Wenge, J. Neolignans and alkaloids from Piper argyrophylum. Phytochemistry, 1996, 43(6), 1355-1360.
[http://dx.doi.org/10.1016/S0031-9422(96)00502-X]
[69]
Tyagi, O.D.; Prasad, A.K.; Wengel, J.; Boll, P.; Olsen, C.E.; Parmar, V.; Sharma, N.; Jha, A.; Bisht, K. Neolignans from Piper schmidtii and reassignment of the structure of schmiditin. Acta Chem. Scand., 1995, 49(2), 142-148.
[http://dx.doi.org/10.3891/acta.chem.scand.49-0142]
[70]
Chang, M.N.; Han, G.Q.; Arison, B.H.; Springer, J.P.; Hwang, S.B.; Shen, T.Y. Neolignans from Piper futokadsura. Phytochemistry, 1985, 24(9), 2079-2082.
[http://dx.doi.org/10.1016/S0031-9422(00)83126-X]
[71]
Tyagi, O.D.; Wengel, J.; Prasad, A.K.; Boll, P.M.; Olsen, C.E.; Pati, H.N.; Bisht, K.; Parmar, V.; Francis, G. Benzofuranoid neolignans from Piper wightii Miq. Acta Chem. Scand., 1994, 48, 1007-1011.
[http://dx.doi.org/10.3891/acta.chem.scand.48-1007]
[72]
Tyagi, O.D.; Jensen, S.; Boll, P.M.; Sharma, N.K.; Bisht, K.S.; Parmar, V.S. Lignans and neolignans from Piper schmidtii. Phytochemistry, 1993, 32(2), 445-448.
[http://dx.doi.org/10.1016/S0031-9422(00)95012-X]
[73]
Koul, J.; Koul, S.; Taneja, S.; Dhar, K. Oxygenated cyclohexanes from Piper cubeb. Phytochemistry, 1996, 41(4), 1097-1099.
[http://dx.doi.org/10.1016/0031-9422(95)00737-7]
[74]
Taneja, S.; Koul, S.; Pushpangadan, P.; Dhar, K.; Daniewski, W.; Schilf, W. Oxygenated cyclohexanes from Piper species. Phytochemistry, 1991, 30(3), 871-874.
[http://dx.doi.org/10.1016/0031-9422(91)85269-6]
[75]
Pradhan, P.; Desai, S.; Badheka, L.; Banerji, A. Neolignans from Indian Piper species: structure of hookerinone A, a novel neolignan. Nat. Prod. Lett., 1994, 4(1), 35-42.
[http://dx.doi.org/10.1080/10575639408043889]
[76]
Matsui, K.; Munakata, K. The structure of piperenone, a new insect antifeeding substance from Piper futokadzura. Tetrahedron Lett., 1975, 16(24), 1905-1908.
[http://dx.doi.org/10.1016/S0040-4039(00)72318-5]
[77]
Iida, T.; Ito, K. Four phenolic neolignans from Magnolia liliflora. Phytochemistry, 1983, 22(3), 763-766.
[http://dx.doi.org/10.1016/S0031-9422(00)86979-4]
[78]
Prasad, A.K.; Tyagi, O.D.; Wengel, J.; Boll, P.M.; Olsen, C.E.; Gupta, S.; Sharma, N.K.; Bisht, K.S.; Parmar, V.S. Lignans and neolignans from stems of Piper wightii. Tetrahedron, 1994, 50(35), 10579-10586.
[http://dx.doi.org/10.1016/S0040-4020(01)89597-1]
[79]
Nguyen, T.T.M.; Nguyen, T.T.; Lee, H-S.; Jun, C-D.; Min, B.S.; Kim, J.A. Neolignan derivatives from the flower of Magnolia biondii Pamp. and their effects on IL-2 expression in T-cells. Nat. Prod. Sci., 2017, 23(2), 119-124.
[http://dx.doi.org/10.20307/nps.2017.23.2.119]
[80]
Wenkert, E.; Gottlieb, H.E.; Gottlieb, O.R.; Pereira, M.O.S.; Formiga, M.D. 13C NMR spectroscopy of neolignans. Phytochemistry, 1976, 15(10), 1547-1551.
[http://dx.doi.org/10.1016/S0031-9422(00)88934-7]
[81]
Ying, M.; Qiu, H.G. Benzofuranoid neolignans from Piper kadsura. Acta Bot. Sin., 1993, 35(9), 687-692.
[82]
Jensen, S.; Olsen, C.E.; Tyagi, O.D.; Boll, P.M.; Hussaini, F.A.; Gupta, S.; Bisht, K.S.; Parmar, V.S. Neolignans and an isoprenylated phenol from Piper clarkii. Phytochemistry, 1994, 36(3), 789-792.
[http://dx.doi.org/10.1016/S0031-9422(00)89819-2]
[83]
Kim, K.H.; Choi, J.W.; Ha, S.K.; Kim, S.Y.; Lee, K.R. Neolignans from Piper kadsura and their anti-neuroinflammatory activity. Bioorg. Med. Chem. Lett., 2010, 20(1), 409-412.
[http://dx.doi.org/10.1016/j.bmcl.2009.10.016] [PMID: 19900811]
[84]
Kim, K.H.; Choi, J.W.; Ha, S.K.; Kim, S.Y.; Lee, K.R. Corrigendum to “Neolignans from Piper kadsura and their anti-neuroinflammatory activity”. Bioorg. Med. Chem. Lett., 2010, 20(10), 3186-3187.
[http://dx.doi.org/10.1016/j.bmcl.2010.04.003]
[85]
Prasad, A.K.; Tyagi, O.D.; Wengel, J.; Boll, P.M.; Olsen, C.E.; Bisht, K.S.; Singh, A.; Sarangi, A.; Kumar, R.; Jain, S.C. Neolignans and a lignan from Piper clarkii. Phytochemistry, 1995, 39(3), 655-658.
[http://dx.doi.org/10.1016/0031-9422(95)00036-7]
[86]
Khan, M.R.; Gray, A.I.; Waterman, P.G. Neolignans from stem bark of Ocotea veraguensis. Phytochemistry, 1987, 26(4), 1155-1158.
[http://dx.doi.org/10.1016/S0031-9422(00)82369-9]
[87]
Liu, H.X.; He, M.T.; Tan, H.B.; Gu, W.; Yang, S.X.; Wang, Y.H.; Li, L.; Long, C.L. Xanthine oxidase inhibitors isolated from Piper nudibaccatum. Phytochem. Lett., 2015, 12, 133-137.
[http://dx.doi.org/10.1016/j.phytol.2015.03.005]
[88]
Matsui, K.; Munakata, K. Four new neolignans from Piper futokadzura. Tetrahedron Lett., 1976, 17(48), 4371-4374.
[http://dx.doi.org/10.1016/0040-4039(76)80118-9]
[89]
Ling, S.; Caifang, W.; Yu, X.; Qiu’an, W. Synthesis and biological activity of Benzodihydrofuran neolignans and their mannich base derivatives. Youji Huaxue, 2015, 35(7), 1537-1543.
[http://dx.doi.org/10.6023/cjoc201502003]
[90]
Huyan, T.; Tang, R.; Li, J.; Liu, Y.; Yang, H.; Li, Q. Chemical constituents of Piper wallichii (Miq.) Hand.-Mazz. and inhibitory effects on Tca83 cells. Biomed. Res., 2016, 27(1), 220-224.
[91]
Boll, P.M.; Prasad, A.K.; Tyagi, O.D.; Wengel, J.; Olsen, C.E.; Kumar, N.; Bisht, K.S.; Parmar, V.S. Neolignans, cyclohexanes and alkaloids from Piper wightii. Recl. Trav. Chim. Pays Bas, 1996, 115(1), 9-12.
[http://dx.doi.org/10.1002/recl.19961150103]
[92]
Takahashi, S.; Ogiso, A. The structure of futoquinol, a constituent of Piper futokadzura SIEB. et ZUCC. Chem. Pharm. Bull. (Tokyo), 1970, 18(1), 100-104.
[http://dx.doi.org/10.1248/cpb.18.100]
[93]
Ma, Y.; Han, G.Q.; Li, C.L.; Cheng, J.R.; Arison, B.H.; Hwang, S.B. Neolignans from Piper polysyphorum C.DC. Yao Xue Xue Bao, 1991, 26(5), 345-350.
[PMID: 1957684]
[94]
Ming, L.S.; Qiu, H.G.; Arison, B.; Chang, M. Studies on the chemical constituents of Piper hancei Maxim (III). Acta Bot. Sin., 1987, 29(3), 293-296.
[PMID: 3661206]
[95]
Prasad, A.K.; Tyagi, O.D.; Wengel, J.; Boll, P.M.; Olsen, C.E.; Sharma, N.K.; Bisht, K.S.; Gupta, S.; Parmar, V.S. Lignans and neolignans from stems and fruits of Piper wightii. Tetrahedron, 1994, 50(7), 2231-2240.
[http://dx.doi.org/10.1016/S0040-4020(01)85081-X]
[96]
Pradhan, P.; Banerji, A. Stereochemistry of diastereomeric neolignans from Piper hookeri by nuclear magnetic resonance spectroscopy. Phytochemical Analysis: An I. J. Plant Chem. Biochem. Techn., 1998, 9(2), 71-74.
[http://dx.doi.org/10.1002/(SICI)1099-1565(199803/04)9:2<71:AID-PCA390>3.0.CO;2-0]
[97]
Green, T.P.; Wiemer, D.F. Four neolignan ketones from Piper capense. Phytochemistry, 1991, 30(11), 3759-3762.
[http://dx.doi.org/10.1016/0031-9422(91)80104-9]
[98]
Wiart, C. Lead Compounds from Medicinal Plants for the Treatment of Neurodegenerative Diseases, 1st ed; Academic Press: San Diego, 2014.
[99]
Martins, R.C.; Lago, J.H.G.; Albuquerque, S.; Kato, M.J. Trypanocidal tetrahydrofuran lignans from inflorescences of Piper solmsianum. Phytochemistry, 2003, 64(2), 667-670.
[http://dx.doi.org/10.1016/S0031-9422(03)00356-X] [PMID: 12943793]
[100]
Xue, P.; Wang, L.P.; Jiao, X.Z.; Jiang, Y.J.; Xiao, Q.; Luo, Z.G.; Xie, P.; Liang, X.T. Total synthesis of (-)-talaumidin and (-)-galbelgin. J. Asian Nat. Prod. Res., 2009, 11(3), 281-287.
[http://dx.doi.org/10.1080/10286020802675191] [PMID: 19408154]
[101]
Sumathykutty, M.; Rao, J.M. 8-Hentriacontanol and other constituents from Piper attenuatum. Phytochemistry, 1991, 30(6), 2075-2076.
[http://dx.doi.org/10.1016/0031-9422(91)85070-G]
[102]
Zhang, S.; Liu, X.; Zhang, L.; Wan, D. Chemical constituents of Haifengteng. Nat. Prod. Res. Dev., 1992, 4(3), 1-4.
[103]
Barata, L.E.; Baker, P.M.; Gottlieb, O.R.; Rùveda, E.A. Neolignans of Virola surinamensis. Phytochemistry, 1978, 17(4), 783-786.
[http://dx.doi.org/10.1016/S0031-9422(00)94227-4]
[104]
Abdallah, O.; Ibrahaim, Z. Chemical constituents of Piper cuneifolium, structure of a new neolignan. Pharmazie, 1996, 51(3), 187-188.
[105]
Shimomura, H.; Sashida, Y.; Oohara, M. Lignans from Machilus thunbergii. Phytochemistry, 1987, 26(5), 1513-1515.
[http://dx.doi.org/10.1016/S0031-9422(00)81847-6]
[106]
Zhang, K.; Chen, C.; Chen, D. Chemical constituents of Piper polysyphorum. Acta Bot. Yunn., 1997, 19, 211-212.
[107]
Takaoka, D.; Watanabe, K.; Hiroi, M. Studies on lignoids in Lauraceae. II. Studies on lignans in the leaves of Machilus Japonica Sieb. et Zucc. B. Chem. Soc. JPN, 1976, 49(12), 3564-3566.
[http://dx.doi.org/10.1246/bcsj.49.3564]
[108]
Riggs, N.; Stevens, J. Some constituents of Piptocalyx moorei Oliv. Aust. J. Chem., 1962, 15(2), 305-313.
[http://dx.doi.org/10.1071/CH9620305]
[109]
Doskotch, R.; Flom, M. Acuminatin, a new bis-phenylpropide from Magnolia acuminata L. Tetrahedron, 1972, 28(18), 4711-4717.
[http://dx.doi.org/10.1016/0040-4020(72)88079-7]
[110]
Sadhu, S.K.; Okuyama, E.; Fujimoto, H.; Ishibashi, M. Separation of Leucas aspera, a medicinal plant of Bangladesh, guided by prostaglandin inhibitory and antioxidant activities. Chem. Pharm. Bull. (Tokyo), 2003, 51(5), 595-598.
[http://dx.doi.org/10.1248/cpb.51.595] [PMID: 12736464]
[111]
Kuo, Y.H.; Chen, C.H.; Lin, Y.L. New lignans from the heartwood of Chamaecyparis obtusa var. formosana. Chem. Pharm. Bull. (Tokyo), 2002, 50(7), 978-980.
[http://dx.doi.org/10.1248/cpb.50.978] [PMID: 12130860]
[112]
Urzúa, A.; Freyer, A.J.; Shamma, M. 2, 5-diaryl-3, 4-dimethyltetrahydro-furanoid lignans. Phytochemistry, 1987, 26(5), 1509-1511.
[http://dx.doi.org/10.1016/S0031-9422(00)81846-4]
[113]
Fonseca, S.F.; Barata, L.E.; Rúveda, E.A.; Baker, P.M. 13C nuclear magnetic resonance spectral and conformational analysis of naturally occurring tetrahydrofuran lignans. Can. J. Chem., 1979, 57(4), 441-443.
[http://dx.doi.org/10.1139/v79-071]
[114]
Martins, R.C.; Latorre, L.R.; Sartorelli, P.; Kato, M.J. Phenylpropanoids and tetrahydrofuran lignans from Piper solmsianum. Phytochemistry, 2000, 55(7), 843-846.
[http://dx.doi.org/10.1016/S0031-9422(00)00295-8] [PMID: 11190407]
[115]
Holloway, D.; Scheinmann, F. Two lignans from Litsea grandis and L. gracilipes. Phytochemistry, 1974, 13(7), 1233-1236.
[http://dx.doi.org/10.1016/0031-9422(74)80107-X]
[116]
Saad, J.M.; Soepadamo, E.; Fang, X.P.; McLaughlin, J.L.; Fanwick, P.E. (-)-Grandisin form Cryptocarya crassinervia. J. Nat. Prod., 1991, 54(6), 1681-1683.
[http://dx.doi.org/10.1021/np50078a033] [PMID: 1812217]
[117]
Queiroz, A.S.D.R. Estudo Químico de Piper tectoniifolium Kunth (PIPERACEAE). , Master Thesis, Universidade Federal do Rio de Janeiro, Rio de Janeiro (RJ),M.. 2016.
[118]
Shimomura, H.; Sashida, Y.; Oohara, M. Lignans from Machilus thunbergii. Phytochemistry, 1988, 27(2), 634-636.
[http://dx.doi.org/10.1016/0031-9422(88)83162-5]
[119]
Hattori, M.; Hada, S.; Kawata, Y.; Tezuka, Y.; Kikuchi, T.; Namba, T. New 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans from the aril of Myristica fragrans. Chem. Pharm. Bull. (Tokyo), 1987, 35(8), 3315-3322.
[http://dx.doi.org/10.1248/cpb.35.3315] [PMID: 3427727]
[120]
Lopes, N.P.; de Almeida Blumenthal, E.E.; Cavalheiro, A.J.; Kato, M.J.; Yoshida, M. Lignans, γ-lactones and propiophenones of Virola surinamensis. Phytochemistry, 1996, 43(5), 1089-1092.
[http://dx.doi.org/10.1016/S0031-9422(96)00408-6]
[121]
Yañez, X.R.; Diaz, A.M.; Diaz, P.P. Neolignans from Mezilaurus itauba. Phytochemistry, 1986, 25(8), 1953-1956.
[http://dx.doi.org/10.1016/S0031-9422(00)81182-6]
[122]
Zhang, S.X.; Chen, K.; Liu, X.J.; Zhang, D.C.; Wiedmann, T.W.T.; Leu, S.L.; McPhail, A.T.; Lee, K-H. The isolation and structural elucidation of three new neolignans, piperulins [corrected] A, B, and C, as platelet activating factor receptor antagonists from Piper puberulum. J. Nat. Prod., 1995, 58(4), 540-547.
[http://dx.doi.org/10.1021/np50118a009] [PMID: 7623032]
[123]
Ma, Y.; Han, G.; Jiang, T.; Yang, X. Neolignans fom Piper kadsura (II). Chin. Chem. Lett., 1992, 8, 635-636.
[124]
Chaturvedula, V.S.P.; Hecht, S.M.; Gao, Z.; Jones, S.H.; Feng, X.; Kingston, D.G. New neolignans that inhibit DNA polymerase β lyase. J. Nat. Prod., 2004, 67(6), 964-967.
[http://dx.doi.org/10.1021/np030507y] [PMID: 15217274]
[125]
Wang, M.; Wu, A.; Pan, X.; Yang, H. Total synthesis of two naturally occurring bicyclo[3.2.1]octanoid neolignans. J. Org. Chem., 2002, 67(15), 5405-5407.
[http://dx.doi.org/10.1021/jo011077o] [PMID: 12126439]
[126]
Quílez, A.; Berenguer, B.; Gilardoni, G.; Souccar, C.; de Mendonça, S.; Oliveira, L.F.; Martín-Calero, M.J.; Vidari, G. Anti-secretory, anti-inflammatory and anti-helicobacter pylori activities of several fractions isolated from Piper carpunya Ruiz & Pav. J. Ethnopharmacol., 2010, 128(3), 583-589.
[http://dx.doi.org/10.1016/j.jep.2010.01.060] [PMID: 20152892]
[127]
Jiang, R-W.; Mak, T.C.; Fung, K-P. Molecular structures of two bicyclo-(3.2.1)-octanoid neolignans from Piper kadsura. J. Mol. Struct., 2003, 654(1-3), 177-182.
[http://dx.doi.org/10.1016/S0022-2860(03)00221-7]
[128]
Ma, Y.; Han, G.Q.; Liu, Z.J. Studies on PAF antagonistic bicyclo(3,2,1) octanoid neolignans from Piper kadsura. Yao Xue Xue Bao, 1993, 28(3), 207-211.
[PMID: 8368081]
[129]
Mahindru, R.; Taneja, S.; Dhar, K.; Brown, R. Reassignment of structures of the neolignans, magnosalin and andamanicin. Phytochemistry, 1993, 32(4), 1073-1075.
[http://dx.doi.org/10.1016/0031-9422(93)85260-X]
[130]
Yamamura, S.; Niwa, M.; Nonoyama, M.; Terada, Y. Three novel neolignans from Heterotropa Takaoi M. Tetrahedron Lett., 1978, 19(49), 4891-4894.
[http://dx.doi.org/10.1016/S0040-4039(01)85763-4]
[131]
Reilly, M.J.; Wallis, A.F.; Lundquist, K.; Stomberg, R. Stereochemistry of neolignans-A revised structure for a neolignan isolated from the roots of Piper capense. J. Wood Chem. Technol., 1992, 10(4), 471-483.
[http://dx.doi.org/10.1080/02773819208545792]
[132]
Malhotra, S.; Koul, S.; Taneja, S.; Pushpangadan, P.; Dhar, K. A neolignan from Piper sumatranum. Phytochemistry, 1990, 29(8), 2733-2734.
[http://dx.doi.org/10.1016/0031-9422(90)85233-6]
[133]
Badheka, L.P.; Prabhu, B.R.; Mulchandani, N.B. Lignans of Piper cubeba. Phytochemistry, 1987, 26(7), 2033-2036.
[http://dx.doi.org/10.1016/S0031-9422(00)81752-5]
[134]
Isogai, A.; Murakoshi, S.; Suzuki, A.; Tamura, S. Structures of new dimeric phenylpropanoids from Myristica fragrans Houtt. Agric. Biol. Chem., 1973, 37(6), 1479-1486.
[http://dx.doi.org/10.1271/bbb1961.37.1479]
[135]
Ogiso, A.; Kurabayashi, M.; Mishima, H.; Woods, M. The structure of futoenone, a novel spiro-cyclohexadienone derivative. Tetrahedron Lett., 1968, 9(16), 2003-2008.
[http://dx.doi.org/10.1016/S0040-4039(01)99075-6]
[136]
Ogiso, A.; Kurabayashi, M.; Takahashi, S.; Mishima, H.; Woods, M. The structure and total via Piper futokadzura SIEB. et ZUCC. Chem. Pharm. Bull. (Tokyo), , 1970, 18(1), 105-114.
[http://dx.doi.org/10.1248/cpb.18.105]

Rights & Permissions Print Cite
Article Metrics
12
© 2024 Bentham Science Publishers | Privacy Policy